# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_20marb_O_0m
_database_code_depnum_ccdc_archive 'CCDC 2312111'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-06-27 downloaded from the CCDC.
;
_audit_creation_date             2024-04-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         '6(H2 O), C6 H N12 O4, O'
_chemical_formula_sum            'C6 H13 N12 O11'
_chemical_formula_weight         429.244
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           ' P -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x,-y,z+1/2

_symmetry_Int_Tables_number      7
_cell_length_a                   10.6901(9)
_cell_length_b                   6.3378(6)
_cell_length_c                   12.8174(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.095(3)
_cell_angle_gamma                90
_cell_volume                     842.26(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5273
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      3.28
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1466 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.8871.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_description       irregular
_exptl_crystal_F_000             442.299
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.9987
_diffrn_reflns_Laue_measured_fraction_max 0.9990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13670
_diffrn_reflns_point_group_measured_fraction_full 0.9232
_diffrn_reflns_point_group_measured_fraction_max 0.9047
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         3.21
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.810
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              16
_reflns_limit_l_min              -14
_reflns_number_gt                3133
_reflns_number_total             3787
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.6540
_refine_diff_density_min         -0.7453
_refine_diff_density_rms         0.0881
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.4(19)
_refine_ls_d_res_high            0.7498
_refine_ls_d_res_low             6.3378
_refine_ls_goodness_of_fit_ref   1.0490
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.0490
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0982P)²+0.8692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1780
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O4(H4a,H4b), O5(H5a,H5b), O7(H7a,H7b), O3(H3a,H3b), O6(H6a,H6b), O8(H8a,H8b)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_disorder_group
O4 O 0.7888(3) 0.4029(5) 0.5314(3) 0.0254(7) Uani 1.000000 . .
H4a H 0.834(4) 0.423(7) 0.486(3) 0.0380(11) Uiso 1.000000 G .
H4b H 0.832(3) 0.314(6) 0.576(3) 0.0380(11) Uiso 1.000000 G .
O5 O 0.9377(3) 0.0754(5) 0.6450(3) 0.0254(7) Uani 1.000000 . .
H5a H 0.881(3) 0.025(8) 0.674(3) 0.0381(11) Uiso 1.000000 G .
H5b H 0.999(3) 0.114(7) 0.6975(19) 0.0381(11) Uiso 1.000000 G .
O11 O 0.5471(3) 0.8743(6) 0.6876(3) 0.0289(7) Uani 1.000000 . .
O7 O 0.0719(3) -0.2206(5) 0.3474(3) 0.0301(8) Uani 1.000000 . .
H7a H 0.051(5) -0.149(5) 0.2897(17) 0.0451(12) Uiso 1.000000 G .
H7b H 0.081(5) -0.139(5) 0.401(2) 0.0451(12) Uiso 1.000000 G .
N11 N 0.1641(6) 0.6907(14) 0.7103(6) 0.070(3) Uani 1.000000 . .
O3 O 0.9266(3) 0.4230(5) 0.3729(3) 0.0279(8) Uani 1.000000 . .
H3a H 0.976(3) 0.320(4) 0.397(4) 0.0419(11) Uiso 1.000000 G .
H3b H 0.977(3) 0.526(4) 0.371(4) 0.0419(11) Uiso 1.000000 G .
O6 O 0.7946(3) 0.7254(5) 0.6730(3) 0.0253(7) Uani 1.000000 . .
H6a H 0.7139(6) 0.739(7) 0.666(4) 0.0380(10) Uiso 1.000000 G .
H6b H 0.835(3) 0.812(6) 0.720(3) 0.0380(10) Uiso 1.000000 G .
O8 O 0.0732(3) 0.1004(5) 0.4879(3) 0.0258(7) Uani 1.000000 . .
H8a H 0.082(5) -0.007(4) 0.451(3) 0.0387(11) Uiso 1.000000 G .
H8b H 0.057(5) 0.050(6) 0.544(2) 0.0387(11) Uiso 1.000000 G .
N10 N 0.1573(4) 0.5794(9) 0.6304(6) 0.0556(18) Uani 1.000000 . 1
O1 O 0.3189(3) -0.3687(6) 0.3362(3) 0.0295(7) Uani 1.000000 . .
O2 O 0.5165(3) -0.4283(6) 0.3367(3) 0.0341(9) Uani 1.000000 . .
O10 O 0.3463(4) 0.9410(7) 0.6868(3) 0.0468(11) Uani 1.000000 . .
N7 N 0.4755(3) 0.5058(7) 0.5792(3) 0.0246(8) Uani 1.000000 . .
N2 N 0.5767(4) 0.1583(7) 0.4729(3) 0.0275(9) Uani 1.000000 . .
N9 N 0.4322(4) 0.8265(7) 0.6678(3) 0.0261(9) Uani 1.000000 . .
N1 N 0.3836(4) -0.0000(7) 0.4422(3) 0.0249(8) Uani 1.000000 . .
N3 N 0.4336(4) -0.3139(7) 0.3552(3) 0.0242(8) Uani 1.000000 . .
N8 N 0.2835(4) 0.3456(7) 0.5501(4) 0.0309(10) Uani 1.000000 . .
C4 C 0.4062(5) 0.3396(8) 0.5391(3) 0.0221(9) Uani 1.000000 . .
C3 C 0.5876(5) -0.0220(8) 0.4212(4) 0.0295(11) Uani 1.000000 . .
C2 C 0.4700(4) -0.1172(8) 0.4039(4) 0.0225(9) Uani 1.000000 . .
C5 C 0.3947(5) 0.6251(8) 0.6203(4) 0.0252(10) Uani 1.000000 . .
N6 N 0.7332(5) -0.2521(7) 0.2566(3) 0.0394(9) Uani 1.000000 . .
C1 C 0.4525(5) 0.1680(8) 0.4861(4) 0.0290(10) Uani 1.000000 . .
C6 C 0.2721(4) 0.5277(8) 0.6035(4) 0.0257(10) Uani 1.000000 . .
N4 N 0.7089(5) -0.0582(8) 0.4045(4) 0.0425(11) Uani 1.000000 . .
N12 N 0.1381(8) 0.7402(18) 0.7548(16) 0.206(9) Uani 1.000000 . .
N5 N 0.7087(4) -0.1662(10) 0.3267(5) 0.0532(16) Uani 1.000000 . .
O9 O 0.0632(4) 0.4983(9) 0.6115(5) 0.0933(18) Uani 1.000000 . -1
H8 H 0.226(3) 0.245(5) 0.527(2) 0.001(7) Uiso 1.000000 . .


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
O11 N9 1.230(5) . ?
N11 N10 1.231(11) . ?
N11 N12 0.76(2) . ?
N10 C6 1.392(7) . ?
O1 N3 1.240(5) . ?
O2 N3 1.212(5) . ?
O10 N9 1.241(5) . ?
N7 C4 1.318(6) . ?
N7 C5 1.348(6) . ?
N2 C3 1.340(7) . ?
N2 C1 1.380(7) . ?
N9 C5 1.429(6) . ?
N1 C2 1.365(7) . ?
N1 C1 1.339(6) . ?
N3 C2 1.406(6) . ?
N8 C4 1.353(6) . ?
N8 C6 1.363(7) . ?
C4 C1 1.432(5) . ?
C3 C2 1.363(7) . ?
C3 N4 1.384(7) . ?
C5 C6 1.416(6) . ?
N6 N5 1.134(8) . ?
N4 N5 1.209(9) . ?

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
N12 N11 N10 154.4(15) . . ?
C6 N10 N11 117.6(6) . . ?
C5 N7 C4 104.4(4) . . ?
C1 N2 C3 107.5(4) . . ?
O10 N9 O11 124.4(4) . . ?
C5 N9 O11 118.1(4) . . ?
C5 N9 O10 117.5(4) . . ?
C1 N1 C2 103.5(4) . . ?
O2 N3 O1 122.0(4) . . ?
C2 N3 O1 119.2(4) . . ?
C2 N3 O2 118.8(4) . . ?
C6 N8 C4 106.5(4) . . ?
N8 C4 N7 113.8(4) . . ?
C1 C4 N7 124.4(3) . . ?
C1 C4 N8 121.8(3) . . ?
C2 C3 N2 105.7(5) . . ?
N4 C3 N2 114.5(5) . . ?
N4 C3 C2 139.8(5) . . ?
N3 C2 N1 120.3(4) . . ?
C3 C2 N1 112.2(5) . . ?
C3 C2 N3 127.5(5) . . ?
N9 C5 N7 121.8(4) . . ?
C6 C5 N7 110.7(4) . . ?
C6 C5 N9 127.4(5) . . ?
N1 C1 N2 111.1(5) . . ?
C4 C1 N2 123.1(3) . . ?
C4 C1 N1 125.8(4) . . ?
N8 C6 N10 121.0(5) . . ?
C5 C6 N10 134.3(5) . . ?
C5 C6 N8 104.6(4) . . ?
N5 N4 C3 114.1(5) . . ?
N4 N5 N6 166.0(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
O11 N9 C5 N7 -12.5(5) . . . . ?
O11 N9 C5 C6 171.4(4) . . . . ?
N11 N10 C6 N8 152.0(5) . . . . ?
N11 N10 C6 C5 -26.9(7) . . . . ?
N10 C6 N8 C4 -178.3(5) . . . . ?
N10 C6 C5 N7 178.8(6) . . . . ?
N10 C6 C5 N9 -4.7(7) . . . . ?
O1 N3 C2 N1 8.2(4) . . . . ?
O1 N3 C2 C3 -173.1(4) . . . . ?
O2 N3 C2 N1 -169.0(4) . . . . ?
O2 N3 C2 C3 9.7(5) . . . . ?
O10 N9 C5 N7 168.0(4) . . . . ?
O10 N9 C5 C6 -8.2(5) . . . . ?
N7 C4 N8 C6 -1.3(5) . . . . ?
N7 C4 C1 N2 0.9(5) . . . . ?
N7 C4 C1 N1 -178.2(3) . . . . ?
N7 C5 C6 N8 -0.3(4) . . . . ?
N2 C3 C2 N1 0.8(4) . . . . ?
N2 C3 C2 N3 -178.0(3) . . . . ?
N2 C3 N4 N5 -152.7(5) . . . . ?
N2 C1 N1 C2 1.6(4) . . . . ?
N2 C1 C4 N8 179.4(2) . . . . ?
N9 C5 C6 N8 176.2(5) . . . . ?
N1 C2 C3 N4 178.6(4) . . . . ?
N1 C1 C4 N8 0.4(6) . . . . ?
N3 C2 C3 N4 -0.2(7) . . . . ?
C3 N4 N5 N6 164.7(11) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
