# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_P2(1)_N_a
_database_code_depnum_ccdc_archive 'CCDC 2336974'
loop_
_audit_author_name
_audit_author_address
'Dong Won Kang'
;Inhav University
South Korea
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        (H2dobpdc)(GuaH)2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N6 O6'
_chemical_formula_sum            'C16 H20 N6 O6'
_chemical_formula_weight         392.38

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 0.0064 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.8040(10)
_cell_length_b                   18.247(4)
_cell_length_c                   9.818(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.00(3)
_cell_angle_gamma                90
_cell_volume                     835.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           ?
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7449
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         33.446
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2859
_reflns_number_gt                2750
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1703P)²+0.2142P] 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-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.31(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2859
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2481
_refine_ls_wR_factor_gt          0.2449
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.001
_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
O1 O 0.3870(2) 0.68503(5) 0.08595(9) 0.0184(3) Uani 1 1 d . . . . .
N1 N 0.1035(2) 0.78248(6) 0.34886(10) 0.0181(3) Uani 1 1 d . . . . .
H1A H 0.245677 0.754270 0.338639 0.022 Uiso 1 1 calc R U . . .
H1B H 0.071525 0.788878 0.432601 0.022 Uiso 1 1 calc R U . . .
C1 C -0.0614(2) 0.81515(6) 0.23874(12) 0.0153(3) Uani 1 1 d . . . . .
O2 O 0.52629(19) 0.68513(5) 0.32004(9) 0.0186(3) Uani 1 1 d . . . . .
N2 N -0.2702(2) 0.86044(6) 0.25524(11) 0.0199(3) Uani 1 1 d . . . . .
H2A H -0.297215 0.868358 0.339533 0.024 Uiso 1 1 calc R U . . .
H2B H -0.380470 0.882273 0.181792 0.024 Uiso 1 1 calc R U . . .
C2 C 0.5409(2) 0.66139(6) 0.19929(12) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.7619(2) 0.60309(6) 0.19900(11) 0.0145(3) Uani 1 1 d . . . . .
O3 O 0.9500(2) 0.61369(5) 0.44936(9) 0.0196(3) Uani 1 1 d . . . . .
H3C H 0.818488 0.645121 0.436812 0.024 Uiso 1 1 calc R U . . .
N3 N -0.0127(2) 0.80542(6) 0.11184(11) 0.0186(3) Uani 1 1 d . . . . .
H3A H 0.129426 0.777208 0.101675 0.022 Uiso 1 1 calc R U . . .
H3B H -0.122790 0.827219 0.038298 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7812(2) 0.56933(6) 0.07396(11) 0.0154(3) Uani 1 1 d . . . . .
H4 H 0.647180 0.582664 -0.010465 0.018 Uiso 1 1 calc R U . . .
C5 C 0.9893(2) 0.51680(6) 0.06782(11) 0.0146(3) Uani 1 1 d . . . . .
C6 C 1.1810(3) 0.49769(7) 0.19542(12) 0.0176(3) Uani 1 1 d . . . . .
H6 H 1.326675 0.462511 0.195179 0.021 Uiso 1 1 calc R U . . .
C7 C 1.1620(3) 0.52907(7) 0.32141(12) 0.0183(3) Uani 1 1 d . . . . .
H7 H 1.290703 0.514166 0.406363 0.022 Uiso 1 1 calc R U . . .
C8 C 0.9555(2) 0.58233(6) 0.32451(12) 0.0158(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2542(14) . ?
N1 C1 1.3182(15) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
C1 N3 1.3339(15) . ?
C1 N2 1.3396(15) . ?
O2 C2 1.2800(13) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C2 C3 1.5035(16) . ?
C3 C4 1.3964(15) . ?
C3 C8 1.4043(16) . ?
O3 C8 1.3588(14) . ?
O3 H3C 0.8400 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C4 C5 1.3967(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.4075(17) . ?
C5 C5 1.492(2) 3_765 ?
C6 C7 1.3860(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3943(16) . ?
C7 H7 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
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C1 N3 119.97(11) . . ?
N1 C1 N2 119.93(11) . . ?
N3 C1 N2 120.04(11) . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O1 C2 O2 123.55(11) . . ?
O1 C2 C3 120.45(10) . . ?
O2 C2 C3 116.00(10) . . ?
C4 C3 C8 118.80(10) . . ?
C4 C3 C2 120.72(10) . . ?
C8 C3 C2 120.47(10) . . ?
C8 O3 H3C 109.5 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C3 C4 C5 122.75(11) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C4 C5 C6 116.92(10) . . ?
C4 C5 C5 121.69(12) . 3_765 ?
C6 C5 C5 121.39(12) . 3_765 ?
C7 C6 C5 121.45(11) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.55(11) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
O3 C8 C7 118.84(10) . . ?
O3 C8 C3 121.65(10) . . ?
C7 C8 C3 119.50(10) . . ?

_refine_diff_density_max         0.673
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.115


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
_exptl_crystal_preparation       'hydrogen storage'
