# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1960812'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H7 N3), H2 O2'
_chemical_formula_sum            'C14 H16 N6 O2'
_chemical_formula_weight         300.33

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   9.5406(14)
_cell_length_b                   9.1665(13)
_cell_length_c                   15.890(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1389.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6690
_cell_measurement_theta_min      2.564
_cell_measurement_theta_max      30.529

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14321
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_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         2.56
_diffrn_reflns_theta_max         30.00
_reflns_number_total             2033
_reflns_number_gt                1833
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0601P)²+0.4733P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2033
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.73493(9) 0.15622(9) 0.73621(5) 0.01747(18) Uani 1 1 d . . .
H11 H 0.7125(16) 0.2323(17) 0.7667(10) 0.030(4) Uiso 1 1 d . . .
H12 H 0.8010(16) 0.0951(17) 0.7536(9) 0.027(4) Uiso 1 1 d . . .
N2 N 0.61757(8) 0.26248(8) 0.61983(5) 0.01356(17) Uani 1 1 d . . .
N3 N 0.73080(8) 0.05007(8) 0.59965(5) 0.01347(17) Uani 1 1 d . . .
H3 H 0.7778(15) -0.0309(16) 0.6124(9) 0.024(3) Uiso 1 1 d . . .
C1 C 0.69528(9) 0.15752(9) 0.65487(5) 0.01310(18) Uani 1 1 d . . .
C2 C 0.60049(9) 0.21857(9) 0.53607(5) 0.01264(18) Uani 1 1 d . . .
C3 C 0.67134(9) 0.08628(9) 0.52227(5) 0.01272(18) Uani 1 1 d . . .
C4 C 0.67366(9) 0.01819(10) 0.44428(6) 0.01591(19) Uani 1 1 d . . .
C5 C 0.60160(10) 0.08768(10) 0.37914(6) 0.01692(19) Uani 1 1 d . . .
C6 C 0.53027(9) 0.21933(10) 0.39217(6) 0.01624(19) Uani 1 1 d . . .
C7 C 0.52800(9) 0.28607(10) 0.47095(6) 0.01481(19) Uani 1 1 d . . .
H4 H 0.7207(14) -0.0733(15) 0.4356(9) 0.021(3) Uiso 1 1 d . . .
H5 H 0.5987(15) 0.0434(15) 0.3228(9) 0.028(4) Uiso 1 1 d . . .
H6 H 0.4812(15) 0.2629(14) 0.3442(9) 0.023(3) Uiso 1 1 d . . .
H7 H 0.4771(14) 0.3759(15) 0.4807(8) 0.022(3) Uiso 1 1 d . . .
O1 O 0.45135(8) 0.43538(8) 0.71395(4) 0.02034(18) Uani 1 1 d . . .
H1 H 0.5042(17) 0.3782(18) 0.6782(10) 0.035(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
N1 C1 1.3468(12) . ?
N1 H11 0.876(16) . ?
N1 H12 0.888(16) . ?
N2 C1 1.3361(11) . ?
N2 C2 1.4002(11) . ?
N3 C1 1.3620(11) . ?
N3 C3 1.3942(11) . ?
N3 H3 0.891(15) . ?
C2 C7 1.3898(12) . ?
C2 C3 1.4055(12) . ?
C3 C4 1.3878(12) . ?
C4 C5 1.3964(13) . ?
C4 H4 0.961(13) . ?
C5 C6 1.4008(13) . ?
C5 H5 0.983(15) . ?
C6 C7 1.3935(13) . ?
C6 H6 0.980(14) . ?
C7 H7 0.969(14) . ?
O1 O1 1.4747(14) 3_656 ?
O1 H1 0.923(16) . ?

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 H11 117.1(10) . . ?
C1 N1 H12 120.3(10) . . ?
H11 N1 H12 120.2(14) . . ?
C1 N2 C2 104.70(7) . . ?
C1 N3 C3 107.15(7) . . ?
C1 N3 H3 125.6(9) . . ?
C3 N3 H3 127.1(9) . . ?
N2 C1 N1 124.21(8) . . ?
N2 C1 N3 112.98(8) . . ?
N1 C1 N3 122.82(8) . . ?
C7 C2 N2 129.62(8) . . ?
C7 C2 C3 120.48(8) . . ?
N2 C2 C3 109.90(7) . . ?
C4 C3 N3 132.38(8) . . ?
C4 C3 C2 122.34(8) . . ?
N3 C3 C2 105.28(7) . . ?
C3 C4 C5 116.68(8) . . ?
C3 C4 H4 121.8(8) . . ?
C5 C4 H4 121.5(8) . . ?
C4 C5 C6 121.51(8) . . ?
C4 C5 H5 120.0(8) . . ?
C6 C5 H5 118.5(8) . . ?
C7 C6 C5 121.23(8) . . ?
C7 C6 H6 120.9(8) . . ?
C5 C6 H6 117.9(8) . . ?
C2 C7 C6 117.75(8) . . ?
C2 C7 H7 120.6(8) . . ?
C6 C7 H7 121.6(8) . . ?
O1 O1 H1 97.7(10) 3_656 . ?

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
H1 O1 O1 H1 -110(2) . . 3_656 3_656 ?

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
O1 H1 N2 0.923(16) 1.776(16) 2.6951(10) 173.3(15) .
N3 H3 N2 0.891(15) 2.144(15) 3.0241(11) 169.5(13) 8_755
N1 H11 O1 0.876(16) 2.450(16) 3.2147(12) 146.1(13) 3_656
N1 H12 O1 0.888(16) 2.113(16) 2.9980(11) 174.4(14) 6_657

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.049
