# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_msc
_database_code_depnum_ccdc_archive 'CCDC 1986345'
_audit_update_record             
;
2020-02-26 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_audit_creation_date             2018-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 N4 O4'
_chemical_formula_sum            'C8 H8 N4 O4'
_chemical_formula_weight         224.18
_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                   6.3611(5)
_cell_length_b                   4.6432(4)
_cell_length_c                   30.859(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.213(3)
_cell_angle_gamma                90
_cell_volume                     908.97(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5002
_cell_measurement_temperature    107(2)
_cell_measurement_theta_max      33.23
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.5559
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       neddle
_exptl_crystal_F_000             464.0
_exptl_crystal_size_max          0.2358
_exptl_crystal_size_mid          0.2158
_exptl_crystal_size_min          0.1898
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            12059
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.547
_diffrn_reflns_theta_min         2.647
_diffrn_ambient_temperature      107.49
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.876
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2509
_reflns_number_total             3397
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.035
_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)+(0.0645P)²+0.8176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1605
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C1(H1), C3(H3A), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O3 O 0.09198(19) 0.6680(3) 0.59128(4) 0.0202(3) Uani 1 1 d . . . . .
O4 O 0.25706(19) 0.4256(2) 0.48847(4) 0.0188(2) Uani 1 1 d . . . . .
O2 O 0.1403(2) -0.1181(3) 0.69691(4) 0.0239(3) Uani 1 1 d . . . . .
O1 O 0.4236(2) -0.1709(3) 0.73962(4) 0.0277(3) Uani 1 1 d . . . . .
N2 N 0.3907(2) 0.7506(3) 0.55721(4) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.5293 0.7454 0.5588 0.022 Uiso 1 1 calc R . . . .
N1 N 0.3230(2) -0.0573(3) 0.70880(5) 0.0186(3) Uani 1 1 d . . . . .
N4 N 0.1522(2) 0.8239(3) 0.44996(5) 0.0189(3) Uani 1 1 d . . . . .
H4A H 0.0663 0.7072 0.4347 0.023 Uiso 1 1 d GR . . . .
H4B H 0.0825 0.9792 0.4569 0.023 Uiso 1 1 d GR . . . .
N3 N 0.2796(2) 0.8656(3) 0.52111(4) 0.0190(3) Uani 1 1 d . . . . .
H3 H 0.2424 1.0482 0.5204 0.023 Uiso 1 1 calc R . . . .
C8 C 0.2289(2) 0.6897(3) 0.48657(5) 0.0158(3) Uani 1 1 d . . . . .
C2 C 0.4292(3) 0.1635(3) 0.68428(5) 0.0164(3) Uani 1 1 d . . . . .
C7 C 0.2835(2) 0.6458(3) 0.59014(5) 0.0161(3) Uani 1 1 d . . . . .
C6 C 0.4152(2) 0.5014(3) 0.62591(5) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.3153(2) 0.2954(3) 0.64999(5) 0.0160(3) Uani 1 1 d . . . . .
H1 H 0.1718 0.2466 0.6430 0.019 Uiso 1 1 calc R . . . .
C3 C 0.6376(3) 0.2312(4) 0.69622(5) 0.0202(3) Uani 1 1 d . . . . .
H3A H 0.7115 0.1387 0.7202 0.024 Uiso 1 1 calc R . . . .
C5 C 0.6260(3) 0.5712(4) 0.63700(5) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.6948 0.7103 0.6204 0.022 Uiso 1 1 calc R . . . .
C4 C 0.7356(3) 0.4381(4) 0.67218(6) 0.0214(3) Uani 1 1 d . . . . .
H4 H 0.8782 0.4890 0.6798 0.026 Uiso 1 1 calc R . . . .


_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
O3 C7 1.226(2) . ?
O4 C8 1.2398(19) . ?
O2 N1 1.2257(19) . ?
O1 N1 1.2257(19) . ?
N2 H2 0.8800 . ?
N2 N3 1.3823(19) . ?
N2 C7 1.355(2) . ?
N1 C2 1.468(2) . ?
N4 H4A 0.8815 . ?
N4 H4B 0.8818 . ?
N4 C8 1.350(2) . ?
N3 H3 0.8800 . ?
N3 C8 1.363(2) . ?
C2 C1 1.381(2) . ?
C2 C3 1.386(2) . ?
C7 C6 1.495(2) . ?
C6 C1 1.393(2) . ?
C6 C5 1.397(2) . ?
C1 H1 0.9500 . ?
C3 H3A 0.9500 . ?
C3 C4 1.389(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.391(2) . ?
C4 H4 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
N3 N2 H2 120.4 . . ?
C7 N2 H2 120.4 . . ?
C7 N2 N3 119.18(14) . . ?
O2 N1 C2 117.94(14) . . ?
O1 N1 O2 124.22(15) . . ?
O1 N1 C2 117.84(14) . . ?
H4A N4 H4B 109.3 . . ?
C8 N4 H4A 109.6 . . ?
C8 N4 H4B 109.3 . . ?
N2 N3 H3 120.8 . . ?
C8 N3 N2 118.44(13) . . ?
C8 N3 H3 120.8 . . ?
O4 C8 N4 122.56(15) . . ?
O4 C8 N3 122.07(15) . . ?
N4 C8 N3 115.34(14) . . ?
C1 C2 N1 118.00(14) . . ?
C1 C2 C3 122.75(15) . . ?
C3 C2 N1 119.25(14) . . ?
O3 C7 N2 123.17(15) . . ?
O3 C7 C6 121.40(14) . . ?
N2 C7 C6 115.43(14) . . ?
C1 C6 C7 116.70(14) . . ?
C1 C6 C5 119.71(15) . . ?
C5 C6 C7 123.53(15) . . ?
C2 C1 C6 118.64(15) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C2 C3 H3A 120.9 . . ?
C2 C3 C4 118.21(15) . . ?
C4 C3 H3A 120.9 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.32(15) . . ?
C4 C5 H5 119.8 . . ?
C3 C4 C5 120.36(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
