# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_3e
_database_code_depnum_ccdc_archive 'CCDC 2084686'
loop_
_audit_author_name
_audit_author_address
'Lucjan B. Jerzykiewicz'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2021-05-19 deposited with the CCDC.	2021-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 N5 O2, Br'
_chemical_formula_sum            'C7 H10 Br N5 O2'
_chemical_formula_weight         276.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2177(2)
_cell_length_b                   6.76340(10)
_cell_length_c                   11.0057(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.445(2)
_cell_angle_gamma                90
_cell_volume                     1068.13(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17951
_cell_measurement_theta_min      3.0630
_cell_measurement_theta_max      75.1110

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    5.209
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.75a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            25170
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.080
_diffrn_reflns_theta_max         75.438
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2189
_reflns_number_gt                2115
_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       'CrysAlisPro 1.171.41.75a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.75a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2014)'
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0305P)²+0.4669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2189
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0545
_refine_ls_wR_factor_gt          0.0541
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
Br1 Br 0.18012(2) 0.49065(2) -0.03214(2) 0.01565(7) Uani 1 1 d . . . . .
N11 N 0.07453(9) 0.50175(15) 0.39033(13) 0.0151(3) Uani 1 1 d . . . . .
N12 N 0.15711(9) 0.50597(14) 0.49468(13) 0.0129(3) Uani 1 1 d . . . . .
N13 N 0.05594(11) 0.5240(2) 0.16822(14) 0.0238(3) Uani 1 1 d . . . . .
N21 N 0.47620(8) 0.62588(18) 0.60567(11) 0.0185(2) Uani 1 1 d . . . . .
N22 N 0.34677(9) 0.26646(19) 0.70302(13) 0.0205(3) Uani 1 1 d . . . . .
O11 O 0.19979(8) 0.52315(14) 0.32760(11) 0.0151(2) Uani 1 1 d . . . . .
O21 O 0.46171(7) 0.47302(15) 0.68819(11) 0.0182(2) Uani 1 1 d . . . . .
C11 C 0.22977(11) 0.51528(18) 0.45739(15) 0.0141(3) Uani 1 1 d . . . . .
C12 C 0.10382(10) 0.51541(19) 0.29246(15) 0.0157(3) Uani 1 1 d . . . . .
C13 C 0.15297(12) 0.50637(19) 0.62511(16) 0.0182(3) Uani 1 1 d . . . . .
H13A H 0.095866 0.573043 0.625423 0.039(5) Uiso 1 1 calc R . . . .
H13B H 0.207285 0.576464 0.682632 0.043(6) Uiso 1 1 calc R . . . .
H13C H 0.152964 0.369859 0.654971 0.040(5) Uiso 1 1 calc R . . . .
C21 C 0.32689(10) 0.5208(2) 0.53125(14) 0.0152(3) Uani 1 1 d . . . . .
C22 C 0.39669(9) 0.6486(2) 0.51390(13) 0.0159(3) Uani 1 1 d . . . . .
C23 C 0.37282(9) 0.4116(2) 0.64040(13) 0.0159(3) Uani 1 1 d . . . . .
C24 C 0.38816(10) 0.7933(2) 0.40906(14) 0.0211(3) Uani 1 1 d . . . . .
H24A H 0.448270 0.858818 0.423890 0.032 Uiso 1 1 calc R U . . .
H24B H 0.340911 0.892318 0.408028 0.032 Uiso 1 1 calc R U . . .
H24C H 0.369681 0.724173 0.326089 0.032 Uiso 1 1 calc R U . . .
H1 H 0.0842(17) 0.516(3) 0.115(2) 0.029(6) Uiso 1 1 d . . . . .
H2 H -0.0023(17) 0.520(2) 0.146(2) 0.025(5) Uiso 1 1 d . . . . .
H3 H 0.3898(14) 0.213(3) 0.763(2) 0.032(5) Uiso 1 1 d . . . . .
H4 H 0.3022(14) 0.196(3) 0.6598(19) 0.031(5) 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
N11 C12 1.299(2) . ?
N11 N12 1.3921(18) . ?
N12 C11 1.303(2) . ?
N12 C13 1.458(2) . ?
N13 C12 1.319(2) . ?
N13 H1 0.83(3) . ?
N13 H2 0.84(2) . ?
N21 C22 1.3015(18) . ?
N21 O21 1.4407(16) . ?
N22 C23 1.3333(19) . ?
N22 H3 0.84(2) . ?
N22 H4 0.83(2) . ?
O11 C11 1.3481(19) . ?
O11 C12 1.3818(18) . ?
O21 C23 1.3436(17) . ?
C11 C21 1.431(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 C23 1.3848(19) . ?
C21 C22 1.431(2) . ?
C22 C24 1.4854(19) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C12 N11 N12 102.59(13) . . ?
C11 N12 N11 111.64(14) . . ?
C11 N12 C13 129.02(14) . . ?
N11 N12 C13 119.30(13) . . ?
C12 N13 H1 119.1(17) . . ?
C12 N13 H2 117.7(15) . . ?
H1 N13 H2 122(2) . . ?
C22 N21 O21 106.02(11) . . ?
C23 N22 H3 115.9(13) . . ?
C23 N22 H4 116.6(13) . . ?
H3 N22 H4 118.2(19) . . ?
C11 O11 C12 104.39(12) . . ?
C23 O21 N21 108.69(10) . . ?
N12 C11 O11 108.20(13) . . ?
N12 C11 C21 130.31(15) . . ?
O11 C11 C21 121.48(13) . . ?
N11 C12 N13 129.72(15) . . ?
N11 C12 O11 113.14(13) . . ?
N13 C12 O11 117.13(14) . . ?
N12 C13 H13A 109.5 . . ?
N12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C23 C21 C11 127.35(14) . . ?
C23 C21 C22 104.78(12) . . ?
C11 C21 C22 127.76(13) . . ?
N21 C22 C21 111.40(12) . . ?
N21 C22 C24 119.91(12) . . ?
C21 C22 C24 128.68(12) . . ?
N22 C23 O21 117.33(12) . . ?
N22 C23 C21 133.62(13) . . ?
O21 C23 C21 109.05(12) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
C12 N11 N12 C11 -1.93(13) . . . . ?
C12 N11 N12 C13 176.10(11) . . . . ?
C22 N21 O21 C23 0.02(14) . . . . ?
N11 N12 C11 O11 1.64(13) . . . . ?
C13 N12 C11 O11 -176.15(11) . . . . ?
N11 N12 C11 C21 -179.43(13) . . . . ?
C13 N12 C11 C21 2.8(2) . . . . ?
C12 O11 C11 N12 -0.65(13) . . . . ?
C12 O11 C11 C21 -179.69(12) . . . . ?
N12 N11 C12 N13 -177.98(14) . . . . ?
N12 N11 C12 O11 1.50(13) . . . . ?
C11 O11 C12 N11 -0.61(14) . . . . ?
C11 O11 C12 N13 178.94(12) . . . . ?
N12 C11 C21 C23 41.3(2) . . . . ?
O11 C11 C21 C23 -139.88(14) . . . . ?
N12 C11 C21 C22 -134.27(15) . . . . ?
O11 C11 C21 C22 44.5(2) . . . . ?
O21 N21 C22 C21 1.44(15) . . . . ?
O21 N21 C22 C24 -178.33(12) . . . . ?
C23 C21 C22 N21 -2.33(16) . . . . ?
C11 C21 C22 N21 174.04(14) . . . . ?
C23 C21 C22 C24 177.41(13) . . . . ?
C11 C21 C22 C24 -6.2(2) . . . . ?
N21 O21 C23 N22 178.65(11) . . . . ?
N21 O21 C23 C21 -1.50(15) . . . . ?
C11 C21 C23 N22 5.7(3) . . . . ?
C22 C21 C23 N22 -177.92(15) . . . . ?
C11 C21 C23 O21 -174.13(13) . . . . ?
C22 C21 C23 O21 2.26(15) . . . . ?

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
_geom_hbond_publ_flag
N13 H1 Br1 0.83(3) 2.52(3) 3.3555(16) 176(2) . yes
N13 H2 Br1 0.84(2) 2.58(2) 3.4024(15) 168.5(19) 3_565 yes
N22 H3 N21 0.84(2) 2.15(2) 2.9696(17) 163.7(18) 2_646 yes
N22 H4 Br1 0.83(2) 2.63(2) 3.4327(13) 162.8(17) 4_566 yes

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.069

