# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_2PyMIGHBr
_database_code_depnum_ccdc_archive 'CCDC 2160087'
loop_
_audit_author_name
_audit_author_address
'Jeffrey D. Einkauf'
;Oak Ridge National Laboratory
United States of America
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2024-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            2PyMIGHBr
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H10 Br N5'
_chemical_formula_weight         244.11

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   11.057
_cell_length_b                   10.978
_cell_length_c                   7.917
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     961.0
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    34281
_cell_measurement_theta_min      2.614
_cell_measurement_theta_max      30.556

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   0.429
_exptl_transmission_factor_max   0.816
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.239
_shelx_estimated_absorpt_T_min   0.429
_shelx_estimated_absorpt_T_max   0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       single
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34281
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.614
_diffrn_reflns_theta_max         30.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2923
_reflns_number_gt                2819
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.979

_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    ?
_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)+(0.0135P)²+0.2789P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2923
_refine_ls_number_parameters     118
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0427
_refine_ls_wR_factor_gt          0.0422
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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 0.49425(2) 0.19314(2) 0.16837(8) 0.01374(6) Uani 1 1 d . . . . .
C7 C 0.75299(16) 0.40628(16) 0.8476(2) 0.0123(3) Uani 1 1 d . . . . .
N2 N 0.71314(15) 0.49096(14) 0.58554(19) 0.0132(3) Uani 1 1 d . . . . .
C2 C 0.73703(19) 0.68100(17) 0.0157(2) 0.0173(4) Uani 1 1 d . . . . .
H2 H 0.756109 0.718304 -0.089254 0.021 Uiso 1 1 calc R U . . .
C1 C 0.61804(18) 0.66820(17) 0.0671(2) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.556052 0.696648 -0.006064 0.019 Uiso 1 1 calc R U . . .
C5 C 0.67425(16) 0.57848(16) 0.3175(2) 0.0123(3) Uani 1 1 d . . . . .
C6 C 0.63447(16) 0.52568(17) 0.4781(2) 0.0130(3) Uani 1 1 d . . . . .
H6 H 0.550676 0.517378 0.502047 0.016 Uiso 1 1 calc R U . . .
N5 N 0.71769(14) 0.34820(15) 0.9855(2) 0.0150(3) Uani 1 1 d . . . . .
H5A H 0.771173 0.327012 1.062368 0.018 Uiso 1 1 calc R U . . .
H5B H 0.640737 0.330770 1.000290 0.018 Uiso 1 1 calc R U . . .
N3 N 0.66988(14) 0.43977(14) 0.7309(2) 0.0132(3) Uani 1 1 d . . . . .
H3 H 0.591933 0.429124 0.747829 0.016 Uiso 1 1 calc R U . . .
N4 N 0.86852(14) 0.43318(15) 0.8234(2) 0.0144(3) Uani 1 1 d . . . . .
H4A H 0.922732 0.412403 0.899503 0.017 Uiso 1 1 calc R U . . .
H4B H 0.891044 0.471829 0.731227 0.017 Uiso 1 1 calc R U . . .
N1 N 0.58553(14) 0.61765(14) 0.21490(19) 0.0139(3) Uani 1 1 d . . . . .
C3 C 0.82784(17) 0.63805(18) 0.1211(2) 0.0174(4) Uani 1 1 d . . . . .
H3A H 0.910319 0.644411 0.088688 0.021 Uiso 1 1 calc R U . . .
C4 C 0.79678(17) 0.58606(18) 0.2735(2) 0.0158(3) Uani 1 1 d . . . . .
H4 H 0.857409 0.555872 0.347501 0.019 Uiso 1 1 calc R U . . .


_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
C7 N5 1.323(2) . ?
C7 N4 1.325(2) . ?
C7 N3 1.354(2) . ?
N2 C6 1.275(2) . ?
N2 N3 1.367(2) . ?
C2 C1 1.384(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C1 N1 1.344(2) . ?
C1 H1 0.9500 . ?
C5 N1 1.344(2) . ?
C5 C4 1.401(2) . ?
C5 C6 1.465(3) . ?
C6 H6 0.9500 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N3 H3 0.8800 . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C3 C4 1.378(3) . ?
C3 H3A 0.9500 . ?
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
N5 C7 N4 120.72(17) . . ?
N5 C7 N3 119.57(16) . . ?
N4 C7 N3 119.70(17) . . ?
C6 N2 N3 116.48(15) . . ?
C1 C2 C3 118.44(17) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
N1 C1 C2 123.50(17) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N1 C5 C4 122.46(17) . . ?
N1 C5 C6 115.58(16) . . ?
C4 C5 C6 121.96(16) . . ?
N2 C6 C5 119.50(16) . . ?
N2 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C7 N3 N2 116.64(15) . . ?
C7 N3 H3 121.7 . . ?
N2 N3 H3 121.7 . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C5 N1 C1 117.57(16) . . ?
C4 C3 C2 119.13(18) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 118.88(17) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.075

