# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_20191227-libaosheng-tzy-4no2
_database_code_depnum_ccdc_archive 'CCDC 1974384'
_audit_update_record             
;
2019-12-27 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 Br N4 O3'
_chemical_formula_sum            'C12 H11 Br N4 O3'
_chemical_formula_weight         339.16
_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'
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3703(5)
_cell_length_b                   7.4451(5)
_cell_length_c                   13.4527(8)
_cell_angle_alpha                96.716(5)
_cell_angle_beta                 91.869(5)
_cell_angle_gamma                113.656(6)
_cell_volume                     668.94(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2400
_cell_measurement_temperature    295(2)
_cell_measurement_theta_min      3.5540
_cell_measurement_theta_max      26.7700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.086
_exptl_absorpt_correction_T_min  0.52065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9504
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.027
_diffrn_reflns_theta_min         3.512
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1978
_reflns_number_total             3161
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.982
_refine_diff_density_min         -1.148
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+1.0390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1550
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B), C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00C), C00K(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br01 Br 0.31905(10) -0.38216(9) 0.10428(5) 0.0895(3) Uani 1 1 d . . . . .
O002 O 0.8008(5) -0.1338(5) 0.2145(2) 0.0573(8) Uani 1 1 d . . . . .
N003 N 0.6940(5) 0.1962(5) 0.3577(2) 0.0383(7) Uani 1 1 d . . . . .
N004 N 0.7196(5) 0.1347(5) 0.2648(2) 0.0417(8) Uani 1 1 d . . . . .
O005 O 0.7772(5) 1.0758(5) 0.6950(3) 0.0704(10) Uani 1 1 d . . . . .
O006 O 0.7107(6) 0.8395(6) 0.7844(3) 0.0782(11) Uani 1 1 d . . . . .
N007 N 0.7470(6) 0.9054(6) 0.7052(3) 0.0564(10) Uani 1 1 d . . . . .
N008 N 0.8069(6) 0.2769(5) 0.2088(3) 0.0562(10) Uani 1 1 d . . . . .
C009 C 0.7663(6) 0.5235(6) 0.4529(3) 0.0383(9) Uani 1 1 d . . . . .
C00A C 0.7693(6) 0.3923(6) 0.3627(3) 0.0394(9) Uani 1 1 d . . . . .
C00B C 0.6444(7) -0.0753(6) 0.2249(3) 0.0436(10) Uani 1 1 d . . . . .
H00B H 0.5538 -0.1535 0.2706 0.052 Uiso 1 1 calc R . . . .
C00C C 0.7562(6) 0.7720(6) 0.6179(3) 0.0449(10) Uani 1 1 d . . . . .
C00D C 0.7396(6) 0.4598(6) 0.5463(3) 0.0458(10) Uani 1 1 d . . . . .
H00D H 0.7249 0.3319 0.5529 0.055 Uiso 1 1 calc R . . . .
C00E C 0.7895(6) 0.7144(6) 0.4442(3) 0.0477(10) Uani 1 1 d . . . . .
H00E H 0.8107 0.7589 0.3821 0.057 Uiso 1 1 calc R . . . .
C00F C 0.7818(7) 0.8401(6) 0.5263(3) 0.0512(11) Uani 1 1 d . . . . .
H00F H 0.7936 0.9673 0.5199 0.061 Uiso 1 1 calc R . . . .
C00G C 0.7347(7) 0.5849(6) 0.6298(3) 0.0490(10) Uani 1 1 d . . . . .
H00G H 0.7173 0.5427 0.6926 0.059 Uiso 1 1 calc R . . . .
C00H C 0.5361(7) -0.1181(7) 0.1213(3) 0.0517(11) Uani 1 1 d . . . . .
H00H H 0.4861 -0.0172 0.1114 0.062 Uiso 1 1 calc R . . . .
C00I C 0.8400(8) 0.4410(7) 0.2704(3) 0.0549(11) Uani 1 1 d . . . . .
H00I H 0.9009 0.5690 0.2546 0.066 Uiso 1 1 calc R . . . .
C00J C 0.6940(8) -0.1108(8) 0.0515(3) 0.0624(13) Uani 1 1 d . . . . .
H00A H 0.6364 -0.1973 -0.0114 0.075 Uiso 1 1 calc R . . . .
H00C H 0.7689 0.0230 0.0377 0.075 Uiso 1 1 calc R . . . .
C00K C 0.8232(10) -0.1827(10) 0.1101(4) 0.0801(17) Uani 1 1 d . . . . .
H00J H 0.7804 -0.3246 0.0926 0.096 Uiso 1 1 calc R . . . .
H00K H 0.9610 -0.1174 0.0961 0.096 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
Br01 C00H 1.955(5) . ?
O002 C00B 1.391(5) . ?
O002 C00K 1.441(5) . ?
N003 N004 1.326(4) . ?
N003 C00A 1.330(5) . ?
N004 N008 1.331(5) . ?
N004 C00B 1.459(5) . ?
O005 N007 1.222(5) . ?
O006 N007 1.218(5) . ?
N007 C00C 1.468(5) . ?
N008 C00I 1.323(5) . ?
C009 C00A 1.472(5) . ?
C009 C00D 1.387(6) . ?
C009 C00E 1.381(6) . ?
C00A C00I 1.393(6) . ?
C00B H00B 0.9800 . ?
C00B C00H 1.517(6) . ?
C00C C00F 1.377(6) . ?
C00C C00G 1.367(6) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.384(5) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.380(6) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9800 . ?
C00H C00J 1.507(7) . ?
C00I H00I 0.9300 . ?
C00J H00A 0.9700 . ?
C00J H00C 0.9700 . ?
C00J C00K 1.507(7) . ?
C00K H00J 0.9700 . ?
C00K H00K 0.9700 . ?

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
C00B O002 C00K 111.0(3) . . ?
N004 N003 C00A 103.7(3) . . ?
N003 N004 N008 115.6(3) . . ?
N003 N004 C00B 121.9(3) . . ?
N008 N004 C00B 122.4(3) . . ?
O005 N007 C00C 118.7(4) . . ?
O006 N007 O005 123.6(4) . . ?
O006 N007 C00C 117.7(4) . . ?
C00I N008 N004 103.2(3) . . ?
C00D C009 C00A 121.6(4) . . ?
C00E C009 C00A 119.3(4) . . ?
C00E C009 C00D 119.1(4) . . ?
N003 C00A C009 122.6(4) . . ?
N003 C00A C00I 108.2(3) . . ?
C00I C00A C009 129.1(4) . . ?
O002 C00B N004 110.4(4) . . ?
O002 C00B H00B 109.5 . . ?
O002 C00B C00H 106.7(3) . . ?
N004 C00B H00B 109.5 . . ?
N004 C00B C00H 111.3(3) . . ?
C00H C00B H00B 109.5 . . ?
C00F C00C N007 118.2(4) . . ?
C00G C00C N007 119.2(4) . . ?
C00G C00C C00F 122.6(4) . . ?
C009 C00D H00D 119.7 . . ?
C00G C00D C009 120.7(4) . . ?
C00G C00D H00D 119.7 . . ?
C009 C00E H00E 119.5 . . ?
C00F C00E C009 121.1(4) . . ?
C00F C00E H00E 119.5 . . ?
C00C C00F C00E 118.1(4) . . ?
C00C C00F H00F 120.9 . . ?
C00E C00F H00F 120.9 . . ?
C00C C00G C00D 118.4(4) . . ?
C00C C00G H00G 120.8 . . ?
C00D C00G H00G 120.8 . . ?
Br01 C00H H00H 111.0 . . ?
C00B C00H Br01 109.3(3) . . ?
C00B C00H H00H 111.0 . . ?
C00J C00H Br01 111.0(3) . . ?
C00J C00H C00B 103.4(4) . . ?
C00J C00H H00H 111.0 . . ?
N008 C00I C00A 109.4(4) . . ?
N008 C00I H00I 125.3 . . ?
C00A C00I H00I 125.3 . . ?
C00H C00J H00A 111.2 . . ?
C00H C00J H00C 111.2 . . ?
H00A C00J H00C 109.1 . . ?
C00K C00J C00H 102.8(4) . . ?
C00K C00J H00A 111.2 . . ?
C00K C00J H00C 111.2 . . ?
O002 C00K C00J 105.9(4) . . ?
O002 C00K H00J 110.6 . . ?
O002 C00K H00K 110.6 . . ?
C00J C00K H00J 110.6 . . ?
C00J C00K H00K 110.6 . . ?
H00J C00K H00K 108.7 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
