# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_11
_database_code_depnum_ccdc_archive 'CCDC 2388555'
loop_
_audit_author_name
_audit_author_address
liuping
;Shihezi University
China
;
_audit_update_record             
;
2024-10-03 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_audit_creation_date             2024-09-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H7 Br N2'
_chemical_formula_sum            'C11 H7 Br N2'
_chemical_formula_weight         247.10
_chemical_absolute_configuration ?
_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 0.0181 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'
Br Br -0.6763 1.2805 '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'

_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.4291(6)
_cell_length_b                   4.1088(2)
_cell_length_c                   16.6768(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     920.18(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      71.99
_cell_measurement_theta_min      6.59
_shelx_estimated_absorpt_T_max   0.658
_shelx_estimated_absorpt_T_min   0.426
_exptl_absorpt_coefficient_mu    5.712
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.5195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1154 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.5991.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17823
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.037
_diffrn_reflns_theta_min         5.305
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                1696
_reflns_number_total             1791
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.21(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1791
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.053
_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)+(0.0206P)²+1.1447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0659
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.79(4)
 0.21(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10)
;
_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
Br1 Br 0.55886(3) 0.19653(11) 0.30291(4) 0.03268(17) Uani 1 1 d . . . . .
N1 N 0.6855(3) 0.6180(10) 0.4968(3) 0.0228(9) Uani 1 1 d . . . . .
N2 N 0.4931(3) 0.8454(12) 0.5331(3) 0.0276(10) Uani 1 1 d . . . . .
C1 C 0.6389(4) 0.3575(13) 0.3858(3) 0.0280(11) Uani 1 1 d . . . . .
C2 C 0.7421(4) 0.3182(14) 0.3956(3) 0.0296(11) Uani 1 1 d . . . . .
H2 H 0.785460 0.201634 0.360918 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7689(4) 0.4796(15) 0.4647(3) 0.0278(12) Uani 1 1 d . . . . .
H3 H 0.834280 0.492345 0.486351 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6731(4) 0.8162(12) 0.5645(3) 0.0226(10) Uani 1 1 d . . . . .
C5 C 0.7519(4) 0.9041(14) 0.6139(3) 0.0275(12) Uani 1 1 d . . . . .
H5 H 0.817482 0.832105 0.602160 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7345(4) 1.0952(15) 0.6798(4) 0.0322(13) Uani 1 1 d . . . . .
H6 H 0.788195 1.151326 0.714217 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6381(4) 1.2091(13) 0.6972(3) 0.0309(12) Uani 1 1 d . . . . .
H7 H 0.626791 1.342406 0.742831 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5603(4) 1.1257(13) 0.6473(3) 0.0278(11) Uani 1 1 d . . . . .
H8 H 0.495345 1.205185 0.658588 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5753(4) 0.9260(13) 0.5805(3) 0.0239(10) Uani 1 1 d . . . . .
C10 C 0.5091(3) 0.6633(13) 0.4712(3) 0.0262(10) Uani 1 1 d . . . . .
H10 H 0.453552 0.607085 0.438713 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6036(4) 0.5422(12) 0.4484(3) 0.0236(10) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0400(3) 0.0325(3) 0.0256(2) -0.0017(4) -0.0077(3) -0.0020(2)
N1 0.0209(19) 0.025(2) 0.023(2) 0.0025(16) -0.0020(15) -0.0016(16)
N2 0.021(2) 0.035(3) 0.027(2) 0.0006(18) -0.0010(16) -0.0027(18)
C1 0.031(3) 0.030(3) 0.023(3) 0.003(2) -0.001(2) 0.000(2)
C2 0.030(3) 0.032(3) 0.027(3) 0.001(2) 0.003(2) 0.002(2)
C3 0.024(2) 0.034(3) 0.025(3) 0.001(2) -0.001(2) 0.002(2)
C4 0.026(2) 0.025(2) 0.017(2) 0.0040(19) 0.0008(18) -0.0005(19)
C5 0.026(3) 0.029(3) 0.028(3) 0.006(2) -0.003(2) -0.005(2)
C6 0.037(3) 0.035(3) 0.024(3) 0.003(2) -0.008(2) -0.004(3)
C7 0.044(3) 0.028(3) 0.021(3) -0.001(2) 0.002(2) -0.002(2)
C8 0.029(3) 0.031(3) 0.024(3) 0.006(2) 0.005(2) 0.002(2)
C9 0.025(2) 0.025(2) 0.021(2) 0.003(2) -0.0015(18) -0.0033(19)
C10 0.018(2) 0.035(3) 0.026(3) 0.004(2) -0.0033(19) -0.002(2)
C11 0.025(2) 0.022(2) 0.024(2) 0.0050(19) -0.0023(18) 0.000(2)

_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
Br1 C1 1.871(5) . ?
N1 C3 1.366(7) . ?
N1 C4 1.401(7) . ?
N1 C11 1.401(6) . ?
N2 C9 1.398(6) . ?
N2 C10 1.294(7) . ?
C1 C2 1.405(8) . ?
C1 C11 1.375(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(7) . ?
C4 C9 1.415(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.371(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.406(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.398(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.415(7) . ?

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
C3 N1 C4 130.9(4) . . ?
C3 N1 C11 109.0(4) . . ?
C4 N1 C11 120.0(4) . . ?
C10 N2 C9 117.2(4) . . ?
C2 C1 Br1 127.7(4) . . ?
C11 C1 Br1 123.9(4) . . ?
C11 C1 C2 108.4(5) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 C1 107.5(5) . . ?
C3 C2 H2 126.3 . . ?
N1 C3 C2 108.3(5) . . ?
N1 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
N1 C4 C9 116.6(4) . . ?
C5 C4 N1 122.6(5) . . ?
C5 C4 C9 120.8(5) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.7(5) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.8(5) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(5) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.1(5) . . ?
C9 C8 H8 119.4 . . ?
N2 C9 C4 123.4(5) . . ?
N2 C9 C8 118.4(4) . . ?
C8 C9 C4 118.2(5) . . ?
N2 C10 H10 117.7 . . ?
N2 C10 C11 124.5(5) . . ?
C11 C10 H10 117.7 . . ?
N1 C11 C10 118.1(5) . . ?
C1 C11 N1 106.8(4) . . ?
C1 C11 C10 135.0(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
Br1 C1 C2 C3 179.7(4) . . . . ?
Br1 C1 C11 N1 -179.3(4) . . . . ?
Br1 C1 C11 C10 -0.1(9) . . . . ?
N1 C4 C5 C6 -179.1(5) . . . . ?
N1 C4 C9 N2 0.3(7) . . . . ?
N1 C4 C9 C8 -179.7(5) . . . . ?
N2 C10 C11 N1 1.3(8) . . . . ?
N2 C10 C11 C1 -177.8(6) . . . . ?
C1 C2 C3 N1 -0.5(7) . . . . ?
C2 C1 C11 N1 0.2(6) . . . . ?
C2 C1 C11 C10 179.5(6) . . . . ?
C3 N1 C4 C5 -1.1(9) . . . . ?
C3 N1 C4 C9 178.7(5) . . . . ?
C3 N1 C11 C1 -0.6(6) . . . . ?
C3 N1 C11 C10 -179.9(5) . . . . ?
C4 N1 C3 C2 -177.3(5) . . . . ?
C4 N1 C11 C1 177.6(4) . . . . ?
C4 N1 C11 C10 -1.7(7) . . . . ?
C4 C5 C6 C7 -1.3(9) . . . . ?
C5 C4 C9 N2 -179.9(5) . . . . ?
C5 C4 C9 C8 0.1(7) . . . . ?
C5 C6 C7 C8 0.3(9) . . . . ?
C6 C7 C8 C9 0.9(8) . . . . ?
C7 C8 C9 N2 178.9(5) . . . . ?
C7 C8 C9 C4 -1.1(8) . . . . ?
C9 N2 C10 C11 -0.1(8) . . . . ?
C9 C4 C5 C6 1.1(8) . . . . ?
C10 N2 C9 C4 -0.7(8) . . . . ?
C10 N2 C9 C8 179.3(5) . . . . ?
C11 N1 C3 C2 0.7(6) . . . . ?
C11 N1 C4 C5 -178.9(5) . . . . ?
C11 N1 C4 C9 0.9(7) . . . . ?
C11 C1 C2 C3 0.2(7) . . . . ?

_shelx_res_file                  
;
TITL 11_b.res in Pna2(1)
    11.res
    created by SHELXL-2019/2 at 11:14:51 on 10-Sep-2024
REM Old TITL 11 in Pna2(1)
REM SHELXT solution in Pna2(1)
REM R1 0.068, Rweak 0.003, Alpha 0.031, Orientation as input
REM Flack x = 0.224 ( 0.021 ) from Parsons' quotients
REM Formula found by SHELXT: C11 N2 Br
CELL 1.54178 13.4291 4.1088 16.6768 90 90 90
ZERR 4 0.0006 0.0002 0.0007 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H Br N
UNIT 44 28 4 8

L.S. 10
PLAN  5
SIZE 0.18 0.09 0.08
TEMP -100.15
CONF
BOND $H
LIST 4
MORE -1
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\11.hkl">
REM </olex2.extras>

WGHT    0.020600    1.144700
BASF   0.21199
FVAR       0.54047
BR1   3    0.558862    0.196534    0.302910    11.00000    0.03996    0.03247 =
         0.02562   -0.00174   -0.00772   -0.00197
N1    4    0.685523    0.618039    0.496848    11.00000    0.02086    0.02493 =
         0.02267    0.00247   -0.00204   -0.00155
N2    4    0.493075    0.845378    0.533136    11.00000    0.02069    0.03506 =
         0.02701    0.00058   -0.00100   -0.00272
C1    1    0.638911    0.357521    0.385763    11.00000    0.03120    0.03000 =
         0.02291    0.00278   -0.00091    0.00009
C2    1    0.742110    0.318172    0.395589    11.00000    0.02971    0.03236 =
         0.02679    0.00064    0.00313    0.00168
AFIX  43
H2    2    0.785460    0.201634    0.360918    11.00000   -1.20000
AFIX   0
C3    1    0.768948    0.479575    0.464731    11.00000    0.02371    0.03444 =
         0.02533    0.00077   -0.00074    0.00169
AFIX  43
H3    2    0.834280    0.492345    0.486351    11.00000   -1.20000
AFIX   0
C4    1    0.673139    0.816151    0.564465    11.00000    0.02575    0.02489 =
         0.01724    0.00401    0.00077   -0.00055
C5    1    0.751867    0.904087    0.613940    11.00000    0.02568    0.02916 =
         0.02778    0.00558   -0.00251   -0.00515
AFIX  43
H5    2    0.817482    0.832105    0.602160    11.00000   -1.20000
AFIX   0
C6    1    0.734473    1.095173    0.679833    11.00000    0.03688    0.03512 =
         0.02445    0.00324   -0.00759   -0.00386
AFIX  43
H6    2    0.788195    1.151326    0.714217    11.00000   -1.20000
AFIX   0
C7    1    0.638145    1.209136    0.697188    11.00000    0.04373    0.02763 =
         0.02136   -0.00145    0.00205   -0.00186
AFIX  43
H7    2    0.626791    1.342406    0.742831    11.00000   -1.20000
AFIX   0
C8    1    0.560288    1.125678    0.647341    11.00000    0.02869    0.03094 =
         0.02385    0.00607    0.00513    0.00190
AFIX  43
H8    2    0.495345    1.205185    0.658588    11.00000   -1.20000
AFIX   0
C9    1    0.575306    0.926029    0.580528    11.00000    0.02540    0.02520 =
         0.02114    0.00335   -0.00152   -0.00332
C10   1    0.509083    0.663323    0.471170    11.00000    0.01787    0.03474 =
         0.02612    0.00356   -0.00331   -0.00183
AFIX  43
H10   2    0.453552    0.607085    0.438713    11.00000   -1.20000
AFIX   0
C11   1    0.603559    0.542168    0.448389    11.00000    0.02519    0.02207 =
         0.02359    0.00500   -0.00235    0.00015
HKLF 4




REM  11_b.res in Pna2(1)
REM wR2 = 0.0659, GooF = S = 1.053, Restrained GooF = 1.053 for all data
REM R1 = 0.0280 for 1696 Fo > 4sig(Fo) and 0.0309 for all 1791 data
REM 128 parameters refined using 1 restraints

END

WGHT      0.0206      1.1447

REM Highest difference peak  0.306,  deepest hole -0.468,  1-sigma level  0.064
Q1    1   0.5647  0.0110  0.2612  11.00000  0.05    0.31
Q2    1   0.5641  0.0020  0.3401  11.00000  0.05    0.29
Q3    1   0.5780  0.0426  0.3752  11.00000  0.05    0.28
Q4    1   0.5589  0.4079  0.3167  11.00000  0.05    0.23
Q5    1   0.8329  0.2852  0.3019  11.00000  0.05    0.22
;
_shelx_res_checksum              88062
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.79(4)
2 0.21(4)

