# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_njx-2
_database_code_depnum_ccdc_archive 'CCDC 2081268'
loop_
_audit_author_name
_audit_author_address
'Eduardo C Escudero Adan'
;Institute of Chemical Research of Catalonia
Spain
;
_audit_update_record             
;
2021-04-30 deposited with the CCDC.	2021-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br N O'
_chemical_formula_weight         238.08

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   14.6642(17)
_cell_length_b                   11.8423(9)
_cell_length_c                   5.5080(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     956.52(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    481
_cell_measurement_theta_min      4.3070
_cell_measurement_theta_max      28.4780

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.254
_shelx_estimated_absorpt_T_min   0.483
_shelx_estimated_absorpt_T_max   0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38030
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            7851
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.778
_diffrn_reflns_theta_max         30.136
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2452
_reflns_number_gt                2070
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_max     0.780
_reflns_Friedel_fraction_full    0.931

_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 1.171.39.12b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_structure_solution    Sir2019
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0292P)²] 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 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2452
_refine_ls_number_parameters     118
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0602
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
N1 N 0.08848(19) -0.0251(3) -0.2641(6) 0.0250(7) Uani 1 1 d . . . . .
C1 C 0.1155(2) 0.5894(3) 0.3262(6) 0.0154(7) Uani 1 1 d . . . . .
O1 O 0.18268(16) 0.23169(18) -0.1141(4) 0.0169(6) Uani 1 1 d . . . . .
Br1 Br 0.10407(2) 0.73968(2) 0.43898(13) 0.02398(11) Uani 1 1 d . . . . .
C2 C 0.1575(2) 0.5672(3) 0.1052(6) 0.0159(7) Uani 1 1 d . . . . .
H2 H 0.179496 0.627344 0.007156 0.019 Uiso 1 1 calc R U . . .
C3 C 0.1667(2) 0.4560(3) 0.0296(6) 0.0141(7) Uani 1 1 d . . . . .
H3 H 0.195206 0.440183 -0.121532 0.017 Uiso 1 1 calc R U . . .
C4 C 0.1348(2) 0.3673(3) 0.1725(6) 0.0133(7) Uani 1 1 d . . . . .
C5 C 0.09243(18) 0.3914(3) 0.3939(6) 0.0137(8) Uani 1 1 d . . . . .
H5 H 0.070634 0.331639 0.493118 0.016 Uiso 1 1 calc R U . . .
C6 C 0.08212(19) 0.5026(3) 0.4690(7) 0.0156(7) Uani 1 1 d . . . . .
H6 H 0.052262 0.519016 0.617933 0.019 Uiso 1 1 calc R U . . .
C7 C 0.1488(2) 0.2496(3) 0.0847(7) 0.0131(7) Uani 1 1 d . . . . .
C8 C 0.1193(2) 0.1540(3) 0.2474(6) 0.0144(7) Uani 1 1 d . . . . .
H8A H 0.051885 0.153669 0.258114 0.017 Uiso 1 1 calc R U . . .
H8B H 0.143601 0.167145 0.412621 0.017 Uiso 1 1 calc R U . . .
C9 C 0.1515(2) 0.0387(3) 0.1580(7) 0.0184(7) Uani 1 1 d . . . . .
H9A H 0.218960 0.039547 0.148605 0.022 Uiso 1 1 calc R U . . .
H9B H 0.134024 -0.018879 0.279612 0.022 Uiso 1 1 calc R U . . .
C10 C 0.1150(2) 0.0044(3) -0.0805(9) 0.0187(7) 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
N1 0.0300(16) 0.0260(18) 0.0191(17) -0.0043(14) 0.0019(14) -0.0080(13)
C1 0.0140(15) 0.0130(16) 0.0192(17) 0.0006(13) -0.0030(14) 0.0006(13)
O1 0.0187(11) 0.0176(12) 0.0144(19) -0.0021(9) 0.0026(9) -0.0004(9)
Br1 0.02818(18) 0.01500(15) 0.02878(19) -0.0040(3) 0.0070(2) 0.00016(12)
C2 0.0155(16) 0.0145(17) 0.0177(18) 0.0015(14) 0.0010(14) -0.0005(13)
C3 0.0130(15) 0.0187(17) 0.0106(16) 0.0012(13) -0.0007(13) 0.0017(13)
C4 0.0105(15) 0.0155(16) 0.0139(17) -0.0008(13) -0.0038(13) 0.0010(12)
C5 0.0128(14) 0.0166(14) 0.012(2) 0.0034(12) -0.0017(12) -0.0012(11)
C6 0.0139(13) 0.0218(15) 0.011(2) -0.0006(16) -0.0003(15) 0.0016(11)
C7 0.0097(16) 0.0167(18) 0.0128(17) -0.0001(13) -0.0036(13) -0.0003(13)
C8 0.0145(15) 0.0164(16) 0.0124(16) 0.0000(13) -0.0001(13) -0.0024(13)
C9 0.0243(19) 0.0144(16) 0.0165(19) -0.0003(14) -0.0001(15) 0.0005(14)
C10 0.0213(14) 0.0163(13) 0.0186(19) 0.001(2) 0.006(2) -0.0033(12)

_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
N1 C10 1.139(5) . ?
C1 C6 1.384(5) . ?
C1 C2 1.389(5) . ?
C1 Br1 1.892(3) . ?
O1 C7 1.221(4) . ?
C2 C3 1.388(5) . ?
C3 C4 1.394(4) . ?
C4 C5 1.399(4) . ?
C4 C7 1.490(4) . ?
C5 C6 1.388(4) . ?
C7 C8 1.507(5) . ?
C8 C9 1.526(5) . ?
C9 C10 1.476(6) . ?

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
C6 C1 C2 120.9(3) . . ?
C6 C1 Br1 118.7(3) . . ?
C2 C1 Br1 120.3(2) . . ?
C3 C2 C1 119.1(3) . . ?
C2 C3 C4 120.9(3) . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 C7 118.4(3) . . ?
C5 C4 C7 122.4(3) . . ?
C6 C5 C4 120.1(3) . . ?
C1 C6 C5 119.8(3) . . ?
O1 C7 C4 120.6(3) . . ?
O1 C7 C8 121.3(3) . . ?
C4 C7 C8 118.1(3) . . ?
C7 C8 C9 113.0(3) . . ?
C10 C9 C8 114.9(3) . . ?
N1 C10 C9 177.9(4) . . ?

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
C6 C1 C2 C3 -0.8(5) . . . . ?
Br1 C1 C2 C3 178.5(2) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C2 C3 C4 C7 -178.5(3) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C7 C4 C5 C6 179.2(3) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
Br1 C1 C6 C5 -177.8(2) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C3 C4 C7 O1 -4.1(4) . . . . ?
C5 C4 C7 O1 177.0(3) . . . . ?
C3 C4 C7 C8 176.3(3) . . . . ?
C5 C4 C7 C8 -2.6(5) . . . . ?
O1 C7 C8 C9 10.3(4) . . . . ?
C4 C7 C8 C9 -170.2(3) . . . . ?
C7 C8 C9 C10 -62.7(4) . . . . ?

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.075

_shelx_res_file                  
;
TITL ICIQ 25a-21 NJX-2LT 20210208 in Pca2(1)
    njx-2.res
    created by SHELXL-2018/3 at 09:55:47 on 31-Mar-2021
CELL 0.71073  14.664220  11.842340   5.508049  90.0000  90.0000  90.0000
ZERR    4.00   0.001661   0.000910   0.000549   0.0000   0.0000   0.0000
LATT -1
SYMM -x,-y, z+1/2
SYMM  x+1/2,-y, z
SYMM -x+1/2, y, z+1/2
SFAC C  H  N  O  Br
UNIT 40 32 4 4 4
LIST 4
L.S. 20
ACTA
conf
BOND
FMAP 2
PLAN 20
size 0.2 0.2 0.1
temp -173
WGHT    0.029200
FVAR       0.27444
MOLE 1
REM #####
N1    3    0.088479   -0.025080   -0.264062    11.00000    0.02996    0.02595 =
         0.01911   -0.00426    0.00186   -0.00795
C1    1    0.115474    0.589415    0.326204    11.00000    0.01404    0.01296 =
         0.01923    0.00061   -0.00301    0.00057
O1    4    0.182677    0.231689   -0.114109    11.00000    0.01872    0.01760 =
         0.01439   -0.00212    0.00261   -0.00038
BR1   5    0.104072    0.739679    0.438982    11.00000    0.02818    0.01500 =
         0.02878   -0.00396    0.00700    0.00016
C2    1    0.157455    0.567242    0.105168    11.00000    0.01546    0.01448 =
         0.01770    0.00145    0.00103   -0.00048
AFIX  43
H2    2    0.179496    0.627344    0.007156    11.00000   -1.20000
AFIX   0
C3    1    0.166732    0.456033    0.029595    11.00000    0.01305    0.01875 =
         0.01056    0.00123   -0.00074    0.00170
AFIX  43
H3    2    0.195206    0.440183   -0.121532    11.00000   -1.20000
AFIX   0
C4    1    0.134830    0.367313    0.172462    11.00000    0.01050    0.01552 =
         0.01389   -0.00082   -0.00380    0.00098
C5    1    0.092428    0.391448    0.393892    11.00000    0.01276    0.01661 =
         0.01161    0.00339   -0.00171   -0.00119
AFIX  43
H5    2    0.070634    0.331639    0.493118    11.00000   -1.20000
AFIX   0
C6    1    0.082119    0.502597    0.468993    11.00000    0.01388    0.02177 =
         0.01126   -0.00063   -0.00033    0.00156
AFIX  43
H6    2    0.052262    0.519016    0.617933    11.00000   -1.20000
AFIX   0
C7    1    0.148787    0.249575    0.084655    11.00000    0.00973    0.01673 =
         0.01280   -0.00011   -0.00362   -0.00035
C8    1    0.119275    0.154005    0.247355    11.00000    0.01453    0.01639 =
         0.01237   -0.00004   -0.00006   -0.00241
AFIX  23
H8A   2    0.051885    0.153669    0.258114    11.00000   -1.20000
H8B   2    0.143601    0.167145    0.412621    11.00000   -1.20000
AFIX   0
C9    1    0.151545    0.038748    0.158045    11.00000    0.02426    0.01437 =
         0.01654   -0.00035   -0.00012    0.00051
AFIX  23
H9A   2    0.218960    0.039547    0.148605    11.00000   -1.20000
H9B   2    0.134024   -0.018879    0.279612    11.00000   -1.20000
AFIX   0
C10   1    0.115050    0.004409   -0.080454    11.00000    0.02129    0.01630 =
         0.01859    0.00120    0.00595   -0.00334
HKLF 4




REM  ICIQ 25a-21 NJX-2LT 20210208 in Pca2(1)
REM wR2 = 0.063719, GooF = S = 1.03623, Restrained GooF = 1.03601 for all data
REM R1 = 0.029051 for 2070 Fo > 4sig(Fo) and 0.041279 for all 2452 data
REM 118 parameters refined using 1 restraints

END

WGHT      0.0252      0.1130

REM Highest difference peak  0.463,  deepest hole -0.502,  1-sigma level  0.075
Q1    1   0.1716  0.7455  0.4358  11.00000  0.05    0.46
Q2    1   0.0286  0.7403  0.4453  11.00000  0.05    0.45
Q3    1   0.1043  0.8060  0.4316  11.00000  0.05    0.39
Q4    1   0.1361  0.3069  0.1260  11.00000  0.05    0.33
Q5    1   0.0656  0.7428  0.3301  11.00000  0.05    0.32
Q6    1   0.0991  0.4481  0.4449  11.00000  0.05    0.31
Q7    1   0.0408  0.8177  0.4502  11.00000  0.05    0.30
Q8    1   0.1055  0.6763  0.4386  11.00000  0.05    0.29
Q9    1   0.0810  0.0432 -0.1708  11.00000  0.05    0.29
Q10   1   0.0625  0.5821  0.0826  11.00000  0.05    0.29
Q11   1   0.1229  0.0830  0.2145  11.00000  0.05    0.28
Q12   1   0.1301  0.3048 -0.2689  11.00000  0.05    0.28
Q13   1   0.2173  0.7194 -0.0441  11.00000  0.05    0.28
Q14   1   0.1524  0.5090  0.0734  11.00000  0.05    0.27
Q15   1   0.1224  0.0396  0.0374  11.00000  0.05    0.26
Q16   1   0.1310  0.7414  0.2370  11.00000  0.05    0.26
Q17   1   0.2639  0.5005 -0.0374  11.00000  0.05    0.25
Q18   1   0.1204  0.2165  0.1508  11.00000  0.05    0.25
Q19   1   0.1287  0.3838  0.4080  11.00000  0.05    0.24
Q20   1   0.1002  0.6635  0.3375  11.00000  0.05    0.24
;
_shelx_res_checksum              70659
