# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_7038
_database_code_depnum_ccdc_archive 'CCDC 1940117'
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 Br N O2'
_chemical_formula_sum            'C24 H14 Br N O2'
_chemical_formula_weight         428.27

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'

_symmetry_cell_setting           triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7672(7)
_cell_length_b                   9.2017(10)
_cell_length_c                   15.1089(11)
_cell_angle_alpha                81.431(7)
_cell_angle_beta                 82.868(7)
_cell_angle_gamma                80.818(9)
_cell_volume                     913.54(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1818
_cell_measurement_theta_min      4.0550
_cell_measurement_theta_max      26.3050

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8048
_exptl_absorpt_correction_T_max  0.8392
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6979
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3582
_reflns_number_gt                2478
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1006P)²+0.0173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3582
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1868
_refine_ls_wR_factor_gt          0.1675
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br -0.00895(8) 0.49544(6) 0.17349(3) 0.0540(3) Uani 1 1 d . . .
O002 O 0.1796(4) 0.6577(3) 0.44205(18) 0.0298(7) Uani 1 1 d . . .
O003 O 0.4473(6) 0.3599(4) 0.2763(2) 0.0606(11) Uani 1 1 d . . .
N004 N 0.4693(6) 0.7223(4) 0.1688(2) 0.0386(10) Uani 1 1 d . . .
C005 C 0.3273(6) 0.4070(5) 0.4240(3) 0.0298(10) Uani 1 1 d . . .
C006 C 0.2467(6) 0.5145(5) 0.4781(3) 0.0310(10) Uani 1 1 d . . .
C007 C 0.2807(6) 0.6004(5) 0.2932(3) 0.0295(10) Uani 1 1 d . . .
C008 C 0.1006(6) 0.8514(5) 0.3284(3) 0.0292(10) Uani 1 1 d . . .
C009 C 0.1945(6) 0.6960(5) 0.3511(3) 0.0277(10) Uani 1 1 d . . .
C00A C 0.3574(7) 0.4476(5) 0.3261(3) 0.0378(11) Uani 1 1 d . . .
C00B C 0.3201(6) 0.6451(5) 0.1945(3) 0.0315(10) Uani 1 1 d . . .
C00C C 0.2976(7) 0.3460(6) 0.6107(3) 0.0402(12) Uani 1 1 d . . .
H00C H 0.2920 0.3256 0.6731 0.048 Uiso 1 1 calc R . .
C00D C -0.0158(7) 0.8910(5) 0.2570(3) 0.0375(11) Uani 1 1 d . . .
H00D H -0.0216 0.8225 0.2183 0.045 Uiso 1 1 calc R . .
C00E C 0.2320(6) 0.4866(6) 0.5718(3) 0.0358(11) Uani 1 1 d . . .
H00E H 0.1792 0.5615 0.6068 0.043 Uiso 1 1 calc R . .
C00F C 0.3902(7) 0.2636(5) 0.4655(3) 0.0379(11) Uani 1 1 d . . .
H00F H 0.4441 0.1887 0.4307 0.046 Uiso 1 1 calc R . .
C00G C 0.2126(7) 0.5984(6) 0.1324(3) 0.0382(11) Uani 1 1 d . . .
C00H C 0.5228(7) 0.7567(5) 0.0778(3) 0.0373(12) Uani 1 1 d . . .
C00I C 0.4245(7) 0.7109(5) 0.0123(3) 0.0385(12) Uani 1 1 d . . .
C00J C 0.2623(8) 0.6299(6) 0.0415(3) 0.0438(13) Uani 1 1 d . . .
H00J H 0.1916 0.5990 0.0004 0.053 Uiso 1 1 calc R . .
C00K C 0.3722(7) 0.2332(6) 0.5586(3) 0.0440(13) Uani 1 1 d . . .
H00K H 0.4102 0.1372 0.5862 0.053 Uiso 1 1 calc R . .
C00L C -0.1235(8) 1.0322(6) 0.2431(4) 0.0499(14) Uani 1 1 d . . .
H00L H -0.2029 1.0576 0.1955 0.060 Uiso 1 1 calc R . .
C00M C -0.1135(8) 1.1346(6) 0.2989(4) 0.0515(15) Uani 1 1 d . . .
H00M H -0.1875 1.2288 0.2900 0.062 Uiso 1 1 calc R . .
C00N C 0.1107(8) 0.9560(6) 0.3843(4) 0.0437(12) Uani 1 1 d . . .
H00N H 0.1876 0.9309 0.4327 0.052 Uiso 1 1 calc R . .
C00O C 0.4906(9) 0.7465(6) -0.0798(3) 0.0518(15) Uani 1 1 d . . .
H00O H 0.4265 0.7165 -0.1235 0.062 Uiso 1 1 calc R . .
C00P C 0.0070(8) 1.0969(6) 0.3681(4) 0.0533(14) Uani 1 1 d . . .
H00P H 0.0184 1.1676 0.4045 0.064 Uiso 1 1 calc R . .
C00Q C 0.6837(8) 0.8388(7) 0.0507(4) 0.0526(15) Uani 1 1 d . . .
H00Q H 0.7496 0.8697 0.0935 0.063 Uiso 1 1 calc R . .
C00R C 0.6461(10) 0.8238(7) -0.1043(4) 0.0619(18) Uani 1 1 d . . .
H00R H 0.6903 0.8448 -0.1650 0.074 Uiso 1 1 calc R . .
C00S C 0.7428(9) 0.8732(7) -0.0394(4) 0.0630(18) Uani 1 1 d . . .
H00S H 0.8471 0.9292 -0.0576 0.076 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 C00G 1.892(5) . ?
O002 C009 1.362(5) . ?
O002 C006 1.376(5) . ?
O003 C00A 1.223(6) . ?
N004 C00B 1.314(6) . ?
N004 C00H 1.380(6) . ?
C005 C006 1.379(6) . ?
C005 C00F 1.399(6) . ?
C005 C00A 1.468(6) . ?
C006 C00E 1.394(6) . ?
C007 C009 1.349(6) . ?
C007 C00A 1.455(6) . ?
C007 C00B 1.489(6) . ?
C008 C00D 1.385(6) . ?
C008 C00N 1.386(7) . ?
C008 C009 1.478(6) . ?
C00B C00G 1.409(7) . ?
C00C C00E 1.368(7) . ?
C00C C00K 1.389(7) . ?
C00C H00C 0.9300 . ?
C00D C00L 1.385(7) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00F C00K 1.387(7) . ?
C00F H00F 0.9300 . ?
C00G C00J 1.371(7) . ?
C00H C00I 1.405(7) . ?
C00H C00Q 1.409(7) . ?
C00I C00J 1.413(7) . ?
C00I C00O 1.414(7) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00M 1.369(8) . ?
C00L H00L 0.9300 . ?
C00M C00P 1.376(8) . ?
C00M H00M 0.9300 . ?
C00N C00P 1.375(7) . ?
C00N H00N 0.9300 . ?
C00O C00R 1.347(9) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q C00S 1.375(7) . ?
C00Q H00Q 0.9300 . ?
C00R C00S 1.408(9) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?

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
C009 O002 C006 119.9(3) . . ?
C00B N004 C00H 118.4(4) . . ?
C006 C005 C00F 118.2(4) . . ?
C006 C005 C00A 119.7(4) . . ?
C00F C005 C00A 122.0(4) . . ?
C005 C006 O002 121.5(4) . . ?
C005 C006 C00E 122.6(4) . . ?
O002 C006 C00E 116.0(4) . . ?
C009 C007 C00A 120.6(4) . . ?
C009 C007 C00B 123.4(4) . . ?
C00A C007 C00B 115.8(4) . . ?
C00D C008 C00N 119.0(4) . . ?
C00D C008 C009 120.7(4) . . ?
C00N C008 C009 119.9(4) . . ?
C007 C009 O002 122.7(4) . . ?
C007 C009 C008 127.1(4) . . ?
O002 C009 C008 110.1(4) . . ?
O003 C00A C007 122.6(4) . . ?
O003 C00A C005 122.0(4) . . ?
C007 C00A C005 115.3(4) . . ?
N004 C00B C00G 122.1(4) . . ?
N004 C00B C007 115.9(4) . . ?
C00G C00B C007 121.8(4) . . ?
C00E C00C C00K 121.0(4) . . ?
C00E C00C H00C 119.5 . . ?
C00K C00C H00C 119.5 . . ?
C008 C00D C00L 120.3(5) . . ?
C008 C00D H00D 119.9 . . ?
C00L C00D H00D 119.9 . . ?
C00C C00E C006 118.1(5) . . ?
C00C C00E H00E 120.9 . . ?
C006 C00E H00E 120.9 . . ?
C00K C00F C005 119.9(5) . . ?
C00K C00F H00F 120.0 . . ?
C005 C00F H00F 120.0 . . ?
C00J C00G C00B 121.0(5) . . ?
C00J C00G Br01 118.8(4) . . ?
C00B C00G Br01 120.2(3) . . ?
N004 C00H C00I 122.3(4) . . ?
N004 C00H C00Q 118.1(5) . . ?
C00I C00H C00Q 119.6(4) . . ?
C00H C00I C00J 118.3(4) . . ?
C00H C00I C00O 119.3(5) . . ?
C00J C00I C00O 122.4(5) . . ?
C00G C00J C00I 117.9(5) . . ?
C00G C00J H00J 121.1 . . ?
C00I C00J H00J 121.1 . . ?
C00F C00K C00C 120.1(4) . . ?
C00F C00K H00K 120.0 . . ?
C00C C00K H00K 120.0 . . ?
C00M C00L C00D 120.3(5) . . ?
C00M C00L H00L 119.8 . . ?
C00D C00L H00L 119.8 . . ?
C00L C00M C00P 119.5(5) . . ?
C00L C00M H00M 120.3 . . ?
C00P C00M H00M 120.3 . . ?
C008 C00N C00P 120.0(5) . . ?
C008 C00N H00N 120.0 . . ?
C00P C00N H00N 120.0 . . ?
C00R C00O C00I 120.2(6) . . ?
C00R C00O H00O 119.9 . . ?
C00I C00O H00O 119.9 . . ?
C00M C00P C00N 120.9(5) . . ?
C00M C00P H00P 119.6 . . ?
C00N C00P H00P 119.6 . . ?
C00S C00Q C00H 119.7(6) . . ?
C00S C00Q H00Q 120.2 . . ?
C00H C00Q H00Q 120.2 . . ?
C00O C00R C00S 120.9(5) . . ?
C00O C00R H00R 119.5 . . ?
C00S C00R H00R 119.5 . . ?
C00Q C00S C00R 120.2(6) . . ?
C00Q C00S H00S 119.9 . . ?
C00R C00S H00S 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.702
_refine_diff_density_min         -1.221
_refine_diff_density_rms         0.126
