# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_1_form-iii
_database_code_depnum_ccdc_archive 'CCDC 1882092'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2018-11-29 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_audit_creation_date             2018-06-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H8 Br1.25 N0.75 O3.5'
_chemical_formula_sum            'C13 H8 Br1.25 N0.75 O3.50'
_chemical_formula_weight         330.59
_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 0.0033 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8549(9)
_cell_length_b                   11.732(2)
_cell_length_c                   27.480(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1242.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3397
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.6
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   0.684
_shelx_estimated_absorpt_T_min   0.660
_exptl_absorpt_coefficient_mu    4.114
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            11527
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.283
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2242
_reflns_number_total             2444
_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       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_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    'SHELXL-14 (Sheldrick, 2014)'
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.051(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.056
_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)+(0.0252P)²+1.1796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: N1(0.75) O3(0.75) O4(0.75) Br2(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C13(H13), C12(H12), C9(H9), C10(H10), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C2 C 0.545(2) 1.1989(5) 0.1463(2) 0.0379(16) Uani 1 1 d . . . . .
H2 H 0.5060 1.2741 0.1347 0.045 Uiso 1 1 calc R . . . .
C4 C 0.5057(18) 0.9956(5) 0.1365(2) 0.0315(13) Uani 1 1 d . . . . .
C3 C 0.451(2) 1.1047(5) 0.1187(2) 0.0383(15) Uani 1 1 d . . . . .
H3 H 0.3482 1.1151 0.0876 0.046 Uiso 1 1 calc R . . . .
C5 C 0.6555(19) 0.9797(6) 0.1816(3) 0.0366(17) Uani 1 1 d . . . . .
H5 H 0.6925 0.9047 0.1935 0.044 Uiso 1 1 calc R . . . .
C13 C 0.4555(17) 0.6725(5) 0.0550(2) 0.0342(14) Uani 1 1 d . . . . .
H13 H 0.5740 0.7271 0.0356 0.041 Uiso 1 1 calc R . . . .
C12 C 0.3560(16) 0.5694(5) 0.0354(3) 0.0357(15) Uani 1 1 d . . . . .
H12 H 0.4016 0.5528 0.0022 0.043 Uiso 1 1 calc R . . . .
C1 C 0.6960(18) 1.1799(6) 0.1911(2) 0.0353(16) Uani 1 1 d . . . . .
C9 C 0.2160(19) 0.6174(6) 0.1323(2) 0.0357(16) Uani 1 1 d . . . . .
H9 H 0.1695 0.6348 0.1654 0.043 Uiso 1 1 calc R . . . .
C10 C 0.1184(19) 0.5125(6) 0.1125(3) 0.0374(16) Uani 1 1 d . . . . .
H10 H 0.0043 0.4572 0.1320 0.045 Uiso 1 1 calc R . . . .
C8 C 0.3813(16) 0.6949(5) 0.1026(2) 0.0312(14) Uani 1 1 d . . . . .
C11 C 0.1895(17) 0.4903(5) 0.0644(2) 0.0301(14) Uani 1 1 d . . . . .
C7 C 0.3844(17) 0.8971(6) 0.1065(3) 0.0349(15) Uani 1 1 d . . . . .
C6 C 0.7521(19) 1.0727(6) 0.2096(2) 0.0370(17) Uani 1 1 d . . . . .
H6 H 0.8546 1.0626 0.2407 0.044 Uiso 1 1 calc R . . . .
O1 O 0.4901(14) 0.7973(3) 0.12547(15) 0.0382(11) Uani 1 1 d . . . . .
O2 O 0.2068(15) 0.9059(4) 0.07090(18) 0.0498(14) Uani 1 1 d . . . . .
Br1 Br 0.04400(17) 0.34946(6) 0.03680(3) 0.0409(2) Uani 1 1 d . . . . .
N1 N 0.813(10) 1.284(3) 0.2220(13) 0.050(8) Uani 0.75 1 d . . P A 1
O3 O 0.952(3) 1.2609(7) 0.2582(3) 0.071(3) Uani 0.75 1 d . . P A 1
O4 O 0.727(3) 1.3707(8) 0.2075(3) 0.064(3) Uani 0.75 1 d . . P A 1
Br2 Br 0.809(4) 1.3113(14) 0.2281(7) 0.054(2) Uani 0.25 1 d . . P A 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
C2 H2 0.9500 . ?
C2 C3 1.387(9) . ?
C2 C1 1.382(9) . ?
C4 C3 1.387(9) . ?
C4 C5 1.381(9) . ?
C4 C7 1.496(9) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.385(9) . ?
C13 H13 0.9500 . ?
C13 C12 1.378(9) . ?
C13 C8 1.366(9) . ?
C12 H12 0.9500 . ?
C12 C11 1.381(9) . ?
C1 C6 1.373(10) . ?
C1 N1 1.55(3) . ?
C1 Br2 1.897(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.397(9) . ?
C9 C8 1.377(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(9) . ?
C8 O1 1.419(7) . ?
C11 Br1 1.902(6) . ?
C7 O1 1.345(8) . ?
C7 O2 1.198(8) . ?
C6 H6 0.9500 . ?
N1 O3 1.16(4) . ?
N1 O4 1.14(4) . ?

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 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.0(6) . . ?
C3 C4 C7 118.1(6) . . ?
C5 C4 C3 120.4(6) . . ?
C5 C4 C7 121.4(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(6) . . ?
C4 C3 H3 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(6) . . ?
C6 C5 H5 119.9 . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C8 C13 C12 119.0(6) . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.6(6) . . ?
C11 C12 H12 120.2 . . ?
C2 C1 N1 118.9(17) . . ?
C2 C1 Br2 116.3(8) . . ?
C6 C1 C2 122.9(6) . . ?
C6 C1 N1 118.2(17) . . ?
C6 C1 Br2 120.7(8) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.4(6) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(6) . . ?
C11 C10 H10 120.4 . . ?
C13 C8 C9 122.5(6) . . ?
C13 C8 O1 121.7(6) . . ?
C9 C8 O1 115.7(6) . . ?
C12 C11 Br1 119.4(5) . . ?
C10 C11 C12 121.3(6) . . ?
C10 C11 Br1 119.3(5) . . ?
O1 C7 C4 111.3(5) . . ?
O2 C7 C4 124.2(6) . . ?
O2 C7 O1 124.4(6) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 C5 118.3(6) . . ?
C1 C6 H6 120.8 . . ?
C7 O1 C8 118.4(5) . . ?
O3 N1 C1 115(3) . . ?
O4 N1 C1 115(3) . . ?
O4 N1 O3 130(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 O2 0.95 2.38 3.232(8) 149.5 4_565
C9 H9 O3 0.95 2.61 3.508(11) 157.9 3_645
C10 H10 O4 0.95 2.54 3.444(12) 158.1 1_445

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
C2 C1 C6 C5 0.7(12) . . . . ?
C2 C1 N1 O3 -177(2) . . . . ?
C2 C1 N1 O4 9(3) . . . . ?
C4 C5 C6 C1 -0.2(11) . . . . ?
C4 C7 O1 C8 176.8(6) . . . . ?
C3 C2 C1 C6 -0.9(12) . . . . ?
C3 C2 C1 N1 178.3(16) . . . . ?
C3 C2 C1 Br2 -178.4(8) . . . . ?
C3 C4 C5 C6 0.0(11) . . . . ?
C3 C4 C7 O1 172.9(6) . . . . ?
C3 C4 C7 O2 -9.2(11) . . . . ?
C5 C4 C3 C2 -0.3(11) . . . . ?
C5 C4 C7 O1 -9.7(9) . . . . ?
C5 C4 C7 O2 168.1(7) . . . . ?
C13 C12 C11 C10 0.4(10) . . . . ?
C13 C12 C11 Br1 178.7(5) . . . . ?
C13 C8 O1 C7 58.5(9) . . . . ?
C12 C13 C8 C9 1.3(10) . . . . ?
C12 C13 C8 O1 177.2(6) . . . . ?
C1 C2 C3 C4 0.7(11) . . . . ?
C9 C10 C11 C12 0.2(10) . . . . ?
C9 C10 C11 Br1 -178.0(5) . . . . ?
C9 C8 O1 C7 -125.3(7) . . . . ?
C10 C9 C8 C13 -0.6(10) . . . . ?
C10 C9 C8 O1 -176.8(6) . . . . ?
C8 C13 C12 C11 -1.2(10) . . . . ?
C8 C9 C10 C11 -0.1(10) . . . . ?
C7 C4 C3 C2 177.1(7) . . . . ?
C7 C4 C5 C6 -177.2(7) . . . . ?
C6 C1 N1 O3 3(3) . . . . ?
C6 C1 N1 O4 -172(2) . . . . ?
O2 C7 O1 C8 -1.0(10) . . . . ?
N1 C1 C6 C5 -178.5(16) . . . . ?
Br2 C1 C6 C5 178.1(8) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
