# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_QLQ1802
_database_code_depnum_ccdc_archive 'CCDC 2007943'
loop_
_audit_author_name
_audit_author_address
'Wesley Ting Kwok Chan'
;Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University
Hong Kong
;
_audit_update_record             
;
2020-06-04 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 Br Cl N O4'
_chemical_formula_sum            'C19 H15 Br Cl N O4'
_chemical_formula_weight         436.68

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'
Cl Cl 0.1484 0.1585 '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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.4479(6)
_cell_length_b                   10.9895(5)
_cell_length_c                   14.0720(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.7484(17)
_cell_angle_gamma                90.00
_cell_volume                     1861.57(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9222
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.23

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      .
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    2.376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3951
_exptl_absorpt_correction_T_max  0.5994
_exptl_absorpt_process_details   'SAINT ver 8.34A; BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Photon-100 CMOS area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            87525
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.57
_reflns_number_total             4294
_reflns_number_gt                3376
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0779P)²+0.9294P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0200(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4294
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Br1 Br 0.35973(16) 0.44590(19) 0.15754(15) 0.0804(6) Uani 0.60 1 d P A 1
Cl1' Cl 0.3608(6) 0.4245(6) 0.1640(6) 0.0622(13) Uani 0.40 1 d P A 2
C1 C 0.5102(2) 0.4676(3) 0.1730(2) 0.0561(6) Uani 1 1 d . . .
C2 C 0.5577(3) 0.4179(3) 0.1027(2) 0.0729(9) Uani 1 1 d . A .
H2A H 0.5150 0.3717 0.0515 0.087 Uiso 1 1 calc R . .
C3 C 0.6684(3) 0.4377(3) 0.1094(3) 0.0772(10) Uani 1 1 d . . .
H3A H 0.7003 0.4063 0.0617 0.093 Uiso 1 1 calc R A .
C4 C 0.7321(3) 0.5035(3) 0.1862(3) 0.0730(9) Uani 1 1 d . A .
H4A H 0.8075 0.5150 0.1920 0.088 Uiso 1 1 calc R . .
C5 C 0.6824(2) 0.5521(2) 0.2543(2) 0.0607(7) Uani 1 1 d . . .
Cl1 Cl 0.76587(17) 0.6404(2) 0.3520(3) 0.0774(9) Uani 0.60 1 d P A 1
Br1' Br 0.7683(3) 0.6384(4) 0.3539(4) 0.1634(16) Uani 0.40 1 d P A 2
C6 C 0.5700(2) 0.5374(2) 0.25035(19) 0.0486(6) Uani 1 1 d . A .
C7 C 0.5218(2) 0.5912(2) 0.32711(19) 0.0476(5) Uani 1 1 d . . .
H7A H 0.5124 0.5407 0.3774 0.057 Uiso 1 1 calc R A .
C8 C 0.49124(17) 0.7066(2) 0.32861(16) 0.0390(5) Uani 1 1 d . A .
C9 C 0.48713(18) 0.8043(2) 0.25748(16) 0.0409(5) Uani 1 1 d . . .
C10 C 0.5173(2) 0.8091(3) 0.16881(19) 0.0555(6) Uani 1 1 d . A .
H10A H 0.5468 0.7411 0.1452 0.067 Uiso 1 1 calc R . .
C11 C 0.5025(3) 0.9169(3) 0.1166(2) 0.0698(8) Uani 1 1 d . . .
H11A H 0.5225 0.9217 0.0574 0.084 Uiso 1 1 calc R A .
C12 C 0.4584(3) 1.0177(3) 0.1513(2) 0.0675(8) Uani 1 1 d . A .
H12A H 0.4500 1.0896 0.1152 0.081 Uiso 1 1 calc R . .
C13 C 0.4267(2) 1.0147(2) 0.2374(2) 0.0546(6) Uani 1 1 d . . .
H13A H 0.3964 1.0830 0.2597 0.066 Uiso 1 1 calc R A .
C14 C 0.44096(17) 0.9073(2) 0.29038(17) 0.0415(5) Uani 1 1 d . A .
N1 N 0.40905(15) 0.88247(17) 0.37578(14) 0.0424(4) Uani 1 1 d . . .
H1A H 0.3676 0.9279 0.4014 0.051 Uiso 1 1 calc R A .
C15 C 0.45741(17) 0.76693(19) 0.41476(16) 0.0382(5) Uani 1 1 d . A .
C16 C 0.56371(18) 0.7868(2) 0.49720(16) 0.0415(5) Uani 1 1 d . . .
O1 O 0.60936(16) 0.88317(17) 0.51445(15) 0.0611(5) Uani 1 1 d . A .
O2 O 0.59868(15) 0.68414(16) 0.54270(14) 0.0566(5) Uani 1 1 d . A .
C17 C 0.7051(3) 0.6874(3) 0.6145(2) 0.0740(9) Uani 1 1 d . . .
H17A H 0.7243 0.6070 0.6399 0.111 Uiso 1 1 calc R A .
H17B H 0.7007 0.7409 0.6673 0.111 Uiso 1 1 calc R . .
H17C H 0.7609 0.7165 0.5839 0.111 Uiso 1 1 calc R . .
C18 C 0.3711(2) 0.6977(2) 0.45401(19) 0.0466(5) Uani 1 1 d . . .
O3 O 0.3205(2) 0.6123(2) 0.4179(2) 0.0972(9) Uani 1 1 d . A .
O4 O 0.35844(18) 0.75260(19) 0.53405(14) 0.0649(5) Uani 1 1 d . A .
C19 C 0.2727(3) 0.7049(4) 0.5764(3) 0.0856(11) Uani 1 1 d . . .
H19A H 0.2893 0.7259 0.6448 0.128 Uiso 1 1 calc R A .
H19B H 0.2696 0.6180 0.5695 0.128 Uiso 1 1 calc R . .
H19C H 0.2023 0.7393 0.5430 0.128 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
Br1 C1 1.846(3) . ?
Cl1' C1 1.892(7) . ?
C1 C6 1.383(4) . ?
C1 C2 1.387(4) . ?
C2 C3 1.374(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.371(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.395(4) . ?
C5 Cl1 1.785(4) . ?
C5 Br1' 1.802(5) . ?
C6 C7 1.486(3) . ?
C7 C8 1.325(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.460(3) . ?
C8 C15 1.532(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.400(3) . ?
C10 C11 1.382(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.365(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.384(3) . ?
C13 H13A 0.9300 . ?
C14 N1 1.385(3) . ?
N1 C15 1.452(3) . ?
N1 H1A 0.8600 . ?
C15 C18 1.530(3) . ?
C15 C16 1.537(3) . ?
C16 O1 1.197(3) . ?
C16 O2 1.315(3) . ?
O2 C17 1.448(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O3 1.172(3) . ?
C18 O4 1.322(3) . ?
O4 C19 1.447(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 122.5(3) . . ?
C6 C1 Br1 119.4(2) . . ?
C2 C1 Br1 118.0(3) . . ?
C6 C1 Cl1' 121.0(3) . . ?
C2 C1 Cl1' 116.3(3) . . ?
Br1 C1 Cl1' 7.6(3) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C4 C5 C6 123.5(3) . . ?
C4 C5 Cl1 118.1(3) . . ?
C6 C5 Cl1 118.3(2) . . ?
C4 C5 Br1' 117.6(3) . . ?
C6 C5 Br1' 118.8(2) . . ?
Cl1 C5 Br1' 1.2(3) . . ?
C1 C6 C5 115.4(2) . . ?
C1 C6 C7 123.8(2) . . ?
C5 C6 C7 120.8(2) . . ?
C8 C7 C6 124.3(2) . . ?
C8 C7 H7A 117.9 . . ?
C6 C7 H7A 117.9 . . ?
C7 C8 C9 130.7(2) . . ?
C7 C8 C15 124.4(2) . . ?
C9 C8 C15 104.81(17) . . ?
C10 C9 C14 119.5(2) . . ?
C10 C9 C8 132.2(2) . . ?
C14 C9 C8 108.26(19) . . ?
C11 C10 C9 118.6(3) . . ?
C11 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C12 C13 C14 118.2(3) . . ?
C12 C13 H13A 120.9 . . ?
C14 C13 H13A 120.9 . . ?
C13 C14 N1 127.6(2) . . ?
C13 C14 C9 121.2(2) . . ?
N1 C14 C9 111.1(2) . . ?
C14 N1 C15 108.48(17) . . ?
C14 N1 H1A 125.8 . . ?
C15 N1 H1A 125.8 . . ?
N1 C15 C18 108.04(17) . . ?
N1 C15 C8 104.51(17) . . ?
C18 C15 C8 115.49(18) . . ?
N1 C15 C16 110.82(18) . . ?
C18 C15 C16 110.30(18) . . ?
C8 C15 C16 107.54(17) . . ?
O1 C16 O2 125.4(2) . . ?
O1 C16 C15 123.5(2) . . ?
O2 C16 C15 111.12(19) . . ?
C16 O2 C17 116.7(2) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O4 124.5(2) . . ?
O3 C18 C15 126.3(2) . . ?
O4 C18 C15 109.1(2) . . ?
C18 O4 C19 116.5(2) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C6 C1 C2 C3 0.2(5) . . . . ?
Br1 C1 C2 C3 176.7(3) . . . . ?
Cl1' C1 C2 C3 -175.0(3) . . . . ?
C1 C2 C3 C4 1.5(5) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 Cl1 -178.5(3) . . . . ?
C3 C4 C5 Br1' -179.8(3) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
Br1 C1 C6 C5 -177.9(2) . . . . ?
Cl1' C1 C6 C5 173.5(3) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
Br1 C1 C6 C7 3.9(4) . . . . ?
Cl1' C1 C6 C7 -4.7(4) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
Cl1 C5 C6 C1 -179.8(2) . . . . ?
Br1' C5 C6 C1 -178.5(3) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
Cl1 C5 C6 C7 -1.6(4) . . . . ?
Br1' C5 C6 C7 -0.3(4) . . . . ?
C1 C6 C7 C8 -100.9(3) . . . . ?
C5 C6 C7 C8 81.0(4) . . . . ?
C6 C7 C8 C9 5.5(4) . . . . ?
C6 C7 C8 C15 -170.7(2) . . . . ?
C7 C8 C9 C10 -2.8(4) . . . . ?
C15 C8 C9 C10 174.0(3) . . . . ?
C7 C8 C9 C14 175.7(2) . . . . ?
C15 C8 C9 C14 -7.5(2) . . . . ?
C14 C9 C10 C11 1.2(4) . . . . ?
C8 C9 C10 C11 179.6(3) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 N1 -176.1(3) . . . . ?
C12 C13 C14 C9 0.4(4) . . . . ?
C10 C9 C14 C13 -1.3(4) . . . . ?
C8 C9 C14 C13 180.0(2) . . . . ?
C10 C9 C14 N1 175.7(2) . . . . ?
C8 C9 C14 N1 -3.1(3) . . . . ?
C13 C14 N1 C15 -170.2(2) . . . . ?
C9 C14 N1 C15 13.1(2) . . . . ?
C14 N1 C15 C18 -140.48(19) . . . . ?
C14 N1 C15 C8 -17.0(2) . . . . ?
C14 N1 C15 C16 98.6(2) . . . . ?
C7 C8 C15 N1 -168.2(2) . . . . ?
C9 C8 C15 N1 14.7(2) . . . . ?
C7 C8 C15 C18 -49.7(3) . . . . ?
C9 C8 C15 C18 133.3(2) . . . . ?
C7 C8 C15 C16 74.0(3) . . . . ?
C9 C8 C15 C16 -103.12(19) . . . . ?
N1 C15 C16 O1 -11.7(3) . . . . ?
C18 C15 C16 O1 -131.3(2) . . . . ?
C8 C15 C16 O1 102.0(3) . . . . ?
N1 C15 C16 O2 170.53(18) . . . . ?
C18 C15 C16 O2 50.9(2) . . . . ?
C8 C15 C16 O2 -75.8(2) . . . . ?
O1 C16 O2 C17 -4.6(4) . . . . ?
C15 C16 O2 C17 173.1(2) . . . . ?
N1 C15 C18 O3 107.3(3) . . . . ?
C8 C15 C18 O3 -9.3(4) . . . . ?
C16 C15 C18 O3 -131.4(3) . . . . ?
N1 C15 C18 O4 -70.0(2) . . . . ?
C8 C15 C18 O4 173.4(2) . . . . ?
C16 C15 C18 O4 51.2(3) . . . . ?
O3 C18 O4 C19 -2.4(5) . . . . ?
C15 C18 O4 C19 175.0(3) . . . . ?

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
N1 H1A Br1 0.86 2.75 3.332(3) 126.7 2
N1 H1A Cl1' 0.86 2.76 3.295(7) 122.0 2
N1 H1A O1 0.86 2.37 3.042(3) 135.1 3_676
C17 H17A O3 0.96 2.56 3.329(4) 137.3 3_666
C19 H19B Br1' 0.96 3.10 3.964(6) 151.2 3_666

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.072
