# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1047215'
_audit_update_record             
;
2018-10-15 deposited with the CCDC.
2018-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 Br Cl N2 O2'
_chemical_formula_weight         341.59

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   5.9701(2)
_cell_length_b                   7.3338(3)
_cell_length_c                   31.4408(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1376.59(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    3.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3487
_exptl_absorpt_correction_T_max  0.4295
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15878
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2422
_reflns_number_gt                2312
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0272P)²+0.3509P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2422
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0569
_refine_ls_wR_factor_gt          0.0560
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.10691(5) 0.77392(4) 0.235561(9) 0.03788(10) Uani 1 1 d . . .
Cl1 Cl 0.28471(14) -0.14637(11) 0.03479(2) 0.03863(19) Uani 1 1 d . . .
O2 O 0.2962(3) 0.2810(2) 0.05967(5) 0.0241(4) Uani 1 1 d . . .
O1 O 0.6393(3) 0.1768(3) 0.07647(6) 0.0302(4) Uani 1 1 d . . .
N1 N -0.2127(5) -0.3596(4) 0.07390(9) 0.0520(8) Uani 1 1 d . . .
C11 C 0.5990(5) -0.1118(4) 0.15959(9) 0.0335(6) Uani 1 1 d . . .
C1 C 0.4184(4) 0.3267(4) 0.18144(8) 0.0275(6) Uani 1 1 d . . .
H1A H 0.5556 0.2630 0.1850 0.033 Uiso 1 1 calc R . .
C2 C 0.3739(5) 0.4789(4) 0.20613(8) 0.0310(6) Uani 1 1 d . . .
H2A H 0.4803 0.5205 0.2264 0.037 Uiso 1 1 calc R . .
C3 C 0.1742(4) 0.5691(4) 0.20096(8) 0.0246(6) Uani 1 1 d . . .
C4 C 0.0170(4) 0.5118(4) 0.17172(8) 0.0241(6) Uani 1 1 d . . .
H4A H -0.1206 0.5755 0.1687 0.029 Uiso 1 1 calc R . .
C5 C 0.0621(4) 0.3602(4) 0.14680(8) 0.0219(5) Uani 1 1 d . . .
H5A H -0.0449 0.3202 0.1265 0.026 Uiso 1 1 calc R . .
C6 C 0.2634(4) 0.2662(3) 0.15142(7) 0.0200(5) Uani 1 1 d . . .
C7 C 0.3218(4) 0.1054(3) 0.12189(8) 0.0195(5) Uani 1 1 d . . .
C8 C 0.1126(4) -0.0069(3) 0.11017(8) 0.0222(5) Uani 1 1 d . . .
H8A H 0.0307 -0.0371 0.1366 0.027 Uiso 1 1 calc R . .
H8B H 0.0128 0.0696 0.0925 0.027 Uiso 1 1 calc R . .
C9 C 0.1615(4) -0.1843(4) 0.08615(8) 0.0266(6) Uani 1 1 d . . .
H9A H 0.2643 -0.2618 0.1036 0.032 Uiso 1 1 calc R . .
C10 C -0.0509(5) -0.2847(4) 0.07867(8) 0.0298(6) Uani 1 1 d . . .
N2 N 0.4784(3) -0.0128(3) 0.14298(7) 0.0228(5) Uani 1 1 d . . .
C12 C 0.4428(4) 0.1895(3) 0.08286(8) 0.0203(5) Uani 1 1 d . . .
C13 C 0.3868(5) 0.3674(4) 0.02162(8) 0.0304(6) Uani 1 1 d . . .
H13A H 0.2666 0.4316 0.0066 0.046 Uiso 1 1 calc R . .
H13B H 0.4510 0.2741 0.0029 0.046 Uiso 1 1 calc R . .
H13C H 0.5036 0.4546 0.0298 0.046 Uiso 1 1 calc R . .

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 0.03797(16) 0.03740(16) 0.03827(16) -0.01811(13) -0.00336(13) 0.00721(13)
Cl1 0.0502(5) 0.0337(4) 0.0320(4) -0.0065(3) 0.0048(3) 0.0034(3)
O2 0.0233(9) 0.0270(10) 0.0219(8) 0.0041(8) 0.0005(7) 0.0040(8)
O1 0.0174(10) 0.0421(11) 0.0311(10) 0.0034(8) 0.0022(7) 0.0024(8)
N1 0.0560(19) 0.0439(16) 0.0560(19) 0.0041(15) -0.0231(15) -0.0138(16)
C11 0.0267(15) 0.0361(17) 0.0378(16) 0.0028(12) -0.0025(14) 0.0038(16)
C1 0.0178(13) 0.0312(15) 0.0335(14) -0.0061(11) -0.0038(11) 0.0029(12)
C2 0.0252(14) 0.0383(16) 0.0296(14) -0.0091(12) -0.0074(13) -0.0010(14)
C3 0.0282(14) 0.0212(13) 0.0245(13) -0.0035(11) 0.0036(11) 0.0002(11)
C4 0.0208(13) 0.0275(15) 0.0241(13) 0.0028(11) 0.0005(11) 0.0058(11)
C5 0.0162(13) 0.0268(13) 0.0226(12) -0.0003(11) -0.0022(10) 0.0020(10)
C6 0.0198(12) 0.0199(13) 0.0204(11) 0.0010(11) 0.0005(9) -0.0011(11)
C7 0.0141(12) 0.0238(13) 0.0205(12) 0.0026(10) -0.0036(9) 0.0035(10)
C8 0.0196(12) 0.0243(13) 0.0227(12) -0.0002(10) -0.0010(11) 0.0018(12)
C9 0.0287(15) 0.0246(15) 0.0266(13) 0.0021(11) -0.0074(11) 0.0026(11)
C10 0.0397(17) 0.0202(13) 0.0295(14) 0.0025(12) -0.0068(11) 0.0007(13)
N2 0.0190(11) 0.0264(12) 0.0231(11) -0.0010(10) -0.0011(9) 0.0042(9)
C12 0.0201(14) 0.0187(13) 0.0221(12) -0.0038(10) -0.0016(9) 0.0008(10)
C13 0.0339(15) 0.0310(14) 0.0263(13) 0.0068(11) -0.0009(13) -0.0042(14)

_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 C3 1.898(3) . ?
Cl1 C9 1.796(3) . ?
O2 C12 1.322(3) . ?
O2 C13 1.458(3) . ?
O1 C12 1.193(3) . ?
N1 C10 1.122(4) . ?
C11 N2 1.148(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.394(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.373(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.379(4) . ?
C4 C5 1.386(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.541(3) . ?
C7 N2 1.437(3) . ?
C7 C8 1.541(3) . ?
C7 C12 1.552(3) . ?
C8 C9 1.532(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.485(4) . ?
C9 H9A 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C12 O2 C13 115.3(2) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 H1A 119.7 . . ?
C6 C1 H1A 119.7 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 Br1 119.8(2) . . ?
C4 C3 Br1 118.64(19) . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 120.7(2) . . ?
C1 C6 C7 120.1(2) . . ?
N2 C7 C8 108.4(2) . . ?
N2 C7 C6 109.29(19) . . ?
C8 C7 C6 111.72(19) . . ?
N2 C7 C12 107.54(18) . . ?
C8 C7 C12 113.6(2) . . ?
C6 C7 C12 106.11(19) . . ?
C9 C8 C7 114.7(2) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 109.7(2) . . ?
C10 C9 Cl1 106.50(17) . . ?
C8 C9 Cl1 112.94(18) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
Cl1 C9 H9A 109.2 . . ?
N1 C10 C9 178.5(3) . . ?
C11 N2 C7 177.8(3) . . ?
O1 C12 O2 126.7(2) . . ?
O1 C12 C7 124.0(2) . . ?
O2 C12 C7 109.22(19) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 0.5(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 Br1 178.3(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
Br1 C3 C4 C5 -178.76(19) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 -175.9(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 C7 175.5(2) . . . . ?
C5 C6 C7 N2 -155.6(2) . . . . ?
C1 C6 C7 N2 28.4(3) . . . . ?
C5 C6 C7 C8 -35.7(3) . . . . ?
C1 C6 C7 C8 148.4(2) . . . . ?
C5 C6 C7 C12 88.7(3) . . . . ?
C1 C6 C7 C12 -87.3(3) . . . . ?
N2 C7 C8 C9 -51.2(3) . . . . ?
C6 C7 C8 C9 -171.7(2) . . . . ?
C12 C7 C8 C9 68.3(3) . . . . ?
C7 C8 C9 C10 177.1(2) . . . . ?
C7 C8 C9 Cl1 -64.3(2) . . . . ?
C8 C9 C10 N1 -42(12) . . . . ?
Cl1 C9 C10 N1 -165(12) . . . . ?
C8 C7 N2 C11 4(7) . . . . ?
C6 C7 N2 C11 126(7) . . . . ?
C12 C7 N2 C11 -119(7) . . . . ?
C13 O2 C12 O1 2.7(4) . . . . ?
C13 O2 C12 C7 -179.8(2) . . . . ?
N2 C7 C12 O1 -10.2(3) . . . . ?
C8 C7 C12 O1 -130.2(3) . . . . ?
C6 C7 C12 O1 106.6(3) . . . . ?
N2 C7 C12 O2 172.23(19) . . . . ?
C8 C7 C12 O2 52.3(3) . . . . ?
C6 C7 C12 O2 -70.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.053
