# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1511240'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-bromo-12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 Br N2 O S'
_chemical_formula_weight         331.19

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'
S S 0.1246 0.1234 '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   P2(1)/n

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                   7.508(5)
_cell_length_b                   11.017(7)
_cell_length_c                   14.780(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.564(12)
_cell_angle_gamma                90.00
_cell_volume                     1222.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    565
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      20.70

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    3.524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5111
_exptl_absorpt_correction_T_max  0.5695
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3668
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0857
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2068
_reflns_number_gt                1201
_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)+(0.0840P)²+0.0000P] 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         2068
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_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 0.20561(12) 0.40015(6) 0.01901(6) 0.0715(4) Uani 1 1 d . . .
C1 C 0.2207(8) -0.2146(6) -0.0842(4) 0.0444(17) Uani 1 1 d . . .
C2 C 0.1846(9) -0.3001(6) -0.1525(6) 0.058(2) Uani 1 1 d . . .
H2 H 0.2039 -0.3825 -0.1433 0.069 Uiso 1 1 calc R . .
C3 C 0.1201(10) -0.2572(7) -0.2332(6) 0.068(2) Uani 1 1 d . . .
H3 H 0.0940 -0.3121 -0.2792 0.081 Uiso 1 1 calc R . .
C4 C 0.0921(10) -0.1332(7) -0.2489(5) 0.061(2) Uani 1 1 d . . .
H4 H 0.0489 -0.1070 -0.3048 0.074 Uiso 1 1 calc R . .
C5 C 0.1288(8) -0.0492(6) -0.1810(5) 0.0505(18) Uani 1 1 d . . .
H5 H 0.1112 0.0334 -0.1906 0.061 Uiso 1 1 calc R . .
C6 C 0.1931(8) -0.0926(5) -0.0977(5) 0.0428(16) Uani 1 1 d . . .
C7 C 0.3028(8) -0.0942(5) 0.0521(5) 0.0413(16) Uani 1 1 d . . .
C8 C 0.2150(9) 0.1057(5) -0.0086(5) 0.0444(16) Uani 1 1 d . . .
C9 C 0.2824(8) 0.1517(5) 0.0777(5) 0.0402(15) Uani 1 1 d . . .
C10 C 0.3485(8) 0.0700(5) 0.1441(5) 0.0408(16) Uani 1 1 d . . .
C11 C 0.4073(9) 0.1110(6) 0.2290(5) 0.0531(18) Uani 1 1 d . . .
H11 H 0.4487 0.0560 0.2721 0.064 Uiso 1 1 calc R . .
C12 C 0.4033(9) 0.2336(7) 0.2482(5) 0.061(2) Uani 1 1 d . . .
H12 H 0.4414 0.2611 0.3047 0.073 Uiso 1 1 calc R . .
C13 C 0.3427(9) 0.3165(6) 0.1838(5) 0.0531(19) Uani 1 1 d . . .
H13 H 0.3429 0.3991 0.1968 0.064 Uiso 1 1 calc R . .
C14 C 0.2824(8) 0.2761(5) 0.1007(5) 0.0437(17) Uani 1 1 d . . .
N1 N 0.2388(6) -0.0232(4) -0.0188(3) 0.0372(13) Uani 1 1 d . . .
N2 N 0.3561(7) -0.0543(4) 0.1296(4) 0.0454(14) Uani 1 1 d . . .
O1 O 0.1501(7) 0.1623(4) -0.0703(3) 0.0653(15) Uani 1 1 d . . .
S1 S 0.3034(3) -0.24836(14) 0.02461(14) 0.0541(5) 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
Br1 0.1011(7) 0.0292(4) 0.0841(7) 0.0080(4) -0.0138(5) 0.0071(4)
C1 0.052(4) 0.039(3) 0.042(5) 0.002(3) -0.007(3) -0.008(3)
C2 0.064(5) 0.041(4) 0.068(6) -0.014(4) 0.000(4) -0.011(4)
C3 0.063(5) 0.069(5) 0.070(6) -0.022(5) -0.006(4) -0.014(4)
C4 0.066(5) 0.069(5) 0.049(5) -0.004(4) -0.015(4) -0.004(4)
C5 0.059(5) 0.050(4) 0.042(5) -0.001(3) -0.015(4) -0.004(3)
C6 0.042(4) 0.039(3) 0.046(4) -0.003(3) -0.002(3) -0.005(3)
C7 0.040(4) 0.022(3) 0.062(5) 0.000(3) -0.010(3) 0.002(3)
C8 0.052(4) 0.027(3) 0.054(5) 0.010(3) -0.002(3) 0.004(3)
C9 0.037(4) 0.034(3) 0.049(5) -0.005(3) -0.011(3) -0.003(3)
C10 0.041(4) 0.031(3) 0.051(5) -0.006(3) -0.008(3) 0.001(3)
C11 0.058(4) 0.048(4) 0.054(5) 0.001(4) -0.009(3) -0.004(3)
C12 0.058(5) 0.066(5) 0.059(5) -0.022(4) -0.004(4) -0.013(4)
C13 0.059(5) 0.035(4) 0.065(6) -0.017(4) -0.005(4) 0.001(3)
C14 0.057(4) 0.019(3) 0.055(5) -0.002(3) 0.001(3) 0.000(3)
N1 0.043(3) 0.027(3) 0.042(3) 0.002(2) -0.011(2) 0.001(2)
N2 0.055(3) 0.031(3) 0.050(4) -0.002(3) -0.015(3) 0.001(3)
O1 0.111(4) 0.036(2) 0.049(3) 0.005(2) -0.030(3) 0.016(3)
S1 0.0742(12) 0.0259(8) 0.0619(13) 0.0035(8) -0.0094(9) 0.0011(8)

_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 C14 1.909(6) . ?
C1 C6 1.374(8) . ?
C1 C2 1.406(9) . ?
C1 S1 1.757(7) . ?
C2 C3 1.366(10) . ?
C3 C4 1.401(10) . ?
C4 C5 1.390(10) . ?
C5 C6 1.403(9) . ?
C6 N1 1.434(8) . ?
C7 N2 1.287(8) . ?
C7 N1 1.390(8) . ?
C7 S1 1.746(6) . ?
C8 O1 1.204(7) . ?
C8 N1 1.439(7) . ?
C8 C9 1.459(9) . ?
C9 C14 1.412(8) . ?
C9 C10 1.418(9) . ?
C10 N2 1.388(7) . ?
C10 C11 1.401(9) . ?
C11 C12 1.381(9) . ?
C12 C13 1.392(10) . ?
C13 C14 1.379(9) . ?

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 121.5(6) . . ?
C6 C1 S1 113.1(5) . . ?
C2 C1 S1 125.4(5) . . ?
C3 C2 C1 117.4(7) . . ?
C2 C3 C4 122.2(7) . . ?
C5 C4 C3 120.1(7) . . ?
C4 C5 C6 118.0(7) . . ?
C1 C6 C5 120.8(6) . . ?
C1 C6 N1 111.7(6) . . ?
C5 C6 N1 127.5(6) . . ?
N2 C7 N1 125.5(5) . . ?
N2 C7 S1 122.5(5) . . ?
N1 C7 S1 111.9(5) . . ?
O1 C8 N1 118.8(6) . . ?
O1 C8 C9 128.0(6) . . ?
N1 C8 C9 113.1(5) . . ?
C14 C9 C10 116.8(6) . . ?
C14 C9 C8 123.2(6) . . ?
C10 C9 C8 120.1(5) . . ?
N2 C10 C11 116.3(6) . . ?
N2 C10 C9 122.3(6) . . ?
C11 C10 C9 121.4(5) . . ?
C12 C11 C10 119.5(7) . . ?
C11 C12 C13 120.6(7) . . ?
C14 C13 C12 120.0(6) . . ?
C13 C14 C9 121.8(6) . . ?
C13 C14 Br1 115.3(4) . . ?
C9 C14 Br1 122.9(5) . . ?
C7 N1 C6 113.0(5) . . ?
C7 N1 C8 121.3(5) . . ?
C6 N1 C8 125.6(5) . . ?
C7 N2 C10 117.5(6) . . ?
C7 S1 C1 90.3(3) . . ?

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 -0.3(10) . . . . ?
S1 C1 C2 C3 179.8(5) . . . . ?
C1 C2 C3 C4 0.7(11) . . . . ?
C2 C3 C4 C5 -0.5(12) . . . . ?
C3 C4 C5 C6 -0.2(10) . . . . ?
C2 C1 C6 C5 -0.5(10) . . . . ?
S1 C1 C6 C5 179.5(5) . . . . ?
C2 C1 C6 N1 179.9(6) . . . . ?
S1 C1 C6 N1 -0.2(7) . . . . ?
C4 C5 C6 C1 0.7(10) . . . . ?
C4 C5 C6 N1 -179.7(6) . . . . ?
O1 C8 C9 C14 -0.9(12) . . . . ?
N1 C8 C9 C14 176.4(6) . . . . ?
O1 C8 C9 C10 177.5(7) . . . . ?
N1 C8 C9 C10 -5.1(9) . . . . ?
C14 C9 C10 N2 -179.7(6) . . . . ?
C8 C9 C10 N2 1.7(10) . . . . ?
C14 C9 C10 C11 1.2(9) . . . . ?
C8 C9 C10 C11 -177.3(6) . . . . ?
N2 C10 C11 C12 -179.9(6) . . . . ?
C9 C10 C11 C12 -0.9(10) . . . . ?
C10 C11 C12 C13 -0.5(10) . . . . ?
C11 C12 C13 C14 1.4(11) . . . . ?
C12 C13 C14 C9 -1.0(11) . . . . ?
C12 C13 C14 Br1 -179.5(5) . . . . ?
C10 C9 C14 C13 -0.3(10) . . . . ?
C8 C9 C14 C13 178.2(6) . . . . ?
C10 C9 C14 Br1 178.0(4) . . . . ?
C8 C9 C14 Br1 -3.4(9) . . . . ?
N2 C7 N1 C6 178.6(6) . . . . ?
S1 C7 N1 C6 -1.5(6) . . . . ?
N2 C7 N1 C8 -4.3(10) . . . . ?
S1 C7 N1 C8 175.6(4) . . . . ?
C1 C6 N1 C7 1.1(7) . . . . ?
C5 C6 N1 C7 -178.5(6) . . . . ?
C1 C6 N1 C8 -175.8(5) . . . . ?
C5 C6 N1 C8 4.6(10) . . . . ?
O1 C8 N1 C7 -176.0(6) . . . . ?
C9 C8 N1 C7 6.3(8) . . . . ?
O1 C8 N1 C6 0.6(10) . . . . ?
C9 C8 N1 C6 -177.0(5) . . . . ?
N1 C7 N2 C10 0.3(10) . . . . ?
S1 C7 N2 C10 -179.6(5) . . . . ?
C11 C10 N2 C7 -180.0(6) . . . . ?
C9 C10 N2 C7 1.0(9) . . . . ?
N2 C7 S1 C1 -179.0(6) . . . . ?
N1 C7 S1 C1 1.1(5) . . . . ?
C6 C1 S1 C7 -0.6(5) . . . . ?
C2 C1 S1 C7 179.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.097
