# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_DBrNq2AMT
_database_code_depnum_ccdc_archive 'CCDC 1446759'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Br N O2 S'
_chemical_formula_sum            'C15 H10 Br N O2 S'
_chemical_formula_weight         348.21

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3322(2)
_cell_length_b                   7.7451(2)
_cell_length_c                   12.5621(3)
_cell_angle_alpha                91.4380(6)
_cell_angle_beta                 90.0420(7)
_cell_angle_gamma                96.9860(7)
_cell_volume                     707.86(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.48

_exptl_crystal_description       PLATE
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    3.050
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25998
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.650
_diffrn_reflns_theta_max         28.396
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3546
_reflns_number_gt                2325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0049(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3546
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   2.305
_refine_ls_restrained_S_all      2.305
_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_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
Br1 Br 0.70969(6) 0.50253(4) 0.89183(3) 0.0707(2) Uani 1 1 d . . . . .
S1 S 1.16519(15) 1.12732(13) 0.82912(8) 0.0734(3) Uani 1 1 d . . . . .
O1 O 0.7418(3) 0.2482(3) 0.71779(18) 0.0642(7) Uani 1 1 d . . . . .
O2 O 0.7601(4) 0.8724(3) 0.55019(18) 0.0872(9) Uani 1 1 d . . . . .
N1 N 0.7633(3) 0.8676(3) 0.75526(18) 0.0385(6) Uani 1 1 d . . . . .
H1 H 0.7218 0.9469 0.7188 0.046 Uiso 1 1 calc R U . . .
C1 C 0.7452(4) 0.3928(4) 0.6791(2) 0.0424(8) Uani 1 1 d . . . . .
C2 C 0.7427(4) 0.5478(4) 0.7452(2) 0.0386(8) Uani 1 1 d . . . . .
C3 C 0.7557(4) 0.7117(4) 0.7058(2) 0.0335(7) Uani 1 1 d . . . . .
C4 C 0.7549(4) 0.7278(4) 0.5863(2) 0.0439(8) Uani 1 1 d . . . . .
C5 C 0.7494(5) 0.5888(4) 0.4082(3) 0.0535(9) Uani 1 1 d . . . . .
H5 H 0.7511 0.6980 0.3789 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7464(5) 0.4440(5) 0.3429(3) 0.0615(10) Uani 1 1 d . . . . .
H6 H 0.7448 0.4548 0.2694 0.074 Uiso 1 1 calc R U . . .
C7 C 0.7456(5) 0.2840(5) 0.3862(3) 0.0653(11) Uani 1 1 d . . . . .
H7 H 0.7444 0.1858 0.3419 0.078 Uiso 1 1 calc R U . . .
C8 C 0.7465(5) 0.2667(4) 0.4947(3) 0.0593(10) Uani 1 1 d . . . . .
H8 H 0.7456 0.1570 0.5232 0.071 Uiso 1 1 calc R U . . .
C9 C 0.7487(4) 0.4111(4) 0.5619(2) 0.0383(8) Uani 1 1 d . . . . .
C10 C 0.7498(4) 0.5730(4) 0.5173(2) 0.0378(7) Uani 1 1 d . . . . .
C11 C 0.8309(4) 0.9240(4) 0.8615(2) 0.0407(8) Uani 1 1 d . . . . .
H11A H 0.7798 0.8402 0.9129 0.049 Uiso 1 1 calc R U . . .
H11B H 0.7891 1.0350 0.8799 0.049 Uiso 1 1 calc R U . . .
C12 C 1.0359(4) 0.9420(4) 0.8681(2) 0.0394(8) Uani 1 1 d . . . . .
C13 C 1.1467(4) 0.8157(4) 0.9005(2) 0.0300(7) Uani 1 1 d . . . . .
H13 H 1.1036 0.7049 0.9234 0.036 Uiso 1 1 calc R U . . .
C14 C 1.3315(5) 0.8840(5) 0.8926(3) 0.0643(11) Uani 1 1 d . . . . .
H14 H 1.4266 0.8219 0.9123 0.077 Uiso 1 1 calc R U . . .
C15 C 1.3618(5) 1.0441(6) 0.8550(3) 0.0682(11) Uani 1 1 d . . . . .
H15 H 1.4783 1.1032 0.8443 0.082 Uiso 1 1 calc R U . . .


_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 C2 1.894(3) . ?
S1 C15 1.684(4) . ?
S1 C12 1.704(3) . ?
O1 C1 1.230(3) . ?
O2 C4 1.215(3) . ?
N1 C3 1.339(3) . ?
N1 C11 1.461(3) . ?
N1 H1 0.8600 . ?
C1 C2 1.444(4) . ?
C1 C9 1.482(4) . ?
C2 C3 1.367(4) . ?
C3 C4 1.509(4) . ?
C4 C10 1.459(4) . ?
C5 C6 1.371(5) . ?
C5 C10 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(4) . ?
C11 C12 1.495(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.412(4) . ?
C13 C14 1.398(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.331(5) . ?
C14 H14 0.9300 . ?
C15 H15 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
C15 S1 C12 91.69(18) . . ?
C3 N1 C11 130.1(2) . . ?
C3 N1 H1 114.9 . . ?
C11 N1 H1 114.9 . . ?
O1 C1 C2 121.6(3) . . ?
O1 C1 C9 120.1(3) . . ?
C2 C1 C9 118.3(2) . . ?
C3 C2 C1 123.5(3) . . ?
C3 C2 Br1 122.8(2) . . ?
C1 C2 Br1 113.72(19) . . ?
N1 C3 C2 131.1(3) . . ?
N1 C3 C4 111.4(2) . . ?
C2 C3 C4 117.4(3) . . ?
O2 C4 C10 121.7(3) . . ?
O2 C4 C3 118.1(3) . . ?
C10 C4 C3 120.2(2) . . ?
C6 C5 C10 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C10 C5 H5 119.9 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 C1 120.6(3) . . ?
C8 C9 C1 120.8(3) . . ?
C5 C10 C9 120.4(3) . . ?
C5 C10 C4 119.9(3) . . ?
C9 C10 C4 119.7(3) . . ?
N1 C11 C12 112.1(2) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 127.4(3) . . ?
C13 C12 S1 111.7(2) . . ?
C11 C12 S1 120.8(2) . . ?
C14 C13 C12 109.0(3) . . ?
C14 C13 H13 125.5 . . ?
C12 C13 H13 125.5 . . ?
C15 C14 C13 115.3(3) . . ?
C15 C14 H14 122.4 . . ?
C13 C14 H14 122.4 . . ?
C14 C15 S1 112.3(3) . . ?
C14 C15 H15 123.9 . . ?
S1 C15 H15 123.9 . . ?

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
O1 C1 C2 C3 176.5(3) . . . . ?
C9 C1 C2 C3 -4.5(4) . . . . ?
O1 C1 C2 Br1 -5.8(4) . . . . ?
C9 C1 C2 Br1 173.1(2) . . . . ?
C11 N1 C3 C2 27.2(5) . . . . ?
C11 N1 C3 C4 -155.3(3) . . . . ?
C1 C2 C3 N1 -176.8(3) . . . . ?
Br1 C2 C3 N1 5.8(5) . . . . ?
C1 C2 C3 C4 5.8(4) . . . . ?
Br1 C2 C3 C4 -171.6(2) . . . . ?
N1 C3 C4 O2 -0.3(4) . . . . ?
C2 C3 C4 O2 177.5(3) . . . . ?
N1 C3 C4 C10 179.1(3) . . . . ?
C2 C3 C4 C10 -3.0(4) . . . . ?
C10 C5 C6 C7 -0.6(5) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C7 C8 C9 C1 178.5(3) . . . . ?
O1 C1 C9 C10 179.0(3) . . . . ?
C2 C1 C9 C10 0.1(4) . . . . ?
O1 C1 C9 C8 0.6(5) . . . . ?
C2 C1 C9 C8 -178.3(3) . . . . ?
C6 C5 C10 C9 0.5(5) . . . . ?
C6 C5 C10 C4 179.4(3) . . . . ?
C8 C9 C10 C5 -0.2(5) . . . . ?
C1 C9 C10 C5 -178.7(3) . . . . ?
C8 C9 C10 C4 -179.1(3) . . . . ?
C1 C9 C10 C4 2.4(4) . . . . ?
O2 C4 C10 C5 -0.5(5) . . . . ?
C3 C4 C10 C5 -179.9(3) . . . . ?
O2 C4 C10 C9 178.4(3) . . . . ?
C3 C4 C10 C9 -1.1(4) . . . . ?
C3 N1 C11 C12 73.2(4) . . . . ?
N1 C11 C12 C13 -93.4(3) . . . . ?
N1 C11 C12 S1 83.8(3) . . . . ?
C15 S1 C12 C13 -0.3(2) . . . . ?
C15 S1 C12 C11 -177.9(2) . . . . ?
C11 C12 C13 C14 178.6(3) . . . . ?
S1 C12 C13 C14 1.2(3) . . . . ?
C12 C13 C14 C15 -1.8(4) . . . . ?
C13 C14 C15 S1 1.6(4) . . . . ?
C12 S1 C15 C14 -0.7(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
C13 H13 Br1 0.93 3.13 3.776(3) 127.7 .
N1 H1 O1 0.86 2.32 3.019(3) 138.6 1_565
C11 H11A Br1 0.97 2.61 3.309(3) 129.1 .
C15 H15 O1 0.93 2.66 3.508(4) 151.5 1_665
N1 H1 O1 0.86 2.32 3.019(3) 138.6 1_565
C11 H11A Br1 0.97 2.61 3.309(3) 129.1 .
C13 H13 Br1 0.93 3.13 3.776(3) 127.7 .
C15 H15 O1 0.93 2.66 3.508(4) 151.5 1_665

_refine_diff_density_max         0.692
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_mo_dbrnq2epa_0m
_database_code_depnum_ccdc_archive 'CCDC 1446760'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 Br N2 O2'
_chemical_formula_sum            'C17 H13 Br N2 O2'
_chemical_formula_weight         357.20

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   25.2419(4)
_cell_length_b                   4.46860(10)
_cell_length_c                   27.7323(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.0900(8)
_cell_angle_gamma                90.00
_cell_volume                     2973.47(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5913
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      24.23

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    2.773
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15850
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2623
_reflns_number_gt                2001
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0000P)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    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00091(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2623
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.651
_refine_ls_restrained_S_all      1.651
_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 0.213712(16) 0.04037(10) 0.054206(16) 0.0688(2) Uani 1 1 d . . .
O2 O 0.03096(11) 0.5767(6) 0.05839(9) 0.0664(8) Uani 1 1 d . . .
O1 O 0.24301(11) 0.3118(6) 0.15560(9) 0.0685(8) Uani 1 1 d . . .
N2 N 0.05070(13) -0.1324(6) -0.13759(12) 0.0513(8) Uani 1 1 d . . .
C13 C 0.10149(16) -0.0369(7) -0.10983(13) 0.0415(9) Uani 1 1 d . . .
C11 C 0.08638(15) 0.0088(7) -0.02522(13) 0.0449(9) Uani 1 1 d . . .
H11A H 0.0525 -0.1046 -0.0402 0.054 Uiso 1 1 calc R . .
H11B H 0.1156 -0.1318 -0.0086 0.054 Uiso 1 1 calc R . .
C16 C 0.0938(2) -0.4240(9) -0.18696(15) 0.0632(12) Uani 1 1 d . . .
H16 H 0.0899 -0.5562 -0.2137 0.076 Uiso 1 1 calc R . .
C17 C 0.04793(18) -0.3222(9) -0.17530(15) 0.0600(11) Uani 1 1 d . . .
H17 H 0.0130 -0.3895 -0.1948 0.072 Uiso 1 1 calc R . .
C12 C 0.10235(15) 0.1692(7) -0.06719(13) 0.0497(10) Uani 1 1 d . . .
H12A H 0.0766 0.3328 -0.0801 0.060 Uiso 1 1 calc R . .
H12B H 0.1394 0.2535 -0.0533 0.060 Uiso 1 1 calc R . .
N1 N 0.07775(11) 0.2116(6) 0.01226(10) 0.0487(8) Uani 1 1 d . . .
H1 H 0.0446 0.2849 0.0041 0.058 Uiso 1 1 calc R . .
C3 C 0.11099(14) 0.3084(7) 0.05718(12) 0.0349(8) Uani 1 1 d . . .
C4 C 0.07938(14) 0.5125(7) 0.08188(12) 0.0393(8) Uani 1 1 d . . .
C10 C 0.10623(13) 0.6331(7) 0.13296(11) 0.0333(8) Uani 1 1 d . . .
C5 C 0.07682(15) 0.8163(7) 0.15589(13) 0.0420(9) Uani 1 1 d . . .
H5 H 0.0400 0.8662 0.1389 0.050 Uiso 1 1 calc R . .
C6 C 0.10247(16) 0.9242(8) 0.20401(13) 0.0494(9) Uani 1 1 d . . .
H6 H 0.0829 1.0474 0.2196 0.059 Uiso 1 1 calc R . .
C7 C 0.15721(16) 0.8496(8) 0.22921(14) 0.0512(10) Uani 1 1 d . . .
H7 H 0.1742 0.9202 0.2619 0.061 Uiso 1 1 calc R . .
C14 C 0.14912(16) -0.1313(8) -0.11941(14) 0.0518(10) Uani 1 1 d . . .
H14 H 0.1838 -0.0631 -0.0995 0.062 Uiso 1 1 calc R . .
C15 C 0.1449(2) -0.3277(9) -0.15863(17) 0.0639(12) Uani 1 1 d . . .
H15 H 0.1767 -0.3935 -0.1656 0.077 Uiso 1 1 calc R . .
C8 C 0.18672(15) 0.6722(8) 0.20633(13) 0.0485(9) Uani 1 1 d . . .
H8 H 0.2238 0.6263 0.2234 0.058 Uiso 1 1 calc R . .
C9 C 0.16168(13) 0.5608(7) 0.15797(12) 0.0345(8) Uani 1 1 d . . .
C1 C 0.19406(15) 0.3699(7) 0.13328(13) 0.0433(9) Uani 1 1 d . . .
C2 C 0.16591(14) 0.2583(7) 0.08225(13) 0.0391(8) Uani 1 1 d . . .


_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 C2 1.895(3) . ?
O2 C4 1.227(4) . ?
O1 C1 1.226(4) . ?
N2 C17 1.331(4) . ?
N2 C13 1.344(4) . ?
C13 C14 1.376(5) . ?
C13 C12 1.494(4) . ?
C11 N1 1.446(4) . ?
C11 C12 1.524(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C16 C15 1.356(5) . ?
C16 C17 1.372(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N1 C3 1.339(4) . ?
N1 H1 0.8600 . ?
C3 C2 1.363(4) . ?
C3 C4 1.509(4) . ?
C4 C10 1.470(4) . ?
C10 C5 1.385(4) . ?
C10 C9 1.393(4) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(5) . ?
C7 H7 0.9300 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9300 . ?
C9 C1 1.487(5) . ?
C1 C2 1.460(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
C17 N2 C13 117.4(3) . . ?
N2 C13 C14 121.8(3) . . ?
N2 C13 C12 115.2(3) . . ?
C14 C13 C12 122.9(3) . . ?
N1 C11 C12 112.9(3) . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C15 C16 C17 118.6(4) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N2 C17 C16 123.6(4) . . ?
N2 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
C13 C12 C11 111.8(3) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C3 N1 C11 132.9(3) . . ?
C3 N1 H1 113.6 . . ?
C11 N1 H1 113.6 . . ?
N1 C3 C2 131.8(3) . . ?
N1 C3 C4 110.5(3) . . ?
C2 C3 C4 117.7(3) . . ?
O2 C4 C10 120.7(3) . . ?
O2 C4 C3 118.7(3) . . ?
C10 C4 C3 120.6(3) . . ?
C5 C10 C9 120.5(3) . . ?
C5 C10 C4 120.4(3) . . ?
C9 C10 C4 119.1(3) . . ?
C6 C5 C10 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C10 C5 H5 120.2 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 119.1(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 C1 120.1(3) . . ?
C10 C9 C1 121.0(3) . . ?
O1 C1 C2 121.9(3) . . ?
O1 C1 C9 120.1(3) . . ?
C2 C1 C9 118.1(3) . . ?
C3 C2 C1 123.4(3) . . ?
C3 C2 Br1 123.5(3) . . ?
C1 C2 Br1 113.1(2) . . ?

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
C17 N2 C13 C14 -0.4(5) . . . . ?
C17 N2 C13 C12 -178.5(3) . . . . ?
C13 N2 C17 C16 0.1(5) . . . . ?
C15 C16 C17 N2 0.2(6) . . . . ?
N2 C13 C12 C11 68.9(4) . . . . ?
C14 C13 C12 C11 -109.1(4) . . . . ?
N1 C11 C12 C13 -170.2(3) . . . . ?
C12 C11 N1 C3 -94.8(4) . . . . ?
C11 N1 C3 C2 3.5(6) . . . . ?
C11 N1 C3 C4 -177.7(3) . . . . ?
N1 C3 C4 O2 -3.9(4) . . . . ?
C2 C3 C4 O2 175.1(3) . . . . ?
N1 C3 C4 C10 176.4(3) . . . . ?
C2 C3 C4 C10 -4.6(4) . . . . ?
O2 C4 C10 C5 1.4(5) . . . . ?
C3 C4 C10 C5 -178.9(3) . . . . ?
O2 C4 C10 C9 -178.5(3) . . . . ?
C3 C4 C10 C9 1.2(4) . . . . ?
C9 C10 C5 C6 -0.9(5) . . . . ?
C4 C10 C5 C6 179.2(3) . . . . ?
C10 C5 C6 C7 0.0(5) . . . . ?
C5 C6 C7 C8 1.1(5) . . . . ?
N2 C13 C14 C15 0.4(5) . . . . ?
C12 C13 C14 C15 178.3(3) . . . . ?
C17 C16 C15 C14 -0.2(6) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C6 C7 C8 C9 -1.2(5) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C7 C8 C9 C1 179.7(3) . . . . ?
C5 C10 C9 C8 0.8(5) . . . . ?
C4 C10 C9 C8 -179.3(3) . . . . ?
C5 C10 C9 C1 -178.6(3) . . . . ?
C4 C10 C9 C1 1.3(4) . . . . ?
C8 C9 C1 O1 -0.3(5) . . . . ?
C10 C9 C1 O1 179.1(3) . . . . ?
C8 C9 C1 C2 -179.9(3) . . . . ?
C10 C9 C1 C2 -0.5(5) . . . . ?
N1 C3 C2 C1 -175.7(3) . . . . ?
C4 C3 C2 C1 5.6(5) . . . . ?
N1 C3 C2 Br1 5.0(5) . . . . ?
C4 C3 C2 Br1 -173.8(2) . . . . ?
O1 C1 C2 C3 177.2(3) . . . . ?
C9 C1 C2 C3 -3.2(5) . . . . ?
O1 C1 C2 Br1 -3.4(4) . . . . ?
C9 C1 C2 Br1 176.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_mo_dbrnq3mpa_0m
_database_code_depnum_ccdc_archive 'CCDC 1446761'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 Br N2 O2'
_chemical_formula_sum            'C16 H11 Br N2 O2'
_chemical_formula_weight         343.18

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'
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'
N N 0.0061 0.0033 '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)/c

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

_cell_length_a                   12.9287(2)
_cell_length_b                   7.70260(10)
_cell_length_c                   14.6188(2)
_cell_angle_alpha                90.0000(6)
_cell_angle_beta                 109.1800(5)
_cell_angle_gamma                90.0000(6)
_cell_volume                     1375.00(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.86

_exptl_crystal_description       PLATE
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5144
_exptl_absorpt_correction_T_max  0.5956
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            47061
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2413
_reflns_number_gt                2179
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0508P)²+2.4096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0036(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2413
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.30107(3) -0.03797(6) 0.84682(3) 0.0544(2) Uani 1 1 d . . .
O2 O -0.0133(2) 0.3799(3) 0.8605(2) 0.0585(8) Uani 1 1 d . . .
O3 O 0.1326(2) -0.2667(3) 0.8691(2) 0.0523(7) Uani 1 1 d . . .
N1 N 0.1861(2) 0.3503(4) 0.8644(2) 0.0362(7) Uani 1 1 d . . .
H1 H 0.1435 0.4392 0.8511 0.043 Uiso 1 1 calc R . .
N2 N 0.4043(4) 0.5747(6) 1.1370(3) 0.0738(12) Uani 1 1 d . . .
C1 C 0.0998(3) -0.1173(4) 0.8684(2) 0.0333(7) Uani 1 1 d . . .
C2 C 0.1667(3) 0.0305(4) 0.8615(2) 0.0328(7) Uani 1 1 d . . .
C3 C 0.1345(3) 0.1992(4) 0.8642(2) 0.0286(7) Uani 1 1 d . . .
C4 C 0.0190(3) 0.2312(4) 0.8646(2) 0.0327(7) Uani 1 1 d . . .
C5 C -0.1554(3) 0.1142(5) 0.8718(3) 0.0415(8) Uani 1 1 d . . .
H5 H -0.1818 0.2272 0.8682 0.050 Uiso 1 1 calc R . .
C6 C -0.2207(3) -0.0238(5) 0.8796(3) 0.0474(9) Uani 1 1 d . . .
H6 H -0.2906 -0.0037 0.8822 0.057 Uiso 1 1 calc R . .
C7 C -0.1812(3) -0.1917(5) 0.8837(3) 0.0451(9) Uani 1 1 d . . .
H7 H -0.2253 -0.2846 0.8881 0.054 Uiso 1 1 calc R . .
C8 C -0.0772(3) -0.2222(5) 0.8811(2) 0.0405(8) Uani 1 1 d . . .
H8 H -0.0512 -0.3353 0.8841 0.049 Uiso 1 1 calc R . .
C9 C -0.0110(3) -0.0838(4) 0.8739(2) 0.0307(7) Uani 1 1 d . . .
C10 C -0.0515(3) 0.0840(4) 0.8693(2) 0.0308(7) Uani 1 1 d . . .
C11 C 0.3009(3) 0.3910(5) 0.8831(3) 0.0395(8) Uani 1 1 d . . .
H11A H 0.3066 0.4974 0.8496 0.047 Uiso 1 1 calc R . .
H11B H 0.3346 0.2986 0.8577 0.047 Uiso 1 1 calc R . .
C12 C 0.3617(3) 0.4125(5) 0.9897(2) 0.0350(7) Uani 1 1 d . . .
C13 C 0.4293(3) 0.2838(6) 1.0442(3) 0.0502(10) Uani 1 1 d . . .
H13 H 0.4390 0.1835 1.0126 0.060 Uiso 1 1 calc R . .
C14 C 0.4807(3) 0.2951(6) 1.1385(3) 0.0470(9) Uani 1 1 d . . .
H14 H 0.5246 0.2051 1.1725 0.056 Uiso 1 1 calc R . .
C15 C 0.4677(3) 0.4374(7) 1.1824(3) 0.0585(12) Uani 1 1 d . . .
H15 H 0.5040 0.4458 1.2487 0.070 Uiso 1 1 calc R . .
C16 C 0.3500(3) 0.5607(5) 1.0380(3) 0.0473(9) Uani 1 1 d . . .
H16 H 0.3060 0.6511 1.0045 0.057 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 C2 1.895(3) . ?
O2 C4 1.214(4) . ?
O3 C1 1.225(4) . ?
N1 C3 1.341(4) . ?
N1 C11 1.453(4) . ?
N1 H1 0.8600 . ?
N2 C15 1.369(6) . ?
N2 C16 1.390(6) . ?
C1 C2 1.453(5) . ?
C1 C9 1.483(5) . ?
C2 C3 1.369(5) . ?
C3 C4 1.516(5) . ?
C4 C10 1.470(5) . ?
C5 C10 1.376(5) . ?
C5 C6 1.385(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(5) . ?
C11 C12 1.506(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C16 1.377(5) . ?
C12 C13 1.387(5) . ?
C13 C14 1.322(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.308(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 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
C3 N1 C11 131.6(3) . . ?
C3 N1 H1 114.2 . . ?
C11 N1 H1 114.2 . . ?
C15 N2 C16 117.5(4) . . ?
O3 C1 C2 121.6(3) . . ?
O3 C1 C9 120.1(3) . . ?
C2 C1 C9 118.3(3) . . ?
C3 C2 C1 123.3(3) . . ?
C3 C2 Br1 124.5(3) . . ?
C1 C2 Br1 112.3(2) . . ?
N1 C3 C2 132.0(3) . . ?
N1 C3 C4 110.4(3) . . ?
C2 C3 C4 117.6(3) . . ?
O2 C4 C10 121.5(3) . . ?
O2 C4 C3 118.4(3) . . ?
C10 C4 C3 120.1(3) . . ?
C10 C5 C6 120.0(4) . . ?
C10 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 119.6(4) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 C1 121.0(3) . . ?
C8 C9 C1 119.9(3) . . ?
C5 C10 C9 120.8(3) . . ?
C5 C10 C4 119.8(3) . . ?
C9 C10 C4 119.4(3) . . ?
N1 C11 C12 111.8(3) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C16 C12 C13 116.9(3) . . ?
C16 C12 C11 120.9(3) . . ?
C13 C12 C11 122.2(3) . . ?
C14 C13 C12 123.9(4) . . ?
C14 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
C15 C14 C13 117.7(4) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 N2 124.3(4) . . ?
C14 C15 H15 117.9 . . ?
N2 C15 H15 117.9 . . ?
C12 C16 N2 119.7(4) . . ?
C12 C16 H16 120.1 . . ?
N2 C16 H16 120.1 . . ?

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
O3 C1 C2 C3 -177.4(3) . . . . ?
C9 C1 C2 C3 3.0(5) . . . . ?
O3 C1 C2 Br1 3.3(4) . . . . ?
C9 C1 C2 Br1 -176.2(2) . . . . ?
C11 N1 C3 C2 -15.6(6) . . . . ?
C11 N1 C3 C4 166.1(3) . . . . ?
C1 C2 C3 N1 175.7(3) . . . . ?
Br1 C2 C3 N1 -5.2(5) . . . . ?
C1 C2 C3 C4 -6.1(5) . . . . ?
Br1 C2 C3 C4 173.0(2) . . . . ?
N1 C3 C4 O2 3.4(4) . . . . ?
C2 C3 C4 O2 -175.2(3) . . . . ?
N1 C3 C4 C10 -177.0(3) . . . . ?
C2 C3 C4 C10 4.4(4) . . . . ?
C10 C5 C6 C7 -0.8(6) . . . . ?
C5 C6 C7 C8 0.8(6) . . . . ?
C6 C7 C8 C9 -0.3(6) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C7 C8 C9 C1 -178.3(3) . . . . ?
O3 C1 C9 C10 -177.4(3) . . . . ?
C2 C1 C9 C10 2.2(4) . . . . ?
O3 C1 C9 C8 0.7(5) . . . . ?
C2 C1 C9 C8 -179.7(3) . . . . ?
C6 C5 C10 C9 0.4(5) . . . . ?
C6 C5 C10 C4 -177.7(3) . . . . ?
C8 C9 C10 C5 0.1(5) . . . . ?
C1 C9 C10 C5 178.2(3) . . . . ?
C8 C9 C10 C4 178.2(3) . . . . ?
C1 C9 C10 C4 -3.7(5) . . . . ?
O2 C4 C10 C5 -1.8(5) . . . . ?
C3 C4 C10 C5 178.6(3) . . . . ?
O2 C4 C10 C9 -180.0(3) . . . . ?
C3 C4 C10 C9 0.4(4) . . . . ?
C3 N1 C11 C12 -85.1(4) . . . . ?
N1 C11 C12 C16 -75.9(4) . . . . ?
N1 C11 C12 C13 102.3(4) . . . . ?
C16 C12 C13 C14 1.0(6) . . . . ?
C11 C12 C13 C14 -177.3(4) . . . . ?
C12 C13 C14 C15 -0.8(7) . . . . ?
C13 C14 C15 N2 0.1(7) . . . . ?
C16 N2 C15 C14 0.3(7) . . . . ?
C13 C12 C16 N2 -0.5(6) . . . . ?
C11 C12 C16 N2 177.9(4) . . . . ?
C15 N2 C16 C12 -0.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_DBrNq2AMP_R
_database_code_depnum_ccdc_archive 'CCDC 1446762'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 Br N2 O2'
_chemical_formula_sum            'C16 H11 Br N2 O2'
_chemical_formula_weight         343.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_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                   4.8997(3)
_cell_length_b                   14.5291(8)
_cell_length_c                   19.5248(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.879(2)
_cell_angle_gamma                90
_cell_volume                     1379.93(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9637
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      68.24

_exptl_crystal_description       SHEET
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    4.116
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_T_max  0.772
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15644
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_av_R_equivalents  0.1625
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.802
_diffrn_reflns_theta_max         68.386
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2499
_reflns_number_gt                1931
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2499
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.1018
_refine_ls_wR_factor_ref         0.2760
_refine_ls_wR_factor_gt          0.2511
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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_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
Br1 Br 0.50184(16) 0.20497(4) 0.22696(4) 0.0457(4) Uani 1 1 d . . . . .
O1 O 0.0915(11) 0.0611(4) 0.1712(2) 0.0526(13) Uani 1 1 d . . . . .
O2 O 0.2254(12) 0.0525(4) 0.4476(3) 0.0625(16) Uani 1 1 d . . . . .
N4 N 0.9389(16) 0.2911(4) 0.4119(4) 0.0549(17) Uani 1 1 d . . . . .
N11 N 0.5417(13) 0.1740(4) 0.3810(3) 0.0426(13) Uani 1 1 d . . . . .
H11 H 0.6306 0.2085 0.3556 0.051 Uiso 1 1 calc R U . . .
C1 C 0.1151(13) 0.0620(4) 0.2345(3) 0.0376(14) Uani 1 1 d . . . . .
C2 C 0.3024(12) 0.1218(4) 0.2759(3) 0.0325(13) Uani 1 1 d . . . . .
C3 C 0.3551(12) 0.1207(4) 0.3464(3) 0.0320(13) Uani 1 1 d . . . . .
C4 C 0.1851(14) 0.0554(4) 0.3844(3) 0.0374(14) Uani 1 1 d . . . . .
C5 C -0.1830(14) -0.0629(4) 0.3791(4) 0.0442(16) Uani 1 1 d . . . . .
H5 H -0.1623 -0.0647 0.4270 0.053 Uiso 1 1 calc R U . . .
C6 C -0.3721(16) -0.1176(5) 0.3426(5) 0.054(2) Uani 1 1 d . . . . .
H6 H -0.4772 -0.1576 0.3659 0.064 Uiso 1 1 calc R U . . .
C7 C -0.4110(15) -0.1146(5) 0.2707(5) 0.0497(18) Uani 1 1 d . . . . .
H7 H -0.5442 -0.1513 0.2461 0.060 Uiso 1 1 calc R U . . .
C8 C -0.2489(14) -0.0564(4) 0.2361(4) 0.0450(16) Uani 1 1 d . . . . .
H8 H -0.2705 -0.0552 0.1881 0.054 Uiso 1 1 calc R U . . .
C9 C -0.0567(13) -0.0007(4) 0.2726(3) 0.0351(13) Uani 1 1 d . . . . .
C10 C -0.0184(13) -0.0037(4) 0.3448(3) 0.0356(14) Uani 1 1 d . . . . .
C12 C 0.6231(16) 0.1844(5) 0.4551(4) 0.0439(16) Uani 1 1 d . . . . .
H12A H 0.6962 0.1266 0.4743 0.053 Uiso 1 1 calc R U . . .
H12B H 0.4642 0.2006 0.4778 0.053 Uiso 1 1 calc R U . . .
C13 C 0.8378(16) 0.2584(5) 0.4674(4) 0.0454(16) Uani 1 1 d . . . . .
C14 C 0.912(2) 0.2915(6) 0.5327(5) 0.066(3) Uani 1 1 d . . . . .
H14 H 0.8313 0.2678 0.5697 0.079 Uiso 1 1 calc R U . . .
C15 C 1.106(3) 0.3600(7) 0.5433(6) 0.085(3) Uani 1 1 d . . . . .
H15 H 1.1585 0.3829 0.5874 0.102 Uiso 1 1 calc R U . . .
C16 C 1.219(2) 0.3935(6) 0.4890(6) 0.076(3) Uani 1 1 d . . . . .
H16 H 1.3529 0.4391 0.4946 0.091 Uiso 1 1 calc R U . . .
C17 C 1.1277(19) 0.3574(6) 0.4233(5) 0.064(2) Uani 1 1 d . . . . .
H17 H 1.2035 0.3811 0.3856 0.077 Uiso 1 1 calc R U . . .


_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 C2 1.885(5) . ?
O1 C1 1.227(8) . ?
O2 C4 1.227(8) . ?
N4 C17 1.335(10) . ?
N4 C13 1.332(10) . ?
N11 C3 1.321(9) . ?
N11 C12 1.461(9) . ?
N11 H11 0.8600 . ?
C1 C2 1.439(9) . ?
C1 C9 1.497(8) . ?
C2 C3 1.370(9) . ?
C3 C4 1.514(7) . ?
C4 C10 1.464(9) . ?
C5 C6 1.355(11) . ?
C5 C10 1.403(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.401(9) . ?
C12 C13 1.503(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.372(12) . ?
C14 C15 1.375(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.344(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.408(15) . ?
C16 H16 0.9300 . ?
C17 H17 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
C17 N4 C13 116.1(8) . . ?
C3 N11 C12 131.1(5) . . ?
C3 N11 H11 114.5 . . ?
C12 N11 H11 114.5 . . ?
O1 C1 C2 123.2(6) . . ?
O1 C1 C9 120.2(6) . . ?
C2 C1 C9 116.6(5) . . ?
C3 C2 C1 126.0(5) . . ?
C3 C2 Br1 118.0(4) . . ?
C1 C2 Br1 115.9(4) . . ?
N11 C3 C2 122.9(5) . . ?
N11 C3 C4 120.3(6) . . ?
C2 C3 C4 116.8(5) . . ?
O2 C4 C10 121.9(5) . . ?
O2 C4 C3 118.9(6) . . ?
C10 C4 C3 119.2(5) . . ?
C6 C5 C10 120.3(7) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 H5 119.8 . . ?
C5 C6 C7 120.8(6) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 119.4(7) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 120.2(7) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.3(6) . . ?
C8 C9 C1 119.5(6) . . ?
C10 C9 C1 120.2(6) . . ?
C5 C10 C9 118.9(6) . . ?
C5 C10 C4 120.1(6) . . ?
C9 C10 C4 120.9(5) . . ?
N11 C12 C13 109.5(6) . . ?
N11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
N11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
N4 C13 C14 123.3(8) . . ?
N4 C13 C12 116.6(6) . . ?
C14 C13 C12 120.1(7) . . ?
C15 C14 C13 119.7(9) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 119.1(10) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 117.9(8) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
N4 C17 C16 124.0(9) . . ?
N4 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?

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
O1 C1 C2 C3 -174.2(6) . . . . ?
C9 C1 C2 C3 6.3(9) . . . . ?
O1 C1 C2 Br1 3.0(8) . . . . ?
C9 C1 C2 Br1 -176.6(4) . . . . ?
C12 N11 C3 C2 178.5(7) . . . . ?
C12 N11 C3 C4 -0.7(10) . . . . ?
C1 C2 C3 N11 175.9(6) . . . . ?
Br1 C2 C3 N11 -1.2(8) . . . . ?
C1 C2 C3 C4 -4.8(8) . . . . ?
Br1 C2 C3 C4 178.0(4) . . . . ?
N11 C3 C4 O2 -0.5(9) . . . . ?
C2 C3 C4 O2 -179.8(6) . . . . ?
N11 C3 C4 C10 -179.3(5) . . . . ?
C2 C3 C4 C10 1.4(8) . . . . ?
C10 C5 C6 C7 -1.4(10) . . . . ?
C5 C6 C7 C8 1.5(10) . . . . ?
C6 C7 C8 C9 -1.5(10) . . . . ?
C7 C8 C9 C10 1.4(9) . . . . ?
C7 C8 C9 C1 -179.6(6) . . . . ?
O1 C1 C9 C8 -2.7(9) . . . . ?
C2 C1 C9 C8 176.9(5) . . . . ?
O1 C1 C9 C10 176.3(6) . . . . ?
C2 C1 C9 C10 -4.2(8) . . . . ?
C6 C5 C10 C9 1.2(9) . . . . ?
C6 C5 C10 C4 179.8(6) . . . . ?
C8 C9 C10 C5 -1.2(8) . . . . ?
C1 C9 C10 C5 179.8(5) . . . . ?
C8 C9 C10 C4 -179.8(5) . . . . ?
C1 C9 C10 C4 1.2(8) . . . . ?
O2 C4 C10 C5 2.9(9) . . . . ?
C3 C4 C10 C5 -178.3(5) . . . . ?
O2 C4 C10 C9 -178.5(6) . . . . ?
C3 C4 C10 C9 0.2(8) . . . . ?
C3 N11 C12 C13 -177.2(6) . . . . ?
C17 N4 C13 C14 2.2(12) . . . . ?
C17 N4 C13 C12 179.4(7) . . . . ?
N11 C12 C13 N4 -8.5(9) . . . . ?
N11 C12 C13 C14 168.8(8) . . . . ?
N4 C13 C14 C15 -2.1(15) . . . . ?
C12 C13 C14 C15 -179.2(9) . . . . ?
C13 C14 C15 C16 0.3(18) . . . . ?
C14 C15 C16 C17 1.1(17) . . . . ?
C13 N4 C17 C16 -0.7(13) . . . . ?
C15 C16 C17 N4 -0.9(16) . . . . ?

_refine_diff_density_max         1.291
_refine_diff_density_min         -1.804
_refine_diff_density_rms         0.252

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_cu_DBrNq2AET_0m
_database_code_depnum_ccdc_archive 'CCDC 1446920'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Br N O2 S'
_chemical_formula_sum            'C16 H12 Br N O2 S'
_chemical_formula_weight         362.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

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

_cell_length_a                   23.3217(11)
_cell_length_b                   4.4264(2)
_cell_length_c                   14.6193(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.381(3)
_cell_angle_gamma                90
_cell_volume                     1508.73(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4235
_cell_measurement_theta_min      3.79
_cell_measurement_theta_max      68.04

_exptl_crystal_description       Plate
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    5.037
_shelx_estimated_absorpt_T_min   0.464
_shelx_estimated_absorpt_T_max   0.625
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.511
_exptl_absorpt_correction_T_max  0.595
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7556
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.792
_diffrn_reflns_theta_max         68.470
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             2600
_reflns_number_gt                1940
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.871
_reflns_Friedel_fraction_full    0.876

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.09(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2600
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2459
_refine_ls_wR_factor_gt          0.2109
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_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_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
Br1 Br 0.99432(7) 0.6936(4) 0.74405(8) 0.0898(7) Uani 1 1 d . . . . .
S2 S 1.1258(3) 0.9411(18) 0.9330(5) 0.125(2) Uani 1 1 d . . . . .
O1 O 0.9152(6) 0.337(3) 0.6305(7) 0.089(3) Uani 1 1 d . . . . .
O2 O 0.8272(5) 0.416(3) 0.9638(7) 0.082(3) Uani 1 1 d . . . . .
N1 N 0.9232(5) 0.694(2) 0.9407(8) 0.058(2) Uani 1 1 d . . . . .
H1 H 0.9007 0.6892 0.9864 0.070 Uiso 1 1 calc R U . . .
C1 C 0.8970(6) 0.351(3) 0.7096(8) 0.060(3) Uani 1 1 d . . . . .
C2 C 0.9249(5) 0.513(3) 0.7811(8) 0.051(2) Uani 1 1 d . . . . .
C3 C 0.9032(5) 0.547(3) 0.8683(7) 0.050(2) Uani 1 1 d . . . . .
C4 C 0.8466(5) 0.391(3) 0.8882(8) 0.057(3) Uani 1 1 d . . . . .
C5 C 0.7671(7) 0.061(4) 0.8320(12) 0.074(4) Uani 1 1 d . . . . .
H5 H 0.7516 0.0718 0.8900 0.089 Uiso 1 1 calc R U . . .
C6 C 0.7394(8) -0.100(4) 0.7645(14) 0.083(5) Uani 1 1 d . . . . .
H6 H 0.7041 -0.1898 0.7752 0.100 Uiso 1 1 calc R U . . .
C7 C 0.7649(8) -0.129(4) 0.6782(15) 0.089(5) Uani 1 1 d . . . . .
H7 H 0.7477 -0.2485 0.6330 0.106 Uiso 1 1 calc R U . . .
C8 C 0.8140(7) 0.017(3) 0.6616(11) 0.076(4) Uani 1 1 d . . . . .
H8 H 0.8296 0.0036 0.6038 0.091 Uiso 1 1 calc R U . . .
C9 C 0.8428(6) 0.190(3) 0.7299(9) 0.060(3) Uani 1 1 d . . . . .
C10 C 0.8183(6) 0.208(3) 0.8143(10) 0.058(3) Uani 1 1 d . . . . .
C11 C 0.9759(6) 0.865(3) 0.9588(9) 0.058(3) Uani 1 1 d . . . . .
H11A H 0.9697 1.0076 1.0079 0.070 Uiso 1 1 calc R U . . .
H11B H 0.9856 0.9784 0.9046 0.070 Uiso 1 1 calc R U . . .
C12 C 1.0256(6) 0.656(3) 0.9855(11) 0.065(3) Uani 1 1 d . . . . .
H12A H 1.0146 0.5304 1.0366 0.079 Uiso 1 1 calc R U . . .
H12B H 1.0337 0.5239 0.9345 0.079 Uiso 1 1 calc R U . . .
C13 C 1.0793(6) 0.830(3) 1.0120(11) 0.063(3) Uani 1 1 d . . . . .
C14 C 1.0956(5) 0.937(3) 1.1031(10) 0.062(3) Uani 1 1 d . . . . .
H14 H 1.0752 0.9052 1.1561 0.075 Uiso 1 1 calc R U . . .
C15 C 1.1472(10) 1.096(6) 1.097(3) 0.132(11) Uani 1 1 d . . . . .
H15 H 1.1659 1.1777 1.1482 0.158 Uiso 1 1 calc R U . . .
C16 C 1.1679(11) 1.124(6) 1.013(4) 0.155(17) Uani 1 1 d . . . . .
H16 H 1.2012 1.2300 1.0001 0.186 Uiso 1 1 calc R U . . .


_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 C2 1.896(12) . ?
S2 C13 1.677(16) . ?
S2 C16 1.72(4) . ?
O1 C1 1.243(17) . ?
O2 C4 1.208(17) . ?
N1 C3 1.319(16) . ?
N1 C11 1.460(18) . ?
N1 H1 0.8600 . ?
C1 C2 1.413(18) . ?
C1 C9 1.49(2) . ?
C2 C3 1.392(16) . ?
C3 C4 1.523(17) . ?
C4 C10 1.492(19) . ?
C5 C6 1.37(3) . ?
C5 C10 1.39(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.41(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.34(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.414(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.37(2) . ?
C11 C12 1.53(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.51(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.45(2) . ?
C14 C15 1.40(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.33(5) . ?
C15 H15 0.9300 . ?
C16 H16 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
C13 S2 C16 92.1(16) . . ?
C3 N1 C11 132.9(11) . . ?
C3 N1 H1 113.5 . . ?
C11 N1 H1 113.5 . . ?
O1 C1 C2 123.4(14) . . ?
O1 C1 C9 118.2(13) . . ?
C2 C1 C9 118.3(11) . . ?
C3 C2 C1 124.1(12) . . ?
C3 C2 Br1 123.2(9) . . ?
C1 C2 Br1 112.6(9) . . ?
N1 C3 C2 131.2(11) . . ?
N1 C3 C4 111.2(10) . . ?
C2 C3 C4 117.6(10) . . ?
O2 C4 C10 122.8(12) . . ?
O2 C4 C3 118.7(12) . . ?
C10 C4 C3 118.5(11) . . ?
C6 C5 C10 120.2(16) . . ?
C6 C5 H5 119.9 . . ?
C10 C5 H5 119.9 . . ?
C5 C6 C7 119.3(16) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 119.8(16) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 121.7(17) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 117.7(14) . . ?
C10 C9 C1 121.7(12) . . ?
C8 C9 C1 120.7(13) . . ?
C9 C10 C5 121.2(13) . . ?
C9 C10 C4 119.7(12) . . ?
C5 C10 C4 119.1(13) . . ?
N1 C11 C12 111.3(10) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 112.1(11) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 126.6(13) . . ?
C14 C13 S2 112.0(11) . . ?
C12 C13 S2 121.2(12) . . ?
C15 C14 C13 108(2) . . ?
C15 C14 H14 125.9 . . ?
C13 C14 H14 125.9 . . ?
C16 C15 C14 116(3) . . ?
C16 C15 H15 122.0 . . ?
C14 C15 H15 122.0 . . ?
C15 C16 S2 112(2) . . ?
C15 C16 H16 124.1 . . ?
S2 C16 H16 124.1 . . ?

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
O1 C1 C2 C3 175.6(14) . . . . ?
C9 C1 C2 C3 -3.6(19) . . . . ?
O1 C1 C2 Br1 -2.4(18) . . . . ?
C9 C1 C2 Br1 178.4(9) . . . . ?
C11 N1 C3 C2 -3(2) . . . . ?
C11 N1 C3 C4 176.7(13) . . . . ?
C1 C2 C3 N1 -178.4(12) . . . . ?
Br1 C2 C3 N1 -1(2) . . . . ?
C1 C2 C3 C4 1.5(18) . . . . ?
Br1 C2 C3 C4 179.3(8) . . . . ?
N1 C3 C4 O2 -0.6(18) . . . . ?
C2 C3 C4 O2 179.5(13) . . . . ?
N1 C3 C4 C10 -178.8(11) . . . . ?
C2 C3 C4 C10 1.2(16) . . . . ?
C10 C5 C6 C7 3(3) . . . . ?
C5 C6 C7 C8 -4(3) . . . . ?
C6 C7 C8 C9 3(3) . . . . ?
C7 C8 C9 C10 -1(2) . . . . ?
C7 C8 C9 C1 -179.7(15) . . . . ?
O1 C1 C9 C10 -176.3(13) . . . . ?
C2 C1 C9 C10 2.9(18) . . . . ?
O1 C1 C9 C8 2.6(19) . . . . ?
C2 C1 C9 C8 -178.1(12) . . . . ?
C8 C9 C10 C5 0.1(18) . . . . ?
C1 C9 C10 C5 179.0(13) . . . . ?
C8 C9 C10 C4 -179.2(11) . . . . ?
C1 C9 C10 C4 -0.3(17) . . . . ?
C6 C5 C10 C9 -1(2) . . . . ?
C6 C5 C10 C4 177.8(14) . . . . ?
O2 C4 C10 C9 -180.0(14) . . . . ?
C3 C4 C10 C9 -1.8(17) . . . . ?
O2 C4 C10 C5 1(2) . . . . ?
C3 C4 C10 C5 178.9(12) . . . . ?
C3 N1 C11 C12 -82.3(18) . . . . ?
N1 C11 C12 C13 -175.4(12) . . . . ?
C11 C12 C13 C14 89.3(16) . . . . ?
C11 C12 C13 S2 -86.4(14) . . . . ?
C16 S2 C13 C14 0.7(13) . . . . ?
C16 S2 C13 C12 177.0(14) . . . . ?
C12 C13 C14 C15 -177.9(15) . . . . ?
S2 C13 C14 C15 -1.8(15) . . . . ?
C13 C14 C15 C16 2(3) . . . . ?
C14 C15 C16 S2 -2(3) . . . . ?
C13 S2 C16 C15 1(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 H12B Br1 0.97 3.01 3.592(16) 120.1 .
C14 H14 Br1 0.93 2.91 3.568(13) 128.7 2_575
C11 H11B Br1 0.97 2.68 3.268(14) 119.8 .
N1 H1 O2 0.86 2.12 2.586(14) 113.6 .
N1 H1 O1 0.86 2.13 2.790(15) 133.2 2_565
N1 H1 O1 0.86 2.13 2.790(15) 133.2 2_565
N1 H1 O2 0.86 2.12 2.586(14) 113.6 .
C11 H11B Br1 0.97 2.68 3.268(14) 119.8 .
C12 H12B Br1 0.97 3.01 3.592(16) 120.1 .
C14 H14 Br1 0.93 2.91 3.568(13) 128.7 2_575

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.087

_shelxl_version_number           2013-3

