# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1843637'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          353.7
_chemical_formula_moiety         'C15 H10 Br N O3'
_chemical_formula_sum            'C15 H10 Br N O3'
_chemical_formula_weight         332.14

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'
Br Br -0.2901 2.4595 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4360(6)
_cell_length_b                   8.3742(4)
_cell_length_c                   14.1928(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.648(2)
_cell_angle_gamma                90
_cell_volume                     1354.74(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7260
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      25.73

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.385
_exptl_crystal_size_min          0.352
_exptl_absorpt_coefficient_mu    3.040
_shelx_estimated_absorpt_T_min   0.354
_shelx_estimated_absorpt_T_max   0.414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3619
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16762
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.787
_diffrn_reflns_theta_max         26.407
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2785
_reflns_number_gt                2292
_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    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material  
'MarvinSketch (ChemAxon, 2010) & PublCIF (Westrip, 2010)'
_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)+(0.0508P)²+0.4883P] 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_number_reflns         2785
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.27351(3) 0.20649(3) 0.31135(2) 0.06061(14) Uani 1 1 d . . . . .
O1 O -0.22358(19) 0.3435(3) -0.07046(14) 0.0689(6) Uani 1 1 d . . . . .
O2 O -0.0981(2) 0.1864(3) -0.12643(16) 0.0782(7) Uani 1 1 d . . . . .
O3 O 0.2699(2) 0.4986(3) 0.46243(14) 0.0734(6) Uani 1 1 d . . . . .
N1 N -0.1308(2) 0.2728(3) -0.06423(15) 0.0511(5) Uani 1 1 d . . . . .
C1 C -0.0517(2) 0.2942(3) 0.02223(17) 0.0403(5) Uani 1 1 d . . . . .
C2 C -0.0861(2) 0.3953(3) 0.09125(16) 0.0426(5) Uani 1 1 d . . . . .
H2 H -0.1587 0.4460 0.0842 0.051 Uiso 1 1 calc R U . . .
C3 C -0.0110(2) 0.4200(3) 0.17115(16) 0.0418(5) Uani 1 1 d . . . . .
H3 H -0.0332 0.4878 0.2185 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0976(2) 0.3444(3) 0.18142(16) 0.0386(5) Uani 1 1 d . . . . .
C7 C 0.17917(19) 0.3808(3) 0.26508(16) 0.0406(5) Uani 1 1 d . . . . .
C8 C 0.1939(2) 0.5234(3) 0.30368(18) 0.0465(6) Uani 1 1 d . . . . .
H8 H 0.1483 0.6060 0.2767 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2774(2) 0.5647(3) 0.38722(18) 0.0487(6) Uani 1 1 d . . . . .
C10 C 0.3676(2) 0.6881(3) 0.37410(17) 0.0422(5) Uani 1 1 d . . . . .
C11 C 0.3701(2) 0.7751(3) 0.29126(19) 0.0481(6) Uani 1 1 d . . . . .
H11 H 0.3135 0.7569 0.2416 0.058 Uiso 1 1 calc R U . . .
C12 C 0.4558(2) 0.8883(3) 0.2820(2) 0.0584(7) Uani 1 1 d . . . . .
H12 H 0.4565 0.9468 0.2264 0.070 Uiso 1 1 calc R U . . .
C13 C 0.5399(3) 0.9146(4) 0.3547(2) 0.0657(8) Uani 1 1 d . . . . .
H13 H 0.5979 0.9909 0.3482 0.079 Uiso 1 1 calc R U . . .
C6 C 0.0544(2) 0.2156(3) 0.03022(19) 0.0483(6) Uani 1 1 d . . . . .
H6 H 0.0760 0.1482 -0.0175 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1277(2) 0.2399(3) 0.11106(19) 0.0482(6) Uani 1 1 d . . . . .
H5 H 0.1987 0.1852 0.1187 0.058 Uiso 1 1 calc R U . . .
C14 C 0.5390(3) 0.8296(4) 0.4363(2) 0.0708(9) Uani 1 1 d . . . . .
H14 H 0.5966 0.8479 0.4852 0.085 Uiso 1 1 calc R U . . .
C15 C 0.4534(3) 0.7163(3) 0.4473(2) 0.0580(7) Uani 1 1 d . . . . .
H15 H 0.4532 0.6592 0.5035 0.070 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 C7 1.901(2) . ?
O1 N1 1.212(3) . ?
O2 N1 1.223(3) . ?
O3 C9 1.212(3) . ?
N1 C1 1.475(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.376(4) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(4) . ?
C4 C7 1.481(3) . ?
C7 C8 1.319(3) . ?
C8 C9 1.501(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.482(3) . ?
C10 C11 1.385(4) . ?
C10 C15 1.391(4) . ?
C11 C12 1.377(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(5) . ?
C13 H13 0.9300 . ?
C6 C5 1.380(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C14 C15 1.380(4) . ?
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
O1 N1 O2 123.6(2) . . ?
O1 N1 C1 118.4(2) . . ?
O2 N1 C1 118.0(2) . . ?
C2 C1 C6 122.5(2) . . ?
C2 C1 N1 118.4(2) . . ?
C6 C1 N1 119.2(2) . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 C7 119.3(2) . . ?
C5 C4 C7 121.9(2) . . ?
C8 C7 C4 124.8(2) . . ?
C8 C7 Br1 120.14(18) . . ?
C4 C7 Br1 114.94(16) . . ?
C7 C8 C9 126.0(2) . . ?
C7 C8 H8 117.0 . . ?
C9 C8 H8 117.0 . . ?
O3 C9 C10 121.9(2) . . ?
O3 C9 C8 120.3(2) . . ?
C10 C9 C8 117.8(2) . . ?
C11 C10 C15 118.9(2) . . ?
C11 C10 C9 122.4(2) . . ?
C15 C10 C9 118.7(2) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 119.7(3) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 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
O1 N1 C1 C2 -0.9(3) . . . . ?
O2 N1 C1 C2 177.9(2) . . . . ?
O1 N1 C1 C6 -179.6(2) . . . . ?
O2 N1 C1 C6 -0.7(3) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
N1 C1 C2 C3 -178.0(2) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C2 C3 C4 C7 176.3(2) . . . . ?
C3 C4 C7 C8 -38.0(3) . . . . ?
C5 C4 C7 C8 140.1(3) . . . . ?
C3 C4 C7 Br1 146.11(18) . . . . ?
C5 C4 C7 Br1 -35.8(3) . . . . ?
C4 C7 C8 C9 -178.7(2) . . . . ?
Br1 C7 C8 C9 -3.0(4) . . . . ?
C7 C8 C9 O3 -58.9(4) . . . . ?
C7 C8 C9 C10 121.3(3) . . . . ?
O3 C9 C10 C11 -173.8(3) . . . . ?
C8 C9 C10 C11 6.0(4) . . . . ?
O3 C9 C10 C15 6.9(4) . . . . ?
C8 C9 C10 C15 -173.3(2) . . . . ?
C15 C10 C11 C12 -0.4(4) . . . . ?
C9 C10 C11 C12 -179.8(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
N1 C1 C6 C5 178.9(2) . . . . ?
C1 C6 C5 C4 -2.0(4) . . . . ?
C3 C4 C5 C6 2.8(4) . . . . ?
C7 C4 C5 C6 -175.3(2) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C14 C15 C10 0.4(5) . . . . ?
C11 C10 C15 C14 0.0(4) . . . . ?
C9 C10 C15 C14 179.3(3) . . . . ?

_refine_diff_density_max         0.638
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.069

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
