# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_23
_database_code_depnum_ccdc_archive 'CCDC 1483759'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;
_audit_creation_date             2015-10-29
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C17 H16 Br N O3'
_chemical_formula_moiety         'C17 H16 Br N O3'
_chemical_formula_weight         362.22
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.5275(14)
_cell_length_b                   13.374(3)
_cell_length_c                   15.278(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1538.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4260
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736.00
_exptl_absorpt_coefficient_mu    2.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_T_max  0.922

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            7486
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_theta_max         25.394
_diffrn_reflns_theta_min         2.024
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2746
_reflns_number_gt                2251
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0723
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2746
_refine_ls_number_parameters     200
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0314P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(11)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br16 Br 0.25933(7) 0.83573(4) 0.63266(3) 0.02814(17) Uani 1 1 d . . . . .
O9 O 0.2810(4) 0.1806(3) 0.4100(2) 0.0309(9) Uani 1 1 d . . . . .
O10 O 0.0337(4) 0.0958(3) 0.4473(2) 0.0289(10) Uani 1 1 d . . . . .
O19 O 0.1936(4) 0.5166(3) 0.2822(2) 0.0272(9) Uani 1 1 d . . . . .
N7 N -0.2582(6) 0.3063(3) 0.3114(2) 0.0223(9) Uani 1 1 d . . . . .
C1 C 0.0015(6) 0.2202(5) 0.3396(3) 0.0237(13) Uani 1 1 d . . . . .
H1 H 0.0076 0.1812 0.2839 0.028 Uiso 1 1 calc R U . . .
C2 C 0.0518(6) 0.3292(4) 0.3144(3) 0.0224(12) Uani 1 1 d . . . . .
H2 H 0.1402 0.3287 0.2655 0.027 Uiso 1 1 calc R U . . .
C3 C -0.1253(7) 0.3668(5) 0.2816(4) 0.0228(14) Uani 1 1 d . . . . .
C4 C -0.2003(7) 0.4463(5) 0.2382(3) 0.0253(14) Uani 1 1 d . . . . .
H4 H -0.1399 0.5001 0.2106 0.030 Uiso 1 1 calc R U . . .
C5 C -0.3880(7) 0.4311(5) 0.2432(4) 0.0311(15) Uani 1 1 d . . . . .
H5 H -0.4753 0.4739 0.2185 0.037 Uiso 1 1 calc R U . . .
C6 C -0.4222(7) 0.3456(5) 0.2891(4) 0.0274(15) Uani 1 1 d . . . . .
H6 H -0.5355 0.3185 0.3028 0.033 Uiso 1 1 calc R U . . .
C8 C -0.1982(6) 0.2221(4) 0.3651(3) 0.0245(12) Uani 1 1 d . . . . .
H8A H -0.2591 0.1591 0.3490 0.029 Uiso 1 1 calc R U . . .
H8B H -0.2150 0.2351 0.4284 0.029 Uiso 1 1 calc R U . . .
C9 C 0.1210(6) 0.1664(5) 0.4024(3) 0.0250(13) Uani 1 1 d . . . . .
C10 C 0.1406(7) 0.0286(5) 0.5010(4) 0.0322(15) Uani 1 1 d . . . . .
H10A H 0.1777 0.0633 0.5544 0.039 Uiso 1 1 calc R U . . .
H10B H 0.2459 0.0076 0.4680 0.039 Uiso 1 1 calc R U . . .
H10C H 0.0701 -0.0304 0.5166 0.039 Uiso 1 1 calc R U . . .
C11 C 0.1216(6) 0.3933(4) 0.3905(3) 0.0218(12) Uani 1 1 d . . . . .
H11A H 0.0282 0.3990 0.4359 0.026 Uiso 1 1 calc R U . . .
H11B H 0.2257 0.3598 0.4172 0.026 Uiso 1 1 calc R U . . .
C12 C 0.1752(6) 0.4978(4) 0.3601(3) 0.0249(13) Uani 1 1 d . . . . .
C13 C 0.2062(6) 0.5764(4) 0.4282(3) 0.0212(12) Uani 1 1 d . . . . .
C14 C 0.2482(7) 0.6739(4) 0.4013(3) 0.0271(11) Uani 1 1 d . . . . .
H14 H 0.2630 0.6873 0.3407 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2687(7) 0.7508(4) 0.4607(3) 0.0268(12) Uani 1 1 d . . . . .
H15 H 0.2966 0.8165 0.4415 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2473(8) 0.7297(4) 0.5497(3) 0.0240(11) Uani 1 1 d . . . . .
C17 C 0.2131(7) 0.6336(4) 0.5785(3) 0.0256(13) Uani 1 1 d . . . . .
H17 H 0.2051 0.6197 0.6394 0.031 Uiso 1 1 calc R U . . .
C18 C 0.1905(6) 0.5579(4) 0.5179(3) 0.0278(14) Uani 1 1 d . . . . .
H18 H 0.1640 0.4922 0.5375 0.033 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br16 C16 1.904(5) . ?
O9 C9 1.224(6) . ?
O10 C9 1.339(7) . ?
O10 C10 1.460(6) . ?
O19 C12 1.223(6) . ?
N7 C3 1.365(6) . ?
N7 C6 1.384(6) . ?
N7 C8 1.465(6) . ?
C1 C9 1.500(7) . ?
C1 C8 1.553(6) . ?
C1 C2 1.555(8) . ?
C1 H1 1.0000 . ?
C2 C3 1.510(7) . ?
C2 C11 1.537(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.375(8) . ?
C4 C5 1.429(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.528(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.497(7) . ?
C13 C18 1.398(7) . ?
C13 C14 1.403(7) . ?
C14 C15 1.379(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(7) . ?
C17 C18 1.382(7) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C9 O10 C10 116.8(4) . . ?
C3 N7 C6 110.3(4) . . ?
C3 N7 C8 114.6(4) . . ?
C6 N7 C8 134.8(5) . . ?
C9 C1 C8 115.3(4) . . ?
C9 C1 C2 117.5(4) . . ?
C8 C1 C2 106.4(4) . . ?
C9 C1 H1 105.5 . . ?
C8 C1 H1 105.5 . . ?
C2 C1 H1 105.5 . . ?
C3 C2 C11 111.5(5) . . ?
C3 C2 C1 100.3(4) . . ?
C11 C2 C1 114.8(4) . . ?
C3 C2 H2 109.9 . . ?
C11 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
N7 C3 C4 108.6(4) . . ?
N7 C3 C2 109.8(5) . . ?
C4 C3 C2 141.3(5) . . ?
C3 C4 C5 105.7(6) . . ?
C3 C4 H4 127.2 . . ?
C5 C4 H4 127.2 . . ?
C6 C5 C4 109.5(6) . . ?
C6 C5 H5 125.3 . . ?
C4 C5 H5 125.3 . . ?
C5 C6 N7 106.0(5) . . ?
C5 C6 H6 127.0 . . ?
N7 C6 H6 127.0 . . ?
N7 C8 C1 99.8(4) . . ?
N7 C8 H8A 111.8 . . ?
C1 C8 H8A 111.8 . . ?
N7 C8 H8B 111.8 . . ?
C1 C8 H8B 111.8 . . ?
H8A C8 H8B 109.5 . . ?
O9 C9 O10 123.0(5) . . ?
O9 C9 C1 125.2(6) . . ?
O10 C9 C1 111.8(4) . . ?
O10 C10 H10A 109.5 . . ?
O10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O10 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C2 111.7(4) . . ?
C12 C11 H11A 109.3 . . ?
C2 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C2 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
O19 C12 C13 120.9(5) . . ?
O19 C12 C11 120.9(5) . . ?
C13 C12 C11 118.2(4) . . ?
C18 C13 C14 118.0(5) . . ?
C18 C13 C12 122.9(5) . . ?
C14 C13 C12 119.0(4) . . ?
C15 C14 C13 121.7(4) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 118.4(5) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 Br16 119.3(3) . . ?
C15 C16 Br16 119.4(4) . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C13 121.1(5) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?

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
C9 C1 C2 C3 -159.8(4) . . . . ?
C8 C1 C2 C3 -28.8(5) . . . . ?
C9 C1 C2 C11 -40.2(6) . . . . ?
C8 C1 C2 C11 90.9(5) . . . . ?
C6 N7 C3 C4 -0.7(5) . . . . ?
C8 N7 C3 C4 -175.5(4) . . . . ?
C6 N7 C3 C2 174.1(5) . . . . ?
C8 N7 C3 C2 -0.7(6) . . . . ?
C11 C2 C3 N7 -103.5(5) . . . . ?
C1 C2 C3 N7 18.5(5) . . . . ?
C11 C2 C3 C4 68.6(9) . . . . ?
C1 C2 C3 C4 -169.4(7) . . . . ?
N7 C3 C4 C5 0.1(6) . . . . ?
C2 C3 C4 C5 -172.0(7) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C4 C5 C6 N7 -1.0(7) . . . . ?
C3 N7 C6 C5 1.0(5) . . . . ?
C8 N7 C6 C5 174.4(5) . . . . ?
C3 N7 C8 C1 -17.4(5) . . . . ?
C6 N7 C8 C1 169.5(5) . . . . ?
C9 C1 C8 N7 160.5(5) . . . . ?
C2 C1 C8 N7 28.2(5) . . . . ?
C10 O10 C9 O9 -5.5(8) . . . . ?
C10 O10 C9 C1 171.2(4) . . . . ?
C8 C1 C9 O9 -156.8(5) . . . . ?
C2 C1 C9 O9 -30.0(8) . . . . ?
C8 C1 C9 O10 26.5(7) . . . . ?
C2 C1 C9 O10 153.3(4) . . . . ?
C3 C2 C11 C12 -69.1(5) . . . . ?
C1 C2 C11 C12 177.7(4) . . . . ?
C2 C11 C12 O19 -14.3(6) . . . . ?
C2 C11 C12 C13 166.3(4) . . . . ?
O19 C12 C13 C18 -178.5(5) . . . . ?
C11 C12 C13 C18 0.9(7) . . . . ?
O19 C12 C13 C14 3.2(7) . . . . ?
C11 C12 C13 C14 -177.4(4) . . . . ?
C18 C13 C14 C15 -2.0(8) . . . . ?
C12 C13 C14 C15 176.4(5) . . . . ?
C13 C14 C15 C16 0.3(9) . . . . ?
C14 C15 C16 C17 2.4(9) . . . . ?
C14 C15 C16 Br16 -175.9(4) . . . . ?
C15 C16 C17 C18 -3.4(9) . . . . ?
Br16 C16 C17 C18 175.0(4) . . . . ?
C16 C17 C18 C13 1.6(8) . . . . ?
C14 C13 C18 C17 1.0(8) . . . . ?
C12 C13 C18 C17 -177.3(5) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


