# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1470802'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2017-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 Br2 N O2'
_chemical_formula_weight         425.12

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'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.19070(10)
_cell_length_b                   15.2739(3)
_cell_length_c                   17.2701(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1632.99(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    4170
_cell_measurement_theta_min      3.8370
_cell_measurement_theta_max      69.8540

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    6.349
_shelx_estimated_absorpt_T_min   0.260
_shelx_estimated_absorpt_T_max   0.300
_exptl_absorpt_correction_T_min  0.52136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            5808
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.864
_diffrn_reflns_theta_max         69.767
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2978
_reflns_number_gt                2920
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    0.975

_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       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_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)+(0.0829P)²+0.8396P] 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 1163 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.006(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2978
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
Br2 Br 1.15006(14) 0.55564(4) 0.45416(4) 0.0590(3) Uani 1 1 d . . . . .
Br1 Br 0.7854(2) 0.79793(6) 0.05138(5) 0.0831(4) Uani 1 1 d . . . . .
C12 C 0.9811(8) 0.8386(3) 0.3704(3) 0.0264(9) Uani 1 1 d . . . . .
O1 O 0.3338(6) 1.0193(3) 0.2903(3) 0.0553(12) Uani 1 1 d . . . . .
N1 N 0.9363(6) 0.9229(3) 0.3461(3) 0.0340(10) Uani 1 1 d . . . . .
H1 H 1.0418 0.9587 0.3397 0.041 Uiso 1 1 calc R U . . .
O2 O 0.4714(8) 1.1578(3) 0.2876(5) 0.0756(19) Uani 1 1 d . . . . .
C14 C 1.2298(9) 0.7370(4) 0.4302(3) 0.0365(11) Uani 1 1 d . . . . .
H14 H 1.3622 0.7253 0.4534 0.044 Uiso 1 1 calc R U . . .
C9 C 0.8288(9) 1.1107(3) 0.2903(4) 0.0406(12) Uani 1 1 d . . . . .
H9A H 0.9654 1.1271 0.3137 0.049 Uiso 1 1 calc R U . . .
H9B H 0.8560 1.0825 0.2409 0.049 Uiso 1 1 calc R U . . .
C2 C 0.7357(9) 0.8805(3) 0.1968(3) 0.0350(11) Uani 1 1 d . . . . .
H2 H 0.8700 0.8560 0.2075 0.042 Uiso 1 1 calc R U . . .
C15 C 1.0817(10) 0.6714(4) 0.4205(3) 0.0376(12) Uani 1 1 d . . . . .
C4 C 0.4330(9) 0.9681(3) 0.2345(4) 0.0416(13) Uani 1 1 d . . . . .
C1 C 0.6375(13) 0.8654(4) 0.1258(4) 0.0496(15) Uani 1 1 d . . . . .
C11 C 0.4648(10) 1.0814(4) 0.3302(5) 0.0488(16) Uani 1 1 d . . . . .
H11 H 0.3978 1.0941 0.3804 0.059 Uiso 1 1 calc R U . . .
C6 C 0.4326(13) 0.8987(5) 0.1100(5) 0.061(2) Uani 1 1 d . . . . .
H6 H 0.3641 0.8857 0.0635 0.073 Uiso 1 1 calc R U . . .
C3 C 0.6341(8) 0.9320(3) 0.2518(3) 0.0288(9) Uani 1 1 d . . . . .
C16 C 0.8817(9) 0.6868(3) 0.3881(3) 0.0343(11) Uani 1 1 d . . . . .
H16 H 0.7818 0.6416 0.3833 0.041 Uiso 1 1 calc R U . . .
C17 C 0.8317(8) 0.7707(3) 0.3627(3) 0.0329(10) Uani 1 1 d . . . . .
H17 H 0.6977 0.7817 0.3405 0.039 Uiso 1 1 calc R U . . .
C7 C 0.7210(7) 0.9528(3) 0.3313(3) 0.0284(9) Uani 1 1 d . . . . .
H7 H 0.6263 0.9237 0.3688 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6849(13) 1.1876(5) 0.2812(5) 0.0616(19) Uani 1 1 d . . . . .
H10A H 0.7150 1.2306 0.3211 0.074 Uiso 1 1 calc R U . . .
H10B H 0.7076 1.2148 0.2311 0.074 Uiso 1 1 calc R U . . .
C8 C 0.6971(8) 1.0515(4) 0.3441(3) 0.0342(10) Uani 1 1 d . . . . .
H8 H 0.7363 1.0650 0.3978 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3330(10) 0.9510(5) 0.1641(5) 0.060(2) Uani 1 1 d . . . . .
H5 H 0.1982 0.9751 0.1535 0.072 Uiso 1 1 calc R U . . .
C13 C 1.1812(8) 0.8209(4) 0.4052(3) 0.0348(11) Uani 1 1 d . . . . .
H13 H 1.2816 0.8657 0.4115 0.042 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
Br2 C15 1.908(5) . ?
Br1 C1 1.885(8) . ?
C12 N1 1.382(6) . ?
C12 C17 1.396(7) . ?
C12 C13 1.403(7) . ?
O1 C4 1.385(8) . ?
O1 C11 1.427(9) . ?
N1 C7 1.433(6) . ?
N1 H1 0.8600 . ?
O2 C11 1.380(8) . ?
O2 C10 1.403(10) . ?
C14 C15 1.368(9) . ?
C14 C13 1.386(8) . ?
C14 H14 0.9300 . ?
C9 C10 1.483(8) . ?
C9 C8 1.532(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 C3 1.384(7) . ?
C2 C1 1.388(8) . ?
C2 H2 0.9300 . ?
C15 C16 1.379(8) . ?
C4 C5 1.389(10) . ?
C4 C3 1.394(7) . ?
C1 C6 1.394(12) . ?
C11 C8 1.528(8) . ?
C11 H11 0.9800 . ?
C6 C5 1.375(13) . ?
C6 H6 0.9300 . ?
C3 C7 1.508(7) . ?
C16 C17 1.389(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C7 C8 1.531(7) . ?
C7 H7 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8 0.9800 . ?
C5 H5 0.9300 . ?
C13 H13 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
N1 C12 C17 122.0(4) . . ?
N1 C12 C13 119.1(5) . . ?
C17 C12 C13 118.9(5) . . ?
C4 O1 C11 117.4(4) . . ?
C12 N1 C7 122.6(4) . . ?
C12 N1 H1 118.7 . . ?
C7 N1 H1 118.7 . . ?
C11 O2 C10 110.2(5) . . ?
C15 C14 C13 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C10 C9 C8 102.2(5) . . ?
C10 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C3 C2 C1 120.1(6) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C14 C15 C16 121.7(5) . . ?
C14 C15 Br2 119.5(4) . . ?
C16 C15 Br2 118.7(5) . . ?
O1 C4 C5 121.2(5) . . ?
O1 C4 C3 118.0(5) . . ?
C5 C4 C3 120.8(6) . . ?
C2 C1 C6 120.7(7) . . ?
C2 C1 Br1 118.7(6) . . ?
C6 C1 Br1 120.5(6) . . ?
O2 C11 O1 108.7(7) . . ?
O2 C11 C8 108.0(5) . . ?
O1 C11 C8 114.3(5) . . ?
O2 C11 H11 108.6 . . ?
O1 C11 H11 108.6 . . ?
C8 C11 H11 108.6 . . ?
C5 C6 C1 119.2(7) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C2 C3 C4 118.9(5) . . ?
C2 C3 C7 125.6(4) . . ?
C4 C3 C7 115.5(5) . . ?
C15 C16 C17 119.0(5) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C12 120.5(5) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
N1 C7 C3 115.3(4) . . ?
N1 C7 C8 112.2(4) . . ?
C3 C7 C8 107.8(4) . . ?
N1 C7 H7 107.0 . . ?
C3 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
O2 C10 C9 107.5(5) . . ?
O2 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C11 C8 C7 111.2(5) . . ?
C11 C8 C9 103.3(5) . . ?
C7 C8 C9 116.2(4) . . ?
C11 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C6 C5 C4 120.2(6) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?

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
C17 C12 N1 C7 17.3(8) . . . . ?
C13 C12 N1 C7 -161.5(5) . . . . ?
C13 C14 C15 C16 -1.7(8) . . . . ?
C13 C14 C15 Br2 179.5(4) . . . . ?
C11 O1 C4 C5 -137.9(6) . . . . ?
C11 O1 C4 C3 43.9(7) . . . . ?
C3 C2 C1 C6 -2.6(8) . . . . ?
C3 C2 C1 Br1 178.0(4) . . . . ?
C10 O2 C11 O1 -132.8(7) . . . . ?
C10 O2 C11 C8 -8.2(9) . . . . ?
C4 O1 C11 O2 86.2(6) . . . . ?
C4 O1 C11 C8 -34.5(8) . . . . ?
C2 C1 C6 C5 3.6(9) . . . . ?
Br1 C1 C6 C5 -177.0(5) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C1 C2 C3 C7 179.3(5) . . . . ?
O1 C4 C3 C2 179.9(5) . . . . ?
C5 C4 C3 C2 1.7(8) . . . . ?
O1 C4 C3 C7 0.4(7) . . . . ?
C5 C4 C3 C7 -177.8(5) . . . . ?
C14 C15 C16 C17 1.8(8) . . . . ?
Br2 C15 C16 C17 -179.4(4) . . . . ?
C15 C16 C17 C12 -0.4(8) . . . . ?
N1 C12 C17 C16 -179.7(5) . . . . ?
C13 C12 C17 C16 -0.9(8) . . . . ?
C12 N1 C7 C3 -84.0(6) . . . . ?
C12 N1 C7 C8 152.0(5) . . . . ?
C2 C3 C7 N1 6.5(7) . . . . ?
C4 C3 C7 N1 -174.2(4) . . . . ?
C2 C3 C7 C8 132.7(5) . . . . ?
C4 C3 C7 C8 -47.9(5) . . . . ?
C11 O2 C10 C9 25.0(10) . . . . ?
C8 C9 C10 O2 -30.3(8) . . . . ?
O2 C11 C8 C7 -136.2(6) . . . . ?
O1 C11 C8 C7 -15.1(7) . . . . ?
O2 C11 C8 C9 -10.9(7) . . . . ?
O1 C11 C8 C9 110.3(6) . . . . ?
N1 C7 C8 C11 -178.3(5) . . . . ?
C3 C7 C8 C11 53.7(5) . . . . ?
N1 C7 C8 C9 63.9(6) . . . . ?
C3 C7 C8 C9 -64.1(6) . . . . ?
C10 C9 C8 C11 24.2(7) . . . . ?
C10 C9 C8 C7 146.3(6) . . . . ?
C1 C6 C5 C4 -2.0(10) . . . . ?
O1 C4 C5 C6 -178.8(6) . . . . ?
C3 C4 C5 C6 -0.6(9) . . . . ?
C15 C14 C13 C12 0.3(8) . . . . ?
N1 C12 C13 C14 179.9(5) . . . . ?
C17 C12 C13 C14 1.0(7) . . . . ?

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
N1 H1 O1 0.86 2.20 3.026(6) 160.2 1_655

_refine_diff_density_max         0.850
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.096

_shelxl_version_number           2013-4

