# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1506167'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2018-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 Br N O'
_chemical_formula_weight         328.20

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.1624(6)
_cell_length_b                   7.7041(7)
_cell_length_c                   30.136(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1430.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7771
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    2.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3586
_exptl_absorpt_correction_T_max  0.6569
_exptl_absorpt_process_details   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 Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16442
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2517
_reflns_number_gt                2337
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0284P)²+0.2261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2517
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0569
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.35056(4) 0.48617(4) 0.913075(7) 0.06378(10) Uani 1 1 d . . .
O1 O -0.0742(2) 0.4697(2) 1.12167(4) 0.0467(4) Uani 1 1 d . . .
C8 C -0.4298(4) 0.5635(3) 1.13500(7) 0.0470(5) Uani 1 1 d . . .
H8A H -0.5532 0.4886 1.1407 0.056 Uiso 1 1 calc R . .
H8B H -0.4637 0.6795 1.1454 0.056 Uiso 1 1 calc R . .
C1 C 0.1802(3) 0.4880(3) 0.96573(7) 0.0447(5) Uani 1 1 d . . .
C2 C -0.0243(4) 0.5597(3) 0.96494(7) 0.0482(6) Uani 1 1 d . . .
H2A H -0.0817 0.6027 0.9386 0.058 Uiso 1 1 calc R . .
C3 C -0.1426(4) 0.5671(3) 1.00340(7) 0.0446(5) Uani 1 1 d . . .
H3A H -0.2810 0.6152 1.0031 0.054 Uiso 1 1 calc R . .
C4 C -0.0563(3) 0.5027(3) 1.04311(6) 0.0395(4) Uani 1 1 d . . .
C5 C 0.1490(4) 0.4304(3) 1.04259(7) 0.0450(5) Uani 1 1 d . . .
H5A H 0.2074 0.3868 1.0688 0.054 Uiso 1 1 calc R . .
C6 C 0.2685(4) 0.4216(3) 1.00412(7) 0.0465(5) Uani 1 1 d . . .
H6A H 0.4061 0.3719 1.0040 0.056 Uiso 1 1 calc R . .
C7 C -0.1839(3) 0.5152(3) 1.08400(6) 0.0389(4) Uani 1 1 d . . .
N1 N -0.3777(3) 0.5656(3) 1.08781(6) 0.0469(4) Uani 1 1 d . . .
C9 C -0.2245(3) 0.4931(3) 1.15824(6) 0.0400(4) Uani 1 1 d . . .
H9A H -0.2568 0.3802 1.1717 0.048 Uiso 1 1 calc R . .
C10 C -0.1267(3) 0.6115(3) 1.19277(6) 0.0366(4) Uani 1 1 d . . .
C11 C -0.2260(3) 0.6058(3) 1.23755(7) 0.0346(4) Uani 1 1 d . . .
C12 C -0.1191(4) 0.6789(3) 1.27395(7) 0.0450(5) Uani 1 1 d . . .
H12A H 0.0152 0.7314 1.2698 0.054 Uiso 1 1 calc R . .
C13 C -0.2089(4) 0.6747(3) 1.31601(8) 0.0525(6) Uani 1 1 d . . .
H13A H -0.1345 0.7241 1.3397 0.063 Uiso 1 1 calc R . .
C14 C -0.4067(4) 0.5984(3) 1.32301(8) 0.0518(6) Uani 1 1 d . . .
H14A H -0.4672 0.5962 1.3513 0.062 Uiso 1 1 calc R . .
C15 C -0.5153(4) 0.5248(3) 1.28768(8) 0.0512(5) Uani 1 1 d . . .
H15A H -0.6493 0.4722 1.2922 0.061 Uiso 1 1 calc R . .
C16 C -0.4259(3) 0.5288(3) 1.24558(7) 0.0435(5) Uani 1 1 d . . .
H16A H -0.5014 0.4787 1.2221 0.052 Uiso 1 1 calc R . .
C17 C 0.0348(4) 0.7159(3) 1.18217(8) 0.0518(6) Uani 1 1 d . . .
H17C H 0.0920 0.7910 1.2033 0.062 Uiso 1 1 calc R . .
H17A H 0.0914 0.7144 1.1536 0.062 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 C1 1.903(2) . ?
O1 C7 1.367(2) . ?
O1 C9 1.451(2) . ?
C8 N1 1.458(3) . ?
C8 C9 1.545(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.376(3) . ?
C1 C6 1.377(3) . ?
C2 C3 1.370(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.400(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(3) . ?
C4 C7 1.465(3) . ?
C5 C6 1.375(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 N1 1.261(3) . ?
C9 C10 1.509(3) . ?
C9 H9A 0.9800 . ?
C10 C17 1.319(3) . ?
C10 C11 1.482(3) . ?
C11 C16 1.389(3) . ?
C11 C12 1.398(3) . ?
C12 C13 1.383(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.370(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.383(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17C 0.9300 . ?
C17 H17A 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
C7 O1 C9 106.45(15) . . ?
N1 C8 C9 105.42(17) . . ?
N1 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
N1 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C2 C1 C6 121.72(19) . . ?
C2 C1 Br1 119.59(16) . . ?
C6 C1 Br1 118.67(16) . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 118.72(19) . . ?
C5 C4 C7 121.82(18) . . ?
C3 C4 C7 119.5(2) . . ?
C6 C5 C4 121.29(19) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 H6A 120.7 . . ?
C1 C6 H6A 120.7 . . ?
N1 C7 O1 118.14(18) . . ?
N1 C7 C4 127.25(18) . . ?
O1 C7 C4 114.59(17) . . ?
C7 N1 C8 107.10(17) . . ?
O1 C9 C10 110.12(17) . . ?
O1 C9 C8 102.83(15) . . ?
C10 C9 C8 115.33(19) . . ?
O1 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C17 C10 C11 123.35(19) . . ?
C17 C10 C9 120.19(19) . . ?
C11 C10 C9 116.43(18) . . ?
C16 C11 C12 116.95(19) . . ?
C16 C11 C10 122.51(18) . . ?
C12 C11 C10 120.55(19) . . ?
C13 C12 C11 121.4(2) . . ?
C13 C12 H12A 119.3 . . ?
C11 C12 H12A 119.3 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14A 120.4 . . ?
C15 C14 H14A 120.4 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 121.5(2) . . ?
C15 C16 H16A 119.2 . . ?
C11 C16 H16A 119.2 . . ?
C10 C17 H17C 120.0 . . ?
C10 C17 H17A 120.0 . . ?
H17C C17 H17A 120.0 . . ?

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
C6 C1 C2 C3 0.7(3) . . . . ?
Br1 C1 C2 C3 -177.29(16) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C2 C3 C4 C7 178.8(2) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C7 C4 C5 C6 -179.1(2) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
Br1 C1 C6 C5 177.01(17) . . . . ?
C9 O1 C7 N1 0.4(3) . . . . ?
C9 O1 C7 C4 179.04(18) . . . . ?
C5 C4 C7 N1 -173.9(2) . . . . ?
C3 C4 C7 N1 6.7(3) . . . . ?
C5 C4 C7 O1 7.5(3) . . . . ?
C3 C4 C7 O1 -171.83(19) . . . . ?
O1 C7 N1 C8 1.2(3) . . . . ?
C4 C7 N1 C8 -177.3(2) . . . . ?
C9 C8 N1 C7 -2.2(2) . . . . ?
C7 O1 C9 C10 -125.07(17) . . . . ?
C7 O1 C9 C8 -1.7(2) . . . . ?
N1 C8 C9 O1 2.3(2) . . . . ?
N1 C8 C9 C10 122.19(19) . . . . ?
O1 C9 C10 C17 20.0(3) . . . . ?
C8 C9 C10 C17 -95.8(2) . . . . ?
O1 C9 C10 C11 -161.70(17) . . . . ?
C8 C9 C10 C11 82.5(2) . . . . ?
C17 C10 C11 C16 163.9(2) . . . . ?
C9 C10 C11 C16 -14.4(3) . . . . ?
C17 C10 C11 C12 -16.3(3) . . . . ?
C9 C10 C11 C12 165.41(19) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?
C10 C11 C12 C13 -179.9(2) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C11 0.1(4) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
C10 C11 C16 C15 179.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.040
