# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_iw0604c
_database_code_depnum_ccdc_archive 'CCDC 1874398'
_audit_update_record             
;
2018-10-23 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 Br N O'
_chemical_melting_point          ?
_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_diffrn_ambient_temperature      120
_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'

_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'
_chemical_absolute_configuration ad

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'

_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.
;

_cell_length_a                   6.0888(8)
_cell_length_b                   12.5645(17)
_cell_length_c                   17.867(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1366.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120
_cell_measurement_reflns_used    10301
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      30.0
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.001
_shelx_estimated_absorpt_T_min   0.380
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.267
_exptl_absorpt_correction_T_max  0.677
_exptl_absorpt_process_details   'NUMABS (Rigaku Corp.)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode X-ray tube'
_diffrn_measurement_device_type  
;
AFC7R, 4-circle diffractometer with Mercury CCD camera (Rigaku Corp.)
;

_diffrn_measurement_method       
;
Oscillation method with Fine-Slice process
;
_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            29902
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.982
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3974
_reflns_number_gt                3693
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.991

_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       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution    'SIR2004 (Burla, Caliandro et al., 2005)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0204P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(2)

_refine_ls_number_reflns         3974
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0488
_refine_ls_wR_factor_gt          0.0481
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.002
_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
C1 C 1.1380(4) 1.32243(17) 1.12781(13) 0.0192(4) Uani 1 1 d . . . . .
H1 H 1.242(4) 1.381(2) 1.1420(15) 0.035(8) Uiso 1 1 d . . . . .
C2 C 0.9556(4) 1.34677(16) 1.08386(12) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.924(4) 1.423(2) 1.0639(14) 0.029(7) Uiso 1 1 d . . . . .
C3 C 0.8103(4) 1.26885(19) 1.06030(12) 0.0210(5) Uani 1 1 d . . . . .
H3 H 0.684(4) 1.2897(19) 1.0335(13) 0.023(7) Uiso 1 1 d . . . . .
C4 C 0.8419(4) 1.16204(17) 1.08087(12) 0.0176(4) Uani 1 1 d . . . . .
H4 H 0.740(4) 1.1121(19) 1.0645(13) 0.019(7) Uiso 1 1 d . . . . .
C5 C 1.0225(3) 1.13632(14) 1.12392(10) 0.0144(4) Uani 1 1 d . . . . .
C6 C 1.1684(3) 1.21687(17) 1.14662(11) 0.0157(4) Uani 1 1 d . . . . .
C7 C 1.3211(3) 1.06380(17) 1.19292(12) 0.0159(4) Uani 1 1 d . . . . .
C8 C 1.1101(3) 1.03532(15) 1.15473(12) 0.0147(4) Uani 1 1 d . . . . .
C9 C 0.9773(4) 0.94923(15) 1.19449(11) 0.0169(4) Uani 1 1 d . . . . .
H5 H 0.819(4) 0.9656(18) 1.1970(13) 0.017(6) Uiso 1 1 d . . . . .
H6 H 1.033(4) 0.9234(17) 1.2384(12) 0.017(6) Uiso 1 1 d . . . . .
C10 C 1.0786(3) 0.92383(17) 1.12109(12) 0.0161(4) Uani 1 1 d . . . . .
H7 H 1.215(4) 0.881(2) 1.1227(14) 0.026(7) Uiso 1 1 d . . . . .
C11 C 0.9407(3) 0.90912(15) 1.05330(11) 0.0153(4) Uani 1 1 d . . . . .
C12 C 1.0161(4) 0.93514(14) 0.98208(11) 0.0172(4) Uani 1 1 d . . . . .
H8 H 1.160(4) 0.9639(18) 0.9757(13) 0.015(6) Uiso 1 1 d . . . . .
C13 C 0.8898(4) 0.91991(17) 0.91872(12) 0.0177(4) Uani 1 1 d . . . . .
H9 H 0.946(4) 0.9414(18) 0.8699(13) 0.020(6) Uiso 1 1 d . . . . .
C14 C 0.6800(4) 0.87756(16) 0.92690(12) 0.0160(4) Uani 1 1 d . . . . .
C15 C 0.5991(4) 0.84987(16) 0.99676(12) 0.0161(4) Uani 1 1 d . . . . .
H10 H 0.461(4) 0.8215(16) 1.0024(12) 0.010(6) Uiso 1 1 d . . . . .
C16 C 0.7287(3) 0.86658(17) 1.05941(12) 0.0162(4) Uani 1 1 d . . . . .
H11 H 0.674(4) 0.8440(19) 1.1052(14) 0.021(6) Uiso 1 1 d . . . . .
Br1 Br 0.49751(4) 0.85993(2) 0.84163(2) 0.01932(6) Uani 1 1 d . . . . .
O1 O 1.4480(2) 1.00373(12) 1.22563(9) 0.0211(3) Uani 1 1 d . . . . .
N1 N 1.3413(3) 1.17221(14) 1.18842(10) 0.0161(4) Uani 1 1 d . . . . .
C17 C 1.5088(4) 1.23448(15) 1.22708(11) 0.0211(4) Uani 1 1 d . . . . .
H12 H 1.441994 1.274167 1.266945 0.032 Uiso 1 1 calc R U . . .
H13 H 1.576633 1.282711 1.192397 0.032 Uiso 1 1 calc R U . . .
H14 H 1.618104 1.187527 1.247338 0.032 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
C1 C6 1.381(3) . ?
C1 C2 1.394(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.405(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.407(3) . ?
C5 C8 1.483(3) . ?
C6 N1 1.408(3) . ?
C7 O1 1.228(3) . ?
C7 N1 1.370(3) . ?
C7 C8 1.498(3) . ?
C8 C9 1.526(3) . ?
C8 C10 1.536(3) . ?
C9 C10 1.484(3) . ?
C10 C11 1.485(3) . ?
C11 C12 1.392(3) . ?
C11 C16 1.402(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.386(3) . ?
C14 Br1 1.899(2) . ?
C15 C16 1.385(3) . ?
N1 C17 1.459(3) . ?

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
C6 C1 C2 117.1(2) . . ?
C3 C2 C1 121.7(2) . . ?
C2 C3 C4 120.5(2) . . ?
C5 C4 C3 118.6(2) . . ?
C4 C5 C6 119.69(18) . . ?
C4 C5 C8 133.95(19) . . ?
C6 C5 C8 106.35(18) . . ?
C1 C6 C5 122.4(2) . . ?
C1 C6 N1 127.8(2) . . ?
C5 C6 N1 109.80(18) . . ?
O1 C7 N1 125.6(2) . . ?
O1 C7 C8 127.6(2) . . ?
N1 C7 C8 106.74(17) . . ?
C5 C8 C7 105.85(16) . . ?
C5 C8 C9 126.08(18) . . ?
C7 C8 C9 114.32(18) . . ?
C5 C8 C10 126.17(18) . . ?
C7 C8 C10 120.21(17) . . ?
C9 C8 C10 57.97(13) . . ?
C10 C9 C8 61.37(14) . . ?
C9 C10 C11 120.84(19) . . ?
C9 C10 C8 60.66(13) . . ?
C11 C10 C8 120.21(18) . . ?
C12 C11 C16 117.7(2) . . ?
C12 C11 C10 122.00(19) . . ?
C16 C11 C10 120.30(19) . . ?
C13 C12 C11 122.2(2) . . ?
C12 C13 C14 118.5(2) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 Br1 119.04(16) . . ?
C13 C14 Br1 119.83(16) . . ?
C16 C15 C14 119.1(2) . . ?
C15 C16 C11 121.3(2) . . ?
C7 N1 C6 111.11(17) . . ?
C7 N1 C17 124.62(18) . . ?
C6 N1 C17 124.07(17) . . ?

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 0.3(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C8 -178.9(2) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C1 C6 N1 178.2(2) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C8 C5 C6 C1 180.0(2) . . . . ?
C4 C5 C6 N1 -178.83(18) . . . . ?
C8 C5 C6 N1 0.8(2) . . . . ?
C4 C5 C8 C7 176.7(2) . . . . ?
C6 C5 C8 C7 -2.8(2) . . . . ?
C4 C5 C8 C9 -45.8(3) . . . . ?
C6 C5 C8 C9 134.6(2) . . . . ?
C4 C5 C8 C10 27.9(4) . . . . ?
C6 C5 C8 C10 -151.64(19) . . . . ?
O1 C7 C8 C5 -179.6(2) . . . . ?
N1 C7 C8 C5 3.9(2) . . . . ?
O1 C7 C8 C9 37.3(3) . . . . ?
N1 C7 C8 C9 -139.26(18) . . . . ?
O1 C7 C8 C10 -28.5(3) . . . . ?
N1 C7 C8 C10 154.97(18) . . . . ?
C5 C8 C9 C10 113.9(2) . . . . ?
C7 C8 C9 C10 -111.63(19) . . . . ?
C8 C9 C10 C11 -109.7(2) . . . . ?
C5 C8 C10 C9 -113.8(2) . . . . ?
C7 C8 C10 C9 101.4(2) . . . . ?
C5 C8 C10 C11 -3.1(3) . . . . ?
C7 C8 C10 C11 -147.9(2) . . . . ?
C9 C8 C10 C11 110.7(2) . . . . ?
C9 C10 C11 C12 148.82(19) . . . . ?
C8 C10 C11 C12 77.0(3) . . . . ?
C9 C10 C11 C16 -32.1(3) . . . . ?
C8 C10 C11 C16 -103.8(2) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C10 C11 C12 C13 178.88(19) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C12 C13 C14 Br1 177.85(16) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
Br1 C14 C15 C16 -177.47(16) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C12 C11 C16 C15 0.7(3) . . . . ?
C10 C11 C16 C15 -178.5(2) . . . . ?
O1 C7 N1 C6 179.8(2) . . . . ?
C8 C7 N1 C6 -3.5(2) . . . . ?
O1 C7 N1 C17 -5.1(3) . . . . ?
C8 C7 N1 C17 171.52(18) . . . . ?
C1 C6 N1 C7 -177.4(2) . . . . ?
C5 C6 N1 C7 1.8(2) . . . . ?
C1 C6 N1 C17 7.5(3) . . . . ?
C5 C6 N1 C17 -173.30(18) . . . . ?

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
_geom_hbond_publ_flag
C17 H14 Br1 0.96 2.94 3.825(2) 153.0 2_775 yes

_refine_diff_density_max         0.964
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.055

_diffrn_radiation_monochromator  'Graphite Monochromator'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
