# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_62
_database_code_depnum_ccdc_archive 'CCDC 2041146'
loop_
_audit_author_name
_audit_author_address
'Jambu Subramanian'
;Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Br N O'
_chemical_formula_weight         342.23

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                   14.4966(16)
_cell_length_b                   10.4123(11)
_cell_length_c                   11.2334(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.258(5)
_cell_angle_gamma                90
_cell_volume                     1580.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1390
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      19.84

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.599
_shelx_estimated_absorpt_T_min   0.563
_shelx_estimated_absorpt_T_max   0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            9144
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.507
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        24.990
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2783
_reflns_number_gt                1552
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2783
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.674
_refine_ls_restrained_S_all      1.674
_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 0.48841(5) 0.63607(6) 1.26431(5) 0.0793(3) Uani 1 1 d . . . . .
C1 C 0.2700(4) 0.9142(5) 1.1496(4) 0.0471(15) Uani 1 1 d . . . . .
H1 H 0.2212 0.9442 1.1781 0.057 Uiso 1 1 calc R U . . .
C2 C 0.3326(4) 0.8154(5) 1.2153(4) 0.0521(17) Uani 1 1 d . . . . .
H2 H 0.3255 0.7799 1.2875 0.062 Uiso 1 1 calc R U . . .
C3 C 0.4040(4) 0.7707(5) 1.1743(4) 0.0412(14) Uani 1 1 d . . . . .
C4 C 0.4153(4) 0.8223(5) 1.0685(4) 0.0443(15) Uani 1 1 d . . . . .
H4 H 0.4646 0.7918 1.0412 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3528(4) 0.9204(4) 1.0019(4) 0.0373(14) Uani 1 1 d . . . . .
H5 H 0.3605 0.9542 0.9293 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2802(4) 0.9687(4) 1.0406(4) 0.0285(13) Uani 1 1 d . . . . .
C7 C 0.2112(4) 1.0768(4) 0.9718(4) 0.0328(13) Uani 1 1 d . . . . .
H7 H 0.2293 1.1524 1.0275 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2189(3) 1.1145(4) 0.8459(4) 0.0307(13) Uani 1 1 d . . . . .
C9 C 0.3061(4) 1.1935(5) 0.8494(4) 0.0476(15) Uani 1 1 d . . . . .
H9A H 0.3545 1.2154 0.9325 0.057 Uiso 1 1 calc R U . . .
H9B H 0.3334 1.1784 0.7835 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2074(4) 1.2551(5) 0.8109(5) 0.0537(16) Uani 1 1 d . . . . .
H10A H 0.1745 1.2772 0.7215 0.064 Uiso 1 1 calc R U . . .
H10B H 0.1957 1.3142 0.8706 0.064 Uiso 1 1 calc R U . . .
C11 C 0.1714(4) 1.0202(5) 0.7435(4) 0.0324(13) Uani 1 1 d . . . . .
C12 C 0.2014(4) 0.9980(5) 0.6402(4) 0.0416(15) Uani 1 1 d . . . . .
H12 H 0.2556 1.0424 0.6354 0.050 Uiso 1 1 calc R U . . .
C13 C 0.1520(5) 0.9113(5) 0.5446(5) 0.0461(16) Uani 1 1 d . . . . .
C14 C 0.0730(4) 0.8438(5) 0.5538(4) 0.0508(16) Uani 1 1 d . . . . .
H14 H 0.0406 0.7835 0.4915 0.061 Uiso 1 1 calc R U . . .
C15 C 0.0415(4) 0.8645(5) 0.6543(4) 0.0455(14) Uani 1 1 d . . . . .
H15 H -0.0123 0.8189 0.6589 0.055 Uiso 1 1 calc R U . . .
C16 C 0.0898(4) 0.9535(5) 0.7489(4) 0.0317(13) Uani 1 1 d . . . . .
C17 C 0.0503(4) 0.9766(5) 0.8523(4) 0.0335(14) Uani 1 1 d . . . . .
C18 C 0.1847(4) 0.8882(5) 0.4326(4) 0.0655(18) Uani 1 1 d . . . . .
H18A H 0.1861 0.7976 0.4176 0.098 Uiso 1 1 calc R U . . .
H18B H 0.2497 0.9235 0.4514 0.098 Uiso 1 1 calc R U . . .
H18C H 0.1391 0.9290 0.3577 0.098 Uiso 1 1 calc R U . . .
N1 N 0.1083(3) 1.0470(4) 0.9509(4) 0.0352(12) Uani 1 1 d . . . . .
O1 O -0.0315(3) 0.9378(3) 0.8458(3) 0.0476(10) Uani 1 1 d . . . . .
H1N H 0.088(3) 1.054(4) 1.008(3) 0.013(14) Uiso 1 1 d . . . . .


_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 C3 1.894(5) . ?
C1 C2 1.394(6) . ?
C1 C6 1.405(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(6) . ?
C4 C5 1.390(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.518(6) . ?
C7 N1 1.457(6) . ?
C7 C8 1.511(6) . ?
C7 H7 0.9800 . ?
C8 C11 1.478(6) . ?
C8 C9 1.496(6) . ?
C8 C10 1.510(6) . ?
C9 C10 1.482(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.393(6) . ?
C11 C12 1.398(6) . ?
C12 C13 1.386(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(7) . ?
C13 C18 1.517(6) . ?
C14 C15 1.381(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.489(6) . ?
C17 O1 1.231(5) . ?
C17 N1 1.340(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 H1N 0.80(4) . ?

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
C2 C1 C6 120.4(5) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.4(5) . . ?
C2 C3 Br1 119.8(4) . . ?
C4 C3 Br1 119.8(4) . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.5(5) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 117.6(4) . . ?
C5 C6 C7 123.3(4) . . ?
C1 C6 C7 119.1(5) . . ?
N1 C7 C8 108.9(4) . . ?
N1 C7 C6 111.7(4) . . ?
C8 C7 C6 114.3(4) . . ?
N1 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
C6 C7 H7 107.2 . . ?
C11 C8 C9 122.5(4) . . ?
C11 C8 C10 117.7(4) . . ?
C9 C8 C10 59.1(3) . . ?
C11 C8 C7 112.6(4) . . ?
C9 C8 C7 117.8(4) . . ?
C10 C8 C7 117.2(4) . . ?
C10 C9 C8 60.9(3) . . ?
C10 C9 H9A 117.7 . . ?
C8 C9 H9A 117.7 . . ?
C10 C9 H9B 117.7 . . ?
C8 C9 H9B 117.7 . . ?
H9A C9 H9B 114.8 . . ?
C9 C10 C8 60.0(3) . . ?
C9 C10 H10A 117.8 . . ?
C8 C10 H10A 117.8 . . ?
C9 C10 H10B 117.8 . . ?
C8 C10 H10B 117.8 . . ?
H10A C10 H10B 114.9 . . ?
C16 C11 C12 118.6(5) . . ?
C16 C11 C8 117.5(4) . . ?
C12 C11 C8 123.9(5) . . ?
C13 C12 C11 121.4(5) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 C18 119.9(5) . . ?
C12 C13 C18 121.1(6) . . ?
C13 C14 C15 120.7(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.9(5) . . ?
C15 C16 C17 118.3(5) . . ?
C11 C16 C17 121.7(4) . . ?
O1 C17 N1 122.1(5) . . ?
O1 C17 C16 122.4(5) . . ?
N1 C17 C16 115.5(5) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 N1 C7 123.3(5) . . ?
C17 N1 H1N 114(3) . . ?
C7 N1 H1N 120(3) . . ?

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 -0.1(8) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
C1 C2 C3 Br1 -179.9(4) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
Br1 C3 C4 C5 179.5(4) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C4 C5 C6 C1 -0.8(7) . . . . ?
C4 C5 C6 C7 179.2(4) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
C2 C1 C6 C7 -179.6(4) . . . . ?
C5 C6 C7 N1 132.7(5) . . . . ?
C1 C6 C7 N1 -47.3(6) . . . . ?
C5 C6 C7 C8 8.5(7) . . . . ?
C1 C6 C7 C8 -171.5(4) . . . . ?
N1 C7 C8 C11 -50.8(5) . . . . ?
C6 C7 C8 C11 74.9(5) . . . . ?
N1 C7 C8 C9 158.0(4) . . . . ?
C6 C7 C8 C9 -76.3(5) . . . . ?
N1 C7 C8 C10 90.5(5) . . . . ?
C6 C7 C8 C10 -143.8(4) . . . . ?
C11 C8 C9 C10 105.2(5) . . . . ?
C7 C8 C9 C10 -106.6(5) . . . . ?
C11 C8 C10 C9 -113.1(5) . . . . ?
C7 C8 C10 C9 107.7(5) . . . . ?
C9 C8 C11 C16 -179.0(4) . . . . ?
C10 C8 C11 C16 -109.8(5) . . . . ?
C7 C8 C11 C16 31.3(6) . . . . ?
C9 C8 C11 C12 -1.4(7) . . . . ?
C10 C8 C11 C12 67.8(6) . . . . ?
C7 C8 C11 C12 -151.1(4) . . . . ?
C16 C11 C12 C13 -0.3(7) . . . . ?
C8 C11 C12 C13 -177.9(4) . . . . ?
C11 C12 C13 C14 -1.4(7) . . . . ?
C11 C12 C13 C18 179.7(4) . . . . ?
C12 C13 C14 C15 1.9(8) . . . . ?
C18 C13 C14 C15 -179.3(4) . . . . ?
C13 C14 C15 C16 -0.6(8) . . . . ?
C14 C15 C16 C11 -1.2(7) . . . . ?
C14 C15 C16 C17 177.4(4) . . . . ?
C12 C11 C16 C15 1.6(7) . . . . ?
C8 C11 C16 C15 179.3(4) . . . . ?
C12 C11 C16 C17 -176.9(4) . . . . ?
C8 C11 C16 C17 0.8(7) . . . . ?
C15 C16 C17 O1 -12.7(7) . . . . ?
C11 C16 C17 O1 165.8(5) . . . . ?
C15 C16 C17 N1 169.7(4) . . . . ?
C11 C16 C17 N1 -11.8(7) . . . . ?
O1 C17 N1 C7 169.8(5) . . . . ?
C16 C17 N1 C7 -12.6(7) . . . . ?
C8 C7 N1 C17 43.6(6) . . . . ?
C6 C7 N1 C17 -83.5(6) . . . . ?

_refine_diff_density_max         0.657
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.082



