# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_MB-2N-5A_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1915125'
loop_
_audit_author_name
_audit_author_address
'MEGHA BALHA'
;IIT Guwahati
India
;
_audit_update_record             
;
2019-05-09 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H18 Br N3 O2'
_chemical_formula_sum            'C25 H18 Br N3 O2'
_chemical_formula_weight         472.3420

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'
Br Br -0.2901 2.4595 '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'

_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                   9.925(4)
_cell_length_b                   13.094(5)
_cell_length_c                   16.855(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.017(12)
_cell_angle_gamma                90
_cell_volume                     2115.8(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2729
_cell_measurement_theta_min      1.996
_cell_measurement_theta_max      25.000

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.970
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69918
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.996
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3733
_reflns_number_gt                2729
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²+0.4640P] 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_number_reflns         3733
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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_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
Br01 Br 0.49968(4) 0.66426(3) 0.87568(3) 0.0626(2) Uani 1 1 d . . . . .
O002 O 0.4645(2) 0.42540(19) 0.62969(13) 0.0419(6) Uani 1 1 d . . . . .
O003 O 0.5793(3) 0.6290(2) 0.62608(16) 0.0532(6) Uani 1 1 d . . . . .
N004 N 0.7324(3) 0.5551(2) 0.73744(17) 0.0442(7) Uani 1 1 d . . . . .
N005 N 0.2884(3) 0.4067(2) 0.51497(18) 0.0520(8) Uani 1 1 d . . . . .
H00A H 0.205012 0.417571 0.485412 0.062 Uiso 1 1 calc R U . . .
H00B H 0.343733 0.367853 0.496924 0.062 Uiso 1 1 calc R U . . .
N006 N 0.0190(3) 0.5784(3) 0.58028(18) 0.0554(8) Uani 1 1 d . . . . .
C007 C 0.3659(3) 0.5407(3) 0.71271(19) 0.0362(7) Uani 1 1 d . . . . .
H007 H 0.378661 0.614986 0.714846 0.043 Uiso 1 1 calc R U . . .
C008 C 0.5039(3) 0.4896(3) 0.70306(19) 0.0353(7) Uani 1 1 d . . . . .
C009 C 0.3316(3) 0.4499(3) 0.5884(2) 0.0397(8) Uani 1 1 d . . . . .
C00A C 0.3210(3) 0.5073(3) 0.78793(19) 0.0362(7) Uani 1 1 d . . . . .
C00B C 0.5939(3) 0.4310(3) 0.7730(2) 0.0383(8) Uani 1 1 d . . . . .
C00C C 0.7263(3) 0.4732(3) 0.7916(2) 0.0407(8) Uani 1 1 d . . . . .
C00D C 0.1306(3) 0.5489(3) 0.60223(19) 0.0403(8) Uani 1 1 d . . . . .
C00E C 0.6061(3) 0.5687(3) 0.6826(2) 0.0406(8) Uani 1 1 d . . . . .
C00F C 0.2680(3) 0.5129(3) 0.6310(2) 0.0386(8) Uani 1 1 d . . . . .
C00G C 0.2268(3) 0.4273(3) 0.7845(2) 0.0452(8) Uani 1 1 d . . . . .
H00G H 0.188238 0.395517 0.734369 0.054 Uiso 1 1 calc R U . . .
C00H C 0.9373(3) 0.6719(3) 0.7897(2) 0.0418(8) Uani 1 1 d . . . . .
C00I C 0.3717(3) 0.5538(3) 0.8639(2) 0.0417(8) Uani 1 1 d . . . . .
C00J C 0.5680(4) 0.3484(3) 0.8173(2) 0.0456(9) Uani 1 1 d . . . . .
H00J H 0.479772 0.318857 0.805071 0.055 Uiso 1 1 calc R U . . .
C00K C 1.0608(4) 0.7130(3) 0.7804(2) 0.0504(9) Uani 1 1 d . . . . .
H00K H 1.094057 0.694246 0.735669 0.060 Uiso 1 1 calc R U . . .
C00L C 0.8334(4) 0.4372(3) 0.8544(2) 0.0553(10) Uani 1 1 d . . . . .
H00L H 0.921220 0.467288 0.866856 0.066 Uiso 1 1 calc R U . . .
C00M C 0.1894(4) 0.3941(3) 0.8536(2) 0.0546(10) Uani 1 1 d . . . . .
H00M H 0.129797 0.338552 0.850317 0.066 Uiso 1 1 calc R U . . .
C00N C 0.8897(4) 0.7013(3) 0.8564(2) 0.0519(10) Uani 1 1 d . . . . .
H00N H 0.806515 0.674867 0.863268 0.062 Uiso 1 1 calc R U . . .
C00O C 0.3318(4) 0.5231(4) 0.9328(2) 0.0570(11) Uani 1 1 d . . . . .
H00O H 0.366800 0.556194 0.982715 0.068 Uiso 1 1 calc R U . . .
C00P C 0.8611(4) 0.5977(3) 0.7254(2) 0.0551(10) Uani 1 1 d . . . . .
H00D H 0.839463 0.632033 0.672552 0.066 Uiso 1 1 calc R U . . .
H00E H 0.923719 0.541761 0.722639 0.066 Uiso 1 1 calc R U . . .
C00Q C 0.6746(4) 0.3095(3) 0.8801(3) 0.0570(10) Uani 1 1 d . . . . .
H00Q H 0.658266 0.253262 0.910047 0.068 Uiso 1 1 calc R U . . .
C00R C 0.9653(4) 0.7698(3) 0.9128(3) 0.0599(11) Uani 1 1 d . . . . .
H00R H 0.932669 0.788900 0.957643 0.072 Uiso 1 1 calc R U . . .
C00S C 1.0877(5) 0.8102(3) 0.9038(3) 0.0631(12) Uani 1 1 d . . . . .
H00S H 1.138330 0.856286 0.942086 0.076 Uiso 1 1 calc R U . . .
C00T C 0.8049(5) 0.3543(3) 0.8984(3) 0.0633(12) Uani 1 1 d . . . . .
H00T H 0.875262 0.328100 0.941228 0.076 Uiso 1 1 calc R U . . .
C00U C 1.1344(4) 0.7814(3) 0.8372(3) 0.0626(11) Uani 1 1 d . . . . .
H00U H 1.217198 0.808695 0.830389 0.075 Uiso 1 1 calc R U . . .
C00V C 0.2402(4) 0.4433(4) 0.9272(2) 0.0629(12) Uani 1 1 d . . . . .
H00V H 0.212571 0.422487 0.973344 0.076 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
Br01 C00I 1.901(4) . ?
O002 C009 1.361(4) . ?
O002 C008 1.462(4) . ?
O003 C00E 1.213(4) . ?
N004 C00E 1.363(4) . ?
N004 C00C 1.418(5) . ?
N004 C00P 1.455(4) . ?
N005 C009 1.327(4) . ?
N005 H00A 0.8600 . ?
N005 H00B 0.8600 . ?
N006 C00D 1.140(4) . ?
C007 C00F 1.510(4) . ?
C007 C00A 1.513(4) . ?
C007 C008 1.570(4) . ?
C007 H007 0.9800 . ?
C008 C00B 1.495(5) . ?
C008 C00E 1.549(5) . ?
C009 C00F 1.353(5) . ?
C00A C00I 1.389(5) . ?
C00A C00G 1.395(5) . ?
C00B C00J 1.375(5) . ?
C00B C00C 1.385(5) . ?
C00C C00L 1.375(5) . ?
C00D C00F 1.405(5) . ?
C00G C00M 1.382(5) . ?
C00G H00G 0.9300 . ?
C00H C00N 1.383(5) . ?
C00H C00K 1.385(5) . ?
C00H C00P 1.505(5) . ?
C00I C00O 1.381(5) . ?
C00J C00Q 1.386(5) . ?
C00J H00J 0.9300 . ?
C00K C00U 1.375(6) . ?
C00K H00K 0.9300 . ?
C00L C00T 1.385(6) . ?
C00L H00L 0.9300 . ?
C00M C00V 1.372(6) . ?
C00M H00M 0.9300 . ?
C00N C00R 1.379(6) . ?
C00N H00N 0.9300 . ?
C00O C00V 1.372(6) . ?
C00O H00O 0.9300 . ?
C00P H00D 0.9700 . ?
C00P H00E 0.9700 . ?
C00Q C00T 1.381(6) . ?
C00Q H00Q 0.9300 . ?
C00R C00S 1.369(6) . ?
C00R H00R 0.9300 . ?
C00S C00U 1.374(6) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00V H00V 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
C009 O002 C008 108.0(2) . . ?
C00E N004 C00C 110.5(3) . . ?
C00E N004 C00P 122.8(3) . . ?
C00C N004 C00P 124.4(3) . . ?
C009 N005 H00A 120.0 . . ?
C009 N005 H00B 120.0 . . ?
H00A N005 H00B 120.0 . . ?
C00F C007 C00A 115.7(3) . . ?
C00F C007 C008 100.1(2) . . ?
C00A C007 C008 114.7(3) . . ?
C00F C007 H007 108.6 . . ?
C00A C007 H007 108.6 . . ?
C008 C007 H007 108.6 . . ?
O002 C008 C00B 110.2(3) . . ?
O002 C008 C00E 104.1(2) . . ?
C00B C008 C00E 103.1(3) . . ?
O002 C008 C007 106.5(2) . . ?
C00B C008 C007 119.8(3) . . ?
C00E C008 C007 112.1(3) . . ?
N005 C009 C00F 132.3(3) . . ?
N005 C009 O002 114.4(3) . . ?
C00F C009 O002 113.3(3) . . ?
C00I C00A C00G 116.5(3) . . ?
C00I C00A C007 122.0(3) . . ?
C00G C00A C007 121.4(3) . . ?
C00J C00B C00C 119.5(3) . . ?
C00J C00B C008 132.4(3) . . ?
C00C C00B C008 108.1(3) . . ?
C00L C00C C00B 122.3(3) . . ?
C00L C00C N004 127.0(3) . . ?
C00B C00C N004 110.7(3) . . ?
N006 C00D C00F 178.8(3) . . ?
O003 C00E N004 126.4(3) . . ?
O003 C00E C008 125.9(3) . . ?
N004 C00E C008 107.6(3) . . ?
C009 C00F C00D 124.5(3) . . ?
C009 C00F C007 110.6(3) . . ?
C00D C00F C007 124.9(3) . . ?
C00M C00G C00A 121.6(3) . . ?
C00M C00G H00G 119.2 . . ?
C00A C00G H00G 119.2 . . ?
C00N C00H C00K 118.9(3) . . ?
C00N C00H C00P 123.5(3) . . ?
C00K C00H C00P 117.6(3) . . ?
C00O C00I C00A 122.2(3) . . ?
C00O C00I Br01 117.6(3) . . ?
C00A C00I Br01 120.2(3) . . ?
C00B C00J C00Q 119.4(4) . . ?
C00B C00J H00J 120.3 . . ?
C00Q C00J H00J 120.3 . . ?
C00U C00K C00H 120.0(4) . . ?
C00U C00K H00K 120.0 . . ?
C00H C00K H00K 120.0 . . ?
C00C C00L C00T 117.2(4) . . ?
C00C C00L H00L 121.4 . . ?
C00T C00L H00L 121.4 . . ?
C00V C00M C00G 119.9(4) . . ?
C00V C00M H00M 120.0 . . ?
C00G C00M H00M 120.0 . . ?
C00R C00N C00H 120.2(4) . . ?
C00R C00N H00N 119.9 . . ?
C00H C00N H00N 119.9 . . ?
C00V C00O C00I 119.6(4) . . ?
C00V C00O H00O 120.2 . . ?
C00I C00O H00O 120.2 . . ?
N004 C00P C00H 116.3(3) . . ?
N004 C00P H00D 108.2 . . ?
C00H C00P H00D 108.2 . . ?
N004 C00P H00E 108.2 . . ?
C00H C00P H00E 108.2 . . ?
H00D C00P H00E 107.4 . . ?
C00T C00Q C00J 120.0(4) . . ?
C00T C00Q H00Q 120.0 . . ?
C00J C00Q H00Q 120.0 . . ?
C00S C00R C00N 121.0(4) . . ?
C00S C00R H00R 119.5 . . ?
C00N C00R H00R 119.5 . . ?
C00R C00S C00U 118.8(4) . . ?
C00R C00S H00S 120.6 . . ?
C00U C00S H00S 120.6 . . ?
C00Q C00T C00L 121.5(4) . . ?
C00Q C00T H00T 119.2 . . ?
C00L C00T H00T 119.2 . . ?
C00S C00U C00K 121.2(4) . . ?
C00S C00U H00U 119.4 . . ?
C00K C00U H00U 119.4 . . ?
C00O C00V C00M 120.1(4) . . ?
C00O C00V H00V 119.9 . . ?
C00M C00V H00V 119.9 . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.059

