# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_DMS_BES_250422_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2184029'
loop_
_audit_author_name
_audit_author_address
'Sherin Anto'
;Vellore Institute of Technology
India
;
_audit_update_record             
;
2022-07-05 deposited with the CCDC.	2023-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 Br N2'
_chemical_formula_sum            'C16 H19 Br N2'
_chemical_formula_weight         319.24

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'

_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                   6.3288(5)
_cell_length_b                   7.7010(6)
_cell_length_c                   32.103(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.396(2)
_cell_angle_gamma                90
_cell_volume                     1564.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      26.82

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.617
_shelx_estimated_absorpt_T_min   0.561
_shelx_estimated_absorpt_T_max   0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5415
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39195
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3890
_reflns_number_gt                3205
_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 APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1257P)²+3.3117P] 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         3890
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.2231
_refine_ls_wR_factor_gt          0.2068
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Br1 Br 0.68473(8) 0.89853(7) 0.57584(2) 0.0488(2) Uani 1 1 d . . . . .
N1 N 1.0908(9) 0.6883(8) 0.47294(18) 0.0719(14) Uani 1 1 d . . . . .
N2 N 0.1031(9) 0.6857(8) 0.19937(17) 0.0717(14) Uani 1 1 d . . . . .
C1 C 0.8432(11) 0.6420(9) 0.4014(2) 0.0657(15) Uani 1 1 d . . . . .
C2 C 0.7789(12) 0.7507(10) 0.4334(2) 0.0737(18) Uani 1 1 d . . . . .
H2 H 0.650934 0.809521 0.431230 0.088 Uiso 1 1 calc R U . . .
C3 C 0.9036(12) 0.7719(10) 0.4682(2) 0.0786(19) Uani 1 1 d . . . . .
H3 H 0.858095 0.845879 0.489228 0.094 Uiso 1 1 calc R U . . .
C4 C 1.1541(13) 0.5803(10) 0.4421(3) 0.079(2) Uani 1 1 d . . . . .
H4 H 1.282614 0.522750 0.444828 0.094 Uiso 1 1 calc R U . . .
C5 C 1.0361(12) 0.5541(10) 0.4075(3) 0.081(2) Uani 1 1 d . . . . .
H5 H 1.082955 0.476625 0.387373 0.097 Uiso 1 1 calc R U . . .
C6 C 0.7222(12) 0.6162(8) 0.3630(2) 0.0698(17) Uani 1 1 d . . . . .
H6 H 0.777220 0.540046 0.343408 0.084 Uiso 1 1 calc R U . . .
C7 C 0.5425(10) 0.6917(8) 0.3541(2) 0.0638(15) Uani 1 1 d . . . . .
H7 H 0.482839 0.759646 0.374847 0.077 Uiso 1 1 calc R U . . .
C8 C 0.4263(10) 0.6802(8) 0.31493(19) 0.0588(13) Uani 1 1 d . . . . .
C9 C 0.5018(11) 0.5910(8) 0.2802(2) 0.0651(16) Uani 1 1 d . . . . .
H9 H 0.627292 0.528874 0.282670 0.078 Uiso 1 1 calc R U . . .
C10 C 0.3957(10) 0.5918(8) 0.2422(2) 0.0628(15) Uani 1 1 d . . . . .
H10 H 0.450763 0.530461 0.219830 0.075 Uiso 1 1 calc R U . . .
C11 C 0.2090(10) 0.6830(8) 0.23732(18) 0.0588(13) Uani 1 1 d . . . . .
C12 C 0.1270(11) 0.7684(9) 0.2723(2) 0.0665(15) Uani 1 1 d . . . . .
H12 H -0.001973 0.825737 0.270084 0.080 Uiso 1 1 calc R U . . .
C13 C 0.2349(10) 0.7688(8) 0.3100(2) 0.0653(15) Uani 1 1 d . . . . .
H13 H 0.178890 0.829182 0.332429 0.078 Uiso 1 1 calc R U . . .
C14 C 1.2262(13) 0.7225(12) 0.5098(3) 0.090(2) Uani 1 1 d . . . . .
H14A H 1.296432 0.617242 0.517939 0.135 Uiso 1 1 calc R U . . .
H14B H 1.140563 0.763339 0.532294 0.135 Uiso 1 1 calc R U . . .
H14C H 1.329559 0.808991 0.502945 0.135 Uiso 1 1 calc R U . . .
C15 C -0.1004(11) 0.7657(11) 0.1953(2) 0.0781(19) Uani 1 1 d . . . . .
H15A H -0.164622 0.730686 0.169424 0.117 Uiso 1 1 calc R U . . .
H15B H -0.084638 0.889673 0.195638 0.117 Uiso 1 1 calc R U . . .
H15C H -0.188319 0.730364 0.218001 0.117 Uiso 1 1 calc R U . . .
C16 C 0.2003(15) 0.6157(11) 0.1627(3) 0.087(2) Uani 1 1 d . . . . .
H16A H 0.107843 0.631788 0.139216 0.130 Uiso 1 1 calc R U . . .
H16B H 0.226494 0.493970 0.166664 0.130 Uiso 1 1 calc R U . . .
H16C H 0.331525 0.674495 0.157831 0.130 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
N1 C3 1.356(9) . ?
N1 C4 1.356(9) . ?
N1 C14 1.479(9) . ?
N2 C11 1.387(8) . ?
N2 C15 1.433(9) . ?
N2 C16 1.436(9) . ?
C1 C2 1.389(10) . ?
C1 C5 1.409(10) . ?
C1 C6 1.459(10) . ?
C2 C3 1.374(10) . ?
C4 C5 1.348(11) . ?
C6 C7 1.308(10) . ?
C7 C8 1.454(9) . ?
C8 C9 1.395(9) . ?
C8 C13 1.399(9) . ?
C9 C10 1.389(10) . ?
C10 C11 1.382(9) . ?
C11 C12 1.403(8) . ?
C12 C13 1.386(9) . ?

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
C3 N1 C4 118.2(6) . . ?
C3 N1 C14 120.4(6) . . ?
C4 N1 C14 121.3(6) . . ?
C11 N2 C15 121.1(6) . . ?
C11 N2 C16 120.4(6) . . ?
C15 N2 C16 118.4(6) . . ?
C2 C1 C5 116.4(7) . . ?
C2 C1 C6 123.5(7) . . ?
C5 C1 C6 120.2(6) . . ?
C3 C2 C1 120.3(7) . . ?
N1 C3 C2 122.1(7) . . ?
C5 C4 N1 121.9(7) . . ?
C4 C5 C1 121.2(7) . . ?
C7 C6 C1 125.2(7) . . ?
C6 C7 C8 126.7(6) . . ?
C9 C8 C13 116.8(6) . . ?
C9 C8 C7 123.1(6) . . ?
C13 C8 C7 120.1(6) . . ?
C10 C9 C8 122.2(6) . . ?
C11 C10 C9 120.7(6) . . ?
C10 C11 N2 121.0(6) . . ?
C10 C11 C12 117.9(6) . . ?
N2 C11 C12 121.1(6) . . ?
C13 C12 C11 121.1(6) . . ?
C12 C13 C8 121.3(6) . . ?

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.145

