# Electronic Supplementary Material (ESI) for Green 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_F2_a
_database_code_depnum_ccdc_archive 'CCDC 1887962'
loop_
_audit_author_name
_audit_author_address
'Vandana Rathore'
;IISER Bhopal
India
;
_audit_update_record             
;
2018-12-30 deposited with the CCDC.	2019-03-25 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         'C15 H12 Br N Se'
_chemical_formula_sum            'C15 H12 Br N Se'
_chemical_formula_weight         365.13

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'
Se Se -0.0929 2.2259 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.469(4)
_cell_length_b                   6.265(2)
_cell_length_c                   17.738(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.553(18)
_cell_angle_gamma                90
_cell_volume                     1376.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6300
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.18

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .10
_exptl_crystal_size_min          .09
_exptl_absorpt_coefficient_mu    5.611
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(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            23179
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         28.832
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3581
_reflns_number_gt                2480
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0450P)²+2.5698P] 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         3581
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Se1 Se 0.48060(3) 0.64594(8) 0.59231(2) 0.04270(15) Uani 1 1 d . . . . .
Br1 Br 0.31322(5) 0.26095(9) 0.54261(3) 0.06261(19) Uani 1 1 d . . . . .
N1 N 0.6409(3) 1.1566(6) 0.6874(3) 0.0524(10) Uani 1 1 d . . . . .
H1 H 0.6721 1.2782 0.6842 0.063 Uiso 1 1 calc R U . . .
C10 C 0.5809(3) 0.8515(7) 0.7336(2) 0.0338(8) Uani 1 1 d . . . . .
C6 C 0.3394(3) 0.6528(7) 0.6248(2) 0.0365(9) Uani 1 1 d . . . . .
C7 C 0.5490(3) 0.8620(7) 0.6537(2) 0.0361(9) Uani 1 1 d . . . . .
C11 C 0.5655(3) 0.7058(7) 0.7899(2) 0.0383(9) Uani 1 1 d . . . . .
H11 H 0.5287 0.5790 0.7778 0.046 Uiso 1 1 calc R U . . .
C9 C 0.6379(3) 1.0423(7) 0.7526(3) 0.0417(10) Uani 1 1 d . . . . .
C1 C 0.2680(3) 0.4890(8) 0.6019(2) 0.0453(11) Uani 1 1 d . . . . .
C8 C 0.5872(3) 1.0487(8) 0.6283(3) 0.0471(11) Uani 1 1 d . . . . .
H8 H 0.5779 1.0954 0.5782 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3052(4) 0.8141(8) 0.6687(3) 0.0463(11) Uani 1 1 d . . . . .
H5 H 0.3522 0.9245 0.6848 0.056 Uiso 1 1 calc R U . . .
C14 C 0.6797(4) 1.0866(8) 0.8265(3) 0.0506(12) Uani 1 1 d . . . . .
H14 H 0.7188 1.2106 0.8388 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6049(4) 0.7490(8) 0.8643(3) 0.0491(11) Uani 1 1 d . . . . .
C13 C 0.6611(4) 0.9411(9) 0.8802(3) 0.0555(13) Uani 1 1 d . . . . .
H13 H 0.6871 0.9702 0.9304 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2010(4) 0.8141(10) 0.6894(3) 0.0610(14) Uani 1 1 d . . . . .
H4 H 0.1784 0.9237 0.7192 0.073 Uiso 1 1 calc R U . . .
C2 C 0.1648(4) 0.4884(10) 0.6220(3) 0.0633(15) Uani 1 1 d . . . . .
H2 H 0.1177 0.3779 0.6063 0.076 Uiso 1 1 calc R U . . .
C3 C 0.1317(4) 0.6510(11) 0.6654(3) 0.0678(16) Uani 1 1 d . . . . .
H3 H 0.0617 0.6511 0.6788 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5868(5) 0.5953(11) 0.9272(3) 0.0740(18) Uani 1 1 d . . . . .
H15A H 0.5562 0.6704 0.9668 0.111 Uiso 1 1 calc R U . . .
H15B H 0.6545 0.5332 0.9473 0.111 Uiso 1 1 calc R U . . .
H15C H 0.5383 0.4845 0.9075 0.111 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
Se1 C7 1.880(4) . ?
Se1 C6 1.914(4) . ?
Br1 C1 1.898(5) . ?
N1 C8 1.358(6) . ?
N1 C9 1.365(6) . ?
N1 H1 0.8600 . ?
C10 C11 1.383(6) . ?
C10 C9 1.412(6) . ?
C10 C7 1.429(6) . ?
C6 C5 1.374(7) . ?
C6 C1 1.389(6) . ?
C7 C8 1.359(6) . ?
C11 C12 1.380(6) . ?
C11 H11 0.9300 . ?
C9 C14 1.382(7) . ?
C1 C2 1.374(7) . ?
C8 H8 0.9300 . ?
C5 C4 1.388(7) . ?
C5 H5 0.9300 . ?
C14 C13 1.358(8) . ?
C14 H14 0.9300 . ?
C12 C13 1.405(8) . ?
C12 C15 1.510(8) . ?
C13 H13 0.9300 . ?
C4 C3 1.374(8) . ?
C4 H4 0.9300 . ?
C2 C3 1.368(9) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 Se1 C6 100.45(18) . . ?
C8 N1 C9 109.5(4) . . ?
C8 N1 H1 125.2 . . ?
C9 N1 H1 125.2 . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 C7 134.5(4) . . ?
C9 C10 C7 105.9(4) . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 Se1 122.9(3) . . ?
C1 C6 Se1 118.5(4) . . ?
C8 C7 C10 107.5(4) . . ?
C8 C7 Se1 125.5(3) . . ?
C10 C7 Se1 126.7(3) . . ?
C12 C11 C10 119.8(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N1 C9 C14 130.9(4) . . ?
N1 C9 C10 107.7(4) . . ?
C14 C9 C10 121.5(4) . . ?
C2 C1 C6 121.0(5) . . ?
C2 C1 Br1 119.2(4) . . ?
C6 C1 Br1 119.8(3) . . ?
N1 C8 C7 109.5(4) . . ?
N1 C8 H8 125.3 . . ?
C7 C8 H8 125.3 . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C13 C14 C9 117.0(4) . . ?
C13 C14 H14 121.5 . . ?
C9 C14 H14 121.5 . . ?
C11 C12 C13 118.4(5) . . ?
C11 C12 C15 120.9(5) . . ?
C13 C12 C15 120.7(5) . . ?
C14 C13 C12 123.7(5) . . ?
C14 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         1.433
_refine_diff_density_min         -1.278
_refine_diff_density_rms         0.111

