# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_arijit1_0m
_database_code_depnum_ccdc_archive 'CCDC 986120'
_audit_update_record             
;
2014-02-10 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 Br Cl N2'
_chemical_formula_sum            'C25 H17 Br Cl N2'
_chemical_formula_weight         460.76

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.802(3)
_cell_length_b                   9.833(3)
_cell_length_c                   12.388(4)
_cell_angle_alpha                85.599(15)
_cell_angle_beta                 70.767(13)
_cell_angle_gamma                67.602(14)
_cell_volume                     1040.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3823
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      23.84

_exptl_crystal_description       ?
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.018
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             466
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14609
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.65
_reflns_number_total             4646
_reflns_number_gt                3035
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0826P)²+0.1119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4646
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.066
_refine_ls_shift/su_mean         0.006

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.29925(4) 0.24296(4) 0.00209(3) 0.06741(18) Uani 1 1 d . . .
Cl1 Cl 0.82011(11) 0.79638(12) 0.44890(9) 0.0760(3) Uani 1 1 d . . .
C19 C 0.2890(4) 0.8655(4) 0.8237(3) 0.0575(9) Uani 1 1 d . . .
N2 N 0.1389(3) 0.8086(3) 0.5080(2) 0.0490(6) Uani 1 1 d . . .
H2 H 0.0486 0.8038 0.5243 0.059 Uiso 1 1 calc R . .
C1 C 0.2575(5) 0.9783(4) 0.2350(3) 0.0615(9) Uani 1 1 d . . .
H1 H 0.2266 1.0212 0.1730 0.074 Uiso 1 1 calc R . .
C2 C 0.1601(4) 0.9275(4) 0.3196(3) 0.0556(8) Uani 1 1 d . . .
H2A H 0.0645 0.9340 0.3160 0.067 Uiso 1 1 calc R . .
C3 C 0.2112(3) 0.8655(3) 0.4114(2) 0.0415(6) Uani 1 1 d . . .
C4 C 0.3561(3) 0.8523(3) 0.4180(2) 0.0379(6) Uani 1 1 d . . .
C5 C 0.3699(3) 0.7827(3) 0.5218(2) 0.0366(6) Uani 1 1 d . . .
C6 C 0.5130(3) 0.7329(3) 0.5603(2) 0.0379(6) Uani 1 1 d . . .
H6 H 0.5330 0.8198 0.5726 0.045 Uiso 1 1 calc R . .
C7 C 0.6509(3) 0.6341(3) 0.4655(2) 0.0392(6) Uani 1 1 d . . .
H7 H 0.6394 0.5522 0.4426 0.047 Uiso 1 1 calc R . .
C8 C 0.7847(3) 0.6471(3) 0.4106(2) 0.0403(6) Uani 1 1 d . . .
C9 C 0.9098(3) 0.5498(3) 0.3140(2) 0.0400(6) Uani 1 1 d . . .
C10 C 1.0663(4) 0.4967(4) 0.3069(3) 0.0542(8) Uani 1 1 d . . .
H10 H 1.0939 0.5247 0.3641 0.065 Uiso 1 1 calc R . .
C11 C 1.1814(4) 0.4026(4) 0.2162(3) 0.0576(9) Uani 1 1 d . . .
H11 H 1.2851 0.3657 0.2134 0.069 Uiso 1 1 calc R . .
C12 C 1.1403(4) 0.3645(4) 0.1305(2) 0.0477(7) Uani 1 1 d . . .
C13 C 0.4905(3) 0.6538(3) 0.6704(2) 0.0373(6) Uani 1 1 d . . .
C14 C 0.3889(3) 0.7198(3) 0.7824(2) 0.0406(6) Uani 1 1 d . . .
C15 C 0.2083(5) 0.8881(5) 0.9410(3) 0.0748(12) Uani 1 1 d . . .
H15 H 0.1429 0.9832 0.9714 0.090 Uiso 1 1 calc R . .
C16 C 0.2231(5) 0.7709(6) 1.0145(3) 0.0776(13) Uani 1 1 d . . .
H16 H 0.1657 0.7905 1.0919 0.093 Uiso 1 1 calc R . .
C17 C 0.3191(5) 0.6292(5) 0.9757(3) 0.0640(10) Uani 1 1 d . . .
H17 H 0.3283 0.5525 1.0250 0.077 Uiso 1 1 calc R . .
C18 C 0.4031(4) 0.6043(4) 0.8583(2) 0.0470(7) Uani 1 1 d . . .
N1 N 0.5062(3) 0.4771(3) 0.7960(2) 0.0525(7) Uani 1 1 d . . .
H19 H 0.5340 0.3912 0.8230 0.063 Uiso 1 1 calc R . .
C20 C 0.5588(4) 0.5075(4) 0.6834(3) 0.0463(7) Uani 1 1 d . . .
H20 H 0.6307 0.4381 0.6246 0.056 Uiso 1 1 calc R . .
C21 C 0.2347(3) 0.7607(3) 0.5740(2) 0.0427(7) Uani 1 1 d . . .
H21 H 0.2107 0.7191 0.6443 0.051 Uiso 1 1 calc R . .
C22 C 0.4024(4) 0.9671(4) 0.2395(3) 0.0561(8) Uani 1 1 d . . .
H22 H 0.4652 1.0029 0.1806 0.067 Uiso 1 1 calc R . .
C23 C 0.4535(4) 0.9047(4) 0.3286(2) 0.0475(7) Uani 1 1 d . . .
H23 H 0.5504 0.8969 0.3302 0.057 Uiso 1 1 calc R . .
C24 C 0.8728(3) 0.5058(4) 0.2265(2) 0.0477(7) Uani 1 1 d . . .
H24 H 0.7689 0.5399 0.2298 0.057 Uiso 1 1 calc R . .
C25 C 0.9859(4) 0.4132(4) 0.1355(2) 0.0507(8) Uani 1 1 d . . .
H25 H 0.9591 0.3839 0.0783 0.061 Uiso 1 1 calc R . .


_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 C12 1.904(3) . ?
Cl1 C8 1.762(3) . ?
C19 C15 1.395(5) . ?
C19 C14 1.409(5) . ?
N2 C21 1.371(4) . ?
N2 C3 1.373(4) . ?
N2 H2 0.8600 . ?
C1 C2 1.373(5) . ?
C1 C22 1.402(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.406(4) . ?
C4 C23 1.413(4) . ?
C4 C5 1.432(4) . ?
C5 C21 1.362(4) . ?
C5 C6 1.521(4) . ?
C6 C7 1.510(4) . ?
C6 C13 1.511(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.314(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.472(4) . ?
C9 C10 1.393(4) . ?
C9 C24 1.394(4) . ?
C10 C11 1.386(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9300 . ?
C12 C25 1.383(5) . ?
C13 C20 1.358(4) . ?
C13 C14 1.440(4) . ?
C14 C18 1.413(4) . ?
C15 C16 1.405(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.401(4) . ?
C17 H17 0.9300 . ?
C18 N1 1.362(4) . ?
N1 C20 1.372(4) . ?
N1 H19 0.8600 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.368(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.377(4) . ?
C24 H24 0.9300 . ?
C25 H25 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
C15 C19 C14 116.9(4) . . ?
C21 N2 C3 108.7(2) . . ?
C21 N2 H2 125.6 . . ?
C3 N2 H2 125.6 . . ?
C2 C1 C22 121.7(3) . . ?
C2 C1 H1 119.2 . . ?
C22 C1 H1 119.2 . . ?
C1 C2 C3 116.9(3) . . ?
C1 C2 H2A 121.5 . . ?
C3 C2 H2A 121.5 . . ?
N2 C3 C2 129.9(3) . . ?
N2 C3 C4 107.4(2) . . ?
C2 C3 C4 122.6(3) . . ?
C3 C4 C23 118.7(3) . . ?
C3 C4 C5 107.3(2) . . ?
C23 C4 C5 134.1(3) . . ?
C21 C5 C4 106.2(2) . . ?
C21 C5 C6 127.3(3) . . ?
C4 C5 C6 126.3(2) . . ?
C7 C6 C13 110.6(2) . . ?
C7 C6 C5 108.2(2) . . ?
C13 C6 C5 112.0(2) . . ?
C7 C6 H6 108.6 . . ?
C13 C6 H6 108.6 . . ?
C5 C6 H6 108.6 . . ?
C8 C7 C6 129.3(3) . . ?
C8 C7 H7 115.4 . . ?
C6 C7 H7 115.4 . . ?
C7 C8 C9 125.7(3) . . ?
C7 C8 Cl1 119.1(2) . . ?
C9 C8 Cl1 115.10(19) . . ?
C10 C9 C24 117.8(3) . . ?
C10 C9 C8 122.4(3) . . ?
C24 C9 C8 119.8(2) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C25 121.3(3) . . ?
C11 C12 Br1 119.3(2) . . ?
C25 C12 Br1 119.5(2) . . ?
C20 C13 C14 106.6(3) . . ?
C20 C13 C6 127.3(3) . . ?
C14 C13 C6 126.2(3) . . ?
C19 C14 C18 120.2(3) . . ?
C19 C14 C13 133.3(3) . . ?
C18 C14 C13 106.4(3) . . ?
C16 C15 C19 121.7(4) . . ?
C16 C15 H15 119.1 . . ?
C19 C15 H15 119.1 . . ?
C17 C16 C15 122.1(3) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C16 C17 C18 117.1(4) . . ?
C16 C17 H17 121.4 . . ?
C18 C17 H17 121.4 . . ?
N1 C18 C17 130.3(3) . . ?
N1 C18 C14 107.8(3) . . ?
C17 C18 C14 121.9(3) . . ?
C18 N1 C20 109.2(3) . . ?
C18 N1 H19 125.4 . . ?
C20 N1 H19 125.4 . . ?
N1 C20 C13 110.1(3) . . ?
N1 C20 H20 125.0 . . ?
C13 C20 H20 125.0 . . ?
C5 C21 N2 110.3(2) . . ?
C5 C21 H21 124.8 . . ?
N2 C21 H21 124.8 . . ?
C23 C22 C1 121.5(3) . . ?
C23 C22 H22 119.3 . . ?
C1 C22 H22 119.2 . . ?
C22 C23 C4 118.6(3) . . ?
C22 C23 H23 120.7 . . ?
C4 C23 H23 120.7 . . ?
C25 C24 C9 121.7(3) . . ?
C25 C24 H24 119.1 . . ?
C9 C24 H24 119.1 . . ?
C24 C25 C12 118.8(3) . . ?
C24 C25 H25 120.6 . . ?
C12 C25 H25 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.063
