# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Sivagnana Subramanian'
_publ_contact_author_email       rkureshy@csmcri.org
loop_
_publ_author_name
'Sivagnana Subramanian'
'Rukshana Kureshy'

data_hbrrf
_database_code_depnum_ccdc_archive 'CCDC 867091'
#TrackingRef '- Hbrrf.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H28 Br4 N4'
_chemical_formula_weight         704.15

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pban

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y, -z'
'x, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x-1/2, -y, z'
'-x, y-1/2, z'

_cell_length_a                   17.826(5)
_cell_length_b                   12.506(3)
_cell_length_c                   12.588(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2806.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3266
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      24.18

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_exptl_absorpt_coefficient_mu    5.756
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_correction_T_min  0.2074
_exptl_absorpt_correction_T_max  0.5923

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15615
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0702
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         28.22
_reflns_number_total             3322
_reflns_number_gt                2071
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1018P)^2^+4.2707P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3322
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1936
_refine_ls_wR_factor_gt          0.1740
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.38783(4) 0.43617(5) 0.77676(6) 0.0446(3) Uani 1 d . . .
Br3 Br 0.40404(8) 0.7500 0.0000 0.0723(4) Uani 1 d S . .
Br2 Br 0.62218(6) 0.7500 0.5000 0.0500(3) Uani 1 d S . .
N1 N 0.6254(3) 0.8448(5) 0.2673(4) 0.0423(13) Uani 1 d . . .
H1C H 0.6261 0.8151 0.3290 0.051 Uiso 1 calc R . .
N2 N 0.4683(3) 0.7119(4) 0.2411(4) 0.0359(12) Uani 1 d . . .
H2A H 0.4496 0.7169 0.1748 0.043 Uiso 1 calc R . .
H2B H 0.5090 0.6693 0.2383 0.043 Uiso 1 calc R . .
C1 C 0.6907(4) 0.8754(6) 0.2244(5) 0.0508(18) Uani 1 d . . .
H1 H 0.7356 0.8638 0.2602 0.061 Uiso 1 calc R . .
C2 C 0.6904(5) 0.9243(7) 0.1267(6) 0.063(2) Uani 1 d . . .
H2 H 0.7353 0.9458 0.0958 0.075 Uiso 1 calc R . .
C3 C 0.6237(5) 0.9414(7) 0.0744(6) 0.066(2) Uani 1 d . . .
H3 H 0.6232 0.9747 0.0083 0.080 Uiso 1 calc R . .
C4 C 0.5571(4) 0.9083(6) 0.1216(5) 0.0518(18) Uani 1 d . . .
H4 H 0.5115 0.9200 0.0877 0.062 Uiso 1 calc R . .
C5 C 0.5593(4) 0.8577(5) 0.2196(5) 0.0365(14) Uani 1 d . . .
C6 C 0.4916(4) 0.8203(5) 0.2775(5) 0.0404(15) Uani 1 d . . .
H6A H 0.4508 0.8703 0.2659 0.049 Uiso 1 calc R . .
H6B H 0.5021 0.8183 0.3530 0.049 Uiso 1 calc R . .
C7 C 0.4113(3) 0.6617(5) 0.3111(5) 0.0338(13) Uani 1 d . . .
C8 C 0.4335(4) 0.6134(5) 0.4020(5) 0.0410(15) Uani 1 d . . .
H8 H 0.4838 0.6141 0.4215 0.049 Uiso 1 calc R . .
C9 C 0.3809(4) 0.5630(5) 0.4659(5) 0.0433(16) Uani 1 d . . .
H9 H 0.3959 0.5297 0.5284 0.052 Uiso 1 calc R . .
C10 C 0.3065(3) 0.5621(4) 0.4369(5) 0.0344(13) Uani 1 d . . .
C11 C 0.2851(4) 0.6132(6) 0.3442(5) 0.0470(16) Uani 1 d . . .
H11 H 0.2349 0.6130 0.3240 0.056 Uiso 1 calc R . .
C12 C 0.3374(4) 0.6647(6) 0.2815(5) 0.0448(16) Uani 1 d . . .
H12 H 0.3228 0.7006 0.2202 0.054 Uiso 1 calc R . .
C13 C 0.2500 0.4968(7) 0.5000 0.050(3) Uani 1 d S . .
H13A H 0.2228 0.4510 0.4512 0.060 Uiso 0.50 calc PR . .
H13B H 0.2772 0.4510 0.5488 0.060 Uiso 0.50 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0367(4) 0.0445(4) 0.0524(4) -0.0037(3) 0.0049(3) 0.0001(3)
Br3 0.0726(9) 0.1085(11) 0.0359(6) 0.0101(6) 0.000 0.000
Br2 0.0635(7) 0.0494(6) 0.0371(5) 0.0094(4) 0.000 0.000
N1 0.052(4) 0.043(3) 0.031(3) 0.004(2) 0.003(2) -0.005(3)
N2 0.034(3) 0.043(3) 0.031(3) 0.007(2) 0.008(2) 0.000(2)
C1 0.036(4) 0.066(5) 0.050(4) 0.003(4) 0.000(3) -0.015(3)
C2 0.050(5) 0.091(6) 0.046(4) 0.003(4) 0.009(3) -0.027(4)
C3 0.069(6) 0.092(6) 0.038(4) 0.022(4) 0.005(3) -0.025(4)
C4 0.055(5) 0.063(5) 0.037(3) 0.010(3) -0.006(3) -0.012(4)
C5 0.040(4) 0.032(3) 0.037(3) 0.000(2) 0.010(3) -0.004(3)
C6 0.043(4) 0.032(3) 0.046(4) 0.005(3) 0.015(3) 0.000(3)
C7 0.034(3) 0.033(3) 0.034(3) 0.002(2) 0.008(2) -0.005(2)
C8 0.032(4) 0.052(4) 0.038(3) 0.014(3) -0.003(3) -0.003(3)
C9 0.041(4) 0.055(4) 0.034(3) 0.012(3) 0.006(3) -0.003(3)
C10 0.032(3) 0.027(3) 0.044(3) -0.003(3) 0.015(3) 0.000(2)
C11 0.021(3) 0.061(4) 0.059(4) 0.013(3) 0.005(3) 0.004(3)
C12 0.032(4) 0.054(4) 0.048(4) 0.016(3) 0.003(3) 0.006(3)
C13 0.050(6) 0.028(4) 0.072(6) 0.000 0.033(5) 0.000

_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 C5 1.332(8) . ?
N1 C1 1.341(9) . ?
N1 H1C 0.8600 . ?
N2 C7 1.485(7) . ?
N2 C6 1.491(8) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
C1 C2 1.374(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.485(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.353(8) . ?
C7 C12 1.368(9) . ?
C8 C9 1.388(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(9) . ?
C10 C13 1.521(7) . ?
C11 C12 1.382(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C10 1.521(7) 3_556 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C5 N1 C1 123.5(6) . . ?
C5 N1 H1C 118.2 . . ?
C1 N1 H1C 118.2 . . ?
C7 N2 C6 113.1(4) . . ?
C7 N2 H2A 109.0 . . ?
C6 N2 H2A 109.0 . . ?
C7 N2 H2B 109.0 . . ?
C6 N2 H2B 109.0 . . ?
H2A N2 H2B 107.8 . . ?
N1 C1 C2 118.9(7) . . ?
N1 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
C1 C2 C3 120.2(7) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 119.1(7) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.5(7) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 118.8(6) . . ?
N1 C5 C6 117.3(5) . . ?
C4 C5 C6 123.9(6) . . ?
C5 C6 N2 111.2(5) . . ?
C5 C6 H6A 109.4 . . ?
N2 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
N2 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C12 121.6(6) . . ?
C8 C7 N2 119.3(5) . . ?
C12 C7 N2 119.0(5) . . ?
C7 C8 C9 119.6(6) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.1(6) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.1(6) . . ?
C9 C10 C13 120.2(5) . . ?
C11 C10 C13 120.4(5) . . ?
C12 C11 C10 120.7(6) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C7 C12 C11 118.8(6) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C10 C13 C10 115.1(7) 3_556 . ?
C10 C13 H13A 108.5 3_556 . ?
C10 C13 H13A 108.5 . . ?
C10 C13 H13B 108.5 3_556 . ?
C10 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?

_diffrn_measured_fraction_theta_max 0.853
_diffrn_reflns_theta_full        28.22
_diffrn_measured_fraction_theta_full 0.853
_refine_diff_density_max         2.101
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.156