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


data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_cambridge         1145
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Zhen Fang'
_publ_contact_author_email       fangzh78@unc.edu
loop_
_publ_author_name
'Zhen Fang'
'Vijila Chellapan'
'Richard Webster'
'Lin Ke'
'Tianfu Zhang'
'Bin Liu'
'Yee-Hing Lai'

data_4320
_database_code_depnum_ccdc_archive 'CCDC 794931'
#TrackingRef 'XRD-Cpd-10.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 Br3 N'
_chemical_formula_weight         602.20

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   P2(1)2(1)2(1)

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

_cell_length_a                   7.5089(4)
_cell_length_b                   14.4140(7)
_cell_length_c                   21.5562(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2333.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3750
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      24.75

_exptl_crystal_description       'LONG ROD'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    5.203
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_correction_T_min  0.2301
_exptl_absorpt_correction_T_max  0.4544
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16571
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5340
_reflns_number_gt                4381
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0212P)^2^+0.7458P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(10)
_refine_ls_number_reflns         5340
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.79639(6) -0.16221(3) 0.35814(2) 0.05282(13) Uani 1 1 d . . .
Br2 Br -0.26459(6) 0.21982(3) 0.165391(15) 0.04644(12) Uani 1 1 d . . .
Br3 Br -0.21936(8) 0.09910(5) 0.649541(18) 0.0811(2) Uani 1 1 d . . .
N1 N 0.0900(4) 0.0424(2) 0.39089(12) 0.0264(6) Uani 1 1 d . . .
C1 C 0.2493(5) -0.0105(2) 0.38268(13) 0.0250(7) Uani 1 1 d . . .
C2 C 0.3262(5) -0.0578(2) 0.43312(15) 0.0288(8) Uani 1 1 d . . .
C3 C 0.4879(5) -0.1026(2) 0.42496(16) 0.0341(8) Uani 1 1 d . . .
H3 H 0.5397 -0.1337 0.4582 0.041 Uiso 1 1 calc R . .
C4 C 0.5724(5) -0.1019(2) 0.36874(17) 0.0333(8) Uani 1 1 d . . .
C5 C 0.4936(5) -0.0605(3) 0.31889(16) 0.0335(8) Uani 1 1 d . . .
H5 H 0.5500 -0.0621 0.2805 0.040 Uiso 1 1 calc R . .
C6 C 0.3315(5) -0.0165(2) 0.32464(15) 0.0273(7) Uani 1 1 d . . .
C7 C 0.2480(5) 0.0199(2) 0.26550(14) 0.0302(8) Uani 1 1 d . . .
C8 C 0.0772(5) 0.0719(2) 0.27886(16) 0.0277(8) Uani 1 1 d . . .
C9 C -0.0105(5) 0.1111(3) 0.22858(16) 0.0339(8) Uani 1 1 d . . .
H9 H 0.0319 0.1000 0.1887 0.041 Uiso 1 1 calc R . .
C10 C -0.1568(5) 0.1653(3) 0.23636(15) 0.0343(8) Uani 1 1 d . . .
C11 C -0.2180(5) 0.1845(2) 0.29465(14) 0.0326(8) Uani 1 1 d . . .
H11 H -0.3140 0.2246 0.2997 0.039 Uiso 1 1 calc R . .
C12 C -0.1383(4) 0.1448(2) 0.34644(14) 0.0266(7) Uani 1 1 d . . .
C13 C 0.0099(5) 0.0866(2) 0.33924(14) 0.0258(7) Uani 1 1 d . . .
C14 C -0.2085(5) 0.1732(2) 0.40963(14) 0.0274(7) Uani 1 1 d . . .
C15 C -0.1228(5) 0.1173(3) 0.46083(15) 0.0296(8) Uani 1 1 d . . .
C16 C 0.0180(5) 0.0551(2) 0.45111(14) 0.0275(7) Uani 1 1 d . . .
C17 C 0.0865(5) 0.0045(3) 0.50181(15) 0.0304(8) Uani 1 1 d . . .
C18 C 0.0113(6) 0.0174(3) 0.56036(16) 0.0437(10) Uani 1 1 d . . .
H18 H 0.0528 -0.0173 0.5937 0.052 Uiso 1 1 calc R . .
C19 C -0.1216(6) 0.0797(3) 0.56937(16) 0.0470(11) Uani 1 1 d . . .
C20 C -0.1875(6) 0.1299(3) 0.52009(16) 0.0429(10) Uani 1 1 d . . .
H20 H -0.2774 0.1731 0.5269 0.052 Uiso 1 1 calc R . .
C21 C 0.2355(5) -0.0662(2) 0.49585(14) 0.0345(8) Uani 1 1 d . . .
C22 C 0.2062(6) -0.0638(3) 0.22323(16) 0.0430(9) Uani 1 1 d . . .
H22A H 0.1312 -0.1067 0.2451 0.065 Uiso 1 1 calc R . .
H22B H 0.3152 -0.0941 0.2118 0.065 Uiso 1 1 calc R . .
H22C H 0.1461 -0.0427 0.1865 0.065 Uiso 1 1 calc R . .
C23 C 0.3762(5) 0.0870(3) 0.23314(18) 0.0432(10) Uani 1 1 d . . .
H23A H 0.3234 0.1088 0.1953 0.065 Uiso 1 1 calc R . .
H23B H 0.4857 0.0554 0.2239 0.065 Uiso 1 1 calc R . .
H23C H 0.4000 0.1387 0.2599 0.065 Uiso 1 1 calc R . .
C24 C -0.1699(6) 0.2769(3) 0.42001(18) 0.0484(10) Uani 1 1 d . . .
H24A H -0.2077 0.2944 0.4609 0.073 Uiso 1 1 calc R . .
H24B H -0.2334 0.3129 0.3898 0.073 Uiso 1 1 calc R . .
H24C H -0.0444 0.2880 0.4158 0.073 Uiso 1 1 calc R . .
C25 C -0.4127(5) 0.1589(3) 0.41173(17) 0.0415(9) Uani 1 1 d . . .
H25A H -0.4393 0.0941 0.4074 0.062 Uiso 1 1 calc R . .
H25B H -0.4673 0.1928 0.3784 0.062 Uiso 1 1 calc R . .
H25C H -0.4581 0.1810 0.4506 0.062 Uiso 1 1 calc R . .
C26 C 0.3732(7) -0.0516(4) 0.54806(19) 0.0664(15) Uani 1 1 d . . .
H26A H 0.4607 -0.1001 0.5465 0.100 Uiso 1 1 calc R . .
H26B H 0.3141 -0.0530 0.5875 0.100 Uiso 1 1 calc R . .
H26C H 0.4306 0.0073 0.5427 0.100 Uiso 1 1 calc R . .
C27 C 0.1548(8) -0.1641(3) 0.5012(2) 0.0614(13) Uani 1 1 d . . .
H27A H 0.0672 -0.1726 0.4693 0.092 Uiso 1 1 calc R . .
H27B H 0.0997 -0.1711 0.5411 0.092 Uiso 1 1 calc R . .
H27C H 0.2473 -0.2096 0.4966 0.092 Uiso 1 1 calc R . .

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 0.0403(2) 0.0604(3) 0.0578(3) 0.0061(2) 0.0032(2) 0.0200(2)
Br2 0.0533(3) 0.0569(2) 0.02914(17) 0.01423(17) -0.00760(18) 0.0117(2)
Br3 0.0678(3) 0.1497(5) 0.02591(19) 0.0195(3) 0.0152(2) 0.0498(3)
N1 0.0317(16) 0.0288(16) 0.0186(13) 0.0007(11) -0.0016(11) 0.0003(13)
C1 0.0223(17) 0.0281(17) 0.0247(15) -0.0031(12) -0.0030(14) -0.0025(14)
C2 0.034(2) 0.0268(18) 0.0257(17) 0.0006(14) -0.0034(14) -0.0021(15)
C3 0.036(2) 0.034(2) 0.0329(19) 0.0054(17) -0.0063(16) 0.0039(17)
C4 0.0284(19) 0.031(2) 0.040(2) -0.0016(17) -0.0015(16) 0.0080(15)
C5 0.035(2) 0.039(2) 0.0270(18) -0.0011(15) 0.0030(15) 0.0007(17)
C6 0.0297(19) 0.0278(18) 0.0244(16) -0.0024(14) -0.0038(14) -0.0011(14)
C7 0.035(2) 0.0325(18) 0.0229(14) -0.0015(13) -0.0015(15) 0.0033(16)
C8 0.0275(18) 0.0292(19) 0.0264(17) 0.0015(14) -0.0018(14) -0.0031(15)
C9 0.036(2) 0.043(2) 0.0220(16) 0.0008(15) 0.0018(15) 0.0029(18)
C10 0.041(2) 0.038(2) 0.0246(17) 0.0093(16) -0.0094(15) 0.0045(18)
C11 0.034(2) 0.0345(19) 0.0291(16) 0.0016(13) -0.0066(16) 0.0027(16)
C12 0.0268(17) 0.0309(19) 0.0220(16) 0.0043(14) -0.0012(13) -0.0021(14)
C13 0.0298(17) 0.0239(17) 0.0237(16) -0.0002(13) -0.0056(14) -0.0016(13)
C14 0.0279(18) 0.0298(18) 0.0243(15) 0.0005(13) -0.0017(14) 0.0014(15)
C15 0.0297(19) 0.035(2) 0.0237(17) 0.0011(14) 0.0009(14) 0.0011(16)
C16 0.0298(19) 0.0324(19) 0.0203(16) 0.0002(14) -0.0007(14) -0.0013(16)
C17 0.033(2) 0.036(2) 0.0221(17) 0.0050(15) -0.0017(14) -0.0028(16)
C18 0.044(2) 0.066(3) 0.0214(18) 0.0119(18) 0.0004(17) 0.006(2)
C19 0.043(2) 0.078(3) 0.0205(18) 0.0083(19) 0.0127(16) 0.011(2)
C20 0.040(2) 0.058(3) 0.0310(19) 0.0017(17) 0.0020(17) 0.015(2)
C21 0.041(2) 0.039(2) 0.0241(15) 0.0046(13) -0.0046(16) 0.0012(19)
C22 0.054(2) 0.044(2) 0.0313(18) -0.0089(15) -0.0089(19) 0.010(2)
C23 0.041(2) 0.053(3) 0.036(2) 0.0069(19) 0.0003(18) 0.0035(19)
C24 0.070(3) 0.039(2) 0.036(2) -0.0011(19) -0.004(2) -0.008(2)
C25 0.034(2) 0.059(3) 0.0315(19) -0.002(2) 0.0007(16) 0.005(2)
C26 0.058(3) 0.110(4) 0.031(2) -0.017(2) -0.016(2) 0.036(3)
C27 0.087(4) 0.040(2) 0.057(3) 0.016(2) 0.023(2) -0.002(3)

_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 C4 1.907(3) . ?
Br2 C10 1.901(3) . ?
Br3 C19 1.898(4) . ?
N1 C13 1.417(4) . ?
N1 C16 1.418(4) . ?
N1 C1 1.429(4) . ?
C1 C6 1.397(4) . ?
C1 C2 1.407(4) . ?
C2 C3 1.387(5) . ?
C2 C21 1.519(5) . ?
C3 C4 1.368(5) . ?
C4 C5 1.364(5) . ?
C5 C6 1.379(5) . ?
C6 C7 1.514(4) . ?
C7 C8 1.513(5) . ?
C7 C23 1.532(5) . ?
C7 C22 1.545(5) . ?
C8 C9 1.388(5) . ?
C8 C13 1.412(5) . ?
C9 C10 1.359(5) . ?
C10 C11 1.366(5) . ?
C11 C12 1.390(4) . ?
C12 C13 1.403(5) . ?
C12 C14 1.517(4) . ?
C14 C15 1.510(5) . ?
C14 C24 1.538(5) . ?
C14 C25 1.548(5) . ?
C15 C20 1.379(5) . ?
C15 C16 1.402(5) . ?
C16 C17 1.411(5) . ?
C17 C18 1.395(5) . ?
C17 C21 1.519(5) . ?
C18 C19 1.357(6) . ?
C19 C20 1.377(5) . ?
C21 C27 1.540(5) . ?
C21 C26 1.543(5) . ?

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
C13 N1 C16 119.9(3) . . ?
C13 N1 C1 119.9(3) . . ?
C16 N1 C1 120.1(3) . . ?
C6 C1 C2 118.7(3) . . ?
C6 C1 N1 120.9(3) . . ?
C2 C1 N1 120.4(3) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 C21 117.9(3) . . ?
C1 C2 C21 122.9(3) . . ?
C4 C3 C2 121.0(3) . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 Br1 119.2(3) . . ?
C3 C4 Br1 120.8(3) . . ?
C4 C5 C6 120.9(3) . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 C7 116.7(3) . . ?
C1 C6 C7 123.4(3) . . ?
C8 C7 C6 111.2(3) . . ?
C8 C7 C23 107.9(3) . . ?
C6 C7 C23 110.0(3) . . ?
C8 C7 C22 109.0(3) . . ?
C6 C7 C22 108.0(3) . . ?
C23 C7 C22 110.6(3) . . ?
C9 C8 C13 119.3(3) . . ?
C9 C8 C7 117.0(3) . . ?
C13 C8 C7 123.6(3) . . ?
C10 C9 C8 121.4(3) . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 Br2 118.9(3) . . ?
C11 C10 Br2 120.9(3) . . ?
C10 C11 C12 120.7(3) . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 C14 117.4(3) . . ?
C13 C12 C14 122.4(3) . . ?
C12 C13 C8 118.4(3) . . ?
C12 C13 N1 121.3(3) . . ?
C8 C13 N1 120.3(3) . . ?
C15 C14 C12 111.4(3) . . ?
C15 C14 C24 109.4(3) . . ?
C12 C14 C24 109.1(3) . . ?
C15 C14 C25 109.2(3) . . ?
C12 C14 C25 109.5(3) . . ?
C24 C14 C25 108.2(3) . . ?
C20 C15 C16 119.2(3) . . ?
C20 C15 C14 117.2(3) . . ?
C16 C15 C14 123.6(3) . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 N1 120.5(3) . . ?
C17 C16 N1 120.2(3) . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 C21 117.6(3) . . ?
C16 C17 C21 123.4(3) . . ?
C19 C18 C17 121.0(3) . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 Br3 120.8(3) . . ?
C20 C19 Br3 119.0(3) . . ?
C19 C20 C15 121.2(4) . . ?
C2 C21 C17 110.6(3) . . ?
C2 C21 C27 108.5(3) . . ?
C17 C21 C27 108.6(4) . . ?
C2 C21 C26 109.7(3) . . ?
C17 C21 C26 109.9(3) . . ?
C27 C21 C26 109.5(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.069