# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2009


data_global

_journal_coden_Cambridge         1145
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Jih Hwu.'
'Yung Chang Hsu.'
'Thainashmuthu Josephrajan'
'Shwu-Chen Tsay.'

_publ_contact_author_name        'Jih Hwu'
_publ_contact_author_email       JRHWU@MX.NTHU.EDU.TW

_publ_section_title              
;
Fine tuning of blue photoluminescence
from indoles for device fabrication
;

# Attachment 'Hwu_JMC-B821246E-X-ray_data_1.cif'

data_mr62m
_database_code_depnum_ccdc_archive 'CCDC 718748'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Cl2 N O6'
_chemical_formula_weight         454.29

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.3962(19)
_cell_length_b                   14.120(2)
_cell_length_c                   13.920(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.759(4)
_cell_angle_gamma                90.00
_cell_volume                     2212.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2904
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.91053
_exptl_absorpt_correction_T_max  0.97617
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(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            12646
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.08
_reflns_number_total             3927
_reflns_number_gt                2468
_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^)+(0.1481P)^2^+0.0000P] 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_number_reflns         3927
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2365
_refine_ls_wR_factor_gt          0.2158
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.46265(16) 0.6281(2) 1.18718(16) 0.2029(11) Uani 1 1 d . . .
Cl2 Cl -0.3452(4) 0.5981(2) 1.0515(3) 0.2824(19) Uani 1 1 d . . .
O1 O 0.4284(2) 0.71462(19) 0.40349(19) 0.0756(7) Uani 1 1 d . . .
O2 O 0.52060(19) 0.60392(17) 0.56419(19) 0.0721(7) Uani 1 1 d . . .
O3 O 0.2139(2) 0.40428(16) 0.5528(2) 0.0733(7) Uani 1 1 d . . .
O4 O 0.1451(2) 0.33249(15) 0.6589(2) 0.0703(7) Uani 1 1 d . . .
O5 O -0.0765(3) 0.35177(17) 0.8756(2) 0.0860(8) Uani 1 1 d . . .
O6 O -0.1640(2) 0.47869(18) 0.9035(2) 0.0825(8) Uani 1 1 d . . .
N1 N 0.0829(2) 0.65128(17) 0.6304(2) 0.0571(7) Uani 1 1 d . . .
H1A H 0.0787 0.7103 0.6140 0.068 Uiso 1 1 calc R . .
C1 C 0.1670(3) 0.6757(2) 0.4591(2) 0.0579(8) Uani 1 1 d . . .
H1B H 0.0878 0.6938 0.4345 0.070 Uiso 1 1 calc R . .
C2 C 0.2346(3) 0.7097(2) 0.4092(3) 0.0619(8) Uani 1 1 d . . .
H2A H 0.2007 0.7498 0.3511 0.074 Uiso 1 1 calc R . .
C3 C 0.3529(3) 0.6842(2) 0.4456(3) 0.0581(8) Uani 1 1 d . . .
C4 C 0.4022(3) 0.6242(2) 0.5331(2) 0.0563(8) Uani 1 1 d . . .
C5 C 0.3341(3) 0.5896(2) 0.5816(3) 0.0561(8) Uani 1 1 d . . .
H5A H 0.3672 0.5488 0.6392 0.067 Uiso 1 1 calc R . .
C6 C 0.2139(3) 0.6161(2) 0.5438(2) 0.0536(8) Uani 1 1 d . . .
C7 C 0.1438(3) 0.5845(2) 0.6014(2) 0.0524(7) Uani 1 1 d . . .
C8 C 0.1264(3) 0.4982(2) 0.6396(2) 0.0525(8) Uani 1 1 d . . .
C9 C 0.0560(2) 0.5142(2) 0.6971(2) 0.0507(7) Uani 1 1 d . . .
C10 C 0.0120(3) 0.4570(2) 0.7543(2) 0.0545(8) Uani 1 1 d . . .
H10A H 0.0274 0.3923 0.7603 0.065 Uiso 1 1 calc R . .
C11 C -0.0552(3) 0.49793(19) 0.8023(2) 0.0539(8) Uani 1 1 d . . .
C12 C -0.0788(3) 0.5960(2) 0.7934(3) 0.0584(8) Uani 1 1 d . . .
H12A H -0.1233 0.6223 0.8263 0.070 Uiso 1 1 calc R . .
C13 C -0.0373(3) 0.6532(2) 0.7371(3) 0.0590(8) Uani 1 1 d . . .
H13A H -0.0530 0.7179 0.7309 0.071 Uiso 1 1 calc R . .
C14 C 0.0295(3) 0.6111(2) 0.6892(2) 0.0532(8) Uani 1 1 d . . .
C15 C 0.3817(4) 0.7783(4) 0.3169(4) 0.1089(16) Uani 1 1 d . . .
H15A H 0.4425 0.7943 0.2940 0.163 Uiso 1 1 calc R . .
H15B H 0.3547 0.8348 0.3383 0.163 Uiso 1 1 calc R . .
H15C H 0.3164 0.7490 0.2597 0.163 Uiso 1 1 calc R . .
C16 C 0.5762(3) 0.5430(3) 0.6518(3) 0.0855(12) Uani 1 1 d . . .
H16A H 0.6581 0.5347 0.6649 0.128 Uiso 1 1 calc R . .
H16B H 0.5369 0.4826 0.6368 0.128 Uiso 1 1 calc R . .
H16C H 0.5715 0.5702 0.7131 0.128 Uiso 1 1 calc R . .
C17 C 0.1624(3) 0.4037(2) 0.6203(3) 0.0568(8) Uani 1 1 d . . .
C18 C 0.2542(4) 0.3144(3) 0.5315(3) 0.0869(12) Uani 1 1 d . . .
H18A H 0.2896 0.3232 0.4826 0.130 Uiso 1 1 calc R . .
H18B H 0.1879 0.2719 0.5014 0.130 Uiso 1 1 calc R . .
H18C H 0.3119 0.2881 0.5962 0.130 Uiso 1 1 calc R . .
C19 C -0.0987(3) 0.4349(2) 0.8624(2) 0.0594(8) Uani 1 1 d . . .
C20 C -0.2086(4) 0.4199(3) 0.9636(4) 0.0955(13) Uani 1 1 d . . .
H20A H -0.2544 0.4579 0.9901 0.143 Uiso 1 1 calc R . .
H20D H -0.1432 0.3918 1.0218 0.143 Uiso 1 1 calc R . .
H20B H -0.2580 0.3709 0.9189 0.143 Uiso 1 1 calc R . .
C21 C -0.3813(5) 0.6701(4) 1.1223(5) 0.1259(19) Uani 1 1 d . . .
H21A H -0.4259 0.7216 1.0768 0.151 Uiso 1 1 calc R . .
H21B H -0.3087 0.6971 1.1749 0.151 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
Cl1 0.1092(13) 0.335(3) 0.1573(16) 0.0465(18) 0.0488(12) -0.0225(15)
Cl2 0.416(5) 0.182(2) 0.331(4) 0.008(2) 0.236(4) 0.116(3)
O1 0.0628(14) 0.0909(18) 0.0805(16) 0.0229(13) 0.0374(13) 0.0028(12)
O2 0.0477(13) 0.0818(16) 0.0846(16) 0.0173(13) 0.0257(12) 0.0029(11)
O3 0.0900(18) 0.0577(15) 0.0915(17) -0.0064(11) 0.0570(15) 0.0010(11)
O4 0.0788(16) 0.0457(13) 0.1006(18) 0.0033(12) 0.0515(14) 0.0017(11)
O5 0.122(2) 0.0487(14) 0.120(2) 0.0010(14) 0.0827(19) -0.0025(13)
O6 0.0968(19) 0.0641(15) 0.117(2) 0.0054(14) 0.0742(18) 0.0045(13)
N1 0.0559(15) 0.0397(13) 0.0775(17) 0.0046(12) 0.0297(14) 0.0003(11)
C1 0.0474(17) 0.0599(19) 0.066(2) 0.0041(15) 0.0229(15) 0.0020(14)
C2 0.058(2) 0.064(2) 0.0589(19) 0.0094(15) 0.0199(16) 0.0022(16)
C3 0.0545(18) 0.0582(19) 0.0634(19) 0.0033(15) 0.0266(16) -0.0049(14)
C4 0.0435(17) 0.0580(18) 0.0644(19) 0.0001(15) 0.0197(15) -0.0033(13)
C5 0.0482(17) 0.0544(18) 0.0611(19) 0.0037(14) 0.0183(15) -0.0033(13)
C6 0.0495(18) 0.0501(17) 0.0594(18) -0.0015(14) 0.0212(15) -0.0044(13)
C7 0.0432(15) 0.0483(17) 0.0620(18) -0.0002(14) 0.0185(14) -0.0023(13)
C8 0.0504(17) 0.0436(17) 0.0645(19) -0.0020(13) 0.0249(15) -0.0014(13)
C9 0.0477(16) 0.0422(16) 0.0617(18) -0.0027(13) 0.0224(15) -0.0048(12)
C10 0.0572(18) 0.0398(16) 0.0680(19) -0.0051(13) 0.0277(16) -0.0033(13)
C11 0.0565(18) 0.0412(17) 0.0655(19) -0.0078(13) 0.0271(16) -0.0069(13)
C12 0.0576(18) 0.0483(18) 0.076(2) -0.0100(15) 0.0351(17) 0.0007(14)
C13 0.0608(19) 0.0364(16) 0.082(2) -0.0047(15) 0.0323(18) 0.0008(13)
C14 0.0499(17) 0.0433(16) 0.0645(19) 0.0018(13) 0.0221(15) -0.0034(13)
C15 0.096(3) 0.138(4) 0.103(3) 0.057(3) 0.051(3) 0.010(3)
C16 0.060(2) 0.100(3) 0.089(3) 0.024(2) 0.024(2) 0.018(2)
C17 0.0471(17) 0.0528(19) 0.071(2) -0.0046(15) 0.0253(16) -0.0025(13)
C18 0.099(3) 0.076(3) 0.103(3) -0.012(2) 0.059(3) 0.012(2)
C19 0.066(2) 0.0470(18) 0.070(2) -0.0073(15) 0.0330(18) -0.0059(15)
C20 0.112(3) 0.089(3) 0.120(3) 0.005(2) 0.084(3) -0.004(2)
C21 0.117(4) 0.133(5) 0.120(4) 0.020(3) 0.042(3) 0.029(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
Cl1 C21 1.717(6) . ?
Cl2 C21 1.605(6) . ?
O1 C3 1.365(4) . ?
O1 C15 1.419(5) . ?
O2 C4 1.376(4) . ?
O2 C16 1.414(4) . ?
O3 C17 1.338(4) . ?
O3 C18 1.440(4) . ?
O4 C17 1.201(4) . ?
O5 C19 1.202(4) . ?
O6 C19 1.324(4) . ?
O6 C20 1.443(4) . ?
N1 C7 1.370(4) . ?
N1 C14 1.373(4) . ?
N1 H1A 0.8600 . ?
C1 C6 1.365(4) . ?
C1 C2 1.379(4) . ?
C1 H1B 0.9300 . ?
C2 C3 1.384(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.396(5) . ?
C4 C5 1.374(4) . ?
C5 C6 1.407(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.477(4) . ?
C7 C8 1.382(4) . ?
C8 C9 1.428(4) . ?
C8 C17 1.467(4) . ?
C9 C10 1.396(4) . ?
C9 C14 1.400(4) . ?
C10 C11 1.394(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.410(4) . ?
C11 C19 1.470(4) . ?
C12 C13 1.367(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.394(4) . ?
C13 H13A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20D 0.9600 . ?
C20 H20B 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 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
C3 O1 C15 117.1(3) . . ?
C4 O2 C16 118.0(3) . . ?
C17 O3 C18 116.6(3) . . ?
C19 O6 C20 115.7(3) . . ?
C7 N1 C14 110.7(2) . . ?
C7 N1 H1A 124.6 . . ?
C14 N1 H1A 124.6 . . ?
C6 C1 C2 121.4(3) . . ?
C6 C1 H1B 119.3 . . ?
C2 C1 H1B 119.3 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
O1 C3 C2 124.9(3) . . ?
O1 C3 C4 115.9(3) . . ?
C2 C3 C4 119.1(3) . . ?
C5 C4 O2 124.4(3) . . ?
C5 C4 C3 120.7(3) . . ?
O2 C4 C3 114.9(3) . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 121.4(3) . . ?
C5 C6 C7 119.2(3) . . ?
N1 C7 C8 107.5(3) . . ?
N1 C7 C6 118.3(3) . . ?
C8 C7 C6 134.2(3) . . ?
C7 C8 C9 107.8(3) . . ?
C7 C8 C17 128.5(3) . . ?
C9 C8 C17 123.5(3) . . ?
C10 C9 C14 118.4(3) . . ?
C10 C9 C8 134.8(3) . . ?
C14 C9 C8 106.8(3) . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 C19 117.2(3) . . ?
C12 C11 C19 122.3(3) . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C12 C13 C14 117.6(3) . . ?
C12 C13 H13A 121.2 . . ?
C14 C13 H13A 121.2 . . ?
N1 C14 C13 129.8(3) . . ?
N1 C14 C9 107.1(3) . . ?
C13 C14 C9 123.1(3) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O3 123.1(3) . . ?
O4 C17 C8 123.7(3) . . ?
O3 C17 C8 113.2(3) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 O6 122.2(3) . . ?
O5 C19 C11 124.3(3) . . ?
O6 C19 C11 113.5(3) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20D 109.5 . . ?
H20A C20 H20D 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20D C20 H20B 109.5 . . ?
Cl2 C21 Cl1 118.7(4) . . ?
Cl2 C21 H21A 107.6 . . ?
Cl1 C21 H21A 107.6 . . ?
Cl2 C21 H21B 107.6 . . ?
Cl1 C21 H21B 107.6 . . ?
H21A C21 H21B 107.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.056