# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5,11-dimethyl-indolo[3,2-b]carbazole

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2'
_chemical_formula_sum            'C20 H16 N2'
_chemical_formula_weight         284.35

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   16.8377(13)
_cell_length_b                   5.6889(4)
_cell_length_c                   15.3882(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.671(2)
_cell_angle_gamma                90.00
_cell_volume                     1412.05(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7126
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      25.06

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6667
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         "high brilliance Incoatec Microfocus Source'"
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8984
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.07
_reflns_number_total             1259
_reflns_number_gt                1201
_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)+(0.0533P)²+1.5552P] 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     SHELXL
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1259
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
N1 N 0.26808(7) -0.13495(19) 0.11193(7) 0.0191(3) Uani 1 1 d . . .
C1 C 0.08617(9) -0.2818(3) 0.19078(9) 0.0242(4) Uani 1 1 d . . .
H1 H 0.0655 -0.3928 0.2251 0.029 Uiso 1 1 calc R . .
C2 C 0.16558(9) -0.3100(2) 0.18306(9) 0.0220(4) Uani 1 1 d . . .
H2 H 0.1998 -0.4370 0.2117 0.026 Uiso 1 1 calc R . .
C3 C 0.19333(8) -0.1447(2) 0.13165(8) 0.0188(3) Uani 1 1 d . . .
C4 C 0.26760(8) 0.0569(2) 0.05595(8) 0.0174(3) Uani 1 1 d . . .
C5 C 0.32830(8) 0.1284(2) 0.01674(8) 0.0183(3) Uani 1 1 d . . .
H5 H 0.3797 0.0480 0.0279 0.022 Uiso 1 1 calc R . .
C6 C 0.19015(8) 0.1753(2) 0.04000(8) 0.0175(3) Uani 1 1 d . . .
C7 C 0.14304(8) 0.0459(2) 0.08913(8) 0.0181(3) Uani 1 1 d . . .
C8 C 0.06365(8) 0.0705(2) 0.09894(9) 0.0206(3) Uani 1 1 d . . .
H8 H 0.0294 0.1985 0.0714 0.025 Uiso 1 1 calc R . .
C9 C 0.03550(9) -0.0943(3) 0.14940(9) 0.0231(4) Uani 1 1 d . . .
H9 H -0.0187 -0.0800 0.1560 0.028 Uiso 1 1 calc R . .
C10 C 0.33618(8) -0.2977(2) 0.14538(9) 0.0227(4) Uani 1 1 d . . .
H10 H 0.3148 -0.4589 0.1396 0.034 Uiso 1 1 calc R . .
H10A H 0.3641 -0.2638 0.2093 0.034 Uiso 1 1 calc R . .
H10B H 0.3757 -0.2805 0.1099 0.034 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
N1 0.0193(6) 0.0180(6) 0.0198(6) 0.0015(4) 0.0053(4) 0.0035(4)
C1 0.0267(7) 0.0245(8) 0.0231(7) 0.0012(6) 0.0097(6) -0.0018(6)
C2 0.0260(7) 0.0198(7) 0.0199(7) 0.0009(5) 0.0063(5) 0.0025(5)
C3 0.0209(7) 0.0194(7) 0.0156(6) -0.0033(5) 0.0046(5) 0.0005(5)
C4 0.0194(7) 0.0166(7) 0.0149(6) -0.0022(5) 0.0029(5) 0.0018(5)
C5 0.0177(6) 0.0186(7) 0.0176(6) -0.0024(5) 0.0034(5) 0.0026(5)
C6 0.0173(7) 0.0186(7) 0.0157(6) -0.0032(5) 0.0035(5) 0.0011(5)
C7 0.0208(7) 0.0176(7) 0.0148(6) -0.0032(5) 0.0033(5) 0.0000(5)
C8 0.0210(7) 0.0221(7) 0.0177(7) -0.0020(5) 0.0038(5) 0.0021(5)
C9 0.0213(7) 0.0271(7) 0.0221(7) -0.0018(6) 0.0079(5) 0.0001(6)
C10 0.0227(7) 0.0206(7) 0.0236(7) 0.0022(5) 0.0050(5) 0.0054(5)

_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 C3 1.3778(17) . ?
N1 C4 1.3888(17) . ?
N1 C10 1.4486(17) . ?
C1 C2 1.385(2) . ?
C1 C9 1.400(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.3931(19) . ?
C2 H2 0.9500 . ?
C3 C7 1.4152(18) . ?
C4 C5 1.3886(18) . ?
C4 C6 1.4251(18) . ?
C5 C6 1.3966(18) 7 ?
C5 H5 0.9500 . ?
C6 C5 1.3966(18) 7 ?
C6 C7 1.4444(19) . ?
C7 C8 1.3946(18) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?

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 N1 C4 108.97(10) . . ?
C3 N1 C10 125.16(11) . . ?
C4 N1 C10 125.87(11) . . ?
C2 C1 C9 121.76(13) . . ?
C2 C1 H1 119.1 . . ?
C9 C1 H1 119.1 . . ?
C1 C2 C3 117.39(13) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
N1 C3 C2 128.95(12) . . ?
N1 C3 C7 109.31(12) . . ?
C2 C3 C7 121.73(13) . . ?
C5 C4 N1 128.74(12) . . ?
C5 C4 C6 122.54(12) . . ?
N1 C4 C6 108.69(11) . . ?
C4 C5 C6 116.53(12) . 7 ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 7 . ?
C5 C6 C4 120.93(12) 7 . ?
C5 C6 C7 132.66(12) 7 . ?
C4 C6 C7 106.37(11) . . ?
C8 C7 C3 119.46(12) . . ?
C8 C7 C6 133.85(12) . . ?
C3 C7 C6 106.66(12) . . ?
C9 C8 C7 119.05(13) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C1 120.60(13) . . ?
C8 C9 H9 119.7 . . ?
C1 C9 H9 119.7 . . ?
N1 C10 H10 109.5 . . ?
N1 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 -0.5(2) . . . . ?
C4 N1 C3 C2 178.11(13) . . . . ?
C10 N1 C3 C2 -2.6(2) . . . . ?
C4 N1 C3 C7 -0.88(14) . . . . ?
C10 N1 C3 C7 178.45(11) . . . . ?
C1 C2 C3 N1 -178.54(12) . . . . ?
C1 C2 C3 C7 0.34(19) . . . . ?
C3 N1 C4 C5 -177.29(12) . . . . ?
C10 N1 C4 C5 3.4(2) . . . . ?
C3 N1 C4 C6 0.56(14) . . . . ?
C10 N1 C4 C6 -178.76(11) . . . . ?
N1 C4 C5 C6 177.56(12) . . . 7 ?
C6 C4 C5 C6 0.0(2) . . . 7 ?
C5 C4 C6 C5 0.0(2) . . . 7 ?
N1 C4 C6 C5 -177.99(11) . . . 7 ?
C5 C4 C6 C7 177.98(11) . . . . ?
N1 C4 C6 C7 -0.04(14) . . . . ?
N1 C3 C7 C8 179.34(11) . . . . ?
C2 C3 C7 C8 0.26(19) . . . . ?
N1 C3 C7 C6 0.85(14) . . . . ?
C2 C3 C7 C6 -178.24(12) . . . . ?
C5 C6 C7 C8 -1.1(2) 7 . . . ?
C4 C6 C7 C8 -178.67(14) . . . . ?
C5 C6 C7 C3 177.12(13) 7 . . . ?
C4 C6 C7 C3 -0.49(14) . . . . ?
C3 C7 C8 C9 -0.74(19) . . . . ?
C6 C7 C8 C9 177.26(13) . . . . ?
C7 C8 C9 C1 0.6(2) . . . . ?
C2 C1 C9 C8 0.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 1017245'
