# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010

data_global
_journal_name_full               'New J.Chem.'

_journal_coden_Cambridge         0440
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Vladimir Khodorkovsky'
_publ_contact_author_email       khodor@cinam.univ-mrs.fr

_publ_section_title              
;
Dibenzo[2,3:5,6]pyrrolizino[1,7-bc]indolo
[1,2,3-lm]carbazole: a new electron donor.
;
loop_
_publ_author_name
'Claude Niebel'
'Vladimir Lokshin'
'Amos Ben-Asuly'
'Wladimir Marine'
'Artak Karapetyan'
;
V.Khodorkovsky
;

# Attachment '- CCDC706871.cif'

data_cn288
_database_code_depnum_ccdc_archive 'CCDC 706871'
#TrackingRef '- CCDC706871.cif'

__audit_creation_method          SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H16 N2'
_chemical_formula_weight         404.44

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   'P 21'

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

_cell_length_a                   5.795(5)
_cell_length_b                   15.097(5)
_cell_length_c                   10.982(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 99.368(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     948.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7689
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.97

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  KappacCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1298
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         22.50
_reflns_number_total             1298
_reflns_number_gt                1018
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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^)+(0.1490P)^2^+0.0930P] 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     SHELXL
_refine_ls_extinction_coef       0.011(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         1298
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.2160
_refine_ls_wR_factor_gt          0.1975
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
C1 C 0.1162(18) 0.1741(8) -0.0515(10) 0.051(3) Uani 1 1 d . . .
C2 C 0.1151(16) 0.1969(7) 0.0688(9) 0.045(3) Uani 1 1 d . . .
C3 C 0.2602(16) 0.1774(7) 0.1806(9) 0.045(3) Uani 1 1 d . . .
C4 C 0.4453(14) 0.1199(7) 0.1659(8) 0.038(2) Uani 1 1 d . . .
C5 C 0.4495(17) 0.0956(8) 0.0422(9) 0.049(3) Uani 1 1 d . . .
C6 C 0.3028(15) 0.1175(6) -0.0677(8) 0.034(2) Uani 1 1 d . . .
C7 C -0.0929(18) 0.2184(7) -0.1216(10) 0.052(3) Uani 1 1 d . . .
C8 C -0.1830(15) 0.2220(7) -0.2462(9) 0.049(3) Uani 1 1 d . . .
H8 H -0.1133 0.1917 -0.3044 0.058 Uiso 1 1 calc R . .
C9 C -0.3870(18) 0.2742(10) -0.2810(10) 0.068(4) Uani 1 1 d . . .
H9 H -0.4534 0.2783 -0.3638 0.082 Uiso 1 1 calc R . .
C10 C -0.4879(17) 0.3189(8) -0.1935(11) 0.062(3) Uani 1 1 d . . .
H10 H -0.6216 0.3522 -0.2198 0.075 Uiso 1 1 calc R . .
C11 C -0.4007(16) 0.3167(7) -0.0689(10) 0.052(3) Uani 1 1 d . . .
H11 H -0.4735 0.3471 -0.0120 0.063 Uiso 1 1 calc R . .
C12 C -0.1981(16) 0.2667(8) -0.0318(9) 0.049(3) Uani 1 1 d . . .
C13 C -0.0533(15) 0.2678(7) 0.2134(8) 0.041(3) Uani 1 1 d . . .
C14 C -0.2018(17) 0.3135(7) 0.2723(9) 0.053(3) Uani 1 1 d . . .
H14 H -0.3339 0.3412 0.2294 0.064 Uiso 1 1 calc R . .
C15 C -0.1478(17) 0.3173(7) 0.4013(9) 0.052(3) Uani 1 1 d . . .
H15 H -0.2476 0.3464 0.4463 0.062 Uiso 1 1 calc R . .
C16 C 0.0539(17) 0.2777(7) 0.4617(8) 0.051(3) Uani 1 1 d . . .
H16 H 0.0914 0.2840 0.5469 0.062 Uiso 1 1 calc R . .
C17 C 0.2030(16) 0.2290(8) 0.4005(8) 0.052(3) Uani 1 1 d . . .
H17 H 0.3352 0.2018 0.4440 0.063 Uiso 1 1 calc R . .
C18 C 0.1508(17) 0.2218(7) 0.2741(8) 0.047(3) Uani 1 1 d . . .
C19 C 0.6488(14) 0.0751(7) 0.2338(8) 0.041(2) Uani 1 1 d . . .
C20 C 0.7454(17) 0.0663(7) 0.3549(10) 0.053(3) Uani 1 1 d . . .
H20 H 0.6767 0.0951 0.4148 0.063 Uiso 1 1 calc R . .
C21 C 0.9373(19) 0.0170(7) 0.3896(8) 0.054(3) Uani 1 1 d . . .
H21 H 0.9969 0.0114 0.4731 0.065 Uiso 1 1 calc R . .
C22 C 1.0481(19) -0.0254(9) 0.3043(10) 0.066(3) Uani 1 1 d . . .
H22 H 1.1830 -0.0581 0.3305 0.080 Uiso 1 1 calc R . .
C23 C 0.9588(17) -0.0194(8) 0.1791(9) 0.052(3) Uani 1 1 d . . .
H23 H 1.0314 -0.0472 0.1199 0.062 Uiso 1 1 calc R . .
C24 C 0.7593(16) 0.0292(6) 0.1474(8) 0.036(2) Uani 1 1 d . . .
C25 C 0.6163(16) 0.0255(7) -0.0970(9) 0.039(3) Uani 1 1 d . . .
C26 C 0.7603(18) -0.0236(7) -0.1609(9) 0.053(3) Uani 1 1 d . . .
H26 H 0.8917 -0.0527 -0.1198 0.063 Uiso 1 1 calc R . .
C27 C 0.7011(18) -0.0274(8) -0.2865(11) 0.062(3) Uani 1 1 d . . .
H27 H 0.7979 -0.0585 -0.3312 0.074 Uiso 1 1 calc R . .
C28 C 0.5033(19) 0.0131(8) -0.3500(10) 0.057(3) Uani 1 1 d . . .
H28 H 0.4685 0.0077 -0.4354 0.068 Uiso 1 1 calc R . .
C29 C 0.3558(18) 0.0618(8) -0.2871(10) 0.057(3) Uani 1 1 d . . .
H29 H 0.2226 0.0887 -0.3301 0.068 Uiso 1 1 calc R . .
C30 C 0.4087(17) 0.0697(7) -0.1620(9) 0.043(2) Uani 1 1 d . . .
N1 N -0.0706(13) 0.2513(6) 0.0834(6) 0.045(2) Uani 1 1 d . . .
N2 N 0.6268(15) 0.0456(6) 0.0274(8) 0.055(3) Uani 1 1 d . . .

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
C1 0.047(6) 0.059(8) 0.049(7) -0.012(6) 0.014(5) -0.009(6)
C2 0.045(5) 0.042(7) 0.048(6) -0.004(5) 0.007(5) 0.004(5)
C3 0.048(5) 0.045(7) 0.045(6) 0.003(5) 0.016(4) -0.008(5)
C4 0.033(5) 0.036(6) 0.044(6) 0.005(4) 0.008(4) 0.012(4)
C5 0.043(5) 0.048(8) 0.056(7) 0.000(6) 0.012(5) 0.003(5)
C6 0.033(4) 0.027(6) 0.042(5) 0.001(5) 0.007(4) 0.006(4)
C7 0.058(6) 0.038(7) 0.060(7) -0.007(6) 0.009(5) -0.025(6)
C8 0.044(5) 0.042(7) 0.055(6) 0.012(5) -0.005(4) 0.000(5)
C9 0.054(7) 0.081(10) 0.065(7) -0.013(7) 0.001(6) 0.021(7)
C10 0.047(6) 0.056(8) 0.079(8) 0.009(7) -0.004(6) -0.013(6)
C11 0.043(5) 0.036(6) 0.076(8) 0.004(6) 0.003(5) 0.007(5)
C12 0.049(6) 0.042(7) 0.055(6) -0.013(6) 0.007(5) 0.003(5)
C13 0.041(5) 0.042(7) 0.040(5) -0.002(5) 0.000(4) 0.000(5)
C14 0.049(5) 0.043(7) 0.067(7) -0.003(6) 0.008(5) 0.004(6)
C15 0.059(6) 0.044(7) 0.053(6) -0.006(5) 0.015(5) 0.000(6)
C16 0.064(7) 0.046(7) 0.046(5) -0.015(5) 0.016(5) -0.013(6)
C17 0.052(5) 0.057(8) 0.045(6) 0.000(5) 0.002(4) 0.000(5)
C18 0.056(6) 0.041(6) 0.045(6) 0.000(5) 0.012(4) -0.018(5)
C19 0.034(5) 0.038(6) 0.048(6) 0.011(5) -0.001(4) -0.001(4)
C20 0.056(6) 0.040(7) 0.063(7) 0.001(6) 0.010(5) 0.002(6)
C21 0.077(7) 0.045(7) 0.040(5) 0.011(5) 0.009(5) -0.015(6)
C22 0.061(6) 0.067(9) 0.074(8) 0.007(7) 0.017(6) 0.022(6)
C23 0.056(6) 0.049(7) 0.053(6) 0.004(6) 0.015(5) 0.007(6)
C24 0.045(5) 0.023(6) 0.040(5) 0.004(4) 0.010(4) -0.008(4)
C25 0.045(6) 0.021(6) 0.059(6) 0.006(5) 0.030(5) -0.006(4)
C26 0.060(6) 0.048(7) 0.055(7) 0.003(6) 0.024(5) 0.013(6)
C27 0.048(6) 0.055(8) 0.089(9) -0.015(7) 0.031(6) -0.005(6)
C28 0.065(7) 0.044(8) 0.066(7) 0.002(6) 0.024(6) -0.006(6)
C29 0.056(6) 0.044(7) 0.073(8) 0.001(6) 0.017(5) 0.000(5)
C30 0.053(6) 0.037(6) 0.041(6) -0.006(5) 0.016(4) -0.004(5)
N1 0.044(4) 0.050(6) 0.038(5) -0.005(4) 0.004(4) 0.005(4)
N2 0.060(5) 0.040(6) 0.068(7) 0.000(4) 0.020(5) -0.020(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
C1 C2 1.366(14) . ?
C1 C6 1.411(12) . ?
C1 C7 1.485(16) . ?
C2 N1 1.384(12) . ?
C2 C3 1.402(13) . ?
C3 C4 1.410(12) . ?
C3 C18 1.455(14) . ?
C4 C5 1.411(12) . ?
C4 C19 1.455(12) . ?
C5 N2 1.306(12) . ?
C5 C6 1.397(13) . ?
C6 C30 1.476(13) . ?
C7 C8 1.385(13) . ?
C7 C12 1.439(14) . ?
C8 C9 1.420(15) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(16) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.399(14) . ?
C11 H11 0.9300 . ?
C12 N1 1.377(12) . ?
C13 C14 1.348(13) . ?
C13 N1 1.437(10) . ?
C13 C18 1.438(14) . ?
C14 C15 1.402(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(12) . ?
C17 H17 0.9300 . ?
C19 C20 1.363(13) . ?
C19 C24 1.411(13) . ?
C20 C21 1.341(15) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(15) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(14) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(14) . ?
C23 H23 0.9300 . ?
C24 N2 1.434(12) . ?
C25 C26 1.388(14) . ?
C25 N2 1.392(12) . ?
C25 C30 1.457(14) . ?
C26 C27 1.368(15) . ?
C26 H26 0.9300 . ?
C27 C28 1.383(16) . ?
C27 H27 0.9300 . ?
C28 C29 1.393(15) . ?
C28 H28 0.9300 . ?
C29 C30 1.363(13) . ?
C29 H29 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
C2 C1 C6 113.5(9) . . ?
C2 C1 C7 104.8(9) . . ?
C6 C1 C7 141.7(9) . . ?
C1 C2 N1 112.8(9) . . ?
C1 C2 C3 134.3(10) . . ?
N1 C2 C3 112.9(8) . . ?
C2 C3 C4 112.8(8) . . ?
C2 C3 C18 104.7(9) . . ?
C4 C3 C18 142.4(9) . . ?
C3 C4 C5 113.8(8) . . ?
C3 C4 C19 142.7(8) . . ?
C5 C4 C19 103.5(8) . . ?
N2 C5 C6 114.2(9) . . ?
N2 C5 C4 114.0(9) . . ?
C6 C5 C4 131.8(10) . . ?
C5 C6 C1 113.9(8) . . ?
C5 C6 C30 103.1(8) . . ?
C1 C6 C30 143.0(8) . . ?
C8 C7 C12 121.6(11) . . ?
C8 C7 C1 132.4(11) . . ?
C12 C7 C1 105.9(9) . . ?
C7 C8 C9 116.8(11) . . ?
C7 C8 H8 121.6 . . ?
C9 C8 H8 121.6 . . ?
C10 C9 C8 120.8(11) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 123.4(11) . . ?
C11 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C10 C11 C12 117.1(10) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
N1 C12 C11 131.1(9) . . ?
N1 C12 C7 108.7(9) . . ?
C11 C12 C7 120.2(10) . . ?
C14 C13 N1 128.3(8) . . ?
C14 C13 C18 124.5(8) . . ?
N1 C13 C18 107.2(8) . . ?
C13 C14 C15 116.8(9) . . ?
C13 C14 H14 121.6 . . ?
C15 C14 H14 121.6 . . ?
C16 C15 C14 120.0(9) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 122.8(9) . . ?
C15 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C18 C17 C16 118.5(10) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C13 117.3(10) . . ?
C17 C18 C3 134.3(10) . . ?
C13 C18 C3 108.4(8) . . ?
C20 C19 C24 116.7(9) . . ?
C20 C19 C4 135.7(9) . . ?
C24 C19 C4 107.6(8) . . ?
C21 C20 C19 121.4(9) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 121.5(9) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C23 120.2(10) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 116.8(9) . . ?
C24 C23 H23 121.6 . . ?
C22 C23 H23 121.6 . . ?
C23 C24 C19 123.4(8) . . ?
C23 C24 N2 129.2(9) . . ?
C19 C24 N2 107.4(8) . . ?
C26 C25 N2 132.7(9) . . ?
C26 C25 C30 120.9(9) . . ?
N2 C25 C30 106.4(8) . . ?
C27 C26 C25 117.4(10) . . ?
C27 C26 H26 121.3 . . ?
C25 C26 H26 121.3 . . ?
C26 C27 C28 122.7(10) . . ?
C26 C27 H27 118.6 . . ?
C28 C27 H27 118.6 . . ?
C27 C28 C29 120.6(10) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C30 C29 C28 119.3(11) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C29 C30 C25 119.1(9) . . ?
C29 C30 C6 134.4(10) . . ?
C25 C30 C6 106.5(8) . . ?
C12 N1 C2 107.7(7) . . ?
C12 N1 C13 145.5(9) . . ?
C2 N1 C13 106.8(7) . . ?
C5 N2 C25 109.8(9) . . ?
C5 N2 C24 107.5(8) . . ?
C25 N2 C24 142.7(9) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        22.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.070