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


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Heikki Tuononen'
_publ_contact_author_email       heikki.m.tuononen@jyu.fi
loop_
_publ_author_name
'Jani Moilanen'
'Javier Borau-Garcia'
'Roland Roesler'
'Heikki Tuononen'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 868803'
#TrackingRef '- CCDC-86833.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 Al N4'
_chemical_formula_sum            'C23 H21 Al N4'
_chemical_formula_weight         380.42

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'
Al Al 0.0645 0.0514 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.3810(9)
_cell_length_b                   9.4130(4)
_cell_length_c                   15.6040(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.540(2)
_cell_angle_gamma                90.00
_cell_volume                     1965.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5851
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      24.99

_exptl_crystal_description       Rhombohedral
_exptl_crystal_colour            Red-orange
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_process_details   'SORTAV: (Blessing, 1997)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Nonius KappaCCD'
_diffrn_measurement_method       ' \w and \f '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5851
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3399
_reflns_number_gt                2515
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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^)+(0.0000P)^2^+5.8443P] 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         3399
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1354
_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
C23 C 0.2198(3) 0.9061(4) 0.9705(3) 0.0379(10) Uani 1 1 d . . .
H23A H 0.2027 0.8404 1.0168 0.057 Uiso 0.50 1 calc PR . .
H23C H 0.1644 0.9726 0.9610 0.057 Uiso 0.50 1 calc PR . .
H23E H 0.2802 0.9592 0.9863 0.057 Uiso 0.50 1 calc PR . .
H23D H 0.2288 1.0077 0.9593 0.057 Uiso 0.50 1 calc PR . .
H23F H 0.2671 0.8756 1.0151 0.057 Uiso 0.50 1 calc PR . .
H23B H 0.1513 0.8889 0.9897 0.057 Uiso 0.50 1 calc PR . .
C2 C 0.3205(4) 0.3805(5) 0.8094(3) 0.0493(12) Uani 1 1 d . . .
H2 H 0.3760 0.3361 0.7829 0.059 Uiso 1 1 calc R . .
C3 C 0.2440(4) 0.2994(5) 0.8478(3) 0.0565(14) Uani 1 1 d . . .
H3 H 0.2490 0.1988 0.8496 0.068 Uiso 1 1 calc R . .
C4 C 0.1643(4) 0.3646(5) 0.8818(3) 0.0510(13) Uani 1 1 d . . .
H4 H 0.1141 0.3096 0.9089 0.061 Uiso 1 1 calc R . .
C5 C 0.1540(3) 0.5175(4) 0.8776(2) 0.0369(10) Uani 1 1 d . . .
C6 C 0.0643(3) 0.5820(5) 0.8987(3) 0.0438(11) Uani 1 1 d . . .
C7 C 0.0311(3) 0.7191(5) 0.8740(3) 0.0397(10) Uani 1 1 d . . .
C8 C -0.0707(3) 0.7565(6) 0.8835(3) 0.0566(14) Uani 1 1 d . . .
H8 H -0.1155 0.6910 0.9090 0.068 Uiso 1 1 calc R . .
C9 C -0.1049(4) 0.8847(7) 0.8565(3) 0.0678(17) Uani 1 1 d . . .
H9 H -0.1733 0.9088 0.8632 0.081 Uiso 1 1 calc R . .
C10 C -0.0390(4) 0.9811(6) 0.8188(3) 0.0605(15) Uani 1 1 d . . .
H10 H -0.0614 1.0713 0.7991 0.073 Uiso 1 1 calc R . .
C11 C 0.0574(3) 0.9414(5) 0.8114(3) 0.0444(11) Uani 1 1 d . . .
H11 H 0.1024 1.0067 0.7860 0.053 Uiso 1 1 calc R . .
C12 C 0.2215(3) 0.8447(4) 0.6836(2) 0.0332(9) Uani 1 1 d . . .
H12 H 0.1750 0.7687 0.6877 0.040 Uiso 1 1 calc R . .
C13 C 0.2250(3) 0.9174(4) 0.6090(2) 0.0364(10) Uani 1 1 d . . .
H13 H 0.1834 0.8922 0.5617 0.044 Uiso 1 1 calc R . .
C14 C 0.2929(3) 1.0324(4) 0.6037(3) 0.0362(10) Uani 1 1 d . . .
H14 H 0.2937 1.0909 0.5542 0.043 Uiso 1 1 calc R . .
C15 C 0.3560(3) 1.0582(4) 0.6691(2) 0.0324(9) Uani 1 1 d . . .
H15 H 0.4017 1.1351 0.6649 0.039 Uiso 1 1 calc R . .
C16 C 0.3563(3) 0.9727(4) 0.7452(2) 0.0305(9) Uani 1 1 d . . .
C17 C 0.4319(3) 0.9876(4) 0.8065(3) 0.0325(9) Uani 1 1 d . . .
C18 C 0.4565(3) 0.8943(4) 0.8734(2) 0.0283(9) Uani 1 1 d . . .
C19 C 0.5484(3) 0.9088(4) 0.9190(3) 0.0345(10) Uani 1 1 d . . .
H19 H 0.5937 0.9821 0.9038 0.041 Uiso 1 1 calc R . .
C20 C 0.5721(3) 0.8182(5) 0.9846(3) 0.0413(11) Uani 1 1 d . . .
H20 H 0.6331 0.8296 1.0156 0.050 Uiso 1 1 calc R . .
C21 C 0.5068(3) 0.7094(5) 1.0058(3) 0.0400(10) Uani 1 1 d . . .
H21 H 0.5218 0.6455 1.0513 0.048 Uiso 1 1 calc R . .
C22 C 0.4208(3) 0.6973(4) 0.9597(3) 0.0363(9) Uani 1 1 d . . .
H22 H 0.3770 0.6213 0.9733 0.044 Uiso 1 1 calc R . .
C1 C 0.3116(3) 0.5226(4) 0.8117(3) 0.0390(10) Uani 1 1 d . . .
H1 H 0.3634 0.5771 0.7866 0.047 Uiso 1 1 calc R . .
Al1 Al 0.24414(8) 0.79759(12) 0.86426(7) 0.0285(3) Uani 1 1 d . . .
N1 N 0.2337(2) 0.5945(3) 0.8475(2) 0.0314(8) Uani 1 1 d . . .
N2 N 0.0946(2) 0.8143(4) 0.8379(2) 0.0342(8) Uani 1 1 d . . .
N3 N 0.2806(2) 0.8734(3) 0.7539(2) 0.0291(7) Uani 1 1 d . . .
N4 N 0.3930(2) 0.7861(3) 0.8953(2) 0.0312(8) Uani 1 1 d . . .
H17 H 0.479(3) 1.058(4) 0.794(2) 0.035(11) Uiso 1 1 d . . .
H6 H 0.019(4) 0.519(5) 0.922(3) 0.066(15) Uiso 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
C23 0.034(2) 0.039(2) 0.041(2) -0.010(2) -0.0029(19) 0.0001(19)
C2 0.056(3) 0.039(3) 0.052(3) -0.010(2) -0.017(2) 0.012(2)
C3 0.091(4) 0.030(2) 0.048(3) 0.000(2) -0.026(3) -0.001(3)
C4 0.075(4) 0.039(3) 0.038(3) 0.007(2) -0.012(2) -0.022(3)
C5 0.045(3) 0.041(2) 0.024(2) 0.0033(18) -0.0039(18) -0.013(2)
C6 0.046(3) 0.053(3) 0.032(2) -0.001(2) 0.004(2) -0.022(2)
C7 0.032(2) 0.062(3) 0.025(2) -0.007(2) -0.0001(17) -0.011(2)
C8 0.025(2) 0.092(4) 0.053(3) -0.021(3) 0.004(2) -0.007(3)
C9 0.033(3) 0.120(5) 0.051(3) -0.032(3) -0.006(2) 0.020(3)
C10 0.053(3) 0.086(4) 0.042(3) -0.007(3) -0.006(2) 0.032(3)
C11 0.042(2) 0.055(3) 0.036(2) -0.002(2) -0.002(2) 0.019(2)
C12 0.034(2) 0.033(2) 0.033(2) -0.0021(18) -0.0004(18) -0.0030(18)
C13 0.040(2) 0.042(2) 0.027(2) -0.0047(19) -0.0016(18) -0.002(2)
C14 0.043(2) 0.036(2) 0.030(2) 0.0043(18) 0.0077(19) 0.0034(19)
C15 0.039(2) 0.026(2) 0.033(2) 0.0013(17) 0.0018(18) -0.0034(18)
C16 0.027(2) 0.029(2) 0.036(2) -0.0039(18) 0.0055(17) 0.0029(17)
C17 0.030(2) 0.028(2) 0.040(2) 0.0016(18) 0.0019(18) -0.0045(18)
C18 0.027(2) 0.0268(19) 0.031(2) -0.0093(17) 0.0032(16) 0.0015(16)
C19 0.025(2) 0.035(2) 0.043(2) -0.013(2) 0.0012(18) -0.0011(17)
C20 0.035(2) 0.043(2) 0.047(3) -0.016(2) -0.010(2) 0.009(2)
C21 0.042(2) 0.041(2) 0.037(2) -0.002(2) -0.0085(19) 0.013(2)
C22 0.041(2) 0.034(2) 0.033(2) 0.0028(19) 0.0003(18) -0.0018(19)
C1 0.041(2) 0.036(2) 0.040(2) -0.003(2) -0.004(2) 0.003(2)
Al1 0.0271(6) 0.0282(6) 0.0303(6) 0.0012(5) 0.0010(5) -0.0004(5)
N1 0.0311(18) 0.0272(17) 0.0359(19) -0.0003(15) -0.0046(15) -0.0020(14)
N2 0.0298(18) 0.044(2) 0.0282(18) 0.0008(16) -0.0020(14) 0.0020(16)
N3 0.0302(17) 0.0285(17) 0.0287(17) 0.0008(14) 0.0004(14) -0.0042(14)
N4 0.0299(17) 0.0308(18) 0.0329(18) -0.0006(15) 0.0017(14) 0.0014(14)

_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
C23 Al1 1.977(4) . ?
C23 H23A 0.9800 . ?
C23 H23C 0.9800 . ?
C23 H23E 0.9800 . ?
C23 H23D 0.9800 . ?
C23 H23F 0.9800 . ?
C23 H23B 0.9800 . ?
C2 C1 1.343(6) . ?
C2 C3 1.414(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.344(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.447(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.376(5) . ?
C5 C6 1.388(6) . ?
C6 C7 1.417(6) . ?
C6 H6 0.92(5) . ?
C7 N2 1.361(5) . ?
C7 C8 1.416(6) . ?
C8 C9 1.356(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.350(6) . ?
C10 H10 0.9500 . ?
C11 N2 1.358(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.352(5) . ?
C12 N3 1.373(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.416(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.340(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.435(5) . ?
C15 H15 0.9500 . ?
C16 N3 1.385(5) . ?
C16 C17 1.393(5) . ?
C17 C18 1.401(5) . ?
C17 H17 0.94(4) . ?
C18 N4 1.372(5) . ?
C18 C19 1.422(5) . ?
C19 C20 1.368(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.357(6) . ?
C21 H21 0.9500 . ?
C22 N4 1.355(5) . ?
C22 H22 0.9500 . ?
C1 N1 1.367(5) . ?
C1 H1 0.9500 . ?
Al1 N3 1.932(3) . ?
Al1 N1 1.934(3) . ?
Al1 N2 2.045(3) . ?
Al1 N4 2.049(3) . ?

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
Al1 C23 H23A 109.5 . . ?
Al1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
Al1 C23 H23E 109.5 . . ?
H23A C23 H23E 109.5 . . ?
H23C C23 H23E 109.5 . . ?
Al1 C23 H23D 109.5 . . ?
H23A C23 H23D 141.1 . . ?
H23C C23 H23D 56.3 . . ?
H23E C23 H23D 56.3 . . ?
Al1 C23 H23F 109.5 . . ?
H23A C23 H23F 56.3 . . ?
H23C C23 H23F 141.1 . . ?
H23E C23 H23F 56.3 . . ?
H23D C23 H23F 109.5 . . ?
Al1 C23 H23B 109.5 . . ?
H23A C23 H23B 56.3 . . ?
H23C C23 H23B 56.3 . . ?
H23E C23 H23B 141.1 . . ?
H23D C23 H23B 109.5 . . ?
H23F C23 H23B 109.5 . . ?
C1 C2 C3 117.5(5) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C6 121.7(4) . . ?
N1 C5 C4 117.8(4) . . ?
C6 C5 C4 120.4(4) . . ?
C5 C6 C7 127.1(4) . . ?
C5 C6 H6 113(3) . . ?
C7 C6 H6 119(3) . . ?
N2 C7 C8 119.0(4) . . ?
N2 C7 C6 121.1(4) . . ?
C8 C7 C6 119.8(4) . . ?
C9 C8 C7 120.7(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 117.5(5) . . ?
C11 C10 H10 121.2 . . ?
C9 C10 H10 121.2 . . ?
C10 C11 N2 124.5(5) . . ?
C10 C11 H11 117.8 . . ?
N2 C11 H11 117.8 . . ?
C13 C12 N3 124.3(4) . . ?
C13 C12 H12 117.8 . . ?
N3 C12 H12 117.8 . . ?
C12 C13 C14 117.6(4) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C15 C14 C13 119.7(4) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.6(4) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
N3 C16 C17 121.8(4) . . ?
N3 C16 C15 117.6(3) . . ?
C17 C16 C15 120.5(4) . . ?
C16 C17 C18 127.8(4) . . ?
C16 C17 H17 114(2) . . ?
C18 C17 H17 117(2) . . ?
N4 C18 C17 120.6(3) . . ?
N4 C18 C19 118.8(4) . . ?
C17 C18 C19 120.6(4) . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.8(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 117.9(4) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?
N4 C22 C21 124.5(4) . . ?
N4 C22 H22 117.8 . . ?
C21 C22 H22 117.8 . . ?
C2 C1 N1 124.9(4) . . ?
C2 C1 H1 117.6 . . ?
N1 C1 H1 117.6 . . ?
N3 Al1 N1 105.25(15) . . ?
N3 Al1 C23 127.01(17) . . ?
N1 Al1 C23 127.72(17) . . ?
N3 Al1 N2 92.70(14) . . ?
N1 Al1 N2 88.84(14) . . ?
C23 Al1 N2 87.72(15) . . ?
N3 Al1 N4 88.70(13) . . ?
N1 Al1 N4 92.76(14) . . ?
C23 Al1 N4 89.81(15) . . ?
N2 Al1 N4 177.53(14) . . ?
C1 N1 C5 118.4(3) . . ?
C1 N1 Al1 119.4(3) . . ?
C5 N1 Al1 122.0(3) . . ?
C11 N2 C7 118.5(4) . . ?
C11 N2 Al1 118.9(3) . . ?
C7 N2 Al1 118.7(3) . . ?
C12 N3 C16 118.1(3) . . ?
C12 N3 Al1 119.4(3) . . ?
C16 N3 Al1 121.8(3) . . ?
C22 N4 C18 118.5(3) . . ?
C22 N4 Al1 117.8(3) . . ?
C18 N4 Al1 120.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.063