# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
#TrackingRef 'mb1107.cif'

_publ_contact_author_name        'Andrew D. Bond'
_publ_contact_author_address     
;
University of Southern Denmark
Department of Physics and Chemistry
Campusvej 55
5230 Odense
Denmark
;

_publ_contact_author_email       adb@chem.sdu.dk
_publ_contact_author_fax         '+45 6615 8780'
_publ_contact_author_phone       '+45 6650 2545'
loop_
_publ_author_name
L.Skov
M.A.Petersen
S.L.Broman
A.D.Bond
M.B.Nielsen

data_mb1107
_database_code_depnum_ccdc_archive 'CCDC 826860'
#TrackingRef 'mb1107.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            5-phenyldihydroazulene
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 N2'
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3107(7)
_cell_length_b                   9.3161(7)
_cell_length_c                   11.1998(11)
_cell_angle_alpha                92.711(4)
_cell_angle_beta                 114.378(3)
_cell_angle_gamma                100.866(3)
_cell_volume                     860.44(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4498
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(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  'Bruker Nonius X8APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9677
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         25.13
_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        25.13
_diffrn_measured_fraction_theta_full 0.956
_reflns_number_total             2938
_reflns_number_gt                2445
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 v2010.1-2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL v.6.12 (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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^)+(0.0466P)^2^+0.1282P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2938
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032

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 0.37292(13) 1.09848(13) 0.01006(11) 0.0338(3) Uani 1 1 d . . .
N2 N 0.54389(15) 0.78388(14) 0.26081(12) 0.0438(3) Uani 1 1 d . . .
C1 C 0.04604(14) 0.65619(14) -0.09336(12) 0.0258(3) Uani 1 1 d . . .
C2 C 0.01317(15) 0.72972(14) 0.00516(13) 0.0290(3) Uani 1 1 d . . .
H2A H -0.0906 0.7103 0.0053 0.035 Uiso 1 1 calc R . .
C3 C 0.14108(14) 0.82797(14) 0.09694(12) 0.0263(3) Uani 1 1 d . . .
C4 C 0.28788(14) 0.83257(13) 0.06381(12) 0.0243(3) Uani 1 1 d . . .
C5 C 0.22371(14) 0.71025(14) -0.06140(12) 0.0252(3) Uani 1 1 d . . .
H5A H 0.2344 0.7567 -0.1369 0.030 Uiso 1 1 calc R . .
C6 C 0.30174(14) 0.58015(14) -0.03935(13) 0.0298(3) Uani 1 1 d . . .
H6A H 0.3874 0.5794 0.0445 0.036 Uiso 1 1 calc R . .
C7 C 0.25400(14) 0.46556(15) -0.13431(14) 0.0313(3) Uani 1 1 d . . .
H7A H 0.3171 0.3934 -0.1149 0.038 Uiso 1 1 calc R . .
C8 C 0.11770(15) 0.43894(14) -0.26286(13) 0.0293(3) Uani 1 1 d . . .
H8A H 0.1306 0.3908 -0.3333 0.035 Uiso 1 1 calc R . .
C9 C -0.02703(14) 0.47528(13) -0.29403(12) 0.0259(3) Uani 1 1 d . . .
C10 C -0.06105(14) 0.55662(14) -0.19863(12) 0.0275(3) Uani 1 1 d . . .
H10A H -0.1708 0.5377 -0.2118 0.033 Uiso 1 1 calc R . .
C11 C 0.33731(13) 0.98208(15) 0.03312(12) 0.0244(3) Uani 1 1 d . . .
C12 C 0.43177(16) 0.80534(14) 0.17626(13) 0.0293(3) Uani 1 1 d . . .
C13 C 0.14818(15) 0.92278(14) 0.20892(12) 0.0267(3) Uani 1 1 d . . .
C14 C 0.00476(15) 0.92717(14) 0.22051(13) 0.0304(3) Uani 1 1 d . . .
H14A H -0.0954 0.8692 0.1556 0.037 Uiso 1 1 calc R . .
C15 C 0.00658(16) 1.01439(15) 0.32477(14) 0.0345(3) Uani 1 1 d . . .
H15A H -0.0921 1.0167 0.3303 0.041 Uiso 1 1 calc R . .
C16 C 0.15176(17) 1.09853(14) 0.42135(14) 0.0340(3) Uani 1 1 d . . .
H16A H 0.1532 1.1570 0.4938 0.041 Uiso 1 1 calc R . .
C17 C 0.29378(17) 1.09640(15) 0.41113(13) 0.0344(3) Uani 1 1 d . . .
H17A H 0.3935 1.1542 0.4766 0.041 Uiso 1 1 calc R . .
C18 C 0.29215(16) 1.01053(14) 0.30606(13) 0.0320(3) Uani 1 1 d . . .
H18A H 0.3911 1.0114 0.3000 0.038 Uiso 1 1 calc R . .
C19 C -0.16369(14) 0.42100(14) -0.42765(13) 0.0264(3) Uani 1 1 d . . .
C20 C -0.18135(15) 0.28721(14) -0.50058(13) 0.0299(3) Uani 1 1 d . . .
H20A H -0.1055 0.2278 -0.4640 0.036 Uiso 1 1 calc R . .
C21 C -0.30780(15) 0.24050(15) -0.62514(13) 0.0326(3) Uani 1 1 d . . .
H21A H -0.3180 0.1494 -0.6731 0.039 Uiso 1 1 calc R . .
C22 C -0.41971(15) 0.32541(15) -0.68052(13) 0.0336(3) Uani 1 1 d . . .
H22A H -0.5053 0.2939 -0.7666 0.040 Uiso 1 1 calc R . .
C23 C -0.40519(15) 0.45670(15) -0.60883(13) 0.0330(3) Uani 1 1 d . . .
H23A H -0.4820 0.5151 -0.6456 0.040 Uiso 1 1 calc R . .
C24 C -0.27958(15) 0.50343(14) -0.48407(13) 0.0298(3) Uani 1 1 d . . .
H24A H -0.2720 0.5934 -0.4358 0.036 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 0.0357(6) 0.0294(7) 0.0346(7) 0.0041(5) 0.0147(5) 0.0046(5)
N2 0.0507(7) 0.0427(8) 0.0300(7) 0.0005(6) 0.0058(6) 0.0207(6)
C1 0.0263(6) 0.0253(7) 0.0264(7) 0.0032(6) 0.0120(5) 0.0055(5)
C2 0.0275(6) 0.0296(8) 0.0319(7) 0.0013(6) 0.0162(6) 0.0038(5)
C3 0.0297(6) 0.0236(7) 0.0275(7) 0.0035(6) 0.0145(5) 0.0049(5)
C4 0.0255(6) 0.0235(7) 0.0218(7) 0.0023(5) 0.0090(5) 0.0040(5)
C5 0.0258(6) 0.0251(7) 0.0234(7) -0.0001(5) 0.0112(5) 0.0020(5)
C6 0.0217(6) 0.0321(8) 0.0337(8) -0.0005(6) 0.0113(5) 0.0047(5)
C7 0.0245(6) 0.0293(7) 0.0406(8) -0.0010(6) 0.0156(6) 0.0049(5)
C8 0.0311(7) 0.0249(7) 0.0336(7) -0.0024(6) 0.0188(6) 0.0005(5)
C9 0.0294(6) 0.0195(7) 0.0294(7) 0.0013(5) 0.0159(6) -0.0004(5)
C10 0.0240(6) 0.0280(7) 0.0307(7) 0.0012(6) 0.0129(5) 0.0039(5)
C11 0.0206(6) 0.0290(8) 0.0218(7) 0.0003(6) 0.0078(5) 0.0051(5)
C12 0.0356(7) 0.0256(7) 0.0261(7) 0.0003(6) 0.0127(6) 0.0076(6)
C13 0.0345(7) 0.0222(7) 0.0262(7) 0.0047(6) 0.0160(6) 0.0057(5)
C14 0.0327(7) 0.0279(7) 0.0306(8) 0.0033(6) 0.0129(6) 0.0085(6)
C15 0.0396(7) 0.0328(8) 0.0405(8) 0.0066(7) 0.0235(7) 0.0149(6)
C16 0.0501(8) 0.0248(7) 0.0341(8) 0.0010(6) 0.0251(7) 0.0089(6)
C17 0.0417(7) 0.0280(8) 0.0308(8) -0.0030(6) 0.0172(6) -0.0001(6)
C18 0.0343(7) 0.0284(8) 0.0344(8) -0.0012(6) 0.0190(6) 0.0011(6)
C19 0.0288(6) 0.0229(7) 0.0291(7) 0.0013(6) 0.0167(6) 0.0002(5)
C20 0.0321(7) 0.0257(7) 0.0322(8) 0.0014(6) 0.0154(6) 0.0043(5)
C21 0.0359(7) 0.0275(7) 0.0329(8) -0.0047(6) 0.0175(6) -0.0005(6)
C22 0.0315(7) 0.0362(8) 0.0274(7) 0.0006(6) 0.0118(6) -0.0021(6)
C23 0.0313(7) 0.0312(8) 0.0356(8) 0.0065(6) 0.0142(6) 0.0047(6)
C24 0.0339(7) 0.0225(7) 0.0329(8) 0.0001(6) 0.0167(6) 0.0020(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 C11 1.1463(16) . ?
N2 C12 1.1432(16) . ?
C1 C10 1.3498(18) . ?
C1 C2 1.4375(18) . ?
C1 C5 1.5160(16) . ?
C2 C3 1.3425(17) . ?
C2 H2A 0.9500 . ?
C3 C13 1.4704(18) . ?
C3 C4 1.5510(17) . ?
C4 C11 1.4846(18) . ?
C4 C12 1.4869(18) . ?
C4 C5 1.5883(17) . ?
C5 C6 1.5066(18) . ?
C5 H5A 1.0000 . ?
C6 C7 1.3386(18) . ?
C6 H6A 0.9500 . ?
C7 C8 1.4436(18) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3591(17) . ?
C8 H8A 0.9500 . ?
C9 C10 1.4524(18) . ?
C9 C19 1.4927(17) . ?
C10 H10A 0.9500 . ?
C13 C18 1.3956(18) . ?
C13 C14 1.4017(18) . ?
C14 C15 1.3831(18) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3874(19) . ?
C15 H15A 0.9500 . ?
C16 C17 1.3772(19) . ?
C16 H16A 0.9500 . ?
C17 C18 1.3845(19) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C24 1.3959(18) . ?
C19 C20 1.4012(18) . ?
C20 C21 1.3840(18) . ?
C20 H20A 0.9500 . ?
C21 C22 1.3856(19) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3835(19) . ?
C22 H22A 0.9500 . ?
C23 C24 1.3824(18) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?

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
C10 C1 C2 126.87(11) . . ?
C10 C1 C5 124.48(11) . . ?
C2 C1 C5 108.65(10) . . ?
C3 C2 C1 114.56(11) . . ?
C3 C2 H2A 122.7 . . ?
C1 C2 H2A 122.7 . . ?
C2 C3 C13 128.35(11) . . ?
C2 C3 C4 108.38(11) . . ?
C13 C3 C4 123.23(10) . . ?
C11 C4 C12 106.74(10) . . ?
C11 C4 C3 108.83(10) . . ?
C12 C4 C3 112.84(10) . . ?
C11 C4 C5 111.63(10) . . ?
C12 C4 C5 111.91(10) . . ?
C3 C4 C5 104.95(9) . . ?
C6 C5 C1 108.57(10) . . ?
C6 C5 C4 115.62(10) . . ?
C1 C5 C4 103.30(9) . . ?
C6 C5 H5A 109.7 . . ?
C1 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C7 C6 C5 122.00(12) . . ?
C7 C6 H6A 119.0 . . ?
C5 C6 H6A 119.0 . . ?
C6 C7 C8 127.54(12) . . ?
C6 C7 H7A 116.2 . . ?
C8 C7 H7A 116.2 . . ?
C9 C8 C7 127.05(12) . . ?
C9 C8 H8A 116.5 . . ?
C7 C8 H8A 116.5 . . ?
C8 C9 C10 122.72(11) . . ?
C8 C9 C19 120.14(12) . . ?
C10 C9 C19 116.96(10) . . ?
C1 C10 C9 127.19(11) . . ?
C1 C10 H10A 116.4 . . ?
C9 C10 H10A 116.4 . . ?
N1 C11 C4 178.49(13) . . ?
N2 C12 C4 178.46(14) . . ?
C18 C13 C14 117.37(12) . . ?
C18 C13 C3 123.21(11) . . ?
C14 C13 C3 119.42(11) . . ?
C15 C14 C13 121.12(12) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C14 C15 C16 120.35(12) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C17 C16 C15 119.35(12) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
C16 C17 C18 120.44(12) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C17 C18 C13 121.36(12) . . ?
C17 C18 H18A 119.3 . . ?
C13 C18 H18A 119.3 . . ?
C24 C19 C20 117.65(12) . . ?
C24 C19 C9 120.34(11) . . ?
C20 C19 C9 122.02(11) . . ?
C21 C20 C19 120.86(12) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C20 C21 C22 120.59(13) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C23 C22 C21 119.18(12) . . ?
C23 C22 H22A 120.4 . . ?
C21 C22 H22A 120.4 . . ?
C24 C23 C22 120.43(13) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C23 C24 C19 121.27(12) . . ?
C23 C24 H24A 119.4 . . ?
C19 C24 H24A 119.4 . . ?

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
C10 C1 C2 C3 -177.69(13) . . . . ?
C5 C1 C2 C3 1.57(16) . . . . ?
C1 C2 C3 C13 178.90(11) . . . . ?
C1 C2 C3 C4 1.15(16) . . . . ?
C2 C3 C4 C11 116.39(12) . . . . ?
C13 C3 C4 C11 -61.50(14) . . . . ?
C2 C3 C4 C12 -125.34(12) . . . . ?
C13 C3 C4 C12 56.77(15) . . . . ?
C2 C3 C4 C5 -3.23(13) . . . . ?
C13 C3 C4 C5 178.88(11) . . . . ?
C10 C1 C5 C6 -60.89(16) . . . . ?
C2 C1 C5 C6 119.83(11) . . . . ?
C10 C1 C5 C4 175.87(12) . . . . ?
C2 C1 C5 C4 -3.41(13) . . . . ?
C11 C4 C5 C6 127.74(11) . . . . ?
C12 C4 C5 C6 8.18(15) . . . . ?
C3 C4 C5 C6 -114.53(11) . . . . ?
C11 C4 C5 C1 -113.82(11) . . . . ?
C12 C4 C5 C1 126.62(11) . . . . ?
C3 C4 C5 C1 3.91(12) . . . . ?
C1 C5 C6 C7 61.20(16) . . . . ?
C4 C5 C6 C7 176.68(11) . . . . ?
C5 C6 C7 C8 -6.3(2) . . . . ?
C6 C7 C8 C9 -33.7(2) . . . . ?
C7 C8 C9 C10 3.6(2) . . . . ?
C7 C8 C9 C19 -171.32(12) . . . . ?
C2 C1 C10 C9 -175.98(12) . . . . ?
C5 C1 C10 C9 4.9(2) . . . . ?
C8 C9 C10 C1 29.3(2) . . . . ?
C19 C9 C10 C1 -155.66(13) . . . . ?
C2 C3 C13 C18 173.39(13) . . . . ?
C4 C3 C13 C18 -9.16(19) . . . . ?
C2 C3 C13 C14 -6.7(2) . . . . ?
C4 C3 C13 C14 170.72(11) . . . . ?
C18 C13 C14 C15 -0.44(19) . . . . ?
C3 C13 C14 C15 179.67(11) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C15 C16 C17 1.2(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C13 -0.8(2) . . . . ?
C14 C13 C18 C17 1.20(19) . . . . ?
C3 C13 C18 C17 -178.91(12) . . . . ?
C8 C9 C19 C24 -150.56(12) . . . . ?
C10 C9 C19 C24 34.21(16) . . . . ?
C8 C9 C19 C20 29.63(18) . . . . ?
C10 C9 C19 C20 -145.59(12) . . . . ?
C24 C19 C20 C21 1.19(18) . . . . ?
C9 C19 C20 C21 -178.99(11) . . . . ?
C19 C20 C21 C22 0.09(19) . . . . ?
C20 C21 C22 C23 -1.05(19) . . . . ?
C21 C22 C23 C24 0.70(19) . . . . ?
C22 C23 C24 C19 0.62(19) . . . . ?
C20 C19 C24 C23 -1.55(18) . . . . ?
C9 C19 C24 C23 178.63(11) . . . . ?