# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012


data_global
_journal_name_full               'New J.Chem.'
_journal_coden_cambridge         0440
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Stefan Spange'
_publ_contact_author_email       stefan.spange@chemie.tu-chemnitz.de
loop_
_publ_author_name
S.Seifert
A.Seifert
G.Brunklaus
K.Hofmann
T.Rueffer
H.Lang
S.Spange

data_wolf2
_database_code_depnum_ccdc_archive 'CCDC 822677'
#TrackingRef '- wolf2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N3 O3'
_chemical_formula_sum            'C15 H15 N3 O3'
_chemical_formula_weight         285.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   4.5663(2)
_cell_length_b                   9.6254(5)
_cell_length_c                   30.3857(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.668(5)
_cell_angle_gamma                90.00
_cell_volume                     1334.96(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    105
_cell_measurement_reflns_used    4606
_cell_measurement_theta_min      4.3913
_cell_measurement_theta_max      65.3303

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_T_min  0.58009
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      105
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  5
_diffrn_standards_decay_%        0

_diffrn_reflns_number            8822
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.82
_diffrn_reflns_theta_max         65.53
_reflns_number_total             2277
_reflns_number_gt                1713
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_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^)+(0.1211P)^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         2277
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1460
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.004
_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
C1 C -0.4751(5) 0.2454(3) 0.13760(7) 0.0473(6) Uani 1 1 d . . .
H1A H -0.5323 0.2527 0.1070 0.071 Uiso 1 1 calc R . .
H1B H -0.3845 0.3306 0.1472 0.071 Uiso 1 1 calc R . .
H1C H -0.6451 0.2281 0.1546 0.071 Uiso 1 1 calc R . .
C2 C -0.1758(5) 0.0579(3) 0.10445(7) 0.0500(6) Uani 1 1 d . . .
H2A H -0.2775 0.0941 0.0788 0.075 Uiso 1 1 calc R . .
H2B H -0.2195 -0.0392 0.1074 0.075 Uiso 1 1 calc R . .
H2C H 0.0313 0.0698 0.1014 0.075 Uiso 1 1 calc R . .
C3 C -0.1568(5) 0.0988(2) 0.18391(6) 0.0389(5) Uani 1 1 d . . .
C4 C -0.2387(5) 0.1735(2) 0.22205(7) 0.0399(5) Uani 1 1 d . . .
H4 H -0.3813 0.2423 0.2195 0.048 Uiso 1 1 calc R . .
C5 C -0.1106(4) 0.1458(2) 0.26248(7) 0.0389(5) Uani 1 1 d . . .
H5 H -0.1675 0.1968 0.2868 0.047 Uiso 1 1 calc R . .
C6 C 0.1039(5) 0.0424(2) 0.26816(7) 0.0388(5) Uani 1 1 d . . .
C7 C 0.1729(5) -0.0359(2) 0.23068(7) 0.0418(5) Uani 1 1 d . . .
H7 H 0.3080 -0.1078 0.2337 0.050 Uiso 1 1 calc R . .
C8 C 0.0480(5) -0.0100(2) 0.18987(7) 0.0413(5) Uani 1 1 d . . .
H8 H 0.0985 -0.0645 0.1660 0.050 Uiso 1 1 calc R . .
C9 C 0.2600(5) 0.0175(2) 0.30895(7) 0.0409(5) Uani 1 1 d . . .
H9 H 0.3856 -0.0586 0.3095 0.049 Uiso 1 1 calc R . .
C10 C 0.2473(5) 0.0918(2) 0.34724(7) 0.0411(5) Uani 1 1 d . . .
H10 H 0.1190 0.1665 0.3488 0.049 Uiso 1 1 calc R . .
C11 C 0.4246(5) 0.0573(2) 0.38428(7) 0.0403(5) Uani 1 1 d . . .
H11 H 0.5262 -0.0261 0.3822 0.048 Uiso 1 1 calc R . .
C12 C 0.4695(4) 0.1286(2) 0.42292(7) 0.0382(5) Uani 1 1 d . . .
C13 C 0.6845(4) 0.0743(2) 0.45524(6) 0.0383(5) Uani 1 1 d . . .
C14 C 0.6642(4) 0.2948(2) 0.49542(6) 0.0373(5) Uani 1 1 d . . .
C15 C 0.3288(4) 0.2618(2) 0.43143(7) 0.0397(5) Uani 1 1 d . . .
N1 N -0.2700(4) 0.1324(2) 0.14353(6) 0.0442(5) Uani 1 1 d . . .
N2 N 0.7668(4) 0.16327(18) 0.48916(5) 0.0377(4) Uani 1 1 d . . .
N3 N 0.4376(4) 0.3350(2) 0.46764(5) 0.0392(5) Uani 1 1 d . . .
O1 O 0.7945(3) -0.04204(15) 0.45319(5) 0.0439(4) Uani 1 1 d . . .
O2 O 0.7647(3) 0.37171(15) 0.52415(4) 0.0430(4) Uani 1 1 d . . .
O3 O 0.1292(3) 0.31258(17) 0.40893(5) 0.0491(5) Uani 1 1 d . . .
H2N H 0.891(6) 0.133(2) 0.5051(9) 0.044(7) Uiso 1 1 d . . .
H3N H 0.352(5) 0.414(3) 0.4717(7) 0.038(6) 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
C1 0.0497(12) 0.0565(15) 0.0354(11) 0.0062(10) -0.0043(10) -0.0022(10)
C2 0.0522(13) 0.0661(16) 0.0313(11) -0.0062(10) -0.0046(10) -0.0031(11)
C3 0.0429(11) 0.0425(13) 0.0313(10) 0.0000(9) 0.0004(8) -0.0073(9)
C4 0.0423(11) 0.0406(12) 0.0365(10) 0.0004(9) -0.0004(9) -0.0005(9)
C5 0.0447(11) 0.0410(13) 0.0311(10) -0.0035(8) 0.0006(9) -0.0054(9)
C6 0.0448(11) 0.0378(12) 0.0338(11) -0.0010(8) -0.0005(9) -0.0058(9)
C7 0.0484(11) 0.0392(12) 0.0376(11) -0.0010(9) -0.0021(9) 0.0009(9)
C8 0.0482(11) 0.0434(13) 0.0324(10) -0.0058(9) 0.0002(9) -0.0023(9)
C9 0.0472(11) 0.0394(12) 0.0360(11) 0.0006(9) -0.0022(9) -0.0009(9)
C10 0.0461(11) 0.0413(13) 0.0355(11) -0.0001(9) -0.0033(9) -0.0010(9)
C11 0.0444(11) 0.0390(12) 0.0373(11) 0.0016(9) -0.0009(9) -0.0003(9)
C12 0.0401(10) 0.0413(12) 0.0329(10) 0.0033(8) -0.0030(9) -0.0005(9)
C13 0.0439(11) 0.0416(13) 0.0294(10) 0.0015(8) -0.0003(9) 0.0019(9)
C14 0.0438(11) 0.0404(12) 0.0276(9) 0.0018(9) -0.0005(8) 0.0037(9)
C15 0.0436(11) 0.0441(13) 0.0312(10) 0.0011(8) -0.0017(9) 0.0011(9)
N1 0.0476(10) 0.0539(12) 0.0308(9) -0.0019(8) -0.0025(8) -0.0011(8)
N2 0.0444(10) 0.0403(11) 0.0280(8) 0.0014(7) -0.0049(8) 0.0062(8)
N3 0.0471(10) 0.0398(11) 0.0304(9) -0.0018(7) -0.0032(8) 0.0073(8)
O1 0.0548(9) 0.0394(9) 0.0368(8) -0.0022(6) -0.0080(7) 0.0086(7)
O2 0.0537(9) 0.0445(9) 0.0302(7) -0.0049(6) -0.0087(6) 0.0058(7)
O3 0.0544(9) 0.0504(10) 0.0417(8) -0.0057(7) -0.0150(7) 0.0129(7)

_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 N1 1.443(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.463(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.357(3) . ?
C3 C8 1.412(3) . ?
C3 C4 1.423(3) . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(3) . ?
C6 C9 1.432(3) . ?
C7 C8 1.373(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.407(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(3) . ?
C11 H11 0.9300 . ?
C12 C15 1.460(3) . ?
C12 C13 1.465(3) . ?
C13 O1 1.230(3) . ?
C13 N2 1.383(3) . ?
C14 O2 1.223(2) . ?
C14 N2 1.366(3) . ?
C14 N3 1.372(3) . ?
C15 O3 1.225(2) . ?
C15 N3 1.387(3) . ?
N2 H2N 0.79(3) . ?
N3 H3N 0.87(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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C8 121.75(19) . . ?
N1 C3 C4 120.9(2) . . ?
C8 C3 C4 117.33(18) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C7 116.84(19) . . ?
C5 C6 C9 123.6(2) . . ?
C7 C6 C9 119.5(2) . . ?
C8 C7 C6 122.4(2) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C3 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C10 C9 C6 128.1(2) . . ?
C10 C9 H9 116.0 . . ?
C6 C9 H9 116.0 . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 129.5(2) . . ?
C12 C11 H11 115.3 . . ?
C10 C11 H11 115.3 . . ?
C11 C12 C15 122.40(19) . . ?
C11 C12 C13 118.4(2) . . ?
C15 C12 C13 118.98(18) . . ?
O1 C13 N2 119.92(18) . . ?
O1 C13 C12 123.92(19) . . ?
N2 C13 C12 116.15(19) . . ?
O2 C14 N2 122.49(18) . . ?
O2 C14 N3 121.9(2) . . ?
N2 C14 N3 115.56(18) . . ?
O3 C15 N3 118.9(2) . . ?
O3 C15 C12 125.15(19) . . ?
N3 C15 C12 115.95(18) . . ?
C3 N1 C1 121.43(19) . . ?
C3 N1 C2 120.27(19) . . ?
C1 N1 C2 118.25(17) . . ?
C14 N2 C13 126.22(18) . . ?
C14 N2 H2N 119.9(18) . . ?
C13 N2 H2N 113.8(18) . . ?
C14 N3 C15 126.2(2) . . ?
C14 N3 H3N 119.7(15) . . ?
C15 N3 H3N 114.0(15) . . ?

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
N1 C3 C4 C5 -175.8(2) . . . . ?
C8 C3 C4 C5 3.7(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 -2.7(3) . . . . ?
C4 C5 C6 C9 174.8(2) . . . . ?
C5 C6 C7 C8 2.8(3) . . . . ?
C9 C6 C7 C8 -174.8(2) . . . . ?
C6 C7 C8 C3 0.4(3) . . . . ?
N1 C3 C8 C7 175.8(2) . . . . ?
C4 C3 C8 C7 -3.6(3) . . . . ?
C5 C6 C9 C10 -5.1(4) . . . . ?
C7 C6 C9 C10 172.3(2) . . . . ?
C6 C9 C10 C11 -177.4(2) . . . . ?
C9 C10 C11 C12 170.8(2) . . . . ?
C10 C11 C12 C15 -0.4(4) . . . . ?
C10 C11 C12 C13 -175.4(2) . . . . ?
C11 C12 C13 O1 -11.8(3) . . . . ?
C15 C12 C13 O1 172.99(19) . . . . ?
C11 C12 C13 N2 166.98(19) . . . . ?
C15 C12 C13 N2 -8.2(3) . . . . ?
C11 C12 C15 O3 11.4(3) . . . . ?
C13 C12 C15 O3 -173.6(2) . . . . ?
C11 C12 C15 N3 -167.6(2) . . . . ?
C13 C12 C15 N3 7.4(3) . . . . ?
C8 C3 N1 C1 -178.87(19) . . . . ?
C4 C3 N1 C1 0.5(3) . . . . ?
C8 C3 N1 C2 -1.6(3) . . . . ?
C4 C3 N1 C2 177.8(2) . . . . ?
O2 C14 N2 C13 -173.8(2) . . . . ?
N3 C14 N2 C13 6.9(3) . . . . ?
O1 C13 N2 C14 179.74(19) . . . . ?
C12 C13 N2 C14 0.9(3) . . . . ?
O2 C14 N3 C15 172.9(2) . . . . ?
N2 C14 N3 C15 -7.8(3) . . . . ?
O3 C15 N3 C14 -178.2(2) . . . . ?
C12 C15 N3 C14 0.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        65.53
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.070