# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is © The Owner Societies 2012


data_global
_journal_name_full               Phys.Chem.Chem.Phys.(PCCP)
_journal_coden_cambridge         1326
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       lucjan.jerzykiewicz@chem.uni.wroc.pl
_publ_contact_author_name        'Lucjan Jerzykiewicz'
loop_
_publ_author_name
A.Szemik-Hojniak
L.Wisniewski
I.Deperasinska
A.Makarewicz
A.Puszko
Y.Erez
D.Huppert
'Lucjan Jerzykiewicz'

data_szem03n
_database_code_depnum_ccdc_archive 'CCDC 863885'
#TrackingRef 'web_deposit_cif_file_0_LucjanJerzykiewicz_1326961885.SZEM03N.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H15 N3 O3'
_chemical_formula_sum            'C10 H15 N3 O3'
_chemical_formula_weight         225.25

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

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                   5.728(3)
_cell_length_b                   8.033(3)
_cell_length_c                   24.575(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.02(3)
_cell_angle_gamma                90.00
_cell_volume                     1128.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    3896
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26

_exptl_crystal_description       plate
_exptl_crystal_colour            Yellowish-golden
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.100
_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      100(1)
_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  'Kuma KM-4 CCD'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8575
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.88
_reflns_number_total             2693
_reflns_number_gt                1919
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2001)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2001)'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-NT (Bruker, 1999)'
_computing_publication_material  SHELXL97

_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^)+(0.0488P)^2^+0.4481P] 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         2693
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_restrained_S_all      1.234
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.002

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
O1 O 0.1550(3) 0.3846(2) 0.06949(8) 0.0286(5) Uani 1 1 d . . .
O2 O 0.7259(4) 0.1849(3) -0.12756(8) 0.0368(6) Uani 1 1 d . . .
O3 O 0.9290(3) 0.0815(3) -0.05857(8) 0.0385(6) Uani 1 1 d . . .
N1 N 0.2965(4) 0.3326(3) 0.03300(9) 0.0212(5) Uani 1 1 d . . .
N2 N 0.7609(4) 0.1597(3) -0.07829(10) 0.0237(6) Uani 1 1 d . . .
N3 N 0.5032(4) 0.2037(3) 0.10518(10) 0.0242(6) Uani 1 1 d . . .
C1 C 0.4865(4) 0.2374(3) 0.05159(11) 0.0205(6) Uani 1 1 d . . .
C2 C 0.6392(4) 0.1860(3) 0.01367(11) 0.0192(6) Uani 1 1 d . . .
H2 H 0.7717 0.1248 0.0249 0.023 Uiso 1 1 calc R . .
C3 C 0.5946(4) 0.2258(3) -0.04100(11) 0.0189(6) Uani 1 1 d . . .
C4 C 0.4026(4) 0.3218(3) -0.05984(11) 0.0201(6) Uani 1 1 d . . .
C5 C 0.2595(5) 0.3716(3) -0.02025(11) 0.0228(6) Uani 1 1 d . . .
H5 H 0.1294 0.4362 -0.0308 0.027 Uiso 1 1 calc R . .
C6 C 0.3362(5) 0.3766(4) -0.11756(11) 0.0285(7) Uani 1 1 d . . .
H61 H 0.4639 0.4371 -0.1314 0.043 Uiso 1 1 calc R . .
H62 H 0.2007 0.4470 -0.1180 0.043 Uiso 1 1 calc R . .
H63 H 0.3019 0.2807 -0.1400 0.043 Uiso 1 1 calc R . .
C7 C 0.7078(4) 0.1255(3) 0.13273(11) 0.0224(6) Uani 1 1 d . . .
H71 H 0.8441 0.1947 0.1285 0.027 Uiso 1 1 calc R . .
H72 H 0.7347 0.0186 0.1159 0.027 Uiso 1 1 calc R . .
C8 C 0.6764(5) 0.1007(3) 0.19285(11) 0.0242(6) Uani 1 1 d . . .
H81 H 0.5378 0.0336 0.1969 0.029 Uiso 1 1 calc R . .
H82 H 0.6517 0.2080 0.2096 0.029 Uiso 1 1 calc R . .
C9 C 0.8857(5) 0.0162(4) 0.22260(11) 0.0275(7) Uani 1 1 d . . .
H91 H 1.0215 0.0878 0.2211 0.033 Uiso 1 1 calc R . .
H92 H 0.9185 -0.0867 0.2040 0.033 Uiso 1 1 calc R . .
C10 C 0.8473(6) -0.0221(4) 0.28194(12) 0.0373(8) Uani 1 1 d . . .
H101 H 0.9840 -0.0755 0.2987 0.056 Uiso 1 1 calc R . .
H102 H 0.7148 -0.0946 0.2837 0.056 Uiso 1 1 calc R . .
H103 H 0.8189 0.0797 0.3009 0.056 Uiso 1 1 calc R . .
H3 H 0.406(5) 0.246(3) 0.1209(11) 0.015(8) 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
O1 0.0227(10) 0.0351(12) 0.0287(12) -0.0001(9) 0.0076(9) 0.0122(9)
O2 0.0459(14) 0.0389(13) 0.0262(13) 0.0034(10) 0.0067(10) 0.0128(10)
O3 0.0286(11) 0.0534(15) 0.0333(13) -0.0024(10) 0.0016(10) 0.0218(11)
N1 0.0173(12) 0.0201(12) 0.0264(14) 0.0005(10) 0.0019(10) 0.0043(9)
N2 0.0208(13) 0.0202(13) 0.0305(16) -0.0025(11) 0.0039(11) 0.0004(10)
N3 0.0214(14) 0.0288(14) 0.0230(15) 0.0015(11) 0.0053(11) 0.0103(11)
C1 0.0177(14) 0.0186(14) 0.0247(17) 0.0006(12) -0.0010(12) -0.0001(11)
C2 0.0158(13) 0.0148(13) 0.0268(17) 0.0009(12) -0.0009(11) 0.0015(10)
C3 0.0161(13) 0.0151(13) 0.0257(17) -0.0030(11) 0.0032(11) -0.0001(10)
C4 0.0201(14) 0.0149(14) 0.0249(16) 0.0011(12) -0.0016(12) -0.0010(11)
C5 0.0204(14) 0.0171(14) 0.0303(18) 0.0015(13) -0.0030(12) 0.0020(11)
C6 0.0293(16) 0.0266(16) 0.0293(18) 0.0015(13) 0.0008(13) 0.0058(13)
C7 0.0192(14) 0.0243(15) 0.0233(16) 0.0012(12) -0.0007(11) 0.0038(11)
C8 0.0230(14) 0.0260(15) 0.0233(16) -0.0023(13) 0.0005(12) 0.0016(12)
C9 0.0311(16) 0.0268(16) 0.0241(17) -0.0031(13) -0.0019(13) 0.0055(13)
C10 0.0421(19) 0.0391(19) 0.0298(18) -0.0008(15) -0.0047(14) 0.0032(15)

_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
O1 N1 1.318(3) . ?
O2 N2 1.230(3) . ?
O3 N2 1.220(3) . ?
N1 C5 1.348(3) . ?
N1 C1 1.381(3) . ?
N2 C3 1.467(3) . ?
N3 C1 1.341(3) . ?
N3 C7 1.454(3) . ?
N3 H3 0.78(3) . ?
C1 C2 1.385(4) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(4) . ?
C4 C5 1.375(4) . ?
C4 C6 1.508(4) . ?
C5 H5 0.9300 . ?
C6 H61 0.9600 . ?
C6 H62 0.9600 . ?
C6 H63 0.9600 . ?
C7 C8 1.514(4) . ?
C7 H71 0.9700 . ?
C7 H72 0.9700 . ?
C8 C9 1.519(4) . ?
C8 H81 0.9700 . ?
C8 H82 0.9700 . ?
C9 C10 1.522(4) . ?
C9 H91 0.9700 . ?
C9 H92 0.9700 . ?
C10 H101 0.9600 . ?
C10 H102 0.9600 . ?
C10 H103 0.9600 . ?

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
O1 N1 C5 121.6(2) . . ?
O1 N1 C1 117.3(2) . . ?
C5 N1 C1 121.1(2) . . ?
O3 N2 O2 123.0(2) . . ?
O3 N2 C3 117.8(2) . . ?
O2 N2 C3 119.1(2) . . ?
C1 N3 C7 122.9(2) . . ?
C1 N3 H3 113(2) . . ?
C7 N3 H3 123(2) . . ?
N3 C1 N1 115.9(2) . . ?
N3 C1 C2 126.6(3) . . ?
N1 C1 C2 117.5(2) . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 122.4(2) . . ?
C2 C3 N2 116.0(2) . . ?
C4 C3 N2 121.6(2) . . ?
C5 C4 C3 114.9(2) . . ?
C5 C4 C6 117.2(2) . . ?
C3 C4 C6 127.9(2) . . ?
N1 C5 C4 123.9(2) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C4 C6 H61 109.5 . . ?
C4 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
C4 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
N3 C7 C8 111.4(2) . . ?
N3 C7 H71 109.4 . . ?
C8 C7 H71 109.4 . . ?
N3 C7 H72 109.4 . . ?
C8 C7 H72 109.4 . . ?
H71 C7 H72 108.0 . . ?
C7 C8 C9 112.6(2) . . ?
C7 C8 H81 109.1 . . ?
C9 C8 H81 109.1 . . ?
C7 C8 H82 109.1 . . ?
C9 C8 H82 109.1 . . ?
H81 C8 H82 107.8 . . ?
C8 C9 C10 112.9(2) . . ?
C8 C9 H91 109.0 . . ?
C10 C9 H91 109.0 . . ?
C8 C9 H92 109.0 . . ?
C10 C9 H92 109.0 . . ?
H91 C9 H92 107.8 . . ?
C9 C10 H101 109.5 . . ?
C9 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
C9 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 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
C7 N3 C1 N1 -171.2(2) . . . . ?
C7 N3 C1 C2 9.1(4) . . . . ?
O1 N1 C1 N3 1.9(3) . . . . ?
C5 N1 C1 N3 -178.8(2) . . . . ?
O1 N1 C1 C2 -178.4(2) . . . . ?
C5 N1 C1 C2 1.0(4) . . . . ?
N3 C1 C2 C3 177.7(3) . . . . ?
N1 C1 C2 C3 -2.0(4) . . . . ?
C1 C2 C3 C4 2.1(4) . . . . ?
C1 C2 C3 N2 -177.4(2) . . . . ?
O3 N2 C3 C2 -2.9(3) . . . . ?
O2 N2 C3 C2 177.1(2) . . . . ?
O3 N2 C3 C4 177.6(2) . . . . ?
O2 N2 C3 C4 -2.4(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
N2 C3 C4 C5 178.6(2) . . . . ?
C2 C3 C4 C6 178.8(3) . . . . ?
N2 C3 C4 C6 -1.8(4) . . . . ?
O1 N1 C5 C4 179.4(2) . . . . ?
C1 N1 C5 C4 0.2(4) . . . . ?
C3 C4 C5 N1 -0.2(4) . . . . ?
C6 C4 C5 N1 -179.9(2) . . . . ?
C1 N3 C7 C8 -179.3(2) . . . . ?
N3 C7 C8 C9 179.0(2) . . . . ?
C7 C8 C9 C10 -175.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3N O1 0.78(3) 2.16(3) 2.572(3) 114(2) . yes
C2 H2A O3 0.93 2.48 3.401(4) 169 3_755 yes
C5 H5A O1 0.93 2.33 3.246(4) 170 3_565 yes
C7 H7B O3 0.97 2.59 3.309(4) 131 3_755 yes

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        28.41
_diffrn_measured_fraction_theta_full 0.948
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.047