# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Beverina, Luca '

_publ_contact_author_name        'Beverina, Luca '
_publ_contact_author_email       luca.beverina@mater.unimib.it

_publ_section_title              
;
UV Absorbing Zwitterionic Pyridinium-Tetrazolate.
Exceptional Transparency/Optical Nonlinearity Tradeoff
;

# Attachment '- LBZW01.cif'

data_LBZW01
_database_code_depnum_ccdc_archive 'CCDC 779200'
#TrackingRef '- LBZW01.cif'

_audit_creation_date             2009-11-04
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          547
_chemical_formula_moiety         'C7 H7 N5'
_chemical_formula_sum            'C7 H7 N5'
_chemical_formula_weight         161.18

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   c_2/c
_symmetry_space_group_name_Hall  -C2yc

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

_cell_length_a                   10.5257(10)
_cell_length_b                   10.8919(11)
_cell_length_c                   7.0298(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.360(2)
_cell_angle_gamma                90.00
_cell_volume                     764.91(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1012
_cell_measurement_theta_min      2.766
_cell_measurement_theta_max      24.566

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark orange'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9063
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS-2007/4

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker AXS Smart'
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_number            4877
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         27.51
_reflns_number_total             878
_reflns_number_gt                623
_reflns_threshold_expression     >2sigma(I)

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0382P)^2^+0.1800P] 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_number_reflns         878
_refine_ls_number_parameters     77
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.012
_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 0.5000 0.12982(16) 0.2500 0.0448(5) Uani 1 2 d S . .
C2 C 0.5000 -0.00380(16) 0.2500 0.0427(4) Uani 1 2 d S . .
C3 C 0.61306(14) -0.07005(13) 0.2516(2) 0.0508(4) Uani 1 1 d . . .
C4 C 0.61061(15) -0.19554(14) 0.2507(2) 0.0551(4) Uani 1 1 d . . .
C5 C 0.5000 -0.3921(2) 0.2500 0.0754(8) Uani 1 2 d S . .
N1 N 0.5000 -0.25650(14) 0.2500 0.0531(5) Uani 1 2 d S . .
N2 N 0.39713(12) 0.19817(11) 0.25869(18) 0.0566(4) Uani 1 1 d . . .
N3 N 0.43879(13) 0.31422(11) 0.2553(2) 0.0661(4) Uani 1 1 d . . .
H3 H 0.6960(16) -0.0286(12) 0.254(2) 0.060(4) Uiso 1 1 d . . .
H4 H 0.6885(16) -0.2474(14) 0.250(2) 0.073(5) Uiso 1 1 d . . .
H5A H 0.582(4) -0.421(3) 0.206(8) 0.078(11) Uiso 0.50 1 d P . .
H5B H 0.411(4) -0.419(3) 0.141(7) 0.071(10) Uiso 0.50 1 d P . .
H5C H 0.507(6) -0.417(3) 0.388(6) 0.077(11) Uiso 0.50 1 d P . .

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 0.0507(10) 0.0391(10) 0.0472(11) 0.000 0.0193(8) 0.000
C2 0.0492(10) 0.0374(10) 0.0445(10) 0.000 0.0190(8) 0.000
C3 0.0488(8) 0.0448(8) 0.0635(9) 0.0035(6) 0.0246(7) 0.0006(6)
C4 0.0595(9) 0.0457(8) 0.0653(10) 0.0051(6) 0.0270(7) 0.0101(7)
C5 0.117(3) 0.0346(11) 0.079(2) 0.000 0.037(2) 0.000
N1 0.0679(11) 0.0357(8) 0.0600(11) 0.000 0.0263(9) 0.000
N2 0.0627(8) 0.0387(6) 0.0743(9) 0.0000(5) 0.0299(6) 0.0055(5)
N3 0.0816(9) 0.0395(7) 0.0831(9) 0.0005(6) 0.0346(8) 0.0068(6)

_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 N2 1.3312(14) . ?
C1 N2 1.3312(14) 2_655 ?
C1 C2 1.455(2) . ?
C2 C3 1.3887(17) 2_655 ?
C2 C3 1.3887(17) . ?
C3 C4 1.367(2) . ?
C3 H3 0.978(15) . ?
C4 N1 1.3390(17) . ?
C4 H4 0.997(17) . ?
C5 N1 1.477(3) . ?
C5 H5A 1.05(4) . ?
C5 H5B 1.04(4) . ?
C5 H5C 0.98(4) . ?
N1 C4 1.3390(17) 2_655 ?
N2 N3 1.3406(17) . ?
N3 N3 1.314(3) 2_655 ?

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
N2 C1 N2 111.99(16) . 2_655 ?
N2 C1 C2 124.01(8) . . ?
N2 C1 C2 124.01(8) 2_655 . ?
C3 C2 C3 117.39(18) 2_655 . ?
C3 C2 C1 121.30(9) 2_655 . ?
C3 C2 C1 121.30(9) . . ?
C4 C3 C2 120.31(14) . . ?
C4 C3 H3 118.5(8) . . ?
C2 C3 H3 121.2(8) . . ?
N1 C4 C3 120.73(14) . . ?
N1 C4 H4 115.8(9) . . ?
C3 C4 H4 123.5(9) . . ?
N1 C5 H5A 107.4(19) . . ?
N1 C5 H5B 106.0(18) . . ?
H5A C5 H5B 109(2) . . ?
N1 C5 H5C 106(2) . . ?
H5A C5 H5C 113(2) . . ?
H5B C5 H5C 115(2) . . ?
C4 N1 C4 120.54(17) . 2_655 ?
C4 N1 C5 119.73(9) . . ?
C4 N1 C5 119.73(9) 2_655 . ?
C1 N2 N3 104.55(12) . . ?
N3 N3 N2 109.46(7) 2_655 . ?

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
N2 C1 C2 C3 3.52(9) . . . 2_655 ?
N2 C1 C2 C3 -176.48(9) 2_655 . . 2_655 ?
N2 C1 C2 C3 -176.48(9) . . . . ?
N2 C1 C2 C3 3.52(9) 2_655 . . . ?
C3 C2 C3 C4 0.28(10) 2_655 . . . ?
C1 C2 C3 C4 -179.72(10) . . . . ?
C2 C3 C4 N1 -0.6(2) . . . . ?
C3 C4 N1 C4 0.29(10) . . . 2_655 ?
C3 C4 N1 C5 -179.71(10) . . . . ?
N2 C1 N2 N3 -0.04(7) 2_655 . . . ?
C2 C1 N2 N3 179.96(7) . . . . ?
C1 N2 N3 N3 0.10(18) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030