# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2007

data_global
_journal_name_full               'New J.Chem.'
_journal_coden_cambridge         0440

_publ_section_title              
;An experimental and theoretical investigation of the molecular and
electronic structure of 2-amino-4-chloro-6-pyrazolyl-[1,3,5]triazine,
forming supramolecular linear tapes in solid state
;
_publ_contact_author_name        'Prof. Claudio Pettinari'
_publ_contact_author_email       CLAUDIO.PETTINARI@UNICAM.IT
loop_
_publ_author_name
M.Casarin
F.Garau
L.Pandolfo
C.Pettinari
A.Venzo
M.Monari

# Attachment 'cmpd1.CIF'

data_cmpd1
_database_code_depnum_ccdc_archive 'CCDC 662889'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H5 Cl N6'
_chemical_formula_weight         196.61

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   4.2896(5)
_cell_length_b                   5.4645(6)
_cell_length_c                   17.528(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.449(2)
_cell_angle_gamma                90.00
_cell_volume                     410.72(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2386
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      28.49

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             200
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 SMART APEX II area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3337
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         28.50
_reflns_number_total             1848
_reflns_number_gt                1766
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Farrugia, 2003)'
_computing_publication_material  '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^)+(0.0492P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_number_reflns         1848
_refine_ls_number_parameters     126
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.093
_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
Cl1 Cl -0.01395(7) 0.14477(8) -0.17510(2) 0.05778(15) Uani 1 1 d . . .
N5 N 0.0691(3) 0.2390(2) -0.03189(6) 0.0373(2) Uani 1 1 d . . .
N4 N -0.2755(3) 0.5004(2) -0.10208(7) 0.0404(3) Uani 1 1 d . . .
N3 N -0.1861(3) 0.5651(2) 0.03202(7) 0.0371(2) Uani 1 1 d . . .
C4 C -0.3247(4) 0.6211(2) -0.03580(10) 0.0373(3) Uani 1 1 d . . .
C6 C 0.0055(3) 0.3769(2) 0.02870(8) 0.0331(3) Uani 1 1 d . . .
C5 C -0.0838(3) 0.3157(3) -0.09385(8) 0.0373(3) Uani 1 1 d . . .
C3 C 0.1775(4) 0.4465(4) 0.16267(9) 0.0502(4) Uani 1 1 d . . .
H3 H 0.0746 0.5926 0.1723 0.060 Uiso 1 1 calc R . .
C1 C 0.4663(5) 0.1181(4) 0.17118(12) 0.0586(5) Uani 1 1 d . . .
H1 H 0.6005 -0.0003 0.1914 0.070 Uiso 1 1 calc R . .
C2 C 0.3684(5) 0.3218(4) 0.21159(11) 0.0591(5) Uani 1 1 d . . .
H2 H 0.4225 0.3636 0.2616 0.071 Uiso 1 1 calc R . .
N1 N 0.1661(3) 0.3150(2) 0.09652(7) 0.0373(3) Uani 1 1 d . . .
N6 N -0.5233(3) 0.8058(3) -0.03783(9) 0.0486(3) Uani 1 1 d D . .
N2 N 0.3479(3) 0.1114(3) 0.10090(8) 0.0486(3) Uani 1 1 d . . .
H6B H -0.542(5) 0.886(3) 0.0032(11) 0.045(5) Uiso 1 1 d D . .
H6A H -0.592(6) 0.853(4) -0.0817(13) 0.068(7) Uiso 1 1 d 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
Cl1 0.0812(3) 0.0575(2) 0.03425(18) -0.01075(16) -0.00618(15) 0.0191(2)
N5 0.0442(6) 0.0348(5) 0.0326(5) -0.0015(5) -0.0036(5) 0.0101(5)
N4 0.0446(6) 0.0388(6) 0.0376(6) 0.0017(5) -0.0056(4) 0.0084(5)
N3 0.0395(6) 0.0352(6) 0.0366(6) -0.0026(5) 0.0014(4) 0.0061(5)
C4 0.0346(6) 0.0331(6) 0.0442(8) 0.0031(5) 0.0006(5) 0.0027(5)
C6 0.0331(6) 0.0326(6) 0.0335(7) 0.0012(5) 0.0000(5) 0.0017(5)
C5 0.0436(7) 0.0362(7) 0.0321(7) -0.0018(5) -0.0009(5) 0.0031(5)
C3 0.0568(9) 0.0563(10) 0.0372(8) -0.0094(7) -0.0021(6) -0.0004(7)
C1 0.0639(11) 0.0644(11) 0.0463(10) 0.0125(8) -0.0179(8) 0.0054(8)
C2 0.0682(12) 0.0723(12) 0.0362(10) 0.0004(7) -0.0111(8) -0.0081(9)
N1 0.0408(6) 0.0395(6) 0.0315(6) 0.0008(4) -0.0033(4) 0.0043(5)
N6 0.0520(8) 0.0427(8) 0.0509(9) -0.0003(6) -0.0024(6) 0.0164(6)
N2 0.0552(8) 0.0461(8) 0.0440(8) 0.0039(5) -0.0099(6) 0.0122(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
Cl1 C5 1.7356(14) . ?
N5 C5 1.3227(18) . ?
N5 C6 1.3359(18) . ?
N4 C5 1.3074(19) . ?
N4 C4 1.357(2) . ?
N3 C6 1.3187(18) . ?
N3 C4 1.351(2) . ?
C4 N6 1.3206(19) . ?
C6 N1 1.4003(19) . ?
C3 C2 1.354(3) . ?
C3 N1 1.364(2) . ?
C3 H3 0.9300 . ?
C1 N2 1.321(2) . ?
C1 C2 1.390(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
N1 N2 1.3597(19) . ?
N6 H6B 0.848(19) . ?
N6 H6A 0.86(2) . ?

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
C5 N5 C6 111.52(11) . . ?
C5 N4 C4 113.07(13) . . ?
C6 N3 C4 113.51(12) . . ?
N6 C4 N3 117.79(15) . . ?
N6 C4 N4 117.57(16) . . ?
N3 C4 N4 124.64(13) . . ?
N3 C6 N5 127.96(13) . . ?
N3 C6 N1 116.40(12) . . ?
N5 C6 N1 115.64(12) . . ?
N4 C5 N5 129.26(13) . . ?
N4 C5 Cl1 116.49(11) . . ?
N5 C5 Cl1 114.25(10) . . ?
C2 C3 N1 106.34(16) . . ?
C2 C3 H3 126.8 . . ?
N1 C3 H3 126.8 . . ?
N2 C1 C2 112.54(17) . . ?
N2 C1 H1 123.7 . . ?
C2 C1 H1 123.7 . . ?
C3 C2 C1 105.42(16) . . ?
C3 C2 H2 127.3 . . ?
C1 C2 H2 127.3 . . ?
N2 N1 C3 112.03(13) . . ?
N2 N1 C6 120.97(12) . . ?
C3 N1 C6 126.92(14) . . ?
C4 N6 H6B 116.6(14) . . ?
C4 N6 H6A 117.4(16) . . ?
H6B N6 H6A 125(2) . . ?
C1 N2 N1 103.66(15) . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        28.50
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.058
#===END