# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004



data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Dirk Steinborn'
'Clemens Bruhn'
'Thomas Kruger'

_publ_contact_author_name        'ProfD Dirk Steinborn'
_publ_contact_author_address     
;
Institut fur Anorganische Chemie
Martin-Luther-Universitat Halle-Wittenberg
Kurt-Mothes-Strasse 2
Halle
D-06120
GERMANY
;

_publ_contact_author_email       STEINBORN@CHEMIE.UNI-HALLE.DE
_publ_requested_category         ?
_publ_requested_coeditor_name    ?

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Synthesis of [(MeCyt)2H]I - structure and
stability of a dimeric threefold hydrogen-bonded 1-methylcytosinium
1-methycytosine cation
;

data_stadi744
_database_code_depnum_ccdc_archive 'CCDC 239325'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H15 N6 O2, I'
_chemical_formula_sum            'C10 H15 I N6 O2'
_chemical_formula_weight         378.18

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'
I I -0.4742 1.8119 '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_H-M   'P 21/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                   7.2200(8)
_cell_length_b                   8.7222(13)
_cell_length_c                   11.6617(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.271(11)
_cell_angle_gamma                90.00
_cell_volume                     726.75(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      8.4
_cell_measurement_theta_max      18.1

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    2.212
_exptl_absorpt_correction_type   psi-scans
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   ?

_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  'Stoe Stadi4 4-circle diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         1
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        none
_diffrn_reflns_number            2560
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1280
_reflns_number_gt                1025
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_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^)+(0.0243P)^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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0192(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1280
_refine_ls_number_parameters     112
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
C1 C 0.4596(7) 0.3119(6) -0.1395(5) 0.0790(13) Uani 1 1 d . . .
H1A H 0.456(6) 0.258(5) -0.211(4) 0.096(8) Uiso 1 1 d . . .
H1B H 0.368(6) 0.400(5) -0.154(4) 0.096(8) Uiso 1 1 d . . .
H1C H 0.579(6) 0.344(5) -0.115(4) 0.096(8) Uiso 1 1 d . . .
C2 C 0.2402(4) 0.1359(3) -0.0685(3) 0.0469(8) Uani 1 1 d . . .
C4 C 0.2834(5) 0.0544(3) 0.1288(3) 0.0445(8) Uani 1 1 d . . .
C5 C 0.4543(5) 0.1367(4) 0.1503(3) 0.0553(9) Uani 1 1 d . . .
H5 H 0.5276 0.1345 0.2227 0.072(12) Uiso 1 1 calc R . .
C6 C 0.5066(5) 0.2174(4) 0.0630(4) 0.0573(9) Uani 1 1 d . . .
H6 H 0.6157 0.2754 0.0766 0.077(12) Uiso 1 1 calc R . .
N1 N 0.4054(4) 0.2180(3) -0.0455(3) 0.0521(7) Uani 1 1 d . . .
N3 N 0.1838(4) 0.0572(3) 0.0219(2) 0.0422(6) Uani 1 1 d . . .
H3 H 0.073(8) 0.027(6) 0.008(5) 0.026(15) Uiso 0.50 1 d P . .
N4 N 0.2198(5) -0.0255(4) 0.2102(3) 0.0596(8) Uani 1 1 d D . .
H4A H 0.282(5) -0.025(4) 0.283(3) 0.066(8) Uiso 1 1 d D . .
H4B H 0.105(4) -0.067(4) 0.198(3) 0.066(8) Uiso 1 1 d D . .
I I 0.0000 0.5000 0.0000 0.0679(2) Uani 1 2 d S . .
O O 0.1512(3) 0.1332(3) -0.16663(19) 0.0549(6) Uani 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 0.062(3) 0.079(3) 0.097(4) 0.025(3) 0.015(3) -0.005(2)
C2 0.0421(18) 0.0437(18) 0.054(2) -0.0009(15) 0.0059(17) 0.0089(14)
C4 0.0411(18) 0.0451(17) 0.045(2) -0.0092(14) -0.0034(17) 0.0085(13)
C5 0.047(2) 0.059(2) 0.055(2) -0.0106(17) -0.0106(18) 0.0015(16)
C6 0.0408(19) 0.050(2) 0.077(3) -0.0154(18) -0.0071(19) -0.0006(15)
N1 0.0417(15) 0.0507(16) 0.0625(18) 0.0033(13) 0.0026(14) 0.0003(13)
N3 0.0366(15) 0.0484(15) 0.0386(17) -0.0048(11) -0.0052(14) 0.0015(12)
N4 0.0535(19) 0.089(3) 0.0329(16) 0.0012(15) -0.0063(16) -0.0054(16)
I 0.0595(3) 0.0922(3) 0.0467(3) -0.01770(18) -0.00980(17) 0.01652(19)
O 0.0561(14) 0.0659(15) 0.0391(13) 0.0095(11) -0.0049(11) 0.0012(11)

_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 1.465(5) . ?
C1 H1A 0.96(4) . ?
C1 H1B 1.01(4) . ?
C1 H1C 0.92(4) . ?
C2 O 1.229(4) . ?
C2 N3 1.369(4) . ?
C2 N1 1.384(4) . ?
C4 N4 1.313(5) . ?
C4 N3 1.347(4) . ?
C4 C5 1.418(5) . ?
C5 C6 1.336(5) . ?
C5 H5 0.9300 . ?
C6 N1 1.367(5) . ?
C6 H6 0.9300 . ?
N3 H3 0.83(5) . ?
N4 H4A 0.90(3) . ?
N4 H4B 0.90(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 114(3) . . ?
N1 C1 H1B 108(2) . . ?
H1A C1 H1B 107(4) . . ?
N1 C1 H1C 106(3) . . ?
H1A C1 H1C 109(4) . . ?
H1B C1 H1C 113(4) . . ?
O C2 N3 122.3(3) . . ?
O C2 N1 120.7(3) . . ?
N3 C2 N1 117.0(3) . . ?
N4 C4 N3 118.9(3) . . ?
N4 C4 C5 121.8(3) . . ?
N3 C4 C5 119.3(3) . . ?
C6 C5 C4 117.8(3) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C5 C6 N1 122.4(3) . . ?
C5 C6 H6 118.8 . . ?
N1 C6 H6 118.8 . . ?
C6 N1 C2 120.6(3) . . ?
C6 N1 C1 122.0(3) . . ?
C2 N1 C1 117.3(3) . . ?
C4 N3 C2 122.9(3) . . ?
C4 N3 H3 123(4) . . ?
C2 N3 H3 113(4) . . ?
C4 N4 H4A 120(2) . . ?
C4 N4 H4B 121(2) . . ?
H4A N4 H4B 119(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.063