Electronic Supplementary Material for CrystEngComm
This Journal is (c) The Royal Society of Chemistry 2007

data_global

#====================================================================
_journal_coden_Cambridge         1350
# 1. SUBMISSION DETAILS
_publ_contact_author             'Dr. Malcolm A. Halcrow'
_publ_contact_author_address     
;
School of Chemistry,
University of Leeds,
Woodhouse Lane,
Leeds LS2 9JT,
UK
;
_publ_contact_author_phone       '+44 (0)113 3436506'
_publ_contact_author_fax         '+44 (0)113 3436565'
_publ_contact_author_email       m.a.halcrow@leeds.ac.uk
_publ_requested_journal          CrystEngComm
_publ_contact_letter             
;
The following set of data is for one structure included in a
manuscript we have submitted to the CrystEngComm office.
;

#=======================================================================

# 2. TITLE AND AUTHOR LIST

_publ_section_title              
;
Zwitterionic 2-(4-Pyridyl)malondialdehyde Sesquihydrate Forms a Helical,
Three-Dimensional Hydrogen-Bonded Lattice
;
loop_
_publ_author_name
_publ_author_address
'Clare A. Tovee'
;
School of Chemistry,
University of Leeds,
Woodhouse Lane,
Leeds LS2 9JT,
UK
;
'Colin A. Kilner'
;
School of Chemistry,
University of Leeds,
Woodhouse Lane,
Leeds LS2 9JT,
UK
;
'Jim A. Thomas'
;
Department of Chemistry,
University of Sheffield,
Sheffield S3 7HF,
UK
;
'Malcolm A. Halcrow'
;
School of Chemistry,
University of Leeds,
Woodhouse Lane,
Leeds LS2 9JT,
UK
;

#=================================================================

data_c:\datasets\leeds\cat26\cat26
_database_code_depnum_ccdc_archive 'CCDC 642043'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-(4-Pyridyl)malondialdehyde Sesquihydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N O2, 1.5[H2 O]'
_chemical_formula_sum            'C8 H10 N O3.50'
_chemical_formula_weight         176.17

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_H-M   'C 2/c'

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                   24.2053(5)
_cell_length_b                   3.7445(1)
_cell_length_c                   20.9542(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.3149(11)
_cell_angle_gamma                90.00
_cell_volume                     1622.55(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11446
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      27.42

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Pale brown'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
;
Using multiple and symmetry-related data measurements via the program SORTAV
See R.H. Blessing, Acta Cryst (1995), A51, 33-38
;

_exptl_special_details           
;
Detector set at 30mm from sample with different 2theta offsets
1 degree phi exposures for chi=0 degree settings
1 degree omega exposures for chi=90 degree settings
;

_diffrn_ambient_temperature      150(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  'Nonius KappaCCD area detector diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11446
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.42
_reflns_number_total             1846
_reflns_number_gt                1338
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSEED (Barbour, 2003)'
_computing_publication_material  'local program'

_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.

The asymmetric unit contains one molecule of the zwitterionic organic
molecule (N1--O11); half a molecule of water (O12) lying on the C~2~ axis
(0, y, 1/4); and a whole molecule of water lying on a general position
(O13). No disorder is present in the model, and all non-H atoms were
refined anisotropically. All H atoms were located in the difference
map, and were refined freely with a common U~iso~ thermal parameter of
0.0407(18)\%A^2^. The refined distances involving these H atoms ranged
from C---H = 0.94(2)--1.06(2)\%A, N---H = 0.92(2)\%A and O---H =
0.92(2)--0.98(2)\%A. The zwitterionic nature of the compound is confirmed
by the location of H1 on the pyridyl N atom; by the position of O(12)
within hydrogen bonding distance of N(1); and, by the approximate
C~2~-symmetry of the 3-hydroxypropenalate moiety. If this were protonated,
then the C=O and C---O bond lengths should be clearly distinguishable
(compare e.g. Acta Chem. Scand. 1977, B31, 114 and Inorg. Chem. 2000,
39, 3902).
;

_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^)+(0.1027P)^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    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1846
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
N1 N 0.06726(7) 0.1206(4) 0.38686(8) 0.0285(4) Uani 1 1 d . . .
H1 H 0.0426(11) 0.224(6) 0.3408(13) 0.0407(18) Uiso 1 1 d . . .
C2 C 0.03704(9) 0.0003(5) 0.42141(9) 0.0292(4) Uani 1 1 d . . .
H2 H -0.0090(11) 0.029(6) 0.3962(14) 0.0407(18) Uiso 1 1 d . . .
C3 C 0.07202(8) -0.1390(5) 0.49233(9) 0.0276(4) Uani 1 1 d . . .
H3 H 0.0491(10) -0.225(6) 0.5140(13) 0.0407(18) Uiso 1 1 d . . .
C4 C 0.13995(8) -0.1526(4) 0.53076(8) 0.0237(4) Uani 1 1 d . . .
C5 C 0.16931(9) -0.0182(4) 0.49225(9) 0.0274(4) Uani 1 1 d . . .
H5 H 0.2159(11) -0.012(6) 0.5150(13) 0.0407(18) Uiso 1 1 d . . .
C6 C 0.13186(9) 0.1153(5) 0.42092(9) 0.0295(4) Uani 1 1 d . . .
H6 H 0.1532(10) 0.209(6) 0.3953(12) 0.0407(18) Uiso 1 1 d . . .
C7 C 0.17802(8) -0.3000(4) 0.60540(9) 0.0249(4) Uani 1 1 d . . .
C8 C 0.15014(9) -0.4620(4) 0.64414(9) 0.0282(4) Uani 1 1 d . . .
H8 H 0.1863(10) -0.559(6) 0.6963(13) 0.0407(18) Uiso 1 1 d . . .
O9 O 0.09277(6) -0.5035(3) 0.62429(7) 0.0338(4) Uani 1 1 d . . .
C10 C 0.24683(8) -0.3048(5) 0.64732(9) 0.0284(4) Uani 1 1 d . . .
H10 H 0.2645(10) -0.440(6) 0.6986(13) 0.0407(18) Uiso 1 1 d . . .
O11 O 0.28571(6) -0.1753(3) 0.63191(7) 0.0353(4) Uani 1 1 d . . .
O12 O 0.0000 0.4476(5) 0.2500 0.0292(4) Uani 1 2 d S . .
H12 H 0.0313(10) 0.593(6) 0.2509(12) 0.0407(18) Uiso 1 1 d . . .
O13 O 0.09284(6) 0.8031(4) 0.24564(7) 0.0324(4) Uani 1 1 d . . .
H13A H 0.1351(11) 0.759(6) 0.2855(13) 0.0407(18) Uiso 1 1 d . . .
H13B H 0.0959(10) 0.680(6) 0.2062(13) 0.0407(18) 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
N1 0.0351(9) 0.0275(8) 0.0189(7) 0.0013(5) 0.0111(7) 0.0029(6)
C2 0.0297(10) 0.0315(10) 0.0216(9) -0.0020(6) 0.0100(8) 0.0009(7)
C3 0.0304(10) 0.0297(9) 0.0220(8) -0.0003(6) 0.0132(8) -0.0013(7)
C4 0.0281(9) 0.0217(8) 0.0186(8) -0.0030(6) 0.0102(7) 0.0008(6)
C5 0.0293(9) 0.0286(9) 0.0225(9) -0.0001(6) 0.0123(7) 0.0003(7)
C6 0.0363(10) 0.0293(9) 0.0239(9) -0.0005(6) 0.0164(8) -0.0006(7)
C7 0.0282(9) 0.0252(8) 0.0195(8) -0.0012(6) 0.0111(7) -0.0008(6)
C8 0.0344(10) 0.0277(9) 0.0211(8) -0.0006(6) 0.0134(8) 0.0011(7)
O9 0.0349(7) 0.0411(8) 0.0258(7) 0.0041(5) 0.0161(6) -0.0003(5)
C10 0.0316(10) 0.0298(9) 0.0204(8) -0.0014(6) 0.0112(7) -0.0002(7)
O11 0.0290(7) 0.0463(8) 0.0267(7) 0.0024(5) 0.0118(6) -0.0021(5)
O12 0.0287(9) 0.0364(10) 0.0203(8) 0.000 0.0112(7) 0.000
O13 0.0282(7) 0.0426(8) 0.0238(6) -0.0004(5) 0.0117(6) 0.0032(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
N1 C6 1.340(2) . ?
N1 C2 1.346(2) . ?
N1 H1 0.92(2) . ?
C2 C3 1.374(2) . ?
C2 H2 0.96(2) . ?
C3 C4 1.407(2) . ?
C3 H3 0.94(2) . ?
C4 C5 1.416(2) . ?
C4 C7 1.450(2) . ?
C5 C6 1.377(2) . ?
C5 H5 0.97(2) . ?
C6 H6 0.98(2) . ?
C7 C10 1.423(2) . ?
C7 C8 1.432(2) . ?
C8 O9 1.235(2) . ?
C8 H8 1.05(2) . ?
C10 O11 1.242(2) . ?
C10 H10 1.06(2) . ?
O12 H12 0.92(2) . ?
O13 H13A 0.94(2) . ?
O13 H13B 0.98(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
C6 N1 C2 121.23(15) . . ?
C6 N1 H1 120.5(13) . . ?
C2 N1 H1 118.1(13) . . ?
N1 C2 C3 120.45(17) . . ?
N1 C2 H2 117.8(14) . . ?
C3 C2 H2 121.7(14) . . ?
C2 C3 C4 120.84(16) . . ?
C2 C3 H3 117.8(14) . . ?
C4 C3 H3 121.4(14) . . ?
C3 C4 C5 116.38(15) . . ?
C3 C4 C7 122.00(15) . . ?
C5 C4 C7 121.62(15) . . ?
C6 C5 C4 120.35(16) . . ?
C6 C5 H5 117.8(14) . . ?
C4 C5 H5 121.9(13) . . ?
N1 C6 C5 120.74(16) . . ?
N1 C6 H6 120.2(13) . . ?
C5 C6 H6 119.1(13) . . ?
C10 C7 C8 112.95(14) . . ?
C10 C7 C4 123.67(15) . . ?
C8 C7 C4 123.37(15) . . ?
O9 C8 C7 129.86(16) . . ?
O9 C8 H8 119.4(11) . . ?
C7 C8 H8 110.7(11) . . ?
O11 C10 C7 129.56(16) . . ?
O11 C10 H10 119.3(11) . . ?
C7 C10 H10 111.1(11) . . ?
H13A O13 H13B 98.1(17) . . ?

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
N1 H1 O12 0.92(2) 1.83(2) 2.7425(17) 175(2) .
O12 H12 O13 0.92(2) 1.74(2) 2.6541(16) 170(2) .
O13 H13A O11 0.94(2) 1.82(2) 2.7592(18) 175.1(19) 7_556
O13 H13B O9 0.98(2) 1.80(2) 2.7786(18) 171(2) 6

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.089


