# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2002

data_struc

_database_code_CSD	176826


_journal_coden_Cambridge      440

_publ_requested_journal       'New Journal of Chemistry'

loop_
_publ_author_name
'Moutet, Jean-Claude'
'Pecaut, J.'
'Reynes, Olivier'
'Royal, Guy'
'Saint-Aman, Eric'


_publ_contact_author_name     	'Dr Jean-Claude Moutet'  
_publ_contact_author_address 
;
Laboratoire d'Electrochimie Organique et de Photochimie Rédox, UMR CNRS
5630
Université Joseph Fourier
BP 53
Grenoble Cedex 9
38041
FRANCE
;

_publ_contact_author_email       'JEAN-CLAUDE.MOUTET@UJF-GRENOBLE.FR'

_publ_section_title		
;
Ferrocenylmethyl)trimethylammonium cation: a very simple probe
for the electrochemical sensing of dihydrogenphosphate and ATP anions
;

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
'C16 H30 Fe N O6 P'
_chemical_formula_weight          419.23

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'
'P'  'P'   0.1023   0.0942
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Fe'  'Fe'   0.3463   0.8444
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P21/c

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                    17.024(5)
_cell_length_b                    13.573(3)
_cell_length_c                    8.4498(19)
_cell_angle_alpha                 90.00
_cell_angle_beta                  95.710(15)
_cell_angle_gamma                 90.00
_cell_volume                      1942.8(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     223(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.08
_exptl_crystal_size_mid           0.5
_exptl_crystal_size_min           0.5
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.433
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              888
_exptl_absorpt_coefficient_mu     0.889
_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       223(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   'CCD 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             12266
_diffrn_reflns_av_R_equivalents   0.0247
_diffrn_reflns_av_sigmaI/netI     0.0411
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_theta_min          1.92
_diffrn_reflns_theta_max          28.91
_reflns_number_total              4672
_reflns_number_gt                 3347
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'Bruker SMART'
_computing_cell_refinement        'Bruker SMART'
_computing_data_reduction         'Bruker SHELXTL'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'

_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^)+(0.0506P)^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_number_reflns          4672
_refine_ls_number_parameters      346
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0517
_refine_ls_R_factor_gt            0.0301
_refine_ls_wR_factor_ref          0.0882
_refine_ls_wR_factor_gt           0.0739
_refine_ls_goodness_of_fit_ref    0.996
_refine_ls_restrained_S_all       0.996
_refine_ls_shift/su_max           0.007
_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
Fe Fe 0.362302(16) 0.91460(2) 0.32706(3) 0.02726(10) Uani 1 1 d . . .
N N 0.13566(9) 1.06894(11) 0.18223(18) 0.0244(3) Uani 1 1 d . . .
C1 C 0.42149(14) 0.78669(17) 0.3827(3) 0.0418(6) Uani 1 1 d . . .
H1 H 0.4514(14) 0.7479(17) 0.312(3) 0.053(7) Uiso 1 1 d . . .
C2 C 0.33926(15) 0.77497(17) 0.3975(3) 0.0415(5) Uani 1 1 d . . .
H2 H 0.3038(14) 0.7321(17) 0.332(3) 0.049(7) Uiso 1 1 d . . .
C3 C 0.31797(14) 0.84339(18) 0.5115(3) 0.0416(6) Uani 1 1 d . . .
H3 H 0.2691(12) 0.8517(15) 0.545(2) 0.034(6) Uiso 1 1 d . . .
C4 C 0.38588(14) 0.89787(19) 0.5678(3) 0.0431(6) Uani 1 1 d . . .
H4 H 0.3863(12) 0.9501(17) 0.642(3) 0.036(6) Uiso 1 1 d . . .
C5 C 0.45002(14) 0.86277(19) 0.4878(3) 0.0421(6) Uani 1 1 d . . .
H5 H 0.4990(15) 0.8922(18) 0.497(3) 0.052(7) Uiso 1 1 d . . .
C6 C 0.40464(13) 1.02955(17) 0.2031(3) 0.0371(5) Uani 1 1 d . . .
H6 H 0.4534(13) 1.0563(17) 0.221(3) 0.046(7) Uiso 1 1 d . . .
C7 C 0.38160(12) 0.95056(17) 0.0989(3) 0.0351(5) Uani 1 1 d . . .
H7 H 0.4132(13) 0.9135(16) 0.036(3) 0.042(6) Uiso 1 1 d . . .
C8 C 0.30008(12) 0.93154(15) 0.1108(2) 0.0292(4) Uani 1 1 d . . .
H8 H 0.2695(13) 0.8816(17) 0.059(3) 0.037(6) Uiso 1 1 d . . .
C9 C 0.27342(11) 0.99838(14) 0.2236(2) 0.0258(4) Uani 1 1 d . . .
C10 C 0.33877(12) 1.05945(16) 0.2814(3) 0.0314(5) Uani 1 1 d . . .
H10 H 0.3333(11) 1.1061(14) 0.353(2) 0.020(5) Uiso 1 1 d . . .
C11 C 0.19250(11) 0.99917(16) 0.2774(2) 0.0282(4) Uani 1 1 d . . .
H11A H 0.1895(13) 1.0217(17) 0.386(3) 0.046(6) Uiso 1 1 d . . .
H11B H 0.1673(12) 0.9360(16) 0.258(2) 0.031(6) Uiso 1 1 d . . .
C12 C 0.16207(17) 1.17253(18) 0.2039(4) 0.0504(7) Uani 1 1 d . . .
H12A H 0.1622(13) 1.1866(17) 0.316(3) 0.043(7) Uiso 1 1 d . . .
H12B H 0.1251(13) 1.2113(17) 0.148(3) 0.038(6) Uiso 1 1 d . . .
H12C H 0.2122(15) 1.1797(18) 0.155(3) 0.056(8) Uiso 1 1 d . . .
C13 C 0.05577(13) 1.0582(2) 0.2389(3) 0.0399(6) Uani 1 1 d . . .
H13A H 0.0236(13) 1.1026(16) 0.176(3) 0.034(6) Uiso 1 1 d . . .
H13B H 0.0633(16) 1.0783(19) 0.345(3) 0.065(9) Uiso 1 1 d . . .
H13C H 0.0404(16) 0.989(2) 0.218(3) 0.070(9) Uiso 1 1 d . . .
C14 C 0.12997(15) 1.0439(2) 0.0100(3) 0.0394(5) Uani 1 1 d . . .
H14A H 0.0918(15) 1.0892(17) -0.044(3) 0.047(7) Uiso 1 1 d . . .
H14B H 0.1209(15) 0.978(2) 0.001(3) 0.057(8) Uiso 1 1 d . . .
H14C H 0.1825(17) 1.056(2) -0.022(3) 0.065(8) Uiso 1 1 d . . .
P P 0.92872(3) 0.28009(4) 0.98794(6) 0.02396(12) Uani 1 1 d . . .
O1 O 0.98083(12) 0.19935(15) 0.9177(2) 0.0552(6) Uani 1 1 d . . .
H1O H 0.9804(15) 0.195(2) 0.844(3) 0.044(9) Uiso 1 1 d . . .
O2 O 0.86172(10) 0.22247(14) 1.0623(2) 0.0430(5) Uani 1 1 d . . .
H2O H 0.8686(15) 0.206(2) 1.132(3) 0.045(9) Uiso 1 1 d . . .
O3 O 0.89163(8) 0.34353(9) 0.85601(15) 0.0292(3) Uani 1 1 d . . .
O4 O 0.98002(8) 0.33116(11) 1.11872(15) 0.0346(3) Uani 1 1 d . . .
O5 O 0.88106(10) 0.55115(15) 0.8597(2) 0.0391(4) Uani 1 1 d . . .
H1O5 H 0.8866(16) 0.496(2) 0.872(3) 0.065(10) Uiso 1 1 d . . .
H2O5 H 0.9213(17) 0.5815(19) 0.870(3) 0.050(8) Uiso 1 1 d . . .
O6 O 0.73270(12) 0.63815(14) 0.8557(2) 0.0578(5) Uani 1 1 d . . .
H6O H 0.777(2) 0.615(3) 0.849(4) 0.103(14) Uiso 1 1 d . . .
C15 C 0.69045(16) 0.6378(2) 0.7024(4) 0.0559(7) Uani 1 1 d . . .
H15A H 0.6932(15) 0.5733(19) 0.665(3) 0.052(7) Uiso 1 1 d . . .
H15B H 0.7193(16) 0.681(2) 0.628(3) 0.074(9) Uiso 1 1 d . . .
C16 C 0.60797(19) 0.6694(3) 0.7130(6) 0.0698(9) Uani 1 1 d . . .
H16A H 0.581(2) 0.682(3) 0.602(5) 0.120(15) Uiso 1 1 d . . .
H16B H 0.6088(17) 0.736(2) 0.767(3) 0.078(9) Uiso 1 1 d . . .
H16C H 0.5813(18) 0.626(2) 0.760(4) 0.077(10) 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
Fe 0.02311(15) 0.02922(17) 0.02853(17) 0.00211(12) -0.00199(11) 0.00143(12)
N 0.0224(8) 0.0252(9) 0.0252(8) 0.0017(7) 0.0004(6) 0.0013(6)
C1 0.0429(14) 0.0370(13) 0.0448(14) 0.0093(11) 0.0010(11) 0.0134(10)
C2 0.0464(14) 0.0368(13) 0.0398(13) 0.0112(10) -0.0031(11) -0.0035(10)
C3 0.0346(13) 0.0523(15) 0.0378(13) 0.0153(11) 0.0036(10) 0.0030(11)
C4 0.0492(15) 0.0492(16) 0.0291(12) 0.0048(11) -0.0059(10) 0.0046(11)
C5 0.0291(12) 0.0512(15) 0.0434(13) 0.0101(11) -0.0099(10) 0.0041(10)
C6 0.0248(11) 0.0402(13) 0.0453(13) 0.0096(10) -0.0010(10) -0.0060(9)
C7 0.0312(11) 0.0414(12) 0.0334(12) 0.0031(10) 0.0071(9) 0.0039(9)
C8 0.0296(11) 0.0298(11) 0.0272(11) 0.0005(8) -0.0023(8) 0.0022(8)
C9 0.0229(10) 0.0279(10) 0.0257(10) 0.0022(8) -0.0022(8) 0.0015(8)
C10 0.0316(11) 0.0274(11) 0.0340(12) -0.0012(9) -0.0028(9) -0.0004(8)
C11 0.0259(11) 0.0325(12) 0.0257(11) 0.0052(9) 0.0002(8) 0.0038(9)
C12 0.0445(15) 0.0267(13) 0.077(2) -0.0031(13) -0.0099(15) 0.0031(11)
C13 0.0265(11) 0.0537(16) 0.0404(14) 0.0117(12) 0.0081(10) 0.0102(11)
C14 0.0350(13) 0.0583(17) 0.0240(11) 0.0012(11) -0.0020(10) 0.0130(12)
P 0.0275(3) 0.0251(3) 0.0189(2) 0.00035(19) 0.00061(19) 0.00157(19)
O1 0.0814(14) 0.0621(12) 0.0212(9) 0.0020(8) 0.0011(9) 0.0455(10)
O2 0.0421(10) 0.0562(11) 0.0282(9) 0.0122(8) -0.0089(7) -0.0213(8)
O3 0.0362(8) 0.0282(7) 0.0230(7) 0.0013(6) 0.0013(6) 0.0081(6)
O4 0.0382(8) 0.0416(9) 0.0232(7) 0.0011(6) -0.0007(6) -0.0156(7)
O5 0.0370(10) 0.0360(10) 0.0443(10) 0.0033(8) 0.0036(7) -0.0004(8)
O6 0.0589(13) 0.0594(12) 0.0570(12) 0.0039(9) 0.0150(10) 0.0074(10)
C15 0.0439(15) 0.0594(19) 0.0658(19) -0.0194(15) 0.0113(14) -0.0060(13)
C16 0.0493(18) 0.057(2) 0.106(3) 0.005(2) 0.0195(19) 0.0028(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
Fe C9 2.0209(19) . ?
Fe C8 2.032(2) . ?
Fe C10 2.036(2) . ?
Fe C2 2.036(2) . ?
Fe C1 2.039(2) . ?
Fe C5 2.041(2) . ?
Fe C3 2.041(2) . ?
Fe C4 2.046(2) . ?
Fe C7 2.047(2) . ?
Fe C6 2.050(2) . ?
N C12 1.482(3) . ?
N C14 1.488(3) . ?
N C13 1.493(3) . ?
N C11 1.525(2) . ?
C1 C5 1.416(3) . ?
C1 C2 1.427(3) . ?
C2 C3 1.411(3) . ?
C3 C4 1.414(3) . ?
C4 C5 1.422(3) . ?
C6 C10 1.417(3) . ?
C6 C7 1.418(3) . ?
C7 C8 1.425(3) . ?
C8 C9 1.423(3) . ?
C9 C10 1.434(3) . ?
C9 C11 1.493(3) . ?
P O3 1.4977(14) . ?
P O4 1.5075(14) . ?
P O1 1.5636(18) . ?
P O2 1.5652(17) . ?
O6 C15 1.418(3) . ?
C15 C16 1.479(4) . ?

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
C9 Fe C8 41.10(8) . . ?
C9 Fe C10 41.39(8) . . ?
C8 Fe C10 69.21(8) . . ?
C9 Fe C2 119.50(9) . . ?
C8 Fe C2 105.65(9) . . ?
C10 Fe C2 156.11(9) . . ?
C9 Fe C1 155.58(9) . . ?
C8 Fe C1 120.34(9) . . ?
C10 Fe C1 161.73(9) . . ?
C2 Fe C1 40.99(10) . . ?
C9 Fe C5 161.55(9) . . ?
C8 Fe C5 156.76(9) . . ?
C10 Fe C5 125.18(10) . . ?
C2 Fe C5 68.54(10) . . ?
C1 Fe C5 40.62(10) . . ?
C9 Fe C3 106.20(9) . . ?
C8 Fe C3 122.75(9) . . ?
C10 Fe C3 121.42(9) . . ?
C2 Fe C3 40.49(9) . . ?
C1 Fe C3 68.44(10) . . ?
C5 Fe C3 68.30(10) . . ?
C9 Fe C4 123.84(9) . . ?
C8 Fe C4 159.99(9) . . ?
C10 Fe C4 108.13(10) . . ?
C2 Fe C4 68.32(10) . . ?
C1 Fe C4 68.45(10) . . ?
C5 Fe C4 40.72(10) . . ?
C3 Fe C4 40.48(9) . . ?
C9 Fe C7 69.00(8) . . ?
C8 Fe C7 40.89(8) . . ?
C10 Fe C7 68.78(9) . . ?
C2 Fe C7 123.43(10) . . ?
C1 Fe C7 107.35(10) . . ?
C5 Fe C7 122.26(9) . . ?
C3 Fe C7 159.77(10) . . ?
C4 Fe C7 158.24(10) . . ?
C9 Fe C6 68.71(8) . . ?
C8 Fe C6 68.45(9) . . ?
C10 Fe C6 40.57(9) . . ?
C2 Fe C6 161.02(10) . . ?
C1 Fe C6 125.11(9) . . ?
C5 Fe C6 109.34(10) . . ?
C3 Fe C6 157.83(10) . . ?
C4 Fe C6 123.24(10) . . ?
C7 Fe C6 40.50(9) . . ?
C12 N C14 109.1(2) . . ?
C12 N C13 109.13(19) . . ?
C14 N C13 108.58(18) . . ?
C12 N C11 110.81(17) . . ?
C14 N C11 110.48(16) . . ?
C13 N C11 108.72(15) . . ?
C5 C1 C2 107.7(2) . . ?
C5 C1 Fe 69.79(13) . . ?
C2 C1 Fe 69.42(13) . . ?
C3 C2 C1 107.9(2) . . ?
C3 C2 Fe 69.94(13) . . ?
C1 C2 Fe 69.59(13) . . ?
C2 C3 C4 108.5(2) . . ?
C2 C3 Fe 69.56(13) . . ?
C4 C3 Fe 69.94(13) . . ?
C3 C4 C5 107.8(2) . . ?
C3 C4 Fe 69.57(13) . . ?
C5 C4 Fe 69.46(13) . . ?
C1 C5 C4 108.1(2) . . ?
C1 C5 Fe 69.59(13) . . ?
C4 C5 Fe 69.83(13) . . ?
C10 C6 C7 108.88(19) . . ?
C10 C6 Fe 69.19(12) . . ?
C7 C6 Fe 69.65(13) . . ?
C6 C7 C8 107.73(19) . . ?
C6 C7 Fe 69.85(13) . . ?
C8 C7 Fe 69.01(12) . . ?
C9 C8 C7 108.03(18) . . ?
C9 C8 Fe 69.02(11) . . ?
C7 C8 Fe 70.10(12) . . ?
C8 C9 C10 107.96(17) . . ?
C8 C9 C11 125.04(18) . . ?
C10 C9 C11 126.90(19) . . ?
C8 C9 Fe 69.88(11) . . ?
C10 C9 Fe 69.86(11) . . ?
C11 C9 Fe 123.10(13) . . ?
C6 C10 C9 107.40(19) . . ?
C6 C10 Fe 70.24(12) . . ?
C9 C10 Fe 68.75(11) . . ?
C9 C11 N 113.60(16) . . ?
O3 P O4 116.87(9) . . ?
O3 P O1 109.48(9) . . ?
O4 P O1 106.94(10) . . ?
O3 P O2 108.41(9) . . ?
O4 P O2 109.13(9) . . ?
O1 P O2 105.42(12) . . ?
O6 C15 C16 110.0(3) . . ?

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
O1 H1O O4  0.63(2) 1.93(2) 2.559(2) 174(3) 4_565
O2 H2O O3  0.63(2) 2.01(3) 2.640(2) 179(4) 4_566
O5 H1O5 O3  0.76(3) 2.07(3) 2.824(2) 168(3) .
O5 H2O5 O4  0.80(3) 2.05(3) 2.845(2) 174(3) 3_767
O6 H6O O5  0.83(3) 1.96(3) 2.785(3) 172(4) .
C14 H14A O1  0.98(2) 2.41(3) 3.334(3) 158.9(19) 1_464

_diffrn_measured_fraction_theta_max    0.911
_diffrn_reflns_theta_full              28.91
_diffrn_measured_fraction_theta_full   0.911
_refine_diff_density_max    0.345
_refine_diff_density_min   -0.342
_refine_diff_density_rms    0.088