# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 2001
# CCDC Number: 182/1846

##############################################################################
#
# Ref. B007822K
#
#
# Variable Temperature Electrochemistry as a Powerful Method for
# Conformational Investigations on the Fluxional Organometallic Complex
# Mo(His-N-C2H4-CO2Me)(eta-allyl)(CO)2; (His: N,N,O-L-Histidinate)
#
# D.R. van Staveren, E. Bothe T. Weyhermuller, N. Metzler-Nolte
#
#
#
##############################################################################
 

data_2 #(ST33339
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      '[C15 H19 Mo N3 O6], 2 CH3OH' 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C17 H27 Mo N3 O8' 
_chemical_formula_weight          497.36 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
 
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' 
 'Mo'  'Mo'  -1.6832   0.6857 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            'Monoclinic'
_symmetry_space_group_name_H-M    'P2(1)' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    12.0928(14) 
_cell_length_b                    7.5347(8) 
_cell_length_c                    12.1177(14) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  101.59(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1081.6(2) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     5092 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        'transparent block' 
_exptl_crystal_colour             'yellow' 
_exptl_crystal_size_max           0.70 
_exptl_crystal_size_mid           0.42 
_exptl_crystal_size_min           0.35 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.527 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              512 
_exptl_absorpt_coefficient_mu     0.653 
_exptl_absorpt_correction_type    'Not measured' 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(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        'Siemens SMART CCD-Detector' 
_diffrn_measurement_method        '\w-scan, 0.3 deg./frame' 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             11346 
_diffrn_reflns_av_R_equivalents   0.0509 
_diffrn_reflns_av_sigmaI/netI     0.0354 
_diffrn_reflns_limit_h_min        -18 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -4 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.17 
_diffrn_reflns_theta_max          32.50 
_reflns_number_total              4668 
_reflns_number_observed           4539 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        'Siemens SAINT 5' 
_computing_cell_refinement        'Siemens SAINT 5' 
_computing_data_reduction         'Siemens SAINT 5' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.5477P] 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     ? 
_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(3) 
_refine_ls_number_reflns          4668 
_refine_ls_number_parameters      281 
_refine_ls_number_restraints      7 
_refine_ls_R_factor_all           0.0281 
_refine_ls_R_factor_obs           0.0269 
_refine_ls_wR_factor_all          0.0692 
_refine_ls_wR_factor_obs          0.0685 
_refine_ls_goodness_of_fit_all    1.030 
_refine_ls_goodness_of_fit_obs    1.035 
_refine_ls_restrained_S_all       1.029 
_refine_ls_restrained_S_obs       1.034 
_refine_ls_shift/esd_max          0.002 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
Mo1 Mo 0.394500(12) 0.56786(4) 0.727848(11) 0.01272(5) Uani 1 d . . 
O2 O -0.1904(2) 0.2381(3) 0.7356(2) 0.0293(4) Uani 1 d . . 
O3 O -0.0831(2) 0.2409(3) 0.6039(2) 0.0318(5) Uani 1 d . . 
O13 O 0.34356(15) 0.3699(3) 1.04121(14) 0.0200(3) Uani 1 d . . 
O14 O 0.3852(2) 0.3886(3) 0.8704(2) 0.0170(4) Uani 1 d . . 
N6 N 0.0318(2) 0.6277(3) 0.6825(2) 0.0171(4) Uani 1 d . . 
N8 N 0.2169(2) 0.6184(3) 0.74057(15) 0.0149(3) Uani 1 d . . 
N12 N 0.4154(2) 0.7423(4) 0.8819(2) 0.0154(4) Uani 1 d . . 
H12A H 0.4909(2) 0.7567(4) 0.9123(2) 0.019 Uiso 1 calc R . 
H12B H 0.3848(2) 0.8523(4) 0.8622(2) 0.019 Uiso 1 calc R . 
C1 C -0.1829(3) 0.0481(7) 0.7405(3) 0.0417(9) Uani 1 d . . 
H1A H -0.2231(3) 0.0037(7) 0.7975(3) 0.062 Uiso 1 calc R . 
H1B H -0.1034(3) 0.0126(7) 0.7605(3) 0.062 Uiso 1 calc R . 
H1C H -0.2171(3) -0.0018(7) 0.6668(3) 0.062 Uiso 1 calc R . 
C3 C -0.1390(2) 0.3172(4) 0.6609(2) 0.0233(5) Uani 1 d . . 
C4 C -0.1636(2) 0.5139(4) 0.6567(2) 0.0221(5) Uani 1 d . . 
H4A H -0.1627(2) 0.5570(4) 0.7340(2) 0.027 Uiso 1 calc R . 
H4B H -0.2403(2) 0.5341(4) 0.6114(2) 0.027 Uiso 1 calc R . 
C5 C -0.0795(2) 0.6204(4) 0.6066(2) 0.0227(5) Uani 1 d . . 
H5A H -0.0715(2) 0.5661(4) 0.5342(2) 0.027 Uiso 1 calc R . 
H5B H -0.1085(2) 0.7426(4) 0.5909(2) 0.027 Uiso 1 calc R . 
C7 C 0.1309(2) 0.5960(3) 0.6532(2) 0.0154(5) Uani 1 d . . 
H7 H 0.1391(2) 0.5620(3) 0.5798(2) 0.018 Uiso 1 calc R . 
C9 C 0.1680(2) 0.6686(3) 0.8306(2) 0.0147(4) Uani 1 d . . 
C10 C 0.0537(2) 0.6747(4) 0.7951(2) 0.0173(4) Uani 1 d . . 
H10 H -0.0003(2) 0.7053(4) 0.8391(2) 0.021 Uiso 1 calc R . 
C11 C 0.2346(2) 0.7178(4) 0.9456(2) 0.0164(4) Uani 1 d . . 
H11A H 0.1981(2) 0.6633(4) 1.0036(2) 0.020 Uiso 1 calc R . 
H11B H 0.2317(2) 0.8482(4) 0.9547(2) 0.020 Uiso 1 calc R . 
C12 C 0.3579(2) 0.6596(4) 0.9665(2) 0.0154(5) Uani 1 d . . 
H12 H 0.3964(2) 0.6986(4) 1.0436(2) 0.018 Uiso 1 calc R . 
C13 C 0.3627(2) 0.4578(4) 0.9600(2) 0.0144(5) Uani 1 d . . 
C15 C 0.3795(2) 0.7423(5) 0.6074(2) 0.0195(6) Uani 1 d . . 
O15 O 0.3684(2) 0.8430(4) 0.5338(2) 0.0338(5) Uani 1 d . . 
C16 C 0.3469(2) 0.4197(5) 0.5954(2) 0.0198(5) Uani 1 d . . 
O16 O 0.3173(2) 0.3394(4) 0.5124(2) 0.0284(5) Uani 1 d . . 
C17 C 0.5357(2) 0.3649(4) 0.7123(2) 0.0231(5) Uani 1 d D . 
H17A H 0.5426(30) 0.3574(62) 0.6382(18) 0.030 Uiso 1 d D . 
H17B H 0.5343(32) 0.2569(36) 0.7476(29) 0.030 Uiso 1 d D . 
C18 C 0.5781(2) 0.5186(4) 0.7734(2) 0.0195(5) Uani 1 d . . 
H18 H 0.6016(27) 0.5177(53) 0.8556(27) 0.025 Uiso 1 d . . 
C19 C 0.5704(2) 0.6796(4) 0.7131(2) 0.0218(5) Uani 1 d D . 
H19A H 0.5776(31) 0.6794(61) 0.6389(18) 0.028 Uiso 1 d D . 
H19B H 0.5866(31) 0.7829(39) 0.7536(28) 0.028 Uiso 1 d D . 
C20 C 0.2079(3) 0.0847(5) 0.7058(2) 0.0297(6) Uani 1 d . . 
H20A H 0.1542(18) -0.0142(26) 0.6978(16) 0.045 Uiso 1 calc R . 
H20B H 0.2454(4) 0.0860(49) 0.6413(3) 0.045 Uiso 1 calc R . 
H20C H 0.1675(21) 0.1968(24) 0.7086(13) 0.045 Uiso 1 calc R . 
O20 O 0.2901(2) 0.0633(5) 0.8072(2) 0.0301(4) Uani 1 d . . 
H20 H 0.3203(28) 0.1618(12) 0.8268(21) 0.045 Uiso 1 calc R . 
O30 O 0.1428(2) 0.1981(6) 1.0596(2) 0.0511(9) Uani 1 d . . 
H30 H 0.2062(19) 0.2394(85) 1.0548(8) 0.077 Uiso 1 calc R . 
C30 C 0.0733(3) 0.1922(7) 0.9522(3) 0.0419(9) Uani 1 d . . 
H30A H -0.0005(10) 0.1432(40) 0.9576(5) 0.063 Uiso 1 calc R . 
H30B H 0.1083(14) 0.1169(35) 0.9028(8) 0.063 Uiso 1 calc R . 
H30C H 0.0635(22) 0.3125(9) 0.9209(11) 0.063 Uiso 1 calc R . 
 
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 
Mo1 0.01035(7) 0.01895(8) 0.00961(7) -0.00020(9) 0.00382(4) 0.00025(9) 
O2 0.0318(10) 0.0311(11) 0.0259(9) -0.0047(9) 0.0083(8) -0.0033(9) 
O3 0.0286(10) 0.0375(13) 0.0308(10) -0.0097(10) 0.0095(8) 0.0056(10) 
O13 0.0188(8) 0.0267(9) 0.0153(7) 0.0069(7) 0.0055(6) 0.0005(7) 
O14 0.0187(9) 0.0175(9) 0.0161(8) -0.0007(7) 0.0068(7) 0.0003(7) 
N6 0.0115(7) 0.0258(9) 0.0136(8) 0.0008(7) 0.0020(6) 0.0016(7) 
N8 0.0135(7) 0.0204(9) 0.0118(7) -0.0001(7) 0.0048(6) -0.0007(6) 
N12 0.0134(9) 0.0180(10) 0.0153(9) -0.0007(8) 0.0037(7) -0.0017(8) 
C1 0.051(2) 0.039(3) 0.0337(13) -0.002(2) 0.0046(12) -0.008(2) 
C3 0.0160(10) 0.0322(14) 0.0204(10) -0.0059(11) 0.0009(8) 0.0008(10) 
C4 0.0117(9) 0.0307(12) 0.0238(10) -0.0062(10) 0.0032(7) 0.0003(9) 
C5 0.0125(9) 0.0344(14) 0.0195(10) 0.0002(9) -0.0010(7) 0.0028(9) 
C7 0.0127(7) 0.0208(15) 0.0132(7) -0.0002(8) 0.0039(6) 0.0004(8) 
C9 0.0139(9) 0.0194(10) 0.0117(8) 0.0013(8) 0.0046(7) 0.0024(8) 
C10 0.0148(9) 0.0252(11) 0.0134(9) 0.0000(8) 0.0063(7) 0.0030(8) 
C11 0.0143(9) 0.0243(11) 0.0116(8) -0.0020(8) 0.0048(7) 0.0014(8) 
C12 0.0142(11) 0.0223(13) 0.0101(10) -0.0009(9) 0.0035(8) -0.0011(9) 
C13 0.0082(10) 0.0202(12) 0.0142(11) 0.0031(10) 0.0007(8) -0.0006(9) 
C15 0.0150(12) 0.0304(14) 0.0151(10) 0.0037(10) 0.0080(9) 0.0039(11) 
O15 0.0312(11) 0.0482(15) 0.0250(10) 0.0185(10) 0.0127(8) 0.0104(11) 
C16 0.0138(12) 0.0288(13) 0.0177(11) -0.0012(10) 0.0052(8) 0.0020(10) 
O16 0.0251(10) 0.0410(13) 0.0189(8) -0.0118(9) 0.0041(7) -0.0007(9) 
C17 0.0191(11) 0.0332(15) 0.0183(11) -0.0003(10) 0.0068(8) 0.0086(11) 
C18 0.0105(8) 0.0314(13) 0.0173(9) 0.0015(9) 0.0046(7) 0.0030(8) 
C19 0.0128(10) 0.0344(14) 0.0196(11) 0.0016(11) 0.0067(8) -0.0035(10) 
C20 0.0378(13) 0.0199(15) 0.0308(11) 0.0015(13) 0.0052(9) -0.0018(13) 
O20 0.0370(9) 0.0160(7) 0.0345(8) -0.0005(13) 0.0008(7) -0.0034(14) 
O30 0.0305(11) 0.098(3) 0.0277(11) -0.0005(14) 0.0118(9) -0.0260(15) 
C30 0.031(2) 0.065(3) 0.0302(15) -0.005(2) 0.0092(12) 0.003(2) 
 
_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 
Mo1 C16 1.944(3) . ? 
Mo1 C15 1.945(3) . ? 
Mo1 C18 2.209(2) . ? 
Mo1 O14 2.214(2) . ? 
Mo1 N8 2.216(2) . ? 
Mo1 N12 2.256(2) . ? 
Mo1 C17 2.328(3) . ? 
Mo1 C19 2.328(3) . ? 
O2 C3 1.336(4) . ? 
O2 C1 1.435(6) . ? 
O3 C3 1.205(3) . ? 
O13 C13 1.246(3) . ? 
O14 C13 1.282(4) . ? 
N6 C7 1.338(3) . ? 
N6 C10 1.384(3) . ? 
N6 C5 1.470(3) . ? 
N8 C7 1.338(3) . ? 
N8 C9 1.394(3) . ? 
N12 C12 1.486(4) . ? 
C3 C4 1.510(4) . ? 
C4 C5 1.515(4) . ? 
C9 C10 1.363(3) . ? 
C9 C11 1.509(3) . ? 
C11 C12 1.527(4) . ? 
C12 C13 1.524(3) . ? 
C15 O15 1.159(4) . ? 
C16 O16 1.167(4) . ? 
C17 C18 1.414(4) . ? 
C18 C19 1.410(4) . ? 
C20 O20 1.426(3) . ? 
O30 C30 1.400(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 
C16 Mo1 C15 78.54(13) . . ? 
C16 Mo1 C18 103.07(11) . . ? 
C15 Mo1 C18 103.82(11) . . ? 
C16 Mo1 O14 103.93(11) . . ? 
C15 Mo1 O14 170.45(10) . . ? 
C18 Mo1 O14 84.74(9) . . ? 
C16 Mo1 N8 91.46(10) . . ? 
C15 Mo1 N8 89.45(10) . . ? 
C18 Mo1 N8 161.91(8) . . ? 
O14 Mo1 N8 81.30(7) . . ? 
C16 Mo1 N12 169.40(9) . . ? 
C15 Mo1 N12 101.85(12) . . ? 
C18 Mo1 N12 87.19(9) . . ? 
O14 Mo1 N12 74.00(7) . . ? 
N8 Mo1 N12 77.97(8) . . ? 
C16 Mo1 C17 69.91(11) . . ? 
C15 Mo1 C17 110.05(11) . . ? 
C18 Mo1 C17 36.21(10) . . ? 
O14 Mo1 C17 79.35(9) . . ? 
N8 Mo1 C17 148.76(10) . . ? 
N12 Mo1 C17 119.18(9) . . ? 
C16 Mo1 C19 105.54(11) . . ? 
C15 Mo1 C19 69.34(11) . . ? 
C18 Mo1 C19 36.08(11) . . ? 
O14 Mo1 C19 118.10(9) . . ? 
N8 Mo1 C19 148.91(10) . . ? 
N12 Mo1 C19 84.29(10) . . ? 
C17 Mo1 C19 62.29(12) . . ? 
C3 O2 C1 116.0(3) . . ? 
C13 O14 Mo1 117.7(2) . . ? 
C7 N6 C10 107.6(2) . . ? 
C7 N6 C5 125.7(2) . . ? 
C10 N6 C5 126.6(2) . . ? 
C7 N8 C9 105.6(2) . . ? 
C7 N8 Mo1 122.28(14) . . ? 
C9 N8 Mo1 132.11(14) . . ? 
C12 N12 Mo1 109.7(2) . . ? 
O3 C3 O2 124.5(3) . . ? 
O3 C3 C4 125.3(3) . . ? 
O2 C3 C4 110.2(2) . . ? 
C3 C4 C5 113.0(2) . . ? 
N6 C5 C4 111.9(2) . . ? 
N6 C7 N8 111.4(2) . . ? 
C10 C9 N8 109.0(2) . . ? 
C10 C9 C11 127.0(2) . . ? 
N8 C9 C11 123.9(2) . . ? 
C9 C10 N6 106.5(2) . . ? 
C9 C11 C12 113.9(2) . . ? 
N12 C12 C13 110.8(3) . . ? 
N12 C12 C11 110.0(2) . . ? 
C13 C12 C11 108.9(3) . . ? 
O13 C13 O14 123.9(3) . . ? 
O13 C13 C12 118.3(3) . . ? 
O14 C13 C12 117.8(3) . . ? 
O15 C15 Mo1 178.1(3) . . ? 
O16 C16 Mo1 176.2(3) . . ? 
C18 C17 Mo1 67.34(14) . . ? 
C19 C18 C17 117.0(2) . . ? 
C19 C18 Mo1 76.54(14) . . ? 
C17 C18 Mo1 76.45(14) . . ? 
C18 C19 Mo1 67.38(14) . . ? 
 
_refine_diff_density_max    1.066 
_refine_diff_density_min   -0.721 
_refine_diff_density_rms    0.088 

#===END