# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 182/1330

data_shelx93 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C19 H14 Cl2 Mo N2 O5' 
_chemical_formula_weight          517.16 
_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 
 'Mo'  'Mo'  -1.6832   0.6857 
 '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' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'C'  'C'   0.0033   0.0016 
 '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' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            ? 
_symmetry_space_group_name_H-M    ? 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    9.7912(10) 
_cell_length_b                    10.6430(10) 
_cell_length_c                    10.9638(10) 
_cell_angle_alpha                 117.700(10) 
_cell_angle_beta                  90.140(10) 
_cell_angle_gamma                 105.080(10) 
_cell_volume                      966.5(2) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.777 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              516 
_exptl_absorpt_coefficient_mu     0.990 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71093 
_diffrn_radiation_type            MoKa  
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        ? 
_diffrn_measurement_method        ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             3552 
_diffrn_reflns_av_R_equivalents   0.0483 
_diffrn_reflns_av_sigmaI/netI     0.0206 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          2.12 
_diffrn_reflns_theta_max          24.98 
_reflns_number_total              3359 
_reflns_number_observed           3006 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_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^)+( 0.0935P)^2^+0.4574P] 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_number_reflns          3359 
_refine_ls_number_parameters      268 
_refine_ls_number_restraints      10 
_refine_ls_R_factor_all           0.0478 
_refine_ls_R_factor_obs           0.0414 
_refine_ls_wR_factor_all          0.1235 
_refine_ls_wR_factor_obs          0.1190 
_refine_ls_goodness_of_fit_all    1.099 
_refine_ls_goodness_of_fit_obs    1.124 
_refine_ls_restrained_S_all       1.136 
_refine_ls_restrained_S_obs       1.166 
_refine_ls_shift/esd_max          -0.025 
_refine_ls_shift/esd_mean         0.001 
 
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 
Cl1 Cl 0.4090(4) -0.2361(4) -0.0846(3) 0.1062(8) Uiso 0.75 d PD 1 
Cl2 Cl 0.5449(5) -0.4587(5) -0.2096(5) 0.0905(11) Uiso 0.45 d PD 1 
Cl3 Cl 0.4867(14) -0.4814(12) -0.0941(11) 0.090(2) Uiso 0.20 d PD 2 
Cl4 Cl 0.3986(23) -0.5032(20) -0.0866(18) 0.086(4) Uiso 0.10 d PD 3 
Cl5 Cl 0.3643(12) -0.2894(12) -0.0550(11) 0.112(3) Uiso 0.25 d PD 4 
Cl6 Cl 0.5462(9) -0.4703(9) -0.1375(10) 0.090(2) Uiso 0.25 d PD 4 
C19 C 0.4010(12) -0.4245(10) -0.1895(10) 0.141(4) Uani 1 d D . 
Mo Mo 0.16247(3) 0.18294(3) 0.43041(3) 0.0339(2) Uani 1 d . . 
O1 O 0.3671(3) 0.3094(3) 0.4556(3) 0.0369(6) Uani 1 d . . 
O2 O 0.0916(3) 0.3379(3) 0.4208(3) 0.0422(6) Uani 1 d . . 
O3 O 0.2062(3) 0.1897(3) 0.6057(3) 0.0457(7) Uani 1 d . . 
O4 O 0.1253(4) 0.2895(4) 0.6182(3) 0.0507(7) Uani 1 d . . 
O5 O 0.0201(3) 0.0299(4) 0.3546(3) 0.0485(7) Uani 1 d . . 
N1 N 0.2912(3) 0.0281(3) 0.3708(3) 0.0342(7) Uani 1 d . . 
N2 N 0.1786(3) 0.1437(4) 0.2098(3) 0.0366(7) Uani 1 d . . 
C1 C 0.2441(5) -0.1176(5) 0.3248(5) 0.0473(10) Uani 1 d . . 
H1 H 0.1471 -0.1621 0.3181 0.059 Uiso 1 calc . . 
C2 C 0.3370(6) -0.2054(5) 0.2863(5) 0.0531(11) Uani 1 d . . 
H2 H 0.3013 -0.3074 0.2520 0.042 Uiso 1 calc . . 
C3 C 0.4804(6) -0.1409(5) 0.2992(5) 0.0509(11) Uani 1 d . . 
H3 H 0.5425 -0.1990 0.2749 0.066 Uiso 1 calc . . 
C4 C 0.5342(5) 0.0129(5) 0.3490(4) 0.0399(9) Uani 1 d . . 
C5 C 0.6801(5) 0.0946(6) 0.3701(5) 0.0495(11) Uani 1 d . . 
H5 H 0.7503 0.0463 0.3504 0.053 Uiso 1 calc . . 
C6 C 0.7163(4) 0.2425(6) 0.4188(5) 0.0524(11) Uani 1 d . . 
H6 H 0.8125 0.2941 0.4324 0.079 Uiso 1 calc . . 
C7 C 0.6157(4) 0.3234(5) 0.4502(5) 0.0438(9) Uani 1 d . . 
H7 H 0.6453 0.4254 0.4832 0.052 Uiso 1 calc . . 
C8 C 0.4734(4) 0.2489(4) 0.4314(4) 0.0338(8) Uani 1 d . . 
C9 C 0.4339(4) 0.0932(4) 0.3824(4) 0.0333(8) Uani 1 d . . 
C10 C 0.2228(5) 0.0422(5) 0.1042(5) 0.0480(10) Uani 1 d . . 
H10 H 0.2583 -0.0234 0.1189 0.038 Uiso 1 calc . . 
C11 C 0.2176(6) 0.0313(6) -0.0284(5) 0.0558(11) Uani 1 d . . 
H11 H 0.2486 -0.0413 -0.1000 0.082 Uiso 1 calc . . 
C12 C 0.1674(5) 0.1264(6) -0.0522(5) 0.0545(12) Uani 1 d . . 
H12 H 0.1655 0.1206 -0.1395 0.105 Uiso 1 calc . . 
C13 C 0.1185(5) 0.2331(5) 0.0556(5) 0.0470(10) Uani 1 d . . 
C14 C 0.0605(6) 0.3344(7) 0.0422(6) 0.0614(13) Uani 1 d . . 
H14 H 0.0557 0.3355 -0.0420 0.044 Uiso 1 calc . . 
C15 C 0.0112(6) 0.4311(7) 0.1525(6) 0.0639(14) Uani 1 d . . 
H15 H -0.0298 0.4951 0.1409 0.061 Uiso 1 calc . . 
C16 C 0.0205(5) 0.4372(6) 0.2850(6) 0.0541(11) Uani 1 d . . 
H16 H -0.0121 0.5053 0.3595 0.084 Uiso 1 calc . . 
C17 C 0.0787(4) 0.3403(5) 0.2997(4) 0.0394(9) Uani 1 d . . 
C18 C 0.1265(4) 0.2379(5) 0.1861(4) 0.0389(8) Uani 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 
C19 0.179(11) 0.100(6) 0.117(7) 0.028(5) -0.051(7) 0.046(7) 
Mo 0.0245(2) 0.0387(2) 0.0426(2) 0.0213(2) 0.00675(14) 0.01247(15) 
O1 0.0272(13) 0.0329(13) 0.052(2) 0.0207(12) 0.0060(11) 0.0117(10) 
O2 0.038(2) 0.052(2) 0.047(2) 0.0256(14) 0.0123(12) 0.0271(13) 
O3 0.045(2) 0.055(2) 0.051(2) 0.0313(14) 0.0105(13) 0.0238(14) 
O4 0.055(2) 0.060(2) 0.049(2) 0.027(2) 0.0157(14) 0.034(2) 
O5 0.0302(15) 0.056(2) 0.059(2) 0.031(2) 0.0051(13) 0.0067(13) 
N1 0.029(2) 0.030(2) 0.043(2) 0.0176(13) 0.0040(13) 0.0095(12) 
N2 0.029(2) 0.037(2) 0.041(2) 0.0166(14) 0.0048(13) 0.0096(13) 
C1 0.049(2) 0.036(2) 0.053(2) 0.020(2) 0.001(2) 0.009(2) 
C2 0.073(3) 0.032(2) 0.051(2) 0.014(2) 0.007(2) 0.022(2) 
C3 0.064(3) 0.050(2) 0.046(2) 0.019(2) 0.011(2) 0.035(2) 
C4 0.044(2) 0.046(2) 0.033(2) 0.017(2) 0.009(2) 0.025(2) 
C5 0.041(2) 0.071(3) 0.044(2) 0.023(2) 0.018(2) 0.036(2) 
C6 0.029(2) 0.074(3) 0.055(3) 0.033(2) 0.013(2) 0.012(2) 
C7 0.031(2) 0.049(2) 0.049(2) 0.022(2) 0.008(2) 0.009(2) 
C8 0.029(2) 0.036(2) 0.036(2) 0.016(2) 0.0048(14) 0.0101(15) 
C9 0.029(2) 0.038(2) 0.034(2) 0.017(2) 0.0055(14) 0.0129(15) 
C10 0.048(2) 0.047(2) 0.047(2) 0.016(2) 0.011(2) 0.023(2) 
C11 0.059(3) 0.060(3) 0.041(2) 0.015(2) 0.013(2) 0.022(2) 
C12 0.051(3) 0.071(3) 0.041(2) 0.028(2) 0.004(2) 0.015(2) 
C13 0.040(2) 0.057(3) 0.042(2) 0.027(2) 0.001(2) 0.006(2) 
C14 0.068(3) 0.081(4) 0.060(3) 0.049(3) 0.007(2) 0.032(3) 
C15 0.064(3) 0.076(3) 0.076(3) 0.048(3) 0.006(3) 0.036(3) 
C16 0.052(3) 0.061(3) 0.066(3) 0.037(2) 0.009(2) 0.030(2) 
C17 0.027(2) 0.046(2) 0.051(2) 0.026(2) 0.006(2) 0.013(2) 
C18 0.029(2) 0.046(2) 0.043(2) 0.023(2) 0.002(2) 0.011(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 
Cl1 C19 1.767(9) . ? 
Cl2 C19 1.536(10) . ? 
Cl3 C19 1.735(12) . ? 
Cl3 Cl3 2.30(2) 2_645 ? 
Cl4 C19 1.69(2) . ? 
Cl5 C19 1.634(13) . ? 
Cl6 C19 1.788(11) . ? 
Mo O5 1.685(3) . ? 
Mo O4 1.925(3) . ? 
Mo O3 1.933(3) . ? 
Mo O2 1.993(3) . ? 
Mo O1 2.037(3) . ? 
Mo N1 2.194(3) . ? 
Mo N2 2.269(3) . ? 
O1 C8 1.327(5) . ? 
O2 C17 1.345(5) . ? 
O3 O4 1.441(4) . ? 
N1 C1 1.331(5) . ? 
N1 C9 1.365(5) . ? 
N2 C10 1.333(5) . ? 
N2 C18 1.357(5) . ? 
C1 C2 1.399(7) . ? 
C1 H1 0.930(5) . ? 
C2 C3 1.368(8) . ? 
C2 H2 0.930(4) . ? 
C3 C4 1.405(6) . ? 
C3 H3 0.930(4) . ? 
C4 C9 1.406(5) . ? 
C4 C5 1.420(7) . ? 
C5 C6 1.348(8) . ? 
C5 H5 0.930(4) . ? 
C6 C7 1.413(7) . ? 
C6 H6 0.930(4) . ? 
C7 C8 1.372(6) . ? 
C7 H7 0.930(4) . ? 
C8 C9 1.422(5) . ? 
C10 C11 1.403(7) . ? 
C10 H10 0.930(5) . ? 
C11 C12 1.356(8) . ? 
C11 H11 0.930(5) . ? 
C12 C13 1.398(7) . ? 
C12 H12 0.930(5) . ? 
C13 C18 1.409(6) . ? 
C13 C14 1.404(7) . ? 
C14 C15 1.363(8) . ? 
C14 H14 0.930(5) . ? 
C15 C16 1.425(7) . ? 
C15 H15 0.930(5) . ? 
C16 C17 1.369(6) . ? 
C16 H16 0.930(5) . ? 
C17 C18 1.402(6) . ? 
 
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 
C19 Cl3 Cl3 151.5(11) . 2_645 ? 
Cl2 C19 Cl1 116.3(6) . . ? 
Cl5 C19 Cl6 110.0(7) . . ? 
O5 Mo O4 104.1(2) . . ? 
O5 Mo O3 100.83(15) . . ? 
O4 Mo O3 43.86(13) . . ? 
O5 Mo O2 103.30(14) . . ? 
O4 Mo O2 78.77(12) . . ? 
O3 Mo O2 121.61(13) . . ? 
O5 Mo O1 156.25(14) . . ? 
O4 Mo O1 97.93(13) . . ? 
O3 Mo O1 88.90(12) . . ? 
O2 Mo O1 89.46(11) . . ? 
O5 Mo N1 85.71(13) . . ? 
O4 Mo N1 122.75(12) . . ? 
O3 Mo N1 78.93(12) . . ? 
O2 Mo N1 154.41(12) . . ? 
O1 Mo N1 74.87(11) . . ? 
O5 Mo N2 84.23(14) . . ? 
O4 Mo N2 154.03(13) . . ? 
O3 Mo N2 159.72(13) . . ? 
O2 Mo N2 75.36(12) . . ? 
O1 Mo N2 79.69(11) . . ? 
N1 Mo N2 81.91(12) . . ? 
C8 O1 Mo 120.3(2) . . ? 
C17 O2 Mo 120.1(2) . . ? 
O4 O3 Mo 67.8(2) . . ? 
O3 O4 Mo 68.3(2) . . ? 
C1 N1 C9 119.0(4) . . ? 
C1 N1 Mo 127.0(3) . . ? 
C9 N1 Mo 114.0(2) . . ? 
C10 N2 C18 118.1(4) . . ? 
C10 N2 Mo 130.7(3) . . ? 
C18 N2 Mo 111.1(3) . . ? 
N1 C1 C2 121.6(4) . . ? 
N1 C1 H1 119.2(4) . . ? 
C2 C1 H1 119.2(4) . . ? 
C3 C2 C1 119.9(4) . . ? 
C3 C2 H2 120.1(5) . . ? 
C1 C2 H2 120.1(5) . . ? 
C2 C3 C4 120.1(4) . . ? 
C2 C3 H3 119.9(5) . . ? 
C4 C3 H3 119.9(5) . . ? 
C3 C4 C9 116.7(4) . . ? 
C3 C4 C5 126.1(4) . . ? 
C9 C4 C5 117.1(4) . . ? 
C6 C5 C4 119.6(4) . . ? 
C6 C5 H5 120.2(5) . . ? 
C4 C5 H5 120.2(5) . . ? 
C5 C6 C7 123.4(4) . . ? 
C5 C6 H6 118.3(5) . . ? 
C7 C6 H6 118.3(5) . . ? 
C8 C7 C6 118.9(4) . . ? 
C8 C7 H7 120.5(4) . . ? 
C6 C7 H7 120.5(4) . . ? 
O1 C8 C7 125.7(4) . . ? 
O1 C8 C9 116.0(3) . . ? 
C7 C8 C9 118.3(4) . . ? 
N1 C9 C4 122.7(4) . . ? 
N1 C9 C8 114.7(3) . . ? 
C4 C9 C8 122.6(4) . . ? 
N2 C10 C11 122.1(4) . . ? 
N2 C10 H10 119.0(4) . . ? 
C11 C10 H10 119.0(4) . . ? 
C12 C11 C10 120.1(4) . . ? 
C12 C11 H11 120.0(5) . . ? 
C10 C11 H11 120.0(5) . . ? 
C11 C12 C13 119.4(4) . . ? 
C11 C12 H12 120.3(5) . . ? 
C13 C12 H12 120.3(5) . . ? 
C12 C13 C18 117.6(4) . . ? 
C12 C13 C14 124.5(4) . . ? 
C18 C13 C14 117.9(4) . . ? 
C15 C14 C13 120.1(4) . . ? 
C15 C14 H14 120.0(5) . . ? 
C13 C14 H14 120.0(6) . . ? 
C14 C15 C16 122.1(4) . . ? 
C14 C15 H15 118.9(6) . . ? 
C16 C15 H15 118.9(6) . . ? 
C17 C16 C15 118.2(5) . . ? 
C17 C16 H16 120.9(5) . . ? 
C15 C16 H16 120.9(5) . . ? 
O2 C17 C16 122.4(4) . . ? 
O2 C17 C18 117.5(3) . . ? 
C16 C17 C18 120.1(4) . . ? 
N2 C18 C17 115.8(4) . . ? 
N2 C18 C13 122.7(4) . . ? 
C17 C18 C13 121.5(4) . . ? 
 
_refine_diff_density_max    1.016 
_refine_diff_density_min   -1.214 
_refine_diff_density_rms    0.098