data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H22 Br Mo N3 O5' _chemical_formula_weight 548.25 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' 'Br' 'Br' -0.2901 2.4595 '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 13.9971(8) _cell_length_b 7.4182(4) _cell_length_c 21.4088(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.3190(10) _cell_angle_gamma 90.00 _cell_volume 2122.16(19) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8780 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 26.8 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 2.536 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6180 _exptl_absorpt_correction_T_max 0.6582 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19023 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3927 _reflns_number_gt 3241 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0354P)^2^+1.5956P] 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 3927 _refine_ls_number_parameters 268 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _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 Mo1 Mo 0.261001(18) 0.44887(4) 0.015141(12) 0.03325(9) Uani 1 1 d . . . N1 N 0.12652(16) 0.3495(3) 0.03999(11) 0.0295(5) Uani 1 1 d . . . N2 N 0.04388(16) 0.3026(3) -0.01318(11) 0.0307(5) Uani 1 1 d . . . N3 N 0.4197(2) 0.4616(4) 0.33407(12) 0.0495(7) Uani 1 1 d . . . O1 O 0.29543(16) 0.5345(3) 0.10406(9) 0.0412(5) Uani 1 1 d . . . O2 O 0.15620(14) 0.3782(3) -0.06797(9) 0.0380(5) Uani 1 1 d . . . O3 O 0.32432(17) 0.2522(3) 0.02724(11) 0.0538(6) Uani 1 1 d . . . O4 O 0.14967(16) 0.6998(3) -0.00324(11) 0.0432(5) Uani 1 1 d D . . O5 O 0.32630(15) 0.5901(3) -0.01933(10) 0.0469(6) Uani 1 1 d . . . Br1 Br -0.23832(3) 0.19475(6) -0.334704(17) 0.06363(14) Uani 1 1 d . . . C1 C 0.1967(2) 0.3601(4) 0.15669(13) 0.0315(6) Uani 1 1 d . . . C2 C 0.2832(2) 0.4607(4) 0.15891(13) 0.0318(6) Uani 1 1 d . . . C3 C 0.3561(2) 0.4930(4) 0.21692(14) 0.0361(7) Uani 1 1 d . . . H3 H 0.4119 0.5607 0.2166 0.043 Uiso 1 1 calc R . . C4 C 0.3486(2) 0.4260(4) 0.27713(14) 0.0383(7) Uani 1 1 d . . . C5 C 0.2618(2) 0.3250(5) 0.27475(15) 0.0443(8) Uani 1 1 d . . . H5 H 0.2543 0.2767 0.3131 0.053 Uiso 1 1 calc R . . C6 C 0.1892(2) 0.2977(4) 0.21712(14) 0.0386(7) Uani 1 1 d . . . H6 H 0.1320 0.2349 0.2177 0.046 Uiso 1 1 calc R . . C7 C 0.1201(2) 0.3206(4) 0.09801(14) 0.0321(6) Uani 1 1 d . . . H7 H 0.0611 0.2704 0.1016 0.038 Uiso 1 1 calc R . . C8 C 0.0677(2) 0.3217(4) -0.06708(14) 0.0314(6) Uani 1 1 d . . . C9 C -0.0055(2) 0.2840(4) -0.13098(14) 0.0327(6) Uani 1 1 d . . . C10 C 0.0105(2) 0.3544(5) -0.18697(15) 0.0420(7) Uani 1 1 d . . . H10 H 0.0688 0.4187 -0.1838 0.050 Uiso 1 1 calc R . . C11 C -0.0591(2) 0.3302(5) -0.24735(15) 0.0488(9) Uani 1 1 d . . . H11 H -0.0482 0.3791 -0.2846 0.059 Uiso 1 1 calc R . . C12 C -0.1439(2) 0.2340(5) -0.25201(15) 0.0423(8) Uani 1 1 d . . . C13 C -0.1614(2) 0.1610(5) -0.19725(16) 0.0480(8) Uani 1 1 d . . . H13 H -0.2195 0.0955 -0.2009 0.058 Uiso 1 1 calc R . . C14 C -0.0916(2) 0.1862(4) -0.13696(15) 0.0434(8) Uani 1 1 d . . . H14 H -0.1028 0.1367 -0.0998 0.052 Uiso 1 1 calc R . . C15 C 0.5032(3) 0.5850(5) 0.33744(17) 0.0531(9) Uani 1 1 d . . . H15A H 0.5252 0.6382 0.3808 0.064 Uiso 1 1 calc R . . H15B H 0.4793 0.6818 0.3062 0.064 Uiso 1 1 calc R . . C16 C 0.5910(3) 0.4975(6) 0.3237(2) 0.0694(11) Uani 1 1 d . . . H16A H 0.6172 0.4049 0.3555 0.104 Uiso 1 1 calc R . . H16B H 0.6419 0.5862 0.3259 0.104 Uiso 1 1 calc R . . H16C H 0.5703 0.4452 0.2807 0.104 Uiso 1 1 calc R . . C17 C 0.4166(3) 0.3793(7) 0.39636(17) 0.0797(14) Uani 1 1 d . . . H17A H 0.4553 0.4530 0.4325 0.096 Uiso 1 1 calc R . . H17B H 0.3480 0.3776 0.3977 0.096 Uiso 1 1 calc R . . C18 C 0.4567(4) 0.1935(10) 0.4047(3) 0.151(3) Uani 1 1 d . . . H18A H 0.4181 0.1195 0.3694 0.227 Uiso 1 1 calc R . . H18B H 0.4526 0.1455 0.4455 0.227 Uiso 1 1 calc R . . H18C H 0.5253 0.1948 0.4048 0.227 Uiso 1 1 calc R . . C19 C 0.1746(3) 0.8793(5) -0.0133(2) 0.0731(12) Uani 1 1 d . . . H19A H 0.2175 0.9276 0.0269 0.110 Uiso 1 1 calc R . . H19B H 0.1146 0.9502 -0.0275 0.110 Uiso 1 1 calc R . . H19C H 0.2086 0.8823 -0.0462 0.110 Uiso 1 1 calc R . . H4 H 0.098(2) 0.694(6) 0.010(2) 0.080 Uiso 1 1 d 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 Mo1 0.02455(14) 0.04423(17) 0.02726(14) 0.00301(12) 0.00205(10) -0.00313(11) N1 0.0254(12) 0.0315(13) 0.0267(12) -0.0009(10) 0.0002(10) -0.0024(10) N2 0.0258(12) 0.0325(13) 0.0299(13) -0.0029(10) 0.0023(10) -0.0034(10) N3 0.0395(16) 0.074(2) 0.0280(13) 0.0029(13) -0.0015(12) -0.0031(15) O1 0.0411(12) 0.0507(13) 0.0264(10) 0.0025(10) 0.0019(9) -0.0180(10) O2 0.0295(11) 0.0554(13) 0.0263(10) -0.0022(10) 0.0039(8) -0.0050(10) O3 0.0403(13) 0.0563(14) 0.0573(15) 0.0044(12) 0.0031(11) 0.0102(11) O4 0.0380(13) 0.0362(12) 0.0571(14) 0.0076(10) 0.0167(11) -0.0006(10) O5 0.0302(12) 0.0706(16) 0.0378(12) 0.0091(11) 0.0069(9) -0.0076(11) Br1 0.0503(2) 0.0839(3) 0.0403(2) -0.02261(18) -0.01151(16) 0.01182(19) C1 0.0299(15) 0.0326(15) 0.0288(14) 0.0014(13) 0.0040(12) -0.0001(12) C2 0.0334(16) 0.0319(15) 0.0282(15) 0.0012(13) 0.0063(12) 0.0010(13) C3 0.0318(16) 0.0405(17) 0.0319(16) -0.0007(13) 0.0034(13) -0.0049(13) C4 0.0353(17) 0.0473(19) 0.0279(15) 0.0014(14) 0.0027(13) 0.0056(14) C5 0.0438(19) 0.058(2) 0.0296(16) 0.0080(15) 0.0085(14) 0.0013(16) C6 0.0302(16) 0.0465(19) 0.0386(17) 0.0049(14) 0.0094(13) -0.0038(14) C7 0.0276(15) 0.0317(16) 0.0365(16) 0.0012(13) 0.0088(13) -0.0029(12) C8 0.0274(15) 0.0287(15) 0.0345(16) -0.0016(12) 0.0036(12) 0.0002(12) C9 0.0277(15) 0.0352(16) 0.0307(15) -0.0054(13) 0.0020(12) 0.0031(13) C10 0.0309(16) 0.058(2) 0.0362(17) -0.0029(15) 0.0078(13) -0.0039(15) C11 0.043(2) 0.070(2) 0.0297(16) -0.0002(16) 0.0055(14) 0.0050(18) C12 0.0323(17) 0.056(2) 0.0320(16) -0.0159(15) -0.0014(13) 0.0087(15) C13 0.0335(18) 0.057(2) 0.048(2) -0.0191(17) 0.0036(15) -0.0102(16) C14 0.0426(19) 0.050(2) 0.0354(17) -0.0075(15) 0.0089(14) -0.0099(15) C15 0.052(2) 0.060(2) 0.0359(18) -0.0071(17) -0.0042(15) -0.0013(18) C16 0.053(2) 0.069(3) 0.084(3) -0.002(2) 0.015(2) -0.007(2) C17 0.059(3) 0.137(4) 0.0325(19) 0.014(2) -0.0023(18) -0.021(3) C18 0.080(4) 0.226(8) 0.161(6) 0.136(6) 0.054(4) 0.056(5) C19 0.086(3) 0.041(2) 0.107(4) 0.009(2) 0.050(3) -0.002(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 O3 1.686(2) . ? Mo1 O5 1.697(2) . ? Mo1 O1 1.927(2) . ? Mo1 O2 2.0096(19) . ? Mo1 N1 2.228(2) . ? Mo1 O4 2.384(2) . ? N1 C7 1.290(4) . ? N1 N2 1.404(3) . ? N2 C8 1.301(4) . ? N3 C4 1.351(4) . ? N3 C15 1.470(4) . ? N3 C17 1.479(4) . ? O1 C2 1.352(3) . ? O2 C8 1.313(3) . ? O4 C19 1.409(4) . ? O4 H4 0.845(10) . ? Br1 C12 1.890(3) . ? C1 C6 1.407(4) . ? C1 C2 1.410(4) . ? C1 C7 1.418(4) . ? C2 C3 1.374(4) . ? C3 C4 1.415(4) . ? C3 H3 0.9300 . ? C4 C5 1.415(4) . ? C5 C6 1.360(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.471(4) . ? C9 C14 1.380(4) . ? C9 C10 1.386(4) . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 C12 1.363(5) . ? C11 H11 0.9300 . ? C12 C13 1.378(5) . ? C13 C14 1.380(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.495(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.479(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O3 Mo1 O5 105.92(12) . . ? O3 Mo1 O1 99.68(10) . . ? O5 Mo1 O1 102.56(9) . . ? O3 Mo1 O2 97.01(10) . . ? O5 Mo1 O2 96.98(9) . . ? O1 Mo1 O2 149.61(9) . . ? O3 Mo1 N1 96.89(10) . . ? O5 Mo1 N1 155.60(10) . . ? O1 Mo1 N1 81.59(8) . . ? O2 Mo1 N1 71.29(8) . . ? O3 Mo1 O4 171.34(10) . . ? O5 Mo1 O4 81.75(9) . . ? O1 Mo1 O4 82.21(9) . . ? O2 Mo1 O4 77.79(8) . . ? N1 Mo1 O4 74.95(8) . . ? C7 N1 N2 117.6(2) . . ? C7 N1 Mo1 126.21(19) . . ? N2 N1 Mo1 116.05(16) . . ? C8 N2 N1 109.0(2) . . ? C4 N3 C15 121.9(3) . . ? C4 N3 C17 121.5(3) . . ? C15 N3 C17 116.7(3) . . ? C2 O1 Mo1 131.70(18) . . ? C8 O2 Mo1 120.89(17) . . ? C19 O4 Mo1 125.7(2) . . ? C19 O4 H4 112(3) . . ? Mo1 O4 H4 119(3) . . ? C6 C1 C2 116.2(2) . . ? C6 C1 C7 120.2(3) . . ? C2 C1 C7 123.6(3) . . ? O1 C2 C3 117.5(3) . . ? O1 C2 C1 121.0(2) . . ? C3 C2 C1 121.5(3) . . ? C2 C3 C4 121.7(3) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? N3 C4 C5 122.0(3) . . ? N3 C4 C3 121.2(3) . . ? C5 C4 C3 116.7(3) . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 123.0(3) . . ? C5 C6 H6 118.5 . . ? C1 C6 H6 118.5 . . ? N1 C7 C1 124.6(3) . . ? N1 C7 H7 117.7 . . ? C1 C7 H7 117.7 . . ? N2 C8 O2 122.7(2) . . ? N2 C8 C9 120.8(3) . . ? O2 C8 C9 116.5(2) . . ? C14 C9 C10 118.7(3) . . ? C14 C9 C8 122.2(3) . . ? C10 C9 C8 119.0(3) . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 119.6(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 121.0(3) . . ? C11 C12 Br1 120.0(3) . . ? C13 C12 Br1 119.0(2) . . ? C12 C13 C14 119.1(3) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C9 C14 C13 120.9(3) . . ? C9 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? N3 C15 C16 114.1(3) . . ? N3 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? N3 C15 H15B 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 N3 112.5(4) . . ? C18 C17 H17A 109.1 . . ? N3 C17 H17A 109.1 . . ? C18 C17 H17B 109.1 . . ? N3 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 C19 H19A 109.5 . . ? O4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 O4 H4 N2 0.845(10) 2.014(16) 2.834(3) 164(4) 3_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.556 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.068