# CCDC Deposition number: xxxxxx #============================================================================== # SUBMISSION DETAILS _publ_requested_journal ' J. Am. Chem. Soc. ' _publ_contact_author_name ' Dr ERT Tiekink ' _publ_contact_author_address ; Department of Chemistry, The University of Texas, One UTSA Circle, San Antonio, Texas 78249-0621, USA ; _publ_contact_author_phone ' 1 210 458 5469 ' _publ_contact_author_fax ' 1 210 458 7428 ' _publ_contact_author_email ; Edward.Tiekink@utsa.edu ; data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 Br O5 P' _chemical_formula_sum 'C18 H22 Br O5 P' _chemical_formula_weight 429.24 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' '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' '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.140(2) _cell_length_b 5.7779(12) _cell_length_c 16.691(3) _cell_angle_alpha 90 _cell_angle_beta 104.79(3) _cell_angle_gamma 90 _cell_volume 945.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2824 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.2 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 2.283 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.607 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'AFC12\K/SATURN724' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 6979 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.058 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 26.5 _reflns_number_total 3568 _reflns_number_gt 3382 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear' _computing_data_reduction 'CrystalClear' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Brandenburg, 2006)' _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^)+(0.0353P)^2^+0.386P] 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 constr _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 0.015(10) _refine_ls_number_reflns 3568 _refine_ls_number_parameters 236 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.044 _refine_ls_wR_factor_ref 0.094 _refine_ls_wR_factor_gt 0.091 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _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 Br14 Br 0.57412(4) -0.25929(15) 0.62623(3) 0.04821(16) Uani 1 1 d . . . P2 P 0.00084(10) 0.0452(2) 0.76819(6) 0.0228(2) Uani 1 1 d . . . O1 O 0.1397(3) 0.4301(5) 0.76143(18) 0.0293(6) Uani 1 1 d D . . H1O H 0.098(4) 0.514(7) 0.788(2) 0.044 Uiso 1 1 d D . . O1W O 0.0072(4) -0.2519(7) 0.97010(18) 0.0583(9) Uani 1 1 d D . . H1W H 0.002(6) -0.255(9) 0.9191(7) 0.087 Uiso 1 1 d D . . H2W H 0.009(7) -0.392(3) 0.984(3) 0.087 Uiso 1 1 d D . . O2 O 0.0088(3) -0.1965(4) 0.80037(15) 0.0291(6) Uani 1 1 d . . . O3 O 0.4175(3) 0.4060(6) 0.89220(18) 0.0380(7) Uani 1 1 d . . . O21 O -0.0871(2) 0.2144(5) 0.80840(14) 0.0259(5) Uani 1 1 d . . . C1 C 0.1642(3) 0.2055(7) 0.7962(2) 0.0220(8) Uani 1 1 d . . . C2 C 0.2089(4) 0.2109(7) 0.8912(2) 0.0276(8) Uani 1 1 d . . . H2A H 0.1347 0.2829 0.9113 0.033 Uiso 1 1 calc R . . H2B H 0.2182 0.0491 0.9114 0.033 Uiso 1 1 calc R . . C3 C 0.3397(4) 0.3364(6) 0.9309(2) 0.0283(9) Uani 1 1 d . . . C4 C 0.3666(5) 0.3686(9) 1.0232(3) 0.0445(12) Uani 1 1 d . . . H4A H 0.3941 0.2205 1.0511 0.067 Uiso 1 1 calc R . . H4B H 0.2835 0.4240 1.0367 0.067 Uiso 1 1 calc R . . H4C H 0.4398 0.4822 1.0419 0.067 Uiso 1 1 calc R . . C11 C 0.2671(4) 0.0904(6) 0.7559(2) 0.0228(8) Uani 1 1 d . . . C12 C 0.3013(4) 0.1955(7) 0.6892(2) 0.0309(9) Uani 1 1 d . . . H12 H 0.2608 0.3397 0.6693 0.037 Uiso 1 1 calc R . . C13 C 0.3937(4) 0.0940(7) 0.6509(2) 0.0296(9) Uani 1 1 d . . . H13 H 0.4178 0.1684 0.6059 0.035 Uiso 1 1 calc R . . C14 C 0.4496(4) -0.1171(7) 0.6798(2) 0.0297(9) Uani 1 1 d . . . C15 C 0.4176(4) -0.2265(7) 0.7454(2) 0.0299(9) Uani 1 1 d . . . H15 H 0.4573 -0.3718 0.7644 0.036 Uiso 1 1 calc R . . C16 C 0.3267(4) -0.1221(7) 0.7834(2) 0.0262(8) Uani 1 1 d . . . H16 H 0.3046 -0.1966 0.8290 0.031 Uiso 1 1 calc R . . C21 C -0.0698(4) 0.0655(7) 0.6594(2) 0.0249(8) Uani 1 1 d . . . C22 C -0.0543(4) -0.1151(7) 0.6068(2) 0.0303(9) Uani 1 1 d . . . H22 H -0.0024 -0.2481 0.6286 0.036 Uiso 1 1 calc R . . C23 C -0.1158(4) -0.0985(8) 0.5218(3) 0.0336(10) Uani 1 1 d . . . H23 H -0.1061 -0.2214 0.4859 0.040 Uiso 1 1 calc R . . C24 C -0.1898(4) 0.0934(7) 0.4901(3) 0.0367(10) Uani 1 1 d . . . H24 H -0.2318 0.1019 0.4323 0.044 Uiso 1 1 calc R . . C25 C -0.2041(4) 0.2751(8) 0.5410(2) 0.0389(10) Uani 1 1 d . . . H25 H -0.2547 0.4085 0.5182 0.047 Uiso 1 1 calc R . . C26 C -0.1447(4) 0.2630(8) 0.6256(2) 0.0302(8) Uani 1 1 d . . . H26 H -0.1547 0.3878 0.6606 0.036 Uiso 1 1 calc R . . C31 C -0.2290(4) 0.1602(8) 0.8061(3) 0.0384(10) Uani 1 1 d . . . H31A H -0.2337 0.0163 0.8375 0.046 Uiso 1 1 calc R . . H31B H -0.2827 0.1376 0.7482 0.046 Uiso 1 1 calc R . . C32 C -0.2844(5) 0.3569(9) 0.8440(3) 0.0504(13) Uani 1 1 d . . . H32A H -0.3797 0.3257 0.8431 0.076 Uiso 1 1 calc R . . H32B H -0.2792 0.4983 0.8125 0.076 Uiso 1 1 calc R . . H32C H -0.2309 0.3771 0.9014 0.076 Uiso 1 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 Br14 0.0388(2) 0.0579(3) 0.0544(3) -0.0160(2) 0.0236(2) 0.0052(2) P2 0.0238(5) 0.0223(5) 0.0239(5) -0.0009(4) 0.0092(4) 0.0017(4) O1 0.0350(16) 0.0203(13) 0.0357(16) 0.0010(11) 0.0149(13) 0.0046(12) O1W 0.086(2) 0.058(2) 0.0360(17) -0.0023(19) 0.0257(18) -0.006(3) O2 0.0414(16) 0.0215(14) 0.0278(13) 0.0025(10) 0.0150(12) 0.0016(11) O3 0.0343(17) 0.0476(18) 0.0342(16) -0.0023(14) 0.0123(14) -0.0089(14) O21 0.0224(12) 0.0297(14) 0.0284(12) -0.0040(12) 0.0116(10) 0.0014(12) C1 0.0196(17) 0.024(2) 0.0237(17) -0.0003(15) 0.0068(14) 0.0055(15) C2 0.0313(19) 0.030(2) 0.0242(18) -0.0036(17) 0.0116(15) 0.0019(18) C3 0.031(2) 0.0249(19) 0.029(2) 0.0001(16) 0.0062(17) 0.0062(16) C4 0.045(3) 0.058(3) 0.030(2) -0.009(2) 0.010(2) -0.009(2) C11 0.0190(18) 0.0242(19) 0.0243(18) -0.0031(15) 0.0040(15) 0.0002(14) C12 0.036(2) 0.033(2) 0.0255(19) 0.0021(17) 0.0092(17) 0.0036(17) C13 0.034(2) 0.033(2) 0.0239(19) -0.0008(17) 0.0110(17) -0.0012(17) C14 0.023(2) 0.035(2) 0.032(2) -0.0130(18) 0.0074(17) -0.0029(17) C15 0.0232(19) 0.028(2) 0.037(2) -0.0001(18) 0.0047(16) 0.0017(17) C16 0.026(2) 0.0239(19) 0.0293(19) 0.0020(16) 0.0093(16) 0.0006(16) C21 0.0227(19) 0.0254(19) 0.0264(19) -0.0036(15) 0.0059(15) -0.0001(15) C22 0.033(2) 0.026(2) 0.031(2) -0.0040(17) 0.0069(18) 0.0067(17) C23 0.039(2) 0.033(2) 0.028(2) -0.0100(17) 0.0086(19) -0.0032(19) C24 0.037(2) 0.044(3) 0.027(2) -0.0053(19) 0.0024(18) 0.000(2) C25 0.043(2) 0.039(3) 0.031(2) 0.002(2) 0.0025(18) 0.007(2) C26 0.036(2) 0.027(2) 0.0284(18) -0.0020(18) 0.0099(16) 0.0062(19) C31 0.031(2) 0.045(3) 0.044(2) -0.0023(19) 0.018(2) -0.0021(18) C32 0.037(3) 0.057(3) 0.064(3) 0.004(3) 0.024(2) 0.017(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 Br14 C14 1.909(4) . ? P2 O2 1.491(2) . ? P2 O21 1.584(3) . ? P2 C21 1.778(4) . ? P2 C1 1.850(4) . ? O1 C1 1.418(5) . ? O1 H1O 0.8400(10) . ? O1W H1W 0.8400(10) . ? O1W H2W 0.8400(11) . ? O3 C3 1.209(5) . ? O21 C31 1.464(5) . ? C1 C11 1.531(5) . ? C1 C2 1.534(4) . ? C2 C3 1.508(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.506(5) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C11 C12 1.388(5) . ? C11 C16 1.393(5) . ? C12 C13 1.392(5) . ? C12 H12 0.9500 . ? C13 C14 1.379(6) . ? C13 H13 0.9500 . ? C14 C15 1.373(5) . ? C15 C16 1.383(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.397(5) . ? C21 C26 1.407(5) . ? C22 C23 1.400(6) . ? C22 H22 0.9500 . ? C23 C24 1.368(6) . ? C23 H23 0.9500 . ? C24 C25 1.382(6) . ? C24 H24 0.9500 . ? C25 C26 1.388(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C32 1.479(6) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? 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 O2 P2 O21 114.20(15) . . ? O2 P2 C21 113.59(17) . . ? O21 P2 C21 105.60(16) . . ? O2 P2 C1 114.53(16) . . ? O21 P2 C1 98.54(15) . . ? C21 P2 C1 109.05(17) . . ? C1 O1 H1O 112(3) . . ? H1W O1W H2W 104.68(18) . . ? C31 O21 P2 120.9(2) . . ? O1 C1 C11 106.6(3) . . ? O1 C1 C2 112.3(3) . . ? C11 C1 C2 114.1(3) . . ? O1 C1 P2 107.6(2) . . ? C11 C1 P2 109.7(2) . . ? C2 C1 P2 106.3(2) . . ? C3 C2 C1 117.3(3) . . ? C3 C2 H2A 108.0 . . ? C1 C2 H2A 108.0 . . ? C3 C2 H2B 108.0 . . ? C1 C2 H2B 108.0 . . ? H2A C2 H2B 107.2 . . ? O3 C3 C2 123.1(3) . . ? O3 C3 C4 122.2(4) . . ? C2 C3 C4 114.7(4) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C12 C11 C16 118.3(3) . . ? C12 C11 C1 120.0(3) . . ? C16 C11 C1 121.7(3) . . ? C11 C12 C13 121.3(4) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 118.5(4) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C15 121.8(4) . . ? C13 C14 Br14 118.6(3) . . ? C15 C14 Br14 119.6(3) . . ? C14 C15 C16 119.0(4) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C15 C16 C11 121.2(4) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C22 C21 C26 119.3(3) . . ? C22 C21 P2 120.8(3) . . ? C26 C21 P2 119.9(3) . . ? C21 C22 C23 119.5(4) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 120.4(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 120.7(4) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C24 C25 C26 120.1(4) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 119.9(4) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? O21 C31 C32 107.6(4) . . ? O21 C31 H31A 110.2 . . ? C32 C31 H31A 110.2 . . ? O21 C31 H31B 110.2 . . ? C32 C31 H31B 110.2 . . ? H31A C31 H31B 108.5 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P2 O21 C31 -55.9(3) . . . . ? C21 P2 O21 C31 69.7(3) . . . . ? C1 P2 O21 C31 -177.7(3) . . . . ? O2 P2 C1 O1 -179.9(2) . . . . ? O21 P2 C1 O1 -58.3(2) . . . . ? C21 P2 C1 O1 51.5(3) . . . . ? O2 P2 C1 C11 64.5(3) . . . . ? O21 P2 C1 C11 -173.9(2) . . . . ? C21 P2 C1 C11 -64.1(3) . . . . ? O2 P2 C1 C2 -59.4(3) . . . . ? O21 P2 C1 C2 62.2(3) . . . . ? C21 P2 C1 C2 172.1(2) . . . . ? O1 C1 C2 C3 -61.6(4) . . . . ? C11 C1 C2 C3 59.9(5) . . . . ? P2 C1 C2 C3 -179.0(3) . . . . ? C1 C2 C3 O3 -9.4(6) . . . . ? C1 C2 C3 C4 170.7(4) . . . . ? O1 C1 C11 C12 -9.3(4) . . . . ? C2 C1 C11 C12 -133.8(4) . . . . ? P2 C1 C11 C12 107.0(3) . . . . ? O1 C1 C11 C16 171.9(3) . . . . ? C2 C1 C11 C16 47.4(5) . . . . ? P2 C1 C11 C16 -71.8(4) . . . . ? C16 C11 C12 C13 -0.7(5) . . . . ? C1 C11 C12 C13 -179.5(3) . . . . ? C11 C12 C13 C14 1.1(6) . . . . ? C12 C13 C14 C15 -0.8(5) . . . . ? C12 C13 C14 Br14 179.0(3) . . . . ? C13 C14 C15 C16 0.1(6) . . . . ? Br14 C14 C15 C16 -179.7(3) . . . . ? C14 C15 C16 C11 0.4(6) . . . . ? C12 C11 C16 C15 -0.1(5) . . . . ? C1 C11 C16 C15 178.8(3) . . . . ? O2 P2 C21 C22 -29.9(4) . . . . ? O21 P2 C21 C22 -155.8(3) . . . . ? C1 P2 C21 C22 99.1(3) . . . . ? O2 P2 C21 C26 148.7(3) . . . . ? O21 P2 C21 C26 22.8(4) . . . . ? C1 P2 C21 C26 -82.3(3) . . . . ? C26 C21 C22 C23 -1.3(6) . . . . ? P2 C21 C22 C23 177.3(3) . . . . ? C21 C22 C23 C24 0.5(6) . . . . ? C22 C23 C24 C25 0.6(7) . . . . ? C23 C24 C25 C26 -0.9(7) . . . . ? C24 C25 C26 C21 0.1(6) . . . . ? C22 C21 C26 C25 1.0(6) . . . . ? P2 C21 C26 C25 -177.6(3) . . . . ? P2 O21 C31 C32 -176.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.31 _refine_diff_density_min -0.37 _refine_diff_density_rms 0.066