# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_jb93 _database_code_depnum_ccdc_archive 'CCDC 900421' #TrackingRef 'archive_Jb93.cif' _audit_creation_date 2012-02-27T17:03:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H19 N2 O5 P1' _chemical_formula_sum 'C16 H19 N2 O5 P' _chemical_formula_weight 350.3 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.116(6) _cell_length_b 11.264(7) _cell_length_c 13.284(8) _cell_angle_alpha 111.01(7) _cell_angle_beta 92.49(7) _cell_angle_gamma 101.66(8) _cell_volume 829.9(12) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3 _cell_measurement_theta_max 14 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.195 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_absorpt_correction_T_min 0.8895 _exptl_absorpt_correction_T_max 0.9942 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.007368 _diffrn_orient_matrix_ub_12 -0.001921 _diffrn_orient_matrix_ub_13 -0.075917 _diffrn_orient_matrix_ub_21 -0.01403 _diffrn_orient_matrix_ub_22 0.092892 _diffrn_orient_matrix_ub_23 0.027542 _diffrn_orient_matrix_ub_31 0.167495 _diffrn_orient_matrix_ub_32 0.030487 _diffrn_orient_matrix_ub_33 0.009508 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled \w scans' _diffrn_standards_number 1 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 0 0 _diffrn_reflns_av_unetI/netI 0.1558 _diffrn_reflns_number 2918 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 2918 _reflns_number_gt 1204 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0676P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2918 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1876 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1696 _refine_ls_wR_factor_gt 0.1378 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.898 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.205 _refine_diff_density_min -0.23 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 P1 P -0.1021(3) 0.38829(16) 0.63258(13) 0.0565(5) Uani 1 1 d . . . O1 O -0.2033(6) 0.4536(4) 0.5726(3) 0.0624(11) Uani 1 1 d . . . O2 O 0.1266(6) 0.4657(4) 0.7066(3) 0.0749(12) Uani 1 1 d . . . O3 O -0.2592(6) 0.3546(4) 0.7124(3) 0.0713(12) Uani 1 1 d . . . O6 O 0.4413(6) 0.0193(4) 0.3577(3) 0.0676(11) Uani 1 1 d . . . O8 O -0.1588(7) 0.1739(4) 0.2874(3) 0.0730(12) Uani 1 1 d . . . N1 N 0.0526(8) 0.1700(4) 0.6003(4) 0.0604(13) Uani 1 1 d . . . N7 N 0.1329(7) 0.0770(4) 0.2975(4) 0.0527(11) Uani 1 1 d . . . C2 C 0.2396(10) 0.1541(5) 0.5661(5) 0.0628(16) Uani 1 1 d . . . H2 H 0.332 0.1149 0.5949 0.075 Uiso 1 1 calc R . . C3 C 0.3039(8) 0.2014(5) 0.4774(4) 0.0526(14) Uani 1 1 d . . . H3 H 0.4447 0.269 0.4987 0.063 Uiso 1 1 calc R . . C4 C 0.1008(8) 0.2524(5) 0.4550(4) 0.0497(14) Uani 1 1 d . . . H4 H 0.1462 0.3444 0.4635 0.06 Uiso 1 1 calc R . . C5 C -0.0547(9) 0.2353(5) 0.5413(4) 0.0552(15) Uani 1 1 d . . . H5 H -0.2002 0.1778 0.5033 0.066 Uiso 1 1 calc R . . C6 C 0.3076(8) 0.0875(5) 0.3736(4) 0.0510(14) Uani 1 1 d . . . C8 C 0.0006(9) 0.1652(5) 0.3378(5) 0.0566(15) Uani 1 1 d . . . C21 C 0.3107(11) 0.5402(7) 0.6771(5) 0.088(2) Uani 1 1 d . . . H21A H 0.2537 0.5855 0.6357 0.106 Uiso 1 1 calc R . . H21B H 0.3934 0.4816 0.6308 0.106 Uiso 1 1 calc R . . C22 C 0.4609(11) 0.6342(6) 0.7701(5) 0.091(2) Uani 1 1 d . . . H22A H 0.3796 0.692 0.8165 0.136 Uiso 1 1 calc R . . H22B H 0.58 0.6838 0.7466 0.136 Uiso 1 1 calc R . . H22C H 0.5235 0.5895 0.8094 0.136 Uiso 1 1 calc R . . C31 C -0.1996(12) 0.3256(7) 0.8054(5) 0.093(2) Uani 1 1 d . . . H31A H -0.0371 0.3486 0.823 0.112 Uiso 1 1 calc R . . H31B H -0.2519 0.2326 0.7888 0.112 Uiso 1 1 calc R . . C32 C -0.2996(16) 0.3982(9) 0.8979(6) 0.149(4) Uani 1 1 d . . . H32A H -0.4557 0.3893 0.876 0.223 Uiso 1 1 calc R . . H32B H -0.2229 0.4889 0.9245 0.223 Uiso 1 1 calc R . . H32C H -0.2865 0.3646 0.9543 0.223 Uiso 1 1 calc R . . C71 C 0.0917(9) -0.0174(6) 0.1877(4) 0.0550(14) Uani 1 1 d . . . C72 C 0.2620(10) -0.0227(6) 0.1237(5) 0.0683(17) Uani 1 1 d . . . H72 H 0.4038 0.0323 0.1519 0.082 Uiso 1 1 calc R . . C73 C 0.2222(12) -0.1097(7) 0.0178(5) 0.082(2) Uani 1 1 d . . . H73 H 0.3378 -0.1143 -0.0257 0.098 Uiso 1 1 calc R . . C74 C 0.0122(13) -0.1899(7) -0.0242(5) 0.082(2) Uani 1 1 d . . . H74 H -0.0139 -0.2478 -0.0963 0.099 Uiso 1 1 calc R . . C75 C -0.1612(11) -0.1855(6) 0.0397(5) 0.0781(19) Uani 1 1 d . . . H75 H -0.3029 -0.2405 0.011 0.094 Uiso 1 1 calc R . . C76 C -0.1212(10) -0.0973(6) 0.1482(5) 0.0653(17) Uani 1 1 d . . . H76 H -0.2353 -0.0926 0.1925 0.078 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 P1 0.0478(9) 0.0650(11) 0.0588(10) 0.0251(9) 0.0066(7) 0.0144(8) O1 0.056(2) 0.071(3) 0.071(3) 0.037(2) 0.0045(19) 0.022(2) O2 0.055(2) 0.088(3) 0.077(3) 0.035(3) -0.006(2) 0.000(2) O3 0.063(2) 0.091(3) 0.073(3) 0.044(3) 0.020(2) 0.020(2) O6 0.057(2) 0.077(3) 0.070(3) 0.025(2) 0.007(2) 0.025(2) O8 0.073(3) 0.081(3) 0.070(3) 0.028(2) -0.007(2) 0.032(2) N1 0.063(3) 0.066(3) 0.062(3) 0.033(3) 0.009(2) 0.017(3) N7 0.049(3) 0.053(3) 0.056(3) 0.020(2) 0.001(2) 0.014(2) C2 0.078(4) 0.059(4) 0.059(4) 0.030(3) 0.004(3) 0.019(3) C3 0.044(3) 0.049(3) 0.058(4) 0.014(3) -0.003(3) 0.009(3) C4 0.047(3) 0.049(3) 0.051(3) 0.016(3) 0.009(3) 0.013(3) C5 0.048(3) 0.059(4) 0.059(4) 0.024(3) 0.006(3) 0.011(3) C6 0.039(3) 0.052(3) 0.062(4) 0.025(3) 0.004(3) 0.004(3) C8 0.058(4) 0.060(4) 0.060(4) 0.031(3) 0.008(3) 0.017(3) C21 0.072(5) 0.104(6) 0.076(5) 0.025(4) -0.004(4) 0.013(4) C22 0.083(5) 0.077(5) 0.092(5) 0.015(4) -0.014(4) 0.012(4) C31 0.109(6) 0.114(6) 0.090(5) 0.068(5) 0.028(4) 0.043(5) C32 0.235(11) 0.184(10) 0.089(6) 0.078(7) 0.073(7) 0.121(9) C71 0.058(4) 0.056(4) 0.052(4) 0.023(3) 0.003(3) 0.012(3) C72 0.067(4) 0.070(4) 0.069(4) 0.028(4) 0.018(3) 0.011(3) C73 0.094(5) 0.081(5) 0.070(5) 0.026(4) 0.025(4) 0.018(4) C74 0.106(6) 0.080(5) 0.055(4) 0.019(4) 0.005(4) 0.024(5) C75 0.073(4) 0.075(5) 0.068(5) 0.012(4) -0.008(4) 0.010(4) C76 0.063(4) 0.070(4) 0.055(4) 0.021(4) 0.006(3) 0.006(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 P1 O1 1.455(4) . ? P1 O3 1.556(4) . ? P1 O2 1.567(4) . ? P1 C5 1.805(6) . ? O2 C21 1.421(7) . ? O3 C31 1.437(7) . ? O6 C6 1.206(6) . ? O8 C8 1.198(6) . ? N1 C2 1.271(7) . ? N1 C5 1.465(7) . ? N7 C8 1.382(6) . ? N7 C6 1.395(6) . ? N7 C71 1.438(7) . ? C2 C3 1.494(7) . ? C3 C6 1.514(7) . ? C3 C4 1.529(7) . ? C4 C8 1.531(8) . ? C4 C5 1.561(7) . ? C21 C22 1.436(8) . ? C31 C32 1.448(8) . ? C71 C72 1.370(7) . ? C71 C76 1.381(7) . ? C72 C73 1.373(8) . ? C73 C74 1.372(8) . ? C74 C75 1.385(8) . ? C75 C76 1.403(8) . ? 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 O1 P1 O3 111.4(2) . . ? O1 P1 O2 117.2(2) . . ? O3 P1 O2 103.7(2) . . ? O1 P1 C5 110.9(3) . . ? O3 P1 C5 106.5(3) . . ? O2 P1 C5 106.5(3) . . ? C21 O2 P1 125.4(4) . . ? C31 O3 P1 128.0(4) . . ? C2 N1 C5 109.6(5) . . ? C8 N7 C6 113.6(5) . . ? C8 N7 C71 122.8(4) . . ? C6 N7 C71 123.5(4) . . ? N1 C2 C3 116.9(5) . . ? C2 C3 C6 110.6(5) . . ? C2 C3 C4 102.5(4) . . ? C6 C3 C4 105.2(4) . . ? C3 C4 C8 105.1(4) . . ? C3 C4 C5 104.2(4) . . ? C8 C4 C5 113.8(4) . . ? N1 C5 C4 106.7(4) . . ? N1 C5 P1 111.5(4) . . ? C4 C5 P1 112.8(4) . . ? O6 C6 N7 125.4(5) . . ? O6 C6 C3 126.4(5) . . ? N7 C6 C3 108.2(4) . . ? O8 C8 N7 125.4(5) . . ? O8 C8 C4 126.7(5) . . ? N7 C8 C4 107.8(5) . . ? O2 C21 C22 112.3(6) . . ? O3 C31 C32 110.3(6) . . ? C72 C71 C76 121.6(6) . . ? C72 C71 N7 119.3(5) . . ? C76 C71 N7 119.1(5) . . ? C71 C72 C73 119.7(6) . . ? C74 C73 C72 120.2(6) . . ? C73 C74 C75 120.7(6) . . ? C74 C75 C76 119.4(6) . . ? C71 C76 C75 118.5(6) . . ? 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 O1 P1 O2 C21 -43.5(6) . . . . ? O3 P1 O2 C21 -166.7(5) . . . . ? C5 P1 O2 C21 81.2(5) . . . . ? O1 P1 O3 C31 -160.7(5) . . . . ? O2 P1 O3 C31 -33.8(6) . . . . ? C5 P1 O3 C31 78.4(6) . . . . ? C5 N1 C2 C3 -0.7(7) . . . . ? N1 C2 C3 C6 -113.6(6) . . . . ? N1 C2 C3 C4 -1.9(6) . . . . ? C2 C3 C4 C8 -116.6(4) . . . . ? C6 C3 C4 C8 -0.9(6) . . . . ? C2 C3 C4 C5 3.4(5) . . . . ? C6 C3 C4 C5 119.1(4) . . . . ? C2 N1 C5 C4 2.9(6) . . . . ? C2 N1 C5 P1 -120.7(5) . . . . ? C3 C4 C5 N1 -3.9(5) . . . . ? C8 C4 C5 N1 110.0(5) . . . . ? C3 C4 C5 P1 118.8(4) . . . . ? C8 C4 C5 P1 -127.3(4) . . . . ? O1 P1 C5 N1 178.5(3) . . . . ? O3 P1 C5 N1 -60.2(4) . . . . ? O2 P1 C5 N1 50.0(4) . . . . ? O1 P1 C5 C4 58.5(4) . . . . ? O3 P1 C5 C4 179.8(4) . . . . ? O2 P1 C5 C4 -70.0(4) . . . . ? C8 N7 C6 O6 178.4(5) . . . . ? C71 N7 C6 O6 -0.9(8) . . . . ? C8 N7 C6 C3 -3.4(6) . . . . ? C71 N7 C6 C3 177.2(5) . . . . ? C2 C3 C6 O6 -69.4(7) . . . . ? C4 C3 C6 O6 -179.3(5) . . . . ? C2 C3 C6 N7 112.5(5) . . . . ? C4 C3 C6 N7 2.5(6) . . . . ? C6 N7 C8 O8 -179.8(5) . . . . ? C71 N7 C8 O8 -0.4(9) . . . . ? C6 N7 C8 C4 2.8(6) . . . . ? C71 N7 C8 C4 -177.8(4) . . . . ? C3 C4 C8 O8 -178.4(6) . . . . ? C5 C4 C8 O8 68.2(7) . . . . ? C3 C4 C8 N7 -1.0(6) . . . . ? C5 C4 C8 N7 -114.4(5) . . . . ? P1 O2 C21 C22 159.8(5) . . . . ? P1 O3 C31 C32 133.5(6) . . . . ? C8 N7 C71 C72 125.9(6) . . . . ? C6 N7 C71 C72 -54.8(7) . . . . ? C8 N7 C71 C76 -51.8(7) . . . . ? C6 N7 C71 C76 127.5(6) . . . . ? C76 C71 C72 C73 -0.3(9) . . . . ? N7 C71 C72 C73 -178.0(5) . . . . ? C71 C72 C73 C74 0.7(10) . . . . ? C72 C73 C74 C75 -0.8(10) . . . . ? C73 C74 C75 C76 0.4(10) . . . . ? C72 C71 C76 C75 0.0(9) . . . . ? N7 C71 C76 C75 177.7(5) . . . . ? C74 C75 C76 C71 -0.1(9) . . . . ? # END of CIF