# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dewen Dong' _publ_contact_author_email DONGDW663@NENU.EDU.CN _publ_section_title ; Efficient and Divergent Synthesis of Cyclophosphamide Analogues from 2-Arylamino-3-acetyl-5,6-dihydro-4H-pyrans ; loop_ _publ_author_name 'Dewen Dong.' 'Peng Huang.' 'Yongjiu Liang.' 'Kewei Wang.' 'Dexuan Xiang.' ; Guangyuan Zhou ; data_xiang3 _database_code_depnum_ccdc_archive 'CCDC 689420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 Cl2 N O3 P' _chemical_formula_weight 334.12 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.560(3) _cell_length_b 10.346(3) _cell_length_c 15.722(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.543(5) _cell_angle_gamma 90.00 _cell_volume 1505.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8234 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.09 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.542 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.883 _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_process_details 'ABSCOR by T.Higashi 8 March, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Rigaku R-AXIS RAPID IP' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean 0.01 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8234 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.09 _reflns_number_total 2975 _reflns_number_gt 2179 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID AUTO' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+0.0000P] 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_number_reflns 2975 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1679 _refine_ls_wR_factor_gt 0.1501 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _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 P1 P 0.00051(8) 0.68019(7) 0.11502(5) 0.0483(3) Uani 1 1 d . . . Cl1 Cl -0.16715(10) 0.55945(9) 0.09638(6) 0.0737(3) Uani 1 1 d . . . Cl2 Cl -0.47852(15) 1.20753(11) -0.12145(8) 0.1082(5) Uani 1 1 d . . . N1 N -0.0564(3) 0.8206(2) 0.14417(14) 0.0452(6) Uani 1 1 d . . . O1 O 0.0170(2) 0.70696(19) 0.01939(13) 0.0559(6) Uani 1 1 d . . . O2 O -0.1781(2) 1.0088(2) 0.10910(13) 0.0615(6) Uani 1 1 d . . . O3 O 0.1290(2) 0.6259(2) 0.17400(14) 0.0658(7) Uani 1 1 d . . . C1 C -0.1481(3) 0.7835(3) 0.2745(2) 0.0554(8) Uani 1 1 d . . . H1A H -0.2236 0.7350 0.2405 0.066 Uiso 1 1 calc R . . C2 C -0.1344(4) 0.7992(3) 0.3647(2) 0.0616(9) Uani 1 1 d . . . H2A H -0.1994 0.7592 0.3914 0.074 Uiso 1 1 calc R . . C3 C -0.0245(4) 0.8739(3) 0.4133(2) 0.0623(9) Uani 1 1 d . . . H3A H -0.0150 0.8844 0.4732 0.075 Uiso 1 1 calc R . . C4 C 0.0720(4) 0.9335(3) 0.3740(2) 0.0607(9) Uani 1 1 d . . . H4A H 0.1447 0.9856 0.4073 0.073 Uiso 1 1 calc R . . C5 C 0.0611(3) 0.9162(3) 0.28612(19) 0.0526(7) Uani 1 1 d . . . H5A H 0.1274 0.9551 0.2599 0.063 Uiso 1 1 calc R . . C6 C -0.0483(3) 0.8410(3) 0.23695(17) 0.0435(7) Uani 1 1 d . . . C7 C -0.1301(3) 0.9133(3) 0.08249(18) 0.0460(7) Uani 1 1 d . . . C8 C -0.1414(3) 0.8883(3) -0.01127(17) 0.0459(7) Uani 1 1 d . . . C9 C -0.2310(3) 0.9868(3) -0.07406(19) 0.0510(7) Uani 1 1 d . . . H9A H -0.2166 1.0718 -0.0472 0.061 Uiso 1 1 calc R . . H9B H -0.1979 0.9897 -0.1275 0.061 Uiso 1 1 calc R . . C10 C -0.3894(3) 0.9549(3) -0.0969(2) 0.0600(8) Uani 1 1 d . . . H10A H -0.4226 0.9546 -0.0435 0.072 Uiso 1 1 calc R . . H10B H -0.4029 0.8685 -0.1216 0.072 Uiso 1 1 calc R . . C11 C -0.4814(4) 1.0482(3) -0.1616(2) 0.0636(9) Uani 1 1 d . . . H11A H -0.5804 1.0174 -0.1769 0.076 Uiso 1 1 calc R . . H11B H -0.4477 1.0490 -0.2149 0.076 Uiso 1 1 calc R . . C12 C -0.0754(3) 0.7906(3) -0.04005(18) 0.0477(7) Uani 1 1 d . . . C13 C -0.0765(4) 0.7547(4) -0.1312(2) 0.0620(9) Uani 1 1 d . . . H13A H -0.1394 0.8121 -0.1714 0.093 Uiso 1 1 calc R . . H13B H -0.1105 0.6675 -0.1424 0.093 Uiso 1 1 calc R . . H13C H 0.0196 0.7612 -0.1391 0.093 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 0.0530(5) 0.0418(5) 0.0452(5) 0.0021(3) 0.0033(3) 0.0067(3) Cl1 0.0799(6) 0.0533(5) 0.0812(7) -0.0045(4) 0.0079(5) -0.0164(4) Cl2 0.1142(9) 0.0659(7) 0.1145(10) -0.0239(6) -0.0275(7) 0.0312(6) N1 0.0513(14) 0.0401(13) 0.0398(13) 0.0021(10) 0.0031(10) 0.0062(10) O1 0.0646(13) 0.0524(13) 0.0491(12) 0.0015(9) 0.0114(10) 0.0134(10) O2 0.0770(15) 0.0509(13) 0.0517(13) 0.0014(10) 0.0068(11) 0.0188(11) O3 0.0625(14) 0.0678(15) 0.0564(13) 0.0025(11) -0.0051(10) 0.0222(11) C1 0.0441(17) 0.0586(19) 0.062(2) 0.0004(15) 0.0107(14) 0.0060(14) C2 0.062(2) 0.065(2) 0.067(2) 0.0043(16) 0.0335(17) 0.0115(16) C3 0.085(2) 0.055(2) 0.0477(18) -0.0011(15) 0.0192(17) 0.0150(18) C4 0.077(2) 0.0538(19) 0.0483(18) -0.0046(14) 0.0099(16) -0.0028(16) C5 0.0601(18) 0.0492(17) 0.0470(16) 0.0029(13) 0.0109(13) -0.0064(14) C6 0.0485(16) 0.0393(15) 0.0399(14) 0.0033(11) 0.0060(12) 0.0079(12) C7 0.0451(16) 0.0428(16) 0.0465(16) 0.0044(12) 0.0043(12) 0.0017(13) C8 0.0450(15) 0.0460(16) 0.0424(15) 0.0048(12) 0.0028(12) -0.0028(13) C9 0.0513(17) 0.0532(18) 0.0458(16) 0.0076(13) 0.0070(13) -0.0019(14) C10 0.0574(19) 0.056(2) 0.064(2) 0.0046(15) 0.0109(15) -0.0048(15) C11 0.0579(19) 0.067(2) 0.0577(19) -0.0049(16) -0.0014(15) 0.0090(16) C12 0.0524(17) 0.0455(16) 0.0414(15) 0.0023(12) 0.0046(13) -0.0040(13) C13 0.075(2) 0.063(2) 0.0488(19) -0.0026(15) 0.0157(16) 0.0012(17) _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 O3 1.453(2) . ? P1 O1 1.575(2) . ? P1 N1 1.656(2) . ? P1 Cl1 1.9949(13) . ? Cl2 C11 1.763(3) . ? N1 C7 1.420(3) . ? N1 C6 1.456(3) . ? O1 C12 1.410(3) . ? O2 C7 1.207(4) . ? C1 C6 1.377(4) . ? C1 C2 1.399(4) . ? C1 H1A 0.9300 . ? C2 C3 1.372(5) . ? C2 H2A 0.9300 . ? C3 C4 1.377(5) . ? C3 H3A 0.9300 . ? C4 C5 1.372(4) . ? C4 H4A 0.9300 . ? C5 C6 1.375(4) . ? C5 H5A 0.9300 . ? C7 C8 1.474(4) . ? C8 C12 1.330(4) . ? C8 C9 1.524(4) . ? C9 C10 1.502(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.514(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.478(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 P1 O1 113.96(13) . . ? O3 P1 N1 116.52(13) . . ? O1 P1 N1 103.20(11) . . ? O3 P1 Cl1 111.76(11) . . ? O1 P1 Cl1 103.83(9) . . ? N1 P1 Cl1 106.39(10) . . ? C7 N1 C6 118.6(2) . . ? C7 N1 P1 123.06(19) . . ? C6 N1 P1 117.76(17) . . ? C12 O1 P1 123.0(2) . . ? C6 C1 C2 119.0(3) . . ? C6 C1 H1A 120.5 . . ? C2 C1 H1A 120.5 . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C6 C5 C4 119.6(3) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C5 C6 C1 121.0(3) . . ? C5 C6 N1 119.1(3) . . ? C1 C6 N1 119.9(3) . . ? O2 C7 N1 118.9(3) . . ? O2 C7 C8 123.5(3) . . ? N1 C7 C8 117.6(3) . . ? C12 C8 C7 123.5(2) . . ? C12 C8 C9 121.7(3) . . ? C7 C8 C9 114.7(3) . . ? C10 C9 C8 112.2(2) . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C9 C10 C11 113.7(3) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 Cl2 113.7(2) . . ? C10 C11 H11A 108.8 . . ? Cl2 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? Cl2 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C8 C12 O1 120.9(3) . . ? C8 C12 C13 129.2(3) . . ? O1 C12 C13 109.8(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.451 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.060