data_C22H20NOP _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 N O P' _chemical_formula_sum 'C22 H20 N O P' _chemical_formula_weight 345.36 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' '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 'P 2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.3586(5) _cell_length_b 15.5598(15) _cell_length_c 21.571(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.462(5) _cell_angle_gamma 90.00 _cell_volume 1793.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9651 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 35.88 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method none _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9714 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details ; Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Kappa DUO CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 55440 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 30.00 _reflns_number_total 10477 _reflns_number_gt 10272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0473P)^2^+0.3255P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef na _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_number_reflns 10477 _refine_ls_number_parameters 616 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.086 _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 P1 P -0.03134(5) 0.327519(17) -0.008717(11) 0.01205(5) Uani 1 1 d . . . O1 O -0.29086(14) 0.29988(5) 0.00156(4) 0.01662(15) Uani 1 1 d . . . N1 N 0.17879(17) 0.25743(6) 0.02017(4) 0.01372(16) Uani 1 1 d D . . H1N H 0.336(2) 0.2684(10) 0.0154(7) 0.016 Uiso 1 1 d D . . C1 C 0.02939(19) 0.43324(7) 0.02445(5) 0.01376(17) Uani 1 1 d . . . C2 C 0.2349(2) 0.48176(8) 0.00912(5) 0.0183(2) Uani 1 1 d . . . H2 H 0.3446 0.4596 -0.0195 0.022 Uiso 1 1 calc R . . C3 C 0.2801(2) 0.56255(8) 0.03562(6) 0.0207(2) Uani 1 1 d . . . H3 H 0.4188 0.5956 0.0245 0.025 Uiso 1 1 calc R . . C4 C 0.1226(2) 0.59480(8) 0.07822(5) 0.0202(2) Uani 1 1 d . . . H4 H 0.1540 0.6498 0.0963 0.024 Uiso 1 1 calc R . . C5 C -0.0802(2) 0.54675(8) 0.09436(6) 0.0225(2) Uani 1 1 d . . . H5 H -0.1865 0.5684 0.1239 0.027 Uiso 1 1 calc R . . C6 C -0.1282(2) 0.46641(8) 0.06709(5) 0.0191(2) Uani 1 1 d . . . H6 H -0.2692 0.4341 0.0777 0.023 Uiso 1 1 calc R . . C7 C 0.03021(19) 0.33731(7) -0.08929(4) 0.01474(18) Uani 1 1 d . . . C8 C -0.1334(3) 0.38859(8) -0.12667(5) 0.0240(2) Uani 1 1 d . . . H8 H -0.2669 0.4176 -0.1090 0.029 Uiso 1 1 calc R . . C9 C -0.1015(3) 0.39731(10) -0.18976(6) 0.0312(3) Uani 1 1 d . . . H9 H -0.2141 0.4320 -0.2151 0.037 Uiso 1 1 calc R . . C10 C 0.0934(3) 0.35577(9) -0.21575(5) 0.0270(3) Uani 1 1 d . . . H10 H 0.1145 0.3619 -0.2589 0.032 Uiso 1 1 calc R . . C11 C 0.2575(3) 0.30531(10) -0.17891(6) 0.0282(3) Uani 1 1 d . . . H11 H 0.3918 0.2771 -0.1968 0.034 Uiso 1 1 calc R . . C12 C 0.2270(2) 0.29558(9) -0.11560(5) 0.0234(2) Uani 1 1 d . . . H12 H 0.3397 0.2607 -0.0905 0.028 Uiso 1 1 calc R . . C13 C 0.1370(2) 0.21195(7) 0.07842(5) 0.01403(18) Uani 1 1 d . . . H13 H -0.0474 0.2023 0.0787 0.017 Uiso 1 1 calc R . . C14 C 0.2587(2) 0.12407(7) 0.07553(5) 0.01714(19) Uani 1 1 d . . . H14 H 0.1884 0.0858 0.0446 0.021 Uiso 1 1 calc R . . C15 C 0.4492(2) 0.09538(7) 0.11091(5) 0.0176(2) Uani 1 1 d . . . C16 C 0.6380(3) 0.06128(8) 0.14354(6) 0.0239(2) Uani 1 1 d D . . H16A H 0.804(3) 0.0686(13) 0.1343(8) 0.029 Uiso 1 1 d D . . H16B H 0.609(3) 0.0284(11) 0.1784(7) 0.029 Uiso 1 1 d D . . C17 C 0.2183(2) 0.26286(7) 0.13663(5) 0.01539(19) Uani 1 1 d . . . C18 C 0.4360(2) 0.31198(8) 0.14007(5) 0.0220(2) Uani 1 1 d . . . H18 H 0.5396 0.3118 0.1063 0.026 Uiso 1 1 calc R . . C19 C 0.5032(3) 0.36137(9) 0.19258(6) 0.0251(2) Uani 1 1 d . . . H19 H 0.6519 0.3948 0.1944 0.030 Uiso 1 1 calc R . . C20 C 0.3543(3) 0.36195(9) 0.24214(6) 0.0261(2) Uani 1 1 d . . . H20 H 0.3992 0.3962 0.2777 0.031 Uiso 1 1 calc R . . C21 C 0.1403(3) 0.31247(11) 0.23950(6) 0.0325(3) Uani 1 1 d . . . H21 H 0.0386 0.3121 0.2737 0.039 Uiso 1 1 calc R . . C22 C 0.0723(2) 0.26298(9) 0.18690(6) 0.0258(2) Uani 1 1 d . . . H22 H -0.0755 0.2291 0.1856 0.031 Uiso 1 1 calc R . . P2 P 0.82647(6) 0.90797(2) 0.401523(16) 0.02336(7) Uani 1 1 d D . . O2 O 1.07358(17) 0.87619(6) 0.38426(5) 0.02565(18) Uani 1 1 d . A . N2 N 0.5988(2) 0.84134(8) 0.37963(5) 0.0261(2) Uani 1 1 d D A . H2N H 0.442(3) 0.8619(12) 0.3817(8) 0.031 Uiso 1 1 d D . . C23 C 0.7135(6) 1.00121(19) 0.35405(16) 0.0195(6) Uani 0.511(3) 1 d PD A 1 C24 C 0.9009(5) 1.05611(17) 0.33649(12) 0.0272(6) Uani 0.511(3) 1 d PD A 1 H24 H 1.0712 1.0428 0.3481 0.033 Uiso 0.511(3) 1 calc PR A 1 C25 C 0.8421(6) 1.13063(19) 0.30194(13) 0.0333(7) Uani 0.511(3) 1 d PD A 1 H25 H 0.9710 1.1682 0.2908 0.040 Uiso 0.511(3) 1 calc PR A 1 C26 C 0.5957(6) 1.1487(2) 0.28437(15) 0.0346(7) Uani 0.511(3) 1 d PD A 1 H26 H 0.5545 1.1999 0.2619 0.042 Uiso 0.511(3) 1 calc PR A 1 C27 C 0.4066(8) 1.0935(2) 0.29899(15) 0.0367(7) Uani 0.511(3) 1 d PD A 1 H27 H 0.2375 1.1056 0.2854 0.044 Uiso 0.511(3) 1 calc PR A 1 C28 C 0.4660(7) 1.0201(2) 0.33370(14) 0.0307(6) Uani 0.511(3) 1 d PD A 1 H28 H 0.3362 0.9822 0.3437 0.037 Uiso 0.511(3) 1 calc PR A 1 C23X C 0.7531(6) 1.0141(2) 0.37652(18) 0.0213(6) Uani 0.489(3) 1 d PD A 2 C24X C 0.8601(6) 1.08650(19) 0.40577(16) 0.0332(7) Uani 0.489(3) 1 d PD A 2 H24X H 0.9707 1.0800 0.4421 0.040 Uiso 0.489(3) 1 calc PR A 2 C25X C 0.8064(7) 1.1686(2) 0.3822(2) 0.0433(9) Uani 0.489(3) 1 d PD A 2 H25X H 0.8789 1.2178 0.4025 0.052 Uiso 0.489(3) 1 calc PR A 2 C26X C 0.6456(7) 1.1778(2) 0.32868(18) 0.0410(9) Uani 0.489(3) 1 d PD A 2 H26X H 0.6088 1.2336 0.3125 0.049 Uiso 0.489(3) 1 calc PR A 2 C27X C 0.5399(9) 1.1073(3) 0.29916(16) 0.0372(8) Uani 0.489(3) 1 d PD A 2 H27X H 0.4297 1.1142 0.2628 0.045 Uiso 0.489(3) 1 calc PR A 2 C28X C 0.5950(8) 1.0241(2) 0.32271(15) 0.0314(7) Uani 0.489(3) 1 d PD A 2 H28X H 0.5242 0.9751 0.3018 0.038 Uiso 0.489(3) 1 calc PR A 2 C29 C 0.854(2) 0.9220(10) 0.4860(3) 0.0237(14) Uani 0.479(13) 1 d PD A 1 C30 C 1.0756(13) 0.8982(4) 0.5257(3) 0.0333(11) Uani 0.479(13) 1 d PD A 1 H30 H 1.2143 0.8736 0.5073 0.040 Uiso 0.479(13) 1 calc PR A 1 C31 C 1.0900(14) 0.9106(3) 0.5895(2) 0.0395(13) Uani 0.479(13) 1 d PD A 1 H31 H 1.2346 0.8918 0.6140 0.047 Uiso 0.479(13) 1 calc PR A 1 C32 C 0.898(2) 0.9496(7) 0.6180(3) 0.0409(17) Uani 0.479(13) 1 d PD A 1 H32 H 0.9129 0.9587 0.6617 0.049 Uiso 0.479(13) 1 calc PR A 1 C33 C 0.6855(10) 0.9754(5) 0.5833(3) 0.0395(14) Uani 0.479(13) 1 d PD A 1 H33 H 0.5556 1.0039 0.6027 0.047 Uiso 0.479(13) 1 calc PR A 1 C34 C 0.6611(7) 0.9595(4) 0.5198(3) 0.0341(11) Uani 0.479(13) 1 d PD A 1 H34 H 0.5075 0.9744 0.4974 0.041 Uiso 0.479(13) 1 calc PR A 1 C29X C 0.827(2) 0.9344(10) 0.4820(3) 0.031(2) Uani 0.521(13) 1 d PD A 2 C30X C 0.9987(13) 0.8913(5) 0.5190(2) 0.0397(14) Uani 0.521(13) 1 d PD A 2 H30X H 1.1113 0.8514 0.5029 0.048 Uiso 0.521(13) 1 calc PR A 2 C31X C 1.0002(13) 0.9089(6) 0.5825(3) 0.068(2) Uani 0.521(13) 1 d PD A 2 H31X H 1.1179 0.8802 0.6105 0.081 Uiso 0.521(13) 1 calc PR A 2 C32X C 0.8387(16) 0.9657(7) 0.6053(4) 0.0426(18) Uani 0.521(13) 1 d PD A 2 H32X H 0.8437 0.9768 0.6487 0.051 Uiso 0.521(13) 1 calc PR A 2 C33X C 0.6683(10) 1.0068(4) 0.5651(3) 0.0507(13) Uani 0.521(13) 1 d PD A 2 H33X H 0.5551 1.0471 0.5805 0.061 Uiso 0.521(13) 1 calc PR A 2 C34X C 0.6600(8) 0.9903(4) 0.5024(3) 0.0387(11) Uani 0.521(13) 1 d PD A 2 H34X H 0.5397 1.0174 0.4742 0.046 Uiso 0.521(13) 1 calc PR A 2 C35 C 0.6320(3) 0.74970(9) 0.39303(7) 0.0309(3) Uani 1 1 d D . . H35 H 0.792(4) 0.7361(14) 0.3975(10) 0.037 Uiso 1 1 d . . . C36 C 0.4433(8) 0.7344(3) 0.44731(16) 0.0269(7) Uani 0.487(4) 1 d PD A 1 H36 H 0.2695 0.7309 0.4350 0.032 Uiso 0.487(4) 1 calc PR A 1 C37 C 0.5111(6) 0.72636(19) 0.50684(14) 0.0320(7) Uani 0.487(4) 1 d PD A 1 C38 C 0.5720(8) 0.7234(3) 0.56456(18) 0.0446(9) Uani 0.487(4) 1 d PD A 1 H38A H 0.593(9) 0.6664(17) 0.580(2) 0.054 Uiso 0.487(4) 1 d PD A 1 H38B H 0.574(9) 0.771(2) 0.5927(19) 0.054 Uiso 0.487(4) 1 d PD A 1 C36X C 0.5291(9) 0.7124(3) 0.44803(17) 0.0315(8) Uani 0.513(4) 1 d PD A 2 H36X H 0.3524 0.7084 0.4486 0.038 Uiso 0.513(4) 1 calc PR A 2 C37X C 0.6619(6) 0.6859(2) 0.49396(13) 0.0338(8) Uani 0.513(4) 1 d PD A 2 C38X C 0.8149(10) 0.6534(3) 0.5381(2) 0.0614(13) Uani 0.513(4) 1 d PD A 2 H38C H 0.903(9) 0.599(2) 0.537(3) 0.074 Uiso 0.513(4) 1 d PD A 2 H38D H 0.856(10) 0.694(3) 0.571(2) 0.074 Uiso 0.513(4) 1 d PD A 2 C39 C 0.5608(2) 0.69444(9) 0.33627(6) 0.0250(2) Uani 1 1 d . A . C40 C 0.7140(3) 0.62725(10) 0.32082(7) 0.0312(3) Uani 1 1 d . . . H40 H 0.8658 0.6167 0.3454 0.037 Uiso 1 1 calc R A . C41 C 0.6484(3) 0.57542(10) 0.27007(8) 0.0342(3) Uani 1 1 d . A . H41 H 0.7557 0.5298 0.2599 0.041 Uiso 1 1 calc R . . C42 C 0.4270(3) 0.58978(10) 0.23406(7) 0.0293(3) Uani 1 1 d . . . H42 H 0.3808 0.5539 0.1994 0.035 Uiso 1 1 calc R A . C43 C 0.2731(3) 0.65726(10) 0.24923(6) 0.0285(3) Uani 1 1 d . A . H43 H 0.1214 0.6677 0.2246 0.034 Uiso 1 1 calc R . . C44 C 0.3392(3) 0.70968(10) 0.30022(6) 0.0274(3) Uani 1 1 d . . . H44 H 0.2330 0.7557 0.3103 0.033 Uiso 1 1 calc R A . 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 0.01088(10) 0.01316(11) 0.01231(10) 0.00154(9) 0.00210(8) 0.00026(9) O1 0.0119(3) 0.0196(4) 0.0185(3) 0.0019(3) 0.0028(3) -0.0012(3) N1 0.0112(4) 0.0151(4) 0.0151(4) 0.0038(3) 0.0026(3) 0.0016(3) C1 0.0152(4) 0.0130(4) 0.0132(4) 0.0012(3) 0.0015(3) 0.0008(3) C2 0.0150(5) 0.0198(5) 0.0205(5) -0.0011(4) 0.0043(4) -0.0014(4) C3 0.0196(5) 0.0195(5) 0.0231(5) -0.0006(4) 0.0015(4) -0.0031(4) C4 0.0242(6) 0.0162(5) 0.0198(5) -0.0020(4) -0.0016(4) 0.0008(4) C5 0.0272(6) 0.0204(5) 0.0209(5) -0.0035(4) 0.0076(4) 0.0018(4) C6 0.0206(5) 0.0185(5) 0.0192(5) -0.0003(4) 0.0074(4) -0.0003(4) C7 0.0164(4) 0.0148(5) 0.0130(4) -0.0001(3) 0.0013(3) -0.0034(4) C8 0.0294(6) 0.0241(6) 0.0183(5) 0.0030(4) 0.0001(4) 0.0052(5) C9 0.0443(8) 0.0299(7) 0.0183(5) 0.0069(5) -0.0035(5) 0.0019(6) C10 0.0395(7) 0.0283(6) 0.0134(4) -0.0004(4) 0.0035(4) -0.0138(5) C11 0.0275(6) 0.0400(7) 0.0184(5) -0.0051(5) 0.0089(4) -0.0040(5) C12 0.0212(5) 0.0329(6) 0.0163(5) -0.0006(4) 0.0038(4) 0.0043(5) C13 0.0140(4) 0.0134(4) 0.0147(4) 0.0019(3) 0.0018(3) 0.0000(3) C14 0.0209(5) 0.0124(4) 0.0180(5) -0.0004(3) 0.0005(4) -0.0002(4) C15 0.0223(5) 0.0119(4) 0.0189(5) 0.0001(4) 0.0043(4) 0.0000(4) C16 0.0253(6) 0.0201(6) 0.0256(6) 0.0014(4) -0.0012(4) 0.0028(4) C17 0.0166(5) 0.0139(4) 0.0160(4) 0.0012(3) 0.0030(4) 0.0031(4) C18 0.0267(5) 0.0210(6) 0.0190(5) -0.0025(4) 0.0063(4) -0.0057(4) C19 0.0305(6) 0.0225(5) 0.0225(5) -0.0043(4) 0.0037(4) -0.0070(5) C20 0.0328(6) 0.0255(6) 0.0200(5) -0.0070(5) 0.0028(4) 0.0018(5) C21 0.0305(6) 0.0463(9) 0.0223(5) -0.0102(5) 0.0122(5) -0.0030(6) C22 0.0209(5) 0.0350(7) 0.0224(5) -0.0053(5) 0.0082(4) -0.0042(5) P2 0.02071(14) 0.01710(13) 0.03395(16) -0.00012(12) 0.01285(11) 0.00006(11) O2 0.0200(4) 0.0252(4) 0.0330(5) -0.0046(4) 0.0105(3) 0.0002(3) N2 0.0185(4) 0.0293(6) 0.0307(5) 0.0037(4) 0.0039(4) -0.0003(4) C23 0.0233(14) 0.0179(12) 0.0175(14) -0.0034(11) 0.0039(12) -0.0022(10) C24 0.0313(13) 0.0252(12) 0.0248(11) 0.0009(9) 0.0008(9) -0.0060(10) C25 0.0461(16) 0.0280(13) 0.0261(12) 0.0056(10) 0.0032(11) -0.0102(12) C26 0.0471(18) 0.0291(15) 0.0288(14) 0.0074(12) 0.0093(12) 0.0026(13) C27 0.0359(18) 0.0422(18) 0.0324(15) 0.0047(12) 0.0053(14) 0.0038(16) C28 0.0301(16) 0.0343(14) 0.0283(13) 0.0063(11) 0.0065(12) 0.0044(12) C23X 0.0220(14) 0.0221(15) 0.0197(15) 0.0007(12) 0.0010(12) 0.0006(10) C24X 0.0342(15) 0.0232(13) 0.0418(16) 0.0073(11) -0.0006(12) -0.0039(11) C25X 0.0457(19) 0.0246(14) 0.059(2) 0.0128(14) 0.0041(16) -0.0027(13) C26X 0.0375(17) 0.0338(16) 0.053(2) 0.0216(15) 0.0097(14) 0.0068(13) C27X 0.039(2) 0.042(2) 0.0302(15) 0.0179(15) 0.0041(15) 0.0085(17) C28X 0.0288(17) 0.0407(17) 0.0253(14) 0.0042(12) 0.0048(14) 0.0076(13) C29 0.025(3) 0.011(3) 0.037(2) -0.0072(15) 0.0198(18) -0.0026(16) C30 0.028(3) 0.0381(19) 0.0323(19) 0.0020(14) -0.0089(18) -0.004(2) C31 0.043(3) 0.052(2) 0.0225(16) 0.0035(14) -0.0078(18) -0.006(2) C32 0.061(5) 0.043(3) 0.018(2) -0.006(2) 0.006(2) -0.029(3) C33 0.055(3) 0.040(3) 0.026(2) -0.004(2) 0.0200(19) -0.001(2) C34 0.0374(17) 0.037(2) 0.0288(19) 0.0078(18) 0.0113(14) 0.0088(15) C29X 0.030(3) 0.021(5) 0.043(3) -0.015(2) 0.0131(18) -0.008(2) C30X 0.029(3) 0.069(3) 0.0217(17) -0.0034(17) 0.0040(18) 0.015(3) C31X 0.031(3) 0.141(6) 0.030(2) 0.007(3) -0.0040(18) 0.014(3) C32X 0.052(4) 0.054(4) 0.023(3) -0.013(3) 0.013(3) -0.027(3) C33X 0.097(3) 0.027(2) 0.033(2) 0.0022(17) 0.036(2) 0.012(2) C34X 0.058(2) 0.034(2) 0.0259(19) -0.0026(16) 0.0166(15) 0.0169(17) C35 0.0320(7) 0.0261(6) 0.0325(7) 0.0093(5) -0.0114(5) -0.0084(5) C36 0.039(2) 0.0186(16) 0.0224(13) 0.0084(11) -0.0043(13) -0.0016(13) C37 0.0384(16) 0.0221(13) 0.0353(15) 0.0039(10) 0.0012(12) -0.0024(11) C38 0.053(2) 0.0418(19) 0.0400(18) 0.0024(14) 0.0099(15) 0.0003(16) C36X 0.039(2) 0.0247(18) 0.0296(15) 0.0066(12) -0.0043(14) 0.0029(14) C37X 0.0389(16) 0.0416(16) 0.0206(12) 0.0043(11) 0.0005(10) -0.0047(13) C38X 0.076(3) 0.064(3) 0.041(2) 0.0175(18) -0.0107(19) 0.013(2) C39 0.0236(6) 0.0267(6) 0.0243(5) 0.0085(5) -0.0006(4) -0.0050(5) C40 0.0221(6) 0.0312(7) 0.0393(7) 0.0118(6) -0.0038(5) 0.0012(5) C41 0.0309(7) 0.0301(7) 0.0417(8) 0.0076(6) 0.0037(6) 0.0069(6) C42 0.0316(7) 0.0295(7) 0.0269(6) 0.0040(5) 0.0023(5) 0.0007(5) C43 0.0246(6) 0.0363(7) 0.0241(6) 0.0024(5) -0.0011(5) 0.0024(5) C44 0.0239(6) 0.0343(7) 0.0238(6) 0.0012(5) 0.0013(5) 0.0040(5) _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 1.4887(8) . ? P1 N1 1.6541(9) . ? P1 C7 1.8005(10) . ? P1 C1 1.8133(11) . ? N1 C13 1.4743(13) . ? N1 H1N 0.871(13) . ? C1 C6 1.3951(15) . ? C1 C2 1.3961(15) . ? C2 C3 1.3944(16) . ? C2 H2 0.9500 . ? C3 C4 1.3889(17) . ? C3 H3 0.9500 . ? C4 C5 1.3857(18) . ? C4 H4 0.9500 . ? C5 C6 1.3968(16) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.3949(15) . ? C7 C12 1.3958(15) . ? C8 C9 1.3914(17) . ? C8 H8 0.9500 . ? C9 C10 1.384(2) . ? C9 H9 0.9500 . ? C10 C11 1.383(2) . ? C10 H10 0.9500 . ? C11 C12 1.3962(16) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.5184(15) . ? C13 C17 1.5194(15) . ? C13 H13 1.0000 . ? C14 C15 1.3048(16) . ? C14 H14 0.9500 . ? C15 C16 1.3003(16) . ? C16 H16A 0.931(14) . ? C16 H16B 0.932(14) . ? C17 C22 1.3859(16) . ? C17 C18 1.3916(16) . ? C18 C19 1.3927(16) . ? C18 H18 0.9500 . ? C19 C20 1.3829(18) . ? C19 H19 0.9500 . ? C20 C21 1.379(2) . ? C20 H20 0.9500 . ? C21 C22 1.3960(18) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? P2 O2 1.4878(9) . ? P2 N2 1.6421(12) . ? P2 C29 1.830(5) . ? P2 C23 1.850(3) . ? N2 C35 1.4630(18) . ? N2 H2N 0.904(14) . ? C23 C24 1.393(4) . ? C23 C28 1.396(5) . ? C24 C25 1.401(4) . ? C24 H24 0.9500 . ? C25 C26 1.374(5) . ? C25 H25 0.9500 . ? C26 C27 1.384(5) . ? C26 H26 0.9500 . ? C27 C28 1.388(4) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C34 1.434(8) . ? C29 C30 1.458(9) . ? C30 C31 1.386(7) . ? C30 H30 0.9500 . ? C31 C32 1.380(10) . ? C31 H31 0.9500 . ? C32 C33 1.373(8) . ? C32 H32 0.9500 . ? C33 C34 1.389(6) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C39 1.520(2) . ? C35 C36 1.623(4) . ? C35 H35 0.88(2) . ? C36 C37 1.313(4) . ? C36 H36 0.9500 . ? C37 C38 1.263(5) . ? C38 H38A 0.95(2) . ? C38 H38B 0.96(2) . ? C39 C40 1.386(2) . ? C39 C44 1.3883(18) . ? C40 C41 1.383(2) . ? C40 H40 0.9500 . ? C41 C42 1.385(2) . ? C41 H41 0.9500 . ? C42 C43 1.390(2) . ? C42 H42 0.9500 . ? C43 C44 1.393(2) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? 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 N1 111.70(5) . . ? O1 P1 C7 114.31(5) . . ? N1 P1 C7 104.42(5) . . ? O1 P1 C1 110.15(5) . . ? N1 P1 C1 110.70(5) . . ? C7 P1 C1 105.27(5) . . ? C13 N1 P1 119.56(7) . . ? C13 N1 H1N 113.9(10) . . ? P1 N1 H1N 117.5(11) . . ? C6 C1 C2 119.04(10) . . ? C6 C1 P1 119.77(8) . . ? C2 C1 P1 121.18(8) . . ? C3 C2 C1 120.35(10) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 120.13(11) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.01(11) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.96(11) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 120.50(11) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C12 119.46(10) . . ? C8 C7 P1 116.89(9) . . ? C12 C7 P1 123.64(8) . . ? C9 C8 C7 120.11(12) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 120.33(12) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 119.90(11) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.40(12) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C7 C12 C11 119.80(11) . . ? C7 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? N1 C13 C14 107.65(9) . . ? N1 C13 C17 113.66(8) . . ? C14 C13 C17 114.01(9) . . ? N1 C13 H13 107.0 . . ? C14 C13 H13 107.0 . . ? C17 C13 H13 107.0 . . ? C15 C14 C13 127.09(10) . . ? C15 C14 H14 116.5 . . ? C13 C14 H14 116.5 . . ? C16 C15 C14 175.48(12) . . ? C15 C16 H16A 123.3(12) . . ? C15 C16 H16B 119.3(12) . . ? H16A C16 H16B 117.4(16) . . ? C22 C17 C18 118.65(10) . . ? C22 C17 C13 120.28(10) . . ? C18 C17 C13 121.04(9) . . ? C17 C18 C19 120.60(11) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.27(12) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 119.49(11) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 120.36(12) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C17 C22 C21 120.60(12) . . ? C17 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? O2 P2 N2 111.96(6) . . ? O2 P2 C29 106.6(3) . . ? N2 P2 C29 111.2(6) . . ? O2 P2 C23 112.41(11) . . ? N2 P2 C23 97.59(12) . . ? C29 P2 C23 117.0(5) . . ? C35 N2 P2 118.83(9) . . ? C35 N2 H2N 115.8(12) . . ? P2 N2 H2N 115.8(12) . . ? C24 C23 C28 118.2(3) . . ? C24 C23 P2 114.8(2) . . ? C28 C23 P2 127.0(2) . . ? C23 C24 C25 121.0(3) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C26 C25 C24 119.2(3) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? C25 C26 C27 121.0(3) . . ? C25 C26 H26 119.5 . . ? C27 C26 H26 119.5 . . ? C26 C27 C28 119.5(4) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C27 C28 C23 121.0(4) . . ? C27 C28 H28 119.5 . . ? C23 C28 H28 119.5 . . ? C34 C29 C30 113.0(5) . . ? C34 C29 P2 123.4(6) . . ? C30 C29 P2 123.6(6) . . ? C31 C30 C29 121.9(5) . . ? C31 C30 H30 119.1 . . ? C29 C30 H30 119.1 . . ? C32 C31 C30 121.2(5) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C33 C32 C31 120.1(6) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 119.8(5) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C33 C34 C29 123.9(5) . . ? C33 C34 H34 118.1 . . ? C29 C34 H34 118.1 . . ? N2 C35 C39 111.90(11) . . ? N2 C35 C36 102.27(19) . . ? C39 C35 C36 111.49(17) . . ? N2 C35 H35 111.0(14) . . ? C39 C35 H35 97.7(14) . . ? C36 C35 H35 122.8(14) . . ? C37 C36 C35 125.4(3) . . ? C37 C36 H36 117.3 . . ? C35 C36 H36 117.3 . . ? C38 C37 C36 176.5(4) . . ? C37 C38 H38A 114(3) . . ? C37 C38 H38B 126(3) . . ? H38A C38 H38B 120(4) . . ? C37 C38 H38D 105.7(16) . . ? H38A C38 H38D 67(4) . . ? H38B C38 H38D 102(3) . . ? C40 C39 C44 119.41(13) . . ? C40 C39 C35 120.26(12) . . ? C44 C39 C35 120.31(13) . . ? C41 C40 C39 120.77(13) . . ? C41 C40 H40 119.6 . . ? C39 C40 H40 119.6 . . ? C40 C41 C42 120.24(14) . . ? C40 C41 H41 119.9 . . ? C42 C41 H41 119.9 . . ? C41 C42 C43 119.21(14) . . ? C41 C42 H42 120.4 . . ? C43 C42 H42 120.4 . . ? C42 C43 C44 120.62(13) . . ? C42 C43 H43 119.7 . . ? C44 C43 H43 119.7 . . ? C39 C44 C43 119.74(13) . . ? C39 C44 H44 120.1 . . ? C43 C44 H44 120.1 . . ? 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 N1 C13 -36.01(9) . . . . ? C7 P1 N1 C13 -160.05(8) . . . . ? C1 P1 N1 C13 87.13(9) . . . . ? O1 P1 C1 C6 16.16(10) . . . . ? N1 P1 C1 C6 -107.88(9) . . . . ? C7 P1 C1 C6 139.85(9) . . . . ? O1 P1 C1 C2 -165.21(8) . . . . ? N1 P1 C1 C2 70.76(10) . . . . ? C7 P1 C1 C2 -41.52(10) . . . . ? C6 C1 C2 C3 -0.66(16) . . . . ? P1 C1 C2 C3 -179.31(9) . . . . ? C1 C2 C3 C4 0.95(17) . . . . ? C2 C3 C4 C5 -0.16(18) . . . . ? C3 C4 C5 C6 -0.90(18) . . . . ? C2 C1 C6 C5 -0.41(16) . . . . ? P1 C1 C6 C5 178.26(9) . . . . ? C4 C5 C6 C1 1.19(18) . . . . ? O1 P1 C7 C8 53.15(11) . . . . ? N1 P1 C7 C8 175.50(9) . . . . ? C1 P1 C7 C8 -67.85(10) . . . . ? O1 P1 C7 C12 -125.63(10) . . . . ? N1 P1 C7 C12 -3.28(11) . . . . ? C1 P1 C7 C12 113.37(10) . . . . ? C12 C7 C8 C9 0.55(18) . . . . ? P1 C7 C8 C9 -178.29(10) . . . . ? C7 C8 C9 C10 -0.5(2) . . . . ? C8 C9 C10 C11 0.0(2) . . . . ? C9 C10 C11 C12 0.3(2) . . . . ? C8 C7 C12 C11 -0.20(18) . . . . ? P1 C7 C12 C11 178.55(10) . . . . ? C10 C11 C12 C7 -0.2(2) . . . . ? P1 N1 C13 C14 149.02(8) . . . . ? P1 N1 C13 C17 -83.71(10) . . . . ? N1 C13 C14 C15 114.57(13) . . . . ? C17 C13 C14 C15 -12.49(17) . . . . ? N1 C13 C17 C22 138.94(11) . . . . ? C14 C13 C17 C22 -97.18(13) . . . . ? N1 C13 C17 C18 -39.29(14) . . . . ? C14 C13 C17 C18 84.59(13) . . . . ? C22 C17 C18 C19 -1.08(18) . . . . ? C13 C17 C18 C19 177.18(11) . . . . ? C17 C18 C19 C20 0.2(2) . . . . ? C18 C19 C20 C21 0.7(2) . . . . ? C19 C20 C21 C22 -0.8(2) . . . . ? C18 C17 C22 C21 1.00(19) . . . . ? C13 C17 C22 C21 -177.27(12) . . . . ? C20 C21 C22 C17 -0.1(2) . . . . ? O2 P2 N2 C35 47.22(13) . . . . ? C29 P2 N2 C35 -71.9(4) . . . . ? C23 P2 N2 C35 165.15(14) . . . . ? O2 P2 C23 C24 -33.6(3) . . . . ? N2 P2 C23 C24 -151.2(2) . . . . ? C23X P2 C23 C24 66.9(6) . . . . ? C29X P2 C23 C24 92.4(6) . . . . ? C29 P2 C23 C24 90.2(6) . . . . ? O2 P2 C23 C28 144.9(3) . . . . ? N2 P2 C23 C28 27.3(3) . . . . ? C29 P2 C23 C28 -91.2(6) . . . . ? C28 C23 C24 C25 3.1(5) . . . . ? P2 C23 C24 C25 -178.2(2) . . . . ? C23 C24 C25 C26 -1.1(4) . . . . ? C24 C25 C26 C27 -1.6(5) . . . . ? C25 C26 C27 C28 2.2(5) . . . . ? C26 C27 C28 C23 0.0(5) . . . . ? C24 C23 C28 C27 -2.6(5) . . . . ? P2 C23 C28 C27 178.9(3) . . . . ? O2 P2 C29 C34 174.0(11) . . . . ? N2 P2 C29 C34 -63.7(14) . . . . ? C23 P2 C29 C34 47.2(15) . . . . ? O2 P2 C29 C30 -4.5(14) . . . . ? N2 P2 C29 C30 117.8(12) . . . . ? C23 P2 C29 C30 -131.3(11) . . . . ? C34 C29 C30 C31 0.8(17) . . . . ? P2 C29 C30 C31 179.5(8) . . . . ? C29 C30 C31 C32 -2.9(13) . . . . ? C30 C31 C32 C33 1.4(12) . . . . ? C31 C32 C33 C34 2.1(12) . . . . ? C32 C33 C34 C29 -4.3(12) . . . . ? C30 C29 C34 C33 2.7(17) . . . . ? P2 C29 C34 C33 -175.9(7) . . . . ? P2 N2 C35 C39 -131.93(11) . . . . ? P2 N2 C35 C36 108.63(17) . . . . ? N2 C35 C36 C37 -103.3(4) . . . . ? C39 C35 C36 C37 137.0(3) . . . . ? N2 C35 C39 C40 134.84(14) . . . . ? C36 C35 C39 C40 -111.3(2) . . . . ? N2 C35 C39 C44 -46.53(18) . . . . ? C36 C35 C39 C44 67.3(2) . . . . ? C44 C39 C40 C41 0.0(2) . . . . ? C35 C39 C40 C41 178.60(13) . . . . ? C39 C40 C41 C42 -0.4(2) . . . . ? C40 C41 C42 C43 0.6(2) . . . . ? C41 C42 C43 C44 -0.4(2) . . . . ? C40 C39 C44 C43 0.2(2) . . . . ? C35 C39 C44 C43 -178.42(13) . . . . ? C42 C43 C44 C39 0.0(2) . . . . ? 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 N1 H1N O1 0.871(13) 2.104(13) 2.9751(12) 177.4(16) 1_655 N2 H2N O2 0.904(14) 1.992(15) 2.8755(14) 165.6(18) 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.543 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.041