data_2010382
_journal_name_full  'Acta Crystallographica'
_journal_year  1995
_journal_volume  C51
_journal_page_first  86
_journal_page_last  88
_publ_section_title
;
A Chiral Bicyclic 1-Acetoxy Phosphonamide
;
loop_
_publ_author_name
  'Blazis, Vincent J.'
  'Koeller, Kevin J.'
  'Rath, Nigam P.'
  'Spilling, Christopher D.'
_chemical_formula_moiety  'C23 H45 N2 O3 P'
_chemical_formula_sum  'C23 H45 N2 O3 P'
_chemical_formula_weight  428.6
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '1/2-x,-y,1/2+z'
  '-x,1/2+y,1/2-z'
  '1/2+x,1/2-y,-z'
_cell_length_a  9.970(2)
_cell_length_b  14.049(3)
_cell_length_c  19.013(4)
_cell_angle_alpha  90.
_cell_angle_beta  90.
_cell_angle_gamma  90.
_cell_volume  2663.1(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  298
_exptl_crystal_density_meas  1.069
_refine_ls_R_factor_obs  0.0495
_refine_ls_wR_factor_obs  0.0593
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
  P .90710(10)
  .77090(10)
  .77310(10)
  .0420(10)
  O(1) .9602(2) .6732(2) .77360(10)
  .0530(10)
  O(2) .8016(3) .8880(2) .67610(10)
  .0550(10)
  O(3) .9396(4) .9058(2) .5838(2) .0880(10)
  N(1) .7927(3) .8014(2) .83230(10)
  .0460(10)
  N(2) 1.0116(3) .8601(2) .79190(10)
  .0440(10)
  C(1) .8315(3) .8875(2) .8714(2) .0450(10)
  C(2) .7223(4) .9563(3) .8923(2) .0650(10)
  C(3) .7869(4) 1.0373(3) .9332(2) .060(10)
  C(4) .8998(5) 1.0848(3) .8926(2) .0720(10)
  C(5) 1.0044(4) 1.0142(2) .8655(2) .0560(10)
  C(6) .9316(3) .9379(2) .8241(2) .0460(10)
  C(7) .6845(3) .7383(3) .8546(2) .0530(10)
  C(8) .6953(4) .6834(3) .9250(2) .0630(10)
  C(9) .8254(5) .6285(4) .9279(3) .102(2)
  C(10) .6838(6) .7481(3) .9889(2) .093(2)
  C(11) .5763(5) .6161(3) .9259(3) .100(2)
  C(12) 1.1181(3) .8877(3) .7417(2) .0540(10)
  C(13) 1.2618(3) .8617(3) .7635(2) .0620(10)
  C(14) 1.3540(5) .8991(5) .7074(3) .136(3)
  C(15) 1.3015(5) .9111(4) .8308(3) .105(2)
  C(16) 1.2785(4) .7573(3) .7723(3) .093(2)
  C(17) .8369(4) .7890(2) .6839(2) .0440(10)
  C(18) .8620(5) .9395(3) .6242(2) .0640(10)
  C(19) .8159(6) 1.0402(3) .6275(2) .094(2)
  C(20) .7157(3) .7283(3) .6695(2) .0540(10)
  C(21) .6604(4) .7312(3) .5938(2) .0670(10)
  C(22) .7565(5) .6930(3) .5408(2) .093(2)
  C(23) .5315(5) .6743(4) .5905(3) .104(2)
  H(1) .875(3)  .8681(19) .9155(15) .038(8)
  H(2A) .6559 .9250 .9207 .080
  H(2B) .6794 .9809 .8509 .080
  H(3A) .8217 1.0125 .9765 .080
  H(3B) .7201 1.0841 .9444 .080
  H(4A) .9433 1.1304 .9225 .080
  H(4B) .8625 1.1188 .8534 .080
  H(5A) 1.0520 .9861 .9042 .080
  H(5B) 1.0679 1.0461 .8358 .080
  H(6) .887(3)  .976(2)  .7844(16) .051(9)
  H(7A) .6709 .6923 .8179 .080
  H(7B) .6046 .7762 .8569 .080
  H(9A) .8303 .5947 .9717 .080
  H(9B) .8283 .5840 .8896 .080
  H(9C) .9000 .6715 .9243 .080
  H(10A) .6909 .7119 1.0316 .080
  H(10B) .7540 .7948 .9875 .080
  H(10C) .5983 .7794 .9874 .080
  H(11A) .5777 .5796 .9686 .080
  H(11B) .4951 .6528 .9239 .080
  H(11C) .5801 .5739 .8863 .080
  H(12A) 1.1136 .9552 .7343 .080
  H(12B) 1.0994 .8574 .6975 .080
  H(14A) 1.4459 .8852 .7183 .080
  H(14B) 1.3309 .8705 .6632 .080
  H(14C) 1.3420 .9668 .7045 .080
  H(15A) 1.3917 .8942 .8434 .080
  H(15B) 1.2957 .9787 .8244 .080
  H(15C) 1.2414 .8918 .8676 .080
  H(16A) 1.3692 .7435 .7859 .080
  H(16B) 1.2182 .7350 .8081 .080
  H(16C) 1.2586 .7259 .7287 .080
  H(17) .906(3)  .775(2)  .6551(15) .35(8)
  H(19A) .8595 1.0752 .5907 .080
  H(19B) .7206 1.0427 .6209 .080
  H(19C) .8385 1.0677 .6722 .080
  H(20A) .6455 .7475 .7010 .080
  H(20B) .7375 .6634 .6804 .080
  H(21) .6398 .7961 .5822 .080
  H(22A) .7179 .6969 .4947 .080
  H(22B) .8375 .7299 .5423 .080
  H(22C) .7767 .6277 .5516 .080
  H(23C) .4957 .6758 .5436 .080
  H(23A) .5506 .6097 .6035 .080
  H(23B) .4672 .7007 .6226 .080
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  P O(1) . . 1.471(2) yes
  P N(2) . . 1.669(3) yes
  O(2) C(17) . . 1.442(4) yes
  O(3) C(18) . . 1.189(5) yes
  N(1) C(7) . . 1.459(4) yes
  N(2) C(12) . . 1.479(4) yes
  C(1) C(6) . . 1.519(5) yes
  C(3) C(4) . . 1.520(6) yes
  C(5) C(6) . . 1.516(5) yes
  C(8) C(9) . . 1.510(7) yes
  C(8) C(11) . . 1.517(6) yes
  C(13) C(14) . . 1.503(7) yes
  C(13) C(16) . . 1.486(6) yes
  C(18) C(19) . . 1.488(6) yes
  C(21) C(22) . . 1.491(6) yes
  P N(1) . . 1.659(3) yes
  P C(17) . . 1.853(3) yes
  O(2) C(18) . . 1.364(5) yes
  N(1) C(1) . . 1.472(4) yes
  N(2) C(6) . . 1.484(4) yes
  C(1) C(2) . . 1.508(5) yes
  C(2) C(3) . . 1.521(5) yes
  C(4) C(5) . . 1.529(5) yes
  C(7) C(8) . . 1.550(5) yes
  C(8) C(10) . . 1.522(5) yes
  C(12) C(13) . . 1.535(5) yes
  C(13) C(15) . . 1.508(7) yes
  C(17) C(20) . . 1.504(5) yes
  C(20) C(21) . . 1.542(5) yes
  C(21) C(23) . . 1.514(7) yes