#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/14/2001480.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2001480
loop_
_publ_author_name
'Koeller, K. J.'
'Rath, N. P.'
'Spilling, C. D.'
_publ_section_title
;
 Structure of a chiral bicyclic 1-hydroxyalkyl phosphonamide
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1547
_journal_page_last               1549
_journal_paper_doi               10.1107/S0108270193001507
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C25 H41 N2 O2 P'
_chemical_formula_weight         432.6
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.0
_cell_angle_beta                 116.68(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   26.304(11)
_cell_length_b                   12.639(6)
_cell_length_c                   16.825(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     4998(4)
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6456
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 50
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       Irregular
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.25
_refine_ls_goodness_of_fit_obs   1.15
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2340
_refine_ls_R_factor_obs          0.062
_refine_ls_shift/esd_max         0.006
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = [σ²F + 0.0009F²]⁻¹'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.065
_reflns_number_observed          2340
_reflns_number_total             5983
_reflns_observed_criterion       F>3\s(F)
_cod_data_source_file            st1044.cif
_cod_data_source_block           st1044a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '[\s^2^F + 0.0009F^2^]^-1^' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = [\s^2^F +
0.0009F^2^]^-1^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2001480
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
P .30740(10) .18570(10) .91660(10) .0420(10)
O(1) .27760(10) .2853(2) .9032(2) .0530(10)
O(2) .24360(10) .0984(3) .9830(2) .071(2)
N(1) .37620(10) .1929(3) .9419(2) .041(2)
N(2) .28940(10) .1095(3) .8301(2) .043(2)
C(1) .3863(2) .1339(4) .8747(3) .054(2)
C(2) .3402(2) .0568(4) .8358(3) .050(2)
C(3) .3401(2) .0052(4) .7567(3) .067(3)
C(4) .3971(2) -.0395(5) .7780(4) .078(3)
C(5) .4455(2) .0339(5) .8232(4) .083(3)
C(6) .4433(2) .0891(4) .9004(3) .069(3)
C(7) .4043(2) .2948(4) .9668(3) .060(2)
C(8) .4435(2) .3123(4) 1.0626(3) .062(2)
C(9) .4717(3) .4153(5) 1.0688(5) .111(4)
C(10) .4877(3) .2304(5) 1.0995(4) .123(4)
C(11) .4105(3) .3177(6) 1.1175(4) .110(4)
C(12) .2348(2) .0544(4) .7929(3) .058(2)
C(13) .1894(2) .0970(5) .7072(3) .066(3)
C(14) .1364(3) .0352(6) .6863(4) .128(4)
C(15) .2050(3) .0841(6) .6321(4) .106(4)
C(16) .1770(3) .2072(6) .7171(4) .146(4)
C(17) .3014(2) .1170(4) 1.0079(3) .049(2)
C(18) .3355(2) .0193(4) 1.0336(3) .050(2)
C(19) .3160(2) -.0736(4) 1.0353(3) .054(2)
C(20) .3495(2) -.1678(4) 1.0678(3) .057(3)
C(21) .4040(3) -.1770(5) 1.0814(4) .090(4)
C(22) .4348(3) -.2650(6) 1.1180(5) .115(5)
C(23) .4115(4) -.3452(5) 1.1416(5) .104(5)
C(24) .3572(4) -.3377(6) 1.1269(5) .106(5)
C(25) .3260(3) -.2511(5) 1.0906(4) .079(3)
H(2A) .2338 .1333 1.0171 ?
H(1B) .3797 .1829 .8275 ?
H(2B) .3496 .0020 .8796 ?
H(3A) .3312 .0582 .7115 ?
H(3B) .3112 -.0486 .7345 ?
H(4A) .3974 -.0661 .7248 ?
H(4B) .4029 -.0984 .8172 ?
H(5A) .4439 .0862 .7807 ?
H(5B) .4809 -.0036 .8427 ?
H(6A) .4513 .0391 .9475 ?
H(6B) .4715 .1440 .9222 ?
H(7A) .3755 .3486 .9479 ?
H(7B) .4260 .3049 .9343 ?
H(9A) .4932 .4121 1.0353 ?
H(9B) .4435 .4699 1.0450 ?
H(9C) .4968 .4305 1.1299 ?
H(10A) .5079 .2284 1.0642 ?
H(10B) .5136 .2470 1.1600 ?
H(10C) .4705 .1627 1.0973 ?
H(11A) .3918 .2514 1.1142 ?
H(11B) .4359 .3334 1.1785 ?
H(11C) .3825 .3728 1.0935 ?
H(12A) .2206 .0546 .8364 ?
H(12B) .2412 -.0179 .7823 ?
H(14A) .1250 .0441 .7326 ?
H(14B) .1062 .0575 .6306 ?
H(14C) .1448 -.0380 .6825 ?
H(15A) .2383 .1252 .6436 ?
H(15B) .2130 .0106 .6286 ?
H(15C) .1743 .1061 .5768 ?
H(16A) .1669 .2121 .7651 ?
H(16B) .2101 .2496 .7305 ?
H(16C) .1460 .2322 .6633 ?
H(17A) .3157 .1633 1.0585 ?
H(18A) .3755 .0244 1.0503 ?
H(19A) .2755 -.0800 1.0123 ?
H(21A) .4210 -.1192 1.0650 ?
H(22A) .4735 -.2700 1.1271 ?
H(23A) .4332 -.4079 1.1677 ?
H(24A) .3403 -.3958 1.1431 ?
H(25A) .2871 -.2475 1.0807 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O(1) P N(1) 116.4(2) yes
N(1) P N(2) 96.2(2) yes
N(1) P C(17) 107.7(2) yes
P N(1) C(1) 109.0(2) yes
C(1) N(1) C(7) 115.4(4) yes
P N(2) C(12) 120.1(4) yes
N(1) C(1) C(2) 106.5(5) yes
C(2) C(1) C(6) 113.9(4) yes
N(2) C(2) C(3) 120.6(3) yes
C(2) C(3) C(4) 110.8(4) yes
C(4) C(5) C(6) 112.2(6) yes
N(1) C(7) C(8) 117.4(4) yes
C(7) C(8) C(10) 112.6(5) yes
C(7) C(8) C(11) 110.9(4) yes
C(10) C(8) C(11) 109.4(5) yes
C(12) C(13) C(14) 107.1(5) yes
C(14) C(13) C(15) 108.9(5) yes
C(14) C(13) C(16) 107.0(6) yes
P C(17) O(2) 108.6(3) yes
O(2) C(17) C(18) 112.6(4) yes
C(18) C(19) C(20) 125.7(5) yes
C(19) C(20) C(25) 118.1(6) yes
C(20) C(21) C(22) 121.5(7) yes
C(22) C(23) C(24) 119.0(7) yes
C(20) C(25) C(24) 119.9(7) yes
O(1) P N(2) 117.1(2) yes
O(1) P C(17) 107.3(2) yes
N(2) P C(17) 111.6(2) yes
P N(1) C(7) 118.4(3) yes
P N(2) C(2) 108.7(2) yes
C(2) N(2) C(12) 120.5(4) yes
N(1) C(1) C(6) 118.6(4) yes
N(2) C(2) C(1) 106.1(4) yes
C(1) C(2) C(3) 111.4(5) yes
C(3) C(4) C(5) 115.4(5) yes
C(1) C(6) C(5) 110.8(4) yes
C(7) C(8) C(9) 106.8(5) yes
C(9) C(8) C(10) 108.2(5) yes
C(9) C(8) C(11) 108.8(6) yes
N(2) C(12) C(13) 116.5(4) yes
C(12) C(13) C(15) 111.7(5) yes
C(12) C(13) C(16) 110.8(4) yes
C(15) C(13) C(16) 111.1(6) yes
P C(17) C(18) 111.9(4) yes
C(17) C(18) C(19) 125.1(5) yes
C(19) C(20) C(21) 124.0(6) yes
C(21) C(20) C(25) 117.8(5) yes
C(21) C(22) C(23) 120.0(8) yes
C(23) C(24) C(25) 121.7(8) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P O(1) 1.446(3) yes
P N(2) 1.628(4) yes
O(2) C(17) 1.404(6) yes
N(1) C(7) 1.450(6) yes
N(2) C(12) 1.459(6) yes
C(1) C(6) 1.475(7) yes
C(3) C(4) 1.489(8) yes
C(5) C(6) 1.499(10) yes
C(8) C(9) 1.479(9) yes
C(8) C(11) 1.526(10) yes
C(13) C(14) 1.496(9) yes
C(13) C(16) 1.457(9) yes
C(18) C(19) 1.286(7) yes
C(20) C(21) 1.350(10) yes
C(21) C(22) 1.351(10) yes
C(23) C(24) 1.340(14) yes
P N(1) 1.664(4) yes
P C(17) 1.833(6) yes
N(1) C(1) 1.473(7) yes
N(2) C(2) 1.458(6) yes
C(1) C(2) 1.460(6) yes
C(2) C(3) 1.480(8) yes
C(4) C(5) 1.481(8) yes
C(7) C(8) 1.490(6) yes
C(8) C(10) 1.469(8) yes
C(12) C(13) 1.500(6) yes
C(13) C(15) 1.502(10) yes
C(17) C(18) 1.472(7) yes
C(19) C(20) 1.435(7) yes
C(20) C(25) 1.360(9) yes
C(22) C(23) 1.333(13) yes
C(24) C(25) 1.338(9) yes
