#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:54:25 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180160 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/56/7105603.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7105603
loop_
_publ_author_name
'Bryant, David E.'
'Marriott, Katie E. R.'
'Macgregor, Stuart A.'
'Kilner, Colin'
'Pasek, Matthew A.'
'Kee, Terence P.'
_publ_section_title
;
 On the prebiotic potential of reduced oxidation state phosphorus: the
 H-phosphinate-pyruvate system.
;
_journal_issue                   21
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3726
_journal_page_last               3728
_journal_paper_doi               10.1039/c002689a
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C27 H38 N3 O8 P'
_chemical_formula_weight         563.57
_chemical_name_common
;benzylamine (benzylamino-2-hydroxypropionato)-2-
hydroxypropionato phosphonate
;
_chemical_name_systematic
;
benzylamine (benzylamino-2-hydroxypropionato)-2-hydroxypropionato phosphonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.470(7)
_cell_angle_beta                 100.513(7)
_cell_angle_gamma                99.949(7)
_cell_formula_units_Z            2
_cell_length_a                   10.1313(13)
_cell_length_b                   10.6117(15)
_cell_length_c                   14.621(2)
_cell_measurement_reflns_used    32061
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.87
_cell_measurement_theta_min      1.99
_cell_volume                     1490.8(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean
;
120 microns
;
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32061
_diffrn_reflns_theta_full        26.87
_diffrn_reflns_theta_max         26.87
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Using multiple and symmetry-related data measurements via the program SORTAV
See R.H. Blessing, Acta Cryst (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         6339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.4321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                5087
_reflns_number_total             6339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c002689a.txt
_cod_data_source_block
m:\docume~1\davidb\mydocu~1\x-ray\xray\deb154c\deb154c
_cod_original_cell_volume        1490.7(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7105603
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.29166(3) 0.65175(3) 0.43904(2) 0.01410(9) Uani 1 1 d . . .
O1 O 0.16127(9) 0.54504(9) 0.41397(7) 0.0177(2) Uani 1 1 d . . .
O2 O 0.34982(10) 0.91352(9) 0.42995(7) 0.0212(2) Uani 1 1 d . . .
O3 O 0.37909(9) 0.67456(9) 0.53889(7) 0.0194(2) Uani 1 1 d . . .
O4 O 0.13599(11) 0.26810(11) 0.37012(8) 0.0249(2) Uani 1 1 d . . .
O5 O 0.41274(11) 0.47237(9) 0.36531(8) 0.0248(2) Uani 1 1 d . . .
O6 O 0.05244(10) 0.77457(9) 0.50963(7) 0.0219(2) Uani 1 1 d . . .
N7 N 0.12948(13) 0.47223(12) 0.58958(9) 0.0186(2) Uani 1 1 d . . .
O8 O 0.55638(10) 0.81732(10) 0.40035(9) 0.0321(3) Uani 1 1 d . . .
O9 O 0.64965(11) 0.64066(11) 0.39825(10) 0.0387(3) Uani 1 1 d . . .
N10 N 0.21518(13) 0.96454(12) 0.56246(9) 0.0212(3) Uani 1 1 d . . .
C12 C 0.23463(13) 0.80962(12) 0.42269(9) 0.0159(3) Uani 1 1 d . . .
C13 C 0.40460(14) 0.60431(13) 0.35531(10) 0.0177(3) Uani 1 1 d . . .
C14 C 0.54958(14) 0.69503(14) 0.38769(10) 0.0199(3) Uani 1 1 d . . .
C15 C 0.16060(13) 0.84842(13) 0.50455(9) 0.0159(3) Uani 1 1 d . . .
C16 C 0.12963(15) 0.79580(15) 0.32834(10) 0.0212(3) Uani 1 1 d . . .
C17 C 0.21826(15) 1.04418(14) 0.73545(10) 0.0233(3) Uani 1 1 d . . .
C18 C 0.19061(15) 0.56008(14) 0.76576(10) 0.0229(3) Uani 1 1 d . . .
C20 C 0.34850(17) 0.60111(18) 0.24979(11) 0.0273(3) Uani 1 1 d . . .
C21 C 0.16935(16) 0.59244(14) 0.66775(10) 0.0224(3) Uani 1 1 d . . .
C23 C 0.14679(16) 1.03038(15) 0.63186(11) 0.0243(3) Uani 1 1 d . . .
C25 C 0.27545(17) 1.16697(16) 0.79389(12) 0.0321(4) Uani 1 1 d . . .
C26 C 0.3234(2) 0.56732(18) 0.81815(14) 0.0396(4) Uani 1 1 d . . .
C27 C 0.3366(2) 1.17799(19) 0.89000(13) 0.0411(4) Uani 1 1 d . . .
C28 C 0.0782(2) 0.52304(18) 0.80538(12) 0.0379(4) Uani 1 1 d . . .
C30 C 0.3419(2) 1.06688(19) 0.92859(13) 0.0407(4) Uani 1 1 d . . .
C31 C 0.2256(2) 0.93364(17) 0.77568(13) 0.0397(4) Uani 1 1 d . . .
C32 C 0.2869(2) 0.94458(19) 0.87088(14) 0.0455(5) Uani 1 1 d . . .
C36 C 0.2278(4) 0.4993(2) 0.94691(15) 0.0681(8) Uani 1 1 d . . .
C37 C 0.0973(3) 0.4912(2) 0.89517(15) 0.0601(6) Uani 1 1 d . . .
C38 C 0.3407(3) 0.5382(2) 0.90915(17) 0.0635(7) Uani 1 1 d . . .
H41 H 0.160(2) 0.353(2) 0.3818(14) 0.046(6) Uiso 1 1 d . . .
H42 H 0.1448(15) 1.1195(16) 0.6176(11) 0.021(4) Uiso 1 1 d . . .
H44 H 0.1711(18) 0.7695(17) 0.2707(13) 0.036(5) Uiso 1 1 d . . .
H49 H 0.082(2) 0.250(2) 0.4087(15) 0.051(6) Uiso 1 1 d . . .
N11 N 0.37402(13) 0.16373(13) 0.37131(9) 0.0203(3) Uani 1 1 d . . .
C19 C 0.29403(16) 0.04433(14) 0.20028(10) 0.0252(3) Uani 1 1 d . . .
C22 C 0.15575(17) 0.05251(17) 0.17454(11) 0.0314(4) Uani 1 1 d . . .
C24 C 0.33734(19) -0.06616(16) 0.15888(11) 0.0316(4) Uani 1 1 d . . .
C29 C 0.39760(18) 0.15381(16) 0.27179(11) 0.0290(4) Uani 1 1 d . . .
C33 C 0.1071(2) -0.15722(18) 0.06614(12) 0.0444(5) Uani 1 1 d . . .
C34 C 0.2438(2) -0.16606(17) 0.09135(12) 0.0402(4) Uani 1 1 d . . .
C35 C 0.0626(2) -0.04883(19) 0.10826(12) 0.0406(4) Uani 1 1 d . . .
H12 H 0.0515(18) 0.9819(16) 0.6185(11) 0.027(4) Uiso 1 1 d . . .
H13 H 0.043(2) 0.7305(18) 0.3246(13) 0.038(5) Uiso 1 1 d . . .
H15 H 0.1043(18) 0.8803(19) 0.3264(12) 0.037(5) Uiso 1 1 d . . .
H16 H 0.4344(19) -0.0728(17) 0.1781(12) 0.034(5) Uiso 1 1 d . . .
H17 H 0.291(2) 1.0113(18) 0.5563(13) 0.035(5) Uiso 1 1 d . . .
H18 H 0.1364(17) 0.4964(17) 0.5305(13) 0.032(5) Uiso 1 1 d . . .
H19 H 0.295(2) 0.1997(18) 0.3771(13) 0.039(5) Uiso 1 1 d . . .
H20 H 0.3626(18) 0.0814(19) 0.3883(12) 0.033(5) Uiso 1 1 d . . .
H1 H 0.0946(18) 0.6413(17) 0.6582(12) 0.032(5) Uiso 1 1 d . . .
H2 H 0.2527(19) 0.6431(17) 0.6589(12) 0.031(4) Uiso 1 1 d . . .
H3 H 0.3436(19) 0.689(2) 0.2389(13) 0.041(5) Uiso 1 1 d . . .
H4 H 0.4114(18) 0.5668(17) 0.2133(12) 0.034(5) Uiso 1 1 d . . .
H5 H 0.1915(19) 0.4196(17) 0.5997(12) 0.031(5) Uiso 1 1 d . . .
H6 H 0.041(2) 0.4283(19) 0.5857(13) 0.041(5) Uiso 1 1 d . . .
H7 H 0.453(2) 0.2233(19) 0.4153(14) 0.044(5) Uiso 1 1 d . . .
H8 H 0.252(2) 0.5422(18) 0.2270(13) 0.038(5) Uiso 1 1 d . . .
H9 H 0.3909(19) 0.2406(19) 0.2552(13) 0.039(5) Uiso 1 1 d . . .
H10 H 0.491(2) 0.474(2) 0.3966(15) 0.053(6) Uiso 1 1 d . . .
H11 H 0.1229(19) 0.1310(19) 0.2019(13) 0.042(5) Uiso 1 1 d . . .
H14 H 0.044(2) -0.230(2) 0.0178(16) 0.062(6) Uiso 1 1 d . . .
H21 H 0.276(2) -0.242(2) 0.0611(14) 0.050(6) Uiso 1 1 d . . .
H22 H -0.018(2) 0.519(2) 0.7684(15) 0.051(6) Uiso 1 1 d . . .
H23 H 0.403(2) 0.592(2) 0.7882(15) 0.056(6) Uiso 1 1 d . . .
H24 H 0.488(2) 0.1344(19) 0.2730(13) 0.044(5) Uiso 1 1 d . . .
H25 H 0.383(2) 1.0731(19) 0.9919(15) 0.046(5) Uiso 1 1 d . . .
H26 H 0.2743(19) 1.246(2) 0.7675(13) 0.044(5) Uiso 1 1 d . . .
H27 H -0.032(2) -0.040(2) 0.0928(15) 0.057(6) Uiso 1 1 d . . .
H28 H 0.183(2) 0.849(2) 0.7388(15) 0.059(6) Uiso 1 1 d . . .
H29 H 0.377(2) 1.262(2) 0.9310(15) 0.055(6) Uiso 1 1 d . . .
H30 H 0.290(2) 0.867(2) 0.8967(15) 0.058(6) Uiso 1 1 d . . .
H31 H 0.242(3) 0.479(3) 1.010(2) 0.087(8) Uiso 1 1 d . . .
H32 H 0.429(3) 0.548(3) 0.9412(19) 0.081(8) Uiso 1 1 d . . .
H33 H 0.011(3) 0.463(3) 0.9198(18) 0.083(8) Uiso 1 1 d . . .
H34 H 0.420(3) 0.879(2) 0.4151(16) 0.068(7) Uiso 1 1 d . . .
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'
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 116.97(5) . . ?
O3 P1 C13 106.25(6) . . ?
O1 P1 C13 107.36(6) . . ?
O3 P1 C12 107.89(6) . . ?
O1 P1 C12 106.34(6) . . ?
C13 P1 C12 112.16(6) . . ?
C15 N10 C23 124.42(12) . . ?
O2 C12 C16 109.72(11) . . ?
O2 C12 C15 108.18(10) . . ?
C16 C12 C15 106.60(11) . . ?
O2 C12 P1 111.41(9) . . ?
C16 C12 P1 113.51(9) . . ?
C15 C12 P1 107.15(9) . . ?
O5 C13 C20 107.77(11) . . ?
O5 C13 C14 110.20(11) . . ?
C20 C13 C14 109.20(12) . . ?
O5 C13 P1 103.16(9) . . ?
C20 C13 P1 116.02(10) . . ?
C14 C13 P1 110.25(9) . . ?
O9 C14 O8 125.62(13) . . ?
O9 C14 C13 116.84(12) . . ?
O8 C14 C13 117.54(12) . . ?
O6 C15 N10 124.26(12) . . ?
O6 C15 C12 119.48(11) . . ?
N10 C15 C12 116.16(11) . . ?
C25 C17 C31 117.87(15) . . ?
C25 C17 C23 121.29(14) . . ?
C31 C17 C23 120.83(14) . . ?
C28 C18 C26 119.09(16) . . ?
C28 C18 C21 120.33(14) . . ?
C26 C18 C21 120.58(15) . . ?
N7 C21 C18 112.59(12) . . ?
N10 C23 C17 114.22(12) . . ?
C17 C25 C27 120.52(16) . . ?
C38 C26 C18 119.6(2) . . ?
C30 C27 C25 120.62(17) . . ?
C18 C28 C37 120.5(2) . . ?
C32 C30 C27 119.28(17) . . ?
C32 C31 C17 121.60(16) . . ?
C30 C32 C31 120.11(17) . . ?
C37 C36 C38 119.8(2) . . ?
C36 C37 C28 120.4(2) . . ?
C36 C38 C26 120.7(2) . . ?
C22 C19 C24 119.36(15) . . ?
C22 C19 C29 120.96(14) . . ?
C24 C19 C29 119.68(15) . . ?
C35 C22 C19 119.98(16) . . ?
C34 C24 C19 120.22(17) . . ?
N11 C29 C19 112.87(12) . . ?
C34 C33 C35 120.07(17) . . ?
C33 C34 C24 120.09(17) . . ?
C33 C35 C22 120.26(18) . . ?
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 1.5206(10) . ?
P1 O1 1.5269(10) . ?
P1 C13 1.8891(14) . ?
P1 C12 1.9009(14) . ?
O2 C12 1.4354(16) . ?
O5 C13 1.4463(17) . ?
O6 C15 1.2539(16) . ?
N7 C21 1.5069(18) . ?
O8 C14 1.2682(17) . ?
O9 C14 1.2485(18) . ?
N10 C15 1.3384(18) . ?
N10 C23 1.4794(18) . ?
C12 C16 1.5493(19) . ?
C12 C15 1.5611(18) . ?
C13 C20 1.536(2) . ?
C13 C14 1.5543(19) . ?
C17 C25 1.398(2) . ?
C17 C31 1.403(2) . ?
C17 C23 1.526(2) . ?
C18 C28 1.396(2) . ?
C18 C26 1.404(2) . ?
C18 C21 1.514(2) . ?
C25 C27 1.406(2) . ?
C26 C38 1.402(3) . ?
C27 C30 1.393(3) . ?
C28 C37 1.397(3) . ?
C30 C32 1.387(3) . ?
C31 C32 1.394(3) . ?
C36 C37 1.379(4) . ?
C36 C38 1.387(4) . ?
N11 C29 1.507(2) . ?
C19 C22 1.404(2) . ?
C19 C24 1.405(2) . ?
C19 C29 1.524(2) . ?
C22 C35 1.400(2) . ?
C24 C34 1.402(3) . ?
C33 C34 1.390(3) . ?
C33 C35 1.397(3) . ?
