#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/46/2224649.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_2224649
loop_
_publ_author_name
'Mandal, Tanmay'
'Samanta, Sampak'
'Broker, Grant A.'
'Zhao, Cong-Gui'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Bis(propan-2-yl)
 [(2S,3S)-2-hydroxy-3-nitrobutan-2-yl]phosphonate
;
_journal_coeditor_code           HB5269
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o98
_journal_paper_doi               10.1107/S1600536809052428
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H22 N O6 P'
_chemical_formula_moiety         'C10 H22 N O6 P'
_chemical_formula_sum            'C10 H22 N O6 P'
_chemical_formula_weight         283.26
_chemical_name_systematic
;Bis(propan-2-yl)
 [(2S,3S)-2-hydroxy-3-nitrobutan-2-yl]phosphonate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8620(16)
_cell_length_b                   11.369(2)
_cell_length_c                   16.920(3)
_cell_measurement_reflns_used    2308
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      4.0
_cell_volume                     1512.4(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku AFC12Κ/SATURN724'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.089
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13441
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         4.0
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details 'Flack (1983), 1272 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.040
_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)+(0.0497P)²+0.2822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.105
_refine_ls_wR_factor_ref         0.105
_reflns_number_gt                3020
_reflns_number_total             3072
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5269.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_database_code               2224649
_cod_database_fobs_code          2224649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.63065(6) 0.29509(4) 0.74005(3) 0.03236(14) Uani d . 1 . .
O O1 0.51586(18) 0.19464(11) 0.75316(9) 0.0416(3) Uani d . 1 . .
O O2 0.80539(18) 0.26553(13) 0.70112(9) 0.0415(3) Uani d . 1 . .
O O3 0.67933(17) 0.36408(13) 0.81677(8) 0.0383(3) Uani d . 1 . .
O O4 0.41385(17) 0.46364(12) 0.71762(9) 0.0400(3) Uani d D 1 . .
H H4O 0.4448 0.5337 0.7241 0.060 Uiso d D 1 . .
O O5 0.3878(4) 0.49342(19) 0.51776(13) 0.0848(7) Uani d . 1 . .
O O6 0.1751(3) 0.4227(2) 0.58457(14) 0.0861(7) Uani d . 1 . .
N N1 0.3262(3) 0.4256(2) 0.56573(14) 0.0608(6) Uani d . 1 . .
C C1 0.9313(3) 0.18894(18) 0.74033(13) 0.0438(5) Uani d . 1 . .
H H1 0.8736 0.1412 0.7821 0.053 Uiso calc R 1 . .
C C2 0.9985(4) 0.1089(3) 0.67718(17) 0.0706(8) Uani d . 1 . .
H H2A 0.9051 0.0617 0.6556 0.106 Uiso calc R 1 . .
H H2B 1.0849 0.0567 0.6998 0.106 Uiso calc R 1 . .
H H2C 1.0495 0.1560 0.6348 0.106 Uiso calc R 1 . .
C C3 1.0653(3) 0.2668(2) 0.7782(2) 0.0656(8) Uani d . 1 . .
H H3A 1.0121 0.3162 0.8187 0.098 Uiso calc R 1 . .
H H3B 1.1173 0.3168 0.7377 0.098 Uiso calc R 1 . .
H H3C 1.1530 0.2175 0.8026 0.098 Uiso calc R 1 . .
C C4 0.5800(3) 0.3614(2) 0.89018(13) 0.0551(6) Uani d . 1 . .
H H4 0.4659 0.3254 0.8803 0.066 Uiso calc R 1 . .
C C5 0.5601(6) 0.4848(3) 0.91703(18) 0.0879(11) Uani d . 1 . .
H H5A 0.4970 0.5295 0.8771 0.132 Uiso calc R 1 . .
H H5B 0.6726 0.5202 0.9246 0.132 Uiso calc R 1 . .
H H5C 0.4976 0.4862 0.9671 0.132 Uiso calc R 1 . .
C C6 0.6764(7) 0.2898(3) 0.94900(18) 0.1056(15) Uani d . 1 . .
H H6A 0.6874 0.2089 0.9296 0.158 Uiso calc R 1 . .
H H6B 0.6152 0.2896 0.9995 0.158 Uiso calc R 1 . .
H H6C 0.7897 0.3238 0.9565 0.158 Uiso calc R 1 . .
C C7 0.5409(2) 0.40550(16) 0.67209(11) 0.0336(4) Uani d . 1 . .
C C8 0.4436(3) 0.33911(18) 0.60636(12) 0.0419(5) Uani d . 1 . .
H H8 0.3722 0.2770 0.6318 0.050 Uiso calc R 1 . .
C C9 0.5556(4) 0.2804(2) 0.54440(13) 0.0558(6) Uani d . 1 . .
H H9A 0.4838 0.2406 0.5053 0.084 Uiso calc R 1 . .
H H9B 0.6299 0.2227 0.5700 0.084 Uiso calc R 1 . .
H H9C 0.6251 0.3401 0.5179 0.084 Uiso calc R 1 . .
C C10 0.6767(3) 0.49079(18) 0.64308(14) 0.0430(5) Uani d . 1 . .
H H10A 0.7312 0.5287 0.6885 0.065 Uiso calc R 1 . .
H H10B 0.6239 0.5509 0.6095 0.065 Uiso calc R 1 . .
H H10C 0.7623 0.4477 0.6125 0.065 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 O2 . . 115.86(9) ?
O1 P1 O3 . . 114.44(9) ?
O2 P1 O3 . . 104.06(8) ?
O1 P1 C7 . . 112.80(9) ?
O2 P1 C7 . . 102.75(8) ?
O3 P1 C7 . . 105.67(8) ?
C1 O2 P1 . . 121.86(13) ?
C4 O3 P1 . . 124.17(14) ?
C7 O4 H4O . . 108.0 ?
O5 N1 O6 . . 124.9(3) ?
O5 N1 C8 . . 118.1(2) ?
O6 N1 C8 . . 117.0(2) ?
O2 C1 C2 . . 105.91(18) ?
O2 C1 C3 . . 108.14(17) ?
C2 C1 C3 . . 114.2(2) ?
O2 C1 H1 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
C3 C1 H1 . . 109.5 ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C1 C3 H3A . . 109.5 ?
C1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O3 C4 C5 . . 107.2(2) ?
O3 C4 C6 . . 107.8(2) ?
C5 C4 C6 . . 111.4(3) ?
O3 C4 H4 . . 110.1 ?
C5 C4 H4 . . 110.1 ?
C6 C4 H4 . . 110.1 ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O4 C7 C10 . . 111.74(15) ?
O4 C7 C8 . . 105.60(16) ?
C10 C7 C8 . . 115.18(18) ?
O4 C7 P1 . . 104.31(12) ?
C10 C7 P1 . . 111.47(14) ?
C8 C7 P1 . . 107.80(13) ?
N1 C8 C9 . . 108.94(19) ?
N1 C8 C7 . . 108.11(16) ?
C9 C8 C7 . . 115.0(2) ?
N1 C8 H8 . . 108.2 ?
C9 C8 H8 . . 108.2 ?
C7 C8 H8 . . 108.2 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . 1.4723(14) ?
P1 O2 . 1.5602(14) ?
P1 O3 . 1.5643(15) ?
P1 C7 . 1.8428(19) ?
O2 C1 . 1.476(2) ?
O3 C4 . 1.467(2) ?
O4 C7 . 1.424(2) ?
O4 H4O . 0.8400 ?
O5 N1 . 1.219(3) ?
O6 N1 . 1.230(4) ?
N1 C8 . 1.514(3) ?
C1 C2 . 1.500(3) ?
C1 C3 . 1.517(3) ?
C1 H1 . 1.0000 ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 C5 . 1.483(4) ?
C4 C6 . 1.492(4) ?
C4 H4 . 1.0000 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 C10 . 1.524(3) ?
C7 C8 . 1.546(3) ?
C8 C9 . 1.523(3) ?
C8 H8 . 1.0000 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4o O1 4_656 0.84 1.90 2.7289(19) 172
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 P1 O2 C1 . . . . -63.20(17) ?
O3 P1 O2 C1 . . . . 63.34(17) ?
C7 P1 O2 C1 . . . . 173.35(15) ?
O1 P1 O3 C4 . . . . -21.1(2) ?
O2 P1 O3 C4 . . . . -148.58(17) ?
C7 P1 O3 C4 . . . . 103.58(19) ?
P1 O2 C1 C2 . . . . 136.98(19) ?
P1 O2 C1 C3 . . . . -100.2(2) ?
P1 O3 C4 C5 . . . . -132.8(2) ?
P1 O3 C4 C6 . . . . 107.1(3) ?
O1 P1 C7 O4 . . . . 73.94(14) ?
O2 P1 C7 O4 . . . . -160.59(12) ?
O3 P1 C7 O4 . . . . -51.80(13) ?
O1 P1 C7 C10 . . . . -165.33(14) ?
O2 P1 C7 C10 . . . . -39.85(16) ?
O3 P1 C7 C10 . . . . 68.93(15) ?
O1 P1 C7 C8 . . . . -37.99(17) ?
O2 P1 C7 C8 . . . . 87.48(15) ?
O3 P1 C7 C8 . . . . -163.73(13) ?
O5 N1 C8 C9 . . . . -47.5(3) ?
O6 N1 C8 C9 . . . . 133.2(2) ?
O5 N1 C8 C7 . . . . 78.1(3) ?
O6 N1 C8 C7 . . . . -101.1(3) ?
O4 C7 C8 N1 . . . . 51.7(2) ?
C10 C7 C8 N1 . . . . -72.1(2) ?
P1 C7 C8 N1 . . . . 162.77(16) ?
O4 C7 C8 C9 . . . . 173.70(17) ?
C10 C7 C8 C9 . . . . 49.9(2) ?
P1 C7 C8 C9 . . . . -75.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744081
