#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/51/2205178.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_2205178
loop_
_publ_author_name
'Yu, Lin'
'Liu, Zhao'
'Fang, Hua'
'Zhao, Yu-Fen'
_publ_section_title
(3S,8S)-3,8-Dimethyl-1,6-dioxa-4,9-diaza-5λ⁵-phosphaspiro[4.4]nonane-2,7-dione
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o261
_journal_page_last               o262
_journal_paper_doi               10.1107/S160053680403421X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C6 H11 N2 O4 P'
_chemical_formula_sum            'C6 H11 N2 O4 P'
_chemical_formula_weight         206.14
_chemical_name_systematic
;
3,8-Dimethyl-1,6-dioxa-4,9-diaza-5λ⁵-phosphaspiro[4.4]nonane-2,7-dione
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1138(12)
_cell_length_b                   7.6933(15)
_cell_length_c                   19.824(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      8
_cell_volume                     932.4(3)
_computing_cell_refinement       'CAD-4 software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1988)'
_computing_data_reduction        'XCAD4 (Harms, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'ω-2θ scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            570
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.551
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       0.010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1249P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1979
_reflns_number_gt                430
_reflns_number_total             570
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6313.cif
_cod_data_source_block           I
_cod_database_code               2205178
_cod_database_fobs_code          2205178
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_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_type_symbol
P 1.0000 0.7364(3) 0.2500 0.0430(7) Uani d S 1 P
O1 0.7388(7) 0.7392(8) 0.2140(2) 0.0529(12) Uani d . 1 O
O2 0.5527(8) 0.8415(8) 0.1265(2) 0.0664(16) Uani d . 1 O
N1 1.0942(9) 0.8294(8) 0.1826(3) 0.0511(15) Uani d . 1 N
H1D 1.2321 0.8486 0.1783 0.061 Uiso calc R 1 H
C3 0.9435(10) 0.8801(9) 0.1293(3) 0.0491(17) Uani d . 1 C
H3 0.9424 1.0070 0.1249 0.059 Uiso calc R 1 H
C1 0.9974(16) 0.7987(13) 0.0619(3) 0.079(2) Uani d . 1 C
H1A 1.1376 0.8393 0.0469 0.119 Uiso calc R 1 H
H1B 0.8878 0.8305 0.0295 0.119 Uiso calc R 1 H
H1C 1.0009 0.6745 0.0665 0.119 Uiso calc R 1 H
C2 0.7234(12) 0.8184(9) 0.1556(3) 0.0475(16) Uani d . 1 C
H 1.0000 0.542(12) 0.2500 0.057 Uiso d S 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
P 0.0309(11) 0.0424(12) 0.0557(13) 0.000 0.0066(10) 0.000
O1 0.032(2) 0.064(3) 0.062(2) -0.010(2) 0.006(2) 0.001(2)
O2 0.033(3) 0.095(4) 0.070(3) -0.012(3) -0.002(2) 0.000(3)
N1 0.031(3) 0.070(4) 0.052(3) -0.015(3) 0.005(2) -0.007(3)
C3 0.037(4) 0.053(4) 0.057(4) -0.009(3) 0.005(3) 0.007(3)
C1 0.061(5) 0.119(7) 0.058(4) -0.009(7) 0.003(4) -0.011(4)
C2 0.040(3) 0.047(3) 0.056(3) -0.002(3) 0.006(3) -0.005(3)
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
N1 P N1 3_755 . 127.6(4) yes
N1 P O1 . 3_755 90.4(2) yes
N1 P O1 . . 89.0(3) yes
O1 P O1 3_755 . 178.6(4) yes
N1 P H 3_755 . 116.2(2) no
N1 P H . . 116.2(2) yes
O1 P H 3_755 . 90.7(2) no
O1 P H . . 90.7(2) no
C2 O1 P . . 115.6(4) yes
C3 N1 P . . 119.5(4) yes
C3 N1 H1D . . 120.3 no
P N1 H1D . . 120.3 no
N1 C3 C1 . . 113.1(6) yes
N1 C3 C2 . . 103.1(5) yes
C1 C3 C2 . . 111.6(6) yes
N1 C3 H3 . . 109.6 no
C1 C3 H3 . . 109.6 no
C2 C3 H3 . . 109.6 no
C3 C1 H1A . . 109.5 no
C3 C1 H1B . . 109.5 no
H1A C1 H1B . . 109.5 no
C3 C1 H1C . . 109.5 no
H1A C1 H1C . . 109.5 no
H1B C1 H1C . . 109.5 no
O2 C2 O1 . . 123.6(6) yes
O2 C2 C3 . . 123.8(6) yes
O1 C2 C3 . . 112.6(6) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P N1 1.622(5) yes
P O1 1.750(5) yes
P H 1.49(9) yes
O1 C2 1.310(8) yes
O2 C2 1.206(9) yes
N1 C3 1.455(9) yes
N1 H1D 0.8600 no
C3 C1 1.511(9) yes
C3 C2 1.520(9) yes
C3 H3 0.9800 no
C1 H1A 0.9600 no
C1 H1B 0.9600 no
C1 H1C 0.9600 no
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
N1 H1D O2 1_655 0.86 2.21 3.017(7) 155
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
_geom_torsion_publ_flag
N1 P O1 C2 3_755 123.2(5) no
N1 P O1 C2 . -4.4(5) no
O1 P O1 C2 3_755 59.4(5) no
N1 P N1 C3 3_755 -86.2(5) no
O1 P N1 C3 3_755 -175.2(5) no
O1 P N1 C3 . 3.5(6) no
P N1 C3 C1 . -122.5(6) no
P N1 C3 C2 . -1.8(7) no
P O1 C2 O2 . -174.9(6) no
P O1 C2 C3 . 4.2(7) no
N1 C3 C2 O2 . 177.5(7) no
C1 C3 C2 O2 . -60.8(9) no
N1 C3 C2 O1 . -1.6(7) no
C1 C3 C2 O1 . 120.1(7) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173630
