#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/28/2212804.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_2212804
loop_
_publ_author_name
'Guo, Ming-Lin'
'Zang, Hong-Jun'
_publ_section_title
;
 (1-Oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-yl)methanol
;
_journal_coeditor_code           BX2068
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1967
_journal_page_last               o1968
_journal_paper_doi               10.1107/S1600536807012986
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H9 O5 P'
_chemical_formula_moiety         'C5 H9 O5 P'
_chemical_formula_sum            'C5 H9 O5 P'
_chemical_formula_weight         180.09
_chemical_name_systematic
;
(1-Oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-yl)methanol
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   10.792(2)
_cell_length_b                   10.6383(19)
_cell_length_c                   12.518(2)
_cell_measurement_reflns_used    3219
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.69
_cell_volume                     1437.2(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7571
_diffrn_reflns_theta_full        26.51
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0329
_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)+(0.037P)²+0.8026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                1176
_reflns_number_total             1485
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2068.cif
_cod_data_source_block           I
_cod_original_cell_volume        1437.1(4)
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               2212804
_cod_database_fobs_code          2212804
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
P P1 0.61117(5) 0.87872(5) 0.59730(4) 0.03700(17) Uani d . 1
O O1 0.70820(15) 0.97140(14) 0.57851(13) 0.0548(4) Uani d . 1
O O2 0.65822(12) 0.75759(14) 0.65554(13) 0.0501(4) Uani d . 1
O O3 0.50163(14) 0.92827(13) 0.66737(12) 0.0485(4) Uani d . 1
O O4 0.54833(14) 0.82860(14) 0.49283(11) 0.0483(4) Uani d . 1
O O5 0.35637(15) 0.49877(14) 0.60005(14) 0.0487(4) Uani d . 1
C C1 0.56134(17) 0.66290(19) 0.67396(17) 0.0403(5) Uani d . 1
H H1A 0.5548 0.6454 0.7498 0.048 Uiso calc R 1
H H1B 0.5831 0.5854 0.6377 0.048 Uiso calc R 1
C C2 0.44799(19) 0.7384(2) 0.51247(15) 0.0395(5) Uani d . 1
H H2A 0.4648 0.6609 0.4743 0.047 Uiso calc R 1
H H2B 0.3704 0.7725 0.4861 0.047 Uiso calc R 1
C C3 0.40640(18) 0.83362(19) 0.69025(17) 0.0407(5) Uani d . 1
H H3A 0.3261 0.8643 0.6672 0.049 Uiso calc R 1
H H3B 0.4026 0.8183 0.7666 0.049 Uiso calc R 1
C C4 0.43683(16) 0.71125(16) 0.63194(14) 0.0294(4) Uani d . 1
C C5 0.33465(18) 0.61453(18) 0.65391(16) 0.0383(5) Uani d . 1
H H5A 0.3299 0.5991 0.7302 0.046 Uiso calc R 1
H H5B 0.2556 0.6486 0.6310 0.046 Uiso calc R 1
H H5 0.316(3) 0.509(3) 0.540(2) 0.075(9) Uiso d . 1
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
P1 0.0377(3) 0.0338(3) 0.0395(3) -0.0051(2) 0.0028(2) -0.0031(2)
O1 0.0545(9) 0.0475(9) 0.0625(10) -0.0192(8) 0.0080(8) -0.0064(7)
O2 0.0302(7) 0.0458(8) 0.0742(11) -0.0020(6) -0.0073(7) 0.0114(8)
O3 0.0519(9) 0.0341(7) 0.0594(10) -0.0020(7) 0.0132(7) -0.0134(7)
O4 0.0590(9) 0.0534(9) 0.0325(7) -0.0228(7) 0.0049(7) 0.0014(6)
O5 0.0517(9) 0.0350(8) 0.0594(10) -0.0041(7) -0.0012(8) 0.0005(7)
C1 0.0310(10) 0.0358(10) 0.0542(12) 0.0022(8) -0.0016(9) 0.0081(9)
C2 0.0442(11) 0.0417(11) 0.0327(10) -0.0114(9) -0.0015(8) 0.0023(8)
C3 0.0382(10) 0.0398(10) 0.0440(11) 0.0035(9) 0.0078(9) -0.0030(9)
C4 0.0287(9) 0.0302(9) 0.0292(9) 0.0040(7) 0.0005(7) 0.0016(7)
C5 0.0343(10) 0.0415(11) 0.0389(11) -0.0021(9) 0.0034(8) 0.0050(9)
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'
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
O1 P1 O3 113.93(9)
O1 P1 O2 113.52(9)
O3 P1 O2 105.16(9)
O1 P1 O4 113.98(9)
O3 P1 O4 104.82(9)
O2 P1 O4 104.42(9)
C1 O2 P1 113.98(11)
C3 O3 P1 114.07(11)
C2 O4 P1 113.70(11)
C5 O5 H5 102.7(19)
O2 C1 C4 109.87(15)
O2 C1 H1A 109.7
C4 C1 H1A 109.7
O2 C1 H1B 109.7
C4 C1 H1B 109.7
H1A C1 H1B 108.2
O4 C2 C4 110.23(14)
O4 C2 H2A 109.6
C4 C2 H2A 109.6
O4 C2 H2B 109.6
C4 C2 H2B 109.6
H2A C2 H2B 108.1
O3 C3 C4 109.93(15)
O3 C3 H3A 109.7
C4 C3 H3A 109.7
O3 C3 H3B 109.7
C4 C3 H3B 109.7
H3A C3 H3B 108.2
C2 C4 C3 108.86(16)
C2 C4 C1 109.29(16)
C3 C4 C1 108.09(16)
C2 C4 C5 111.05(15)
C3 C4 C5 109.36(15)
C1 C4 C5 110.12(15)
O5 C5 C4 112.16(15)
O5 C5 H5A 109.2
C4 C5 H5A 109.2
O5 C5 H5B 109.2
C4 C5 H5B 109.2
H5A C5 H5B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4573(15)
P1 O3 1.5635(15)
P1 O2 1.5652(15)
P1 O4 1.5667(15)
O2 C1 1.470(2)
O3 C3 1.467(2)
O4 C2 1.468(2)
O5 C5 1.423(2)
O5 H5 0.87(3)
C1 C4 1.532(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C4 1.528(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.528(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.533(3)
C5 H5A 0.9700
C5 H5B 0.9700
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
O5 H5 O1 4_466 0.87(3) 1.90(3) 2.767(2) 172(3)
C3 H3A O5 8_665 0.97 2.57 3.522(3) 165.3
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
O1 P1 O2 C1 -179.42(13)
O3 P1 O2 C1 55.39(15)
O4 P1 O2 C1 -54.69(15)
O1 P1 O3 C3 -177.53(14)
O2 P1 O3 C3 -52.59(15)
O4 P1 O3 C3 57.20(15)
O1 P1 O4 C2 -178.11(14)
O3 P1 O4 C2 -52.87(15)
O2 P1 O4 C2 57.45(15)
P1 O2 C1 C4 -1.2(2)
P1 O4 C2 C4 -3.4(2)
P1 O3 C3 C4 -3.7(2)
O4 C2 C4 C3 61.0(2)
O4 C2 C4 C1 -56.8(2)
O4 C2 C4 C5 -178.52(15)
O3 C3 C4 C2 -56.9(2)
O3 C3 C4 C1 61.8(2)
O3 C3 C4 C5 -178.36(15)
O2 C1 C4 C2 59.4(2)
O2 C1 C4 C3 -58.9(2)
O2 C1 C4 C5 -178.32(15)
C2 C4 C5 O5 58.7(2)
C3 C4 C5 O5 178.90(16)
C1 C4 C5 O5 -62.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 173053
