#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:26:43 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250102 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038108.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_4038108
loop_
_publ_author_name
'Hernández-Guerra, Daniel'
'Kennedy, Alan R.'
'León, Elisa I'
'Martín, Ángeles'
'Pérez-Martín, Inés'
'Rodríguez, María S'
'Suárez, Ernesto'
_publ_section_title
;
 Synthetic Approaches to Phosphasugars (2-oxo-1,2-oxaphosphacyclanes)
 Using the Anomeric Alkoxyl Radical β-Fragmentation Reaction as the Key
 Step.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4861
_journal_page_last               4880
_journal_paper_doi               10.1021/acs.joc.0c00059
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H17 O6 P'
_chemical_formula_weight         312.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1955(2)
_cell_length_b                   13.6351(5)
_cell_length_c                   17.2061(6)
_cell_measurement_reflns_used    2850
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.8044
_cell_measurement_theta_min      3.2816
_cell_volume                     1453.51(9)
_computing_cell_refinement       CrysalisPro
_computing_data_collection       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7478
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.871
_diffrn_reflns_theta_min         3.495
_diffrn_source                   tube
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       'elongated tablet'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0337P)²+0.1525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.836
_reflns_number_gt                3015
_reflns_number_total             3686
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00059_si_001.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 4038108.cif.'
_cod_database_code               4038108
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.82771(12) 0.90859(5) 0.66565(4) 0.01757(17) Uani 1 1 d . . . . .
O1 O 0.6113(3) 0.88945(16) 0.69775(12) 0.0249(5) Uani 1 1 d . . . . .
O2 O 1.0113(3) 0.83337(14) 0.69133(12) 0.0198(5) Uani 1 1 d . . . . .
O3 O 1.0223(3) 0.80028(14) 0.82375(12) 0.0246(5) Uani 1 1 d . . . . .
O4 O 1.0384(3) 0.96407(14) 0.84496(12) 0.0213(5) Uani 1 1 d . . . . .
O5 O 1.2352(3) 1.11151(15) 0.75329(13) 0.0253(5) Uani 1 1 d . . . . .
O6 O 1.4242(4) 1.14746(19) 0.64516(17) 0.0458(7) Uani 1 1 d . . . . .
C1 C 0.9398(5) 1.0260(2) 0.69254(18) 0.0209(7) Uani 1 1 d . . . . .
H1A H 0.9357 1.0703 0.6469 0.025 Uiso 1 1 calc R U . . .
H1B H 0.8495 1.0556 0.7338 0.025 Uiso 1 1 calc R U . . .
C2 C 1.1718(5) 1.0178(2) 0.72150(17) 0.0199(6) Uani 1 1 d . . . . .
H2 H 1.2694 0.9997 0.6775 0.024 Uiso 1 1 calc R U . . .
C3 C 1.1917(5) 0.9438(2) 0.78578(17) 0.0198(6) Uani 1 1 d . . . . .
H3 H 1.3408 0.9460 0.8080 0.024 Uiso 1 1 calc R U . . .
C4 C 1.1372(5) 0.8388(2) 0.76124(17) 0.0199(6) Uani 1 1 d . . . . .
H4 H 1.2739 0.8008 0.7542 0.024 Uiso 1 1 calc R U . . .
C5 C 0.9918(5) 0.8739(2) 0.88263(17) 0.0225(7) Uani 1 1 d . . . . .
C6 C 0.7596(5) 0.8750(3) 0.9073(2) 0.0307(8) Uani 1 1 d . . . . .
H6A H 0.7385 0.9255 0.9472 0.046 Uiso 1 1 calc R U . . .
H6B H 0.7206 0.8108 0.9287 0.046 Uiso 1 1 calc R U . . .
H6C H 0.6680 0.8895 0.8624 0.046 Uiso 1 1 calc R U . . .
C7 C 1.1461(6) 0.8540(3) 0.9486(2) 0.0411(9) Uani 1 1 d . . . . .
H7A H 1.2948 0.8577 0.9295 0.062 Uiso 1 1 calc R U . . .
H7B H 1.1187 0.7885 0.9698 0.062 Uiso 1 1 calc R U . . .
H7C H 1.1249 0.9031 0.9895 0.062 Uiso 1 1 calc R U . . .
C8 C 1.3559(5) 1.1688(2) 0.7075(2) 0.0278(8) Uani 1 1 d . . . . .
H8 H 1.3902 1.2323 0.7265 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8405(5) 0.8936(2) 0.56227(16) 0.0182(6) Uani 1 1 d . . . . .
C10 C 0.6612(5) 0.8599(2) 0.52271(18) 0.0234(7) Uani 1 1 d . . . . .
H10 H 0.5309 0.8472 0.5500 0.028 Uiso 1 1 calc R U . . .
C11 C 0.6715(6) 0.8444(2) 0.44305(19) 0.0301(7) Uani 1 1 d . . . . .
H11 H 0.5483 0.8214 0.4157 0.036 Uiso 1 1 calc R U . . .
C12 C 0.8613(6) 0.8628(2) 0.40377(18) 0.0296(8) Uani 1 1 d . . . . .
H12 H 0.8686 0.8514 0.3494 0.035 Uiso 1 1 calc R U . . .
C13 C 1.0403(5) 0.8973(3) 0.44232(18) 0.0283(7) Uani 1 1 d . . . . .
H13 H 1.1698 0.9105 0.4147 0.034 Uiso 1 1 calc R U . . .
C14 C 1.0304(5) 0.9127(2) 0.52170(18) 0.0237(7) Uani 1 1 d . . . . .
H14 H 1.1536 0.9364 0.5486 0.028 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
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'
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
O1 P1 O2 115.56(12) . . ?
O1 P1 C9 113.09(14) . . ?
O2 P1 C9 99.78(12) . . ?
O1 P1 C1 114.27(14) . . ?
O2 P1 C1 103.01(13) . . ?
C9 P1 C1 109.79(14) . . ?
C4 O2 P1 125.92(18) . . ?
C4 O3 C5 110.4(2) . . ?
C3 O4 C5 107.1(2) . . ?
C8 O5 C2 116.4(2) . . ?
C2 C1 P1 112.4(2) . . ?
C2 C1 H1A 109.1 . . ?
P1 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
P1 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
O5 C2 C3 107.0(2) . . ?
O5 C2 C1 108.4(2) . . ?
C3 C2 C1 111.5(3) . . ?
O5 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
O4 C3 C2 110.0(2) . . ?
O4 C3 C4 103.5(2) . . ?
C2 C3 C4 114.0(2) . . ?
O4 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
O3 C4 O2 110.5(2) . . ?
O3 C4 C3 104.6(2) . . ?
O2 C4 C3 113.5(2) . . ?
O3 C4 H4 109.3 . . ?
O2 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
O4 C5 O3 104.8(2) . . ?
O4 C5 C6 108.4(3) . . ?
O3 C5 C6 109.4(3) . . ?
O4 C5 C7 111.7(3) . . ?
O3 C5 C7 108.8(3) . . ?
C6 C5 C7 113.3(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O6 C8 O5 126.0(3) . . ?
O6 C8 H8 117.0 . . ?
O5 C8 H8 117.0 . . ?
C10 C9 C14 119.6(3) . . ?
C10 C9 P1 119.4(2) . . ?
C14 C9 P1 120.9(2) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
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 O1 1.473(2) . ?
P1 O2 1.594(2) . ?
P1 C9 1.792(3) . ?
P1 C1 1.805(3) . ?
O2 C4 1.436(3) . ?
O3 C4 1.393(3) . ?
O3 C5 1.439(3) . ?
O4 C3 1.420(3) . ?
O4 C5 1.420(3) . ?
O5 C8 1.338(4) . ?
O5 C2 1.444(3) . ?
O6 C8 1.189(4) . ?
C1 C2 1.525(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.503(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.530(4) . ?
C3 H3 1.0000 . ?
C4 H4 1.0000 . ?
C5 C6 1.500(5) . ?
C5 C7 1.509(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C9 C10 1.382(4) . ?
C9 C14 1.392(4) . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O2 C4 -85.0(2) . . . . ?
C9 P1 O2 C4 153.4(2) . . . . ?
C1 P1 O2 C4 40.3(2) . . . . ?
O1 P1 C1 C2 132.1(2) . . . . ?
O2 P1 C1 C2 6.0(2) . . . . ?
C9 P1 C1 C2 -99.6(2) . . . . ?
C8 O5 C2 C3 139.3(3) . . . . ?
C8 O5 C2 C1 -100.2(3) . . . . ?
P1 C1 C2 O5 -170.77(19) . . . . ?
P1 C1 C2 C3 -53.2(3) . . . . ?
C5 O4 C3 C2 153.0(2) . . . . ?
C5 O4 C3 C4 30.9(3) . . . . ?
O5 C2 C3 O4 66.2(3) . . . . ?
C1 C2 C3 O4 -52.2(3) . . . . ?
O5 C2 C3 C4 -178.1(2) . . . . ?
C1 C2 C3 C4 63.5(3) . . . . ?
C5 O3 C4 O2 -119.5(2) . . . . ?
C5 O3 C4 C3 3.0(3) . . . . ?
P1 O2 C4 O3 81.4(3) . . . . ?
P1 O2 C4 C3 -35.8(3) . . . . ?
O4 C3 C4 O3 -20.6(3) . . . . ?
C2 C3 C4 O3 -140.0(3) . . . . ?
O4 C3 C4 O2 100.0(3) . . . . ?
C2 C3 C4 O2 -19.5(4) . . . . ?
C3 O4 C5 O3 -29.4(3) . . . . ?
C3 O4 C5 C6 -146.2(3) . . . . ?
C3 O4 C5 C7 88.2(3) . . . . ?
C4 O3 C5 O4 15.7(3) . . . . ?
C4 O3 C5 C6 131.8(3) . . . . ?
C4 O3 C5 C7 -103.9(3) . . . . ?
C2 O5 C8 O6 -4.2(5) . . . . ?
O1 P1 C9 C10 -4.6(3) . . . . ?
O2 P1 C9 C10 118.7(2) . . . . ?
C1 P1 C9 C10 -133.5(2) . . . . ?
O1 P1 C9 C14 177.3(2) . . . . ?
O2 P1 C9 C14 -59.4(3) . . . . ?
C1 P1 C9 C14 48.4(3) . . . . ?
C14 C9 C10 C11 0.5(4) . . . . ?
P1 C9 C10 C11 -177.6(2) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 C9 -0.1(5) . . . . ?
C10 C9 C14 C13 -0.5(5) . . . . ?
P1 C9 C14 C13 177.6(3) . . . . ?
