#------------------------------------------------------------------------------
#$Date: 2021-11-05 02:02:46 +0200 (Fri, 05 Nov 2021) $
#$Revision: 270313 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/87/7708707.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_7708707
loop_
_publ_author_name
'Guesne, Sebastien'
'Connole, Laura'
'Kim, Stephanie'
'Motevalli, Majid'
'Robson, Lesley'
'Michael-Titus, Adina T'
'Sullivan, Alice'
_publ_section_title
;
 Umbelliferyloxymethyl Phosphonate Compounds- weakly binding zinc
 ionophores with neuroprotective properties
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT02298A
_journal_year                    2021
_chemical_formula_sum            'C15 H19 O6 P'
_chemical_formula_weight         326.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-10-29 deposited with the CCDC.	2021-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.12(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6014(10)
_cell_length_b                   8.812(2)
_cell_length_c                   11.132(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      13.62
_cell_measurement_theta_min      9.96
_cell_volume                     1572.1(5)
_computing_cell_refinement       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_unetI/netI     0.1220
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3800
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         1.987
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   3
        Theta correction was applied.
        Averaged transmission function was used.
        No Fourier smoothing was applied.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       Block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1878
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0769P)²+4.1680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.2212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1836
_reflns_number_total             3585
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02298a2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1572.2(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7708707
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C -0.2286(3) 0.5681(6) 0.3614(4) 0.0319(11) Uani 1 1 d . . . . .
C2 C -0.1864(3) 0.7137(6) 0.3748(4) 0.0300(11) Uani 1 1 d . . . . .
H2 H -0.2160 0.8012 0.3892 0.036 Uiso 1 1 calc R U . . .
C3 C -0.1075(3) 0.7304(6) 0.3677(4) 0.0257(10) Uani 1 1 d . . . . .
C4 C -0.0620(3) 0.5968(5) 0.3482(4) 0.0234(10) Uani 1 1 d . . . . .
C5 C -0.1014(2) 0.4553(5) 0.3371(4) 0.0207(10) Uani 1 1 d . . . . .
C6 C -0.0660(3) 0.8817(6) 0.3799(5) 0.0387(13) Uani 1 1 d . . . . .
H6A H -0.1043 0.9592 0.3959 0.058 Uiso 1 1 calc R U . . .
H6B H -0.0510 0.9061 0.3027 0.058 Uiso 1 1 calc R U . . .
H6C H -0.0155 0.8795 0.4492 0.058 Uiso 1 1 calc R U . . .
C7 C 0.0203(3) 0.5995(6) 0.3369(4) 0.0255(10) Uani 1 1 d . . . . .
H7 H 0.0488 0.6936 0.3414 0.031 Uiso 1 1 calc R U . . .
C8 C 0.0608(3) 0.4659(5) 0.3190(4) 0.0253(11) Uani 1 1 d . . . . .
H8 H 0.1164 0.4693 0.3113 0.030 Uiso 1 1 calc R U . . .
C9 C 0.0195(3) 0.3284(6) 0.3127(4) 0.0285(11) Uani 1 1 d . . . . .
C10 C -0.0635(2) 0.3224(6) 0.3188(4) 0.0230(10) Uani 1 1 d . . . . .
H10 H -0.0927 0.2287 0.3105 0.028 Uiso 1 1 calc R U . . .
C11 C 0.1350(3) 0.1941(6) 0.2776(5) 0.0311(12) Uani 1 1 d . . . . .
H11A H 0.1733 0.2525 0.3447 0.037 Uiso 1 1 calc R U . . .
H11B H 0.1327 0.2449 0.1975 0.037 Uiso 1 1 calc R U . . .
C12A C 0.0951(17) -0.122(4) 0.0620(18) 0.053(5) Uani 0.48(5) 1 d . U P A 1
H12A H 0.1488 -0.1016 0.0419 0.064 Uiso 0.48(5) 1 calc R U P A 1
H12B H 0.0519 -0.0554 0.0096 0.064 Uiso 0.48(5) 1 calc R U P A 1
C13A C 0.072(3) -0.281(3) 0.039(2) 0.065(7) Uani 0.50(6) 1 d . U P A 1
H13A H 0.0690 -0.3059 -0.0475 0.098 Uiso 0.50(6) 1 calc R U P A 1
H13B H 0.0173 -0.2978 0.0551 0.098 Uiso 0.50(6) 1 calc R U P A 1
H13C H 0.1137 -0.3448 0.0946 0.098 Uiso 0.50(6) 1 calc R U P A 1
C12B C 0.1177(13) -0.189(4) 0.092(2) 0.055(6) Uani 0.52(5) 1 d . U P A 2
H12C H 0.1559 -0.2726 0.1283 0.066 Uiso 0.52(5) 1 calc R U P A 2
H12D H 0.1441 -0.1282 0.0375 0.066 Uiso 0.52(5) 1 calc R U P A 2
C13B C 0.0361(18) -0.251(4) 0.017(2) 0.072(6) Uani 0.50(6) 1 d . U P A 2
H13D H 0.0457 -0.3191 -0.0471 0.108 Uiso 0.50(6) 1 calc R U P A 2
H13E H -0.0004 -0.1676 -0.0217 0.108 Uiso 0.50(6) 1 calc R U P A 2
H13F H 0.0094 -0.3078 0.0724 0.108 Uiso 0.50(6) 1 calc R U P A 2
C14 C 0.2228(3) -0.1897(7) 0.4584(5) 0.0403(13) Uani 1 1 d . . . . .
H14A H 0.2258 -0.2572 0.3886 0.048 Uiso 1 1 calc R U . . .
H14B H 0.1925 -0.2440 0.5111 0.048 Uiso 1 1 calc R U . . .
C15 C 0.3082(4) -0.1529(8) 0.5329(5) 0.0563(17) Uani 1 1 d . . . . .
H15A H 0.3386 -0.1015 0.4801 0.084 Uiso 1 1 calc R U . . .
H15B H 0.3374 -0.2467 0.5659 0.084 Uiso 1 1 calc R U . . .
H15C H 0.3051 -0.0862 0.6020 0.084 Uiso 1 1 calc R U . . .
O1 O -0.18367(17) 0.4436(4) 0.3426(3) 0.0268(7) Uani 1 1 d . . . . .
O2 O -0.3001(2) 0.5463(5) 0.3633(3) 0.0435(10) Uani 1 1 d . . . . .
O3 O 0.05402(17) 0.1922(4) 0.2981(3) 0.0280(8) Uani 1 1 d . . . . .
O4 O 0.25341(19) 0.0031(4) 0.2389(3) 0.0363(8) Uani 1 1 d . . . . .
O5 O 0.1026(2) -0.0932(4) 0.1902(3) 0.0422(10) Uani 1 1 d . . . . .
O6 O 0.1779(2) -0.0511(4) 0.4095(3) 0.0415(10) Uani 1 1 d . . . . .
P1 P 0.17424(7) 0.00368(17) 0.27464(11) 0.0290(3) Uani 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'
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
O2 C1 O1 116.8(5) . . ?
O2 C1 C2 126.1(5) . . ?
O1 C1 C2 117.1(4) . . ?
C3 C2 C1 123.0(4) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C2 C3 C4 118.5(4) . . ?
C2 C3 C6 121.9(4) . . ?
C4 C3 C6 119.7(4) . . ?
C5 C4 C7 116.8(4) . . ?
C5 C4 C3 119.2(4) . . ?
C7 C4 C3 124.0(4) . . ?
C10 C5 O1 116.0(4) . . ?
C10 C5 C4 123.6(4) . . ?
O1 C5 C4 120.4(4) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C4 C7 H7 119.5 . . ?
C9 C8 C7 119.7(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
O3 C9 C8 124.1(4) . . ?
O3 C9 C10 115.1(4) . . ?
C8 C9 C10 120.8(5) . . ?
C5 C10 C9 118.1(4) . . ?
C5 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
O3 C11 P1 110.7(3) . . ?
O3 C11 H11A 109.5 . . ?
P1 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
P1 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O5 C12A C13A 107.2(18) . . ?
O5 C12A H12A 110.3 . . ?
C13A C12A H12A 110.3 . . ?
O5 C12A H12B 110.3 . . ?
C13A C12A H12B 110.3 . . ?
H12A C12A H12B 108.5 . . ?
C12A C13A H13A 109.5 . . ?
C12A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O5 C12B C13B 108.7(18) . . ?
O5 C12B H12C 109.9 . . ?
C13B C12B H12C 109.9 . . ?
O5 C12B H12D 109.9 . . ?
C13B C12B H12D 109.9 . . ?
H12C C12B H12D 108.3 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O6 C14 C15 110.3(5) . . ?
O6 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
O6 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 O1 C5 121.8(4) . . ?
C9 O3 C11 117.1(4) . . ?
C12A O5 P1 123.6(9) . . ?
C12B O5 P1 121.0(7) . . ?
C14 O6 P1 120.3(3) . . ?
O4 P1 O5 115.4(2) . . ?
O4 P1 O6 116.5(2) . . ?
O5 P1 O6 104.0(2) . . ?
O4 P1 C11 111.2(2) . . ?
O5 P1 C11 107.3(2) . . ?
O6 P1 C11 101.1(2) . . ?
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
C1 O2 1.209(5) . ?
C1 O1 1.373(6) . ?
C1 C2 1.451(7) . ?
C2 C3 1.340(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.446(6) . ?
C3 C6 1.491(7) . ?
C4 C5 1.399(6) . ?
C4 C7 1.404(6) . ?
C5 C10 1.370(6) . ?
C5 O1 1.387(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.395(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(7) . ?
C8 H8 0.9500 . ?
C9 O3 1.357(6) . ?
C9 C10 1.398(6) . ?
C10 H10 0.9500 . ?
C11 O3 1.421(4) . ?
C11 P1 1.803(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12A O5 1.423(18) . ?
C12A C13A 1.46(4) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C12B O5 1.453(19) . ?
C12B C13B 1.50(3) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14 O6 1.461(6) . ?
C14 C15 1.479(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O4 P1 1.469(3) . ?
O5 P1 1.563(4) . ?
O6 P1 1.563(4) . ?
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
O2 C1 C2 C3 -177.7(5) . . . . ?
O1 C1 C2 C3 1.0(7) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C1 C2 C3 C6 179.1(4) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C6 C3 C4 C5 179.9(4) . . . . ?
C2 C3 C4 C7 178.8(4) . . . . ?
C6 C3 C4 C7 -1.5(7) . . . . ?
C7 C4 C5 C10 1.4(6) . . . . ?
C3 C4 C5 C10 -179.9(4) . . . . ?
C7 C4 C5 O1 -177.7(4) . . . . ?
C3 C4 C5 O1 1.1(6) . . . . ?
C5 C4 C7 C8 -1.8(6) . . . . ?
C3 C4 C7 C8 179.6(4) . . . . ?
C4 C7 C8 C9 -0.2(7) . . . . ?
C7 C8 C9 O3 -178.6(4) . . . . ?
C7 C8 C9 C10 2.7(7) . . . . ?
O1 C5 C10 C9 -179.9(4) . . . . ?
C4 C5 C10 C9 1.0(6) . . . . ?
O3 C9 C10 C5 178.1(4) . . . . ?
C8 C9 C10 C5 -3.0(6) . . . . ?
O2 C1 O1 C5 179.1(4) . . . . ?
C2 C1 O1 C5 0.3(6) . . . . ?
C10 C5 O1 C1 179.6(4) . . . . ?
C4 C5 O1 C1 -1.3(6) . . . . ?
C8 C9 O3 C11 -5.6(6) . . . . ?
C10 C9 O3 C11 173.2(4) . . . . ?
P1 C11 O3 C9 174.8(3) . . . . ?
C13A C12A O5 C12B 43(3) . . . . ?
C13A C12A O5 P1 138(2) . . . . ?
C13B C12B O5 C12A -69(3) . . . . ?
C13B C12B O5 P1 -173(2) . . . . ?
C15 C14 O6 P1 96.1(5) . . . . ?
C12A O5 P1 O4 -28.7(18) . . . . ?
C12B O5 P1 O4 6.1(19) . . . . ?
C12A O5 P1 O6 -157.5(18) . . . . ?
C12B O5 P1 O6 -122.7(19) . . . . ?
C12A O5 P1 C11 95.9(18) . . . . ?
C12B O5 P1 C11 130.6(19) . . . . ?
C14 O6 P1 O4 -46.4(4) . . . . ?
C14 O6 P1 O5 81.8(4) . . . . ?
C14 O6 P1 C11 -167.0(4) . . . . ?
O3 C11 P1 O4 173.3(3) . . . . ?
O3 C11 P1 O5 46.2(4) . . . . ?
O3 C11 P1 O6 -62.4(4) . . . . ?
