data_13c

_publ_contact_author
;
Maciej Kubicki   
Faculty of Chemistry 
Adam Mickiewicz University
Grunwaldzka 6              
60-780 Poznań   
Poland             
;
_publ_contact_author_email           mkubicki@amu.edu.pl

_journal_name_full                   'Chem.Eur.J.'

loop_
_publ_author_name
_publ_author_address
'Kaźmierczak, Marcin'
;  Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
'Koroniak, Henryk'
;  Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
'Kubicki, Maciej'
;
Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
 
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety        'C10 H24 F N O3 P, C2 H O4, D2 O'
_chemical_formula_sum             'C12 H25 D2 F N O8 P' 
_chemical_formula_weight          365.33

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'
 'F'  'F'   0.0171   0.0103
 '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'
 'D'  'D'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    6.34660(18)
_cell_length_b                    12.0072(3)
_cell_length_c                    24.5409(7)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1870.14(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(1)
_cell_measurement_reflns_used   4300
_cell_measurement_theta_min     3.3890
_cell_measurement_theta_max     26.6260
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.298          
_exptl_crystal_F_000              776
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.3
_exptl_crystal_size_mid           0.1
_exptl_crystal_size_min           0.1
_exptl_absorpt_coefficient_mu     0.192
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_T_min                   0.92955
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_correction_type            multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature       100(1)
_diffrn_ambient_environment N~2~
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos'
_diffrn_detector 'CCD plate'
_diffrn_detector_type Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number             10638
_diffrn_reflns_av_unetI/netI      0.0434
_diffrn_reflns_av_R_equivalents   0.0243
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        30
_diffrn_reflns_theta_min          3.316
_diffrn_reflns_theta_max          26.913
_diffrn_reflns_theta_full         25.000
_diffrn_measured_fraction_theta_max   0.944
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.944
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.910
_diffrn_reflns_point_group_measured_fraction_full  0.986
_reflns_number_total              3680
_reflns_number_gt                 3313
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.664
_reflns_Friedel_fraction_max      0.865
_reflns_Friedel_fraction_full     0.969
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection     'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement     'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction      'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution     'SHELXT-2013 (Sheldrick, 2015)' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2015)'
_computing_molecular_graphics     'Mercury (MacRae et al., 2009)'
_computing_publication_material   'SHELXL-2013 (Sheldrick, 2015)'

_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0266P)²+0.4747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      .
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1163 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.04(5)
_chemical_absolute_configuration  rmad
_refine_ls_number_reflns          3680
_refine_ls_number_parameters      217
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0484
_refine_ls_R_factor_gt            0.0406
_refine_ls_wR_factor_ref          0.0753
_refine_ls_wR_factor_gt           0.0727
_refine_ls_goodness_of_fit_ref    1.056
_refine_ls_restrained_S_all       1.056
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
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 0.66501(11) 0.32021(6) 0.38961(3) 0.01680(17) Uani 1 1 d . . . . .
O2 O 0.8216(3) 0.38094(18) 0.35729(9) 0.0279(5) Uani 1 1 d . . . . .
O3 O 0.7002(3) 0.19153(16) 0.39455(8) 0.0209(5) Uani 1 1 d . . . . .
C4 C 0.8110(5) 0.1269(2) 0.35233(13) 0.0250(7) Uani 1 1 d . . . . .
H4A H 0.9641 0.1426 0.3535 0.030 Uiso 1 1 calc R U . . .
H4B H 0.7574 0.1467 0.3157 0.030 Uiso 1 1 calc R U . . .
C5 C 0.7706(6) 0.0062(3) 0.36397(15) 0.0389(9) Uani 1 1 d . . . . .
H5A H 0.8457 -0.0397 0.3373 0.058 Uiso 1 1 calc R U . . .
H5B H 0.6190 -0.0087 0.3615 0.058 Uiso 1 1 calc R U . . .
H5C H 0.8205 -0.0118 0.4007 0.058 Uiso 1 1 calc R U . . .
O6 O 0.6358(3) 0.35730(16) 0.45008(8) 0.0214(5) Uani 1 1 d . . . . .
C7 C 0.8111(5) 0.3500(3) 0.48895(13) 0.0287(8) Uani 1 1 d . . . . .
H7A H 0.9469 0.3601 0.4697 0.034 Uiso 1 1 calc R U . . .
H7B H 0.8118 0.2760 0.5067 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7833(7) 0.4386(3) 0.53037(16) 0.0609(14) Uani 1 1 d . . . . .
H8A H 0.7882 0.5117 0.5126 0.091 Uiso 1 1 calc R U . . .
H8B H 0.8965 0.4336 0.5574 0.091 Uiso 1 1 calc R U . . .
H8C H 0.6469 0.4292 0.5485 0.091 Uiso 1 1 calc R U . . .
C9 C 0.4052(4) 0.3413(2) 0.36033(13) 0.0159(6) Uani 1 1 d . . . . .
H9 H 0.4044 0.3046 0.3238 0.019 Uiso 1 1 calc R U . . .
F9 F 0.2515(2) 0.28835(13) 0.39231(7) 0.0228(4) Uani 1 1 d . . . . .
C10 C 0.3499(4) 0.4633(2) 0.35167(11) 0.0143(6) Uani 1 1 d . . . . .
H10 H 0.4767 0.5013 0.3362 0.017 Uiso 1 1 calc R U . . .
N10 N 0.1757(4) 0.47207(17) 0.31069(9) 0.0154(5) Uani 1 1 d . . . . .
H10A H 0.2106 0.4327 0.2803 0.018 Uiso 1 1 calc R U . . .
H10B H 0.1557 0.5448 0.3017 0.018 Uiso 1 1 calc R U . . .
H10C H 0.0549 0.4440 0.3252 0.018 Uiso 1 1 calc R U . . .
C11 C 0.2851(5) 0.5262(2) 0.40344(11) 0.0208(7) Uani 1 1 d . . . . .
H11A H 0.1325 0.5148 0.4096 0.025 Uiso 1 1 calc R U . . .
H11B H 0.3612 0.4938 0.4349 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3298(6) 0.6514(2) 0.40131(14) 0.0341(8) Uani 1 1 d . . . . .
H12 H 0.2769 0.6808 0.3657 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5658(6) 0.6751(3) 0.40487(15) 0.0460(11) Uani 1 1 d . . . . .
H13A H 0.6185 0.6518 0.4406 0.069 Uiso 1 1 calc R U . . .
H13B H 0.5907 0.7550 0.4000 0.069 Uiso 1 1 calc R U . . .
H13C H 0.6396 0.6336 0.3763 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2111(7) 0.7102(3) 0.44706(18) 0.0610(13) Uani 1 1 d . . . . .
H14A H 0.0593 0.6987 0.4423 0.091 Uiso 1 1 calc R U . . .
H14B H 0.2424 0.7901 0.4460 0.091 Uiso 1 1 calc R U . . .
H14C H 0.2553 0.6794 0.4823 0.091 Uiso 1 1 calc R U . . .
C1A C 0.8562(5) 0.7103(2) 0.26871(11) 0.0154(6) Uani 1 1 d . . . . .
O11A O 1.0425(3) 0.69040(16) 0.28273(8) 0.0203(5) Uani 1 1 d . . . . .
O12A O 0.7671(3) 0.80261(15) 0.26613(8) 0.0184(5) Uani 1 1 d . . . . .
C2A C 0.7195(4) 0.6088(2) 0.25178(12) 0.0160(6) Uani 1 1 d . . . . .
O21A O 0.8322(3) 0.52193(15) 0.23898(9) 0.0242(5) Uani 1 1 d . . . . .
H21A H 0.7522 0.4685 0.2312 0.036 Uiso 1 1 calc R U . . .
O22A O 0.5293(3) 0.61342(17) 0.25171(9) 0.0252(5) Uani 1 1 d . . . . .
O1W O 0.6510(3) 0.34860(15) 0.20817(10) 0.0262(5) Uani 1 1 d G . . . .
D1A D 0.5335 0.3241 0.2196 0.039 Uiso 1 1 d G U . . .
D1B D 0.7440 0.2981 0.2111 0.039 Uiso 1 1 d G U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 O2 1.466(2) . ?
P1 O6 1.560(2) . ?
P1 O3 1.566(2) . ?
P1 C9 1.816(3) . ?
O3 C4 1.473(3) . ?
C4 C5 1.499(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O6 C7 1.468(3) . ?
C7 C8 1.482(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 F9 1.404(3) . ?
C9 C10 1.522(4) . ?
C9 H9 1.0000 . ?
C10 N10 1.499(3) . ?
C10 C11 1.534(4) . ?
C10 H10 1.0000 . ?
N10 H10A 0.9100 . ?
N10 H10B 0.9100 . ?
N10 H10C 0.9100 . ?
C11 C12 1.532(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.525(5) . ?
C12 C13 1.527(5) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C1A O12A 1.246(3) . ?
C1A O11A 1.254(3) . ?
C1A C2A 1.553(4) . ?
C2A O22A 1.208(3) . ?
C2A O21A 1.303(3) . ?
O21A H21A 0.8400 . ?
O1W D1A 0.8496 . ?
O1W D1B 0.8496 . ?
 
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 P1 O6 116.95(13) . . ?
O2 P1 O3 115.86(12) . . ?
O6 P1 O3 103.00(11) . . ?
O2 P1 C9 109.40(13) . . ?
O6 P1 C9 103.20(13) . . ?
O3 P1 C9 107.32(12) . . ?
C4 O3 P1 122.26(18) . . ?
O3 C4 C5 107.1(2) . . ?
O3 C4 H4A 110.3 . . ?
C5 C4 H4A 110.3 . . ?
O3 C4 H4B 110.3 . . ?
C5 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
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 . . ?
C7 O6 P1 120.72(18) . . ?
O6 C7 C8 108.2(3) . . ?
O6 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
O6 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F9 C9 C10 110.7(2) . . ?
F9 C9 P1 110.28(18) . . ?
C10 C9 P1 113.49(19) . . ?
F9 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
P1 C9 H9 107.4 . . ?
N10 C10 C9 109.3(2) . . ?
N10 C10 C11 108.9(2) . . ?
C9 C10 C11 114.8(2) . . ?
N10 C10 H10 107.9 . . ?
C9 C10 H10 107.9 . . ?
C11 C10 H10 107.9 . . ?
C10 N10 H10A 109.5 . . ?
C10 N10 H10B 109.5 . . ?
H10A N10 H10B 109.5 . . ?
C10 N10 H10C 109.5 . . ?
H10A N10 H10C 109.5 . . ?
H10B N10 H10C 109.5 . . ?
C12 C11 C10 113.9(2) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C14 C12 C13 110.9(3) . . ?
C14 C12 C11 109.7(3) . . ?
C13 C12 C11 111.2(3) . . ?
C14 C12 H12 108.3 . . ?
C13 C12 H12 108.3 . . ?
C11 C12 H12 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O12A C1A O11A 127.7(3) . . ?
O12A C1A C2A 115.5(2) . . ?
O11A C1A C2A 116.8(2) . . ?
O22A C2A O21A 125.8(3) . . ?
O22A C2A C1A 121.5(3) . . ?
O21A C2A C1A 112.7(2) . . ?
C2A O21A H21A 109.5 . . ?
D1A O1W D1B 109.5 . . ?
 
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 P1 O3 C4 -27.6(2) . . . . ?
O6 P1 O3 C4 -156.5(2) . . . . ?
C9 P1 O3 C4 95.0(2) . . . . ?
P1 O3 C4 C5 -166.9(2) . . . . ?
O2 P1 O6 C7 -61.6(2) . . . . ?
O3 P1 O6 C7 66.7(2) . . . . ?
C9 P1 O6 C7 178.3(2) . . . . ?
P1 O6 C7 C8 150.6(3) . . . . ?
O2 P1 C9 F9 -177.03(18) . . . . ?
O6 P1 C9 F9 -51.9(2) . . . . ?
O3 P1 C9 F9 56.5(2) . . . . ?
O2 P1 C9 C10 -52.1(2) . . . . ?
O6 P1 C9 C10 73.0(2) . . . . ?
O3 P1 C9 C10 -178.6(2) . . . . ?
F9 C9 C10 N10 -75.3(3) . . . . ?
P1 C9 C10 N10 160.01(18) . . . . ?
F9 C9 C10 C11 47.3(3) . . . . ?
P1 C9 C10 C11 -77.3(3) . . . . ?
N10 C10 C11 C12 -84.3(3) . . . . ?
C9 C10 C11 C12 152.8(3) . . . . ?
C10 C11 C12 C14 165.5(3) . . . . ?
C10 C11 C12 C13 -71.4(3) . . . . ?
O12A C1A C2A O22A -20.7(4) . . . . ?
O11A C1A C2A O22A 160.0(3) . . . . ?
O12A C1A C2A O21A 160.1(3) . . . . ?
O11A C1A C2A O21A -19.2(4) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N10 H10A O12A  0.91 1.94 2.798(3) 156.6 3_645
N10 H10B O11A  0.91 1.95 2.839(3) 166.3 1_455
N10 H10C O2  0.91 1.84 2.749(3) 176.2 1_455
O21A H21A O1W  0.84 1.68 2.495(3) 164.7 .
O1W D1A O12A  0.85 1.96 2.783(3) 163.9 3_645
O1W D1B O11A  0.85 1.88 2.728(3) 177.9 3_745
 
_refine_diff_density_max    0.246
_refine_diff_density_min   -0.294
_refine_diff_density_rms    0.046



