P═O Moiety as an Ambidextrous Hydrogen Bond Acceptor
Tupikina, Elena Yu.; Bodensteiner, Michael; Tolstoy, Peter M.; Denisov, Gleb S.; Shenderovich, Ilya G.; The Journal of Physical Chemistry C  (2018) –; doi:10.1021/acs.jpcc.7b11299

data_1548665
_publ_section_title
;
 P&#x2550;O Moiety as an Ambidextrous Hydrogen Bond Acceptor
;
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_paper_doi               10.1021/acs.jpcc.7b11299
_journal_year                    2018
_chemical_formula_moiety         'C6 H18 N3 O P, H3 O4 P'
_chemical_formula_sum            'C6 H21 N3 O5 P2'
_chemical_formula_weight         277.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-21
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.5031(19)
_cell_angle_gamma                90
_cell_formula_units_Z            20
_cell_length_a                   19.4469(4)
_cell_length_b                   9.4267(2)
_cell_length_c                   36.0286(8)
_cell_measurement_reflns_used    36475
_cell_measurement_temperature    291.33(10)
_cell_measurement_theta_max      28.8590
_cell_measurement_theta_min      3.1100
_cell_volume                     6592.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.33(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -52.00  48.00   0.50   22.50    --   17.79 -77.00 150.00  200
  2  \w    -91.00  26.00   0.50   22.50    --  -18.26 -19.00   0.00  234
  3  \w    -87.00   3.00   0.50   22.50    --  -18.26 -57.00 -60.00  180
  4  \w    -81.00  -7.00   0.50   22.50    --  -18.26 133.00-141.04  148
  5  \w     -4.00  54.00   0.50   22.50    --   17.79  57.00 -90.00  116
  6  \w    -94.00 -35.00   0.50   22.50    --  -18.26-178.00 -60.00  118
  7  \w    -91.00   7.00   0.50   22.50    --  -18.26 -38.00 150.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0299624000
_diffrn_orient_matrix_UB_12      -0.0325922000
_diffrn_orient_matrix_UB_13      -0.0084118000
_diffrn_orient_matrix_UB_21      -0.0019095000
_diffrn_orient_matrix_UB_22      0.0533931000
_diffrn_orient_matrix_UB_23      -0.0138921000
_diffrn_orient_matrix_UB_31      0.0208264000
_diffrn_orient_matrix_UB_32      -0.0417998000
_diffrn_orient_matrix_UB_33      -0.0112033000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            79597
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.126
_diffrn_reflns_theta_min         2.905
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.37b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             2960
_exptl_crystal_size_max          0.755
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     854
_refine_ls_number_reflns         16032
_refine_ls_number_restraints     274
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0415
_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/[\s^2^(Fo^2^)+(0.0416P)^2^+4.8136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13443
_reflns_number_total             16032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jp7b11299_si_004.cif
_cod_data_source_block           sn104
_cod_database_code               1548665
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C12 H20 O12 P4 N12'
_chemical_oxdiff_usercomment     'Ilya Shendarovich'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 P1-N1A \\sim P1-N1 \\sim P1-N2 \\sim P1-N2A \\sim P1-N3 \\sim P1-N3A
 with sigma of 0.02
 N2-C3 \\sim N2-C4 \\sim N2A-C4 \\sim N2A-C3A \\sim N3-C6 \\sim N3-C5 \\sim
N3A-C5 \\sim N1-C2 \\sim N1-C1 ~
 N1A-C2A \\sim N1A-C1A
 with sigma of 0.02
 N15-C30A \\sim N15-C30 \\sim N15-C29 \\sim N15-C29A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2 \\sim N3 \\sim N1 \\sim N2A \\sim N3A \\sim N1A \\sim C4 \\sim C5 \\sim C6
\\sim C3 \\sim C1 \\sim C2 \\sim C3A \\sim C1A \\sim C6A \\sim C2A \\sim P1:
within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
P10 \\sim N15 \\sim C30A \\sim C30 \\sim C29 \\sim C29A: within 1.7A with sigma
of 0.002 and sigma for terminal atoms of 0.002
4. Others
 Sof(H4BD)=Sof(H4BE)=Sof(H4BF)=Sof(H5BD)=Sof(H5BE)=Sof(H5BF)=Sof(N2A)=Sof(N3A)=
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(N1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(H2AC)=1-FVAR(1)
 Sof(N2)=Sof(N3)=Sof(N1)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=Sof(H5AA)=Sof(H5AB)=
 Sof(H5AC)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=
 FVAR(1)
 Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=Sof(C29A)=Sof(H29D)=Sof(H29E)=
 Sof(H29F)=1-FVAR(2)
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=
 FVAR(2)
5.a Me refined with riding coordinates:
 C29A(H29D,H29E,H29F)
5.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C), C26(H26A,H26B,H26C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C13(H13A,H13B,
 H13C), C28(H28A,H28B,H28C), C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C4(H4AA,
 H4AB,H4AC), C4(H4BD,H4BE,H4BF), C20(H20A,H20B,H20C), C25(H25A,H25B,H25C),
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C24(H24A,H24B,H24C), C27(H27A,H27B,
 H27C), C23(H23A,H23B,H23C), C19(H19A,H19B,H19C), C8(H8A,H8B,H8C), C5(H5AA,H5AB,
 H5AC), C5(H5BD,H5BE,H5BF), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C6(H6A,
 H6B,H6C), C30(H30A,H30B,H30C), C3(H3A,H3B,H3C), C29(H29A,H29B,H29C), C1(H1A,
 H1B,H1C), C2(H2A,H2B,H2C), C3A(H3AA,H3AB,H3AC), C1A(H1AA,H1AB,H1AC), C6A(H6AA,
 H6AB,H6AC), C2A(H2AA,H2AB,H2AC), C30A(H30D,H30E,H30F)
5.c Idealised tetrahedral OH refined as rotating group:
 O11(H11), O9(H9), O10(H10), O19(H19), O7(H7), O13(H13), O22(H22), O5(H5),
 O14(H14), O4(H4), O15(H15), O16(H16), O21(H21), O6(H6), O17(H17)
;
_shelx_res_checksum              80380
_shelx_hkl_checksum              10894
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.558
_oxdiff_exptl_absorpt_empirical_full_min 0.576