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_1548663
_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         '2(C18 H15 O P), H3 O4 P'
_chemical_formula_sum            'C36 H33 O6 P3'
_chemical_formula_weight         654.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_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                87.898(5)
_cell_angle_beta                 88.392(5)
_cell_angle_gamma                66.732(5)
_cell_formula_units_Z            4
_cell_length_a                   12.8859(7)
_cell_length_b                   16.1958(8)
_cell_length_c                   16.3976(11)
_cell_measurement_reflns_used    11170
_cell_measurement_temperature    122.97(11)
_cell_measurement_theta_max      32.1590
_cell_measurement_theta_min      3.6560
_cell_volume                     3141.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (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      N~2~
_diffrn_ambient_temperature      122.97(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.975
_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    -20.00  68.00   0.50  175.00    --   26.19 -99.00 -60.00  176
  2  \w      6.00  44.00   0.50  175.00    --   26.19  57.00-180.00   76
  3  \w    -41.00  63.00   0.50  175.00    --   26.19 -19.00 120.00  208
  4  \w     28.00  73.00   0.50  175.00    --   26.19-108.00-133.00   90
  5  \w     -4.00  96.00   0.50  175.00    --   26.19  77.00  60.00  200
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0593678000
_diffrn_orient_matrix_UB_12      -0.0145905000
_diffrn_orient_matrix_UB_13      0.0037470000
_diffrn_orient_matrix_UB_21      0.0072103000
_diffrn_orient_matrix_UB_22      -0.0100327000
_diffrn_orient_matrix_UB_23      -0.0420748000
_diffrn_orient_matrix_UB_31      -0.0042880000
_diffrn_orient_matrix_UB_32      0.0442574000
_diffrn_orient_matrix_UB_33      -0.0096244000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            12525
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.416
_diffrn_reflns_theta_min         3.163
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
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    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     836
_refine_ls_number_reflns         12525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0740
_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/[\s^2^(Fo^2^)+(0.0663P)^2^+7.6589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1930
_refine_ls_wR_factor_ref         0.2023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10490
_reflns_number_total             12525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jp7b11299_si_003.cif
_cod_data_source_block           ilya_sn2_neu_tw
_cod_database_code               1548663
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C18 H18 P2 O4'
_chemical_oxdiff_usercomment     'Ilya Shenderovich'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 96.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.751(2)
 0.249(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C00U(H00U), C00Y(H00Y), C00Z(H00Z), C011(H011), C013(H013), C014(H014),
 C016(H016), C017(H017), C018(H018), C019(H019), C01B(H01B), C01C(H01C),
 C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I),
 C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N), C01O(H01O),
 C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S), C01T(H01T), C01U(H01U),
 C01V(H01V), C01W(H01W), C01X(H01X), C01Y(H01Y), C01Z(H01Z), C020(H020),
 C021(H021), C022(H022), C023(H023), C024(H024), C025(H025), C026(H026),
 C027(H027), C028(H028), C029(H029), C02A(H02A), C02B(H02B), C02C(H02C),
 C02D(H02D), C02E(H02E), C02F(H02F), C02G(H02G), C02H(H02H), C02I(H02I)
;
_shelx_res_checksum              82675
_shelx_hkl_checksum              34433
_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 1.529
_oxdiff_exptl_absorpt_empirical_full_min 0.717