Extensive analysis of N—H···O hydrogen bonding in four classes of phosphorus compounds: a combined experimental and database study
Hamzehee, Farahnaz; Pourayoubi, Mehrdad; Nečas, Marek; Choquesillo-Lazarte, Duane; Acta Crystallographica Section C 73 (2017) –; doi:10.1107/S2053229617001516

data_2020717
_publ_section_title
;
 Extensive analysis of N---H&#x00B7;&#x00B7;&#x00B7;O hydrogen bonding in
 four classes of phosphorus compounds: a combined experimental and
 database study
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229617001516
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C8 H12 N1 +, C14 H15 N1 O2 P -'
_chemical_formula_moiety         'C8 H12 N1 +, C14 H15 N1 O2 P -'
_chemical_formula_sum            'C22 H27 N2 O2 P'
_chemical_formula_weight         382.43
_chemical_melting_point          436
_chemical_name_systematic
;
(<i>S</i>)-1-Phenylethylammonium
<i>N</i>-[(<i>S</i>)-1-phenylethyl]phenylphosphonamidate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.36290(10)
_cell_length_b                   13.7260(3)
_cell_length_c                   27.8653(6)
_cell_measurement_reflns_used    7210
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.5310
_cell_measurement_theta_min      2.0610
_cell_volume                     2051.20(7)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al</i>., 2008)
;
_computing_publication_material
;
enCIFer (Allen <i>et al</i>., 2004
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  Multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            11806
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.226
_refine_ls_abs_structure_details
;
Flack (1983), 1551 Friedel pairs
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3764
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.4266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                3557
_reflns_number_total             3764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ky3108sup1.cif
_cod_data_source_block           III
_cod_database_code               2020717
_cod_database_fobs_code          2020717