The synergistic co-operation of N—H···O=P hydrogen bonds and C—H···O<i>X</i> weak intermolecular interactions (<i>X</i> is =P or —C) in the (CH~3~O)~2~P(O)(NH–NHC~6~F~5~) amidophosphoester: a combined X-ray crystallographic and theoretical study
Vahdani Alviri, Banafsheh; Pourayoubi, Mehrdad; Farhadipour, Abolghasem; Kaur, Manpreet; Jasinski, Jerry P.; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S2053229619011641

data_2021773
_publ_section_title
;
 The synergistic co-operation of N---H&#x00B7;&#x00B7;&#x00B7;O=P hydrogen
 bonds and C---H&#x00B7;&#x00B7;&#x00B7;O<i>X</i> weak intermolecular
 interactions (<i>X</i> is =P or ---C) in the
 (CH~3~O)~2~P(O)(NH--NHC~6~F~5~) amidophosphoester: a combined X-ray
 crystallographic and theoretical study
;
_journal_coeditor_code           QS3086
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619011641
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C8 H8 F5 N2 O3 P'
_chemical_formula_moiety         'C8 H8 F5 N2 O3 P'
_chemical_formula_sum            'C8 H8 F5 N2 O3 P'
_chemical_formula_weight         306.13
_chemical_name_systematic
;
<i>O</i>,<i>O</i>'-Dimethyl
[(2,3,4,5,6-pentafluorophenylhydrazinyl]phosphonate
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.647(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5273(2)
_cell_length_b                   10.3266(3)
_cell_length_c                   21.1193(5)
_cell_measurement_reflns_used    4434
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.6440
_cell_measurement_theta_min      3.4160
_cell_volume                     2293.46(10)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>,  2009) and
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18096
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.819
_diffrn_reflns_theta_min         3.321
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.493
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         7628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0522P)^2^+0.6442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                5724
_reflns_number_total             7628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            qs3086sup1.cif
_cod_data_source_block           I
_cod_database_code               2021773
_cod_database_fobs_code          2021773
_shelx_estimated_absorpt_t_min   0.901
_shelx_estimated_absorpt_t_max   0.963
_shelx_hkl_checksum              94357
_shelx_res_checksum              216