Identification of organophosphorus simulants for the development of next-generation detection technologies.
Ellaby, Rebecca J.; Clark, Ewan R.; Allen, Nyasha; Taylor, Faith R.; Ng, Kendrick K. L.; Dimitrovski, Milan; Chu, Dominique F.; Mulvihill, Daniel P.; Hiscock, Jennifer R.; Organic & biomolecular chemistry 19 (2021) 2008–2014; doi:10.1039/d0ob02523b

data_7157891
_publ_section_title
;
 Identification of organophosphorus simulants for the development of
 next-generation detection technologies.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2008
_journal_page_last               2014
_journal_paper_doi               10.1039/d0ob02523b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C15 H10 F6 N2 S, C2 H6 O S'
_chemical_formula_sum            'C17 H16 F6 N2 O S2'
_chemical_formula_weight         442.44
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-13 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.831(20)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5039(12)
_cell_length_b                   8.281(2)
_cell_length_c                   24.124(8)
_cell_measurement_reflns_used    778
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      69.1850
_cell_measurement_theta_min      4.6610
_cell_volume                     1885.1(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 1.000
_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    -68.00  31.00   1.00   19.77    --  -41.91  57.00 -60.00   99
  2  \w   -113.00 -19.00   1.00   19.77    --  -41.91 -57.00 150.00   94
  3  \w    -31.00  64.00   1.00   19.77    --   41.91 -38.00   0.00   95
  4  \w     58.00  99.00   1.00   19.77    --   41.91-133.00 107.00   41
  5  \w     53.00  89.00   1.00   30.00    --  105.91  15.00  90.00   36
  6  \w     34.00 117.00   1.00   30.00    --  105.91-125.00  90.00   83
  7  \w     56.00 107.00   1.00   30.00    --  105.91 -94.00 120.00   51
  8  \w     33.00 125.00   1.00   30.00    --  105.91 -45.00  30.00   92
  9  \w     35.00  87.00   1.00   30.00    --  105.91 -61.00 150.00   52
 10  \w     71.00 108.00   1.00   30.00    --  105.91 -94.00-150.00   37
 11  \w    108.00 173.00   1.00   30.00    --  105.91  61.00 120.00   65
 12  \w    126.00 178.00   1.00   30.00    --  105.91  15.00  90.00   52
 13  \w     56.00 109.00   1.00   30.00    --  105.91 -94.00 -60.00   53
 14  \w     40.00 109.00   1.00   30.00    --  105.91 -45.00 -90.00   69
 15  \w     44.00 132.00   1.00   30.00    --  105.91 -45.00-180.00   88
 16  \w     54.00 160.00   1.00   30.00    --  105.91  15.00-120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0049745000
_diffrn_orient_matrix_UB_12      -0.1151704000
_diffrn_orient_matrix_UB_13      -0.0504326000
_diffrn_orient_matrix_UB_21      0.0231943000
_diffrn_orient_matrix_UB_22      -0.1451562000
_diffrn_orient_matrix_UB_23      0.0399835000
_diffrn_orient_matrix_UB_31      -0.1613761000
_diffrn_orient_matrix_UB_32      -0.0170868000
_diffrn_orient_matrix_UB_33      -0.0004519000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1420
_diffrn_reflns_av_unetI/netI     0.1376
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11491
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.691
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.011
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0709
_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^)+(0.0478P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1755
_reflns_number_total             3331
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02523b2.cif
_cod_data_source_block           2018jrh0036_res
_cod_depositor_comments          'Adding full bibliography for 7157891.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157891
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O2
_chemical_oxdiff_usercomment     '100 K rebecca 1/1 + 1/5'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Others
 Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(S2A)=1-FVAR(1)
 Sof(S2)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(2)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(2)
 Sof(F5A)=Sof(F6A)=Sof(F4A)=1-FVAR(3)
 Sof(F6)=Sof(F5)=Sof(F4)=FVAR(3)
3.a Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C16(H16D,H16E,H16F), C17(H17A,H17B,H17C), C17(H17D,H17E,
 H17F)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C11(H11), C6(H6), C13(H13), C12(H12), C3(H3), C4(H4),
 C10(H10), C5(H5)
;
_shelx_res_checksum              46511
_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 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.694