One-pot Synthesis of α-sulfoximinophosphonate via Kabachnik–Fields Reactions
Natarajan, K.; Sharma, Suraj; C. P., Irfana Jesin; Kataria, Ramesh; Nandi, Ganesh Chandra; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01355J

data_7158829
_publ_section_title
;
 One-pot Synthesis of \a-sulfoximinophosphonate via Kabachnik--Fields
 Reactions
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01355J
_journal_year                    2022
_chemical_formula_moiety         'C23 H23 Br2 N2 O6 P S'
_chemical_formula_sum            'C23 H23 Br2 N2 O6 P S'
_chemical_formula_weight         646.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-01
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2022-04-28 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                73.419(5)
_cell_angle_beta                 86.038(4)
_cell_angle_gamma                82.267(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8628(3)
_cell_length_b                   11.0438(6)
_cell_length_c                   12.7968(7)
_cell_measurement_reflns_used    6688
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.0920
_cell_measurement_theta_min      3.3220
_cell_volume                     1323.06(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.937
_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    -41.00 -13.00   0.50   10.00    --   -9.95  99.00-174.00   56
  2  \w    -11.00  39.00   0.50   10.00    --   10.22 -99.00  79.00  100
  3  \w    -18.00   7.00   0.50   10.00    --   -9.95  19.00   0.00   50
  4  \w    -19.00  53.00   0.50   10.00    --   -9.95  38.00-150.00  144
  5  \w    -50.00 -24.00   0.50   10.00    --   -9.95 125.00-180.00   52
  6  \w     13.00  48.00   0.50   10.00    --   -9.95  19.00   0.00   70
  7  \w     20.00  45.00   0.50   10.00    --   -9.95  19.00 -30.00   50
  8  \w    -21.00  15.00   0.50   10.00    --   -9.95  19.00 -30.00   72
  9  \w    -54.00 -19.00   0.50   10.00    --   -9.95 125.00-150.00   70
 10  \w     -9.00  19.00   0.50   10.00    --   -9.95  99.00-174.00   56
 11  \w    -42.00 -15.00   0.50   10.00    --   10.22 131.00 -77.66   54
 12  \w    -10.00  75.00   0.50   10.00    --   10.22  77.00   0.00  170
 13  \w    -30.00  -3.00   0.50   10.00    --   10.22 125.00 157.21   54
 14  \w    -23.00   4.00   0.50   10.00    --   10.22 117.00  34.59   54
 15  \w      3.00  59.00   0.50   10.00    --   10.22-125.00-180.00  112
 16  \w    -19.00  40.00   0.50   10.00    --   10.22 -99.00 120.00  118
 17  \w    -60.00   1.00   0.50   10.00    --   10.22 -19.00-150.00  122
 18  \w    -52.00 -26.00   0.50   10.00    --   10.22 -38.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0150301000
_diffrn_orient_matrix_UB_12      0.0364779000
_diffrn_orient_matrix_UB_13      0.0377745000
_diffrn_orient_matrix_UB_21      -0.0383417000
_diffrn_orient_matrix_UB_22      0.0481189000
_diffrn_orient_matrix_UB_23      -0.0398248000
_diffrn_orient_matrix_UB_31      -0.0598070000
_diffrn_orient_matrix_UB_32      -0.0301725000
_diffrn_orient_matrix_UB_33      0.0183088000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18053
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.374
_diffrn_reflns_theta_min         3.324
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_preparation       Synthesized
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0387P)^2^+0.8194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3389
_reflns_number_total             5636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01355j2.cif
_cod_data_source_block           rk-kn4fa
_cod_database_code               7158829
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O S Br P'
_diffrn_oxdiff_ac3_digest_frames
;
0127083687b851d25f75efbce25f487981000252ff9
;
_diffrn_oxdiff_ac3_digest_hkl
;
012037d630cbbd5eda47ba0a53e1d55408d997
;
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C17(H17), C4(H4), C19(H19), C20(H20), C13(H13), C7(H7), C16(H16),
 C6(H6), C23(H23), C14(H14), C22(H22)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_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 1.287
_oxdiff_exptl_absorpt_empirical_full_min 0.814