Oxoammonium salt-promoted diverse functionalization of saturated cyclic amines with dinucleophiles.
He, Yan; Liu, Qimeng; Yang, Jintao; Liu, Yunfei; Zhang, Xinying; Fan, Xuesen; Chemical communications (Cambridge, England) 59 (2023) 3874–3877; doi:10.1039/d2cc06936a

data_7131366
_publ_section_title
;
 Oxoammonium salt-promoted diverse functionalization of saturated cyclic
 amines with dinucleophiles.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3874
_journal_page_last               3877
_journal_paper_doi               10.1039/d2cc06936a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C12 H14 N2 O S'
_chemical_formula_sum            'C12 H14 N2 O S'
_chemical_formula_weight         234.31
_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             2020-02-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2022-12-20 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.917(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7386(4)
_cell_length_b                   13.7675(5)
_cell_length_c                   15.6087(5)
_cell_measurement_reflns_used    5686
_cell_measurement_temperature    295.25(16)
_cell_measurement_theta_max      27.5650
_cell_measurement_theta_min      3.5780
_cell_volume                     2307.35(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.25(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.891
_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     14.00  39.00   1.00    5.75    --   16.05-129.00  37.00   25
  2  \w     20.00  45.00   1.00    5.75    --   16.05-141.00-134.00   25
  3  \w    -73.00 -48.00   1.00    5.75    --  -16.83 129.00 110.00   25
  4  \w    -79.00 -54.00   1.00    5.75    --  -16.83 141.00 -76.00   25
  5  \w    -10.00  82.00   1.00    5.75    --   16.05  77.00 -30.00   92
  6  \w    -50.00  43.00   1.00    5.75    --   16.05 -77.00 120.00   93
  7  \w     35.00  64.00   1.00    5.75    --   16.05 178.00  30.00   29
  8  \w     -4.00  38.00   1.00    5.75    --  -16.83  19.00-180.00   42
  9  \w    -46.00 -17.00   1.00    5.75    --  -16.83  19.00-180.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0254428000
_diffrn_orient_matrix_UB_12      -0.0128281000
_diffrn_orient_matrix_UB_13      -0.0401053000
_diffrn_orient_matrix_UB_21      -0.0089523000
_diffrn_orient_matrix_UB_22      -0.0498720000
_diffrn_orient_matrix_UB_23      0.0095073000
_diffrn_orient_matrix_UB_31      -0.0602769000
_diffrn_orient_matrix_UB_32      0.0020174000
_diffrn_orient_matrix_UB_33      -0.0191575000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18532
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.963
_diffrn_reflns_theta_min         3.252
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0453P)^2^+0.7836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3877
_reflns_number_total             5454
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06936a2.cif
_cod_data_source_block           hy-20190706
_cod_depositor_comments
;
        Adding full bibliography for 7131366.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H28 N4 O2 S2'
_cod_original_formula_weight         468.62
_cod_original_formula_moiety         '2(C12 H14 N2 O S)'
_cod_original_formula_units_Z            4
_cod_database_code               7131366
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.950
_diffrn_oxdiff_digest_frames
;
016a8f259ad2efefc30b767f296d5bcbad000274cd3
;
_diffrn_oxdiff_digest_hkl
;
010aa5b3c4b8b7d4123e7aa190b4cf53b11de5
;
_reflns_odcompleteness_completeness 99.61
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2A), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), N4(H4), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23)
;
_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.552