A greener approach towards the synthesis of N-heterocyclic thiones and selones using mechanochemical technique
Sanjay Kumar, Siddharth; Rangarajan, Shalini; Kunchur, Harish S.; Balakrishna, Maravanji Shivaramaiah; Dalton Transactions  (2022) –; doi:10.1039/D2DT02322A

data_7711332
_publ_section_title
;
 A greener approach towards the synthesis of N-heterocyclic thiones and
 selones using mechanochemical technique
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02322A
_journal_year                    2022
_chemical_formula_moiety         'C17 H17 N2 O P Se'
_chemical_formula_sum            'C17 H17 N2 O P Se'
_chemical_formula_weight         375.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-12 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9392(3)
_cell_length_b                   8.0482(3)
_cell_length_c                   37.8833(12)
_cell_measurement_reflns_used    8045
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      24.3330
_cell_measurement_theta_min      2.1390
_cell_volume                     3335.28(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f     67.17 201.67   0.50    2.00  13.96 -12.24 -31.50    --   269
  2  \f   -121.38  29.12   0.50    2.00  78.62 -12.24  31.50    --   301
  3  \w   -110.52  18.48   0.50    2.00    --  -12.24 -59.25  20.08  258
  4  \w   -110.52  18.48   0.50    2.00    --  -12.24 -59.25  71.08  258
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            55566
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.660
_diffrn_reflns_theta_min         2.150
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         5557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0564P)^2^+1.2104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3181
_reflns_number_total             5557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02322a2.cif
_cod_data_source_block           comp_4
_cod_database_code               7711332
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.796
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C12(H12), C3(H3), C6(H6), C15(H15), C13(H13), C14(H14),
 C9(H9), C8(H8), C7(H7), C2(H2)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              28224
_shelx_hkl_checksum              42951
_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
;