<i>Exo-trig</i> selenocyclization of secondary allylic carboxamides using Woollins' reagent: <i>en route</i> to 2,5-disubstituted selenazolines.
Makhal, Priyanka N.; Dannarm, Srinivas Reddy; Shaikh, Arbaz Sujat; Ahmed, Rezwan; Chilvery, Shrilekha; Dayare, Lahu N.; Sonti, Rajesh; Godugu, Chandraiah; Kaki, Venkata Rao; Chemical communications (Cambridge, England) 59 (2023) 3767–3770; doi:10.1039/d2cc06782j

data_7131361
_publ_section_title
;
 <i>Exo-trig</i> selenocyclization of secondary allylic carboxamides using
 Woollins' reagent: <i>en route</i> to 2,5-disubstituted selenazolines.
;
_journal_issue                   25
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3767
_journal_page_last               3770
_journal_paper_doi               10.1039/d2cc06782j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C12 H12 N2 Se'
_chemical_formula_sum            'C12 H12 N2 Se'
_chemical_formula_weight         263.20
_chemical_name_systematic
2-(1H-indol-2-yl)-5-methyl-4,5-dihydro-1,3-selenazole
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-02
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-11-08 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.625(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.9055(7)
_cell_length_b                   11.0509(5)
_cell_length_c                   14.9065(7)
_cell_measurement_reflns_used    8487
_cell_measurement_temperature    299.38(17)
_cell_measurement_theta_max      26.2900
_cell_measurement_theta_min      2.2040
_cell_volume                     2375.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      299.38(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_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    -27.00   8.00   0.50   10.00    --  -14.97 -29.00  17.00   70
  2  \w    -36.00  10.00   0.50   10.00    --  -14.97 -94.00   0.00   92
  3  \w    -58.00  42.00   0.50   10.00    --   16.22 -29.00  17.00  200
  4  \w    -37.00  20.00   0.50   10.00    --  -14.97 -94.00 120.00  114
  5  \w    -41.00  59.00   0.50   10.00    --  -14.97  29.00 179.00  200
  6  \w    -69.00 -43.00   0.50   10.00    --  -14.97 -29.00  17.00   52
  7  \w    -85.00  10.00   0.50   10.00    --  -14.97 -45.00   0.00  190
  8  \w    -66.00 -10.00   0.50   10.00    --  -14.97 125.00   0.00  112
  9  \w    -56.00 -30.00   0.50   10.00    --  -14.97 125.00  30.00   52
 10  \w    -66.00 -12.00   0.50   10.00    --  -14.97 125.00 120.00  108
 11  \w    -10.00  90.00   0.50   10.00    --   16.22  29.00 179.00  200
 12  \w    -63.00 -11.00   0.50   10.00    --  -14.97 125.00 -60.00  104
 13  \w    -58.00 -17.00   0.50   10.00    --  -14.97 125.00-120.00   82
 14  \w     -7.00  50.00   0.50   10.00    --   16.22  45.00-150.00  114
 15  \w     58.00  84.00   0.50   10.00    --   16.22  45.00-150.00   52
 16  \w     45.00  85.00   0.50   10.00    --   16.22  45.00-180.00   80
 17  \w    -84.00 -51.00   0.50   10.00    --  -14.97 -61.00-150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, 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      0.0176504000
_diffrn_orient_matrix_UB_12      -0.0039186000
_diffrn_orient_matrix_UB_13      -0.0398408000
_diffrn_orient_matrix_UB_21      0.0420625000
_diffrn_orient_matrix_UB_22      0.0270684000
_diffrn_orient_matrix_UB_23      0.0249499000
_diffrn_orient_matrix_UB_31      0.0183809000
_diffrn_orient_matrix_UB_32      -0.0580997000
_diffrn_orient_matrix_UB_33      0.0143625000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1817
_diffrn_reflns_av_unetI/netI     0.1238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.970
_diffrn_reflns_theta_min         2.235
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane, pentane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.787
_refine_diff_density_min         -1.320
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.2186
_refine_ls_R_factor_gt           0.1466
_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^)+(0.1399P)^2^+55.2164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3745
_refine_ls_wR_factor_ref         0.4123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2621
_reflns_number_total             4984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06782j2.cif
_cod_data_source_block           exter107
_cod_depositor_comments          'Adding full bibliography for 7131361.cif.'
_cod_database_code               7131361
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N Se'
_shelx_estimated_absorpt_t_max   0.745
_shelx_estimated_absorpt_t_min   0.573
_reflns_odcompleteness_completeness 99.57
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00H(H00H), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B), C00O(H00K,H00O)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J),
 C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S)
2.d Idealised Me refined as rotating group:
 C00T(H00T,H00U,H00V), C00U(H00C,H00D,H00E)
;
_shelx_res_checksum              50038
_shelx_hkl_checksum              31566
_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 4.717
_oxdiff_exptl_absorpt_empirical_full_min 0.383