Propargyl alcohol as an acrolein equivalent: synthesis of β-(3-indolyl)acroleins and β-(imidazo[1,2-<i>a</i>]pyridin-3-yl)acroleins.
Bhawani, ?; Sonam, ?; Shinde, Vikki N.; Swami, Prakash N.; Rangan, Krishnan; Kumar, Anil; Organic & biomolecular chemistry 22 (2024) 8720–8723; doi:10.1039/d4ob01168f

data_7160153
_publ_section_title
;
 Propargyl alcohol as an acrolein equivalent: synthesis of
 &#x3b2;-(3-indolyl)acroleins and
 &#x3b2;-(imidazo[1,2-<i>a</i>]pyridin-3-yl)acroleins.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8720
_journal_page_last               8723
_journal_paper_doi               10.1039/d4ob01168f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C14 H10 N2 O S'
_chemical_formula_sum            'C14 H10 N2 O S'
_chemical_formula_weight         254.30
_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             2022-02-10
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-01 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                61.660(4)
_cell_angle_beta                 81.255(3)
_cell_angle_gamma                84.932(3)
_cell_formula_units_Z            4
_cell_length_a                   10.0711(4)
_cell_length_b                   11.4925(5)
_cell_length_c                   11.9654(5)
_cell_measurement_reflns_used    8361
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.3230
_cell_measurement_theta_min      4.4030
_cell_volume                     1204.54(10)
_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      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.961
_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    -19.00  37.00   0.50    0.50    --    0.00  37.00   0.00  112
  2  \w     44.00  89.00   0.50    0.50    --    0.00  37.00  30.00   90
  3  \w    -22.00  35.00   0.50    0.50    --    0.00  57.00-180.00  114
  4  \w    -89.00 -51.00   0.50    0.50    --    0.00 -77.00 150.00   76
  5  \w    -28.00   8.00   0.50    0.50    --    0.00 -77.00 150.00   72
  6  \w     45.00  89.00   0.50    0.50    --    0.00  37.00   0.00   88
  7  \w    -71.00  -9.00   0.50    0.50    --    0.00 -37.00  30.00  124
  8  \w     35.00 121.00   0.50    1.58    --  107.20 -15.00 -30.00  172
  9  \w     19.00 140.00   0.50    1.58    --  107.20 -82.00 120.00  242
 10  \w     19.00 138.00   0.50    1.58    --  107.20 -82.00 -30.00  238
 11  \w     21.00  63.00   0.50    1.58    --  107.20 -82.00-150.00   84
 12  \w     82.00 124.00   0.50    1.58    --  107.20 -82.00-150.00   84
 13  \w    157.00 197.00   0.50    1.58    --  107.20  15.00 -30.00   80
 14  \w     84.00 140.00   0.50    1.58    --  107.20  15.00 -30.00  112
 15  \w     21.00 127.00   0.50    1.58    --  107.20 -30.00-180.00  212
 16  \w     95.00 121.00   0.50    1.58    --  107.20 -82.00  60.00   52
 17  \w     84.00 194.00   0.50    1.58    --  107.20  15.00  30.00  220
 18  \w     25.00 130.00   0.50    1.58    --  107.20 -61.00 -30.00  210
 19  \w     21.00 109.00   0.50    1.58    --  107.20 -61.00 120.00  176
 20  \w     95.00 123.00   0.50    1.58    --  107.20  30.00-180.00   56
 21  \w    100.00 126.00   0.50    1.58    --  107.20 -82.00-120.00   52
 22  \w     21.00  56.00   0.50    1.58    --  107.20 -45.00  60.00   70
 23  \w     81.00 106.00   0.50    1.58    --  107.20 -82.00   0.00   50
 24  \w     52.00 120.00   0.50    1.58    --  107.20 -61.00-150.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0815423000
_diffrn_orient_matrix_UB_12      -0.0689128000
_diffrn_orient_matrix_UB_13      -0.0499849000
_diffrn_orient_matrix_UB_21      -0.0134697000
_diffrn_orient_matrix_UB_22      0.1318529000
_diffrn_orient_matrix_UB_23      -0.1222196000
_diffrn_orient_matrix_UB_31      0.1308852000
_diffrn_orient_matrix_UB_32      -0.0327129000
_diffrn_orient_matrix_UB_33      -0.0656192000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13008
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.712
_diffrn_reflns_theta_min         4.232
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76833
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.439
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0665
_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^)+(0.1099P)^2^+1.9582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4557
_reflns_number_total             5049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01168f2.cif
_cod_data_source_block           exp_1007_ak-vns-1506_autored
_cod_depositor_comments
'Adding full bibliography for 7160152--7160154.cif.'
_cod_database_code               7160153
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H10 N2 O S'
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.658
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C110(H110), C12(H12), C14(H14), C105(H105), C102(H102), C112(H112),
 C104(H104), C2(H2), C5(H5), C13(H13), C4(H4), C114(H114), C9(H9), C113(H113),
 C103(H103), C11(H11), C3(H3), C109(H109), C10(H10), C111(H111)
;
_shelx_res_checksum              83710
_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 2.116
_oxdiff_exptl_absorpt_empirical_full_min 0.632