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_7160154
_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         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_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             2022-02-09
_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                63.066(4)
_cell_angle_beta                 84.657(3)
_cell_angle_gamma                84.039(3)
_cell_formula_units_Z            4
_cell_length_a                   10.1660(3)
_cell_length_b                   11.6979(5)
_cell_length_c                   12.1456(5)
_cell_measurement_reflns_used    4723
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      78.9790
_cell_measurement_theta_min      4.2800
_cell_volume                     1279.00(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 0.983
_diffrn_measured_fraction_theta_max 0.944
_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    -52.00  19.00   0.50    0.62    --    0.00 -37.00  30.00  142
  2  \w    -37.00 -12.00   0.50    0.62    --    0.00 -82.00 -60.00   50
  3  \w    -33.00  19.00   0.50    0.62    --    0.00 -77.00-120.00  104
  4  \w    -82.00 -43.00   0.50    0.62    --    0.00 -77.00-120.00   78
  5  \w    -28.00  66.00   0.50    0.62    --    0.00  77.00 -90.00  188
  6  \w    141.00 172.00   0.50    2.46    --  107.20  15.00 -60.00   62
  7  \w     80.00 138.00   0.50    2.46    --  107.20  15.00 -60.00  116
  8  \w     23.00 126.00   0.50    2.46    --  107.20 -45.00   0.00  206
  9  \w     84.00 110.00   0.50    2.46    --  107.20 -82.00 -60.00   52
 10  \w     55.00  81.00   0.50    2.46    --  107.20 -82.00 -60.00   52
 11  \w     18.00  45.00   0.50    2.46    --  107.20 -77.00 120.00   54
 12  \w     50.00 137.00   0.50    2.46    --  107.20 -77.00 120.00  174
 13  \w     19.00  59.00   0.50    2.46    --  107.20 -30.00 150.00   80
 14  \w     64.00 120.00   0.50    2.46    --  107.20 -30.00 150.00  112
 15  \w     19.00 137.00   0.50    2.46    --  107.20 -82.00-120.00  236
 16  \w     86.00 196.00   0.50    2.46    --  107.20  15.00-180.00  220
 17  \w     36.00 110.00   0.50    2.46    --  107.20 -82.00-180.00  148
 18  \w     29.00  94.00   0.50    2.46    --  107.20 -45.00 -90.00  130
 19  \w     43.00 133.00   0.50    2.46    --  107.20 -82.00  30.00  180
 20  \w    148.00 173.00   0.50    2.46    --  107.20  82.00 -30.00   50
 21  \w     84.00 115.00   0.50    2.46    --  107.20  82.00 -30.00   62
;
_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      0.0185538000
_diffrn_orient_matrix_UB_12      -0.1199708000
_diffrn_orient_matrix_UB_13      0.1247784000
_diffrn_orient_matrix_UB_21      -0.0073724000
_diffrn_orient_matrix_UB_22      -0.0867979000
_diffrn_orient_matrix_UB_23      -0.0636979000
_diffrn_orient_matrix_UB_31      0.1512591000
_diffrn_orient_matrix_UB_32      0.0001094000
_diffrn_orient_matrix_UB_33      -0.0258777000
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.944
_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       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11900
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.748
_diffrn_reflns_theta_min         4.088
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85041
_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    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0498P)^2^+0.1677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4156
_reflns_number_total             5258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01168f2.cif
_cod_data_source_block           exp_1006_ak-ns-1491(mf)-1_autored
_cod_depositor_comments
'Adding full bibliography for 7160152--7160154.cif.'
_cod_original_cell_volume        1279.00(9)
_cod_database_code               7160154
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H12 N2 O'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.891
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C114(H114), C14(H14), C5(H5), C105(H105), C16(H16), C115(H115), C102(H102),
 C116(H116), C15(H15), C9(H9), C113(H113), C109(H109), C2(H2), C3(H3), C4(H4),
 C104(H104), C103(H103), C13(H13), C110(H110), C112(H112), C10(H10), C111(H111),
  C11(H11), C12(H12)
;
_shelx_res_checksum              33111
_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 1.864
_oxdiff_exptl_absorpt_empirical_full_min 0.678