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_7160152
_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         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_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     dual
_audit_creation_date             2022-02-08
_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                90
_cell_angle_beta                 97.120(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8190(2)
_cell_length_b                   13.9258(2)
_cell_length_c                   10.6950(2)
_cell_measurement_reflns_used    4292
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      78.3470
_cell_measurement_theta_min      4.5580
_cell_volume                     1451.13(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.967
_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    -32.00  55.00   0.50    1.40    --    0.00  82.00-120.00  174
  2  \w    -13.00  37.00   0.50    1.40    --    0.00  37.00-120.00  100
  3  \w    -27.00  16.00   0.50    1.40    --    0.00 -19.00 -30.00   86
  4  \w     23.00 119.00   0.50    5.60    --  107.20 -61.00  30.00  192
  5  \w     18.00  57.00   0.50    5.60    --  107.20 -45.00  60.00   78
  6  \w     87.00 127.00   0.50    5.60    --  107.20 -45.00  60.00   80
  7  \w     19.00  86.00   0.50    5.60    --  107.20 -45.00-150.00  134
  8  \w     56.00 140.00   0.50    5.60    --  107.20 -82.00  30.00  168
  9  \w     22.00  48.00   0.50    5.60    --  107.20 -82.00  30.00   52
 10  \w     89.00 193.00   0.50    5.60    --  107.20  45.00-180.00  208
 11  \w     90.00 119.00   0.50    5.60    --  107.20 -45.00-150.00   58
 12  \w     18.00  58.00   0.50    5.60    --  107.20 -30.00  90.00   80
 13  \w     83.00 108.00   0.50    5.60    --  107.20 -30.00  90.00   50
 14  \w     72.00 110.00   0.50    5.60    --  107.20 -15.00-180.00   76
 15  \w     22.00  59.00   0.50    5.60    --  107.20 -15.00-180.00   74
;
_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      0.1541018000
_diffrn_orient_matrix_UB_12      0.0188379000
_diffrn_orient_matrix_UB_13      -0.0031299000
_diffrn_orient_matrix_UB_21      0.0201876000
_diffrn_orient_matrix_UB_22      -0.1056774000
_diffrn_orient_matrix_UB_23      -0.0362014000
_diffrn_orient_matrix_UB_31      -0.0288190000
_diffrn_orient_matrix_UB_32      0.0268903000
_diffrn_orient_matrix_UB_33      -0.1405362000
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8389
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.467
_diffrn_reflns_theta_min         4.538
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69429
_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    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0424P)^2^+0.5572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2649
_reflns_number_total             3060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01168f2.cif
_cod_data_source_block           exp_1005_ak_vns-1499(a)
_cod_depositor_comments
'Adding full bibliography for 7160152--7160154.cif.'
_cod_database_code               7160152
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H15 N O2'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C10(H10), C16(H16), C5(H5), C17(H17), C14(H14), C2(H2),
 C4(H4), C3(H3), C13(H13), C11(H11)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              85092
_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 2.101
_oxdiff_exptl_absorpt_empirical_full_min 0.675