Ruthenium(II)-catalyzed C-2 alkenylation of indole with olefins <i>via</i> a quinazolin-4(3<i>H</i>)-one directing group: a platform for selective fluorescent anion sensors.
Thakur, Rekha; Luxami, Vijay; Paul, Kamaldeep; Chemical communications (Cambridge, England) 61 (2025) 14374–14377; doi:10.1039/d5cc00984g

data_7135054
_publ_section_title
;
 Ruthenium(II)-catalyzed C-2 alkenylation of indole with olefins
 <i>via</i> a quinazolin-4(3<i>H</i>)-one directing group: a platform for
 selective fluorescent anion sensors.
;
_journal_issue                   75
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14374
_journal_page_last               14377
_journal_paper_doi               10.1039/d5cc00984g
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '0.5(C22 H19 N3 O3), 0.5[C2H4Cl2]'
_chemical_formula_sum            'C12 H11.5 Cl N1.5 O1.5'
_chemical_formula_weight         236.187
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2025-08-06
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
;
_audit_update_record
;
2025-08-07 deposited with the CCDC.	2025-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                111.969(8)
_cell_angle_beta                 98.763(5)
_cell_angle_gamma                94.676(6)
_cell_formula_units_Z            4
_cell_length_a                   9.0938(5)
_cell_length_b                   11.5029(12)
_cell_length_c                   12.1234(8)
_cell_measurement_reflns_used    4555
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8070
_cell_measurement_theta_min      3.4170
_cell_volume                     1149.00(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9795
_diffrn_measured_fraction_theta_max 0.9795
_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    -65.00 -39.00   0.50   10.03    --   -9.32 138.00  -0.00   52
  2  \w    -60.00 -34.00   0.50   10.03    --   -9.32 131.00-176.00   52
  3  \w     11.00  36.00   0.50   10.03    --    9.60-131.00 113.00   50
  4  \w     25.00  61.00   0.50   10.03    --    9.60-138.00 -61.00   72
  5  \w     16.00  59.00   0.50   10.03    --   -9.32  19.00 150.00   86
  6  \w    -20.00   8.00   0.50   10.03    --   -9.32  19.00  30.00   56
  7  \w     12.00  38.00   0.50   10.03    --   -9.32  19.00  30.00   52
  8  \w    -36.00  16.00   0.50   10.03    --   -9.32 -77.00 -60.00  104
  9  \w    -21.00  43.00   0.50   10.03    --   -9.32  19.00  90.00  128
 10  \w     32.00  57.00   0.50   10.03    --   -9.32  19.00   0.00   50
 11  \w    -17.00   9.00   0.50   10.03    --   -9.32  19.00   0.00   52
 12  \w    -41.00 -16.00   0.50   10.03    --   -9.32 125.00   0.00   50
 13  \w    -54.00   3.00   0.50   10.03    --    9.60 -38.00  90.00  114
 14  \w     18.00  56.00   0.50   10.03    --    9.60-125.00 150.00   76
 15  \w    -15.00  11.00   0.50   10.03    --    9.60  77.00   0.00   52
 16  \w     -9.00  32.00   0.50   10.03    --    9.60 -99.00 -60.00   82
 17  \w    -61.00  15.00   0.50   10.03    --    9.60 -19.00-150.00  152
 18  \w      7.00  32.00   0.50   10.03    --    9.60-125.00  60.00   50
 19  \w     10.00  36.00   0.50   10.03    --    9.60-125.00-150.00   52
 20  \w    -35.00  -6.00   0.50   10.03    --    9.60 124.00-162.81   58
 21  \w     -6.00  39.00   0.50   10.03    --    9.60  57.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, 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      0.0275829000
_diffrn_orient_matrix_UB_12      0.0490928000
_diffrn_orient_matrix_UB_13      0.0580724000
_diffrn_orient_matrix_UB_21      0.0135672000
_diffrn_orient_matrix_UB_22      0.0433452000
_diffrn_orient_matrix_UB_23      -0.0275965000
_diffrn_orient_matrix_UB_31      -0.0736815000
_diffrn_orient_matrix_UB_32      0.0153445000
_diffrn_orient_matrix_UB_33      0.0028626000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1150
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_Laue_measured_fraction_full 0.9795
_diffrn_reflns_Laue_measured_fraction_max 0.9795
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            15140
_diffrn_reflns_point_group_measured_fraction_full 0.9795
_diffrn_reflns_point_group_measured_fraction_max 0.9795
_diffrn_reflns_theta_full        23.5330
_diffrn_reflns_theta_max         23.53
_diffrn_reflns_theta_min         3.15
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       cube
_exptl_crystal_F_000             492.872
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.3928
_refine_diff_density_min         -0.5122
_refine_diff_density_rms         0.0852
_refine_ls_d_res_high            0.8900
_refine_ls_d_res_low             6.4608
_refine_ls_goodness_of_fit_ref   0.9930
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9930
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1548P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2078
_refine_ls_wR_factor_ref         0.2514
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1936
_reflns_number_total             3340
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc00984g2.cif
_cod_data_source_block           ex-rt4et
_cod_original_formula_sum        'C12 H11.5 Cl1 N1.5 O1.5'
_cod_database_code               7135054
_chemical_oxdiff_formula         'C H N O'
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C22(H22), C12(H12), C3(H3a), C21(H21), C19(H19), C20(H20), C9(H9),
 C11(H11), C10(H10)
1.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C1(H1a,H1b,H1c)
;
_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 3.533
_oxdiff_exptl_absorpt_empirical_full_min 0.482