2-Pyridyl Sulfoxide Directed Pd(II)-Catalyzed Regioselective C2- Arylation/Alkenylation of Indoles
Yadav, Kanchan; Jat, Ram Singh; Singh, Ritesh; Goswami, Bhupendra; Bhanuchandra, M.; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00484A

data_7161115
_publ_section_title
;
 2-Pyridyl sulfoxide-directed Pd(II)-catalyzed regioselective
 C2-arylation/alkenylation of indoles.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3935
_journal_page_last               3940
_journal_paper_doi               10.1039/d6ob00484a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         '0.143(C24 H20 N2 O3 S)'
_chemical_formula_sum            'C3.429 H2.857 N0.286 O0.429 S0.143'
_chemical_formula_weight         59.645
_chemical_name_systematic        'Indole C2 olefination'
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-11-26
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-11-28 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                96.178(3)
_cell_angle_beta                 116.703(4)
_cell_angle_gamma                111.389(4)
_cell_formula_units_Z            14
_cell_length_a                   10.4219(5)
_cell_length_b                   10.5863(5)
_cell_length_c                   11.5849(5)
_cell_measurement_reflns_used    8419
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.9400
_cell_measurement_theta_min      2.0760
_cell_volume                     1004.97(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.108a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.108a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.108a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9990
_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     -4.00  78.00   0.50   10.00    --    6.28  18.00  23.00  164
  2  \w    -68.00   4.00   0.50   10.00    --    6.28 -18.00-144.00  144
  3  \w    -23.00   2.00   0.50   10.00    --   -3.86 -99.00-180.00   50
  4  \w    -23.00  29.00   0.50   10.00    --   -3.86 -99.00  30.00  104
  5  \w    -19.00  69.00   0.50   10.00    --   -3.86  57.00-180.00  176
  6  \w    -59.00 -12.00   0.50   10.00    --    6.28 -19.00  60.00   94
  7  \w      3.00  34.00   0.50   10.00    --    6.28 -99.00-180.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0142829000
_diffrn_orient_matrix_UB_12      -0.0598584000
_diffrn_orient_matrix_UB_13      0.0087736000
_diffrn_orient_matrix_UB_21      -0.0801631000
_diffrn_orient_matrix_UB_22      -0.0401755000
_diffrn_orient_matrix_UB_23      -0.0150694000
_diffrn_orient_matrix_UB_31      -0.0278510000
_diffrn_orient_matrix_UB_32      -0.0244582000
_diffrn_orient_matrix_UB_33      -0.0703787000
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12692
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9990
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.08
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.108a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       irregular
_exptl_crystal_F_000             438.510
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.4944
_refine_diff_density_min         -0.3916
_refine_diff_density_rms         0.0682
_refine_ls_d_res_high            0.8003
_refine_ls_d_res_low             9.7826
_refine_ls_goodness_of_fit_ref   0.9780
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     53
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9780
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.6305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3520
_reflns_number_total             4119
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d6ob00484a2.cif
_cod_data_source_block           ky-279_auto
_cod_depositor_comments
'Adding full bibliography for 7161115--7161116.cif.'
_cod_database_code               7161115
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H N S O'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed U11: S001(0.012093) O002(0.016808) O003(0.024294) O004(0.02939)
 N005(0.01156) N006(0.02258) C007(0.014981) C008(0.015092) C009(0.015776)
 C00A(0.013603) C00B(0.016317) C00C(0.012446) C00D(0.021412) C00E(0.017621)
 C00F(0.010412) C00G(0.013204) C00H(0.017261) C00I(0.018778) C00J(0.016496)
 C00K(0.013392) C00L(0.023373) C00M(0.015204) C00N(0.0281) C00O(0.022424)
 C00P(0.019) C00Q(0.025436) C00R(0.027669) C00S(0.041117) C00T(0.058683)
 C00U(0.066435)
 Fixed U12: S001(0.002755) O002(0.004271) O003(-0.00864) O004(-0.00495)
 N005(0.002671) N006(0.00283) C007(0.001907) C008(0.004145) C009(0.003334)
 C00A(0.001859) C00B(0.001212) C00C(0.001571) C00D(0.006517) C00E(-0.000753)
 C00F(0.001298) C00G(0.001317) C00H(0.001293) C00I(0.00215) C00J(0.005603)
 C00K(0.003773) C00L(0.002706) C00M(0.004265) C00N(0.003495) C00O(0.009584)
 C00P(0.001213) C00Q(-0.002106) C00R(0.002336) C00S(0.023828) C00T(0.009235)
 C00U(0.02815)
 Fixed U13: S001(-0.001038) O002(0.002087) O003(-0.00109) O004(0.001207) N005(-
 0.000653) N006(0.003829) C007(-0.00081) C008(-0.003224) C009(-0.001208)
 C00A(0.000043) C00B(0.00031) C00C(-0.000742) C00D(0.001725) C00E(-0.0022)
 C00F(-0.001321) C00G(-0.000887) C00H(-0.001733) C00I(0.000384) C00J(0.000454)
 C00K(0.001203) C00L(-0.000441) C00M(-0.001553) C00N(0.006817) C00O(-0.003627)
 C00P(0.002873) C00Q(-0.004774) C00R(0.005668) C00S(-0.01113) C00T(0.013671)
 C00U(-0.001307)
 Fixed U22: S001(0.019443) O002(0.025575) O003(0.03119) O004(0.03103)
 N005(0.017357) N006(0.024752) C007(0.015741) C008(0.019897) C009(0.017192)
 C00A(0.019704) C00B(0.013766) C00C(0.018564) C00D(0.017061) C00E(0.017957)
 C00F(0.022535) C00G(0.017114) C00H(0.020243) C00I(0.022115) C00J(0.018908)
 C00K(0.020777) C00L(0.015382) C00M(0.031021) C00N(0.018989) C00O(0.023504)
 C00P(0.039282) C00Q(0.031142) C00R(0.032566) C00S(0.036303) C00T(0.01987)
 C00U(0.027999)
 Fixed U23: S001(-0.001446) O002(0.004649) O003(-0.009178) O004(-0.004093)
 N005(-0.002585) N006(0.003638) C007(0.001793) C008(-0.002602) C009(-0.000748)
 C00A(-0.000093) C00B(0.000528) C00C(-0.000238) C00D(-0.004603) C00E(-0.00022)
 C00F(-0.001143) C00G(0.000309) C00H(-0.001362) C00I(-0.002227) C00J(-0.001183)
 C00K(-0.003077) C00L(-0.003221) C00M(-0.007754) C00N(-0.004226) C00O(-
 0.006962) C00P(-0.002096) C00Q(-0.011956) C00R(0.008281) C00S(-0.010827) C00T(-
 0.000327) C00U(-0.002219)
 Fixed U33: S001(0.0154) O002(0.01794) O003(0.02174) O004(0.017) N005(0.01481)
 N006(0.02534) C007(0.01276) C008(0.01979) C009(0.0139) C00A(0.01617)
 C00B(0.01281) C00C(0.01512) C00D(0.0148) C00E(0.01663) C00F(0.01578)
 C00G(0.01369) C00H(0.02003) C00I(0.0146) C00J(0.01752) C00K(0.01516)
 C00L(0.01515) C00M(0.0212) C00N(0.0233) C00O(0.0239) C00P(0.01949)
 C00Q(0.02387) C00R(0.02651) C00S(0.02483) C00T(0.02552) C00U(0.01908)
 Fixed X: S001(0.65358) O002(0.667039) O003(0.280651) O004(0.391437)
 N005(0.973326) N006(0.691898) C007(0.994682) C008(0.3979) C009(0.676808)
 C00A(1.252225) C00B(1.082687) C00C(0.826592) C00D(1.098845) C00E(1.332332)
 C00F(0.693102) C00G(0.818424) C00H(0.707882) C00I(0.534651) C00J(1.080089)
 C00K(1.020562) C00L(1.247326) C00M(0.722095) C00N(1.010568) C00O(1.259581)
 C00P(0.721067) C00Q(0.143124) C00R(0.706791) C00S(1.332622) C00T(1.084705)
 C00U(1.245768)
 Fixed Y: S001(0.446721) O002(0.566998) O003(-0.09051) O004(-0.014369)
 N005(0.329998) N006(0.438708) C007(0.523081) C008(-0.002417) C009(0.183742)
 C00A(0.529781) C00B(0.461208) C00C(0.422759) C00D(0.170031) C00E(0.663417)
 C00F(0.524128) C00G(0.30662) C00H(0.660211) C00I(0.110419) C00J(0.659236)
 C00K(0.229895) C00L(0.726973) C00M(0.711606) C00N(0.083821) C00O(0.199384)
 C00P(0.625997) C00Q(-0.207957) C00R(0.491515) C00S(0.146353) C00T(0.031776)
 C00U(0.064467)
 Fixed Z: S001(0.554288) O002(0.495278) O003(0.277121) O004(0.154603)
 N005(0.565275) N006(0.796417) C007(0.693492) C008(0.262072) C009(0.406883)
 C00A(0.739086) C00B(0.668531) C00C(0.601592) C00D(0.626653) C00E(0.835672)
 C00F(0.721007) C00G(0.524741) C00H(0.754489) C00I(0.393639) C00J(0.792608)
 C00K(0.517659) C00L(0.862991) C00M(0.877246) C00N(0.67494) C00O(0.679608)
 C00P(0.958544) C00Q(0.1547) C00R(0.915441) C00S(0.781666) C00T(0.777378)
 C00U(0.831394)
3.a Idealised Me refined as rotating group:
 C00Q(H00d,H00f,H00g)
;
_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 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.892