Iodine-catalyzed three-component annulation: Access to highly fluorescent trisubstituted thiophenes
Rajkumar, Deepan Babu; Gnanaoli, Karthiyayini; Puhazhendhi, Arulmozhi; Arunachalam, Tamilselvi; Subbiah, Nagarajan; Sridharan, Vellaisamy; Sivalingam, Soumya; Maheswari, Uma C.; Chemical Communications  (2023) –; doi:10.1039/D3CC02711B

data_7131911
_publ_section_title
;
 Iodine-catalyzed three-component annulation: Access to highly fluorescent
 trisubstituted thiophenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02711B
_journal_year                    2023
_chemical_formula_moiety         'C17 H16 O6 S'
_chemical_formula_sum            'C17 H16 O6 S'
_chemical_formula_weight         348.36
_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             2023-01-02
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.534(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7764(2)
_cell_length_b                   24.8373(6)
_cell_length_c                   9.1903(3)
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    296.9
_cell_measurement_theta_max      26.3380
_cell_measurement_theta_min      2.5440
_cell_volume                     1627.41(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.9
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_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    -41.00  52.00   0.50    3.20    --  -14.97  30.00  30.00  186
  2  \w     41.00  80.00   0.50    3.20    --   16.22  45.00 -30.00   78
  3  \w     -3.00  22.00   0.50    3.20    --   16.22  45.00 -30.00   50
  4  \w     -8.00  86.00   0.50    3.20    --   16.22  45.00 -90.00  188
  5  \w     17.00  79.00   0.50    3.20    --   16.22-138.00-177.00  124
  6  \w    -37.00  22.00   0.50    3.20    --  -14.97 -94.00 -60.00  118
  7  \w     13.00  74.00   0.50    3.20    --   16.22-131.00  -2.00  122
  8  \w     11.00  70.00   0.50    3.20    --   16.22-125.00  90.00  118
  9  \w     14.00  40.00   0.50    3.20    --   16.22 -30.00 120.00   52
 10  \w    -47.00   7.00   0.50    3.20    --   16.22 -30.00 120.00  108
 11  \w    -56.00  41.00   0.50    3.20    --   16.22 -30.00  30.00  194
 12  \w    -37.00  22.00   0.50    3.20    --  -14.97 -94.00   0.00  118
 13  \w    -47.00 -10.00   0.50    3.20    --  -14.97 125.00  90.00   74
 14  \w    -73.00 -13.00   0.50    3.20    --  -14.97 131.00  68.00  120
 15  \w    -78.00 -17.00   0.50    3.20    --  -14.97 138.00-116.00  122
 16  \w    -68.00 -37.00   0.50    3.20    --  -14.97 125.00-180.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, 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      0.0213155000
_diffrn_orient_matrix_UB_12      0.0239518000
_diffrn_orient_matrix_UB_13      0.0458531000
_diffrn_orient_matrix_UB_21      -0.0370669000
_diffrn_orient_matrix_UB_22      0.0155400000
_diffrn_orient_matrix_UB_23      -0.0705505000
_diffrn_orient_matrix_UB_31      -0.0898117000
_diffrn_orient_matrix_UB_32      -0.0007262000
_diffrn_orient_matrix_UB_33      0.0027673000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19686
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.955
_diffrn_reflns_theta_min         2.553
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0610P)^2^+0.5660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2612
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02711b2.cif
_cod_data_source_block           exter168
_cod_database_code               7131911
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O S'
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.949
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C1(H1A,H1B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4), C6(H6), C3(H3)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              50235
_shelx_hkl_checksum              44098
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.452