#------------------------------------------------------------------------------
#$Date: 2023-07-21 00:57:03 +0300 (Fri, 21 Jul 2023) $
#$Revision: 285298 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/19/7131911.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131911
loop_
_publ_author_name
'Rajkumar, Deepan Babu'
'Gnanaoli, Karthiyayini'
'Puhazhendhi, Arulmozhi'
'Arunachalam, Tamilselvi'
'Subbiah, Nagarajan'
'Sridharan, Vellaisamy'
'Sivalingam, Soumya'
'Maheswari, Uma C.'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  52.00   0.50    3.20    --  -14.97  30.00  30.00  186
  2  ω     41.00  80.00   0.50    3.20    --   16.22  45.00 -30.00   78
  3  ω     -3.00  22.00   0.50    3.20    --   16.22  45.00 -30.00   50
  4  ω     -8.00  86.00   0.50    3.20    --   16.22  45.00 -90.00  188
  5  ω     17.00  79.00   0.50    3.20    --   16.22-138.00-177.00  124
  6  ω    -37.00  22.00   0.50    3.20    --  -14.97 -94.00 -60.00  118
  7  ω     13.00  74.00   0.50    3.20    --   16.22-131.00  -2.00  122
  8  ω     11.00  70.00   0.50    3.20    --   16.22-125.00  90.00  118
  9  ω     14.00  40.00   0.50    3.20    --   16.22 -30.00 120.00   52
 10  ω    -47.00   7.00   0.50    3.20    --   16.22 -30.00 120.00  108
 11  ω    -56.00  41.00   0.50    3.20    --   16.22 -30.00  30.00  194
 12  ω    -37.00  22.00   0.50    3.20    --  -14.97 -94.00   0.00  118
 13  ω    -47.00 -10.00   0.50    3.20    --  -14.97 125.00  90.00   74
 14  ω    -73.00 -13.00   0.50    3.20    --  -14.97 131.00  68.00  120
 15  ω    -78.00 -17.00   0.50    3.20    --  -14.97 138.00-116.00  122
 16  ω    -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       'ω 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/[σ²(Fo²)+(0.0610P)²+0.5660P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68578(7) 0.57567(2) 0.61809(7) 0.0524(2) Uani 1 1 d . . . . .
O5 O 0.3787(2) 0.73212(6) 0.38107(17) 0.0498(4) Uani 1 1 d . . . . .
O6 O 0.2159(2) 0.67356(7) 0.1921(2) 0.0637(5) Uani 1 1 d . . . . .
O2 O 0.2535(3) 0.40981(7) 0.9353(2) 0.0706(5) Uani 1 1 d . . . . .
O1 O 0.0371(2) 0.47597(8) 0.8082(2) 0.0775(6) Uani 1 1 d . . . . .
O3 O 0.6921(3) 0.68886(8) 0.3279(3) 0.0800(6) Uani 1 1 d . . . . .
O4 O 0.9300(2) 0.64155(9) 0.5034(3) 0.0868(6) Uani 1 1 d . . . . .
C15 C 0.3327(3) 0.68297(8) 0.3220(2) 0.0416(5) Uani 1 1 d . . . . .
C5 C 0.4126(3) 0.52522(8) 0.6935(2) 0.0426(5) Uani 1 1 d . . . . .
C10 C 0.4350(3) 0.64025(8) 0.4382(2) 0.0413(5) Uani 1 1 d . . . . .
C8 C 0.4598(3) 0.56755(8) 0.6041(2) 0.0417(5) Uani 1 1 d . . . . .
C9 C 0.3422(3) 0.60492(8) 0.5028(2) 0.0424(5) Uani 1 1 d . . . . .
H9 H 0.214382 0.606726 0.479172 0.051 Uiso 1 1 calc R . . . .
C11 C 0.6229(3) 0.62900(9) 0.4893(3) 0.0465(5) Uani 1 1 d . . . . .
C4 C 0.5415(3) 0.48511(9) 0.7719(3) 0.0496(5) Uani 1 1 d . . . . .
H4 H 0.658881 0.485673 0.767446 0.060 Uiso 1 1 calc R . . . .
C7 C 0.1984(3) 0.48454(9) 0.7843(3) 0.0506(5) Uani 1 1 d . . . . .
C6 C 0.2348(3) 0.52480(9) 0.6997(3) 0.0496(5) Uani 1 1 d . . . . .
H6 H 0.145584 0.550934 0.648157 0.059 Uiso 1 1 calc R . . . .
C2 C 0.3274(3) 0.44525(9) 0.8613(3) 0.0511(5) Uani 1 1 d . . . . .
C16 C 0.2953(3) 0.77643(9) 0.2711(3) 0.0539(6) Uani 1 1 d . . . . .
H16A H 0.160355 0.771928 0.219686 0.065 Uiso 1 1 calc R . . . .
H16B H 0.345556 0.777367 0.190086 0.065 Uiso 1 1 calc R . . . .
C3 C 0.5007(3) 0.44426(9) 0.8564(3) 0.0557(6) Uani 1 1 d . . . . .
H3 H 0.587402 0.417465 0.907412 0.067 Uiso 1 1 calc R . . . .
C12 C 0.7662(3) 0.65350(10) 0.4438(3) 0.0561(6) Uani 1 1 d . . . . .
C1 C 0.0747(4) 0.43122(11) 0.9120(4) 0.0683(7) Uani 1 1 d . . . . .
H1A H -0.021215 0.403950 0.866504 0.082 Uiso 1 1 calc R . . . .
H1B H 0.074012 0.442383 1.012878 0.082 Uiso 1 1 calc R . . . .
C17 C 0.3419(5) 0.82708(10) 0.3650(3) 0.0750(8) Uani 1 1 d . . . . .
H17A H 0.288585 0.857126 0.295930 0.112 Uiso 1 1 calc GR . . . .
H17B H 0.475612 0.831160 0.414989 0.112 Uiso 1 1 calc GR . . . .
H17C H 0.291448 0.825677 0.444777 0.112 Uiso 1 1 calc GR . . . .
C13 C 0.8174(5) 0.71939(15) 0.2760(5) 0.1079(13) Uani 1 1 d . . . . .
H13A H 0.942262 0.703974 0.322772 0.129 Uiso 1 1 calc R . . . .
H13B H 0.773838 0.716851 0.161561 0.129 Uiso 1 1 calc R . . . .
C14 C 0.8251(6) 0.77338(16) 0.3198(6) 0.1198(14) Uani 1 1 d . . . . .
H14A H 0.883472 0.794006 0.263678 0.180 Uiso 1 1 calc GR . . . .
H14B H 0.896919 0.776750 0.431970 0.180 Uiso 1 1 calc GR . . . .
H14C H 0.700276 0.786544 0.293940 0.180 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 S1 C8 92.16(10) . . ?
C15 O5 C16 116.01(16) . . ?
C2 O2 C1 105.27(18) . . ?
C7 O1 C1 105.82(19) . . ?
C12 O3 C13 118.4(2) . . ?
O5 C15 C10 112.52(17) . . ?
O6 C15 O5 124.1(2) . . ?
O6 C15 C10 123.4(2) . . ?
C4 C5 C8 120.88(19) . . ?
C4 C5 C6 119.30(19) . . ?
C6 C5 C8 119.82(18) . . ?
C9 C10 C15 121.90(17) . . ?
C11 C10 C15 125.54(18) . . ?
C11 C10 C9 112.51(19) . . ?
C5 C8 S1 121.17(15) . . ?
C9 C8 S1 110.78(15) . . ?
C9 C8 C5 128.05(18) . . ?
C10 C9 H9 123.4 . . ?
C8 C9 C10 113.10(18) . . ?
C8 C9 H9 123.4 . . ?
C10 C11 S1 111.45(16) . . ?
C10 C11 C12 130.0(2) . . ?
C12 C11 S1 118.51(16) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 C5 122.3(2) . . ?
C3 C4 H4 118.9 . . ?
O1 C7 C2 109.44(19) . . ?
C6 C7 O1 128.0(2) . . ?
C6 C7 C2 122.6(2) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 C5 117.4(2) . . ?
C7 C6 H6 121.3 . . ?
O2 C2 C7 110.3(2) . . ?
C3 C2 O2 128.2(2) . . ?
C3 C2 C7 121.5(2) . . ?
O5 C16 H16A 110.2 . . ?
O5 C16 H16B 110.2 . . ?
O5 C16 C17 107.38(19) . . ?
H16A C16 H16B 108.5 . . ?
C17 C16 H16A 110.2 . . ?
C17 C16 H16B 110.2 . . ?
C4 C3 H3 121.5 . . ?
C2 C3 C4 117.0(2) . . ?
C2 C3 H3 121.5 . . ?
O3 C12 C11 111.62(19) . . ?
O4 C12 O3 124.9(2) . . ?
O4 C12 C11 123.5(2) . . ?
O2 C1 H1A 109.9 . . ?
O2 C1 H1B 109.9 . . ?
O1 C1 O2 108.7(2) . . ?
O1 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C13 H13A 109.4 . . ?
O3 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 O3 111.3(3) . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.722(2) . ?
S1 C11 1.712(2) . ?
O5 C15 1.326(2) . ?
O5 C16 1.459(3) . ?
O6 C15 1.200(2) . ?
O2 C2 1.371(3) . ?
O2 C1 1.423(3) . ?
O1 C7 1.374(3) . ?
O1 C1 1.417(3) . ?
O3 C12 1.322(3) . ?
O3 C13 1.457(3) . ?
O4 C12 1.205(3) . ?
C15 C10 1.490(3) . ?
C5 C8 1.468(3) . ?
C5 C4 1.392(3) . ?
C5 C6 1.407(3) . ?
C10 C9 1.409(3) . ?
C10 C11 1.373(3) . ?
C8 C9 1.373(3) . ?
C9 H9 0.9300 . ?
C11 C12 1.470(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.390(3) . ?
C7 C6 1.364(3) . ?
C7 C2 1.376(3) . ?
C6 H6 0.9300 . ?
C2 C3 1.366(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.486(3) . ?
C3 H3 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.394(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
