#------------------------------------------------------------------------------
#$Date: 2024-10-06 11:52:05 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/92/7249253.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_7249253
loop_
_publ_author_name
'Qin, Shengxiang'
'Zhang, Yaqi'
'Jiang, Long'
'Tse, Man Kin'
'Chan, Albert S. C.'
'Qiu, Liqin'
_publ_section_title
;
 Acid-catalyzed regioselective remote heteroarylation of alkenes via
 CC bond migration
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              10299
_journal_page_last               10307
_journal_paper_doi               10.1039/D4GC03356F
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C17 H14 S'
_chemical_formula_sum            'C17 H14 S'
_chemical_formula_weight         250.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-15 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                105.060(9)
_cell_angle_beta                 106.146(9)
_cell_angle_gamma                103.841(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2038(9)
_cell_length_b                   8.2643(9)
_cell_length_c                   10.5638(10)
_cell_measurement_reflns_used    1608
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.4410
_cell_measurement_theta_min      4.6180
_cell_volume                     625.76(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -16.00   1.00    1.00    --  -40.77 -57.00 120.00   94
  2  ω    -63.00  28.00   1.00    1.00    --  -40.77  57.00 -90.00   91
  3  ω     57.00  99.00   1.00    1.00    --   40.77-133.00  90.00   42
  4  ω    -32.00  63.00   1.00    1.00    --   40.77 -38.00 -30.00   95
  5  ω     89.00 170.00   1.00    1.02    --  105.29  45.00  30.00   81
  6  ω     27.00  97.00   1.00    1.02    --  105.29 -94.00  60.00   70
  7  ω     36.00  91.00   1.00    1.02    --  105.29 -45.00  30.00   55
  8  ω     38.00  81.00   1.00    1.02    --  105.29-125.00   0.00   43
  9  ω     77.00 123.00   1.00    1.02    --  105.29  30.00-150.00   46
 10  ω     82.00 112.00   1.00    1.02    --  105.29-125.00   0.00   30
 11  ω     29.00  71.00   1.00    1.02    --  105.29 -94.00-180.00   42
 12  ω     83.00 109.00   1.00    1.02    --  105.29-125.00 -90.00   26
 13  ω     42.00 112.00   1.00    1.02    --  105.29-125.00-180.00   70
 14  ω     82.00 177.00   1.00    1.02    --  105.29  30.00 -60.00   95
 15  ω     35.00 124.00   1.00    1.02    --  105.29 -61.00-180.00   89
 16  ω    126.00 153.00   1.00    1.02    --  105.29  77.00-150.00   27
 17  ω     97.00 166.00   1.00    1.02    --  105.29 125.00 120.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0657536000
_diffrn_orient_matrix_UB_12      -0.1055590000
_diffrn_orient_matrix_UB_13      0.0921117000
_diffrn_orient_matrix_UB_21      -0.0431029000
_diffrn_orient_matrix_UB_22      -0.1589295000
_diffrn_orient_matrix_UB_23      -0.1333326000
_diffrn_orient_matrix_UB_31      0.1920804000
_diffrn_orient_matrix_UB_32      0.0748356000
_diffrn_orient_matrix_UB_33      0.0020920000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3942
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.014
_diffrn_reflns_theta_min         4.652
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (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    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0436
_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/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2101
_reflns_number_total             2387
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc03356f2.cif
_cod_data_source_block           a21060801aqlq1
_cod_depositor_comments          'Adding full bibliography for 7249253.cif.'
_cod_original_cell_volume        625.75(12)
_cod_database_code               7249253
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHS
_chemical_oxdiff_usercomment     210608
_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.
;
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_olex2_date_sample_data_collection 2021-06-08
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.721
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.3883(2) 0.6526(3) 0.3457(2) 0.0231(4) Uani 1 1 d . . . . .
C2 C 0.2788(2) 0.7522(2) 0.40275(19) 0.0233(4) Uani 1 1 d . . . . .
H2 H 0.3586 0.8588 0.4840 0.028 Uiso 1 1 calc R . . . .
C3 C 0.1714(3) 0.6132(3) 0.4529(2) 0.0255(4) Uani 1 1 d . . . . .
H3A H 0.2208 0.6494 0.5546 0.031 Uiso 1 1 calc R . . . .
H3B H 0.0457 0.6050 0.4243 0.031 Uiso 1 1 calc R . . . .
C4 C 0.1883(3) 0.4314(3) 0.3845(2) 0.0260(4) Uani 1 1 d . . . . .
H4A H 0.2178 0.3740 0.4528 0.031 Uiso 1 1 calc R . . . .
H4B H 0.0777 0.3530 0.3073 0.031 Uiso 1 1 calc R . . . .
C5 C 0.3394(2) 0.4807(3) 0.3328(2) 0.0232(4) Uani 1 1 d . . . . .
C6 C 0.4378(2) 0.3848(3) 0.26908(19) 0.0235(4) Uani 1 1 d . . . . .
C7 C 0.5642(3) 0.4986(3) 0.2344(2) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.6745(3) 0.4367(3) 0.1696(2) 0.0290(4) Uani 1 1 d . . . . .
H8 H 0.7566 0.5124 0.1472 0.035 Uiso 1 1 calc R . . . .
C9 C 0.6586(3) 0.2592(3) 0.1395(2) 0.0316(5) Uani 1 1 d . . . . .
H9 H 0.7309 0.2152 0.0959 0.038 Uiso 1 1 calc R . . . .
C10 C 0.5356(3) 0.1438(3) 0.1734(2) 0.0301(5) Uani 1 1 d . . . . .
H10 H 0.5279 0.0251 0.1526 0.036 Uiso 1 1 calc R . . . .
C11 C 0.4257(3) 0.2063(3) 0.2377(2) 0.0268(4) Uani 1 1 d . . . . .
H11 H 0.3442 0.1297 0.2599 0.032 Uiso 1 1 calc R . . . .
C12 C 0.1530(2) 0.8029(2) 0.2963(2) 0.0225(4) Uani 1 1 d . . . . .
C13 C 0.1064(3) 0.7262(3) 0.1518(2) 0.0265(4) Uani 1 1 d . . . . .
H13 H 0.1602 0.6466 0.1172 0.032 Uiso 1 1 calc R . . . .
C14 C -0.0197(3) 0.7674(3) 0.0586(2) 0.0312(5) Uani 1 1 d . . . . .
H14 H -0.0497 0.7156 -0.0379 0.037 Uiso 1 1 calc R . . . .
C15 C -0.1008(3) 0.8855(3) 0.1092(2) 0.0322(5) Uani 1 1 d . . . . .
H15 H -0.1863 0.9120 0.0468 0.039 Uiso 1 1 calc R . . . .
C16 C -0.0545(3) 0.9642(3) 0.2531(2) 0.0296(5) Uani 1 1 d . . . . .
H16 H -0.1090 1.0433 0.2874 0.036 Uiso 1 1 calc R . . . .
C17 C 0.0734(3) 0.9246(3) 0.3456(2) 0.0255(4) Uani 1 1 d . . . . .
H17 H 0.1065 0.9801 0.4420 0.031 Uiso 1 1 calc R . . . .
S1 S 0.55782(6) 0.71589(6) 0.28197(5) 0.0282(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 '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
C2 C1 S1 131.54(14) . . ?
C5 C1 C2 114.54(17) . . ?
C5 C1 S1 113.76(16) . . ?
C1 C2 H2 109.8 . . ?
C1 C2 C3 100.75(15) . . ?
C1 C2 C12 114.77(16) . . ?
C3 C2 H2 109.8 . . ?
C12 C2 H2 109.8 . . ?
C12 C2 C3 111.60(14) . . ?
C2 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 C2 107.63(15) . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 C3 102.98(15) . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C1 C5 C4 111.61(18) . . ?
C1 C5 C6 113.66(17) . . ?
C6 C5 C4 134.68(17) . . ?
C7 C6 C5 110.61(17) . . ?
C11 C6 C5 130.64(17) . . ?
C11 C6 C7 118.75(18) . . ?
C6 C7 S1 111.56(15) . . ?
C8 C7 C6 121.75(18) . . ?
C8 C7 S1 126.69(15) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 118.01(19) . . ?
C9 C8 H8 121.0 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.5(2) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.22(19) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 120.1 . . ?
C10 C11 C6 119.77(18) . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C2 122.99(18) . . ?
C13 C12 C17 118.55(18) . . ?
C17 C12 C2 118.37(17) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.72(19) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.94(19) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.75(19) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 120.99(19) . . ?
C16 C17 H17 119.5 . . ?
C1 S1 C7 90.41(9) . . ?
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
C1 C2 1.498(3) . ?
C1 C5 1.340(3) . ?
C1 S1 1.7371(19) . ?
C2 H2 0.9800 . ?
C2 C3 1.570(2) . ?
C2 C12 1.520(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.546(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.500(3) . ?
C5 C6 1.436(3) . ?
C6 C7 1.421(3) . ?
C6 C11 1.397(3) . ?
C7 C8 1.390(3) . ?
C7 S1 1.752(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.404(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(3) . ?
C12 C17 1.393(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9300 . ?
