#------------------------------------------------------------------------------
#$Date: 2022-07-01 03:35:57 +0300 (Fri, 01 Jul 2022) $
#$Revision: 276464 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158751.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_7158751
loop_
_publ_author_name
'Deng, Qingsong'
'Gu, Jun'
'Zhang, Huan'
'Zhang, Youlai'
'Meng, Xiangtai'
_publ_section_title
;
 Sustainable access to benzothiophene derivatives bearing a
 trifluoromethyl group via a three-component domino reaction in water
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01034H
_journal_year                    2022
_chemical_formula_moiety         'C25 H23 F3 N2 O S'
_chemical_formula_sum            'C25 H23 F3 N2 O S'
_chemical_formula_weight         456.51
_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             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-03 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                87.735(8)
_cell_angle_beta                 77.519(9)
_cell_angle_gamma                65.425(9)
_cell_formula_units_Z            2
_cell_length_a                   8.9308(9)
_cell_length_b                   9.8192(9)
_cell_length_c                   14.3606(17)
_cell_measurement_reflns_used    2282
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2300
_cell_measurement_theta_min      3.4500
_cell_volume                     1116.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.852
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  34.00   1.00   26.24    --   30.00  54.00  90.00   26
  2  ω    -74.00 108.00   1.00   26.24    --   30.00  54.00-150.00  182
  3  ω    -70.00  58.00   1.00   26.24    --   30.00  54.00 -30.00  128
  4  ω    -73.00 -48.00   1.00   26.24    --   30.00  54.00  90.00   25
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0764309000
_diffrn_orient_matrix_UB_12      -0.0129325000
_diffrn_orient_matrix_UB_13      0.0135321000
_diffrn_orient_matrix_UB_21      0.0324485000
_diffrn_orient_matrix_UB_22      0.0176793000
_diffrn_orient_matrix_UB_23      -0.0461521000
_diffrn_orient_matrix_UB_31      -0.0334562000
_diffrn_orient_matrix_UB_32      0.0764839000
_diffrn_orient_matrix_UB_33      0.0159453000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_Laue_measured_fraction_full 0.852
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5196
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        24.713
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_min         2.638
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0819
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2300
_refine_ls_wR_factor_ref         0.2791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2181
_reflns_number_total             3238
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01034h2.cif
_cod_data_source_block           5
_cod_database_code               7158751
_shelx_shelxl_version_number     2017/1
_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 99.91
_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:
 C009(H00A,H00B), C00O(H00E,H00F), C00P(H00G,H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00C(H00D), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L),
 C4(H4), C0AA(H0AA)
2.c Idealised Me refined as rotating group:
 C00Q(H00M,H00N,H00O), C00R(H00P,H00Q,H00R), C00S(H00S,H00T,H00U)
;
_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 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.736
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
S001 S 0.24085(17) 0.46303(14) 0.21266(9) 0.0513(5) Uani 1 1 d . . . . .
F002 F 0.8163(5) 0.1954(4) 0.0342(2) 0.0681(9) Uani 1 1 d . . . . .
F003 F 0.6306(5) 0.1110(4) 0.0869(2) 0.0774(11) Uani 1 1 d . . . . .
O004 O 0.6534(4) 0.0939(4) 0.3820(2) 0.0484(8) Uani 1 1 d . . . . .
F005 F 0.5611(5) 0.3233(4) 0.0228(2) 0.0730(10) Uani 1 1 d . . . . .
N006 N 0.7089(5) 0.2028(4) 0.2425(3) 0.0400(9) Uani 1 1 d . . . . .
N007 N 0.7271(6) 0.6344(5) 0.1189(3) 0.0585(12) Uani 1 1 d . . . . .
C008 C 0.2652(6) 0.2867(5) 0.3579(3) 0.0391(10) Uani 1 1 d . . . . .
C009 C 0.8885(6) 0.1571(5) 0.2393(4) 0.0452(11) Uani 1 1 d . . . . .
H00A H 0.901401 0.172349 0.302932 0.054 Uiso 1 1 calc R . . . .
H00B H 0.927050 0.221896 0.197882 0.054 Uiso 1 1 calc R . . . .
C00A C 0.0392(6) 0.2703(6) 0.4765(4) 0.0514(12) Uani 1 1 d . . . . .
C00B C 0.2088(6) 0.2244(5) 0.4378(4) 0.0461(11) Uani 1 1 d . . . . .
H00C H 0.286888 0.149695 0.466214 0.055 Uiso 1 1 calc R . . . .
C00C C 0.5002(8) 0.6910(6) 0.4031(4) 0.0593(14) Uani 1 1 d . . . . .
H00D H 0.446473 0.700697 0.467155 0.071 Uiso 1 1 calc R . . . .
C00D C 0.4311(6) 0.2595(5) 0.3049(3) 0.0396(10) Uani 1 1 d . . . . .
C00E C 0.6550(6) 0.6710(5) 0.2147(4) 0.0462(11) Uani 1 1 d . . . . .
C00H C 0.6323(7) 0.7916(6) 0.2712(5) 0.0580(14) Uani 1 1 d . . . . .
H00H H 0.668069 0.864437 0.245903 0.070 Uiso 1 1 calc R . . . .
C00I C 0.4364(6) 0.3414(5) 0.2289(3) 0.0434(11) Uani 1 1 d . . . . .
C00J C -0.0752(6) 0.3853(6) 0.4347(4) 0.0531(13) Uani 1 1 d . . . . .
H00J H -0.189650 0.419193 0.462132 0.064 Uiso 1 1 calc R . . . .
C00K C 0.5232(7) 0.5703(6) 0.3479(4) 0.0506(12) Uani 1 1 d . . . . .
H00K H 0.487890 0.497597 0.373992 0.061 Uiso 1 1 calc R . . . .
C00L C 0.5555(8) 0.8006(6) 0.3657(5) 0.0671(17) Uani 1 1 d . . . . .
H00L H 0.539809 0.880043 0.405510 0.081 Uiso 1 1 calc R . . . .
C00N C 0.6159(6) 0.3122(5) 0.1789(3) 0.0432(11) Uani 1 1 d . . . . .
C00O C 1.0014(7) -0.0057(6) 0.2041(4) 0.0548(13) Uani 1 1 d . . . . .
H00E H 0.954774 -0.070560 0.239524 0.066 Uiso 1 1 calc R . . . .
H00F H 1.002836 -0.018193 0.137169 0.066 Uiso 1 1 calc R . . . .
C00P C 1.1815(7) -0.0528(7) 0.2159(4) 0.0663(16) Uani 1 1 d . . . . .
H00G H 1.178345 -0.037650 0.282714 0.080 Uiso 1 1 calc R . . . .
H00I H 1.244299 -0.159302 0.198767 0.080 Uiso 1 1 calc R . . . .
C00Q C 0.7942(11) 0.7218(9) 0.0522(5) 0.093(2) Uani 1 1 d . . . . .
H00M H 0.702724 0.810962 0.039745 0.139 Uiso 1 1 calc GR . . . .
H00N H 0.856253 0.662964 -0.006445 0.139 Uiso 1 1 calc GR . . . .
H00O H 0.867699 0.749061 0.079507 0.139 Uiso 1 1 calc GR . . . .
C00R C 1.2739(8) 0.0287(8) 0.1579(5) 0.0742(17) Uani 1 1 d . . . . .
H00P H 1.266095 0.025058 0.092446 0.111 Uiso 1 1 calc GR . . . .
H00Q H 1.390375 -0.017645 0.161807 0.111 Uiso 1 1 calc GR . . . .
H00R H 1.224952 0.131350 0.181902 0.111 Uiso 1 1 calc GR . . . .
C00S C -0.0202(7) 0.1998(7) 0.5640(4) 0.0679(16) Uani 1 1 d . . . . .
H00S H 0.070610 0.107307 0.572928 0.102 Uiso 1 1 calc GR . . . .
H00T H -0.113255 0.180206 0.555476 0.102 Uiso 1 1 calc GR . . . .
H00U H -0.055498 0.267039 0.619056 0.102 Uiso 1 1 calc GR . . . .
C1 C 0.6013(6) 0.5596(5) 0.2511(3) 0.0413(11) Uani 1 1 d . . . . .
C3 C 0.6564(7) 0.2362(6) 0.0803(4) 0.0543(13) Uani 1 1 d . . . . .
C2 C 0.1465(6) 0.4004(5) 0.3145(4) 0.0455(11) Uani 1 1 d . . . . .
C4 C -0.0274(7) 0.4504(6) 0.3556(4) 0.0585(14) Uani 1 1 d . . . . .
H4 H -0.107395 0.526366 0.328988 0.070 Uiso 1 1 calc R . . . .
C0AA C 0.7237(7) 0.5034(5) 0.0947(4) 0.0522(12) Uani 1 1 d . . . . .
H0AA H 0.767455 0.455319 0.034139 0.063 Uiso 1 1 calc R . . . .
C1AA C 0.6470(6) 0.4528(5) 0.1718(3) 0.0409(10) Uani 1 1 d . . . . .
C2AA C 0.6067(6) 0.1716(5) 0.3175(3) 0.0387(10) 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 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C00I S001 C2 89.8(2) . . ?
C009 N006 C00N 123.5(4) . . ?
C2AA N006 C009 121.5(4) . . ?
C2AA N006 C00N 113.7(4) . . ?
C00E N007 C00Q 126.3(5) . . ?
C0AA N007 C00E 109.2(4) . . ?
C0AA N007 C00Q 124.5(5) . . ?
C00B C008 C00D 132.2(4) . . ?
C00B C008 C2 119.4(4) . . ?
C2 C008 C00D 108.4(4) . . ?
N006 C009 H00A 108.6 . . ?
N006 C009 H00B 108.6 . . ?
N006 C009 C00O 114.5(4) . . ?
H00A C009 H00B 107.6 . . ?
C00O C009 H00A 108.6 . . ?
C00O C009 H00B 108.6 . . ?
C00B C00A C00J 118.3(5) . . ?
C00B C00A C00S 120.5(5) . . ?
C00J C00A C00S 121.1(5) . . ?
C008 C00B H00C 119.3 . . ?
C00A C00B C008 121.4(5) . . ?
C00A C00B H00C 119.3 . . ?
C00K C00C H00D 119.0 . . ?
C00K C00C C00L 122.0(5) . . ?
C00L C00C H00D 119.0 . . ?
C008 C00D C2AA 136.0(4) . . ?
C00I C00D C008 115.0(4) . . ?
C00I C00D C2AA 108.6(4) . . ?
N007 C00E C00H 130.2(5) . . ?
N007 C00E C1 107.7(4) . . ?
C00H C00E C1 122.1(5) . . ?
C00E C00H H00H 121.0 . . ?
C00L C00H C00E 117.9(5) . . ?
C00L C00H H00H 121.0 . . ?
C00D C00I S001 113.8(4) . . ?
C00D C00I C00N 112.1(4) . . ?
C00N C00I S001 134.0(4) . . ?
C00A C00J H00J 118.5 . . ?
C4 C00J C00A 123.0(5) . . ?
C4 C00J H00J 118.5 . . ?
C00C C00K H00K 121.0 . . ?
C00C C00K C1 118.1(5) . . ?
C1 C00K H00K 121.0 . . ?
C00C C00L H00L 119.7 . . ?
C00H C00L C00C 120.7(5) . . ?
C00H C00L H00L 119.7 . . ?
N006 C00N C00I 99.7(4) . . ?
N006 C00N C3 109.7(4) . . ?
N006 C00N C1AA 113.8(4) . . ?
C00I C00N C3 109.2(4) . . ?
C1AA C00N C00I 112.9(4) . . ?
C1AA C00N C3 111.1(4) . . ?
C009 C00O H00E 109.2 . . ?
C009 C00O H00F 109.2 . . ?
H00E C00O H00F 107.9 . . ?
C00P C00O C009 112.0(5) . . ?
C00P C00O H00E 109.2 . . ?
C00P C00O H00F 109.2 . . ?
C00O C00P H00G 108.5 . . ?
C00O C00P H00I 108.5 . . ?
H00G C00P H00I 107.5 . . ?
C00R C00P C00O 114.9(5) . . ?
C00R C00P H00G 108.5 . . ?
C00R C00P H00I 108.5 . . ?
N007 C00Q H00M 109.5 . . ?
N007 C00Q H00N 109.5 . . ?
N007 C00Q H00O 109.5 . . ?
H00M C00Q H00N 109.5 . . ?
H00M C00Q H00O 109.5 . . ?
H00N C00Q H00O 109.5 . . ?
C00P C00R H00P 109.5 . . ?
C00P C00R H00Q 109.5 . . ?
C00P C00R H00R 109.5 . . ?
H00P C00R H00Q 109.5 . . ?
H00P C00R H00R 109.5 . . ?
H00Q C00R H00R 109.5 . . ?
C00A C00S H00S 109.5 . . ?
C00A C00S H00T 109.5 . . ?
C00A C00S H00U 109.5 . . ?
H00S C00S H00T 109.5 . . ?
H00S C00S H00U 109.5 . . ?
H00T C00S H00U 109.5 . . ?
C00E C1 C1AA 106.2(4) . . ?
C00K C1 C00E 119.2(4) . . ?
C00K C1 C1AA 134.5(4) . . ?
F002 C3 F003 106.2(4) . . ?
F002 C3 F005 106.4(4) . . ?
F002 C3 C00N 113.3(4) . . ?
F003 C3 F005 106.7(4) . . ?
F003 C3 C00N 111.0(4) . . ?
F005 C3 C00N 112.8(4) . . ?
C008 C2 S001 113.0(4) . . ?
C4 C2 S001 127.7(4) . . ?
C4 C2 C008 119.3(5) . . ?
C00J C4 C2 118.6(5) . . ?
C00J C4 H4 120.7 . . ?
C2 C4 H4 120.7 . . ?
N007 C0AA H0AA 124.8 . . ?
N007 C0AA C1AA 110.3(5) . . ?
C1AA C0AA H0AA 124.8 . . ?
C1 C1AA C00N 124.5(4) . . ?
C0AA C1AA C00N 129.0(4) . . ?
C0AA C1AA C1 106.5(4) . . ?
O004 C2AA N006 125.4(4) . . ?
O004 C2AA C00D 128.7(4) . . ?
N006 C2AA C00D 105.8(4) . . ?
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
S001 C00I 1.717(5) . ?
S001 C2 1.748(5) . ?
F002 C3 1.332(6) . ?
F003 C3 1.338(6) . ?
O004 C2AA 1.209(5) . ?
F005 C3 1.335(7) . ?
N006 C009 1.466(6) . ?
N006 C00N 1.478(6) . ?
N006 C2AA 1.367(6) . ?
N007 C00E 1.377(7) . ?
N007 C00Q 1.459(7) . ?
N007 C0AA 1.360(7) . ?
C008 C00B 1.376(7) . ?
C008 C00D 1.431(6) . ?
C008 C2 1.416(6) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 C00O 1.527(7) . ?
C00A C00B 1.376(7) . ?
C00A C00J 1.390(8) . ?
C00A C00S 1.513(7) . ?
C00B H00C 0.9300 . ?
C00C H00D 0.9300 . ?
C00C C00K 1.370(7) . ?
C00C C00L 1.403(9) . ?
C00D C00I 1.334(6) . ?
C00D C2AA 1.490(6) . ?
C00E C00H 1.381(7) . ?
C00E C1 1.408(7) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.370(9) . ?
C00I C00N 1.518(7) . ?
C00J H00J 0.9300 . ?
C00J C4 1.357(8) . ?
C00K H00K 0.9300 . ?
C00K C1 1.400(7) . ?
C00L H00L 0.9300 . ?
C00N C3 1.526(7) . ?
C00N C1AA 1.513(6) . ?
C00O H00E 0.9700 . ?
C00O H00F 0.9700 . ?
C00O C00P 1.524(8) . ?
C00P H00G 0.9700 . ?
C00P H00I 0.9700 . ?
C00P C00R 1.489(8) . ?
C00Q H00M 0.9600 . ?
C00Q H00N 0.9600 . ?
C00Q H00O 0.9600 . ?
C00R H00P 0.9600 . ?
C00R H00Q 0.9600 . ?
C00R H00R 0.9600 . ?
C00S H00S 0.9600 . ?
C00S H00T 0.9600 . ?
C00S H00U 0.9600 . ?
C1 C1AA 1.449(6) . ?
C2 C4 1.412(7) . ?
C4 H4 0.9300 . ?
C0AA H0AA 0.9300 . ?
C0AA C1AA 1.362(7) . ?
