#------------------------------------------------------------------------------
#$Date: 2022-07-01 03:35:57 +0300 (Fri, 01 Jul 2022) $
#$Revision: 276464 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158750.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_7158750
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         'C16 H16 F3 N O2 S'
_chemical_formula_sum            'C16 H16 F3 N O2 S'
_chemical_formula_weight         343.36
_chemical_name_systematic        555
_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             2019-12-20
_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                90
_cell_angle_beta                 110.597(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9152(6)
_cell_length_b                   13.5262(4)
_cell_length_c                   10.7286(6)
_cell_measurement_reflns_used    5595
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1790
_cell_measurement_theta_min      3.9700
_cell_volume                     1618.57(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_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
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     60.00 129.00   0.50    3.28    --   40.70  32.00  60.00  138
  2  ω     34.00  65.00   0.50    3.28    --   40.70 -65.00  60.00   62
  3  ω    -19.00  52.00   0.50    3.28    --   40.70 -77.00 -30.00  142
  4  ω     16.00 130.00   0.50    3.28    --   40.70  65.00-150.00  228
  5  ω     34.00  60.00   0.50    3.28    --   40.70 -82.00-150.00   52
  6  ω     37.00  64.00   0.50    3.28    --   40.70 -82.00-180.00   54
  7  ω     35.00  63.00   0.50    3.28    --   40.70 -65.00-120.00   56
  8  ω     12.00  66.00   0.50    3.28    --   40.70 -82.00-120.00  108
  9  ω     22.00  49.00   0.50    3.28    --   40.70  77.00  60.00   54
 10  ω     -2.00  24.00   0.50    3.28    --   40.70 -82.00-180.00   52
 11  ω     55.00 129.00   0.50    3.28    --   40.70  82.00 -90.00  148
 12  ω    -22.00   4.00   0.50    3.28    --   40.70 -65.00 -60.00   52
 13  ω    -47.00   2.00   0.50    3.28    --   40.70 -82.00-150.00   98
 14  ω    -36.00  20.00   0.50    3.28    --   40.70 -82.00  30.00  112
 15  ω     13.00  46.00   0.50    3.28    --   40.70  32.00  60.00   66
 16  ω     36.00  67.00   0.50    3.28    --   40.70 -82.00  30.00   62
 17  ω     -5.00  30.00   0.50    3.28    --   40.70 -65.00-120.00   70
 18  ω    -37.00 -12.00   0.50    3.28    --   40.70 -65.00-120.00   50
 19  ω    -43.00 -18.00   0.50    3.28    --   40.70 -82.00-180.00   50
 20  ω     78.00 104.00   0.50    3.28    --   40.70  77.00  60.00   52
 21  ω     -5.00  32.00   0.50    3.28    --   40.70 -65.00  60.00   74
 22  ω     33.00  93.00   0.50    6.14    --   93.40 -82.00 -60.00  120
 23  ω      6.00  48.00   0.50    6.14    --   93.40 -25.00  90.00   84
 24  ω      5.00 171.00   0.50    6.14    --   93.40   0.00-120.00  332
 25  ω     11.00  99.00   0.50    6.14    --   93.40 -82.00 120.00  176
 26  ω      4.00  99.00   0.50    6.14    --   93.40 -82.00-120.00  190
 27  ω     59.00  97.00   0.50    6.14    --   93.40 -82.00  60.00   76
 28  ω      8.00 113.00   0.50    6.14    --   93.40 -33.00 -30.00  210
 29  ω     55.00  81.00   0.50    6.14    --   93.40 -25.00  90.00   52
 30  ω     95.00 135.00   0.50    6.14    --   93.40 -25.00  90.00   80
 31  ω     23.00 101.00   0.50    6.14    --   93.40 -82.00 150.00  156
 32  ω      6.00  46.00   0.50    6.14    --   93.40 -82.00 -90.00   80
 33  ω     93.00 130.00   0.50    6.14    --   93.40  33.00  60.00   74
 34  ω     12.00  87.00   0.50    6.14    --   93.40 -82.00-150.00  150
 35  ω     83.00 133.00   0.50    6.14    --   93.40 -33.00 150.00  100
 36  ω     66.00 107.00   0.50    6.14    --   93.40  59.00 -60.00   82
 37  ω      5.00 120.00   0.50    6.14    --   93.40 -59.00 -30.00  230
 38  ω     74.00 118.00   0.50    6.14    --   93.40 -82.00   0.00   88
 39  ω     42.00  93.00   0.50    6.14    --   93.40 -82.00  90.00  102
 40  ω    154.00 179.00   0.50    6.14    --   93.40 -25.00  90.00   50
 41  ω      4.00  79.00   0.50    6.14    --   93.40 -82.00-180.00  150
 42  ω     61.00  97.00   0.50    6.14    --   93.40 -82.00 -90.00   72
 43  ω      9.00  94.00   0.50    6.14    --   93.40 -82.00 -30.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1344479000
_diffrn_orient_matrix_UB_12      -0.0049869000
_diffrn_orient_matrix_UB_13      -0.0851819000
_diffrn_orient_matrix_UB_21      0.0136281000
_diffrn_orient_matrix_UB_22      0.0923311000
_diffrn_orient_matrix_UB_23      -0.0775523000
_diffrn_orient_matrix_UB_31      0.0287599000
_diffrn_orient_matrix_UB_32      -0.0665306000
_diffrn_orient_matrix_UB_33      -0.1013066000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12854
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.719
_diffrn_reflns_theta_min         3.963
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0479
_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)+(0.0847P)²+0.2757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2268
_reflns_number_total             2912
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01034h2.cif
_cod_data_source_block           exp_32
_cod_original_cell_volume        1618.57(14)
_cod_database_code               7158750
_shelx_shelxl_version_number     2018/3
_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   0.958
_shelx_estimated_absorpt_t_min   0.882
_diffrn_oxdiff_digest_frames
;
018c683d82c8b9dcf04e80dbc771e8d00204604e121
;
_diffrn_oxdiff_digest_hkl
;
015b95a0e602ef3cb6a497e758a84ede10db82
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00J(H00C,H00E), C00M(H00K,H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00H(H00H)
2.c Idealised Me refined as rotating group:
 C00K(H00G,H00I,H00J), C00N(H00M,H00N,H00O)
2.d Idealised tetrahedral OH refined as rotating group:
 O006(H006)
;
_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 2.046
_oxdiff_exptl_absorpt_empirical_full_min 0.557
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
S001 S 0.58458(6) 0.65205(4) 0.83436(6) 0.0621(2) Uani 1 1 d . . . . .
F002 F 0.85440(14) 0.47832(13) 0.86382(16) 0.0842(5) Uani 1 1 d . . . . .
O003 O 0.52720(15) 0.34142(10) 0.56836(16) 0.0591(4) Uani 1 1 d . . . . .
F004 F 0.92099(14) 0.54471(13) 0.72278(18) 0.0847(5) Uani 1 1 d . . . . .
F005 F 0.85954(15) 0.63660(12) 0.84855(18) 0.0890(5) Uani 1 1 d . . . . .
O006 O 0.71122(15) 0.62851(12) 0.58641(18) 0.0662(5) Uani 1 1 d . . . . .
H006 H 0.641896 0.642477 0.540967 0.099 Uiso 1 1 calc GR . . . .
N007 N 0.67865(18) 0.45599(13) 0.6107(2) 0.0569(5) Uani 1 1 d . . . . .
C008 C 0.4525(2) 0.49025(15) 0.7714(2) 0.0516(5) Uani 1 1 d . . . . .
C009 C 0.5785(2) 0.41686(15) 0.6250(2) 0.0523(5) Uani 1 1 d . . . . .
C00A C 0.5444(2) 0.48351(15) 0.7142(2) 0.0520(5) Uani 1 1 d . . . . .
C00B C 0.6182(2) 0.56258(16) 0.7409(2) 0.0564(5) Uani 1 1 d . . . . .
C00C C 0.2798(2) 0.45027(16) 0.8289(2) 0.0571(6) Uani 1 1 d . . . . .
C00D C 0.3593(2) 0.42553(16) 0.7667(2) 0.0547(5) Uani 1 1 d . . . . .
H00D H 0.351019 0.365768 0.721433 0.066 Uiso 1 1 calc R . . . .
C00E C 0.4645(2) 0.58025(15) 0.8418(2) 0.0541(5) Uani 1 1 d . . . . .
C00F C 0.2952(2) 0.53986(18) 0.8986(3) 0.0624(6) Uani 1 1 d . . . . .
H00F H 0.241845 0.556027 0.941152 0.075 Uiso 1 1 calc R . . . .
C00G C 0.7114(2) 0.55325(16) 0.6756(2) 0.0577(6) Uani 1 1 d . . . . .
C00H C 0.3863(2) 0.60478(17) 0.9064(2) 0.0606(6) Uani 1 1 d . . . . .
H00H H 0.395032 0.663580 0.953841 0.073 Uiso 1 1 calc R . . . .
C00I C 0.7342(2) 0.41146(18) 0.5217(2) 0.0613(6) Uani 1 1 d . . . . .
H00A H 0.778088 0.462143 0.494036 0.074 Uiso 1 1 calc R . . . .
H00B H 0.671508 0.387086 0.442584 0.074 Uiso 1 1 calc R . . . .
C00J C 0.8192(2) 0.32688(19) 0.5855(3) 0.0670(6) Uani 1 1 d . . . . .
H00C H 0.889266 0.353232 0.654898 0.080 Uiso 1 1 calc R . . . .
H00E H 0.779612 0.281717 0.627006 0.080 Uiso 1 1 calc R . . . .
C00K C 0.1782(2) 0.3820(2) 0.8226(3) 0.0719(7) Uani 1 1 d . . . . .
H00G H 0.142237 0.356772 0.733800 0.108 Uiso 1 1 calc GR . . . .
H00I H 0.119168 0.417742 0.846718 0.108 Uiso 1 1 calc GR . . . .
H00J H 0.208252 0.328108 0.883429 0.108 Uiso 1 1 calc GR . . . .
C00L C 0.8374(2) 0.55307(19) 0.7773(3) 0.0678(7) Uani 1 1 d . . . . .
C00M C 0.8592(3) 0.2701(2) 0.4861(4) 0.0891(9) Uani 1 1 d . . . . .
H00K H 0.903849 0.212227 0.529967 0.107 Uiso 1 1 calc R . . . .
H00L H 0.788595 0.247188 0.414224 0.107 Uiso 1 1 calc R . . . .
C00N C 0.9350(4) 0.3286(3) 0.4281(4) 0.1064(11) Uani 1 1 d . . . . .
H00M H 0.963808 0.286326 0.374061 0.160 Uiso 1 1 calc GR . . . .
H00N H 1.001849 0.356112 0.498680 0.160 Uiso 1 1 calc GR . . . .
H00O H 0.888130 0.381077 0.374351 0.160 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 0.0181 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C00B S001 C00E 89.89(11) . . ?
C009 N007 C00G 112.93(17) . . ?
C009 N007 C00I 121.78(19) . . ?
C00I N007 C00G 124.61(19) . . ?
C00D C008 C00A 131.3(2) . . ?
C00D C008 C00E 119.2(2) . . ?
C00E C008 C00A 109.55(19) . . ?
O003 C009 N007 124.6(2) . . ?
O003 C009 C00A 128.6(2) . . ?
N007 C009 C00A 106.76(18) . . ?
C008 C00A C009 138.1(2) . . ?
C00B C00A C008 113.4(2) . . ?
C00B C00A C009 108.3(2) . . ?
C00A C00B S001 114.59(18) . . ?
C00A C00B C00G 111.44(19) . . ?
C00G C00B S001 133.93(17) . . ?
C00D C00C C00F 119.0(2) . . ?
C00D C00C C00K 120.6(2) . . ?
C00F C00C C00K 120.4(2) . . ?
C00C C00D C008 120.1(2) . . ?
C008 C00E S001 112.54(16) . . ?
C00H C00E S001 126.46(17) . . ?
C00H C00E C008 121.0(2) . . ?
C00H C00F C00C 122.5(2) . . ?
O006 C00G N007 112.95(19) . . ?
O006 C00G C00B 115.63(19) . . ?
O006 C00G C00L 104.85(18) . . ?
N007 C00G C00B 100.26(17) . . ?
N007 C00G C00L 111.65(19) . . ?
C00B C00G C00L 111.7(2) . . ?
C00F C00H C00E 118.2(2) . . ?
N007 C00I C00J 113.4(2) . . ?
C00M C00J C00I 112.8(2) . . ?
F002 C00L C00G 111.7(2) . . ?
F004 C00L F002 106.7(2) . . ?
F004 C00L F005 107.3(2) . . ?
F004 C00L C00G 113.0(2) . . ?
F005 C00L F002 106.9(2) . . ?
F005 C00L C00G 110.9(2) . . ?
C00N C00M C00J 114.2(3) . . ?
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 C00B 1.707(2) . ?
S001 C00E 1.754(2) . ?
F002 C00L 1.339(3) . ?
O003 C009 1.234(3) . ?
F004 C00L 1.325(3) . ?
F005 C00L 1.337(3) . ?
O006 C00G 1.397(3) . ?
N007 C009 1.362(3) . ?
N007 C00G 1.476(3) . ?
N007 C00I 1.469(3) . ?
C008 C00A 1.434(3) . ?
C008 C00D 1.401(3) . ?
C008 C00E 1.413(3) . ?
C009 C00A 1.473(3) . ?
C00A C00B 1.350(3) . ?
C00B C00G 1.512(3) . ?
C00C C00D 1.379(3) . ?
C00C C00F 1.402(3) . ?
C00C C00K 1.505(3) . ?
C00E C00H 1.384(3) . ?
C00F C00H 1.375(4) . ?
C00G C00L 1.514(4) . ?
C00I C00J 1.522(3) . ?
C00J C00M 1.521(4) . ?
C00M C00N 1.492(5) . ?
