#------------------------------------------------------------------------------
#$Date: 2020-06-05 11:45:47 +0200 (vie 05 de jun de 2020) $
#$Revision: 252694 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/63/7126357.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_7126357
loop_
_publ_author_name
'Huang, Guoling'
'Li, Jian'
'Ji, Xiaoliang'
'Chen, Lu'
'Liu, Qiang'
'Chen, Xiuwen'
'Huang, Yubing'
'Li, Yibiao'
_publ_section_title
;
 Access to 4-substituted isothiazoles through three-component cascade
 annulation and their application in C-H activation.
;
_journal_issue                   43
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5763
_journal_page_last               5766
_journal_paper_doi               10.1039/d0cc01100b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C18 H12 N2 S2'
_chemical_formula_sum            'C18 H12 N2 S2'
_chemical_formula_weight         320.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-17 deposited with the CCDC.	2020-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.155(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8212(6)
_cell_length_b                   5.9264(4)
_cell_length_c                   16.1736(11)
_cell_measurement_reflns_used    2158
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.7140
_cell_measurement_theta_min      2.8900
_cell_volume                     749.52(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  40.00   1.00    1.00    --   11.74 -57.00   0.00   99
  2  ω    -16.00  75.00   1.00    1.00    --   11.74  77.00 -90.00   91
  3  ω     -8.00  79.00   1.00    1.00    --   11.74  57.00 150.00   87
  4  ω     35.00  90.00   1.00    1.00    --   11.74-178.00-150.00   55
  5  ω     34.00  55.00   1.00    1.00    --   11.74-121.00-137.00   21
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0868504000
_diffrn_orient_matrix_UB_12      -0.0308004000
_diffrn_orient_matrix_UB_13      0.0048836000
_diffrn_orient_matrix_UB_21      0.0139008000
_diffrn_orient_matrix_UB_22      -0.0086471000
_diffrn_orient_matrix_UB_23      0.0433506000
_diffrn_orient_matrix_UB_31      -0.0222213000
_diffrn_orient_matrix_UB_32      0.1153158000
_diffrn_orient_matrix_UB_33      0.0045614000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3560
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.113
_diffrn_reflns_theta_min         2.519
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.420
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0352
_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)+(0.0412P)²+0.1754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                1667
_reflns_number_total             1748
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL hgl217_a.res in I2
    hgl217.res
    created by SHELXL-2018/3 at 10:29:46 on 11-Aug-2018
REM Old TITL HGL217 in I2
REM SHELXT solution in I2: R1 0.083, Rweak 0.038, Alpha 0.003
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = 0.158 ( 0.043 ) from 625 Parsons' quotients
REM Formula found by SHELXT: C9 N Cl
CELL 0.71073 7.8212 5.9264 16.1736 90 91.155 90
ZERR 2 0.0006 0.0004 0.0011 0 0.007 0
LATT -2
SYMM -X,+Y,-Z
SFAC C H N S
UNIT 36 24 4 4

L.S. 20
PLAN  20
SIZE 0.11 0.12 0.13
BOND
list 4
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\HGL217.hkl">
REM </olex2.extras>

WGHT    0.041200    0.175400
FVAR       0.78051
S1    4    0.713857    0.077629    0.557753    11.00000    0.02357    0.02310 =
         0.01616    0.00192    0.00071    0.00813
N1    3    0.757010    0.168867    0.652672    11.00000    0.02093    0.03215 =
         0.01687    0.00362   -0.00335    0.00530
C1    1    0.392048    0.566204    0.622154    11.00000    0.01544    0.01692 =
         0.01179    0.00232   -0.00051    0.00131
C7    1    0.523568    0.391335    0.608811    11.00000    0.01332    0.01831 =
         0.01476    0.00214   -0.00215   -0.00196
C6    1    0.225223    0.544816    0.591075    11.00000    0.02017    0.02583 =
         0.01548   -0.00379   -0.00482    0.00234
AFIX  43
H6    2    0.195096    0.418756    0.559787    11.00000   -1.20000
AFIX   0
C9    1    0.546932    0.259909    0.539997    11.00000    0.01649    0.01556 =
         0.01352    0.00201    0.00107   -0.00065
C2    1    0.432644    0.756278    0.670028    11.00000    0.01764    0.01951 =
         0.01373    0.00168    0.00106   -0.00238
AFIX  43
H2    2    0.542693    0.772582    0.692072    11.00000   -1.20000
AFIX   0
C4    1    0.146733    0.899172    0.652479    11.00000    0.02459    0.02494 =
         0.01840    0.00340    0.00425    0.00894
AFIX  43
H4    2    0.065828    1.011043    0.661487    11.00000   -1.20000
AFIX   0
C5    1    0.103978    0.708950    0.606239    11.00000    0.01684    0.03527 =
         0.01868   -0.00070   -0.00260    0.00607
AFIX  43
H5    2   -0.006913    0.691856    0.585340    11.00000   -1.20000
AFIX   0
C8    1    0.648909    0.330981    0.670559    11.00000    0.01899    0.02552 =
         0.01269    0.00085   -0.00306    0.00110
AFIX  43
H8    2    0.653806    0.403707    0.721505    11.00000   -1.20000
AFIX   0
C3    1    0.311100    0.920302    0.684986    11.00000    0.02843    0.01750 =
         0.01808   -0.00092    0.00564   -0.00177
AFIX  43
H3    2    0.340001    1.045396    0.717049    11.00000   -1.20000
AFIX   0
HKLF 4




REM  hgl217_a.res in I2
REM wR2 = 0.0822, GooF = S = 1.047, Restrained GooF = 1.047 for all data
REM R1 = 0.0352 for 1667 Fo > 4sig(Fo) and 0.0374 for all 1748 data
REM 100 parameters refined using 1 restraints

END  
     
WGHT      0.0401      0.1987 

REM Highest difference peak  0.268,  deepest hole -0.265,  1-sigma level  0.055
Q1    1   0.8267  0.0785  0.5366  11.00000  0.05    0.27
Q2    1   0.4632  0.5174  0.6055  11.00000  0.05    0.25
Q3    1   0.5945  0.1046  0.5648  11.00000  0.05    0.24
Q4    1   0.3322  0.5705  0.5849  11.00000  0.05    0.23
Q5    1   0.4082  0.9026  0.6575  11.00000  0.05    0.22
Q6    1   0.6585  0.2465  0.5413  11.00000  0.05    0.20
Q7    1   0.7414  0.3318  0.6340  11.00000  0.05    0.19
Q8    1   0.4551  0.0814  0.5381  11.00000  0.05    0.18
Q9    1   0.4902  0.2869  0.5845  11.00000  0.05    0.18
Q10   1   0.1402  0.8921  0.6069  11.00000  0.05    0.18
Q11   1   0.5002 -0.0751  0.5164  11.00000  0.05    0.18
Q12   1   0.4250  0.6699  0.6352  11.00000  0.05    0.18
Q13   1   0.0066  1.0851  0.6639  11.00000  0.05    0.17
Q14   1   0.2947  0.5665  0.6352  11.00000  0.05    0.17
Q15   1   0.4782  0.1253  0.5967  11.00000  0.05    0.16
Q16   1   0.3449  1.1719  0.6821  11.00000  0.05    0.16
Q17   1   0.8801  0.1084  0.6474  11.00000  0.05    0.16
Q18   1   0.4255  0.3721  0.6511  11.00000  0.05    0.16
Q19   1   0.6680  0.2012  0.6595  11.00000  0.05    0.15
Q20   1   0.7644 -0.0442  0.6609  11.00000  0.05    0.15

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0352 for 1667 Fo > 4sig(Fo) and 0.0374 for all 3560 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.27, deepest hole -0.26
  REM Mean Shift 0, Max Shift -0.001.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0374
  REM R1_gt = 0.0352
  REM wR_ref = 0.0822
  REM GOOF = 1.047
  REM Shift_max = -0.001
  REM Shift_mean = 0
  REM Reflections_all = 3560
  REM Reflections_gt = 1667
  REM Parameters = n/a
  REM Hole = -0.26
  REM Peak = 0.27
  REM Flack = 0.03(6)

  
;
_cod_data_source_file            d0cc01100b2.cif
_cod_data_source_block           hgl217
_cod_depositor_comments
'Adding full bibliography for 7126356--7126358.cif.'
_cod_database_code               7126357
_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   0.962
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C4(H4), C5(H5), C8(H8), C3(H3)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.510
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, 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 0.71386(8) 0.07763(12) 0.55775(4) 0.02094(19) Uani 1 1 d . . . . .
N1 N 0.7570(3) 0.1689(4) 0.65267(14) 0.0234(5) Uani 1 1 d . . . . .
C1 C 0.3920(3) 0.5662(5) 0.62215(13) 0.0147(5) Uani 1 1 d . . . . .
C7 C 0.5236(3) 0.3913(5) 0.60881(16) 0.0155(5) Uani 1 1 d . . . . .
C6 C 0.2252(3) 0.5448(5) 0.59107(16) 0.0206(6) Uani 1 1 d . . . . .
H6 H 0.195096 0.418756 0.559787 0.025 Uiso 1 1 calc R . . . .
C9 C 0.5469(3) 0.2599(4) 0.54000(15) 0.0152(5) Uani 1 1 d . . . . .
C2 C 0.4326(4) 0.7563(4) 0.67003(15) 0.0170(5) Uani 1 1 d . . . . .
H2 H 0.542693 0.772582 0.692072 0.020 Uiso 1 1 calc R . . . .
C4 C 0.1467(4) 0.8992(5) 0.65248(17) 0.0226(6) Uani 1 1 d . . . . .
H4 H 0.065828 1.011043 0.661487 0.027 Uiso 1 1 calc R . . . .
C5 C 0.1040(4) 0.7089(5) 0.60624(17) 0.0236(6) Uani 1 1 d . . . . .
H5 H -0.006913 0.691856 0.585340 0.028 Uiso 1 1 calc R . . . .
C8 C 0.6489(4) 0.3310(5) 0.67056(16) 0.0191(6) Uani 1 1 d . . . . .
H8 H 0.653806 0.403707 0.721505 0.023 Uiso 1 1 calc R . . . .
C3 C 0.3111(4) 0.9203(5) 0.68499(17) 0.0213(6) Uani 1 1 d . . . . .
H3 H 0.340001 1.045396 0.717049 0.026 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0236(4) 0.0231(3) 0.0162(3) 0.0019(3) 0.0007(2) 0.0081(3)
N1 0.0209(13) 0.0322(13) 0.0169(11) 0.0036(10) -0.0034(9) 0.0053(10)
C1 0.0154(12) 0.0169(12) 0.0118(10) 0.0023(13) -0.0005(8) 0.0013(12)
C7 0.0133(13) 0.0183(12) 0.0148(12) 0.0021(10) -0.0022(10) -0.0020(10)
C6 0.0202(14) 0.0258(17) 0.0155(11) -0.0038(12) -0.0048(10) 0.0023(12)
C9 0.0165(13) 0.0156(12) 0.0135(12) 0.0020(10) 0.0011(10) -0.0006(10)
C2 0.0176(13) 0.0195(13) 0.0137(12) 0.0017(10) 0.0011(10) -0.0024(11)
C4 0.0246(15) 0.0249(15) 0.0184(13) 0.0034(12) 0.0043(11) 0.0089(12)
C5 0.0168(14) 0.0353(17) 0.0187(14) -0.0007(13) -0.0026(11) 0.0061(12)
C8 0.0190(14) 0.0255(15) 0.0127(12) 0.0008(11) -0.0031(11) 0.0011(11)
C3 0.0284(16) 0.0175(13) 0.0181(13) -0.0009(11) 0.0056(11) -0.0018(12)
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'
N N 0.0061 0.0033 '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
N1 S1 C9 95.15(12) . . ?
C8 N1 S1 108.8(2) . . ?
C6 C1 C7 122.1(3) . . ?
C6 C1 C2 118.2(3) . . ?
C2 C1 C7 119.6(2) . . ?
C9 C7 C1 128.3(2) . . ?
C9 C7 C8 108.9(2) . . ?
C8 C7 C1 122.8(2) . . ?
C5 C6 C1 120.8(3) . . ?
C7 C9 S1 109.6(2) . . ?
C7 C9 C9 129.7(2) . 2_656 ?
C9 C9 S1 120.73(18) 2_656 . ?
C3 C2 C1 120.9(3) . . ?
C3 C4 C5 119.3(3) . . ?
C6 C5 C4 120.5(3) . . ?
N1 C8 C7 117.6(2) . . ?
C4 C3 C2 120.4(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
S1 N1 1.656(2) . ?
S1 C9 1.714(3) . ?
N1 C8 1.316(4) . ?
C1 C7 1.479(4) . ?
C1 C6 1.395(4) . ?
C1 C2 1.400(4) . ?
C7 C9 1.374(4) . ?
C7 C8 1.431(4) . ?
C6 C5 1.384(4) . ?
C9 C9 1.475(5) 2_656 ?
C2 C3 1.384(4) . ?
C4 C5 1.390(4) . ?
C4 C3 1.385(4) . ?
