Controllable assembly of the benzothiazole framework using a C[triple bond, length as m-dash]C triple bond as a one-carbon synthon.
Huang, Yubing; Yan, Donghao; Wang, Xu; Zhou, Peiqi; Wu, Wanqing; Jiang, Huanfeng; Chemical communications (Cambridge, England) 54 (2018) 1742–1745; doi:10.1039/c7cc09855c

data_7121181
_publ_section_title
;
 Controllable assembly of the benzothiazole framework using a C[triple
 bond, length as m-dash]C triple bond as a one-carbon synthon.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1742
_journal_page_last               1745
_journal_paper_doi               10.1039/c7cc09855c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C14 H10 Br N S'
_chemical_formula_sum            'C14 H10 Br N S'
_chemical_formula_weight         304.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1q3t8x
_audit_creation_date             2017-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-27 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                82.039(2)
_cell_angle_beta                 85.191(3)
_cell_angle_gamma                89.175(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6340(3)
_cell_length_b                   9.3287(3)
_cell_length_c                   9.7895(2)
_cell_measurement_reflns_used    7653
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5120
_cell_measurement_theta_min      4.5610
_cell_volume                     597.89(4)
_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)'
_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 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      2.00  29.00   1.00    1.00    --   41.11 -99.00 150.00   27
  2  \w     52.00  80.00   1.00    1.00    --   41.11-125.00 120.00   28
  3  \w     49.00 117.00   1.00    1.00    --  106.95 -77.00   0.00   68
  4  \w     91.00 119.00   1.00    1.00    --  106.95-125.00-120.00   28
  5  \w     56.00  90.00   1.00    1.00    --  106.95-125.00-120.00   34
  6  \w     23.00  88.00   1.00    1.00    --   41.11-125.00-120.00   65
  7  \w     28.00  88.00   1.00    1.00    --  106.95 -94.00 -30.00   60
  8  \w     42.00 133.00   1.00    1.00    --  106.95 -30.00  30.00   91
  9  \w    139.00 178.00   1.00    1.00    --  106.95  30.00  90.00   39
 10  \w    131.00 176.00   1.00    1.00    --  106.95  61.00 -30.00   45
 11  \w    147.00 177.00   1.00    1.00    --  106.95 125.00-120.00   30
 12  \w     98.00 172.00   1.00    1.00    --  106.95 125.00  30.00   74
 13  \w     97.00 149.00   1.00    1.00    --  106.95 125.00   0.00   52
 14  \w     85.00 133.00   1.00    1.00    --  106.95  30.00  90.00   48
 15  \w     45.00  89.00   1.00    1.00    --  106.95 -94.00 150.00   44
 16  \w     36.00 126.00   1.00    1.00    --  106.95 -30.00 -90.00   90
 17  \w   -107.00  -2.00   1.00    1.00    --  -41.11 -19.00 -30.00  105
 18  \w   -115.00 -22.00   1.00    1.00    --  -41.11 -37.00 -90.00   93
 19  \w     -9.00  31.00   1.00    1.00    --  -41.23  57.00 -30.00   40
 20  \w   -114.00 -17.00   1.00    1.00    --  -41.23 -77.00-150.00   97
 21  \w    -63.00 -12.00   1.00    1.00    --  -41.23  57.00 -30.00   51
 22  \w     10.00  50.00   1.00    1.00    --   41.23  77.00 -60.00   40
 23  \w     17.00  82.00   1.00    1.00    --   41.23  57.00 120.00   65
 24  \w    -18.00  36.00   1.00    1.00    --   41.23 -77.00  60.00   54
 25  \w     10.00  46.00   1.00    1.00    --   41.23  70.00-156.41   36
 26  \w      9.00  60.00   1.00    1.00    --   41.23  77.00  30.00   51
 27  \w     74.00 109.00   1.00    1.00    --  106.95  77.00 150.00   35
 28  \w     75.00 101.00   1.00    1.00    --  106.95  77.00  60.00   26
 29  \w     75.00 101.00   1.00    1.00    --  106.95  77.00 -90.00   26
 30  \w    133.00 159.00   1.00    1.00    --  106.95  77.00 -90.00   26
 31  \w     78.00 134.00   1.00    1.00    --  106.95  61.00-180.00   56
 32  \w    119.00 171.00   1.00    1.00    --  106.95  61.00-150.00   52
 33  \w     78.00 141.00   1.00    1.00    --  106.95  61.00-120.00   63
 34  \w    146.00 172.00   1.00    1.00    --  106.95  77.00-180.00   26
 35  \w     75.00 100.00   1.00    1.00    --  106.95  77.00-150.00   25
 36  \w     74.00 100.00   1.00    1.00    --  106.95  77.00-180.00   26
 37  \w     79.00 124.00   1.00    1.00    --  106.95  61.00  30.00   45
 38  \w     74.00 100.00   1.00    1.00    --  106.95  77.00-120.00   26
 39  \w     75.00 118.00   1.00    1.00    --  106.95  77.00 120.00   43
 40  \w     80.00 106.00   1.00    1.00    --  106.95  61.00  60.00   26
 41  \w     78.00 132.00   1.00    1.00    --  106.95  61.00   0.00   54
 42  \w     78.00 118.00   1.00    1.00    --  106.95  61.00 -30.00   40
 43  \w     74.00 100.00   1.00    1.00    --  106.95  77.00  30.00   26
 44  \w     81.00 107.00   1.00    1.00    --  106.95  45.00 120.00   26
 45  \w     74.00 110.00   1.00    1.00    --  106.95  77.00 -60.00   36
 46  \w     80.00 116.00   1.00    1.00    --  106.95  61.00-150.00   36
 47  \w     80.00 110.00   1.00    1.00    --  106.95  61.00 -60.00   30
 48  \w     78.00 134.00   1.00    1.00    --  106.95  61.00 -90.00   56
 49  \w     75.00 101.00   1.00    1.00    --  106.95  77.00   0.00   26
 50  \w     75.00 117.00   1.00    1.00    --  106.95  77.00 -30.00   42
 51  \w     78.00 129.00   1.00    1.00    --  106.95  61.00 150.00   51
 52  \w     78.00 103.00   1.00    1.00    --  106.95  61.00 120.00   25
 53  \w    126.00 151.00   1.00    1.00    --  106.95 178.00   0.00   25
 54  \w     12.00  37.00   1.00    1.00    --   46.00  81.00 119.60   25
 55  \w     20.00  45.00   1.00    1.00    --   54.00  81.00 -66.74   25
 56  \w     28.00  67.00   1.00    1.00    --   58.00  76.00  66.94   39
 57  \w     26.00  59.00   1.00    1.00    --   58.00  76.00 -34.49   33
 58  \w     30.00  68.00   1.00    1.00    --   62.00  76.00-136.68   38
 59  \w     31.00  57.00   1.00    1.00    --   62.00  77.00  16.05   26
 60  \w     31.00  43.00   1.00    1.00    --   62.00  76.00 141.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0440553000
_diffrn_orient_matrix_UB_12      -0.0785361000
_diffrn_orient_matrix_UB_13      -0.1278359000
_diffrn_orient_matrix_UB_21      -0.0103913000
_diffrn_orient_matrix_UB_22      0.1455673000
_diffrn_orient_matrix_UB_23      -0.0952160000
_diffrn_orient_matrix_UB_31      0.2283954000
_diffrn_orient_matrix_UB_32      0.0212445000
_diffrn_orient_matrix_UB_33      0.0068006000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9253
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.476
_diffrn_reflns_theta_min         4.576
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21539
_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    1.690
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0271
_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/[\s^2^(Fo^2^)+(0.0456P)^2^+0.7760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2319
_reflns_number_total             2350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09855c2.cif
_cod_data_source_block           4d
_cod_depositor_comments          'Adding full bibliography for 7121181.cif.'
_cod_database_code               7121181
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.581
_shelx_estimated_absorpt_t_min   0.483
_reflns_odcompleteness_completeness 99.95
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C10(H10), C14(H14), C4(H4), C2(H2), C3(H3), C11(H11)
;
_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 3.438
_oxdiff_exptl_absorpt_empirical_full_min 0.516