Synthesis of a series of benzothiazole amide derivatives and their biological evaluation as potent hemostatic agents
Nong, Wenqian; Zhao, Anran; Wei, Jinrui; Cheng, Hui; Luo, Xuan; Lin, Cuiwu; RSC Advances 8 (2018) 6231–; doi:10.1039/C7RA13397A

data_7230096
_publ_section_title
;
 Synthesis of a series of benzothiazole amide derivatives and their
 biological evaluation as potent hemostatic agents
;
_journal_issue                   12
_journal_name_full               'RSC Advances'
_journal_page_first              6231
_journal_paper_doi               10.1039/C7RA13397A
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C18 H16 N2 O3 S'
_chemical_formula_sum            'C18 H16 N2 O3 S'
_chemical_formula_weight         340.39
_chemical_name_systematic
(E)-N-(benzo[d]thiazol-2-yl)-3-(3,4-dimethoxyphenyl)acrylamide
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-30 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                74.802(2)
_cell_angle_beta                 89.117(2)
_cell_angle_gamma                84.624(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2809(2)
_cell_length_b                   8.4804(3)
_cell_length_c                   12.4655(3)
_cell_measurement_reflns_used    6541
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6450
_cell_measurement_theta_min      5.3100
_cell_volume                     841.02(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.959
_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    -81.00 -55.00   0.50    0.50    --    0.00 -57.00  30.00   52
  2  \w    -39.00 -13.00   0.50    0.50    --    0.00 -38.00 120.00   52
  3  \w      9.00  35.00   0.50    0.50    --    0.00  38.00 -90.00   52
  4  \w    -50.00  17.00   0.50    0.50    --    0.00 -57.00  30.00  134
  5  \w    -18.00  88.00   0.50    0.50    --    0.00  19.00  30.00  212
  6  \w     63.00  89.00   0.50    0.50    --    0.00  38.00 -90.00   52
  7  \w     52.00 121.00   0.50    0.50    --   95.20 -82.00 -60.00  138
  8  \w     72.00 105.00   0.50    0.50    --   95.20  61.00   0.00   66
  9  \w      9.00 118.00   0.50    0.50    --   95.20 -61.00-150.00  218
 10  \w     83.00 115.00   0.50    0.50    --   95.20 -15.00  60.00   64
 11  \w     22.00 116.00   0.50    0.50    --   95.20 -61.00  60.00  188
 12  \w      6.00  75.00   0.50    0.50    --   95.20 -15.00  60.00  138
 13  \w     60.00 101.00   0.50    0.50    --   95.20 -82.00   0.00   82
 14  \w     64.00  95.00   0.50    0.50    --   95.20 -82.00 150.00   62
 15  \w     38.00 125.00   0.50    0.50    --   95.20 -82.00-150.00  174
 16  \w     82.00 185.00   0.50    0.50    --   95.20  30.00  30.00  206
 17  \w     81.00 127.00   0.50    0.50    --   95.20  30.00  60.00   92
 18  \w    137.00 164.00   0.50    0.50    --   95.20  30.00  60.00   54
 19  \w     24.00 126.00   0.50    0.50    --   95.20 -82.00  60.00  204
 20  \w     73.00 168.00   0.50    0.50    --   95.20  15.00 -30.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0023566000
_diffrn_orient_matrix_UB_12      0.0109953000
_diffrn_orient_matrix_UB_13      0.1214363000
_diffrn_orient_matrix_UB_21      -0.1840407000
_diffrn_orient_matrix_UB_22      -0.0153195000
_diffrn_orient_matrix_UB_23      0.0043073000
_diffrn_orient_matrix_UB_31      0.0322986000
_diffrn_orient_matrix_UB_32      -0.1881202000
_diffrn_orient_matrix_UB_33      0.0404562000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7491
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.014
_diffrn_reflns_theta_min         3.675
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0080(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0669P)^2^+0.6562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3176
_reflns_number_total             3284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra13397a2.cif
_cod_data_source_block           rgs
_cod_database_code               7230096
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.807
_shelx_estimated_absorpt_t_min   0.730
_reflns_odcompleteness_completeness 99.53
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C13(H13), C2(H2), C1(H1A), C15(H15), C16(H16), C14(H14),
 C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 12.416
_oxdiff_exptl_absorpt_empirical_full_min 0.585