#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/90/2209053.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209053
loop_
_publ_author_name
'Huang, Zhi-Qiang'
'Du, Zhi-Qiang'
'Du, Guan-Sheng'
'Yan, Jun'
_publ_section_title
;
 3-(1,3-Benzothiazol-2-yl)-2-naphthol
;
_journal_coeditor_code           XU2026
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2010
_journal_page_last               o2011
_journal_paper_doi               10.1107/S1600536806013730
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H11 N O S'
_chemical_formula_moiety         'C17 H11 N O S'
_chemical_formula_sum            'C17 H11 N O S'
_chemical_formula_weight         277.33
_chemical_name_systematic
;
3-(1,3-Benzothiazol-2-yl)-2-naphthol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.120(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3634(9)
_cell_length_b                   8.5293(12)
_cell_length_c                   23.588(3)
_cell_measurement_reflns_used    1867
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.5
_cell_volume                     1275.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_sigmaI/netI    0.049
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6746
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.860
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0699P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.106
_refine_ls_wR_factor_ref         0.112
_reflns_number_gt                1755
_reflns_number_total             2497
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2026.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2209053
_cod_database_fobs_code          2209053
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.72200(9) 0.29151(6) 1.01835(2) 0.0513(2) Uani d . 1
O O1 0.1516(2) 0.28956(18) 0.88196(6) 0.0635(4) Uani d . 1
H H1 0.1679 0.2485 0.9135 0.095 Uiso calc R 1
N N1 0.3364(3) 0.22036(18) 0.98216(6) 0.0469(4) Uani d . 1
C C1 0.5026(3) 0.2965(2) 0.96802(7) 0.0407(5) Uani d . 1
C C2 0.5791(3) 0.1769(2) 1.06196(8) 0.0462(5) Uani d . 1
C C3 0.6395(4) 0.1132(2) 1.11535(8) 0.0557(6) Uani d . 1
H H3 0.7747 0.1290 1.1328 0.067 Uiso calc R 1
C C4 0.4943(4) 0.0265(2) 1.14146(9) 0.0580(6) Uani d . 1
H H4 0.5322 -0.0164 1.1772 0.070 Uiso calc R 1
C C5 0.2931(4) 0.0015(2) 1.11600(8) 0.0567(6) Uani d . 1
H H5 0.1981 -0.0576 1.1348 0.068 Uiso calc R 1
C C6 0.2312(4) 0.0630(2) 1.06303(8) 0.0516(5) Uani d . 1
H H6 0.0958 0.0457 1.0459 0.062 Uiso calc R 1
C C7 0.3751(3) 0.1509(2) 1.03597(8) 0.0443(5) Uani d . 1
C C8 0.5074(3) 0.3788(2) 0.91374(7) 0.0415(5) Uani d . 1
C C9 0.3275(3) 0.3713(2) 0.87229(8) 0.0448(5) Uani d . 1
C C10 0.3316(3) 0.4494(2) 0.82143(8) 0.0512(5) Uani d . 1
H H10 0.2153 0.4432 0.7947 0.061 Uiso calc R 1
C C11 0.5069(3) 0.5382(2) 0.80891(8) 0.0445(5) Uani d . 1
C C12 0.5120(4) 0.6237(2) 0.75716(8) 0.0527(5) Uani d . 1
H H12 0.3952 0.6221 0.7305 0.063 Uiso calc R 1
C C13 0.6847(4) 0.7073(2) 0.74634(9) 0.0565(6) Uani d . 1
H H13 0.6848 0.7634 0.7125 0.068 Uiso calc R 1
C C14 0.8636(4) 0.7101(2) 0.78572(9) 0.0585(6) Uani d . 1
H H14 0.9829 0.7657 0.7775 0.070 Uiso calc R 1
C C15 0.8630(3) 0.6318(2) 0.83576(9) 0.0529(5) Uani d . 1
H H15 0.9817 0.6354 0.8617 0.063 Uiso calc R 1
C C16 0.6868(3) 0.5457(2) 0.84893(8) 0.0421(5) Uani d . 1
C C17 0.6793(3) 0.4634(2) 0.90090(8) 0.0446(5) Uani d . 1
H H17 0.7964 0.4672 0.9274 0.053 Uiso calc R 1
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'
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
C2 S1 C1 89.28(10)
C9 O1 H1 109.5
C1 N1 C7 111.06(17)
N1 C1 C8 122.79(17)
N1 C1 S1 115.37(14)
C8 C1 S1 121.84(15)
C3 C2 C7 120.2(2)
C3 C2 S1 129.71(18)
C7 C2 S1 110.08(14)
C4 C3 C2 118.3(2)
C4 C3 H3 120.9
C2 C3 H3 120.9
C3 C4 C5 121.56(19)
C3 C4 H4 119.2
C5 C4 H4 119.2
C6 C5 C4 120.9(2)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C7 118.5(2)
C5 C6 H6 120.8
C7 C6 H6 120.8
C6 C7 N1 125.22(18)
C6 C7 C2 120.58(17)
N1 C7 C2 114.20(19)
C17 C8 C9 118.47(17)
C17 C8 C1 121.81(17)
C9 C8 C1 119.73(18)
O1 C9 C10 118.45(17)
O1 C9 C8 121.82(17)
C10 C9 C8 119.73(19)
C9 C10 C11 121.53(18)
C9 C10 H10 119.2
C11 C10 H10 119.2
C10 C11 C16 119.63(17)
C10 C11 C12 122.46(18)
C16 C11 C12 117.91(19)
C13 C12 C11 120.82(19)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 120.6(2)
C12 C13 H13 119.7
C14 C13 H13 119.7
C15 C14 C13 120.1(2)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C15 C16 121.10(19)
C14 C15 H15 119.4
C16 C15 H15 119.4
C15 C16 C17 122.80(18)
C15 C16 C11 119.43(17)
C17 C16 C11 117.77(18)
C8 C17 C16 122.86(18)
C8 C17 H17 118.6
C16 C17 H17 118.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.734(2)
S1 C1 1.7506(19)
O1 C9 1.355(2)
O1 H1 0.8200
N1 C1 1.310(3)
N1 C7 1.402(2)
C1 C8 1.463(2)
C2 C3 1.394(3)
C2 C7 1.403(3)
C3 C4 1.371(3)
C3 H3 0.9300
C4 C5 1.381(3)
C4 H4 0.9300
C5 C6 1.380(3)
C5 H5 0.9300
C6 C7 1.383(3)
C6 H6 0.9300
C8 C17 1.367(3)
C8 C9 1.439(3)
C9 C10 1.374(3)
C10 C11 1.402(3)
C10 H10 0.9300
C11 C16 1.419(3)
C11 C12 1.425(3)
C12 C13 1.353(3)
C12 H12 0.9300
C13 C14 1.404(3)
C13 H13 0.9300
C14 C15 1.356(3)
C14 H14 0.9300
C15 C16 1.398(3)
C15 H15 0.9300
C16 C17 1.417(3)
C17 H17 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.88 2.612(2) 149 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 N1 C1 C8 179.29(16)
C7 N1 C1 S1 0.1(2)
C2 S1 C1 N1 0.22(15)
C2 S1 C1 C8 -179.01(15)
C1 S1 C2 C3 179.47(19)
C1 S1 C2 C7 -0.43(14)
C7 C2 C3 C4 -0.5(3)
S1 C2 C3 C4 179.56(16)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C6 0.1(3)
C4 C5 C6 C7 -0.2(3)
C5 C6 C7 N1 179.71(17)
C5 C6 C7 C2 -0.1(3)
C1 N1 C7 C6 179.78(18)
C1 N1 C7 C2 -0.4(2)
C3 C2 C7 C6 0.5(3)
S1 C2 C7 C6 -179.62(15)
C3 C2 C7 N1 -179.34(17)
S1 C2 C7 N1 0.6(2)
N1 C1 C8 C17 177.03(17)
S1 C1 C8 C17 -3.8(2)
N1 C1 C8 C9 -3.1(3)
S1 C1 C8 C9 176.12(13)
C17 C8 C9 O1 179.89(17)
C1 C8 C9 O1 0.0(3)
C17 C8 C9 C10 -0.4(3)
C1 C8 C9 C10 179.63(17)
O1 C9 C10 C11 179.04(17)
C8 C9 C10 C11 -0.6(3)
C9 C10 C11 C16 1.3(3)
C9 C10 C11 C12 -178.10(18)
C10 C11 C12 C13 -179.54(18)
C16 C11 C12 C13 1.0(3)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C15 -1.6(3)
C13 C14 C15 C16 0.8(3)
C14 C15 C16 C17 -179.48(19)
C14 C15 C16 C11 1.0(3)
C10 C11 C16 C15 178.70(17)
C12 C11 C16 C15 -1.9(3)
C10 C11 C16 C17 -0.9(2)
C12 C11 C16 C17 178.57(16)
C9 C8 C17 C16 0.9(3)
C1 C8 C17 C16 -179.20(16)
C15 C16 C17 C8 -179.77(17)
C11 C16 C17 C8 -0.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14595367
