#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/14/2221429.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_2221429
loop_
_publ_author_name
'Badahdaha, Khadija O.'
'Asiri, Abdullah Mohamed'
'Ng, Seik Weng'
_publ_section_title
;
 2-(1,3-Benzothiazol-2-yliminomethyl)-2-naphthol
;
_journal_coeditor_code           LH2783
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o759
_journal_paper_doi               10.1107/S1600536809008514
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H12 N2 O S'
_chemical_formula_moiety         'C18 H12 N2 O S'
_chemical_formula_sum            'C18 H12 N2 O S'
_chemical_formula_weight         304.36
_chemical_name_systematic
;
2-(1,3-Benzothiazol-2-yliminomethyl)-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                 101.323(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6398(2)
_cell_length_b                   14.9687(4)
_cell_length_c                   9.6646(2)
_cell_measurement_reflns_used    2677
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.5
_cell_volume                     1367.41(6)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       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  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12442
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular block'
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2396
_reflns_number_total             3139
_reflns_threshold_expression     I>2Ĭ)
_cod_data_source_file            lh2783.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1367.41(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221429
_cod_database_fobs_code          2221429
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.62414(5) 0.57067(3) 0.89471(5) 0.02326(15) Uani d . 1 . .
O O1 0.28598(15) 0.35583(9) 0.77536(15) 0.0261(3) Uani d D 1 . .
H H1 0.348(2) 0.3964(14) 0.782(3) 0.057(9) Uiso d D 1 . .
N N1 0.41330(16) 0.49518(10) 0.70645(17) 0.0214(4) Uani d . 1 . .
N N2 0.53279(16) 0.62326(11) 0.63631(17) 0.0218(3) Uani d . 1 . .
C C1 0.19789(19) 0.36352(12) 0.6498(2) 0.0207(4) Uani d . 1 . .
C C2 0.0903(2) 0.29840(13) 0.6173(2) 0.0236(4) Uani d . 1 . .
H H2 0.0831 0.2524 0.6833 0.028 Uiso calc R 1 . .
C C3 -0.0028(2) 0.30118(13) 0.4924(2) 0.0227(4) Uani d . 1 . .
H H3 -0.0733 0.2562 0.4715 0.027 Uiso calc R 1 . .
C C4 0.00270(19) 0.37013(12) 0.3918(2) 0.0205(4) Uani d . 1 . .
C C5 -0.0966(2) 0.37268(13) 0.2635(2) 0.0242(4) Uani d . 1 . .
H H5 -0.1667 0.3274 0.2434 0.029 Uiso calc R 1 . .
C C6 -0.0935(2) 0.43936(14) 0.1678(2) 0.0257(4) Uani d . 1 . .
H H6 -0.1613 0.4407 0.0819 0.031 Uiso calc R 1 . .
C C7 0.0109(2) 0.50600(13) 0.1975(2) 0.0246(4) Uani d . 1 . .
H H7 0.0131 0.5526 0.1312 0.030 Uiso calc R 1 . .
C C8 0.1093(2) 0.50481(13) 0.3206(2) 0.0219(4) Uani d . 1 . .
H H8 0.1790 0.5504 0.3380 0.026 Uiso calc R 1 . .
C C9 0.10912(19) 0.43680(12) 0.42252(19) 0.0189(4) Uani d . 1 . .
C C10 0.20982(19) 0.43225(12) 0.5546(2) 0.0190(4) Uani d . 1 . .
C C11 0.3197(2) 0.49736(13) 0.5896(2) 0.0210(4) Uani d . 1 . .
H H11 0.3245 0.5443 0.5245 0.025 Uiso calc R 1 . .
C C12 0.51359(19) 0.56351(12) 0.7280(2) 0.0205(4) Uani d . 1 . .
C C13 0.64047(19) 0.68133(12) 0.6951(2) 0.0199(4) Uani d . 1 . .
C C14 0.6849(2) 0.75430(13) 0.6250(2) 0.0230(4) Uani d . 1 . .
H H14 0.6414 0.7675 0.5303 0.028 Uiso calc R 1 . .
C C15 0.7934(2) 0.80674(13) 0.6964(2) 0.0251(4) Uani d . 1 . .
H H15 0.8252 0.8562 0.6495 0.030 Uiso calc R 1 . .
C C16 0.8576(2) 0.78866(13) 0.8360(2) 0.0256(4) Uani d . 1 . .
H H16 0.9320 0.8260 0.8826 0.031 Uiso calc R 1 . .
C C17 0.8139(2) 0.71684(13) 0.9077(2) 0.0245(4) Uani d . 1 . .
H H17 0.8570 0.7046 1.0029 0.029 Uiso calc R 1 . .
C C18 0.7052(2) 0.66319(13) 0.8359(2) 0.0214(4) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C18 S1 C12 . . 88.83(9) ?
C1 O1 H1 . . 109(2) ?
C11 N1 C12 . . 116.99(16) ?
C12 N2 C13 . . 110.36(16) ?
O1 C1 C10 . . 122.56(17) ?
O1 C1 C2 . . 116.63(17) ?
C10 C1 C2 . . 120.82(18) ?
C3 C2 C1 . . 120.34(18) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 121.51(18) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C9 . . 120.17(18) ?
C5 C4 C3 . . 120.62(17) ?
C9 C4 C3 . . 119.21(18) ?
C6 C5 C4 . . 120.93(18) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C7 . . 119.37(19) ?
C5 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
C8 C7 C6 . . 120.97(19) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C7 C8 C9 . . 121.24(18) ?
C7 C8 H8 . . 119.4 ?
C9 C8 H8 . . 119.4 ?
C8 C9 C4 . . 117.32(17) ?
C8 C9 C10 . . 123.76(17) ?
C4 C9 C10 . . 118.92(17) ?
C1 C10 C11 . . 119.86(17) ?
C1 C10 C9 . . 119.17(17) ?
C11 C10 C9 . . 120.96(17) ?
N1 C11 C10 . . 122.94(18) ?
N1 C11 H11 . . 118.5 ?
C10 C11 H11 . . 118.5 ?
N2 C12 N1 . . 126.25(17) ?
N2 C12 S1 . . 116.32(14) ?
N1 C12 S1 . . 117.44(14) ?
N2 C13 C14 . . 124.58(17) ?
N2 C13 C18 . . 115.42(17) ?
C14 C13 C18 . . 120.00(17) ?
C15 C14 C13 . . 118.50(18) ?
C15 C14 H14 . . 120.8 ?
C13 C14 H14 . . 120.7 ?
C14 C15 C16 . . 121.43(19) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C17 C16 C15 . . 120.81(19) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
C16 C17 C18 . . 118.07(19) ?
C16 C17 H17 . . 121.0 ?
C18 C17 H17 . . 121.0 ?
C17 C18 C13 . . 121.18(18) ?
C17 C18 S1 . . 129.72(16) ?
C13 C18 S1 . . 109.07(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C18 . 1.740(2) ?
S1 C12 . 1.7519(19) ?
O1 C1 . 1.343(2) ?
O1 H1 . 0.843(10) ?
N1 C11 . 1.300(2) ?
N1 C12 . 1.395(2) ?
N2 C12 . 1.298(2) ?
N2 C13 . 1.387(2) ?
C1 C10 . 1.400(3) ?
C1 C2 . 1.413(3) ?
C2 C3 . 1.356(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.426(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.410(3) ?
C4 C9 . 1.420(3) ?
C5 C6 . 1.365(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.406(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.368(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.417(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.445(3) ?
C10 C11 . 1.430(3) ?
C11 H11 . 0.9500 ?
C13 C14 . 1.396(3) ?
C13 C18 . 1.408(3) ?
C14 C15 . 1.380(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.397(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.388(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.392(3) ?
C17 H17 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 . 0.840(10) 1.82(2) 2.573(2) 148(3) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -179.77(17) ?
C10 C1 C2 C3 . . . . 0.5(3) ?
C1 C2 C3 C4 . . . . -1.3(3) ?
C2 C3 C4 C5 . . . . -178.90(18) ?
C2 C3 C4 C9 . . . . 0.7(3) ?
C9 C4 C5 C6 . . . . -0.8(3) ?
C3 C4 C5 C6 . . . . 178.85(18) ?
C4 C5 C6 C7 . . . . 0.4(3) ?
C5 C6 C7 C8 . . . . 0.2(3) ?
C6 C7 C8 C9 . . . . -0.3(3) ?
C7 C8 C9 C4 . . . . -0.1(3) ?
C7 C8 C9 C10 . . . . -179.70(17) ?
C5 C4 C9 C8 . . . . 0.6(3) ?
C3 C4 C9 C8 . . . . -179.03(16) ?
C5 C4 C9 C10 . . . . -179.76(16) ?
C3 C4 C9 C10 . . . . 0.6(3) ?
O1 C1 C10 C11 . . . . 0.4(3) ?
C2 C1 C10 C11 . . . . -179.91(17) ?
O1 C1 C10 C9 . . . . -178.88(16) ?
C2 C1 C10 C9 . . . . 0.9(3) ?
C8 C9 C10 C1 . . . . 178.24(17) ?
C4 C9 C10 C1 . . . . -1.4(3) ?
C8 C9 C10 C11 . . . . -1.0(3) ?
C4 C9 C10 C11 . . . . 179.39(17) ?
C12 N1 C11 C10 . . . . -179.24(16) ?
C1 C10 C11 N1 . . . . 1.6(3) ?
C9 C10 C11 N1 . . . . -179.23(17) ?
C13 N2 C12 N1 . . . . 179.17(17) ?
C13 N2 C12 S1 . . . . -0.3(2) ?
C11 N1 C12 N2 . . . . -8.4(3) ?
C11 N1 C12 S1 . . . . 171.09(14) ?
C18 S1 C12 N2 . . . . -0.17(15) ?
C18 S1 C12 N1 . . . . -179.72(15) ?
C12 N2 C13 C14 . . . . -178.50(17) ?
C12 N2 C13 C18 . . . . 0.8(2) ?
N2 C13 C14 C15 . . . . 179.92(17) ?
C18 C13 C14 C15 . . . . 0.6(3) ?
C13 C14 C15 C16 . . . . -0.6(3) ?
C14 C15 C16 C17 . . . . 0.1(3) ?
C15 C16 C17 C18 . . . . 0.4(3) ?
C16 C17 C18 C13 . . . . -0.4(3) ?
C16 C17 C18 S1 . . . . -178.59(15) ?
N2 C13 C18 C17 . . . . -179.46(17) ?
C14 C13 C18 C17 . . . . -0.1(3) ?
N2 C13 C18 S1 . . . . -0.9(2) ?
C14 C13 C18 S1 . . . . 178.42(14) ?
C12 S1 C18 C17 . . . . 178.94(19) ?
C12 S1 C18 C13 . . . . 0.60(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23599942
