#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/05/2220574.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_2220574
loop_
_publ_author_name
'Su, Zhen-Hong'
'Wang, Qing-Zhi'
'Teng, Lei'
'Zhang, Yong'
_publ_section_title
;
 4-(1,3-Benzothiazol-2-yl)-N-(2-pyridylmethyl)aniline
 monohydrate
;
_journal_coeditor_code           LH2740
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o86
_journal_paper_doi               10.1107/S1600536808041238
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H15 N3 S, H2 O'
_chemical_formula_moiety         'C19 H15 N3 S, H2 O'
_chemical_formula_sum            'C19 H17 N3 O S'
_chemical_formula_weight         335.42
_chemical_name_systematic
;
4-(1,3-Benzothiazol-2-yl)-N-(2-pyridylmethyl)aniline monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.5970(10)
_cell_angle_beta                 103.5990(10)
_cell_angle_gamma                99.8130(10)
_cell_formula_units_Z            2
_cell_length_a                   6.5042(3)
_cell_length_b                   11.5721(5)
_cell_length_c                   11.9415(5)
_cell_measurement_reflns_used    1809
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.8
_cell_volume                     840.52(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0738
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5408
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.9606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0653P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2342
_reflns_number_total             3243
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2740.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_sg_symbol_H-M      P-1
_cod_database_code               2220574
_cod_database_fobs_code          2220574
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.4402(3) 0.43406(18) -0.20560(17) 0.0522(5) Uani d . 1 . .
C C2 0.5812(4) 0.4597(2) -0.2737(2) 0.0691(7) Uani d . 1 . .
H H2 0.6917 0.4186 -0.2762 0.083 Uiso calc R 1 . .
C C3 0.5534(5) 0.5473(2) -0.3374(2) 0.0801(8) Uani d . 1 . .
H H3 0.6479 0.5659 -0.3826 0.096 Uiso calc R 1 . .
C C4 0.3900(5) 0.6079(2) -0.3361(2) 0.0845(8) Uani d . 1 . .
H H4 0.3748 0.6659 -0.3810 0.101 Uiso calc R 1 . .
C C5 0.2492(5) 0.5842(2) -0.2699(2) 0.0785(7) Uani d . 1 . .
H H5 0.1382 0.6252 -0.2692 0.094 Uiso calc R 1 . .
C C6 0.2765(4) 0.49671(19) -0.20326(18) 0.0580(6) Uani d . 1 . .
C C7 0.2929(3) 0.34399(17) -0.08419(16) 0.0464(5) Uani d . 1 . .
C C8 0.2525(3) 0.26241(17) -0.00708(16) 0.0463(5) Uani d . 1 . .
C C9 0.3952(3) 0.18903(19) 0.02435(17) 0.0517(5) Uani d . 1 . .
H H9 0.5194 0.1946 -0.0020 0.062 Uiso calc R 1 . .
C C10 0.3564(3) 0.10838(19) 0.09370(17) 0.0532(5) Uani d . 1 . .
H H10 0.4541 0.0600 0.1128 0.064 Uiso calc R 1 . .
C C11 0.1720(3) 0.09818(18) 0.13580(17) 0.0492(5) Uani d . 1 . .
C C12 0.0305(3) 0.17363(18) 0.10587(18) 0.0529(5) Uani d . 1 . .
H H12 -0.0918 0.1701 0.1339 0.064 Uiso calc R 1 . .
C C13 0.0701(3) 0.25266(19) 0.03563(18) 0.0528(5) Uani d . 1 . .
H H13 -0.0275 0.3010 0.0160 0.063 Uiso calc R 1 . .
C C15 -0.0523(3) -0.00822(19) 0.24393(18) 0.0552(5) Uani d . 1 . .
H H15A -0.0695 -0.0890 0.2582 0.066 Uiso calc R 1 . .
H H15B -0.1768 -0.0071 0.1811 0.066 Uiso calc R 1 . .
C C16 -0.0534(3) 0.07696(18) 0.35445(16) 0.0479(5) Uani d . 1 . .
C C17 0.1128(4) 0.1740(2) 0.41260(19) 0.0659(6) Uani d . 1 . .
H H17 0.2336 0.1912 0.3844 0.079 Uiso calc R 1 . .
C C18 0.0975(5) 0.2455(2) 0.5135(2) 0.0775(7) Uani d . 1 . .
H H18 0.2085 0.3115 0.5542 0.093 Uiso calc R 1 . .
C C19 -0.0808(5) 0.2189(2) 0.5533(2) 0.0765(7) Uani d . 1 . .
H H19 -0.0941 0.2657 0.6214 0.092 Uiso calc R 1 . .
C C20 -0.2392(4) 0.1217(2) 0.4904(2) 0.0727(7) Uani d . 1 . .
H H20 -0.3609 0.1032 0.5176 0.087 Uiso calc R 1 . .
N N1 0.4450(3) 0.34715(15) -0.13801(15) 0.0531(4) Uani d . 1 . .
N N2 0.1390(3) 0.01759(17) 0.20410(16) 0.0592(5) Uani d D 1 . .
H H2A 0.228(3) -0.0288(16) 0.2148(19) 0.069(7) Uiso d D 1 . .
N N3 -0.2300(3) 0.05079(16) 0.39105(15) 0.0590(5) Uani d . 1 . .
O O1 0.4135(2) -0.14685(15) 0.26027(16) 0.0699(5) Uani d D 1 . .
H H1A 0.526(3) -0.0972(19) 0.299(2) 0.105 Uiso d D 1 . .
H H1B 0.450(4) -0.2003(18) 0.218(2) 0.105 Uiso d D 1 . .
S S1 0.12798(10) 0.44713(5) -0.11189(5) 0.0648(2) 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
C2 C1 C6 . . 119.7(2) ?
C2 C1 N1 . . 125.2(2) ?
C6 C1 N1 . . 115.02(19) ?
C3 C2 C1 . . 118.4(2) ?
C3 C2 H2 . . 120.8 ?
C1 C2 H2 . . 120.8 ?
C4 C3 C2 . . 121.8(3) ?
C4 C3 H3 . . 119.1 ?
C2 C3 H3 . . 119.1 ?
C5 C4 C3 . . 120.9(3) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 118.2(3) ?
C4 C5 H5 . . 120.9 ?
C6 C5 H5 . . 120.9 ?
C1 C6 C5 . . 121.0(2) ?
C1 C6 S1 . . 109.75(17) ?
C5 C6 S1 . . 129.3(2) ?
N1 C7 C8 . . 124.97(18) ?
N1 C7 S1 . . 114.73(15) ?
C8 C7 S1 . . 120.30(15) ?
C9 C8 C13 . . 117.53(19) ?
C9 C8 C7 . . 120.40(18) ?
C13 C8 C7 . . 122.05(19) ?
C10 C9 C8 . . 121.39(19) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C11 . . 120.9(2) ?
C9 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
N2 C11 C12 . . 123.07(19) ?
N2 C11 C10 . . 119.30(19) ?
C12 C11 C10 . . 117.63(19) ?
C13 C12 C11 . . 120.76(19) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C8 . . 121.7(2) ?
C12 C13 H13 . . 119.1 ?
C8 C13 H13 . . 119.1 ?
N2 C15 C16 . . 115.24(17) ?
N2 C15 H15A . . 108.5 ?
C16 C15 H15A . . 108.5 ?
N2 C15 H15B . . 108.5 ?
C16 C15 H15B . . 108.5 ?
H15A C15 H15B . . 107.5 ?
N3 C16 C17 . . 122.3(2) ?
N3 C16 C15 . . 114.46(18) ?
C17 C16 C15 . . 123.3(2) ?
C16 C17 C18 . . 118.9(2) ?
C16 C17 H17 . . 120.6 ?
C18 C17 H17 . . 120.6 ?
C19 C18 C17 . . 119.6(2) ?
C19 C18 H18 . . 120.2 ?
C17 C18 H18 . . 120.2 ?
C20 C19 C18 . . 118.0(2) ?
C20 C19 H19 . . 121.0 ?
C18 C19 H19 . . 121.0 ?
N3 C20 C19 . . 123.8(2) ?
N3 C20 H20 . . 118.1 ?
C19 C20 H20 . . 118.1 ?
C7 N1 C1 . . 111.11(18) ?
C11 N2 C15 . . 124.34(19) ?
C11 N2 O1 . . 124.36(14) ?
C15 N2 O1 . . 110.78(13) ?
C11 N2 H2A . . 117.8(16) ?
C15 N2 H2A . . 117.1(16) ?
C16 N3 C20 . . 117.4(2) ?
N2 O1 H1A . . 99(2) ?
N2 O1 H1B . . 132(2) ?
H1A O1 H1B . . 107.1(15) ?
C6 S1 C7 . . 89.37(10) ?
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
C1 C2 . 1.389(3) ?
C1 C6 . 1.390(3) ?
C1 N1 . 1.390(3) ?
C2 C3 . 1.376(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.371(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.366(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.398(3) ?
C5 H5 . 0.9300 ?
C6 S1 . 1.723(2) ?
C7 N1 . 1.299(3) ?
C7 C8 . 1.458(3) ?
C7 S1 . 1.757(2) ?
C8 C9 . 1.391(3) ?
C8 C13 . 1.392(3) ?
C9 C10 . 1.377(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.400(3) ?
C10 H10 . 0.9300 ?
C11 N2 . 1.360(3) ?
C11 C12 . 1.400(3) ?
C12 C13 . 1.372(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C15 N2 . 1.436(3) ?
C15 C16 . 1.512(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 N3 . 1.328(2) ?
C16 C17 . 1.373(3) ?
C17 C18 . 1.378(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.361(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.360(3) ?
C19 H19 . 0.9300 ?
C20 N3 . 1.345(3) ?
C20 H20 . 0.9300 ?
N2 O1 . 2.877(2) ?
N2 H2A . 0.856(10) ?
O1 H1A . 0.830(9) ?
O1 H1B . 0.836(9) ?
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
N2 H2A O1 . 0.856(10) 2.030(11) 2.877(2) 171(2) yes
O1 H1B N1 2_655 0.836(9) 2.102(11) 2.929(2) 170(3) yes
O1 H1A N3 1_655 0.830(9) 2.069(10) 2.889(2) 169(3) yes
C18 H18 Cg 1_556 0.93 2.82 3.689(3) 156 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
C6 C1 C2 C3 . . . . 0.0(3) ?
N1 C1 C2 C3 . . . . 179.0(2) ?
C1 C2 C3 C4 . . . . -0.8(4) ?
C2 C3 C4 C5 . . . . 0.8(4) ?
C3 C4 C5 C6 . . . . 0.1(4) ?
C2 C1 C6 C5 . . . . 0.9(3) ?
N1 C1 C6 C5 . . . . -178.17(19) ?
C2 C1 C6 S1 . . . . -179.81(16) ?
N1 C1 C6 S1 . . . . 1.1(2) ?
C4 C5 C6 C1 . . . . -1.0(3) ?
C4 C5 C6 S1 . . . . 179.93(19) ?
N1 C7 C8 C9 . . . . 7.2(3) ?
S1 C7 C8 C9 . . . . -173.62(15) ?
N1 C7 C8 C13 . . . . -171.42(18) ?
S1 C7 C8 C13 . . . . 7.8(3) ?
C13 C8 C9 C10 . . . . 0.9(3) ?
C7 C8 C9 C10 . . . . -177.73(18) ?
C8 C9 C10 C11 . . . . -0.5(3) ?
C9 C10 C11 N2 . . . . -179.97(19) ?
C9 C10 C11 C12 . . . . -0.7(3) ?
N2 C11 C12 C13 . . . . -179.35(19) ?
C10 C11 C12 C13 . . . . 1.4(3) ?
C11 C12 C13 C8 . . . . -1.0(3) ?
C9 C8 C13 C12 . . . . -0.2(3) ?
C7 C8 C13 C12 . . . . 178.42(18) ?
N2 C15 C16 N3 . . . . -179.05(18) ?
N2 C15 C16 C17 . . . . 1.3(3) ?
N3 C16 C17 C18 . . . . 1.1(4) ?
C15 C16 C17 C18 . . . . -179.2(2) ?
C16 C17 C18 C19 . . . . -0.1(4) ?
C17 C18 C19 C20 . . . . -0.3(4) ?
C18 C19 C20 N3 . . . . -0.3(4) ?
C8 C7 N1 C1 . . . . 179.53(17) ?
S1 C7 N1 C1 . . . . 0.3(2) ?
C2 C1 N1 C7 . . . . -179.93(18) ?
C6 C1 N1 C7 . . . . -0.9(2) ?
C12 C11 N2 C15 . . . . 6.3(3) ?
C10 C11 N2 C15 . . . . -174.45(18) ?
C12 C11 N2 O1 . . . . 177.22(15) ?
C10 C11 N2 O1 . . . . -3.5(3) ?
C16 C15 N2 C11 . . . . -84.0(3) ?
C16 C15 N2 O1 . . . . 104.04(17) ?
C17 C16 N3 C20 . . . . -1.7(3) ?
C15 C16 N3 C20 . . . . 178.7(2) ?
C19 C20 N3 C16 . . . . 1.3(4) ?
C1 C6 S1 C7 . . . . -0.75(15) ?
C5 C6 S1 C7 . . . . 178.4(2) ?
N1 C7 S1 C6 . . . . 0.28(16) ?
C8 C7 S1 C6 . . . . -179.01(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655691
