#------------------------------------------------------------------------------
#$Date: 2022-04-01 05:25:23 +0300 (Fri, 01 Apr 2022) $
#$Revision: 274193 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566729.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_1566729
loop_
_publ_author_name
'Abdallah, Amira E. M.'
'Elgemeie, Galal H.'
'Jones, Peter G.'
_publ_section_title
;
 3-(Benzo[d]thiazol-2-yl)-2H-chromen-2-one
;
_journal_coeditor_code           XI4003
_journal_issue                   3
_journal_name_full               IUCrData
_journal_page_first              x220332
_journal_paper_doi               10.1107/S2414314622003327
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C16 H9 N O2 S'
_chemical_formula_moiety         'C16 H9 N O2 S'
_chemical_formula_sum            'C16 H9 N O2 S'
_chemical_formula_weight         279.30
_chemical_name_systematic
;
3-(Benzo[d]thiazol-2-yl)-2H-chromen-2-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.911(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.60717(11)
_cell_length_b                   20.7275(5)
_cell_length_c                   12.6444(3)
_cell_measurement_reflns_used    20622
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.8370
_cell_measurement_theta_min      4.0700
_cell_volume                     1206.81(5)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            49602
_diffrn_reflns_theta_full        77.000
_diffrn_reflns_theta_max         77.926
_diffrn_reflns_theta_min         4.097
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.385
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.427
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.248
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0491
_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/[σ²(Fo²)+(0.0479P)²+1.2289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                2528
_reflns_number_total             2547
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xi4003sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566729
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.911
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 -0.03347(11) 0.58024(2) 0.44385(4) 0.01871(16) Uani d 1 . .
C C2 0.1290(5) 0.63202(10) 0.35289(16) 0.0179(4) Uani d 1 . .
N N3 0.0429(4) 0.62471(9) 0.25396(14) 0.0190(4) Uani d 1 . .
C C3A -0.1604(5) 0.57600(10) 0.24410(17) 0.0197(4) Uani d 1 . .
C C4 -0.3012(5) 0.55593(11) 0.14936(17) 0.0227(5) Uani d 1 . .
H H4 -0.257833 0.575871 0.084112 0.027 Uiso calc 1 . .
C C5 -0.5025(5) 0.50703(11) 0.15244(18) 0.0238(5) Uani d 1 . .
H H5 -0.600561 0.493791 0.088821 0.029 Uiso calc 1 . .
C C6 -0.5657(5) 0.47627(11) 0.24818(18) 0.0230(5) Uani d 1 . .
H H6 -0.704244 0.442317 0.248094 0.028 Uiso calc 1 . .
C C7 -0.4295(5) 0.49470(10) 0.34205(18) 0.0208(4) Uani d 1 . .
H H7 -0.471183 0.473769 0.406635 0.025 Uiso calc 1 . .
C C7A -0.2284(5) 0.54501(10) 0.33950(16) 0.0189(4) Uani d 1 . .
C C8 0.3479(4) 0.67984(10) 0.38551(16) 0.0174(4) Uani d 1 . .
C C9 0.4134(5) 0.68882(10) 0.49914(16) 0.0186(4) Uani d 1 . .
C C10 0.7662(5) 0.76940(10) 0.45552(16) 0.0174(4) Uani d 1 . .
C C11 0.9720(5) 0.81249(10) 0.49547(16) 0.0200(4) Uani d 1 . .
H H11 1.009311 0.816281 0.569554 0.024 Uiso calc 1 . .
C C12 1.1223(5) 0.84998(10) 0.42467(17) 0.0208(4) Uani d 1 . .
H H12 1.262170 0.880282 0.450509 0.025 Uiso calc 1 . .
C C13 1.0693(5) 0.84351(10) 0.31510(17) 0.0202(4) Uani d 1 . .
H H13 1.174863 0.869054 0.267249 0.024 Uiso calc 1 . .
C C14 0.8647(5) 0.80021(10) 0.27695(16) 0.0191(4) Uani d 1 . .
H H14 0.830301 0.796009 0.202773 0.023 Uiso calc 1 . .
C C15 0.7059(4) 0.76208(10) 0.34688(16) 0.0173(4) Uani d 1 . .
C C16 0.4906(4) 0.71565(10) 0.31393(16) 0.0173(4) Uani d 1 . .
H H16 0.447058 0.709837 0.240584 0.021 Uiso calc 1 . .
O O1 0.6178(3) 0.73370(7) 0.52821(11) 0.0198(3) Uani d 1 . .
O O2 0.2995(4) 0.65973(8) 0.56960(12) 0.0247(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C7A S1 C2 . . 88.87(10) y
N3 C2 C8 . . 122.13(19) ?
N3 C2 S1 . . 115.63(16) y
C8 C2 S1 . . 122.24(15) ?
C2 N3 C3A . . 110.75(18) y
N3 C3A C4 . . 125.9(2) ?
N3 C3A C7A . . 115.15(19) y
C4 C3A C7A . . 119.0(2) ?
C5 C4 C3A . . 119.1(2) ?
C4 C5 C6 . . 121.2(2) ?
C7 C6 C5 . . 120.9(2) ?
C6 C7 C7A . . 118.1(2) ?
C7 C7A C3A . . 121.7(2) ?
C7 C7A S1 . . 128.67(17) ?
C3A C7A S1 . . 109.57(16) y
C16 C8 C2 . . 121.80(18) ?
C16 C8 C9 . . 119.64(19) ?
C2 C8 C9 . . 118.56(18) ?
O2 C9 O1 . . 116.96(18) ?
O2 C9 C8 . . 125.2(2) ?
O1 C9 C8 . . 117.81(18) ?
O1 C10 C11 . . 116.83(18) ?
O1 C10 C15 . . 120.59(19) ?
C11 C10 C15 . . 122.58(19) ?
C10 C11 C12 . . 118.41(19) ?
C11 C12 C13 . . 120.6(2) ?
C14 C13 C12 . . 120.1(2) ?
C13 C14 C15 . . 120.63(19) ?
C10 C15 C14 . . 117.67(19) ?
C10 C15 C16 . . 118.07(19) ?
C14 C15 C16 . . 124.25(19) ?
C8 C16 C15 . . 121.26(19) ?
C9 O1 C10 . . 122.61(16) ?
C5 C4 H4 . . 120.5 ?
C3A C4 H4 . . 120.5 ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 H7 . . 121.0 ?
C7A C7 H7 . . 121.0 ?
C10 C11 H11 . . 120.8 ?
C12 C11 H11 . . 120.8 ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C8 C16 H16 . . 119.4 ?
C15 C16 H16 . . 119.4 ?
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 C7A . 1.733(2) y
S1 C2 . 1.758(2) y
C2 N3 . 1.308(3) y
C2 C8 . 1.464(3) ?
N3 C3A . 1.380(3) y
C3A C4 . 1.406(3) ?
C3A C7A . 1.411(3) y
C4 C5 . 1.375(3) ?
C5 C6 . 1.407(3) ?
C6 C7 . 1.378(3) ?
C7 C7A . 1.396(3) ?
C8 C16 . 1.357(3) y
C8 C9 . 1.470(3) y
C9 O2 . 1.210(3) ?
C9 O1 . 1.365(3) y
C10 O1 . 1.379(2) y
C10 C11 . 1.385(3) ?
C10 C15 . 1.401(3) ?
C11 C12 . 1.388(3) ?
C12 C13 . 1.405(3) ?
C13 C14 . 1.377(3) ?
C14 C15 . 1.409(3) ?
C15 C16 . 1.434(3) y
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C16 H16 . 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
C14 H14 O1 4_575 0.95 2.46 3.383(3) 162.9 yes
C11 H11 N3 4_676 0.95 2.63 3.523(3) 156.2 yes
C13 H13 O2 4_675 0.95 2.65 3.314(3) 127.3 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
C7A S1 C2 N3 . . . . 1.07(17) ?
C7A S1 C2 C8 . . . . -178.49(18) ?
C8 C2 N3 C3A . . . . 179.04(18) ?
S1 C2 N3 C3A . . . . -0.5(2) ?
C2 N3 C3A C4 . . . . 179.1(2) ?
C2 N3 C3A C7A . . . . -0.5(3) ?
N3 C3A C4 C5 . . . . -179.1(2) ?
C7A C3A C4 C5 . . . . 0.5(3) ?
C3A C4 C5 C6 . . . . -1.1(3) ?
C4 C5 C6 C7 . . . . 0.6(3) ?
C5 C6 C7 C7A . . . . 0.4(3) ?
C6 C7 C7A C3A . . . . -1.0(3) ?
C6 C7 C7A S1 . . . . 177.72(17) ?
N3 C3A C7A C7 . . . . -179.79(19) ?
C4 C3A C7A C7 . . . . 0.6(3) ?
N3 C3A C7A S1 . . . . 1.3(2) ?
C4 C3A C7A S1 . . . . -178.36(16) ?
C2 S1 C7A C7 . . . . 179.9(2) ?
C2 S1 C7A C3A . . . . -1.24(16) ?
N3 C2 C8 C16 . . . . -5.4(3) ?
S1 C2 C8 C16 . . . . 174.10(16) ?
N3 C2 C8 C9 . . . . 174.66(19) ?
S1 C2 C8 C9 . . . . -5.8(3) ?
C16 C8 C9 O2 . . . . 179.9(2) ?
C2 C8 C9 O2 . . . . -0.2(3) ?
C16 C8 C9 O1 . . . . 0.2(3) ?
C2 C8 C9 O1 . . . . -179.90(17) ?
O1 C10 C11 C12 . . . . -178.97(18) ?
C15 C10 C11 C12 . . . . 0.4(3) ?
C10 C11 C12 C13 . . . . -0.9(3) ?
C11 C12 C13 C14 . . . . 0.7(3) ?
C12 C13 C14 C15 . . . . 0.1(3) ?
O1 C10 C15 C14 . . . . 179.76(18) ?
C11 C10 C15 C14 . . . . 0.5(3) ?
O1 C10 C15 C16 . . . . -1.3(3) ?
C11 C10 C15 C16 . . . . 179.42(19) ?
C13 C14 C15 C10 . . . . -0.7(3) ?
C13 C14 C15 C16 . . . . -179.6(2) ?
C2 C8 C16 C15 . . . . -179.62(19) ?
C9 C8 C16 C15 . . . . 0.3(3) ?
C10 C15 C16 C8 . . . . 0.2(3) ?
C14 C15 C16 C8 . . . . 179.1(2) ?
O2 C9 O1 C10 . . . . 179.04(18) ?
C8 C9 O1 C10 . . . . -1.2(3) ?
C11 C10 O1 C9 . . . . -178.83(18) ?
C15 C10 O1 C9 . . . . 1.8(3) ?

_cod_database_fobs_code 1566729
