#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/14/2231472.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_2231472
loop_
_publ_author_name
'Wang, Xiang-hui'
'Yang, Jian-xin'
'You, Cheng-hang'
'Lin, Qiang'
_publ_section_title
;
 Propyl 3-oxo-2,3-dihydro-1,2-benzothiazole-2-carboxylate
;
_journal_coeditor_code           FL2349
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2237
_journal_paper_doi               10.1107/S1600536811028613
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H11 N O3 S'
_chemical_formula_moiety         'C11 H11 N O3 S'
_chemical_formula_sum            'C11 H11 N O3 S'
_chemical_formula_weight         237.27
_chemical_name_systematic
;
Propyl 3-oxo-2,3-dihydro-1,2-benzothiazole-2-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.720(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.235(7)
_cell_length_b                   5.123(2)
_cell_length_c                   12.791(6)
_cell_measurement_reflns_used    3253
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.121
_cell_measurement_theta_min      2.989
_cell_volume                     1063.8(8)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8491
_diffrn_reflns_theta_full        29.07
_diffrn_reflns_theta_max         29.07
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.9432
_exptl_absorpt_correction_T_min  0.9040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Pink
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0388
_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)+(0.0506P)²+0.3160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                2224
_reflns_number_total             2766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fl2349.cif
_cod_data_source_block           I
_cod_original_cell_volume        1063.7(8)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               2231472
_cod_database_fobs_code          2231472
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.25453(2) 0.70918(8) 0.71855(3) 0.02263(12) Uani d . 1 1
O O1 0.16642(7) 0.7439(2) 0.43840(8) 0.0285(3) Uani d . 1 1
O O2 0.28813(7) 1.0985(2) 0.46620(9) 0.0289(3) Uani d . 1 1
O O3 0.34796(8) 1.1023(3) 0.62778(10) 0.0339(3) Uani d . 1 1
N N1 0.24529(8) 0.8149(3) 0.59025(10) 0.0210(3) Uani d . 1 1
C C1 0.17595(9) 0.4842(3) 0.69666(11) 0.0195(3) Uani d . 1 1
C C2 0.14578(10) 0.3037(3) 0.76888(12) 0.0227(3) Uani d . 1 1
H H2 0.1671 0.2966 0.8383 0.027 Uiso calc R 1 1
C C3 0.08395(10) 0.1360(3) 0.73593(13) 0.0256(3) Uani d . 1 1
H H3 0.0628 0.0116 0.7837 0.031 Uiso calc R 1 1
C C4 0.05157(10) 0.1449(3) 0.63348(13) 0.0258(3) Uani d . 1 1
H H4 0.0088 0.0285 0.6130 0.031 Uiso calc R 1 1
C C5 0.08200(9) 0.3230(3) 0.56251(12) 0.0226(3) Uani d . 1 1
H H5 0.0608 0.3292 0.4930 0.027 Uiso calc R 1 1
C C6 0.14445(9) 0.4939(3) 0.59480(11) 0.0189(3) Uani d . 1 1
C C7 0.18296(9) 0.6918(3) 0.52901(12) 0.0203(3) Uani d . 1 1
C C8 0.29898(9) 1.0187(3) 0.56431(12) 0.0231(3) Uani d . 1 1
C C9 0.34321(10) 1.3087(3) 0.43295(15) 0.0304(4) Uani d . 1 1
H H9A 0.3533 1.4290 0.4923 0.036 Uiso calc R 1 1
H H9B 0.3163 1.4093 0.3760 0.036 Uiso calc R 1 1
C C10 0.42408(10) 1.2039(4) 0.39541(14) 0.0295(4) Uani d . 1 1
H H10A 0.4139 1.0737 0.3395 0.035 Uiso calc R 1 1
H H10B 0.4532 1.1151 0.4539 0.035 Uiso calc R 1 1
C C11 0.47784(11) 1.4220(4) 0.35365(15) 0.0357(4) Uani d . 1 1
H H11A 0.4520 1.4964 0.2907 0.043 Uiso calc R 1 1
H H11B 0.5322 1.3520 0.3364 0.043 Uiso calc R 1 1
H H11C 0.4840 1.5583 0.4070 0.043 Uiso calc R 1 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
N1 S1 C1 90.00(7)
C8 O2 C9 115.18(13)
C8 N1 C7 129.86(13)
C8 N1 S1 114.20(10)
C7 N1 S1 115.87(11)
C6 C1 C2 120.86(14)
C6 C1 S1 112.73(12)
C2 C1 S1 126.40(12)
C3 C2 C1 117.89(14)
C3 C2 H2 121.1
C1 C2 H2 121.1
C2 C3 C4 121.68(15)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 120.04(15)
C5 C4 H4 120.0
C3 C4 H4 120.0
C4 C5 C6 118.88(15)
C4 C5 H5 120.6
C6 C5 H5 120.6
C1 C6 C5 120.65(14)
C1 C6 C7 114.07(13)
C5 C6 C7 125.28(14)
O1 C7 N1 125.15(15)
O1 C7 C6 127.56(14)
N1 C7 C6 107.29(12)
O3 C8 O2 127.15(15)
O3 C8 N1 120.72(15)
O2 C8 N1 112.13(13)
O2 C9 C10 111.65(14)
O2 C9 H9A 109.3
C10 C9 H9A 109.3
O2 C9 H9B 109.3
C10 C9 H9B 109.3
H9A C9 H9B 108.0
C9 C10 C11 110.97(16)
C9 C10 H10A 109.4
C11 C10 H10A 109.4
C9 C10 H10B 109.4
C11 C10 H10B 109.4
H10A C10 H10B 108.0
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N1 1.7328(15)
S1 C1 1.7393(17)
O1 C7 1.2162(19)
O2 C8 1.329(2)
O2 C9 1.466(2)
O3 C8 1.208(2)
N1 C8 1.403(2)
N1 C7 1.4195(19)
C1 C6 1.395(2)
C1 C2 1.400(2)
C2 C3 1.383(2)
C2 H2 0.9500
C3 C4 1.407(2)
C3 H3 0.9500
C4 C5 1.383(2)
C4 H4 0.9500
C5 C6 1.398(2)
C5 H5 0.9500
C6 C7 1.463(2)
C9 C10 1.503(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.519(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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
C2 H2 O2 4_576 0.95 2.60 3.437(3) 148
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
C1 S1 N1 C8 178.88(12)
C1 S1 N1 C7 1.45(12)
N1 S1 C1 C6 -0.32(12)
N1 S1 C1 C2 178.34(14)
C6 C1 C2 C3 0.0(2)
S1 C1 C2 C3 -178.55(12)
C1 C2 C3 C4 -0.3(2)
C2 C3 C4 C5 0.6(2)
C3 C4 C5 C6 -0.6(2)
C2 C1 C6 C5 -0.1(2)
S1 C1 C6 C5 178.67(12)
C2 C1 C6 C7 -179.57(14)
S1 C1 C6 C7 -0.82(17)
C4 C5 C6 C1 0.4(2)
C4 C5 C6 C7 179.80(14)
C8 N1 C7 O1 1.5(3)
S1 N1 C7 O1 178.47(13)
C8 N1 C7 C6 -179.01(14)
S1 N1 C7 C6 -2.07(16)
C1 C6 C7 O1 -178.77(16)
C5 C6 C7 O1 1.8(3)
C1 C6 C7 N1 1.79(18)
C5 C6 C7 N1 -177.67(14)
C9 O2 C8 O3 0.9(2)
C9 O2 C8 N1 -179.00(13)
C7 N1 C8 O3 178.88(15)
S1 N1 C8 O3 1.9(2)
C7 N1 C8 O2 -1.2(2)
S1 N1 C8 O2 -178.19(10)
C8 O2 C9 C10 85.16(18)
O2 C9 C10 C11 175.72(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656926
