#------------------------------------------------------------------------------
#$Date: 2009-11-16 03:43:51 +0200 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/1100672.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1100672
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_[local]_cod_cif_authors_sg_H-M  P21/a
loop_
_publ_author_name
'SEKINE,Akiko '
'JOMOTO,Kohei '
'UEKUSA,Hidehiro '
'OHASHI,Yuji '
'YAGI,Minoru '
_journal_name_full 'Analytical Sciences: X-ray Structure Analysis Online'
_exptl_crystal_preparation
;
recrystallized from methanol solution
;
_chemical_name_systematic
;
5-chloro-2-methyl-4-isothiazoline-3-one 4,4'-ethane-1,1-diyldiphenol
;
_chemical_name_common
;
5-chloro-2-methyl-4-isothiazoline-3-one and 4,4'-ethylidenebisphenol
;
_chemical_formula_sum    'C18 H18 Cl N O3 S'
_chemical_formula_weight          363.84
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'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting            monoclinic
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z'
_cell_length_a                    16.152(6)
_cell_length_b                    10.127(5)
_cell_length_c                    11.450(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  105.48(3)
_cell_angle_gamma                 90.00
_cell_volume                      1805.0(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     25
_cell_measurement_theta_min       25.0
_cell_measurement_theta_max       30.0
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.3
_exptl_crystal_size_mid           0.4
_exptl_crystal_size_min           0.5
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.339
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              760
_exptl_absorpt_coefficient_mu     0.342
_exptl_absorpt_correction_type    PSI-SCAN
_exptl_absorpt_correction_T_min   0.9392
_exptl_absorpt_correction_T_max   0.9713
_exptl_absorpt_process_details    'North'
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Rigaku Rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   AFC5R
_diffrn_measurement_method        '\w-2\q scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          150
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         -0.1
_diffrn_reflns_number             4293
_diffrn_reflns_av_R_equivalents   0.0361
_diffrn_reflns_av_sigmaI/netI     0.0523
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        20
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          1.85
_diffrn_reflns_theta_max          27.49
_reflns_number_total              4144
_reflns_number_gt                 2436
_reflns_threshold_expression      >2sigma(I)
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.6064P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          4144
_refine_ls_number_parameters      229
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.1098
_refine_ls_R_factor_gt            0.0520
_refine_ls_wR_factor_ref          0.1460
_refine_ls_wR_factor_gt           0.1251
_refine_ls_goodness_of_fit_ref    1.028
_refine_ls_restrained_S_all       1.028
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl -0.00655(6) -0.30885(12) 0.36005(10) 0.0998(4) Uani 1 1 d . . .
S1 S 0.10699(5) -0.14801(8) 0.55241(8) 0.0631(2) Uani 1 1 d . . .
O1 O 0.21510(12) 0.05755(19) 1.30116(15) 0.0550(5) Uani 1 1 d . . .
H1O H 0.1636 0.0745 1.2828 0.083 Uiso 1 1 calc R . .
O2 O 0.29736(12) -0.07594(18) 0.51068(15) 0.0521(5) Uani 1 1 d . . .
H2O H 0.2745 -0.0324 0.4503 0.078 Uiso 1 1 calc R . .
O3 O -0.04798(13) -0.0823(3) 0.73878(18) 0.0769(7) Uani 1 1 d . . .
N1 N 0.06996(13) -0.0874(2) 0.6661(2) 0.0548(6) Uani 1 1 d . . .
C1 C 0.34221(17) 0.1568(3) 0.8211(2) 0.0490(6) Uani 1 1 d D . .
C2 C 0.30207(18) 0.2079(3) 0.7098(2) 0.0510(6) Uani 1 1 d . A .
H2 H 0.2855 0.2961 0.7042 0.061 Uiso 1 1 calc R . .
C3 C 0.28537(15) 0.1329(2) 0.6058(2) 0.0436(6) Uani 1 1 d . . .
H3 H 0.2572 0.1702 0.5317 0.052 Uiso 1 1 calc R A .
C4 C 0.31048(15) 0.0026(2) 0.6117(2) 0.0401(5) Uani 1 1 d . A .
C5 C 0.34969(18) -0.0532(3) 0.7229(2) 0.0524(7) Uani 1 1 d . . .
H5 H 0.3652 -0.1419 0.7282 0.063 Uiso 1 1 calc R A .
C6 C 0.36572(19) 0.0242(3) 0.8262(2) 0.0569(7) Uani 1 1 d . A .
H6 H 0.3928 -0.0133 0.9008 0.068 Uiso 1 1 calc R . .
C8 C 0.32621(19) 0.1898(3) 1.0328(2) 0.0523(7) Uani 1 1 d D . .
C9 C 0.37425(18) 0.1298(3) 1.1374(3) 0.0610(8) Uani 1 1 d . A .
H9 H 0.4331 0.1191 1.1488 0.073 Uiso 1 1 calc R . .
C10 C 0.33653(17) 0.0849(3) 1.2261(2) 0.0562(7) Uani 1 1 d . . .
H10 H 0.3701 0.0449 1.2959 0.067 Uiso 1 1 calc R A .
C11 C 0.24998(16) 0.0999(2) 1.2105(2) 0.0424(6) Uani 1 1 d . A .
C12 C 0.20052(17) 0.1589(3) 1.1057(2) 0.0508(6) Uani 1 1 d . . .
H12 H 0.1416 0.1688 1.0937 0.061 Uiso 1 1 calc R A .
C13 C 0.2393(2) 0.2027(3) 1.0195(2) 0.0588(7) Uani 1 1 d . A .
H13 H 0.2056 0.2426 0.9497 0.071 Uiso 1 1 calc R . .
C14 C 0.00907(18) -0.2208(3) 0.4914(3) 0.0602(7) Uani 1 1 d . . .
C15 C -0.04742(17) -0.1998(3) 0.5555(3) 0.0628(8) Uani 1 1 d . . .
H15 H -0.1031 -0.2333 0.5345 0.075 Uiso 1 1 calc R . .
C16 C -0.01287(17) -0.1195(3) 0.6610(3) 0.0561(7) Uani 1 1 d . . .
C17 C 0.1263(2) -0.0109(4) 0.7643(3) 0.0721(9) Uani 1 1 d . . .
H17A H 0.0924 0.0319 0.8105 0.108 Uiso 1 1 calc R . .
H17B H 0.1563 0.0544 0.7306 0.108 Uiso 1 1 calc R . .
H17C H 0.1670 -0.0689 0.8161 0.108 Uiso 1 1 calc R . .
C7 C 0.3603(3) 0.2495(4) 0.9306(3) 0.0501(10) Uani 0.834(8) 1 d PD A 1
H7 H 0.3305 0.3332 0.9053 0.060 Uiso 0.834(8) 1 calc PR A 1
C18 C 0.4571(3) 0.2767(6) 0.9717(3) 0.0762(17) Uani 0.834(8) 1 d PD A 1
H18A H 0.4698 0.3311 1.0429 0.114 Uiso 0.834(8) 1 calc PR A 1
H18B H 0.4744 0.3215 0.9082 0.114 Uiso 0.834(8) 1 calc PR A 1
H18C H 0.4876 0.1947 0.9896 0.114 Uiso 0.834(8) 1 calc PR A 1
C7B C 0.3890(4) 0.2007(18) 0.9518(5) 0.054(6) Uiso 0.166(8) 1 d PD A 2
H7B H 0.4412 0.1487 0.9847 0.064 Uiso 0.166(8) 1 calc PR A 2
C18B C 0.4087(15) 0.3474(17) 0.9526(18) 0.068(6) Uiso 0.166(8) 1 d PD A 2
H18D H 0.3559 0.3965 0.9332 0.102 Uiso 0.166(8) 1 calc PR A 2
H18E H 0.4396 0.3659 0.8936 0.102 Uiso 0.166(8) 1 calc PR A 2
H18F H 0.4430 0.3727 1.0315 0.102 Uiso 0.166(8) 1 calc PR A 2
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
Cl1 0.0796(6) 0.1207(9) 0.1028(8) -0.0361(6) 0.0308(5) -0.0092(6)
S1 0.0447(4) 0.0727(5) 0.0791(5) 0.0022(4) 0.0293(4) -0.0031(4)
O1 0.0528(11) 0.0746(13) 0.0401(10) 0.0089(9) 0.0166(8) 0.0050(9)
O2 0.0670(12) 0.0521(11) 0.0368(9) -0.0045(8) 0.0130(8) 0.0010(9)
O3 0.0510(11) 0.128(2) 0.0586(13) 0.0093(13) 0.0263(10) 0.0033(12)
N1 0.0415(12) 0.0650(15) 0.0609(14) 0.0075(12) 0.0186(10) -0.0024(11)
C1 0.0590(15) 0.0537(16) 0.0397(13) -0.0061(12) 0.0227(12) -0.0159(13)
C2 0.0654(17) 0.0418(14) 0.0507(15) -0.0010(12) 0.0243(13) -0.0059(13)
C3 0.0470(13) 0.0448(14) 0.0397(13) 0.0057(11) 0.0125(11) -0.0020(11)
C4 0.0415(12) 0.0460(14) 0.0352(12) -0.0015(11) 0.0143(10) -0.0059(11)
C5 0.0686(18) 0.0474(15) 0.0412(14) 0.0061(12) 0.0149(12) 0.0075(13)
C6 0.0674(18) 0.0684(19) 0.0325(13) 0.0077(13) 0.0094(12) 0.0002(15)
C8 0.0638(17) 0.0579(17) 0.0378(13) -0.0140(12) 0.0178(12) -0.0146(14)
C9 0.0485(15) 0.076(2) 0.0622(18) -0.0057(16) 0.0217(14) -0.0027(15)
C10 0.0508(15) 0.0707(19) 0.0467(15) 0.0065(14) 0.0125(12) 0.0106(14)
C11 0.0507(14) 0.0453(14) 0.0326(12) -0.0047(10) 0.0137(11) 0.0017(11)
C12 0.0472(14) 0.0664(18) 0.0376(13) -0.0019(13) 0.0091(11) 0.0032(13)
C13 0.0687(19) 0.0713(19) 0.0332(13) 0.0033(13) 0.0080(12) -0.0034(15)
C14 0.0488(16) 0.0638(19) 0.0692(18) 0.0037(15) 0.0181(14) -0.0001(14)
C15 0.0377(14) 0.084(2) 0.0664(19) 0.0127(17) 0.0122(13) -0.0022(14)
C16 0.0409(14) 0.077(2) 0.0529(16) 0.0204(15) 0.0164(12) 0.0038(13)
C17 0.0602(19) 0.081(2) 0.076(2) -0.0005(18) 0.0194(16) -0.0128(17)
C7 0.060(2) 0.053(2) 0.0400(17) -0.0041(15) 0.0165(15) -0.009(2)
C18 0.070(3) 0.114(4) 0.049(2) -0.023(2) 0.0237(19) -0.041(3)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl1 C14 1.708(3) . y
S1 N1 1.687(2) . y
S1 C14 1.716(3) . y
O1 C11 1.375(3) . ?
O2 C4 1.373(3) . ?
O3 C16 1.236(3) . y
N1 C16 1.363(3) . y
N1 C17 1.465(4) . y
C1 C2 1.368(4) . ?
C1 C6 1.392(4) . ?
C1 C7B 1.5504(12) . ?
C1 C7 1.531(4) . ?
C2 C3 1.377(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.385(4) . ?
C8 C13 1.377(4) . ?
C8 C9 1.382(4) . ?
C8 C7B 1.5503(11) . ?
C8 C7 1.544(4) . ?
C9 C10 1.392(4) . ?
C10 C11 1.370(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.376(4) . ?
C14 C15 1.333(4) . y
C15 C16 1.438(4) . y
C7 C18 1.532(5) . ?
C7B C18B 1.520(17) . ?
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
N1 S1 C14 89.58(13) . . y
C16 N1 C17 124.2(2) . . y
C16 N1 S1 115.2(2) . . y
C17 N1 S1 120.61(18) . . y
C2 C1 C6 117.4(2) . . ?
C2 C1 C7B 141.1(8) . . ?
C6 C1 C7B 100.3(7) . . ?
C2 C1 C7 118.1(3) . . ?
C6 C1 C7 124.5(3) . . ?
C7B C1 C7 25.4(6) . . ?
C1 C2 C3 122.1(3) . . ?
C4 C3 C2 119.9(2) . . ?
O2 C4 C3 122.4(2) . . ?
O2 C4 C5 118.0(2) . . ?
C3 C4 C5 119.6(2) . . ?
C4 C5 C6 119.4(3) . . ?
C5 C6 C1 121.5(2) . . ?
C13 C8 C9 117.3(2) . . ?
C13 C8 C7B 137.5(5) . . ?
C9 C8 C7B 104.1(6) . . ?
C13 C8 C7 116.0(3) . . ?
C9 C8 C7 126.7(3) . . ?
C7B C8 C7 25.3(6) . . ?
C8 C9 C10 121.5(3) . . ?
C11 C10 C9 119.9(3) . . ?
C10 C11 O1 118.4(2) . . ?
C10 C11 C12 119.5(2) . . ?
O1 C11 C12 122.0(2) . . ?
C13 C12 C11 119.5(3) . . ?
C12 C13 C8 122.4(3) . . ?
C15 C14 Cl1 127.4(2) . . y
C15 C14 S1 113.5(3) . . y
Cl1 C14 S1 119.11(17) . . y
C14 C15 C16 112.6(3) . . y
O3 C16 N1 122.0(3) . . y
O3 C16 C15 128.8(3) . . y
N1 C16 C15 109.2(2) . . y
C18 C7 C1 108.5(3) . . ?
C18 C7 C8 112.3(3) . . ?
C1 C7 C8 110.6(2) . . ?
C8 C7B C1 109.2(2) . . ?
C8 C7B C18B 103.6(12) . . ?
C1 C7B C18B 109.5(13) . . ?
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
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C14 S1 N1 C16 0.2(2) . . . . ?
C14 S1 N1 C17 177.7(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C7B C1 C2 C3 164.1(4) . . . . ?
C7 C1 C2 C3 178.1(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 O2 -178.4(2) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
O2 C4 C5 C6 178.5(2) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C7B C1 C6 C5 -169.7(3) . . . . ?
C7 C1 C6 C5 -177.9(3) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
C7B C8 C9 C10 -170.4(6) . . . . ?
C7 C8 C9 C10 176.9(3) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C9 C10 C11 O1 -178.4(3) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
O1 C11 C12 C13 178.1(2) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C9 C8 C13 C12 0.2(4) . . . . ?
C7B C8 C13 C12 165.7(9) . . . . ?
C7 C8 C13 C12 -177.4(3) . . . . ?
N1 S1 C14 C15 -0.4(3) . . . . ?
N1 S1 C14 Cl1 179.4(2) . . . . ?
Cl1 C14 C15 C16 -179.3(2) . . . . ?
S1 C14 C15 C16 0.5(4) . . . . ?
C17 N1 C16 O3 2.2(5) . . . . ?
S1 N1 C16 O3 179.6(2) . . . . ?
C17 N1 C16 C15 -177.4(3) . . . . ?
S1 N1 C16 C15 0.0(3) . . . . ?
C14 C15 C16 O3 -179.8(3) . . . . ?
C14 C15 C16 N1 -0.3(4) . . . . ?
C2 C1 C7 C18 -108.0(4) . . . . ?
C6 C1 C7 C18 70.2(4) . . . . ?
C7B C1 C7 C18 51.1(8) . . . . ?
C2 C1 C7 C8 128.4(3) . . . . ?
C6 C1 C7 C8 -53.3(4) . . . . ?
C7B C1 C7 C8 -72.5(6) . . . . ?
C13 C8 C7 C18 159.1(4) . . . . ?
C9 C8 C7 C18 -18.3(5) . . . . ?
C7B C8 C7 C18 -48.3(8) . . . . ?
C13 C8 C7 C1 -79.5(4) . . . . ?
C9 C8 C7 C1 103.1(4) . . . . ?
C7B C8 C7 C1 73.1(6) . . . . ?
C13 C8 C7B C1 -31.8(17) . . . . ?
C9 C8 C7B C1 134.9(9) . . . . ?
C7 C8 C7B C1 -69.5(6) . . . . ?
C13 C8 C7B C18B 84.7(9) . . . . ?
C9 C8 C7B C18B -108.5(11) . . . . ?
C7 C8 C7B C18B 47.1(14) . . . . ?
C2 C1 C7B C8 100.2(9) . . . . ?
C6 C1 C7B C8 -93.9(10) . . . . ?
C7 C1 C7B C8 70.2(6) . . . . ?
C2 C1 C7B C18B -12.5(13) . . . . ?
C6 C1 C7B C18B 153.4(11) . . . . ?
C7 C1 C7B C18B -42.5(15) . . . . ?
_diffrn_measured_fraction_theta_max    1.000
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   1.000
_refine_diff_density_max    0.305
_refine_diff_density_min   -0.401
_refine_diff_density_rms    0.047