##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2011-01-21
_journal_date_accepted     2011-02-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      3
_journal_page_first     o620
_journal_page_last     o620
_journal_paper_category     QO
_journal_coeditor_code     FJ2389
_publ_contact_author_name
;
Marijana Đaković
;
_publ_contact_author_address
;     Laboratory of General and Inorganic Chemistry
      Department of Chemistry
      Faculty of Science, University of Zagreb
      Horvatovac 102a
      HR-10 000 Zagreb, Croatia
;
_publ_contact_author_email     mdjakovic@chem.pmf.hr
_publ_contact_author_fax     '00385 1 4606341'
_publ_contact_author_phone     '00385 1 4606356'
_publ_section_title
;
6-Iodo-2-methyl-1,3-benzothiazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Đaković, Marijana'
;
Department of Chemistry
Faculty of Science
University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
    'Čičak, Helena'
;
Department of Chemistry
Faculty of Science
University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
data_I
_chemical_name_systematic
;
6-Iodo-2-methyl-1,3-benzothiazole
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C8 H6 I N S'
_chemical_formula_sum     'C8 H6 I N S'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C8 H6 I N S'
_chemical_formula_weight     275.11
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,1/2+y,1/2-z
    3 -x,-y,-z
    4 1/2+x,1/2-y,1/2+z
_cell_length_a     8.3255(3)
_cell_length_b     7.6967(3)
_cell_length_c     13.8083(5)
_cell_angle_alpha     90
_cell_angle_beta     90.686(4)
_cell_angle_gamma     90
_cell_volume     884.76(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10010
_cell_measurement_theta_min     4.4194
_cell_measurement_theta_max     32.6091
_cell_measurement_temperature     296
_cell_special_details
;
;
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.47
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.14
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     2.065
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     3.787
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.253
_exptl_absorpt_correction_T_max     0.658
_exptl_special_details
;
Solvent used: CH₂Cl₂ Crystal mount: glued on a glass fibre Mosaicity (°):
1.1(1) Frames collected: 892 Seconds exposure per frame: 5 Degree rotation per
frame: 1.0 Crystal-Detector distance (mm): 50.0.
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Saphire-3 CCD detector
;
_diffrn_measurement_method     'CCD'
_diffrn_detector_area_resol_mean     16.3426
_diffrn_reflns_number     13190
_diffrn_reflns_av_R_equivalents     0.0268
_diffrn_reflns_av_sigmaI/netI     0.0125
_diffrn_reflns_theta_min     4.64
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_reflns_reduction_process
;
;
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger.
;
_reflns_number_total     1928
_reflns_number_gt     1729
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0273
_refine_ls_R_factor_gt     0.0235
_refine_ls_wR_factor_gt     0.0623
_refine_ls_wR_factor_ref     0.0640
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_restrained_S_all     1.063
_refine_ls_number_reflns     1928
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0397P)²+0.4162P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.837
_refine_diff_density_min     -0.723
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    S S 0.1246 0.1234 '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'
    I I -0.4742 1.8119 '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'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    I I1 0.96733(2) 0.14994(3) 0.306240(10)
                                          0.04850(10)
                                                    Uani . . 1.000
    S S1 0.66879(11) 0.75187(9) 0.49021(6) 0.0518(3) Uani . . 1.000
    N N1 0.6453(3) 0.5615(3) 0.64355(18) 0.0447(8) Uani . . 1.000
    C C1 0.6117(4) 0.7135(4) 0.6097(2) 0.0457(9) Uani . . 1.000
    C C2 0.7440(3) 0.5425(3) 0.4842(2) 0.0392(8) Uani . . 1.000
    C C3 0.8155(3) 0.4585(4) 0.40718(19) 0.0430(8) Uani . . 1.000
    C C4 0.8633(3) 0.2887(4) 0.42068(19) 0.0399(8) Uani . . 1.000
    C C5 0.8427(4) 0.2058(4) 0.5097(2) 0.0452(9) Uani . . 1.000
    C C6 0.7728(4) 0.2900(4) 0.5857(2) 0.0467(9) Uani . . 1.000
    C C7 0.7211(3) 0.4614(3) 0.5734(2) 0.0386(7) Uani . . 1.000
    C C8 0.5343(5) 0.8546(4) 0.6669(3) 0.0600(11) Uani . . 1.000
    H H3 0.83070 0.51470 0.34840 0.0520 Uiso calc R 1.000
    H H5 0.87710 0.09160 0.51740 0.0540 Uiso calc R 1.000
    H H6 0.75980 0.23380 0.64480 0.0560 Uiso calc R 1.000
    H H8A 0.46780 0.80420 0.71580 0.0900 Uiso calc R 1.000
    H H8B 0.46950 0.92540 0.62460 0.0900 Uiso calc R 1.000
    H H8C 0.61580 0.92510 0.69710 0.0900 Uiso calc R 1.000
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    I1 0.04880(10)
                 0.0567(2) 0.04020(10)
                                     0.00120(10)
                                               0.00480(10)
                                                         -0.00550(10)
    S1 0.0658(5) 0.0376(4) 0.0518(4) 0.0063(3) -0.0035(3) 0.0058(3)
    N1 0.0487(13) 0.0419(13) 0.0437(13) -0.0022(10) 0.0082(10) -0.0014(10)
    C1 0.0416(14) 0.0411(14) 0.0543(17) -0.0019(12) -0.0027(12) -0.0054(12)
    C2 0.0424(14) 0.0345(12) 0.0407(13) -0.0029(11) -0.0035(11) 0.0049(11)
    C3 0.0482(15) 0.0457(14) 0.0351(13) -0.0040(12) -0.0001(11) 0.0075(12)
    C4 0.0393(14) 0.0457(14) 0.0347(13) -0.0025(11) 0.0025(11) -0.0027(11)
    C5 0.0536(16) 0.0347(13) 0.0474(16) 0.0044(12) 0.0043(13) 0.0030(11)
    C6 0.0593(18) 0.0394(13) 0.0415(15) -0.0005(13) 0.0114(13) 0.0073(12)
    C7 0.0396(13) 0.0364(12) 0.0399(13) -0.0035(11) 0.0037(10) 0.0013(10)
    C8 0.062(2) 0.0511(19) 0.067(2) 0.0089(15) -0.0004(17) -0.0108(15)
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C4 . . 2.103(3) no
    S1 C1 . . 1.748(3) no
    S1 C2 . . 1.731(2) no
    N1 C1 . . 1.289(4) no
    N1 C7 . . 1.395(4) no
    C1 C8 . . 1.494(5) no
    C2 C3 . . 1.385(4) no
    C2 C7 . . 1.396(4) no
    C3 C4 . . 1.378(4) no
    C4 C5 . . 1.397(4) no
    C5 C6 . . 1.369(4) no
    C6 C7 . . 1.397(4) no
    C3 H3 . . 0.9300 no
    C5 H5 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C8 H8A . . 0.9600 no
    C8 H8B . . 0.9600 no
    C8 H8C . . 0.9600 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    I1 C1 3.826(3) . 3_766 no
    I1 N1 3.158(2) . 4_554 no
    I1 H5 3.3100 . 3_756 no
    S1 H5 3.1600 . 1_565 no
    S1 H8B 3.1600 . 3_676 no
    N1 I1 3.158(2) . 4_455 no
    C1 I1 3.826(3) . 3_766 no
    H3 H8A 2.5800 . 4_564 no
    H5 S1 3.1600 . 1_545 no
    H5 I1 3.3100 . 3_756 no
    H5 H5 2.5400 . 3_756 no
    H8A H3 2.5800 . 4_465 no
    H8B S1 3.1600 . 3_676 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 S1 C2 . . . 89.46(14) no
    C1 N1 C7 . . . 110.3(2) no
    S1 C1 N1 . . . 115.8(2) no
    S1 C1 C8 . . . 120.0(2) no
    N1 C1 C8 . . . 124.1(3) no
    S1 C2 C3 . . . 129.1(2) no
    S1 C2 C7 . . . 108.70(19) no
    C3 C2 C7 . . . 122.2(2) no
    C2 C3 C4 . . . 117.7(2) no
    I1 C4 C3 . . . 120.06(19) no
    I1 C4 C5 . . . 119.0(2) no
    C3 C4 C5 . . . 120.9(3) no
    C4 C5 C6 . . . 121.1(3) no
    C5 C6 C7 . . . 119.1(3) no
    N1 C7 C2 . . . 115.7(2) no
    N1 C7 C6 . . . 125.3(2) no
    C2 C7 C6 . . . 119.0(2) no
    C2 C3 H3 . . . 121.00 no
    C4 C3 H3 . . . 121.00 no
    C4 C5 H5 . . . 119.00 no
    C6 C5 H5 . . . 120.00 no
    C5 C6 H6 . . . 120.00 no
    C7 C6 H6 . . . 120.00 no
    C1 C8 H8A . . . 110.00 no
    C1 C8 H8B . . . 110.00 no
    C1 C8 H8C . . . 109.00 no
    H8A C8 H8B . . . 109.00 no
    H8A C8 H8C . . . 109.00 no
    H8B C8 H8C . . . 109.00 no
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
    C2 S1 C1 N1 . . . . 0.5(3) no
    C2 S1 C1 C8 . . . . 178.5(3) no
    C1 S1 C2 C3 . . . . 179.0(3) no
    C1 S1 C2 C7 . . . . -0.6(2) no
    C7 N1 C1 S1 . . . . -0.3(3) no
    C7 N1 C1 C8 . . . . -178.2(3) no
    C1 N1 C7 C2 . . . . -0.2(3) no
    C1 N1 C7 C6 . . . . -179.6(3) no
    S1 C2 C3 C4 . . . . -179.0(2) no
    C7 C2 C3 C4 . . . . 0.6(4) no
    S1 C2 C7 N1 . . . . 0.5(3) no
    S1 C2 C7 C6 . . . . 180.0(2) no
    C3 C2 C7 N1 . . . . -179.1(2) no
    C3 C2 C7 C6 . . . . 0.4(4) no
    C2 C3 C4 I1 . . . . 178.41(19) no
    C2 C3 C4 C5 . . . . -1.1(4) no
    I1 C4 C5 C6 . . . . -178.8(2) no
    C3 C4 C5 C6 . . . . 0.8(5) no
    C4 C5 C6 C7 . . . . 0.2(5) no
    C5 C6 C7 N1 . . . . 178.6(3) no
    C5 C6 C7 C2 . . . . -0.8(4) no
