##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4
_chemical_name_systematic
;
4-{5-[(2-Bromobenzyl)sulfanyl]-1H-tetrazol-1-yl}benzoic acid
;
_chemical_formula_moiety     'C15 H11 Br1 N4 O2 S1'
_chemical_formula_sum     'C15 H11 Br N4 O2 S'
_chemical_formula_iupac     'C15 H11 Br N4 O2 S'
_chemical_formula_weight     391.25
_symmetry_space_group_name_Hall     '-P 2yn'
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.4570(5)
_cell_length_b     8.3500(5)
_cell_length_c     25.3680(14)
_cell_angle_alpha     90
_cell_angle_beta     97.626(3)
_cell_angle_gamma     90
_cell_volume     1565.59(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3980
_cell_measurement_theta_min     11.97
_cell_measurement_theta_max     18.06
_cell_measurement_temperature     290(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.1
_exptl_crystal_size_mid     0.1
_exptl_crystal_size_min     0.1
_exptl_crystal_size_rad     0.1
_exptl_crystal_density_diffrn     1.66
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     784
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    0 0 1 0.26
    0 0 -1 0.266
    0 1 0 0.131
    0 -1 0 0.096
    1 0 0 0.16
    -1 0 0 0.146
    1 0 8 0.235
    0 4 -3 0.103
    0 -3 -2 0.086
    0 7 6 0.147
    0 1 4 0.215
    -1 -14 15 0.144
_exptl_absorpt_coefficient_mu     2.773
_exptl_absorpt_correction_type     cylinder
_exptl_absorpt_process_details
;
(Dwiggins, 1975)
;
_exptl_absorpt_correction_T_min     0.6044
_exptl_absorpt_correction_T_max     0.6084
_exptl_special_details
;Absorption correction:
        interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
        for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
        p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
        The interpolation procedure of (Dwiggins, 1975)
        is used with some modification
;
_diffrn_ambient_temperature     290(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_device     '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method     CCD
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     24464
_diffrn_reflns_av_R_equivalents     0.0692
_diffrn_reflns_theta_min     2.93
_diffrn_reflns_theta_max     25.68
_diffrn_reflns_theta_full     25
_diffrn_measured_fraction_theta_max     0.974
_diffrn_measured_fraction_theta_full     0.972
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     30
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) 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     2889
_reflns_number_gt     2388
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0517
_refine_ls_R_factor_gt     0.0411
_refine_ls_wR_factor_gt     0.1076
_refine_ls_wR_factor_ref     0.1141
_refine_ls_goodness_of_fit_ref     1.06
_refine_ls_restrained_S_all     1.06
_refine_ls_number_reflns     2889
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0623P)²+0.5855P] 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
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.384
_refine_diff_density_min     -0.471
_refine_ls_extinction_method     none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    Br Br -0.2901 2.4595 '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 0.006 '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'
_computing_data_collection     'COLLECT (Nonius, 1999)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
 'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material     'WinGX (Farrugia, 2012)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.16110(5) -0.03469(5) 0.285194(14) 0.07850(19) Uani d . 1 1 . .
    S S1 0.11800(10) 0.09831(9) 0.14388(3) 0.0586(2) Uani d . 1 1 . .
    O O1 -0.4811(3) 0.7429(2) 0.08768(9) 0.0684(6) Uani d . 1 1 . .
    O O2 -0.7294(3) 0.5931(3) 0.06893(9) 0.0644(6) Uani d . 1 1 . .
    H H1 -0.769(6) 0.671(5) 0.0724(17) 0.097 Uiso d . 1 1 . .
    N N1 -0.1430(3) 0.0490(2) 0.05969(8) 0.0424(5) Uani d . 1 1 . .
    N N2 -0.1946(3) -0.0608(2) 0.02100(9) 0.0482(5) Uani d . 1 1 . .
    N N3 -0.0817(3) -0.1770(3) 0.02891(9) 0.0514(5) Uani d . 1 1 . .
    N N4 0.0451(3) -0.1480(2) 0.07213(8) 0.0484(5) Uani d . 1 1 . .
    C C1 -0.5529(4) 0.6156(3) 0.07638(10) 0.0506(6) Uani d . 1 1 . .
    C C2 -0.4489(3) 0.4647(3) 0.07046(10) 0.0462(6) Uani d . 1 1 . .
    C C3 -0.5338(3) 0.3184(3) 0.06132(11) 0.0515(6) Uani d . 1 1 . .
    H H3 -0.6594 0.3124 0.0577 0.062 Uiso calc R 1 1 . .
    C C4 -0.4328(3) 0.1809(3) 0.05749(10) 0.0496(6) Uani d . 1 1 . .
    H H4 -0.4891 0.0819 0.0515 0.059 Uiso calc R 1 1 . .
    C C5 -0.2460(3) 0.1937(3) 0.06285(9) 0.0421(5) Uani d . 1 1 . .
    C C6 -0.1586(3) 0.3385(3) 0.07012(11) 0.0495(6) Uani d . 1 1 . .
    H H6 -0.0334 0.3446 0.0722 0.059 Uiso calc R 1 1 . .
    C C7 -0.2614(4) 0.4750(3) 0.07421(11) 0.0507(6) Uani d . 1 1 . .
    H H7 -0.2048 0.5741 0.0795 0.061 Uiso calc R 1 1 . .
    C C8 0.0051(3) -0.0061(3) 0.09069(10) 0.0442(5) Uani d . 1 1 . .
    C C9 0.2832(4) -0.0542(4) 0.16947(12) 0.0618(8) Uani d . 1 1 . .
    H H9A 0.2221 -0.1435 0.1838 0.074 Uiso calc R 1 1 . .
    H H9B 0.3459 -0.0938 0.141 0.074 Uiso calc R 1 1 . .
    C C10 0.4163(4) 0.0194(3) 0.21228(11) 0.0568(7) Uani d . 1 1 . .
    C C11 0.3845(4) 0.0329(3) 0.26468(11) 0.0567(7) Uani d . 1 1 . .
    C C12 0.5133(4) 0.0977(4) 0.30333(13) 0.0699(8) Uani d . 1 1 . .
    H H12 0.4902 0.1031 0.3384 0.084 Uiso calc R 1 1 . .
    C C13 0.6728(5) 0.1533(5) 0.29027(15) 0.0862(11) Uani d . 1 1 . .
    H H13 0.7582 0.197 0.3164 0.103 Uiso calc R 1 1 . .
    C C14 0.7079(5) 0.1450(6) 0.23877(17) 0.0932(12) Uani d . 1 1 . .
    H H14 0.8159 0.1852 0.2297 0.112 Uiso calc R 1 1 . .
    C C15 0.5817(4) 0.0764(5) 0.20012(14) 0.0781(10) Uani d . 1 1 . .
    H H15 0.6081 0.0684 0.1654 0.094 Uiso calc R 1 1 . .
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
    Br1 0.0729(3) 0.0918(3) 0.0707(3) -0.00307(17) 0.00932(18) 0.00600(16)
    S1 0.0576(4) 0.0567(4) 0.0563(4) 0.0182(3) -0.0120(3) -0.0109(3)
    O1 0.0681(12) 0.0486(11) 0.0884(15) 0.0129(10) 0.0105(10) -0.0114(10)
    O2 0.0531(12) 0.0549(12) 0.0823(14) 0.0223(9) -0.0014(10) -0.0076(10)
    N1 0.0388(10) 0.0404(11) 0.0466(11) 0.0060(8) 0.0005(8) -0.0039(8)
    N2 0.0435(11) 0.0446(11) 0.0550(12) 0.0048(9) 0.0011(9) -0.0070(9)
    N3 0.0468(11) 0.0477(12) 0.0583(13) 0.0048(9) 0.0018(9) -0.0063(10)
    N4 0.0445(11) 0.0464(12) 0.0532(12) 0.0101(9) 0.0027(9) -0.0019(9)
    C1 0.0530(15) 0.0498(16) 0.0480(14) 0.0154(12) 0.0030(11) -0.0014(11)
    C2 0.0472(14) 0.0459(14) 0.0442(13) 0.0136(11) 0.0013(10) 0.0011(10)
    C3 0.0391(12) 0.0516(14) 0.0623(15) 0.0094(11) 0.0007(11) -0.0028(12)
    C4 0.0414(13) 0.0442(13) 0.0610(15) 0.0043(10) -0.0010(11) -0.0028(11)
    C5 0.0409(12) 0.0413(12) 0.0429(12) 0.0101(10) 0.0012(9) -0.0009(9)
    C6 0.0391(12) 0.0458(14) 0.0624(15) 0.0063(10) 0.0026(11) -0.0007(11)
    C7 0.0500(14) 0.0413(13) 0.0589(15) 0.0015(11) 0.0009(12) -0.0023(11)
    C8 0.0406(12) 0.0457(13) 0.0456(13) 0.0090(10) 0.0037(10) 0.0001(10)
    C9 0.0615(17) 0.0648(18) 0.0545(16) 0.0235(14) -0.0098(13) -0.0083(13)
    C10 0.0516(16) 0.0634(17) 0.0519(15) 0.0204(13) -0.0066(12) -0.0011(12)
    C11 0.0564(16) 0.0570(16) 0.0538(16) 0.0134(12) -0.0038(12) 0.0022(12)
    C12 0.0649(19) 0.080(2) 0.0589(17) 0.0110(16) -0.0149(14) -0.0054(15)
    C13 0.066(2) 0.105(3) 0.079(2) -0.0006(19) -0.0213(18) -0.0040(19)
    C14 0.0483(18) 0.129(3) 0.098(3) 0.0027(19) -0.0050(17) 0.013(2)
    C15 0.0581(18) 0.113(3) 0.0615(19) 0.0226(19) 0.0036(15) 0.0099(18)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    Br1 C11 . 1.896(3) ?
    S1 C8 . 1.728(3) ?
    S1 C9 . 1.830(3) ?
    O1 C1 . 1.208(3) ?
    O2 C1 . 1.318(3) ?
    O2 H1 . 0.72(4) ?
    N1 C8 . 1.349(3) ?
    N1 N2 . 1.361(3) ?
    N1 C5 . 1.440(3) ?
    N2 N3 . 1.283(3) ?
    N3 N4 . 1.371(3) ?
    N4 C8 . 1.324(3) ?
    C1 C2 . 1.498(3) ?
    C2 C3 . 1.381(4) ?
    C2 C7 . 1.392(4) ?
    C3 C4 . 1.384(4) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.386(3) ?
    C4 H4 . 0.93 ?
    C5 C6 . 1.374(4) ?
    C6 C7 . 1.386(3) ?
    C6 H6 . 0.93 ?
    C7 H7 . 0.93 ?
    C9 C10 . 1.502(4) ?
    C9 H9A . 0.97 ?
    C9 H9B . 0.97 ?
    C10 C11 . 1.386(4) ?
    C10 C15 . 1.394(5) ?
    C11 C12 . 1.388(4) ?
    C12 C13 . 1.358(5) ?
    C12 H12 . 0.93 ?
    C13 C14 . 1.368(6) ?
    C13 H13 . 0.93 ?
    C14 C15 . 1.389(5) ?
    C14 H14 . 0.93 ?
    C15 H15 . 0.93 ?
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
    C8 S1 C9 . . 99.29(12) ?
    C1 O2 H1 . . 106(4) ?
    C8 N1 N2 . . 108.81(18) ?
    C8 N1 C5 . . 130.9(2) ?
    N2 N1 C5 . . 120.24(19) ?
    N3 N2 N1 . . 106.25(19) ?
    N2 N3 N4 . . 111.12(19) ?
    C8 N4 N3 . . 106.15(19) ?
    O1 C1 O2 . . 124.2(2) ?
    O1 C1 C2 . . 123.1(2) ?
    O2 C1 C2 . . 112.7(2) ?
    C3 C2 C7 . . 120.1(2) ?
    C3 C2 C1 . . 121.9(2) ?
    C7 C2 C1 . . 118.0(2) ?
    C2 C3 C4 . . 120.3(2) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    C3 C4 C5 . . 118.6(2) ?
    C3 C4 H4 . . 120.7 ?
    C5 C4 H4 . . 120.7 ?
    C6 C5 C4 . . 122.3(2) ?
    C6 C5 N1 . . 119.9(2) ?
    C4 C5 N1 . . 117.8(2) ?
    C5 C6 C7 . . 118.5(2) ?
    C5 C6 H6 . . 120.8 ?
    C7 C6 H6 . . 120.8 ?
    C6 C7 C2 . . 120.3(2) ?
    C6 C7 H7 . . 119.9 ?
    C2 C7 H7 . . 119.9 ?
    N4 C8 N1 . . 107.7(2) ?
    N4 C8 S1 . . 128.29(19) ?
    N1 C8 S1 . . 124.04(18) ?
    C10 C9 S1 . . 108.74(19) ?
    C10 C9 H9A . . 109.9 ?
    S1 C9 H9A . . 109.9 ?
    C10 C9 H9B . . 109.9 ?
    S1 C9 H9B . . 109.9 ?
    H9A C9 H9B . . 108.3 ?
    C11 C10 C15 . . 117.0(3) ?
    C11 C10 C9 . . 123.1(3) ?
    C15 C10 C9 . . 119.9(3) ?
    C10 C11 C12 . . 121.3(3) ?
    C10 C11 Br1 . . 120.5(2) ?
    C12 C11 Br1 . . 118.2(2) ?
    C13 C12 C11 . . 120.5(3) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C12 C13 C14 . . 120.0(3) ?
    C12 C13 H13 . . 120 ?
    C14 C13 H13 . . 120 ?
    C13 C14 C15 . . 119.9(4) ?
    C13 C14 H14 . . 120.1 ?
    C15 C14 H14 . . 120.1 ?
    C14 C15 C10 . . 121.4(3) ?
    C14 C15 H15 . . 119.3 ?
    C10 C15 H15 . . 119.3 ?
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
    C9 H9B O1 1_645 0.97 2.41 3.351(4) 163
    O2 H1 N4 1_465 0.73(4) 2.05(4) 2.746(3) 161(5)
    C1 O1 Cg1 1_565 1.208(3) 3.618(2) 4.5340(10)
                                               133(2)
    C11 Br1 Cg2 2_545 1.896(3) 3.582(2) 4.895(2) 124.0(10)
data_global
_journal_date_recd_electronic     2013-04-19
_journal_date_accepted     2013-05-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      7
_journal_page_first     o1083
_journal_page_last     o1084
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813014840
_journal_coeditor_code     LR2105
_publ_contact_author_name     'Ana C. Mafud'
_publ_contact_author_address
;
Instituto de Física de São Carlos
Av. do Trab. Sãocarlense, 400
São Carlos, SP, Brazil
;
_publ_contact_author_email     'mafud@usp.br'
_publ_contact_author_fax     '551633739874'
_publ_contact_author_phone     '551633739874'
_publ_section_title
;
4-{5-[(2-Bromobenzyl)sulfanyl]-1H-tetrazol-1-yl}benzoic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Mafud, Ana C.' .
;
Instituto de Física de São Carlos
Av. do Trab. Sãocarlense, 400
São Carlos, SP, Brazil
;
    'Mascarenhas, Yvonne P.' .
;
Instituto de Física de São Carlos
Av. do Trab. Sãocarlense, 400
São Carlos, SP, Brazil
;
    'Nascimento, Alessandro S.' .
;
Instituto de Física de São Carlos
Av. do Trab. Sãocarlense, 400
São Carlos, SP, Brazil
;
