##############################################################################
#                                                                            #
# 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
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_journal_date_recd_electronic     2019-07-19
_journal_date_accepted     2019-08-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue      9
_journal_page_first     1331
_journal_page_last     1335
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019011459
_journal_coeditor_code     HB7842
_publ_contact_author_name     'Doctor Yurii Slyvka'
_publ_contact_author_address
;Faculty of Chemistry,
Ivan Franko National University of Lviv,
Kyryla i Mefodia Str, 6,
79005 L'viv, Ukraine
;
_publ_contact_author_email     yurii.slyvka@lnu.edu.ua
_publ_contact_author_phone      380322394506
_publ_section_title
;\
Crystal structure, Hirshfeld surface analysis and computational studies of
5-[(prop-2-en-1-yl)sulfanyl]-1-[2-(trifluoromethyl)phenyl]-1H-\
tetrazole
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Slyvka, Yurii' .
;
Faculty of Chemistry,
Ivan Franko National University of Lviv,
Kyryla i Mefodia Str, 6,
79005 L'viv,
Ukraine
;
    'Goreshnik, Evgeny' .
;
Department of Inorganic Chemistry and Technology,
Jožef Stefan Institute,
Jamova 39,
SI-1000 Ljubljana,
Slovenia
;
    'Pokhodylo, Nazariy' .
;
Faculty of Chemistry,
Ivan Franko National University of Lviv,
Kyryla i Mefodia Str, 6,
79005 L'viv,
Ukraine
;
    'Mys`kiv, Marian' .
;
Faculty of Chemistry,
Ivan Franko National University of Lviv,
Kyryla i Mefodia Str, 6,
79005 L'viv,
Ukraine
;
_publ_section_synopsis
;
The title compound was synthesized from 2-(trifluoromethyl)aniline by a
multi-step reaction and is constructed from a pair of aromatic rings
[2-(trifluoromethyl)phenyl and tetrazole], which are turned by 76.8(1)°
relative to each other because of significant steric hindrance of the
trifluoromethyl group at the ortho position of the benzene ring.In the
crystal, very weak C---H...N and C---H...F hydrogen bonds and aromatic π--π
stacking interactions link the molecules into a three-dimensional network.
;
_chemical_name_systematic
;\
5-[(Prop-2-en-1-yl)sulfanyl]-1-[2-(trifluoromethyl)phenyl]-1H-\
tetrazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H9 F3 N4 S'
_chemical_formula_sum     'C11 H9 F3 N4 S'
_chemical_formula_iupac     'C11 H9 F3 N4 S'
_chemical_formula_weight     286.28
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n a 21'
_space_group_name_Hall     'P 2c -2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     7.6595(3)
_cell_length_b     20.9841(7)
_cell_length_c     7.8641(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1263.98(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9726
_cell_measurement_theta_min     3.8470
_cell_measurement_theta_max     28.3700
_cell_measurement_temperature     150.00(10)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.242
_exptl_crystal_size_min     0.149
_exptl_crystal_density_diffrn     1.504
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     584
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    -10 -7 1 0.0950
    10 7 -1 0.0950
    0 1 11 0.1607
    -1 -1 -11 0.1802
    -1 -29 0 0.0812
    1 28 -3 0.0551
    2 29 2 0.0660
    1 -17 9 0.1496
    -10 2 -4 0.1065
    -8 19 0 0.0998
    3 -13 -9 0.1847
    8 14 -5 0.0883
_exptl_absorpt_coefficient_mu     0.284
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_absorpt_correction_T_min     0.929
_exptl_absorpt_correction_T_max     0.969
_diffrn_ambient_temperature     150
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
            'Rigaku Oxford Diffraction New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.6426
_diffrn_reflns_number     28170
_diffrn_reflns_av_R_equivalents     0.0589
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_theta_min     2.766
_diffrn_reflns_theta_max     28.924
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.968
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -28
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_refine_special_details
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9)
2.c X=CH2 refined with riding coordinates:
 C4(H4A,H4B)
;
_reflns_number_total     3094
_reflns_number_gt     2730
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0451
_refine_ls_R_factor_gt     0.0352
_refine_ls_wR_factor_gt     0.0737
_refine_ls_wR_factor_ref     0.0792
_refine_ls_goodness_of_fit_ref     1.071
_refine_ls_restrained_S_all     1.071
_refine_ls_number_reflns     3094
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0298P)²+0.4395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.231
_refine_diff_density_min     -0.224
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1094 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack     0.07(4)
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'
    F F 0.0171 0.0103 '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'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  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_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.82933(7) 0.43951(3) 0.47114(11) 0.02848(15) Uani d 1 . .
    F F1 0.4353(3) 0.24877(9) 0.1989(3) 0.0619(6) Uani d 1 . .
    F F2 0.5490(3) 0.34169(11) 0.2020(2) 0.0590(6) Uani d 1 . .
    F F3 0.2811(3) 0.32951(12) 0.2643(3) 0.0614(6) Uani d 1 . .
    N N1 0.4878(3) 0.41022(10) 0.5110(3) 0.0263(5) Uani d 1 . .
    N N2 0.3257(3) 0.43591(10) 0.4866(5) 0.0357(6) Uani d 1 . .
    N N3 0.3518(3) 0.49149(11) 0.4245(4) 0.0406(7) Uani d 1 . .
    N N4 0.5253(3) 0.50465(11) 0.4058(3) 0.0348(6) Uani d 1 . .
    C C1 0.6066(3) 0.45334(10) 0.4616(4) 0.0252(5) Uani d 1 . .
    C C2 0.9068(3) 0.51253(12) 0.3701(3) 0.0264(5) Uani d 1 . .
    H H2A 1.030061 0.506647 0.335573 0.032 Uiso calc 1 . .
    H H2B 0.837482 0.520356 0.265975 0.032 Uiso calc 1 . .
    C C3 0.8943(3) 0.56925(10) 0.4825(5) 0.0301(5) Uani d 1 . .
    H H3 0.781849 0.582487 0.519235 0.036 Uiso calc 1 . .
    C C4 1.0299(4) 0.60194(13) 0.5336(4) 0.0378(7) Uani d 1 . .
    H H4A 1.143885 0.589750 0.498837 0.045 Uiso calc 1 . .
    H H4B 1.014415 0.637872 0.605561 0.045 Uiso calc 1 . .
    C C5 0.5129(3) 0.34687(11) 0.5739(3) 0.0253(5) Uani d 1 . .
    C C6 0.5647(4) 0.33874(16) 0.7405(4) 0.0363(7) Uani d 1 . .
    H H6 0.580710 0.374616 0.812478 0.044 Uiso calc 1 . .
    C C7 0.5933(5) 0.27776(17) 0.8017(4) 0.0436(8) Uani d 1 . .
    H H7 0.631875 0.271828 0.915363 0.052 Uiso calc 1 . .
    C C8 0.5662(4) 0.22597(15) 0.6992(5) 0.0427(8) Uani d 1 . .
    H H8 0.583610 0.184288 0.743224 0.051 Uiso calc 1 . .
    C C9 0.5136(4) 0.23375(13) 0.5317(4) 0.0370(7) Uani d 1 . .
    H H9 0.495146 0.197514 0.461602 0.044 Uiso calc 1 . .
    C C10 0.4879(3) 0.29472(11) 0.4665(4) 0.0278(5) Uani d 1 . .
    C C11 0.4394(4) 0.30342(14) 0.2845(4) 0.0373(7) Uani d 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C1 . 1.732(2) ?
    S1 C2 . 1.825(3) ?
    F1 C11 . 1.330(3) ?
    F2 C11 . 1.331(4) ?
    F3 C11 . 1.340(4) ?
    N1 N2 . 1.367(3) ?
    N1 C1 . 1.341(3) ?
    N1 C5 . 1.431(3) ?
    N2 N3 . 1.280(3) ?
    N3 N4 . 1.365(3) ?
    N4 C1 . 1.319(3) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C2 C3 . 1.486(4) ?
    C3 H3 . 0.9500 ?
    C3 C4 . 1.308(4) ?
    C4 H4A . 0.9500 ?
    C4 H4B . 0.9500 ?
    C5 C6 . 1.380(4) ?
    C5 C10 . 1.396(4) ?
    C6 H6 . 0.9500 ?
    C6 C7 . 1.384(5) ?
    C7 H7 . 0.9500 ?
    C7 C8 . 1.369(5) ?
    C8 H8 . 0.9500 ?
    C8 C9 . 1.387(5) ?
    C9 H9 . 0.9500 ?
    C9 C10 . 1.392(4) ?
    C10 C11 . 1.490(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
    C1 S1 C2 . . 99.24(12) ?
    N2 N1 C5 . . 122.5(2) ?
    C1 N1 N2 . . 108.0(2) ?
    C1 N1 C5 . . 129.5(2) ?
    N3 N2 N1 . . 105.7(2) ?
    N2 N3 N4 . . 112.2(2) ?
    C1 N4 N3 . . 105.0(2) ?
    N1 C1 S1 . . 122.86(17) ?
    N4 C1 S1 . . 128.06(19) ?
    N4 C1 N1 . . 109.1(2) ?
    S1 C2 H2A . . 109.0 ?
    S1 C2 H2B . . 109.0 ?
    H2A C2 H2B . . 107.8 ?
    C3 C2 S1 . . 113.13(19) ?
    C3 C2 H2A . . 109.0 ?
    C3 C2 H2B . . 109.0 ?
    C2 C3 H3 . . 118.3 ?
    C4 C3 C2 . . 123.5(2) ?
    C4 C3 H3 . . 118.3 ?
    C3 C4 H4A . . 120.0 ?
    C3 C4 H4B . . 120.0 ?
    H4A C4 H4B . . 120.0 ?
    C6 C5 N1 . . 118.8(2) ?
    C6 C5 C10 . . 121.1(2) ?
    C10 C5 N1 . . 120.0(2) ?
    C5 C6 H6 . . 120.3 ?
    C5 C6 C7 . . 119.3(3) ?
    C7 C6 H6 . . 120.3 ?
    C6 C7 H7 . . 119.8 ?
    C8 C7 C6 . . 120.4(3) ?
    C8 C7 H7 . . 119.8 ?
    C7 C8 H8 . . 119.7 ?
    C7 C8 C9 . . 120.6(3) ?
    C9 C8 H8 . . 119.7 ?
    C8 C9 H9 . . 120.0 ?
    C8 C9 C10 . . 120.0(3) ?
    C10 C9 H9 . . 120.0 ?
    C5 C10 C11 . . 121.3(2) ?
    C9 C10 C5 . . 118.5(3) ?
    C9 C10 C11 . . 120.1(3) ?
    F1 C11 F2 . . 106.8(3) ?
    F1 C11 F3 . . 105.7(3) ?
    F1 C11 C10 . . 112.7(2) ?
    F2 C11 F3 . . 105.5(3) ?
    F2 C11 C10 . . 112.6(2) ?
    F3 C11 C10 . . 112.9(2) ?
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
    S1 C2 C3 C4 . . . . 117.0(3) ?
    N1 N2 N3 N4 . . . . 0.0(4) ?
    N1 C5 C6 C7 . . . . -178.5(3) ?
    N1 C5 C10 C9 . . . . 179.9(2) ?
    N1 C5 C10 C11 . . . . 1.5(4) ?
    N2 N1 C1 S1 . . . . -179.8(3) ?
    N2 N1 C1 N4 . . . . -0.6(3) ?
    N2 N1 C5 C6 . . . . -104.5(3) ?
    N2 N1 C5 C10 . . . . 76.6(3) ?
    N2 N3 N4 C1 . . . . -0.3(4) ?
    N3 N4 C1 S1 . . . . 179.7(2) ?
    N3 N4 C1 N1 . . . . 0.6(3) ?
    C1 S1 C2 C3 . . . . 75.0(2) ?
    C1 N1 N2 N3 . . . . 0.4(4) ?
    C1 N1 C5 C6 . . . . 77.8(4) ?
    C1 N1 C5 C10 . . . . -101.1(3) ?
    C2 S1 C1 N1 . . . . 175.3(2) ?
    C2 S1 C1 N4 . . . . -3.8(3) ?
    C5 N1 N2 N3 . . . . -177.7(2) ?
    C5 N1 C1 S1 . . . . -1.9(4) ?
    C5 N1 C1 N4 . . . . 177.3(2) ?
    C5 C6 C7 C8 . . . . -1.6(5) ?
    C5 C10 C11 F1 . . . . 174.8(2) ?
    C5 C10 C11 F2 . . . . 53.9(4) ?
    C5 C10 C11 F3 . . . . -65.4(3) ?
    C6 C5 C10 C9 . . . . 1.1(4) ?
    C6 C5 C10 C11 . . . . -177.3(3) ?
    C6 C7 C8 C9 . . . . 1.4(5) ?
    C7 C8 C9 C10 . . . . 0.0(5) ?
    C8 C9 C10 C5 . . . . -1.2(4) ?
    C8 C9 C10 C11 . . . . 177.2(3) ?
    C9 C10 C11 F1 . . . . -3.6(4) ?
    C9 C10 C11 F2 . . . . -124.5(3) ?
    C9 C10 C11 F3 . . . . 116.2(3) ?
    C10 C5 C6 C7 . . . . 0.3(4) ?
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
    C2 H2A N3 1_655 0.99 2.58 3.464(3) 148 yes
    C2 H2B N2 2_664 0.99 2.69 3.666(4) 169 yes
    C3 H3 F3 2_665 0.95 2.71 3.351(3) 125 yes
    C4 H4A N3 1_655 0.95 2.67 3.491(3) 145 yes
    C4 H4B F1 4_655 0.95 2.47 3.355(3) 155 yes
    C6 H6 N4 2_665 0.95 2.76 3.601(3) 148 yes
_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     ?
_shelx_estimated_absorpt_T_max     ?
