##############################################################################
#                                                                            #
# 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     'SHELXL-2014/7'
_database_code_depnum_ccdc_archive     'CCDC 1413856'
_chemical_name_systematic
;
 (7-Methyl-2-oxo-2H-chromen-4-yl)methyl
piperidine-1-carbodithioate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H19 N O2 S2'
_chemical_formula_sum     'C17 H19 N O2 S2'
_chemical_formula_iupac     'C17 H19 N O2 S2'
_chemical_formula_weight     333.45
_chemical_melting_point     420
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P c'
_space_group_name_Hall     'P -2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    'x, -y, z+1/2'
_cell_length_a     4.9641(2)
_cell_length_b     11.4351(3)
_cell_length_c     14.0023(4)
_cell_angle_alpha     90
_cell_angle_beta     90.743(2)
_cell_angle_gamma     90
_cell_volume     794.77(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2119
_cell_measurement_theta_min     1.781
_cell_measurement_theta_max     24.998
_cell_measurement_temperature     296(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.393
_exptl_crystal_F_000     352
_exptl_absorpt_coefficient_mu     0.341
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2007)
;
_exptl_absorpt_correction_T_min     0.7700
_exptl_absorpt_correction_T_max     1.0000
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     4426
_diffrn_reflns_av_R_equivalents     0.0171
_diffrn_reflns_theta_min     1.781
_diffrn_reflns_theta_max     24.998
_diffrn_reflns_theta_full     24.998
_diffrn_measured_fraction_theta_max     0.963
_diffrn_measured_fraction_theta_full     0.963
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     16
_refine_special_details     ?
_reflns_number_total     2119
_reflns_number_gt     2027
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0272
_refine_ls_R_factor_gt     0.0256
_refine_ls_wR_factor_gt     0.0605
_refine_ls_wR_factor_ref     0.0615
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     2119
_refine_ls_number_parameters     200
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0331P)²+0.0991P] 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     0.144
_refine_diff_density_min     -0.134
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 704 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     0.05(3)
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'
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_cell_refinement
;
SAINT (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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 0.15995(16) 0.77643(6) 0.48353(6) 0.0417(2) Uani d 1 . .
    S S2 0.42720(17) 0.60022(8) 0.35570(7) 0.0529(3) Uani d 1 . .
    O O3 0.1614(4) 0.99061(19) 0.14352(14) 0.0405(5) Uani d 1 . .
    O O4 0.4912(5) 0.8912(2) 0.07897(17) 0.0579(7) Uani d 1 . .
    N N5 0.0507(6) 0.5536(2) 0.4834(2) 0.0496(7) Uani d 1 . .
    C C6 0.3753(7) 0.9153(3) 0.1512(2) 0.0414(8) Uani d 1 . .
    C C7 0.4412(7) 0.8712(3) 0.2455(2) 0.0379(8) Uani d 1 . .
    H H7 0.5761 0.8152 0.2518 0.045 Uiso calc 1 . .
    C C8 0.3150(6) 0.9079(2) 0.3245(2) 0.0324(7) Uani d 1 . .
    C C9 0.1022(6) 0.9951(2) 0.3146(2) 0.0320(7) Uani d 1 . .
    C C10 0.0312(6) 1.0321(2) 0.2230(2) 0.0331(7) Uani d 1 . .
    C C11 -0.1659(6) 1.1147(3) 0.2057(2) 0.0373(7) Uani d 1 . .
    H H11 -0.2102 1.1357 0.1433 0.045 Uiso calc 1 . .
    C C12 -0.2979(6) 1.1663(2) 0.2814(2) 0.0370(7) Uani d 1 . .
    C C13 -0.2277(6) 1.1305(3) 0.3735(2) 0.0396(8) Uani d 1 . .
    H H13 -0.3149 1.1640 0.4252 0.047 Uiso calc 1 . .
    C C14 -0.5104(7) 1.2582(3) 0.2648(3) 0.0509(9) Uani d 1 . .
    H H14A -0.5426 1.2672 0.1975 0.076 Uiso calc 1 . .
    H H14B -0.4501 1.3312 0.2913 0.076 Uiso calc 1 . .
    H H14C -0.6742 1.2348 0.2952 0.076 Uiso calc 1 . .
    C C15 -0.0339(6) 1.0474(2) 0.3902(2) 0.0366(7) Uani d 1 . .
    H H15 0.0076 1.0254 0.4526 0.044 Uiso calc 1 . .
    C C16 0.4049(6) 0.8639(3) 0.4206(2) 0.0379(7) Uani d 1 . .
    H H16A 0.4527 0.9305 0.4601 0.045 Uiso calc 1 . .
    H H16B 0.5665 0.8174 0.4125 0.045 Uiso calc 1 . .
    C C17 0.2071(6) 0.6311(3) 0.4400(2) 0.0378(7) Uani d 1 . .
    C C18 -0.1184(8) 0.5752(3) 0.5662(3) 0.0561(10) Uani d 1 . .
    H H18A -0.3046 0.5577 0.5499 0.067 Uiso calc 1 . .
    H H18B -0.1071 0.6570 0.5839 0.067 Uiso calc 1 . .
    C C19 -0.0287(10) 0.5001(3) 0.6495(3) 0.0669(11) Uani d 1 . .
    H H19A 0.1498 0.5243 0.6704 0.080 Uiso calc 1 . .
    H H19B -0.1507 0.5116 0.7022 0.080 Uiso calc 1 . .
    C C20 -0.0229(10) 0.3718(3) 0.6234(3) 0.0746(13) Uani d 1 . .
    H H20A -0.2056 0.3438 0.6136 0.090 Uiso calc 1 . .
    H H20B 0.0579 0.3275 0.6754 0.090 Uiso calc 1 . .
    C C21 0.1378(9) 0.3527(3) 0.5330(3) 0.0733(14) Uani d 1 . .
    H H21A 0.3265 0.3689 0.5461 0.088 Uiso calc 1 . .
    H H21B 0.1224 0.2716 0.5136 0.088 Uiso calc 1 . .
    C C22 0.0400(8) 0.4302(3) 0.4529(3) 0.0630(11) Uani d 1 . .
    H H22A 0.1521 0.4192 0.3974 0.076 Uiso calc 1 . .
    H H22B -0.1436 0.4095 0.4353 0.076 Uiso calc 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 C17 . 1.786(3) ?
    S1 C16 . 1.812(3) ?
    S2 C17 . 1.657(3) ?
    O3 C6 . 1.370(4) ?
    O3 C10 . 1.378(3) ?
    O4 C6 . 1.202(4) ?
    N5 C17 . 1.330(4) ?
    N5 C18 . 1.461(4) ?
    N5 C22 . 1.475(4) ?
    C6 C7 . 1.447(4) ?
    C7 C8 . 1.346(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.458(4) ?
    C8 C16 . 1.499(4) ?
    C9 C10 . 1.392(4) ?
    C9 C15 . 1.397(4) ?
    C10 C11 . 1.379(4) ?
    C11 C12 . 1.385(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.394(5) ?
    C12 C14 . 1.505(4) ?
    C13 C15 . 1.371(5) ?
    C13 H13 . 0.9300 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 H15 . 0.9300 ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C18 C19 . 1.511(5) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 C20 . 1.512(6) ?
    C19 H19A . 0.9700 ?
    C19 H19B . 0.9700 ?
    C20 C21 . 1.521(6) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    C21 C22 . 1.505(6) ?
    C21 H21A . 0.9700 ?
    C21 H21B . 0.9700 ?
    C22 H22A . 0.9700 ?
    C22 H22B . 0.9700 ?
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
    C17 S1 C16 . . 104.81(15) ?
    C6 O3 C10 . . 121.6(2) ?
    C17 N5 C18 . . 126.5(3) ?
    C17 N5 C22 . . 121.6(3) ?
    C18 N5 C22 . . 111.9(3) ?
    O4 C6 O3 . . 117.2(3) ?
    O4 C6 C7 . . 125.6(3) ?
    O3 C6 C7 . . 117.1(3) ?
    C8 C7 C6 . . 122.6(3) ?
    C8 C7 H7 . . 118.7 ?
    C6 C7 H7 . . 118.7 ?
    C7 C8 C9 . . 118.7(3) ?
    C7 C8 C16 . . 119.8(3) ?
    C9 C8 C16 . . 121.5(3) ?
    C10 C9 C15 . . 116.7(3) ?
    C10 C9 C8 . . 118.0(3) ?
    C15 C9 C8 . . 125.3(3) ?
    C11 C10 O3 . . 115.7(3) ?
    C11 C10 C9 . . 122.7(3) ?
    O3 C10 C9 . . 121.6(3) ?
    C10 C11 C12 . . 120.0(3) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C11 C12 C13 . . 117.9(3) ?
    C11 C12 C14 . . 121.2(3) ?
    C13 C12 C14 . . 120.9(3) ?
    C15 C13 C12 . . 121.9(3) ?
    C15 C13 H13 . . 119.1 ?
    C12 C13 H13 . . 119.1 ?
    C12 C14 H14A . . 109.5 ?
    C12 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C12 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C13 C15 C9 . . 120.9(3) ?
    C13 C15 H15 . . 119.6 ?
    C9 C15 H15 . . 119.6 ?
    C8 C16 S1 . . 115.4(2) ?
    C8 C16 H16A . . 108.4 ?
    S1 C16 H16A . . 108.4 ?
    C8 C16 H16B . . 108.4 ?
    S1 C16 H16B . . 108.4 ?
    H16A C16 H16B . . 107.5 ?
    N5 C17 S2 . . 125.3(2) ?
    N5 C17 S1 . . 112.6(2) ?
    S2 C17 S1 . . 122.13(19) ?
    N5 C18 C19 . . 110.5(3) ?
    N5 C18 H18A . . 109.6 ?
    C19 C18 H18A . . 109.6 ?
    N5 C18 H18B . . 109.6 ?
    C19 C18 H18B . . 109.6 ?
    H18A C18 H18B . . 108.1 ?
    C20 C19 C18 . . 111.8(4) ?
    C20 C19 H19A . . 109.3 ?
    C18 C19 H19A . . 109.3 ?
    C20 C19 H19B . . 109.3 ?
    C18 C19 H19B . . 109.3 ?
    H19A C19 H19B . . 107.9 ?
    C19 C20 C21 . . 110.6(3) ?
    C19 C20 H20A . . 109.5 ?
    C21 C20 H20A . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    C21 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 108.1 ?
    C22 C21 C20 . . 111.6(4) ?
    C22 C21 H21A . . 109.3 ?
    C20 C21 H21A . . 109.3 ?
    C22 C21 H21B . . 109.3 ?
    C20 C21 H21B . . 109.3 ?
    H21A C21 H21B . . 108.0 ?
    N5 C22 C21 . . 109.7(3) ?
    N5 C22 H22A . . 109.7 ?
    C21 C22 H22A . . 109.7 ?
    N5 C22 H22B . . 109.7 ?
    C21 C22 H22B . . 109.7 ?
    H22A C22 H22B . . 108.2 ?
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
    C10 O3 C6 O4 . . . . -173.9(3) ?
    C10 O3 C6 C7 . . . . 6.4(4) ?
    O4 C6 C7 C8 . . . . 175.3(3) ?
    O3 C6 C7 C8 . . . . -5.1(4) ?
    C6 C7 C8 C9 . . . . 0.4(4) ?
    C6 C7 C8 C16 . . . . -176.3(3) ?
    C7 C8 C9 C10 . . . . 3.0(4) ?
    C16 C8 C9 C10 . . . . 179.6(3) ?
    C7 C8 C9 C15 . . . . -175.4(3) ?
    C16 C8 C9 C15 . . . . 1.2(4) ?
    C6 O3 C10 C11 . . . . 174.8(3) ?
    C6 O3 C10 C9 . . . . -3.2(4) ?
    C15 C9 C10 C11 . . . . -1.0(4) ?
    C8 C9 C10 C11 . . . . -179.6(3) ?
    C15 C9 C10 O3 . . . . 176.8(2) ?
    C8 C9 C10 O3 . . . . -1.7(4) ?
    O3 C10 C11 C12 . . . . -176.5(2) ?
    C9 C10 C11 C12 . . . . 1.5(4) ?
    C10 C11 C12 C13 . . . . -1.1(4) ?
    C10 C11 C12 C14 . . . . 178.9(3) ?
    C11 C12 C13 C15 . . . . 0.3(4) ?
    C14 C12 C13 C15 . . . . -179.7(3) ?
    C12 C13 C15 C9 . . . . 0.1(5) ?
    C10 C9 C15 C13 . . . . 0.2(4) ?
    C8 C9 C15 C13 . . . . 178.6(3) ?
    C7 C8 C16 S1 . . . . -115.5(3) ?
    C9 C8 C16 S1 . . . . 67.9(3) ?
    C17 S1 C16 C8 . . . . 85.8(3) ?
    C18 N5 C17 S2 . . . . 171.3(3) ?
    C22 N5 C17 S2 . . . . -6.1(5) ?
    C18 N5 C17 S1 . . . . -7.9(4) ?
    C22 N5 C17 S1 . . . . 174.7(3) ?
    C16 S1 C17 N5 . . . . 176.6(2) ?
    C16 S1 C17 S2 . . . . -2.7(2) ?
    C17 N5 C18 C19 . . . . -118.1(4) ?
    C22 N5 C18 C19 . . . . 59.5(4) ?
    N5 C18 C19 C20 . . . . -55.0(5) ?
    C18 C19 C20 C21 . . . . 51.6(5) ?
    C19 C20 C21 C22 . . . . -52.7(5) ?
    C17 N5 C22 C21 . . . . 117.6(4) ?
    C18 N5 C22 C21 . . . . -60.2(4) ?
    C20 C21 C22 N5 . . . . 56.3(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
    C13 H13 O4 2_475 0.93 2.45 3.223(4) 140.00 yes
    C16 H16B S2 . 0.97 2.70 3.152(4) 109.00 yes
    C18 H18B S1 . 0.97 2.38 2.930(4) 116.00 yes
    C22 H22A S2 . 0.97 2.55 3.065(4) 113.00 yes
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2015-05-31
_journal_date_accepted     2015-07-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      8
_journal_page_first     o606
_journal_page_last     o607
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015013699
_journal_coeditor_code     ZL2626
_publ_contact_author_name     'H.C.Devarajegowda'
_publ_contact_author_address
;
Department of Physics
Yuvaraja's College (Constituent College)
University of Mysore Mysore
Karnataka
India
;
_publ_contact_author_email     'devarajegowda@yahoo.com'
_publ_contact_author_fax     '+91 0821 2419292'
_publ_contact_author_phone     '+91 0821 2518101'
_publ_section_title
;
Crystal structure of (7-methyl-2-oxo-2H-chromen-4-yl)methyl
piperidine-1-carbodithioate
;
loop_
    _publ_author_name
    _publ_author_address
    'K. R. Roopashree'
;
Department of Physics
Yuvaraja's College (Constituent College)
University of Mysore, Mysore 570 005
Karnataka, India
;
    'T. G. Meenakshi'
;
Department of Physics
Y.Y.D. Govt. First Grade College
Belur 573 115 Hassan
Karnataka, India
;
    'K. Mahesh Kumar'
;
Department of Chemistry
Karnatak University's Karnatak Science College
Dharwad, Karnataka 580 001, India
;
    'O. Kotresh'
;
Department of Chemistry
Karnatak University's Karnatak Science College
Dharwad, Karnataka 580 001, India
;
    'H. C. Devarajegowda'
;
Department of Physics
Yuvaraja's College (Constituent College)
University of Mysore, Mysore 570 005
Karnataka, India
;
