# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_boly341_0m
_database_code_depnum_ccdc_archive 'CCDC 1479789'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5-(naphthalen-2-ylmethyl)-3-(piperidin-1-ylmethyl)-1,3,4-oxadiazole-2(3H)-thione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N3 O S'
_chemical_formula_sum            'C19 H21 N3 O S'
_chemical_formula_weight         339.45

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0419(4)
_cell_length_b                   8.0935(5)
_cell_length_c                   15.4614(8)
_cell_angle_alpha                85.744(2)
_cell_angle_beta                 89.568(2)
_cell_angle_gamma                80.461(2)
_cell_volume                     866.61(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    17301
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      28.4

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9182
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_process_details   'SADABS (Bruker, 2009)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker SMART APEX CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 83.66
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            52192
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0345
_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       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.2
_diffrn_reflns_theta_max         28.4
_reflns_number_total             4332
_reflns_number_gt                3019
_reflns_threshold_expression     I>2sigma(I)
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
;                                                             
SHELXTL,  and PLATON ( Spek, 2009)
;


_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0458P)²+0.2878P] where P=(Fo²+2Fc²)/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         4332
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          <0.001
_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
S1 S 0.27943(7) 0.32901(6) 0.01038(3) 0.04784(16) Uani 1 1 d . . .
O1 O 0.21527(16) 0.63814(15) -0.06633(7) 0.0368(3) Uani 1 1 d . . .
N1 N 0.2673(2) 0.63808(18) 0.06991(9) 0.0354(3) Uani 1 1 d . . .
N2 N 0.2347(2) 0.80558(18) 0.03844(9) 0.0379(3) Uani 1 1 d . . .
N3 N 0.1737(2) 0.63741(19) 0.21889(9) 0.0370(3) Uani 1 1 d . . .
C1 C 0.4783(3) 0.9871(2) -0.16933(13) 0.0478(5) Uani 1 1 d . . .
H1 H 0.5003 1.0316 -0.1173 0.057 Uiso 1 1 calc R . .
C2 C 0.6142(3) 0.9795(2) -0.23165(14) 0.0503(5) Uani 1 1 d . . .
H2 H 0.7278 1.0200 -0.2221 0.060 Uiso 1 1 calc R . .
C3 C 0.5866(3) 0.9113(2) -0.31078(12) 0.0441(4) Uani 1 1 d . . .
C4 C 0.7263(3) 0.8996(3) -0.37764(15) 0.0597(6) Uani 1 1 d . . .
H4 H 0.8414 0.9389 -0.3698 0.072 Uiso 1 1 calc R . .
C5 C 0.6945(4) 0.8318(3) -0.45286(16) 0.0697(7) Uani 1 1 d . . .
H5 H 0.7876 0.8250 -0.4960 0.084 Uiso 1 1 calc R . .
C6 C 0.5228(4) 0.7724(3) -0.46574(15) 0.0711(7) Uani 1 1 d . . .
H6 H 0.5026 0.7257 -0.5174 0.085 Uiso 1 1 calc R . .
C7 C 0.3851(4) 0.7819(3) -0.40382(14) 0.0611(6) Uani 1 1 d . . .
H7 H 0.2712 0.7419 -0.4134 0.073 Uiso 1 1 calc R . .
C8 C 0.4130(3) 0.8519(2) -0.32486(12) 0.0440(4) Uani 1 1 d . . .
C9 C 0.2727(3) 0.8630(2) -0.25807(12) 0.0439(4) Uani 1 1 d . . .
H9 H 0.1574 0.8245 -0.2665 0.053 Uiso 1 1 calc R . .
C10 C 0.3038(3) 0.9288(2) -0.18196(12) 0.0396(4) Uani 1 1 d . . .
C11 C 0.1565(3) 0.9381(2) -0.11018(13) 0.0486(5) Uani 1 1 d . . .
H11A H 0.1499 1.0443 -0.0841 0.058 Uiso 1 1 calc R . .
H11B H 0.0309 0.9345 -0.1346 0.058 Uiso 1 1 calc R . .
C12 C 0.2034(2) 0.7987(2) -0.04216(12) 0.0365(4) Uani 1 1 d . . .
C13 C 0.2553(2) 0.5349(2) 0.00728(11) 0.0343(4) Uani 1 1 d . . .
C14 C 0.3284(3) 0.5920(2) 0.15911(11) 0.0402(4) Uani 1 1 d . . .
H14A H 0.3730 0.4718 0.1664 0.048 Uiso 1 1 calc R . .
H14B H 0.4352 0.6481 0.1721 0.048 Uiso 1 1 calc R . .
C15 C 0.0210(3) 0.5374(3) 0.20983(12) 0.0450(5) Uani 1 1 d . . .
H15A H 0.0733 0.4193 0.2218 0.054 Uiso 1 1 calc R . .
H15B H -0.0268 0.5532 0.1506 0.054 Uiso 1 1 calc R . .
C16 C -0.1430(3) 0.5864(3) 0.27084(14) 0.0552(5) Uani 1 1 d . . .
H16A H -0.2402 0.5160 0.2646 0.066 Uiso 1 1 calc R . .
H16B H -0.2017 0.7022 0.2565 0.066 Uiso 1 1 calc R . .
C17 C -0.0702(4) 0.5664(3) 0.36369(14) 0.0646(6) Uani 1 1 d . . .
H17A H -0.1742 0.6068 0.4022 0.077 Uiso 1 1 calc R . .
H17B H -0.0250 0.4486 0.3804 0.077 Uiso 1 1 calc R . .
C18 C 0.0927(4) 0.6654(4) 0.37171(14) 0.0734(8) Uani 1 1 d . . .
H18A H 0.0434 0.7844 0.3616 0.088 Uiso 1 1 calc R . .
H18B H 0.1453 0.6457 0.4301 0.088 Uiso 1 1 calc R . .
C19 C 0.2501(3) 0.6148(3) 0.30731(12) 0.0511(5) Uani 1 1 d . . .
H19A H 0.3504 0.6826 0.3122 0.061 Uiso 1 1 calc R . .
H19B H 0.3067 0.4980 0.3204 0.061 Uiso 1 1 calc R . .


_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
S1 C13 1.6439(18) . ?
O1 C13 1.363(2) . ?
O1 C12 1.368(2) . ?
N1 C13 1.337(2) . ?
N1 N2 1.389(2) . ?
N1 C14 1.451(2) . ?
N2 C12 1.274(2) . ?
N3 C14 1.442(2) . ?
N3 C19 1.461(2) . ?
N3 C15 1.462(2) . ?
C1 C2 1.351(3) . ?
C1 C10 1.407(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.407(3) . ?
C2 H2 0.9300 . ?
C3 C8 1.410(3) . ?
C3 C4 1.419(3) . ?
C4 C5 1.358(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.354(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.412(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.421(3) . ?
C9 C10 1.361(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.511(3) . ?
C11 C12 1.481(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.506(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.516(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.514(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.510(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
C13 O1 C12 106.35(13) . . ?
C13 N1 N2 111.95(14) . . ?
C13 N1 C14 127.37(15) . . ?
N2 N1 C14 120.30(14) . . ?
C12 N2 N1 103.51(14) . . ?
C14 N3 C19 109.20(14) . . ?
C14 N3 C15 111.12(14) . . ?
C19 N3 C15 110.66(14) . . ?
C2 C1 C10 121.02(18) . . ?
C2 C1 H1 119.5 . . ?
C10 C1 H1 119.5 . . ?
C1 C2 C3 121.02(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C8 118.97(18) . . ?
C2 C3 C4 122.85(19) . . ?
C8 C3 C4 118.18(19) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 119.24(19) . . ?
C3 C8 C9 118.45(17) . . ?
C7 C8 C9 122.31(19) . . ?
C10 C9 C8 121.29(18) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C1 119.25(18) . . ?
C9 C10 C11 121.47(18) . . ?
C1 C10 C11 119.27(17) . . ?
C12 C11 C10 112.19(15) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N2 C12 O1 113.27(15) . . ?
N2 C12 C11 128.97(17) . . ?
O1 C12 C11 117.76(15) . . ?
N1 C13 O1 104.91(14) . . ?
N1 C13 S1 131.15(14) . . ?
O1 C13 S1 123.94(12) . . ?
N3 C14 N1 111.47(14) . . ?
N3 C14 H14A 109.3 . . ?
N1 C14 H14A 109.3 . . ?
N3 C14 H14B 109.3 . . ?
N1 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C16 111.46(16) . . ?
N3 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N3 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 110.11(18) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C16 109.60(18) . . ?
C18 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C17 111.00(18) . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N3 C19 C18 110.72(18) . . ?
N3 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?

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
C13 N1 N2 C12 0.17(18) . . . . ?
C14 N1 N2 C12 173.64(14) . . . . ?
C10 C1 C2 C3 -0.7(3) . . . . ?
C1 C2 C3 C8 0.6(3) . . . . ?
C1 C2 C3 C4 -179.43(19) . . . . ?
C2 C3 C4 C5 179.6(2) . . . . ?
C8 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C2 C3 C8 C7 -179.42(19) . . . . ?
C4 C3 C8 C7 0.7(3) . . . . ?
C2 C3 C8 C9 -0.2(3) . . . . ?
C4 C3 C8 C9 179.88(17) . . . . ?
C6 C7 C8 C3 -0.3(3) . . . . ?
C6 C7 C8 C9 -179.5(2) . . . . ?
C3 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C10 179.05(19) . . . . ?
C8 C9 C10 C1 0.1(3) . . . . ?
C8 C9 C10 C11 -178.91(16) . . . . ?
C2 C1 C10 C9 0.4(3) . . . . ?
C2 C1 C10 C11 179.39(17) . . . . ?
C9 C10 C11 C12 98.9(2) . . . . ?
C1 C10 C11 C12 -80.0(2) . . . . ?
N1 N2 C12 O1 -0.69(18) . . . . ?
N1 N2 C12 C11 178.92(17) . . . . ?
C13 O1 C12 N2 0.95(18) . . . . ?
C13 O1 C12 C11 -178.70(15) . . . . ?
C10 C11 C12 N2 120.3(2) . . . . ?
C10 C11 C12 O1 -60.1(2) . . . . ?
N2 N1 C13 O1 0.39(17) . . . . ?
C14 N1 C13 O1 -172.51(14) . . . . ?
N2 N1 C13 S1 -179.34(13) . . . . ?
C14 N1 C13 S1 7.8(3) . . . . ?
C12 O1 C13 N1 -0.76(16) . . . . ?
C12 O1 C13 S1 179.00(12) . . . . ?
C19 N3 C14 N1 -170.51(15) . . . . ?
C15 N3 C14 N1 67.1(2) . . . . ?
C13 N1 C14 N3 -115.43(18) . . . . ?
N2 N1 C14 N3 72.19(19) . . . . ?
C14 N3 C15 C16 -178.89(16) . . . . ?
C19 N3 C15 C16 59.6(2) . . . . ?
N3 C15 C16 C17 -57.6(2) . . . . ?
C15 C16 C17 C18 54.7(3) . . . . ?
C16 C17 C18 C19 -54.9(3) . . . . ?
C14 N3 C19 C18 178.60(17) . . . . ?
C15 N3 C19 C18 -58.8(2) . . . . ?
C17 C18 C19 N3 57.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_theta_full        28.4
_diffrn_measured_fraction_theta_full 0.99
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.067
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method ethanol
