# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_emam4
_database_code_depnum_ccdc_archive 'CCDC 1977639'
loop_
_audit_author_name
_audit_author_address
'O. Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-01-14 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_date             2019-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H21 N3 S'
_chemical_formula_sum            'C14 H21 N3 S'
_chemical_formula_weight         263.40
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8339(2)
_cell_length_b                   15.8974(2)
_cell_length_c                   9.4749(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.464(2)
_cell_angle_gamma                90
_cell_volume                     1348.26(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12263
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.1
_cell_measurement_theta_min      5.1
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    2.006
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0244
-1 0 0 0.0295
0 -1 1 0.0580
0 1 -1 0.0837
1 -1 -2 0.0620
-1 2 1 0.0618
1 -2 -1 0.0590
0 -2 -1 0.0582
1 2 -1 0.0705
-1 -2 1 0.0763
0 1 0 0.0572

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05

_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15881
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.304
_diffrn_reflns_theta_min         5.566
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  25.00   0.50    0.50    --  -54.56  19.00  60.00  102
  2  ω   -127.00 -33.00   0.50    0.50    --  -54.56 -77.00 120.00  188
  3  ω   -130.00 -82.00   0.50    0.50    --  -54.56 -99.00 150.00   96
  4  ω   -130.00 -82.00   0.50    0.50    --  -54.56 -99.00   0.00   96
  5  ω   -130.00 -82.00   0.50    0.50    --  -54.56 -99.00 -60.00   96
  6  ω   -163.00 -78.00   0.50    2.00    --  -86.25-111.00-150.00  170
  7  ω     98.00 178.00   0.50    2.00    --  107.75 113.00  69.65  160
  8  ω    153.00 178.00   0.50    2.00    --  107.75  45.00  30.00   50
  9  ω    127.00 177.00   0.50    2.00    --  107.75 111.00 -60.00  100
 10  ω    129.00 178.00   0.50    2.00    --  107.75 111.00 -90.00   98
 11  ω    117.00 143.00   0.50    2.00    --  107.75  45.00 -90.00   52
 12  ω    107.00 176.00   0.50    2.00    --  107.75  61.00 -90.00  138
 13  ω     98.00 178.00   0.50    2.00    --  107.75  15.00   0.00  160
 14  ω    100.00 178.00   0.50    2.00    --  107.75  61.00   0.00  156
 15  ω     99.00 134.00   0.50    2.00    --  107.75  15.00  90.00   70
 16  ω    104.00 129.00   0.50    2.00    --  107.75  45.00 150.00   50
 17  ω    131.00 168.00   0.50    2.00    --  107.75  45.00 150.00   74
 18  ω    100.00 126.00   0.50    2.00    --  107.75  45.00  30.00   52
 19  ω     88.00 178.00   0.50    2.00    --  107.75  73.00 -48.67  180
 20  ω     78.00 110.00   0.50    2.00    --  107.75 -78.00  84.85   64
 21  ω     82.00 111.00   0.50    2.00    --  107.75-111.00 120.00   58
 22  ω     54.00  81.00   0.50    2.00    --  107.75 -77.00 120.00   54
 23  ω     53.00  90.00   0.50    2.00    --  107.75-111.00  90.00   74
 24  ω     38.00  67.00   0.50    2.00    --  107.75 -78.00  84.85   58
 25  ω     32.00  58.00   0.50    2.00    --  107.75-111.00 120.00   52
 26  ω     40.00  66.00   0.50    2.00    --  107.75 -61.00 -30.00   52
 27  ω     53.00  79.00   0.50    2.00    --  107.75 -94.00 -60.00   52
 28  ω     85.00 111.00   0.50    2.00    --  107.75-111.00 -90.00   52
 29  ω     78.00 103.00   0.50    2.00    --  107.75 -94.00 -30.00   50
 30  ω     41.00  71.00   0.50    2.00    --  107.75 -61.00-120.00   60
 31  ω     58.00 104.00   0.50    2.00    --  107.75 -77.00-150.00   92
 32  ω     75.00 103.00   0.50    2.00    --  107.75 -94.00-180.00   56
 33  ω     66.00  97.00   0.50    2.00    --  107.75 -77.00-180.00   62
 34  ω     41.00  75.00   0.50    2.00    --  107.75-111.00 -90.00   68
 35  ω     35.00  61.00   0.50    2.00    --  107.75 -55.00-118.00   52
 36  ω     88.00 138.00   0.50    2.00    --  107.75  73.00 179.37  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1538168000
_diffrn_orient_matrix_UB_12      0.0433428000
_diffrn_orient_matrix_UB_13      0.0604804000
_diffrn_orient_matrix_UB_21      0.0473689000
_diffrn_orient_matrix_UB_22      -0.0470466000
_diffrn_orient_matrix_UB_23      0.1552494000
_diffrn_orient_matrix_UB_31      0.0609542000
_diffrn_orient_matrix_UB_32      -0.0728009000
_diffrn_orient_matrix_UB_33      -0.0644067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2798
_reflns_number_total             2920

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.4756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0839
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41975(14) 0.90571(8) 0.40653(15) 0.0302(3) Uani 1 1 d . . . . .
H1A H 0.346606 0.871791 0.323276 0.045 Uiso 1 1 calc GR . . . .
H1B H 0.486103 0.934095 0.367966 0.045 Uiso 1 1 calc GR . . . .
H1C H 0.367439 0.947812 0.441185 0.045 Uiso 1 1 calc GR . . . .
C2 C 0.51126(14) 0.84908(7) 0.54148(14) 0.0263(2) Uani 1 1 d . . . . .
H2A H 0.582988 0.883416 0.627139 0.032 Uiso 1 1 calc R . . . .
H2B H 0.444403 0.819943 0.580114 0.032 Uiso 1 1 calc R . . . .
C3 C 0.63954(12) 0.71429(7) 0.56786(12) 0.0212(2) Uani 1 1 d . . . . .
C4 C 0.73196(12) 0.57441(7) 0.65329(12) 0.0210(2) Uani 1 1 d . . . . .
C5 C 0.79660(12) 0.48687(7) 0.67840(12) 0.0211(2) Uani 1 1 d . . . . .
C6 C 0.71519(14) 0.43205(8) 0.53367(14) 0.0298(3) Uani 1 1 d . . . . .
H6A H 0.607461 0.429291 0.510592 0.036 Uiso 1 1 calc R . . . .
H6B H 0.725594 0.457586 0.443357 0.036 Uiso 1 1 calc R . . . .
C7 C 0.78137(15) 0.34279(8) 0.56100(16) 0.0340(3) Uani 1 1 d . . . . .
H7 H 0.727013 0.307662 0.466733 0.041 Uiso 1 1 calc R . . . .
C8 C 0.94647(17) 0.34728(9) 0.59248(19) 0.0394(3) Uani 1 1 d . . . . .
H8A H 0.957557 0.372639 0.502384 0.047 Uiso 1 1 calc R . . . .
H8B H 0.989360 0.289905 0.608244 0.047 Uiso 1 1 calc R . . . .
C9 C 1.02982(14) 0.40065(8) 0.73747(18) 0.0369(3) Uani 1 1 d . . . . .
H9 H 1.138133 0.403449 0.758583 0.044 Uiso 1 1 calc R . . . .
C10 C 0.96392(13) 0.49008(8) 0.71165(16) 0.0305(3) Uani 1 1 d . . . . .
H10A H 0.976265 0.516545 0.623092 0.037 Uiso 1 1 calc R . . . .
H10B H 1.018225 0.524713 0.805061 0.037 Uiso 1 1 calc R . . . .
C11 C 0.76561(15) 0.30314(8) 0.69995(17) 0.0345(3) Uani 1 1 d . . . . .
H11A H 0.808310 0.245699 0.717331 0.041 Uiso 1 1 calc R . . . .
H11B H 0.658572 0.298850 0.679236 0.041 Uiso 1 1 calc R . . . .
C12 C 0.84708(15) 0.35676(8) 0.84400(15) 0.0314(3) Uani 1 1 d . . . . .
H12 H 0.835708 0.330635 0.934512 0.038 Uiso 1 1 calc R . . . .
C13 C 0.77919(14) 0.44539(8) 0.81653(14) 0.0282(3) Uani 1 1 d . . . . .
H13A H 0.830048 0.480027 0.910719 0.034 Uiso 1 1 calc R . . . .
H13B H 0.671948 0.441955 0.795357 0.034 Uiso 1 1 calc R . . . .
C14 C 1.01257(15) 0.36092(8) 0.87685(17) 0.0375(3) Uani 1 1 d . . . . .
H14A H 1.055731 0.303579 0.895343 0.045 Uiso 1 1 calc R . . . .
H14B H 1.066852 0.395033 0.970974 0.045 Uiso 1 1 calc R . . . .
N1 N 0.59200(11) 0.78731(7) 0.49242(12) 0.0265(2) Uani 1 1 d . . . . .
H1 H 0.5989(18) 0.7935(10) 0.403(2) 0.035(4) Uiso 1 1 d . . . . .
N2 N 0.63208(11) 0.69338(6) 0.69847(11) 0.0247(2) Uani 1 1 d . . . . .
N3 N 0.68498(11) 0.61215(6) 0.74506(11) 0.0247(2) Uani 1 1 d . . . . .
S1 S 0.71497(3) 0.63569(2) 0.49303(3) 0.02678(10) Uani 1 1 d . . . . .


_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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5173(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N1 1.4548(15) . ?
C3 N1 1.3418(15) . ?
C3 N2 1.3125(14) . ?
C3 S1 1.7463(11) . ?
C4 C5 1.5073(15) . ?
C4 N3 1.2892(14) . ?
C4 S1 1.7529(11) . ?
C5 C6 1.5401(15) . ?
C5 C10 1.5427(15) . ?
C5 C13 1.5371(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5377(18) . ?
C7 H7 1.0000 . ?
C7 C8 1.526(2) . ?
C7 C11 1.524(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.532(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.5395(17) . ?
C9 C14 1.535(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5250(19) . ?
C12 H12 1.0000 . ?
C12 C13 1.5344(17) . ?
C12 C14 1.526(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N1 H1 0.884(18) . ?
N2 N3 1.3939(13) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
N1 C2 C1 110.05(10) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
N1 C3 S1 121.04(8) . . ?
N2 C3 N1 125.32(10) . . ?
N2 C3 S1 113.62(8) . . ?
C5 C4 S1 122.18(8) . . ?
N3 C4 C5 124.65(10) . . ?
N3 C4 S1 113.17(8) . . ?
C4 C5 C6 110.62(9) . . ?
C4 C5 C10 110.25(9) . . ?
C4 C5 C13 110.01(9) . . ?
C6 C5 C10 108.53(10) . . ?
C13 C5 C6 108.37(10) . . ?
C13 C5 C10 109.01(9) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 C5 110.16(10) . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7 109.4 . . ?
C8 C7 C6 109.37(11) . . ?
C8 C7 H7 109.4 . . ?
C11 C7 C6 109.86(11) . . ?
C11 C7 H7 109.4 . . ?
C11 C7 C8 109.33(11) . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
C7 C8 C9 109.39(11) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C8 C9 H9 109.5 . . ?
C8 C9 C10 109.59(11) . . ?
C8 C9 C14 109.56(11) . . ?
C10 C9 H9 109.5 . . ?
C14 C9 H9 109.5 . . ?
C14 C9 C10 109.11(12) . . ?
C5 C10 H10A 109.6 . . ?
C5 C10 H10B 109.6 . . ?
C9 C10 C5 110.19(9) . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C7 C11 H11A 109.7 . . ?
C7 C11 H11B 109.7 . . ?
C7 C11 C12 109.77(10) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C11 C12 H12 109.4 . . ?
C11 C12 C13 109.33(10) . . ?
C11 C12 C14 109.10(11) . . ?
C13 C12 H12 109.4 . . ?
C14 C12 H12 109.4 . . ?
C14 C12 C13 110.31(10) . . ?
C5 C13 H13A 109.6 . . ?
C5 C13 H13B 109.6 . . ?
C12 C13 C5 110.14(10) . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C9 C14 H14A 109.8 . . ?
C9 C14 H14B 109.8 . . ?
C12 C14 C9 109.30(10) . . ?
C12 C14 H14A 109.8 . . ?
C12 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C2 N1 H1 120.1(11) . . ?
C3 N1 C2 121.98(10) . . ?
C3 N1 H1 117.3(11) . . ?
C3 N2 N3 111.96(9) . . ?
C4 N3 N2 114.11(9) . . ?
C3 S1 C4 87.14(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N2 0.884(18) 2.103(18) 2.9859(14) 175.8(15) 4_575 yes
N1 H1 N3 0.884(18) 2.500(17) 3.2647(14) 145.0(14) 4_575 yes

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
C1 C2 N1 C3 -157.26(11) . . . . ?
C3 N2 N3 C4 0.84(14) . . . . ?
C4 C5 C6 C7 -179.64(10) . . . . ?
C4 C5 C10 C9 179.93(10) . . . . ?
C4 C5 C13 C12 -179.12(9) . . . . ?
C5 C4 N3 N2 179.06(9) . . . . ?
C5 C4 S1 C3 -179.53(9) . . . . ?
C5 C6 C7 C8 -60.70(14) . . . . ?
C5 C6 C7 C11 59.30(14) . . . . ?
C6 C5 C10 C9 -58.77(13) . . . . ?
C6 C5 C13 C12 59.82(12) . . . . ?
C6 C7 C8 C9 60.50(14) . . . . ?
C6 C7 C11 C12 -59.36(14) . . . . ?
C7 C8 C9 C10 -60.10(15) . . . . ?
C7 C8 C9 C14 59.59(14) . . . . ?
C7 C11 C12 C13 59.90(14) . . . . ?
C7 C11 C12 C14 -60.82(13) . . . . ?
C8 C7 C11 C12 60.67(14) . . . . ?
C8 C9 C10 C5 59.67(14) . . . . ?
C8 C9 C14 C12 -59.83(14) . . . . ?
C10 C5 C6 C7 59.29(13) . . . . ?
C10 C5 C13 C12 -58.12(13) . . . . ?
C10 C9 C14 C12 60.15(14) . . . . ?
C11 C7 C8 C9 -59.82(14) . . . . ?
C11 C12 C13 C5 -60.69(13) . . . . ?
C11 C12 C14 C9 60.16(13) . . . . ?
C13 C5 C6 C7 -58.97(13) . . . . ?
C13 C5 C10 C9 59.08(13) . . . . ?
C13 C12 C14 C9 -59.96(14) . . . . ?
C14 C9 C10 C5 -60.30(14) . . . . ?
C14 C12 C13 C5 59.29(14) . . . . ?
N1 C3 N2 N3 177.61(11) . . . . ?
N1 C3 S1 C4 -178.04(10) . . . . ?
N2 C3 N1 C2 -6.50(18) . . . . ?
N2 C3 S1 C4 0.46(9) . . . . ?
N3 C4 C5 C6 127.09(12) . . . . ?
N3 C4 C5 C10 -112.87(12) . . . . ?
N3 C4 C5 C13 7.39(15) . . . . ?
N3 C4 S1 C3 0.03(9) . . . . ?
S1 C3 N1 C2 171.81(9) . . . . ?
S1 C3 N2 N3 -0.81(12) . . . . ?
S1 C4 C5 C6 -53.40(12) . . . . ?
S1 C4 C5 C10 66.64(11) . . . . ?
S1 C4 C5 C13 -173.10(8) . . . . ?
S1 C4 N3 N2 -0.49(12) . . . . ?

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1977750'
loop_
_audit_author_name
_audit_author_address
'O. Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-01-15 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 F N3 S'
_chemical_formula_weight         329.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7254(7)
_cell_length_b                   10.9787(5)
_cell_length_c                   11.9955(10)
_cell_angle_alpha                116.607(6)
_cell_angle_beta                 94.587(8)
_cell_angle_gamma                90.941(6)
_cell_volume                     788.01(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    7073
_cell_measurement_theta_max      78.9280
_cell_measurement_theta_min      4.0800

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.934
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            12473
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.142
_diffrn_reflns_theta_max         74.499
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3183
_reflns_number_gt                2735
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0985P)²+1.4753P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3183
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.2034
_refine_ls_wR_factor_gt          0.1988
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8302(7) -0.0933(4) 0.3319(4) 0.0425(9) Uani 1 1 d . . . . .
C2 C 0.6639(6) -0.0246(4) 0.3725(4) 0.0423(9) Uani 1 1 d . . . . .
H2 H 0.540827 -0.072330 0.365541 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6775(6) 0.1183(4) 0.4250(3) 0.0348(8) Uani 1 1 d . . . . .
H3 H 0.562372 0.168180 0.452651 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8579(5) 0.1864(3) 0.4365(3) 0.0299(7) Uani 1 1 d . . . . .
C5 C 1.0255(6) 0.1123(4) 0.3932(3) 0.0372(8) Uani 1 1 d . . . . .
H5 H 1.149519 0.158965 0.399964 0.045 Uiso 1 1 calc R U . . .
C6 C 1.0119(7) -0.0286(4) 0.3406(4) 0.0442(9) Uani 1 1 d . . . . .
H6 H 1.125515 -0.079671 0.311216 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7644(5) 0.4250(3) 0.5615(3) 0.0289(7) Uani 1 1 d . . . . .
C8 C 0.5616(5) 0.5764(3) 0.7165(3) 0.0271(7) Uani 1 1 d . . . . .
C9 C 0.4269(5) 0.6451(3) 0.8181(3) 0.0262(6) Uani 1 1 d . . . . .
C10 C 0.2175(5) 0.5712(3) 0.7795(3) 0.0303(7) Uani 1 1 d . . . . .
H10A H 0.159190 0.572279 0.701521 0.036 Uiso 1 1 calc R U . . .
H10B H 0.228344 0.474865 0.762957 0.036 Uiso 1 1 calc R U . . .
C11 C 0.0810(5) 0.6416(4) 0.8839(4) 0.0353(8) Uani 1 1 d . . . . .
H11 H -0.054527 0.593268 0.857900 0.042 Uiso 1 1 calc R U . . .
C12 C 0.1702(5) 0.6379(4) 1.0040(4) 0.0360(8) Uani 1 1 d . . . . .
H12A H 0.081459 0.682054 1.071368 0.043 Uiso 1 1 calc R U . . .
H12B H 0.181594 0.542050 0.988871 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3770(5) 0.7129(4) 1.0443(3) 0.0338(7) Uani 1 1 d . . . . .
H13 H 0.434949 0.710825 1.122738 0.041 Uiso 1 1 calc R U . . .
C14 C 0.5137(5) 0.6424(4) 0.9401(3) 0.0304(7) Uani 1 1 d . . . . .
H14A H 0.526802 0.546723 0.925089 0.036 Uiso 1 1 calc R U . . .
H14B H 0.648352 0.689560 0.966364 0.036 Uiso 1 1 calc R U . . .
C15 C 0.0641(5) 0.7899(4) 0.9076(4) 0.0399(8) Uani 1 1 d . . . . .
H15A H -0.025505 0.836010 0.974036 0.048 Uiso 1 1 calc R U . . .
H15B H 0.006256 0.792541 0.830246 0.048 Uiso 1 1 calc R U . . .
C16 C 0.2714(5) 0.8639(3) 0.9479(4) 0.0355(8) Uani 1 1 d . . . . .
H16 H 0.259316 0.960801 0.963662 0.043 Uiso 1 1 calc R U . . .
C17 C 0.4080(5) 0.7943(3) 0.8436(3) 0.0306(7) Uani 1 1 d . . . . .
H17A H 0.541692 0.842887 0.868998 0.037 Uiso 1 1 calc R U . . .
H17B H 0.351845 0.797946 0.766375 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3604(6) 0.8612(4) 1.0677(3) 0.0375(8) Uani 1 1 d . . . . .
H18A H 0.274058 0.908337 1.135857 0.045 Uiso 1 1 calc R U . . .
H18B H 0.494324 0.909347 1.093718 0.045 Uiso 1 1 calc R U . . .
F1 F 0.8171(5) -0.2327(2) 0.2803(3) 0.0692(9) Uani 1 1 d . . . . .
N1 N 0.8818(4) 0.3287(3) 0.4849(3) 0.0322(6) Uani 1 1 d . . . . .
H1 H 0.994(6) 0.364(4) 0.466(4) 0.031(10) Uiso 1 1 d . . . . .
N2 N 0.7814(4) 0.5499(3) 0.5773(3) 0.0301(6) Uani 1 1 d . . . . .
N3 N 0.6645(4) 0.6371(3) 0.6669(3) 0.0301(6) Uani 1 1 d . . . . .
S1 S 0.59776(13) 0.40117(8) 0.65452(8) 0.0323(3) Uani 1 1 d . . . . .


_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
C1 C2 1.357(6) . ?
C1 F1 1.368(4) . ?
C1 C6 1.375(6) . ?
C2 C3 1.402(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(5) . ?
C4 N1 1.404(4) . ?
C5 C6 1.383(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.299(4) . ?
C7 N1 1.363(4) . ?
C7 S1 1.738(3) . ?
C8 N3 1.298(4) . ?
C8 C9 1.500(4) . ?
C8 S1 1.754(3) . ?
C9 C17 1.535(4) . ?
C9 C10 1.542(4) . ?
C9 C14 1.545(5) . ?
C10 C11 1.533(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.530(5) . ?
C11 C12 1.533(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.531(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.530(5) . ?
C13 C14 1.531(5) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.530(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.525(5) . ?
C16 C17 1.530(5) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N1 H1 0.93(4) . ?
N2 N3 1.388(4) . ?

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
C2 C1 F1 118.7(4) . . ?
C2 C1 C6 122.8(4) . . ?
F1 C1 C6 118.5(4) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 N1 123.3(3) . . ?
C5 C4 N1 117.0(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 118.5(4) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N2 C7 N1 120.5(3) . . ?
N2 C7 S1 113.6(2) . . ?
N1 C7 S1 125.7(3) . . ?
N3 C8 C9 125.2(3) . . ?
N3 C8 S1 113.0(2) . . ?
C9 C8 S1 121.8(2) . . ?
C8 C9 C17 110.0(3) . . ?
C8 C9 C10 110.4(3) . . ?
C17 C9 C10 109.1(3) . . ?
C8 C9 C14 110.1(3) . . ?
C17 C9 C14 108.7(3) . . ?
C10 C9 C14 108.5(3) . . ?
C11 C10 C9 110.1(3) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C15 C11 C10 109.0(3) . . ?
C15 C11 C12 109.6(3) . . ?
C10 C11 C12 109.5(3) . . ?
C15 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
C12 C11 H11 109.6 . . ?
C13 C12 C11 109.5(3) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C18 C13 C12 110.0(3) . . ?
C18 C13 C14 109.0(3) . . ?
C12 C13 C14 109.3(3) . . ?
C18 C13 H13 109.5 . . ?
C12 C13 H13 109.5 . . ?
C14 C13 H13 109.5 . . ?
C13 C14 C9 110.3(3) . . ?
C13 C14 H14A 109.6 . . ?
C9 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C9 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C11 C15 C16 109.5(3) . . ?
C11 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
C11 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C18 C16 C15 110.0(3) . . ?
C18 C16 C17 109.7(3) . . ?
C15 C16 C17 109.6(3) . . ?
C18 C16 H16 109.2 . . ?
C15 C16 H16 109.2 . . ?
C17 C16 H16 109.2 . . ?
C16 C17 C9 109.6(3) . . ?
C16 C17 H17A 109.7 . . ?
C9 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
C9 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C16 C18 C13 109.3(3) . . ?
C16 C18 H18A 109.8 . . ?
C13 C18 H18A 109.8 . . ?
C16 C18 H18B 109.8 . . ?
C13 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
C7 N1 C4 128.2(3) . . ?
C7 N1 H1 114(2) . . ?
C4 N1 H1 117(2) . . ?
C7 N2 N3 113.0(3) . . ?
C8 N3 N2 113.2(3) . . ?
C7 S1 C8 87.14(15) . . ?

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
F1 C1 C2 C3 -179.8(3) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C2 C3 C4 N1 178.2(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
N1 C4 C5 C6 -177.9(3) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
F1 C1 C6 C5 -179.7(4) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
N3 C8 C9 C17 7.0(5) . . . . ?
S1 C8 C9 C17 -174.2(2) . . . . ?
N3 C8 C9 C10 127.5(3) . . . . ?
S1 C8 C9 C10 -53.7(4) . . . . ?
N3 C8 C9 C14 -112.7(4) . . . . ?
S1 C8 C9 C14 66.1(3) . . . . ?
C8 C9 C10 C11 179.8(3) . . . . ?
C17 C9 C10 C11 -59.2(4) . . . . ?
C14 C9 C10 C11 59.0(4) . . . . ?
C9 C10 C11 C15 59.8(4) . . . . ?
C9 C10 C11 C12 -60.1(4) . . . . ?
C15 C11 C12 C13 -59.3(4) . . . . ?
C10 C11 C12 C13 60.3(4) . . . . ?
C11 C12 C13 C18 59.4(4) . . . . ?
C11 C12 C13 C14 -60.3(4) . . . . ?
C18 C13 C14 C9 -60.0(4) . . . . ?
C12 C13 C14 C9 60.3(4) . . . . ?
C8 C9 C14 C13 179.8(3) . . . . ?
C17 C9 C14 C13 59.3(3) . . . . ?
C10 C9 C14 C13 -59.2(3) . . . . ?
C10 C11 C15 C16 -60.3(4) . . . . ?
C12 C11 C15 C16 59.5(4) . . . . ?
C11 C15 C16 C18 -59.9(4) . . . . ?
C11 C15 C16 C17 60.8(4) . . . . ?
C18 C16 C17 C9 60.7(4) . . . . ?
C15 C16 C17 C9 -60.2(4) . . . . ?
C8 C9 C17 C16 -179.7(3) . . . . ?
C10 C9 C17 C16 59.0(4) . . . . ?
C14 C9 C17 C16 -59.1(3) . . . . ?
C15 C16 C18 C13 59.7(4) . . . . ?
C17 C16 C18 C13 -61.0(4) . . . . ?
C12 C13 C18 C16 -59.5(4) . . . . ?
C14 C13 C18 C16 60.4(4) . . . . ?
N2 C7 N1 C4 -165.6(3) . . . . ?
S1 C7 N1 C4 19.7(5) . . . . ?
C3 C4 N1 C7 22.3(6) . . . . ?
C5 C4 N1 C7 -160.8(3) . . . . ?
N1 C7 N2 N3 -174.3(3) . . . . ?
S1 C7 N2 N3 1.0(4) . . . . ?
C9 C8 N3 N2 178.2(3) . . . . ?
S1 C8 N3 N2 -0.7(4) . . . . ?
C7 N2 N3 C8 -0.2(4) . . . . ?
N2 C7 S1 C8 -1.1(3) . . . . ?
N1 C7 S1 C8 173.9(3) . . . . ?
N3 C8 S1 C7 1.0(3) . . . . ?
C9 C8 S1 C7 -177.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N2 0.93(4) 1.99(4) 2.920(4) 175(4) 2_766 yes

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_emam06
_database_code_depnum_ccdc_archive 'CCDC 1977643'
loop_
_audit_author_name
_audit_author_address
'O. Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-01-14 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_date             2019-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Br N3 S'
_chemical_formula_sum            'C18 H20 Br N3 S'
_chemical_formula_weight         390.34
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7648(2)
_cell_length_b                   11.4551(2)
_cell_length_c                   11.4985(2)
_cell_angle_alpha                110.417(2)
_cell_angle_beta                 95.240(2)
_cell_angle_gamma                93.613(2)
_cell_volume                     827.26(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12771
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.8960
_cell_measurement_theta_min      4.0940
_shelx_estimated_absorpt_T_max   0.711
_shelx_estimated_absorpt_T_min   0.361
_exptl_absorpt_coefficient_mu    4.574
_exptl_absorpt_correction_T_max  0.767
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0481
0 1 0 0.0574
0 0 -1 0.0492
0 0 1 0.0328
-1 2 -5 0.0422
2 1 -2 0.1122
2 1 1 0.1036
3 -5 2 0.0723
2 -2 -1 0.0839
2 -2 1 0.0773
-3 2 -5 0.0978
0 -5 4 0.0494
0 1 -1 0.0451
-3 -5 3 0.0981

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08

_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14178
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         4.133
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -124.00 -38.00   0.50    0.25    --  -51.56 -57.00 120.00  172
  2  ω   -127.00 -82.00   0.50    0.25    --  -51.56 -99.00-180.00   90
  3  ω   -127.00 -82.00   0.50    0.25    --  -51.56 -99.00 120.00   90
  4  ω    -92.00  -9.00   0.50    0.25    --  -51.56 125.00-180.00  166
  5  ω    -27.00  26.00   0.50    0.25    --   51.56 -19.00 -60.00  106
  6  ω   -157.00 -71.00   0.50    0.25    --  -86.25 -61.00  60.00  172
  7  ω     35.00 105.00   0.50    0.25    --  107.75 -77.00 -90.00  140
  8  ω     99.00 178.00   0.50    0.25    --  107.75 111.00 150.00  158
  9  ω     93.00 178.00   0.50    0.25    --  107.75  61.00-120.00  170
 10  ω     31.00 112.00   0.50    0.25    --  107.75-111.00-150.00  162
 11  ω     86.00 178.00   0.50    0.25    --  107.75  77.00 -90.00  184
 12  ω     37.00  71.00   0.50    0.25    --  107.75 -61.00  30.00   68
 13  ω     31.00 112.00   0.50    0.25    --  107.75-111.00 120.00  162
 14  ω     31.00 112.00   0.50    0.25    --  107.75-111.00  90.00  162
 15  ω     37.00  71.00   0.50    0.25    --  107.75 -61.00 150.00   68
 16  ω     35.00 105.00   0.50    0.25    --  107.75 -77.00-150.00  140
 17  ω     37.00  71.00   0.50    0.25    --  107.75 -61.00  60.00   68
 18  ω     37.00  71.00   0.50    0.25    --  107.75 -61.00  90.00   68
 19  ω     30.00 124.00   0.50    0.25    --   51.56  77.00 -60.00  188
 20  ω     42.00 128.00   0.50    0.25    --   51.56  38.00-120.00  172
 21  ω   -120.00 -94.00   0.50    0.25    --  -54.56 -38.00  30.00   52
 22  ω    -76.00 -48.00   0.50    0.25    --  -54.56 -38.00  30.00   56
 23  ω    -37.00  -3.00   0.50    0.25    --  -54.56  38.00-180.00   68
 24  ω   -115.00 -82.00   0.50    0.25    --  -86.25-111.00 -30.00   66
 25  ω   -157.00-131.00   0.50    0.25    --  -86.25-111.00 -30.00   52
 26  ω     51.00  77.00   0.50    0.25    --  107.75 -77.00 150.00   52
 27  ω     37.00  63.00   0.50    0.25    --  107.75 -61.00-150.00   52
 28  ω     39.00  71.00   0.50    0.25    --  107.75 -61.00 -30.00   64
 29  ω     78.00 109.00   0.50    0.25    --  107.75-111.00  30.00   62
 30  ω     34.00  60.00   0.50    0.25    --  107.75-111.00  30.00   52
 31  ω    129.00 177.00   0.50    0.25    --  107.75  77.00 120.00   96
 32  ω     75.00 105.00   0.50    0.25    --  107.75 -94.00-150.00   60
 33  ω     75.00 108.00   0.50    0.25    --  107.75 -94.00 120.00   66
 34  ω    109.00 135.00   0.50    0.25    --  107.75  15.00-180.00   52
 35  ω     36.00  71.00   0.50    0.25    --  107.75 -94.00-150.00   70
 36  ω    137.00 163.00   0.50    0.25    --  107.75  15.00-180.00   52
 37  ω     86.00 117.00   0.50    0.25    --  107.75  77.00 120.00   62
 38  ω     32.00  68.00   0.50    0.25    --  107.75-111.00 -30.00   72
 39  ω     82.00 107.00   0.50    0.25    --  107.75-111.00 -30.00   50
 40  ω    121.00 172.00   0.50    0.25    --  107.75  15.00  60.00  102
 41  ω     87.00 113.00   0.50    0.25    --  107.75-112.00 -16.91   52
 42  ω    110.00 135.00   0.50    0.25    --  107.75 111.00 -60.00   50
 43  ω     31.00  81.00   0.50    0.25    --  107.75-112.00 -16.91  100
 44  ω   -127.00 -33.00   0.50    0.25    --  -54.56 -77.00-150.00  188
 45  ω   -127.00 -44.00   0.50    0.25    --  -54.56 -77.00 120.00  166
 46  ω   -127.00 -41.00   0.50    0.25    --  -54.56 -57.00   0.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0363154000
_diffrn_orient_matrix_UB_12      0.1349992000
_diffrn_orient_matrix_UB_13      0.0123138000
_diffrn_orient_matrix_UB_21      0.2174866000
_diffrn_orient_matrix_UB_22      0.0247806000
_diffrn_orient_matrix_UB_23      -0.0218877000
_diffrn_orient_matrix_UB_31      -0.0650032000
_diffrn_orient_matrix_UB_32      -0.0443715000
_diffrn_orient_matrix_UB_33      -0.1418147000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3269
_reflns_number_total             3385

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.3959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0614
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,
 H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.83080(3) 0.90939(2) 0.06280(2) 0.03484(7) Uani 1 1 d . . . . .
C1 C 0.6416(2) 0.91064(15) 0.17562(15) 0.0281(3) Uani 1 1 d . . . . .
C2 C 0.6782(3) 0.85476(18) 0.26281(19) 0.0402(4) Uani 1 1 d . . . . .
H2 H 0.797804 0.816399 0.266985 0.048 Uiso 1 1 calc R . . . .
C3 C 0.5393(3) 0.85483(19) 0.34450(19) 0.0426(5) Uani 1 1 d . . . . .
H3 H 0.564356 0.816671 0.404934 0.051 Uiso 1 1 calc R . . . .
C4 C 0.3637(3) 0.91041(15) 0.33842(15) 0.0287(3) Uani 1 1 d . . . . .
C5 C 0.3326(2) 0.96962(15) 0.25186(15) 0.0277(3) Uani 1 1 d . . . . .
H5 H 0.215566 1.010715 0.249112 0.033 Uiso 1 1 calc R . . . .
C6 C 0.4703(2) 0.96913(15) 0.17009(14) 0.0275(3) Uani 1 1 d . . . . .
H6 H 0.447382 1.008644 0.110587 0.033 Uiso 1 1 calc R . . . .
C7 C 0.1853(3) 0.85647(15) 0.49791(15) 0.0291(3) Uani 1 1 d . . . . .
C8 C 0.1634(2) 0.73985(14) 0.63542(14) 0.0249(3) Uani 1 1 d . . . . .
C9 C 0.1911(2) 0.65911(14) 0.71389(14) 0.0236(3) Uani 1 1 d . . . . .
C10 C 0.2181(3) 0.52365(14) 0.63222(15) 0.0301(3) Uani 1 1 d . . . . .
H10A H 0.100522 0.488242 0.568475 0.036 Uiso 1 1 calc R . . . .
H10B H 0.337552 0.523089 0.588350 0.036 Uiso 1 1 calc R . . . .
C11 C 0.2423(3) 0.44329(15) 0.71399(16) 0.0320(3) Uani 1 1 d . . . . .
H11 H 0.257361 0.355313 0.659914 0.038 Uiso 1 1 calc R . . . .
C12 C 0.4281(3) 0.49572(17) 0.80901(17) 0.0354(4) Uani 1 1 d . . . . .
H12A H 0.547511 0.494570 0.765006 0.043 Uiso 1 1 calc R . . . .
H12B H 0.446189 0.443407 0.861149 0.043 Uiso 1 1 calc R . . . .
C13 C 0.4038(3) 0.63023(17) 0.89186(16) 0.0336(4) Uani 1 1 d . . . . .
H13 H 0.525120 0.664901 0.954377 0.040 Uiso 1 1 calc R . . . .
C14 C 0.3777(3) 0.71189(16) 0.81119(16) 0.0311(3) Uani 1 1 d . . . . .
H14A H 0.497257 0.713156 0.767863 0.037 Uiso 1 1 calc R . . . .
H14B H 0.363028 0.798887 0.865151 0.037 Uiso 1 1 calc R . . . .
C15 C 0.0588(3) 0.44431(16) 0.78295(17) 0.0352(4) Uani 1 1 d . . . . .
H15A H -0.061831 0.408920 0.721683 0.042 Uiso 1 1 calc R . . . .
H15B H 0.074642 0.391936 0.835189 0.042 Uiso 1 1 calc R . . . .
C16 C 0.0346(3) 0.57862(17) 0.86544(17) 0.0329(4) Uani 1 1 d . . . . .
H16 H -0.085190 0.579182 0.910448 0.039 Uiso 1 1 calc R . . . .
C17 C 0.0073(2) 0.65832(16) 0.78297(16) 0.0308(3) Uani 1 1 d . . . . .
H17A H -0.113227 0.623629 0.721529 0.037 Uiso 1 1 calc R . . . .
H17B H -0.011422 0.745075 0.835585 0.037 Uiso 1 1 calc R . . . .
C18 C 0.2203(3) 0.63148(17) 0.96042(16) 0.0362(4) Uani 1 1 d . . . . .
H18A H 0.236806 0.580356 1.013876 0.043 Uiso 1 1 calc R . . . .
H18B H 0.205405 0.718287 1.014763 0.043 Uiso 1 1 calc R . . . .
N1 N 0.2139(2) 0.91536(14) 0.41582(14) 0.0355(3) Uani 1 1 d . . . . .
H1 H 0.133(3) 0.967(2) 0.418(2) 0.045(6) Uiso 1 1 d . . . . .
N2 N 0.0319(2) 0.87837(14) 0.56178(15) 0.0376(4) Uani 1 1 d . . . . .
N3 N 0.0213(2) 0.81100(13) 0.64046(14) 0.0328(3) Uani 1 1 d . . . . .
S1 S 0.32987(6) 0.74907(3) 0.52987(3) 0.02671(9) Uani 1 1 d . . . . .


_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
Br1 C1 1.9009(16) . ?
C1 C2 1.378(2) . ?
C1 C6 1.382(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 C5 1.395(2) . ?
C4 N1 1.400(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9500 . ?
C7 N1 1.358(2) . ?
C7 N2 1.312(2) . ?
C7 S1 1.7341(15) . ?
C8 C9 1.5093(19) . ?
C8 N3 1.291(2) . ?
C8 S1 1.7540(15) . ?
C9 C10 1.541(2) . ?
C9 C14 1.544(2) . ?
C9 C17 1.536(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.534(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.527(2) . ?
C11 C15 1.532(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.531(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.537(2) . ?
C13 C18 1.528(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.528(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.536(2) . ?
C16 C18 1.526(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N1 H1 0.83(2) . ?
N2 N3 1.3825(18) . ?

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
C2 C1 Br1 119.65(12) . . ?
C2 C1 C6 120.88(15) . . ?
C6 C1 Br1 119.47(12) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.62(16) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.39(16) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.96(15) . . ?
C3 C4 N1 125.01(14) . . ?
C5 C4 N1 116.00(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.69(14) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.41(14) . . ?
C5 C6 H6 120.3 . . ?
N1 C7 S1 127.31(12) . . ?
N2 C7 N1 119.46(14) . . ?
N2 C7 S1 113.22(11) . . ?
C9 C8 S1 122.30(11) . . ?
N3 C8 C9 124.60(14) . . ?
N3 C8 S1 113.07(11) . . ?
C8 C9 C10 111.11(12) . . ?
C8 C9 C14 110.09(13) . . ?
C8 C9 C17 109.35(12) . . ?
C10 C9 C14 108.32(13) . . ?
C17 C9 C10 109.08(13) . . ?
C17 C9 C14 108.85(13) . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 C9 109.99(13) . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C10 C11 H11 109.3 . . ?
C12 C11 C10 109.36(14) . . ?
C12 C11 H11 109.3 . . ?
C12 C11 C15 109.46(14) . . ?
C15 C11 C10 110.04(13) . . ?
C15 C11 H11 109.3 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C11 C12 C13 109.08(13) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
C12 C13 H13 109.3 . . ?
C12 C13 C14 109.94(14) . . ?
C14 C13 H13 109.3 . . ?
C18 C13 C12 109.70(14) . . ?
C18 C13 H13 109.3 . . ?
C18 C13 C14 109.13(14) . . ?
C9 C14 H14A 109.7 . . ?
C9 C14 H14B 109.7 . . ?
C13 C14 C9 109.89(13) . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C11 C15 H15A 109.8 . . ?
C11 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 C11 109.54(13) . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C15 C16 H16 109.5 . . ?
C15 C16 C17 109.18(14) . . ?
C17 C16 H16 109.5 . . ?
C18 C16 C15 109.23(14) . . ?
C18 C16 H16 109.5 . . ?
C18 C16 C17 109.97(14) . . ?
C9 C17 C16 110.09(13) . . ?
C9 C17 H17A 109.6 . . ?
C9 C17 H17B 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
C13 C18 H18A 109.8 . . ?
C13 C18 H18B 109.8 . . ?
C16 C18 C13 109.59(14) . . ?
C16 C18 H18A 109.8 . . ?
C16 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C4 N1 H1 116.1(16) . . ?
C7 N1 C4 131.10(14) . . ?
C7 N1 H1 112.6(16) . . ?
C7 N2 N3 112.85(13) . . ?
C8 N3 N2 113.54(13) . . ?
C7 S1 C8 87.31(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 S1 0.95 2.49 3.1867(18) 129.8 . yes
N1 H1 N2 0.83(2) 2.10(2) 2.9264(19) 170(2) 2_576 yes

