# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_an172_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2431131'
loop_
_audit_author_name
_audit_author_address
'Shruti Sangwan'
;University of Hyderabad
India
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
_audit_creation_date             2025-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N3 O S'
_chemical_formula_sum            'C17 H21 N3 O S'
_chemical_formula_weight         315.43
_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 0.0033 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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.7047(9)
_cell_length_b                   8.0199(5)
_cell_length_c                   16.4944(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.648(3)
_cell_angle_gamma                90
_cell_volume                     1618.33(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3201
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      0.962
_cell_measurement_theta_min      0.952
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_preparation       'nitro methane'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23713
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.360
_diffrn_ambient_temperature      295.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3201
_reflns_number_total             3729
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0819
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²+3.2181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2349
_refine_ls_wR_factor_ref         0.2389
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C9(H9), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.42001(7) 0.35186(12) 0.39603(6) 0.0422(3) Uani 1 1 d . . . . .
O1 O 0.2003(2) 0.6759(4) 0.3044(2) 0.0653(9) Uani 1 1 d . . . . .
N2 N 0.2071(2) 0.4068(4) 0.3528(2) 0.0470(8) Uani 1 1 d . . . . .
N3 N 0.8816(3) 0.6843(5) 0.3353(2) 0.0489(8) Uani 1 1 d . . . . .
N1 N 0.2600(3) 0.1421(4) 0.4055(3) 0.0530(9) Uani 1 1 d . . . . .
C10 C 0.5496(3) 0.6721(4) 0.3352(2) 0.0356(7) Uani 1 1 d . . . . .
C14 C 0.7380(3) 0.5862(4) 0.3947(2) 0.0382(7) Uani 1 1 d . . . . .
H14 H 0.7885 0.5251 0.4351 0.046 Uiso 1 1 calc R . . . .
C13 C 0.7742(3) 0.6840(5) 0.3367(2) 0.0388(8) Uani 1 1 d . . . . .
C15 C 0.6293(3) 0.5793(4) 0.3927(2) 0.0376(7) Uani 1 1 d . . . . .
H15 H 0.6079 0.5109 0.4309 0.045 Uiso 1 1 calc R . . . .
C9 C 0.4337(3) 0.6649(5) 0.3274(2) 0.0403(8) Uani 1 1 d . . . . .
H9 H 0.3940 0.7578 0.3026 0.048 Uiso 1 1 calc R . . . .
C8 C 0.3747(3) 0.5446(5) 0.3507(2) 0.0383(7) Uani 1 1 d . . . . .
C6 C 0.2820(3) 0.2944(5) 0.3836(2) 0.0416(8) Uani 1 1 d . . . . .
C7 C 0.2522(3) 0.5524(5) 0.3331(2) 0.0443(8) Uani 1 1 d . . . . .
C11 C 0.5877(3) 0.7781(5) 0.2815(2) 0.0440(8) Uani 1 1 d . . . . .
H11 H 0.5382 0.8476 0.2449 0.053 Uiso 1 1 calc R . . . .
C12 C 0.6956(3) 0.7827(5) 0.2812(2) 0.0452(9) Uani 1 1 d . . . . .
H12 H 0.7170 0.8525 0.2435 0.054 Uiso 1 1 calc R . . . .
C17 C 0.9617(3) 0.5886(6) 0.3957(3) 0.0516(10) Uani 1 1 d . . . . .
H17A H 0.9679 0.6309 0.4513 0.077 Uiso 1 1 calc GR . . . .
H17B H 1.0312 0.5973 0.3834 0.077 Uiso 1 1 calc GR . . . .
H17C H 0.9395 0.4739 0.3928 0.077 Uiso 1 1 calc GR . . . .
C5 C 0.1472(3) 0.0828(6) 0.3916(3) 0.0613(12) Uani 1 1 d . . . . .
H5A H 0.1316 -0.0010 0.3475 0.074 Uiso 1 1 calc R . . . .
H5B H 0.0969 0.1749 0.3733 0.074 Uiso 1 1 calc R . . . .
C4 C 0.1310(4) 0.0095(7) 0.4712(3) 0.0658(13) Uani 1 1 d . . . . .
H4A H 0.0583 -0.0380 0.4598 0.079 Uiso 1 1 calc R . . . .
H4B H 0.1367 0.0973 0.5127 0.079 Uiso 1 1 calc R . . . .
C16 C 0.9160(3) 0.7771(7) 0.2719(3) 0.0649(13) Uani 1 1 d . . . . .
H16A H 0.8752 0.7405 0.2170 0.097 Uiso 1 1 calc GR . . . .
H16B H 0.9925 0.7588 0.2785 0.097 Uiso 1 1 calc GR . . . .
H16C H 0.9031 0.8938 0.2779 0.097 Uiso 1 1 calc GR . . . .
C1 C 0.3422(4) 0.0133(6) 0.4377(4) 0.0745(16) Uani 1 1 d . . . . .
H1A H 0.4147 0.0608 0.4470 0.089 Uiso 1 1 calc R . . . .
H1B H 0.3345 -0.0752 0.3964 0.089 Uiso 1 1 calc R . . . .
C3 C 0.2152(4) -0.1248(7) 0.5070(4) 0.0731(14) Uani 1 1 d . . . . .
H3A H 0.2067 -0.1625 0.5608 0.088 Uiso 1 1 calc R . . . .
H3B H 0.2036 -0.2195 0.4690 0.088 Uiso 1 1 calc R . . . .
C2 C 0.3292(5) -0.0572(8) 0.5185(4) 0.0842(18) Uani 1 1 d . . . . .
H2A H 0.3435 0.0292 0.5613 0.101 Uiso 1 1 calc R . . . .
H2B H 0.3820 -0.1458 0.5376 0.101 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 C8 1.746(4) . ?
S1 C6 1.770(3) . ?
O1 C7 1.213(5) . ?
N2 C6 1.310(5) . ?
N2 C7 1.378(5) . ?
N3 C13 1.371(5) . ?
N3 C17 1.439(5) . ?
N3 C16 1.444(5) . ?
N1 C6 1.325(5) . ?
N1 C5 1.468(5) . ?
N1 C1 1.463(6) . ?
C10 C15 1.400(5) . ?
C10 C9 1.445(5) . ?
C10 C11 1.405(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.407(5) . ?
C14 C15 1.374(5) . ?
C13 C12 1.403(5) . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.339(5) . ?
C8 C7 1.506(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(5) . ?
C12 H12 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.503(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.520(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.497(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.510(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 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
C8 S1 C6 88.82(17) . . ?
C6 N2 C7 111.7(3) . . ?
C13 N3 C17 120.5(3) . . ?
C13 N3 C16 120.7(3) . . ?
C17 N3 C16 118.8(3) . . ?
C6 N1 C5 121.7(4) . . ?
C6 N1 C1 124.5(3) . . ?
C1 N1 C5 113.5(3) . . ?
C15 C10 C9 124.9(3) . . ?
C15 C10 C11 116.1(3) . . ?
C11 C10 C9 119.0(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C15 C14 C13 121.1(3) . . ?
N3 C13 C14 121.5(3) . . ?
N3 C13 C12 121.6(3) . . ?
C12 C13 C14 116.9(3) . . ?
C10 C15 H15 118.9 . . ?
C14 C15 C10 122.2(3) . . ?
C14 C15 H15 118.9 . . ?
C10 C9 H9 115.2 . . ?
C8 C9 C10 129.7(3) . . ?
C8 C9 H9 115.2 . . ?
C9 C8 S1 128.0(3) . . ?
C9 C8 C7 122.9(3) . . ?
C7 C8 S1 108.9(3) . . ?
N2 C6 S1 117.3(3) . . ?
N2 C6 N1 123.7(3) . . ?
N1 C6 S1 119.0(3) . . ?
O1 C7 N2 124.6(3) . . ?
O1 C7 C8 122.3(4) . . ?
N2 C7 C8 113.1(3) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.2(3) . . ?
C12 C11 H11 118.9 . . ?
C13 C12 H12 119.4 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
N1 C5 C4 110.3(4) . . ?
H5A C5 H5B 108.1 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C5 C4 C3 111.6(4) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 C2 110.5(4) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C2 C3 C4 110.2(4) . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C1 C2 C3 110.8(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 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
S1 C8 C7 O1 177.2(4) . . . . ?
S1 C8 C7 N2 -2.9(4) . . . . ?
N3 C13 C12 C11 178.2(4) . . . . ?
N1 C5 C4 C3 -53.9(6) . . . . ?
N1 C1 C2 C3 56.5(6) . . . . ?
C10 C9 C8 S1 -2.0(6) . . . . ?
C10 C9 C8 C7 -176.1(4) . . . . ?
C10 C11 C12 C13 -1.8(6) . . . . ?
C14 C13 C12 C11 -2.6(6) . . . . ?
C13 C14 C15 C10 -1.9(6) . . . . ?
C15 C10 C9 C8 -22.2(6) . . . . ?
C15 C10 C11 C12 4.3(6) . . . . ?
C15 C14 C13 N3 -176.4(4) . . . . ?
C15 C14 C13 C12 4.4(5) . . . . ?
C9 C10 C15 C14 177.2(3) . . . . ?
C9 C10 C11 C12 -175.3(4) . . . . ?
C9 C8 C7 O1 -7.7(6) . . . . ?
C9 C8 C7 N2 172.2(4) . . . . ?
C8 S1 C6 N2 -3.0(3) . . . . ?
C8 S1 C6 N1 177.0(3) . . . . ?
C6 S1 C8 C9 -171.7(4) . . . . ?
C6 S1 C8 C7 3.0(3) . . . . ?
C6 N2 C7 O1 -179.3(4) . . . . ?
C6 N2 C7 C8 0.8(5) . . . . ?
C6 N1 C5 C4 -129.3(5) . . . . ?
C6 N1 C1 C2 127.9(5) . . . . ?
C7 N2 C6 S1 1.8(5) . . . . ?
C7 N2 C6 N1 -178.2(4) . . . . ?
C11 C10 C15 C14 -2.5(5) . . . . ?
C11 C10 C9 C8 157.4(4) . . . . ?
C17 N3 C13 C14 -2.4(6) . . . . ?
C17 N3 C13 C12 176.8(4) . . . . ?
C5 N1 C6 S1 -175.9(3) . . . . ?
C5 N1 C6 N2 4.1(7) . . . . ?
C5 N1 C1 C2 -57.6(6) . . . . ?
C5 C4 C3 C2 54.2(6) . . . . ?
C4 C3 C2 C1 -55.2(7) . . . . ?
C16 N3 C13 C14 176.0(4) . . . . ?
C16 N3 C13 C12 -4.8(6) . . . . ?
C1 N1 C6 S1 -1.8(6) . . . . ?
C1 N1 C6 N2 178.1(5) . . . . ?
C1 N1 C5 C4 56.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_crystalb
_database_code_depnum_ccdc_archive 'CCDC 2431132'
loop_
_audit_author_name
_audit_author_address
'Shruti Sangwan'
;University of Hyderabad
India
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
_audit_creation_date             2025-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N3 O S'
_chemical_formula_sum            'C17 H21 N3 O S'
_chemical_formula_weight         315.43
_chemical_absolute_configuration syn
_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 0.0033 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'

_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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                   13.9971(4)
_cell_length_b                   16.3389(5)
_cell_length_c                   7.7318(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.4820(10)
_cell_angle_gamma                90
_cell_volume                     1609.26(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3378
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.975
_cell_measurement_theta_min      0.928
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_preparation       ethanol
_exptl_crystal_recrystallization_method 'during synthesis'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14947
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.027
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.971
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3378
_reflns_number_total             3636
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.141
_refine_ls_abs_structure_details 
;
 Flack x determined using 1520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0921P)²+0.7105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1518
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15), C11(H11), C9(H9)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.61782(8) 0.55151(5) 0.64506(13) 0.0474(3) Uani 1 1 d . . . . .
N3 N 0.1290(3) 0.4223(2) 0.0714(5) 0.0511(8) Uani 1 1 d . . . . .
C13 C 0.2340(3) 0.4138(2) 0.1869(5) 0.0393(8) Uani 1 1 d . . . . .
O1 O 0.7694(3) 0.3552(2) 0.8516(6) 0.0727(11) Uani 1 1 d . . . . .
N2 N 0.7990(3) 0.4927(2) 0.8925(6) 0.0509(9) Uani 1 1 d . . . . .
C8 C 0.6304(4) 0.4457(2) 0.6636(7) 0.0430(9) Uani 1 1 d . . . . .
C12 C 0.2732(3) 0.3422(2) 0.2955(6) 0.0441(8) Uani 1 1 d . . . . .
H12 H 0.2280 0.2989 0.2851 0.053 Uiso 1 1 calc R . . . .
C14 C 0.3068(3) 0.4763(3) 0.2026(6) 0.0446(8) Uani 1 1 d . . . . .
H14 H 0.2844 0.5231 0.1281 0.053 Uiso 1 1 calc R . . . .
C15 C 0.4107(3) 0.4687(3) 0.3272(6) 0.0424(8) Uani 1 1 d . . . . .
H15 H 0.4569 0.5110 0.3357 0.051 Uiso 1 1 calc R . . . .
C11 C 0.3772(3) 0.3360(2) 0.4159(6) 0.0426(8) Uani 1 1 d . . . . .
H11 H 0.4011 0.2876 0.4835 0.051 Uiso 1 1 calc R . . . .
C7 C 0.7392(3) 0.4254(3) 0.8099(6) 0.0481(9) Uani 1 1 d . . . . .
C10 C 0.4490(3) 0.3994(2) 0.4414(5) 0.0395(8) Uani 1 1 d . . . . .
C16 C 0.0548(3) 0.3604(3) 0.0663(7) 0.0569(11) Uani 1 1 d . . . . .
H16A H 0.0732 0.3094 0.0265 0.085 Uiso 1 1 calc GR . . . .
H16B H -0.0143 0.3763 -0.0217 0.085 Uiso 1 1 calc GR . . . .
H16C H 0.0561 0.3542 0.1907 0.085 Uiso 1 1 calc GR . . . .
C17 C 0.0903(4) 0.4948(4) -0.0434(9) 0.0708(15) Uani 1 1 d . . . . .
H17A H 0.1055 0.5420 0.0376 0.106 Uiso 1 1 calc GR . . . .
H17B H 0.0158 0.4903 -0.1153 0.106 Uiso 1 1 calc GR . . . .
H17C H 0.1239 0.5003 -0.1288 0.106 Uiso 1 1 calc GR . . . .
N1 N 0.7833(3) 0.6335(3) 0.8931(8) 0.0716(13) Uani 1 1 d . . . . .
C9 C 0.5573(3) 0.3892(2) 0.5806(6) 0.0440(9) Uani 1 1 d . . . . .
H9 H 0.5781 0.3354 0.6163 0.053 Uiso 1 1 calc R . . . .
C6 C 0.7465(3) 0.5606(3) 0.8283(7) 0.0503(10) Uani 1 1 d . . . . .
C4 C 0.9447(5) 0.7054(5) 0.9728(13) 0.099(2) Uani 1 1 d . . . . .
H4A H 0.9536 0.6824 0.8649 0.119 Uiso 1 1 calc R . . . .
H4B H 1.0139 0.7159 1.0720 0.119 Uiso 1 1 calc R . . . .
C1 C 0.7219(4) 0.7093(3) 0.8442(10) 0.0727(15) Uani 1 1 d . . . . .
H1A H 0.6525 0.6980 0.7462 0.087 Uiso 1 1 calc R . . . .
H1B H 0.7137 0.7295 0.9552 0.087 Uiso 1 1 calc R . . . .
C3 C 0.8846(6) 0.7876(4) 0.9126(11) 0.0823(18) Uani 1 1 d . . . . .
H3A H 0.8861 0.8159 1.0240 0.099 Uiso 1 1 calc R . . . .
H3B H 0.9184 0.8222 0.8525 0.099 Uiso 1 1 calc R . . . .
C5 C 0.8908(4) 0.6458(4) 1.0419(10) 0.0795(17) Uani 1 1 d . . . . .
H5A H 0.8876 0.6657 1.1576 0.095 Uiso 1 1 calc R . . . .
H5B H 0.9287 0.5944 1.0699 0.095 Uiso 1 1 calc R . . . .
C2 C 0.7727(6) 0.7720(4) 0.7765(11) 0.090(2) Uani 1 1 d . . . . .
H2A H 0.7333 0.8226 0.7563 0.108 Uiso 1 1 calc R . . . .
H2B H 0.7711 0.7550 0.6551 0.108 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 C8 1.738(4) . ?
S1 C6 1.777(4) . ?
N3 C13 1.375(5) . ?
N3 C16 1.438(6) . ?
N3 C17 1.445(6) . ?
C13 C12 1.411(6) . ?
C13 C14 1.412(5) . ?
O1 C7 1.219(5) . ?
N2 C7 1.369(6) . ?
N2 C6 1.310(6) . ?
C8 C7 1.511(5) . ?
C8 C9 1.330(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.368(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(6) . ?
C15 H15 0.9300 . ?
C15 C10 1.398(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.400(5) . ?
C10 C9 1.460(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 C6 1.313(6) . ?
N1 C1 1.465(7) . ?
N1 C5 1.481(6) . ?
C9 H9 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.550(11) . ?
C4 C5 1.462(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.463(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.502(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 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
C8 S1 C6 89.0(2) . . ?
C13 N3 C16 120.8(4) . . ?
C13 N3 C17 120.6(4) . . ?
C16 N3 C17 118.5(4) . . ?
N3 C13 C12 121.1(3) . . ?
N3 C13 C14 121.5(4) . . ?
C12 C13 C14 117.4(3) . . ?
C6 N2 C7 111.4(4) . . ?
C7 C8 S1 108.5(3) . . ?
C9 C8 S1 128.3(3) . . ?
C9 C8 C7 123.0(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 118.9 . . ?
C14 C15 C10 122.1(4) . . ?
C10 C15 H15 118.9 . . ?
C12 C11 H11 118.7 . . ?
C12 C11 C10 122.7(4) . . ?
C10 C11 H11 118.7 . . ?
O1 C7 N2 123.7(4) . . ?
O1 C7 C8 122.4(4) . . ?
N2 C7 C8 113.9(4) . . ?
C15 C10 C11 116.5(4) . . ?
C15 C10 C9 124.6(3) . . ?
C11 C10 C9 119.0(3) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 N1 C1 125.0(4) . . ?
C6 N1 C5 122.1(4) . . ?
C1 N1 C5 112.6(4) . . ?
C8 C9 C10 129.2(4) . . ?
C8 C9 H9 115.4 . . ?
C10 C9 H9 115.4 . . ?
N2 C6 S1 117.1(3) . . ?
N2 C6 N1 123.7(4) . . ?
N1 C6 S1 119.2(3) . . ?
H4A C4 H4B 107.8 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C5 C4 C3 112.9(6) . . ?
N1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 N1 111.4(5) . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C2 C3 C4 110.0(5) . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
N1 C5 H5A 110.0 . . ?
N1 C5 H5B 110.0 . . ?
C4 C5 N1 108.6(6) . . ?
C4 C5 H5A 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C1 C2 C3 112.8(5) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?

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
S1 C8 C7 O1 179.9(5) . . . . ?
S1 C8 C7 N2 1.2(5) . . . . ?
S1 C8 C9 C10 4.9(8) . . . . ?
N3 C13 C12 C11 -177.3(4) . . . . ?
N3 C13 C14 C15 176.3(4) . . . . ?
C13 C12 C11 C10 1.4(6) . . . . ?
C13 C14 C15 C10 0.6(6) . . . . ?
C8 S1 C6 N2 3.9(4) . . . . ?
C8 S1 C6 N1 -175.4(5) . . . . ?
C12 C13 C14 C15 -3.4(6) . . . . ?
C12 C11 C10 C15 -4.1(6) . . . . ?
C12 C11 C10 C9 176.6(4) . . . . ?
C14 C13 C12 C11 2.4(6) . . . . ?
C14 C15 C10 C11 3.1(6) . . . . ?
C14 C15 C10 C9 -177.7(4) . . . . ?
C15 C10 C9 C8 20.0(7) . . . . ?
C11 C10 C9 C8 -160.8(5) . . . . ?
C7 N2 C6 S1 -3.8(6) . . . . ?
C7 N2 C6 N1 175.4(5) . . . . ?
C7 C8 C9 C10 178.5(4) . . . . ?
C16 N3 C13 C12 3.7(6) . . . . ?
C16 N3 C13 C14 -175.9(4) . . . . ?
C17 N3 C13 C12 -178.1(5) . . . . ?
C17 N3 C13 C14 2.2(7) . . . . ?
N1 C1 C2 C3 -53.7(9) . . . . ?
C9 C8 C7 O1 5.2(8) . . . . ?
C9 C8 C7 N2 -173.5(5) . . . . ?
C6 S1 C8 C7 -2.5(4) . . . . ?
C6 S1 C8 C9 171.8(5) . . . . ?
C6 N2 C7 O1 -177.1(5) . . . . ?
C6 N2 C7 C8 1.6(6) . . . . ?
C6 N1 C1 C2 -127.3(7) . . . . ?
C6 N1 C5 C4 126.4(7) . . . . ?
C4 C3 C2 C1 49.5(9) . . . . ?
C1 N1 C6 S1 8.4(9) . . . . ?
C1 N1 C6 N2 -170.9(6) . . . . ?
C1 N1 C5 C4 -59.5(8) . . . . ?
C3 C4 C5 N1 55.9(8) . . . . ?
C5 N1 C6 S1 -178.3(5) . . . . ?
C5 N1 C6 N2 2.4(10) . . . . ?
C5 N1 C1 C2 58.8(8) . . . . ?
C5 C4 C3 C2 -51.8(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_an184_0m
_database_code_depnum_ccdc_archive 'CCDC 2431133'
loop_
_audit_author_name
_audit_author_address
'Shruti Sangwan'
;University of Hyderabad
India
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
_audit_creation_date             2025-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N3 O S'
_chemical_formula_sum            'C17 H21 N3 O S'
_chemical_formula_weight         315.43
_chemical_absolute_configuration .
_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 0.0033 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.325(5)
_cell_length_b                   12.993(6)
_cell_length_c                   16.832(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1602.1(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2559
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.975
_cell_measurement_theta_min      0.928
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_preparation       'heat cool heat'
_exptl_crystal_recrystallization_method 'from form 1b'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1384
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            51627
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.129
_diffrn_reflns_theta_min         1.980
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2559
_reflns_number_total             3803
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    %$getVar(solution_reference_short)%
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+0.3153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1654
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B), C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C9(H9), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.4176(2) 0.42448(9) 0.55468(6) 0.0544(4) Uani 1 1 d . . . . .
O1 O 0.4850(6) 0.2638(3) 0.3682(2) 0.0664(11) Uani 1 1 d . . . . .
N2 N 0.4710(5) 0.2361(3) 0.5020(2) 0.0494(10) Uani 1 1 d . . . . .
N1 N 0.4435(7) 0.2516(3) 0.6386(2) 0.0546(11) Uani 1 1 d . . . . .
N3 N 0.4468(6) 0.9160(3) 0.4145(2) 0.0560(11) Uani 1 1 d . . . . .
C10 C 0.4473(6) 0.5927(3) 0.4038(2) 0.0400(10) Uani 1 1 d . . . . .
C13 C 0.4441(6) 0.8109(3) 0.4103(2) 0.0428(10) Uani 1 1 d . . . . .
C7 C 0.4688(6) 0.2964(3) 0.4356(3) 0.0476(11) Uani 1 1 d . . . . .
C6 C 0.4466(6) 0.2901(3) 0.5665(2) 0.0450(10) Uani 1 1 d . . . . .
C8 C 0.4469(6) 0.4089(3) 0.4526(2) 0.0444(10) Uani 1 1 d . . . . .
C12 C 0.4958(6) 0.7583(4) 0.3413(3) 0.0490(12) Uani 1 1 d . . . . .
H12 H 0.5304 0.7954 0.2964 0.059 Uiso 1 1 calc R . . . .
C11 C 0.4960(6) 0.6530(4) 0.3391(2) 0.0456(11) Uani 1 1 d . . . . .
H11 H 0.5303 0.6205 0.2922 0.055 Uiso 1 1 calc R . . . .
C9 C 0.4565(7) 0.4816(3) 0.3975(2) 0.0443(11) Uani 1 1 d . . . . .
H9 H 0.4718 0.4571 0.3460 0.053 Uiso 1 1 calc R . . . .
C14 C 0.3888(8) 0.7509(4) 0.4745(3) 0.0525(12) Uani 1 1 d . . . . .
H14 H 0.3502 0.7831 0.5209 0.063 Uiso 1 1 calc R . . . .
C15 C 0.3898(7) 0.6460(4) 0.4711(3) 0.0533(12) Uani 1 1 d . . . . .
H15 H 0.3508 0.6088 0.5151 0.064 Uiso 1 1 calc R . . . .
C17 C 0.4035(11) 0.9679(4) 0.4874(3) 0.0691(15) Uani 1 1 d . . . . .
H17A H 0.2764 0.9584 0.4994 0.104 Uiso 1 1 calc GR . . . .
H17B H 0.4288 1.0401 0.4819 0.104 Uiso 1 1 calc GR . . . .
H17C H 0.4761 0.9400 0.5297 0.104 Uiso 1 1 calc GR . . . .
C16 C 0.4775(9) 0.9775(4) 0.3450(3) 0.0645(15) Uani 1 1 d . . . . .
H16A H 0.5993 0.9662 0.3259 0.097 Uiso 1 1 calc GR . . . .
H16B H 0.4624 1.0489 0.3581 0.097 Uiso 1 1 calc GR . . . .
H16C H 0.3914 0.9587 0.3046 0.097 Uiso 1 1 calc GR . . . .
C5 C 0.4592(9) 0.1406(4) 0.6512(3) 0.0669(15) Uani 1 1 d . . . . .
H5A H 0.5100 0.1086 0.6041 0.080 Uiso 1 1 calc R . . . .
H5B H 0.3390 0.1116 0.6603 0.080 Uiso 1 1 calc R . . . .
C4 C 0.5786(10) 0.1186(4) 0.7208(3) 0.0713(15) Uani 1 1 d . . . . .
H4A H 0.7025 0.1399 0.7087 0.086 Uiso 1 1 calc R . . . .
H4B H 0.5797 0.0451 0.7308 0.086 Uiso 1 1 calc R . . . .
C3 C 0.5130(8) 0.1745(5) 0.7946(3) 0.0678(16) Uani 1 1 d . . . . .
H3A H 0.3944 0.1482 0.8103 0.081 Uiso 1 1 calc R . . . .
H3B H 0.5977 0.1627 0.8379 0.081 Uiso 1 1 calc R . . . .
C1 C 0.3834(9) 0.3101(4) 0.7081(3) 0.0640(14) Uani 1 1 d . . . . .
H1A H 0.2577 0.2926 0.7203 0.077 Uiso 1 1 calc R . . . .
H1B H 0.3887 0.3831 0.6963 0.077 Uiso 1 1 calc R . . . .
C2 C 0.4998(9) 0.2875(5) 0.7778(3) 0.0688(16) Uani 1 1 d . . . . .
H2A H 0.4500 0.3221 0.8241 0.083 Uiso 1 1 calc R . . . .
H2B H 0.6213 0.3146 0.7685 0.083 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 C6 1.770(4) . ?
S1 C8 1.743(4) . ?
O1 C7 1.217(5) . ?
N2 C7 1.365(6) . ?
N2 C6 1.304(5) . ?
N1 C6 1.314(5) . ?
N1 C5 1.462(6) . ?
N1 C1 1.462(6) . ?
N3 C13 1.368(6) . ?
N3 C17 1.436(6) . ?
N3 C16 1.434(6) . ?
C10 C11 1.388(6) . ?
C10 C9 1.449(6) . ?
C10 C15 1.393(6) . ?
C13 C12 1.400(6) . ?
C13 C14 1.393(6) . ?
C7 C8 1.498(6) . ?
C8 C9 1.326(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.369(6) . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.364(7) . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.489(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.517(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.498(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.480(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 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
C8 S1 C6 88.9(2) . . ?
C6 N2 C7 111.7(4) . . ?
C6 N1 C5 120.5(4) . . ?
C6 N1 C1 123.1(4) . . ?
C5 N1 C1 114.8(4) . . ?
C13 N3 C17 120.7(4) . . ?
C13 N3 C16 121.1(4) . . ?
C16 N3 C17 118.0(4) . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 C15 115.8(4) . . ?
C15 C10 C9 124.6(4) . . ?
N3 C13 C12 121.7(4) . . ?
N3 C13 C14 121.6(4) . . ?
C14 C13 C12 116.7(4) . . ?
O1 C7 N2 124.2(4) . . ?
O1 C7 C8 121.9(4) . . ?
N2 C7 C8 113.9(4) . . ?
N2 C6 S1 117.0(3) . . ?
N2 C6 N1 124.5(4) . . ?
N1 C6 S1 118.5(3) . . ?
C7 C8 S1 108.3(3) . . ?
C9 C8 S1 127.8(3) . . ?
C9 C8 C7 123.8(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.7(4) . . ?
C11 C12 H12 119.7 . . ?
C10 C11 H11 118.6 . . ?
C12 C11 C10 122.9(4) . . ?
C12 C11 H11 118.6 . . ?
C10 C9 H9 114.5 . . ?
C8 C9 C10 131.0(4) . . ?
C8 C9 H9 114.5 . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.7(4) . . ?
C15 C14 H14 119.2 . . ?
C10 C15 H15 118.9 . . ?
C14 C15 C10 122.2(4) . . ?
C14 C15 H15 118.9 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
N1 C5 C4 110.5(4) . . ?
H5A C5 H5B 108.1 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C5 C4 C3 111.5(5) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C2 C3 C4 109.6(4) . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 C2 110.9(5) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 C3 112.4(5) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?

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
S1 C8 C9 C10 0.4(8) . . . . ?
O1 C7 C8 S1 177.3(4) . . . . ?
O1 C7 C8 C9 -5.1(8) . . . . ?
N2 C7 C8 S1 -3.4(5) . . . . ?
N2 C7 C8 C9 174.2(4) . . . . ?
N1 C5 C4 C3 54.5(7) . . . . ?
N1 C1 C2 C3 -53.4(7) . . . . ?
N3 C13 C12 C11 178.5(4) . . . . ?
N3 C13 C14 C15 -178.5(5) . . . . ?
C13 C12 C11 C10 -0.4(8) . . . . ?
C13 C14 C15 C10 0.5(9) . . . . ?
C7 N2 C6 S1 -0.1(5) . . . . ?
C7 N2 C6 N1 -179.6(5) . . . . ?
C7 C8 C9 C10 -176.7(4) . . . . ?
C6 S1 C8 C7 2.6(4) . . . . ?
C6 S1 C8 C9 -174.8(5) . . . . ?
C6 N2 C7 O1 -178.5(5) . . . . ?
C6 N2 C7 C8 2.3(6) . . . . ?
C6 N1 C5 C4 139.4(5) . . . . ?
C6 N1 C1 C2 -140.5(5) . . . . ?
C8 S1 C6 N2 -1.6(4) . . . . ?
C8 S1 C6 N1 177.9(4) . . . . ?
C12 C13 C14 C15 1.8(8) . . . . ?
C11 C10 C9 C8 167.6(5) . . . . ?
C11 C10 C15 C14 -2.7(8) . . . . ?
C9 C10 C11 C12 -178.1(4) . . . . ?
C9 C10 C15 C14 178.1(5) . . . . ?
C14 C13 C12 C11 -1.8(7) . . . . ?
C15 C10 C11 C12 2.7(7) . . . . ?
C15 C10 C9 C8 -13.2(8) . . . . ?
C17 N3 C13 C12 -176.3(5) . . . . ?
C17 N3 C13 C14 4.0(8) . . . . ?
C16 N3 C13 C12 9.1(8) . . . . ?
C16 N3 C13 C14 -170.6(5) . . . . ?
C5 N1 C6 S1 177.4(4) . . . . ?
C5 N1 C6 N2 -3.1(8) . . . . ?
C5 N1 C1 C2 53.3(7) . . . . ?
C5 C4 C3 C2 -55.5(7) . . . . ?
C4 C3 C2 C1 55.0(7) . . . . ?
C1 N1 C6 S1 12.0(7) . . . . ?
C1 N1 C6 N2 -168.5(5) . . . . ?
C1 N1 C5 C4 -54.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
