# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_12393
_database_code_depnum_ccdc_archive 'CCDC 2084138'
loop_
_audit_author_name
_audit_author_address
'Xiao-Sheng Yan'
;Xiamen University
China
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2021-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/8
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N4 O2 S2, C2 H3 N'
_chemical_formula_sum            'C17 H19 N5 O2 S2'
_chemical_formula_weight         389.49
_chemical_absolute_configuration rmad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0334(2)
_cell_length_b                   8.7125(2)
_cell_length_c                   12.1508(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.034(2)
_cell_angle_gamma                90
_cell_volume                     953.94(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3433
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.1320
_cell_measurement_theta_min      4.1760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5890
_diffrn_reflns_point_group_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.707
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.716
_diffrn_reflns_theta_min         3.588
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.550
_reflns_Friedel_fraction_full    0.762
_reflns_Friedel_fraction_max     0.533
_reflns_number_gt                3862
_reflns_number_total             4193
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1298 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.057
_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)+(0.0571P)²+0.1849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 C00K, C00B, C00N, C00A, S002
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
Uanis(S002) \\sim Ueq, Uanis(C00A) \\sim Ueq, Uanis(C00N) \\sim Ueq,
Uanis(C00K) \\sim Ueq, Uanis(C00B) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C00A, C00N, S002, C00K, C00B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5.a Ternary CH refined with riding coordinates:
 C00H(H00H)
5.b Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), N007(H007), N008(H008), C00A(H00A), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P)
5.c Idealised Me refined as rotating group:
 C00O(H00E,H00F,H00G), C00Q(H00B,H00C,H00D)
;
_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
S001 S 0.33730(9) 0.47846(9) 0.76206(6) 0.02255(19) Uani 1 1 d . . . . .
S002 S -0.12657(9) 0.23213(11) 0.65739(7) 0.0294(2) Uani 1 1 d . U . . .
O003 O 0.3139(2) 0.1936(2) 0.33312(18) 0.0192(5) Uani 1 1 d . . . . .
O004 O 0.4384(2) 0.5664(3) 0.40856(19) 0.0217(5) Uani 1 1 d . . . . .
N005 N 0.2800(3) 0.3113(3) 0.5759(2) 0.0176(5) Uani 1 1 d . . . . .
H005 H 0.3150 0.2789 0.5161 0.021 Uiso 1 1 calc R . . . .
N006 N 0.5093(3) 0.4232(3) 0.6042(2) 0.0188(5) Uani 1 1 d . . . . .
H006 H 0.5738 0.4742 0.6448 0.023 Uiso 1 1 calc R . . . .
N007 N 0.5477(3) 0.3687(3) 0.5037(2) 0.0180(5) Uani 1 1 d . . . . .
H007 H 0.5977 0.2850 0.5005 0.022 Uiso 1 1 calc R . . . .
N008 N 0.4333(3) 0.3536(3) 0.2249(2) 0.0190(5) Uani 1 1 d . . . . .
H008 H 0.4318 0.4051 0.1645 0.023 Uiso 1 1 calc R . . . .
N009 N 0.4174(3) 0.6049(4) 0.0547(3) 0.0288(6) Uani 1 1 d . . . . .
C00A C -0.0859(3) 0.1153(4) 0.5470(2) 0.0190(6) Uani 1 1 d . U . . .
H00A H -0.1482 0.0433 0.5112 0.023 Uiso 1 1 calc R . . . .
C00B C 0.1327(3) 0.2656(4) 0.5927(3) 0.0185(6) Uani 1 1 d . U . . .
C00C C 0.3751(3) 0.7270(4) 0.0664(3) 0.0224(6) Uani 1 1 d . . . . .
C00D C 0.3207(3) 0.2602(3) 0.2433(2) 0.0164(6) Uani 1 1 d . . . . .
C00E C 0.5069(3) 0.4466(3) 0.4098(3) 0.0169(6) Uani 1 1 d . . . . .
C00F C 0.3723(3) 0.3988(4) 0.6411(3) 0.0178(6) Uani 1 1 d . . . . .
C00G C 0.2063(3) 0.2352(4) 0.1499(2) 0.0178(6) Uani 1 1 d . . . . .
C00H C 0.5580(3) 0.3693(4) 0.3058(3) 0.0192(6) Uani 1 1 d . . . . .
H00H H 0.5966 0.2670 0.3253 0.023 Uiso 1 1 calc R . . . .
C00I C 0.0010(4) 0.1513(4) -0.0210(3) 0.0233(7) Uani 1 1 d . . . . .
H00I H -0.0666 0.1208 -0.0781 0.028 Uiso 1 1 calc R . . . .
C00J C 0.1359(3) 0.2137(4) -0.0446(3) 0.0210(6) Uani 1 1 d . . . . .
H00J H 0.1583 0.2276 -0.1175 0.025 Uiso 1 1 calc R . . . .
C00K C 0.0410(4) 0.3194(4) 0.6686(3) 0.0221(6) Uani 1 1 d . U . . .
H00K H 0.0676 0.3950 0.7202 0.027 Uiso 1 1 calc R . . . .
C00L C 0.2376(3) 0.2555(4) 0.0409(2) 0.0185(6) Uani 1 1 d . . . . .
H00L H 0.3282 0.2977 0.0248 0.022 Uiso 1 1 calc R . . . .
C00M C 0.0695(3) 0.1759(4) 0.1732(3) 0.0220(7) Uani 1 1 d . . . . .
H00M H 0.0464 0.1640 0.2461 0.026 Uiso 1 1 calc R . . . .
C00N C 0.0652(4) 0.1532(4) 0.5223(3) 0.0248(7) Uani 1 1 d . U . . .
H00N H 0.1129 0.1075 0.4654 0.030 Uiso 1 1 calc R . . . .
C00O C 0.3218(4) 0.8832(4) 0.0811(3) 0.0308(8) Uani 1 1 d . . . . .
H00E H 0.3850 0.9540 0.0460 0.046 Uiso 1 1 calc GR . . . .
H00F H 0.3232 0.9063 0.1585 0.046 Uiso 1 1 calc GR . . . .
H00G H 0.2223 0.8922 0.0486 0.046 Uiso 1 1 calc GR . . . .
C00P C -0.0336(4) 0.1341(4) 0.0876(3) 0.0269(7) Uani 1 1 d . . . . .
H00P H -0.1254 0.0947 0.1034 0.032 Uiso 1 1 calc R . . . .
C00Q C 0.6802(4) 0.4630(5) 0.2586(3) 0.0265(7) Uani 1 1 d . . . . .
H00B H 0.7112 0.4137 0.1934 0.040 Uiso 1 1 calc GR . . . .
H00C H 0.7630 0.4707 0.3123 0.040 Uiso 1 1 calc GR . . . .
H00D H 0.6437 0.5639 0.2402 0.040 Uiso 1 1 calc GR . . . .


_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
S001 C00F 1.675(3) . ?
S002 C00A 1.743(3) . ?
S002 C00K 1.691(3) . ?
O003 C00D 1.241(4) . ?
O004 C00E 1.212(4) . ?
N005 H005 0.8600 . ?
N005 C00B 1.418(4) . ?
N005 C00F 1.346(4) . ?
N006 H006 0.8600 . ?
N006 N007 1.377(4) . ?
N006 C00F 1.363(4) . ?
N007 H007 0.8600 . ?
N007 C00E 1.357(4) . ?
N008 H008 0.8600 . ?
N008 C00D 1.334(4) . ?
N008 C00H 1.448(4) . ?
N009 C00C 1.142(5) . ?
C00A H00A 0.9300 . ?
C00A C00N 1.457(4) . ?
C00B C00K 1.364(4) . ?
C00B C00N 1.410(5) . ?
C00C C00O 1.459(5) . ?
C00D C00G 1.497(4) . ?
C00E C00H 1.531(4) . ?
C00G C00L 1.385(4) . ?
C00G C00M 1.387(4) . ?
C00H H00H 0.9800 . ?
C00H C00Q 1.518(4) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.383(4) . ?
C00I C00P 1.386(5) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.386(4) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00P 1.394(5) . ?
C00N H00N 0.9300 . ?
C00O H00E 0.9600 . ?
C00O H00F 0.9600 . ?
C00O H00G 0.9600 . ?
C00P H00P 0.9300 . ?
C00Q H00B 0.9600 . ?
C00Q H00C 0.9600 . ?
C00Q H00D 0.9600 . ?

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
C00K S002 C00A 95.08(16) . . ?
C00B N005 H005 115.7 . . ?
C00F N005 H005 115.7 . . ?
C00F N005 C00B 128.5(3) . . ?
N007 N006 H006 119.0 . . ?
C00F N006 H006 119.0 . . ?
C00F N006 N007 122.0(3) . . ?
N006 N007 H007 119.9 . . ?
C00E N007 N006 120.2(2) . . ?
C00E N007 H007 119.9 . . ?
C00D N008 H008 119.7 . . ?
C00D N008 C00H 120.6(3) . . ?
C00H N008 H008 119.7 . . ?
S002 C00A H00A 127.0 . . ?
C00N C00A S002 106.1(2) . . ?
C00N C00A H00A 127.0 . . ?
C00K C00B N005 128.4(3) . . ?
C00K C00B C00N 113.0(3) . . ?
C00N C00B N005 118.5(3) . . ?
N009 C00C C00O 179.7(4) . . ?
O003 C00D N008 121.2(3) . . ?
O003 C00D C00G 121.7(3) . . ?
N008 C00D C00G 117.1(3) . . ?
O004 C00E N007 123.3(3) . . ?
O004 C00E C00H 123.5(3) . . ?
N007 C00E C00H 113.2(3) . . ?
N005 C00F S001 127.1(2) . . ?
N005 C00F N006 115.7(3) . . ?
N006 C00F S001 117.1(2) . . ?
C00L C00G C00D 122.0(3) . . ?
C00L C00G C00M 119.2(3) . . ?
C00M C00G C00D 118.5(3) . . ?
N008 C00H C00E 109.6(2) . . ?
N008 C00H H00H 108.9 . . ?
N008 C00H C00Q 110.2(3) . . ?
C00E C00H H00H 108.9 . . ?
C00Q C00H C00E 110.2(3) . . ?
C00Q C00H H00H 108.9 . . ?
C00J C00I H00I 120.0 . . ?
C00J C00I C00P 120.1(3) . . ?
C00P C00I H00I 120.0 . . ?
C00I C00J H00J 120.2 . . ?
C00I C00J C00L 119.7(3) . . ?
C00L C00J H00J 120.2 . . ?
S002 C00K H00K 124.0 . . ?
C00B C00K S002 111.9(3) . . ?
C00B C00K H00K 124.0 . . ?
C00G C00L C00J 120.9(3) . . ?
C00G C00L H00L 119.5 . . ?
C00J C00L H00L 119.5 . . ?
C00G C00M H00M 119.9 . . ?
C00G C00M C00P 120.2(3) . . ?
C00P C00M H00M 119.9 . . ?
C00A C00N H00N 123.1 . . ?
C00B C00N C00A 113.8(3) . . ?
C00B C00N H00N 123.1 . . ?
C00C C00O H00E 109.5 . . ?
C00C C00O H00F 109.5 . . ?
C00C C00O H00G 109.5 . . ?
H00E C00O H00F 109.5 . . ?
H00E C00O H00G 109.5 . . ?
H00F C00O H00G 109.5 . . ?
C00I C00P C00M 119.9(3) . . ?
C00I C00P H00P 120.0 . . ?
C00M C00P H00P 120.0 . . ?
C00H C00Q H00B 109.5 . . ?
C00H C00Q H00C 109.5 . . ?
C00H C00Q H00D 109.5 . . ?
H00B C00Q H00C 109.5 . . ?
H00B C00Q H00D 109.5 . . ?
H00C C00Q H00D 109.5 . . ?

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
S002 C00A C00N C00B 1.2(3) . . . . ?
O003 C00D C00G C00L -153.9(3) . . . . ?
O003 C00D C00G C00M 19.8(5) . . . . ?
O004 C00E C00H N008 -52.0(4) . . . . ?
O004 C00E C00H C00Q 69.5(4) . . . . ?
N005 C00B C00K S002 179.4(3) . . . . ?
N005 C00B C00N C00A -179.9(3) . . . . ?
N006 N007 C00E O004 1.2(4) . . . . ?
N006 N007 C00E C00H -179.7(2) . . . . ?
N007 N006 C00F S001 -177.2(2) . . . . ?
N007 N006 C00F N005 3.4(4) . . . . ?
N007 C00E C00H N008 128.9(3) . . . . ?
N007 C00E C00H C00Q -109.6(3) . . . . ?
N008 C00D C00G C00L 24.1(5) . . . . ?
N008 C00D C00G C00M -162.2(3) . . . . ?
C00A S002 C00K C00B -0.4(3) . . . . ?
C00B N005 C00F S001 0.1(5) . . . . ?
C00B N005 C00F N006 179.5(3) . . . . ?
C00D N008 C00H C00E -66.9(4) . . . . ?
C00D N008 C00H C00Q 171.7(3) . . . . ?
C00D C00G C00L C00J 172.0(3) . . . . ?
C00D C00G C00M C00P -172.4(3) . . . . ?
C00F N005 C00B C00K 12.1(5) . . . . ?
C00F N005 C00B C00N -169.8(3) . . . . ?
C00F N006 N007 C00E 81.3(4) . . . . ?
C00G C00M C00P C00I 0.3(5) . . . . ?
C00H N008 C00D O003 5.7(5) . . . . ?
C00H N008 C00D C00G -172.3(3) . . . . ?
C00I C00J C00L C00G 0.2(5) . . . . ?
C00J C00I C00P C00M -1.8(5) . . . . ?
C00K S002 C00A C00N -0.4(2) . . . . ?
C00K C00B C00N C00A -1.6(4) . . . . ?
C00L C00G C00M C00P 1.5(5) . . . . ?
C00M C00G C00L C00J -1.7(5) . . . . ?
C00N C00B C00K S002 1.2(4) . . . . ?
C00P C00I C00J C00L 1.6(5) . . . . ?

_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_exp_1885
_database_code_depnum_ccdc_archive 'CCDC 2084139'
loop_
_audit_author_name
_audit_author_address
'Xiao-Sheng Yan'
;Xiamen University
China
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2021-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/8
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N4 O2 S2'
_chemical_formula_sum            'C15 H16 N4 O2 S2'
_chemical_formula_weight         348.44
_chemical_absolute_configuration rmad
_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'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.1096(3)
_cell_length_b                   8.1557(2)
_cell_length_c                   10.7216(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.545(4)
_cell_angle_gamma                90
_cell_volume                     827.78(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2449
_cell_measurement_temperature    99.97(11)
_cell_measurement_theta_max      70.4320
_cell_measurement_theta_min      4.3980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4847
_diffrn_reflns_point_group_measured_fraction_full 0.839
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.386
_diffrn_reflns_theta_min         4.404
_diffrn_ambient_temperature      99.97(11)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.574
_reflns_Friedel_fraction_full    0.673
_reflns_Friedel_fraction_max     0.630
_reflns_number_gt                2511
_reflns_number_total             2570
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 884 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.041
_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)+(0.0575P)²+0.0991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0965
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{S002, C002}
{C005, S005}
3. Restrained distances
 C00I-H00I
 0.93 with sigma of 0.02
 C005-H005
 0.93 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C005) = Uanis(S005)
Uanis(S002) = Uanis(C002)
5. Rigid body (RIGU) restrains
 S002, C005, C00E, C00I, C00J, C00B, N007, C00C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: S002(0.8) C005(0.8) H00J(0.8) H00A(0.2) C002(0.2) S005(0.2)
7.a Ternary CH refined with riding coordinates:
 C00C(H00C)
7.b Aromatic/amide H refined with riding coordinates:
 N006(H006), N007(H007), N008(H008), N009(H009), C00F(H00F), C00H(H00H),
 C00J(H00J), C00J(H00A), C00L(H00L), C00M(H00M), C00N(H00N)
7.c Idealised Me refined as rotating group:
 C00K(H00B,H00D,H00E)
;
_atom_sites_solution_hydrogens   mixed
_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
S001 S 0.95166(9) 0.60402(11) 0.82248(8) 0.0279(2) Uani 1 1 d . . . . .
S002 S 0.27600(11) 0.35252(15) 0.07231(10) 0.0331(3) Uani 0.8 1 d . U P A 1
O003 O 0.8761(2) 0.6974(3) 0.3892(2) 0.0260(5) Uani 1 1 d . . . . .
O004 O 0.7407(2) 0.3029(3) 0.3163(2) 0.0226(5) Uani 1 1 d . . . . .
C005 C 0.3175(3) 0.4755(4) -0.0365(2) 0.0363(6) Uani 0.8 1 d D U P A 1
N006 N 1.0243(3) 0.4928(4) 0.4962(3) 0.0198(6) Uani 1 1 d . . . . .
H006 H 1.0715 0.4079 0.4890 0.024 Uiso 1 1 calc R . . . .
N007 N 0.7816(3) 0.4780(4) 0.1723(3) 0.0216(6) Uani 1 1 d . U . . .
H007 H 0.7497 0.5277 0.0969 0.026 Uiso 1 1 calc R . . . .
N008 N 1.0344(3) 0.5497(4) 0.6210(3) 0.0231(6) Uani 1 1 d . . . . .
H008 H 1.1091 0.6023 0.6678 0.028 Uiso 1 1 calc R . . . .
N009 N 0.8173(3) 0.4392(4) 0.5967(3) 0.0223(6) Uani 1 1 d . . . . .
H009 H 0.8237 0.3893 0.5283 0.027 Uiso 1 1 calc R . . . .
C00A C 0.9399(3) 0.5711(4) 0.3857(3) 0.0199(7) Uani 1 1 d . . . . .
C00B C 0.6942(3) 0.3881(4) 0.2154(3) 0.0203(6) Uani 1 1 d . U . . .
C00C C 0.9305(3) 0.4902(4) 0.2545(3) 0.0197(6) Uani 1 1 d . U . . .
H00C H 0.9714 0.3799 0.2723 0.024 Uiso 1 1 calc R . . . .
C00D C 0.6864(3) 0.4238(4) 0.6207(3) 0.0237(7) Uani 1 1 d . . . . .
C00E C 0.5410(3) 0.3976(4) 0.1368(3) 0.0207(6) Uani 1 1 d . U . . .
C00F C 0.5653(4) 0.4812(5) 0.5222(4) 0.0305(8) Uani 1 1 d . . . . .
H00F H 0.5705 0.5306 0.4459 0.037 Uiso 1 1 calc R . . . .
C00G C 0.9299(3) 0.5250(4) 0.6723(3) 0.0221(7) Uani 1 1 d . . . . .
C00H C 0.6803(4) 0.3503(5) 0.7338(4) 0.0296(8) Uani 1 1 d . . . . .
H00H H 0.7621 0.3121 0.7992 0.036 Uiso 1 1 calc R . . . .
C00I C 0.4780(4) 0.4889(5) 0.0180(4) 0.0279(7) Uani 1 1 d D U . . .
C00J C 0.4422(4) 0.3168(5) 0.1765(3) 0.0254(7) Uani 1 1 d . U . . .
H00J H 0.4648 0.2506 0.2518 0.030 Uiso 0.8 1 calc R . P A 1
H00A H 0.4648 0.2506 0.2518 0.030 Uiso 0.2 1 calc R . P A 2
C00K C 1.0102(3) 0.5908(5) 0.1845(3) 0.0264(7) Uani 1 1 d . . . . .
H00B H 0.9991 0.5417 0.1000 0.040 Uiso 1 1 calc GR . . . .
H00D H 1.1087 0.5938 0.2384 0.040 Uiso 1 1 calc GR . . . .
H00E H 0.9733 0.7004 0.1708 0.040 Uiso 1 1 calc GR . . . .
C00L C 0.5491(4) 0.3339(5) 0.7490(4) 0.0347(9) Uani 1 1 d . . . . .
H00L H 0.5438 0.2847 0.8253 0.042 Uiso 1 1 calc R . . . .
C00M C 0.4362(4) 0.4638(6) 0.5394(4) 0.0393(9) Uani 1 1 d . . . . .
H00M H 0.3545 0.5025 0.4743 0.047 Uiso 1 1 calc R . . . .
C00N C 0.4278(4) 0.3896(5) 0.6525(4) 0.0378(9) Uani 1 1 d . . . . .
H00N H 0.3409 0.3776 0.6631 0.045 Uiso 1 1 calc R . . . .
C002 C 0.27600(11) 0.35252(15) 0.07231(10) 0.0331(3) Uani 0.2 1 d . . P A 2
S005 S 0.3175(3) 0.4755(4) -0.0365(2) 0.0363(6) Uani 0.2 1 d . . P A 2
H00I H 0.525(3) 0.548(4) -0.030(3) 0.015(9) Uiso 1 1 d D . . . .
H005 H 0.272(5) 0.525(6) -0.115(3) 0.053(15) Uiso 1 1 d 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
S001 C00G 1.676(3) . ?
S002 C005 1.699(3) . ?
S002 C00J 1.685(4) . ?
O003 C00A 1.222(4) . ?
O004 C00B 1.231(4) . ?
C005 C00I 1.523(4) . ?
C005 H005 0.90(2) . ?
N006 H006 0.8600 . ?
N006 N008 1.386(4) . ?
N006 C00A 1.353(4) . ?
N007 H007 0.8600 . ?
N007 C00B 1.349(4) . ?
N007 C00C 1.456(4) . ?
N008 H008 0.8600 . ?
N008 C00G 1.366(4) . ?
N009 H009 0.8600 . ?
N009 C00D 1.439(4) . ?
N009 C00G 1.340(4) . ?
C00A C00C 1.527(4) . ?
C00B C00E 1.483(4) . ?
C00C H00C 0.9800 . ?
C00C C00K 1.520(5) . ?
C00D C00F 1.388(5) . ?
C00D C00H 1.374(5) . ?
C00E C00I 1.419(5) . ?
C00E C00J 1.383(5) . ?
C00F H00F 0.9300 . ?
C00F C00M 1.387(5) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.398(5) . ?
C00I S005 1.523(4) . ?
C00I H00I 0.94(2) . ?
C00J H00J 0.9300 . ?
C00J H00A 0.9300 . ?
C00J C002 1.685(4) . ?
C00K H00B 0.9600 . ?
C00K H00D 0.9600 . ?
C00K H00E 0.9600 . ?
C00L H00L 0.9300 . ?
C00L C00N 1.375(6) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.384(6) . ?
C00N H00N 0.9300 . ?
C002 S005 1.699(3) . ?
S005 H005 0.90(2) . ?

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
C00J S002 C005 97.37(15) . . ?
S002 C005 H005 138(3) . . ?
C00I C005 S002 105.4(2) . . ?
C00I C005 H005 117(4) . . ?
N008 N006 H006 120.1 . . ?
C00A N006 H006 120.1 . . ?
C00A N006 N008 119.9(3) . . ?
C00B N007 H007 120.3 . . ?
C00B N007 C00C 119.5(3) . . ?
C00C N007 H007 120.3 . . ?
N006 N008 H008 118.9 . . ?
C00G N008 N006 122.3(3) . . ?
C00G N008 H008 118.9 . . ?
C00D N009 H009 117.4 . . ?
C00G N009 H009 117.4 . . ?
C00G N009 C00D 125.2(3) . . ?
O003 C00A N006 123.2(3) . . ?
O003 C00A C00C 122.0(3) . . ?
N006 C00A C00C 114.8(3) . . ?
O004 C00B N007 120.9(3) . . ?
O004 C00B C00E 122.0(3) . . ?
N007 C00B C00E 117.1(3) . . ?
N007 C00C C00A 107.7(3) . . ?
N007 C00C H00C 109.3 . . ?
N007 C00C C00K 110.7(3) . . ?
C00A C00C H00C 109.3 . . ?
C00K C00C C00A 110.4(3) . . ?
C00K C00C H00C 109.3 . . ?
C00F C00D N009 117.1(3) . . ?
C00H C00D N009 121.6(3) . . ?
C00H C00D C00F 121.2(3) . . ?
C00I C00E C00B 126.0(3) . . ?
C00J C00E C00B 121.5(3) . . ?
C00J C00E C00I 112.5(3) . . ?
C00D C00F H00F 120.5 . . ?
C00M C00F C00D 119.0(4) . . ?
C00M C00F H00F 120.5 . . ?
N008 C00G S001 118.1(2) . . ?
N009 C00G S001 125.4(3) . . ?
N009 C00G N008 116.5(3) . . ?
C00D C00H H00H 120.6 . . ?
C00D C00H C00L 118.8(3) . . ?
C00L C00H H00H 120.6 . . ?
C005 C00I H00I 120(2) . . ?
C00E C00I C005 112.8(3) . . ?
C00E C00I S005 112.8(3) . . ?
C00E C00I H00I 127(2) . . ?
S005 C00I H00I 120(2) . . ?
S002 C00J H00J 124.0 . . ?
C00E C00J S002 111.9(3) . . ?
C00E C00J H00J 124.0 . . ?
C00E C00J H00A 124.0 . . ?
C00E C00J C002 111.9(3) . . ?
C002 C00J H00A 124.0 . . ?
C00C C00K H00B 109.5 . . ?
C00C C00K H00D 109.5 . . ?
C00C C00K H00E 109.5 . . ?
H00B C00K H00D 109.5 . . ?
H00B C00K H00E 109.5 . . ?
H00D C00K H00E 109.5 . . ?
C00H C00L H00L 119.6 . . ?
C00N C00L C00H 120.9(4) . . ?
C00N C00L H00L 119.6 . . ?
C00F C00M H00M 119.6 . . ?
C00N C00M C00F 120.7(4) . . ?
C00N C00M H00M 119.6 . . ?
C00L C00N C00M 119.4(3) . . ?
C00L C00N H00N 120.3 . . ?
C00M C00N H00N 120.3 . . ?
C00J C002 S005 97.37(15) . . ?
C00I S005 C002 105.4(2) . . ?
C00I S005 H005 117(4) . . ?
C002 S005 H005 138(3) . . ?

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
S002 C005 C00I C00E 0.5(4) . . . . ?
O003 C00A C00C N007 -49.1(4) . . . . ?
O003 C00A C00C C00K 71.8(4) . . . . ?
O004 C00B C00E C00I -178.4(3) . . . . ?
O004 C00B C00E C00J 2.9(5) . . . . ?
C005 S002 C00J C00E 0.8(3) . . . . ?
N006 N008 C00G S001 -178.3(2) . . . . ?
N006 N008 C00G N009 1.5(5) . . . . ?
N006 C00A C00C N007 131.3(3) . . . . ?
N006 C00A C00C C00K -107.8(3) . . . . ?
N007 C00B C00E C00I 2.0(5) . . . . ?
N007 C00B C00E C00J -176.7(3) . . . . ?
N008 N006 C00A O003 4.1(5) . . . . ?
N008 N006 C00A C00C -176.2(3) . . . . ?
N009 C00D C00F C00M 177.9(3) . . . . ?
N009 C00D C00H C00L -177.7(4) . . . . ?
C00A N006 N008 C00G 75.5(4) . . . . ?
C00B N007 C00C C00A -61.6(4) . . . . ?
C00B N007 C00C C00K 177.6(3) . . . . ?
C00B C00E C00I C005 -178.8(3) . . . . ?
C00B C00E C00I S005 -178.8(3) . . . . ?
C00B C00E C00J S002 178.3(3) . . . . ?
C00B C00E C00J C002 178.3(3) . . . . ?
C00C N007 C00B O004 -7.5(5) . . . . ?
C00C N007 C00B C00E 172.1(3) . . . . ?
C00D N009 C00G S001 11.1(5) . . . . ?
C00D N009 C00G N008 -168.6(3) . . . . ?
C00D C00F C00M C00N -0.4(6) . . . . ?
C00D C00H C00L C00N 0.2(6) . . . . ?
C00E C00I S005 C002 0.5(4) . . . . ?
C00E C00J C002 S005 0.8(3) . . . . ?
C00F C00D C00H C00L -0.1(6) . . . . ?
C00F C00M C00N C00L 0.5(7) . . . . ?
C00G N009 C00D C00F 119.4(4) . . . . ?
C00G N009 C00D C00H -62.9(5) . . . . ?
C00H C00D C00F C00M 0.2(6) . . . . ?
C00H C00L C00N C00M -0.5(6) . . . . ?
C00I C00E C00J S002 -0.6(4) . . . . ?
C00I C00E C00J C002 -0.6(4) . . . . ?
C00J S002 C005 C00I -0.7(3) . . . . ?
C00J C00E C00I C005 0.0(4) . . . . ?
C00J C00E C00I S005 0.0(4) . . . . ?
C00J C002 S005 C00I -0.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
