# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_musa-NM92
_database_code_depnum_ccdc_archive 'CCDC 1841358'
_audit_update_record             
;
2018-05-04 deposited with the CCDC.
2018-11-29 downloaded from the CCDC.
;
_audit_creation_date             2018-03-20
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_chemical_formula_moiety         'C15 H18 N4 O4 S'
_chemical_formula_sum            'C15 H18 N4 O4 S'
_chemical_compound_source        synthesized
_chemical_formula_weight         350.40
_chemical_oxdiff_formula         'C H N O '
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'

_symmetry_Int_Tables_number      2
_chemical_absolute_configuration ?
_cell_length_a                   7.3596(3)
_cell_length_b                   9.2464(6)
_cell_length_c                   14.1726(5)
_cell_angle_alpha                104.253(4)
_cell_angle_beta                 90.749(3)
_cell_angle_gamma                111.461(5)
_cell_volume                     864.24(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_reflns_used    7508
_cell_measurement_theta_max      27.2190
_cell_measurement_theta_min      3.5210
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_description       block
_exptl_crystal_colour            'metallic light yellow'
_diffrn_ambient_temperature      293
_exptl_crystal_density_diffrn    1.3464
_exptl_crystal_F_000             368.4235
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11900
_diffrn_reflns_theta_full        27.3645
_diffrn_reflns_theta_max         27.06
_diffrn_reflns_theta_min         3.19
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00 -15.00   0.50    8.00    --   -9.95 111.00 171.00   66
  2  ω     -7.00  40.00   0.50    8.00    --   10.22-111.00  77.00   94
  3  ω    -56.00 -31.00   0.50    8.00    --   -9.95 125.00  30.00   50
  4  ω      7.00  48.00   0.50    8.00    --   -9.95  57.00   0.00   82
  5  ω    -50.00 -24.00   0.50    8.00    --   -9.95 125.00-180.00   52
  6  ω    -25.00   1.00   0.50    8.00    --   -9.95  57.00   0.00   52
  7  ω    -21.00   4.00   0.50    8.00    --   -9.95 -38.00 150.00   50
  8  ω    -74.00 -45.00   0.50    8.00    --   -9.95 -38.00 150.00   58
  9  ω    -61.00   2.00   0.50    8.00    --   -9.95 -19.00 150.00  126
 10  ω    -70.00   2.00   0.50    8.00    --   -9.95 -38.00  60.00  144
 11  ω    -54.00 -23.00   0.50    8.00    --   10.22 -77.00   0.00   62
 12  ω      5.00  59.00   0.50    8.00    --   10.22-125.00 -30.00  108
 13  ω    -32.00  -2.00   0.50    8.00    --   10.22 123.00-169.37   60
 14  ω    -52.00  11.00   0.50    8.00    --   10.22 -19.00  60.00  126
 15  ω    -33.00  -1.00   0.50    8.00    --   10.22 122.00  20.61   64
 16  ω      3.00  53.00   0.50    8.00    --   10.22-125.00-180.00  100
 17  ω     -2.00  23.00   0.50    8.00    --   10.22 -77.00   0.00   50
 18  ω     -1.00  74.00   0.50    8.00    --   10.22  38.00   0.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0300041000
_diffrn_orient_matrix_UB_12      0.0559970000
_diffrn_orient_matrix_UB_13      -0.0285963000
_diffrn_orient_matrix_UB_21      0.0559152000
_diffrn_orient_matrix_UB_22      0.0613419000
_diffrn_orient_matrix_UB_23      0.0420917000
_diffrn_orient_matrix_UB_31      0.0827003000
_diffrn_orient_matrix_UB_32      -0.0207010000
_diffrn_orient_matrix_UB_33      -0.0105925000
_diffrn_oxdiff_ac3_digest_frames 
;
010ec378803486451121739d89fe0ce42400025f1b3
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01d78d6236c48a65027267f331396291a2fe33
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2796
_reflns_number_total             3695
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2638
_refine_diff_density_min         -0.2584
_refine_diff_density_rms         0.0517
_refine_ls_d_res_high            0.7731
_refine_ls_d_res_low             6.3881
_refine_ls_goodness_of_fit_ref   1.0504
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.0504
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²+0.1314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1447
_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.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), C00G(H00G), C00L(H00L), C00M(H00M), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00H(H00a,H00b,H00c), C00J(H00d,H00f,H00h), C00K(H00i,H00j,H00k), C00O(H00o,
 H00p,H00q)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
S001 S 0.94853(7) 0.93697(6) 0.25184(4) 0.0551(2) Uani 1.000000 .
O002 O 0.1347(2) 0.3917(2) -0.00556(10) 0.0604(4) Uani 1.000000 .
O003 O 0.2620(2) 0.23644(19) 0.03794(11) 0.0652(4) Uani 1.000000 .
N004 N 0.5613(2) 0.78543(18) 0.19153(11) 0.0405(4) Uani 1.000000 .
O005 O 1.0374(2) 0.6873(2) 0.27461(13) 0.0710(5) Uani 1.000000 .
N006 N 0.2603(2) 0.3733(2) 0.04616(11) 0.0467(4) Uani 1.000000 .
N007 N 0.2902(2) 0.7021(2) 0.07670(13) 0.0530(4) Uani 1.000000 .
H007 H 0.1791(2) 0.6268(2) 0.05062(13) 0.0636(5) Uiso 1.000000 R
N008 N 0.8943(2) 0.5794(2) 0.22111(13) 0.0515(4) Uani 1.000000 .
O009 O 0.8929(2) 0.4449(2) 0.18068(13) 0.0752(5) Uani 1.000000 .
C00A C 0.7210(2) 0.6118(2) 0.20705(12) 0.0386(4) Uani 1.000000 .
C00B C 0.3982(2) 0.5040(2) 0.11421(12) 0.0383(4) Uani 1.000000 .
C00C C 0.4107(2) 0.6606(2) 0.12469(12) 0.0389(4) Uani 1.000000 .
C00D C 0.7333(2) 0.7625(2) 0.21509(12) 0.0389(4) Uani 1.000000 .
C00E C 0.5324(2) 0.4671(2) 0.17592(12) 0.0382(4) Uani 1.000000 .
H00E H 0.5630(2) 0.3790(2) 0.13448(12) 0.0459(5) Uiso 1.000000 R
C00F C 0.4437(2) 0.4120(2) 0.26402(12) 0.0400(4) Uani 1.000000 .
C00G C 0.3046(3) 0.4610(3) 0.30885(15) 0.0573(6) Uani 1.000000 .
H00G H 0.2608(3) 0.5288(3) 0.28477(15) 0.0687(7) Uiso 1.000000 R
C00H C 0.5072(3) 0.8986(3) 0.26739(17) 0.0617(6) Uani 1.000000 .
H00a H 0.3703(6) 0.8502(8) 0.2747(8) 0.0925(9) Uiso 1.000000 GR
H00b H 0.5844(17) 0.9231(15) 0.3285(3) 0.0925(9) Uiso 1.000000 GR
H00c H 0.532(2) 0.9962(8) 0.2484(6) 0.0925(9) Uiso 1.000000 GR
C00I C 0.2876(4) 0.3113(3) 0.42690(16) 0.0676(7) Uani 1.000000 .
C00J C 0.9153(3) 1.0602(3) 0.17812(18) 0.0676(6) Uani 1.000000 .
H00d H 0.846(2) 0.9926(3) 0.1154(5) 0.1013(10) Uiso 1.000000 GR
H00f H 0.841(2) 1.1202(15) 0.2104(6) 0.1013(10) Uiso 1.000000 GR
H00h H 1.0413(3) 1.1337(14) 0.1692(10) 0.1013(10) Uiso 1.000000 GR
C00K C 0.3244(4) 0.8591(3) 0.0632(2) 0.0717(7) Uani 1.000000 .
H00i H 0.255(2) 0.8469(3) 0.0020(6) 0.1076(10) Uiso 1.000000 GR
H00j H 0.278(2) 0.9189(8) 0.1159(7) 0.1076(10) Uiso 1.000000 GR
H00k H 0.4626(4) 0.9160(9) 0.0628(13) 0.1076(10) Uiso 1.000000 GR
C00L C 0.2278(4) 0.4114(3) 0.38932(17) 0.0708(7) Uani 1.000000 .
H00L H 0.1336(4) 0.4469(3) 0.41840(17) 0.0850(8) Uiso 1.000000 R
C00M C 0.5043(4) 0.3118(3) 0.30207(18) 0.0702(7) Uani 1.000000 .
H00M H 0.5991(4) 0.2766(3) 0.27354(18) 0.0842(8) Uiso 1.000000 R
C00N C 0.4255(5) 0.2625(3) 0.3825(2) 0.0831(8) Uani 1.000000 .
H00N H 0.4684(5) 0.1943(3) 0.4066(2) 0.0997(10) Uiso 1.000000 R
C00O C 0.1994(5) 0.2532(4) 0.5135(2) 0.1082(12) Uani 1.000000 .
H00o H 0.128(3) 0.317(2) 0.5442(12) 0.1623(18) Uiso 1.000000 GR
H00p H 0.112(3) 0.1421(10) 0.4910(3) 0.1623(18) Uiso 1.000000 GR
H00q H 0.3026(6) 0.263(3) 0.5599(10) 0.1623(18) Uiso 1.000000 GR


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 C00D 1.7544(18) . ?
S001 C00J 1.798(2) . ?
O002 N006 1.257(2) . ?
O003 N006 1.247(2) . ?
N004 C00C 1.399(2) . ?
N004 C00D 1.407(2) . ?
N004 C00H 1.474(3) . ?
O005 N008 1.232(2) . ?
N006 C00B 1.387(2) . ?
N007 H007 0.8600 . ?
N007 C00C 1.326(2) . ?
N007 C00K 1.441(3) . ?
N008 O009 1.230(2) . ?
N008 C00A 1.435(2) . ?
C00A C00D 1.338(3) . ?
C00A C00E 1.499(2) . ?
C00B C00C 1.387(3) . ?
C00B C00E 1.493(2) . ?
C00E H00E 0.9800 . ?
C00E C00F 1.528(2) . ?
C00F C00G 1.368(3) . ?
C00F C00M 1.375(3) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.384(3) . ?
C00H H00a 0.9600 . ?
C00H H00b 0.9600 . ?
C00H H00c 0.9600 . ?
C00I C00L 1.368(4) . ?
C00I C00N 1.357(4) . ?
C00I C00O 1.518(3) . ?
C00J H00d 0.9600 . ?
C00J H00f 0.9600 . ?
C00J H00h 0.9600 . ?
C00K H00i 0.9600 . ?
C00K H00j 0.9600 . ?
C00K H00k 0.9600 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.386(3) . ?
C00N H00N 0.9300 . ?
C00O H00o 0.9600 . ?
C00O H00p 0.9600 . ?
C00O H00q 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
C00J S001 C00D 102.51(9) . . ?
C00D N004 C00C 119.21(15) . . ?
C00H N004 C00C 118.01(14) . . ?
C00H N004 C00D 116.61(15) . . ?
O003 N006 O002 120.48(16) . . ?
C00B N006 O002 120.89(17) . . ?
C00B N006 O003 118.62(16) . . ?
C00C N007 H007 116.29(10) . . ?
C00K N007 H007 116.29(11) . . ?
C00K N007 C00C 127.43(17) . . ?
O009 N008 O005 122.90(17) . . ?
C00A N008 O005 118.23(18) . . ?
C00A N008 O009 118.86(17) . . ?
C00D C00A N008 120.72(16) . . ?
C00E C00A N008 115.94(16) . . ?
C00E C00A C00D 123.18(15) . . ?
C00C C00B N006 121.90(16) . . ?
C00E C00B N006 116.37(16) . . ?
C00E C00B C00C 121.72(15) . . ?
N007 C00C N004 116.96(16) . . ?
C00B C00C N004 117.77(15) . . ?
C00B C00C N007 125.26(16) . . ?
N004 C00D S001 116.23(13) . . ?
C00A C00D S001 125.50(13) . . ?
C00A C00D N004 118.27(15) . . ?
C00B C00E C00A 108.67(14) . . ?
H00E C00E C00A 107.50(9) . . ?
H00E C00E C00B 107.50(9) . . ?
C00F C00E C00A 111.33(13) . . ?
C00F C00E C00B 114.08(14) . . ?
C00F C00E H00E 107.50(9) . . ?
C00G C00F C00E 122.10(17) . . ?
C00M C00F C00E 120.50(17) . . ?
C00M C00F C00G 117.40(18) . . ?
H00G C00G C00F 119.36(12) . . ?
C00L C00G C00F 121.3(2) . . ?
C00L C00G H00G 119.36(15) . . ?
H00a C00H N004 109.5 . . ?
H00b C00H N004 109.5 . . ?
H00b C00H H00a 109.5 . . ?
H00c C00H N004 109.5 . . ?
H00c C00H H00a 109.5 . . ?
H00c C00H H00b 109.5 . . ?
C00N C00I C00L 117.5(2) . . ?
C00O C00I C00L 121.3(3) . . ?
C00O C00I C00N 121.2(3) . . ?
H00d C00J S001 109.5 . . ?
H00f C00J S001 109.5 . . ?
H00f C00J H00d 109.5 . . ?
H00h C00J S001 109.5 . . ?
H00h C00J H00d 109.5 . . ?
H00h C00J H00f 109.5 . . ?
H00i C00K N007 109.5 . . ?
H00j C00K N007 109.5 . . ?
H00j C00K H00i 109.5 . . ?
H00k C00K N007 109.5 . . ?
H00k C00K H00i 109.5 . . ?
H00k C00K H00j 109.5 . . ?
C00I C00L C00G 121.3(2) . . ?
H00L C00L C00G 119.37(15) . . ?
H00L C00L C00I 119.37(14) . . ?
H00M C00M C00F 119.63(13) . . ?
C00N C00M C00F 120.7(2) . . ?
C00N C00M H00M 119.63(16) . . ?
C00M C00N C00I 121.8(2) . . ?
H00N C00N C00I 119.10(14) . . ?
H00N C00N C00M 119.10(16) . . ?
H00o C00O C00I 109.5 . . ?
H00p C00O C00I 109.5 . . ?
H00p C00O H00o 109.5 . . ?
H00q C00O C00I 109.5 . . ?
H00q C00O H00o 109.5 . . ?
H00q C00O H00p 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.833
_oxdiff_exptl_absorpt_empirical_full_min 0.477

