# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_522_001
_database_code_depnum_ccdc_archive 'CCDC 1975044'
loop_
_audit_author_name
_audit_author_address
'A Uppalaiah'
;Birla institute of Technology and sciences
India
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2019-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C17 H17 N O3 S'
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.40
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 0.01920 0.00962 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 0.33537 0.55136 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 0.05239 0.03377 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 0.03256 0.01839 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.6272(2)
_cell_length_b                   16.6924(2)
_cell_length_c                   9.08710(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.219(2)
_cell_angle_gamma                90
_cell_volume                     1522.15(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7031
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.1830
_cell_measurement_theta_min      5.8170
_exptl_absorpt_coefficient_mu    1.996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.3762
_exptl_crystal_F_000             667.3275
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0182
_exptl_crystal_description       block
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8378
_diffrn_reflns_theta_full        79.6459
_diffrn_reflns_theta_max         79.65
_diffrn_reflns_theta_min         4.41
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9711
_diffrn_measured_fraction_theta_max 0.9711
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     54.00  82.00   0.50    5.00    --    0.00  37.00 -90.00   56
  2  ω    -23.00  71.00   0.50    5.00    --    0.00  57.00 150.00  188
  3  ω    -19.00  56.00   0.50    5.00    --    0.00  37.00  30.00  150
  4  ω     47.00 121.00   0.50    8.20    --  107.20 -45.00 -30.00  148
  5  ω     81.00 196.00   0.50    8.20    --  107.20  82.00  90.00  230
  6  ω    106.00 133.00   0.50    8.20    --  107.20  15.00-120.00   54
  7  ω     18.00  63.00   0.50    8.20    --  107.20 -30.00 -60.00   90
  8  ω    146.00 171.00   0.50    8.20    --  107.20  15.00-120.00   50
  9  ω     24.00 126.00   0.50    8.20    --  107.20 -45.00 120.00  204
 10  ω     70.00 119.00   0.50    8.20    --  107.20 -30.00 -60.00   98
 11  ω     72.00 127.00   0.50    8.20    --  107.20 -77.00 -60.00  110
 12  ω     50.00 123.00   0.50    8.20    --  107.20 -15.00-120.00  146
 13  ω     20.00  45.00   0.50    8.20    --  107.20 -15.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0264572000
_diffrn_orient_matrix_UB_12      0.0786724000
_diffrn_orient_matrix_UB_13      0.0734068000
_diffrn_orient_matrix_UB_21      -0.1001917000
_diffrn_orient_matrix_UB_22      0.0254616000
_diffrn_orient_matrix_UB_23      -0.1581133000
_diffrn_orient_matrix_UB_31      -0.1133028000
_diffrn_orient_matrix_UB_32      -0.0409942000
_diffrn_orient_matrix_UB_33      0.0427094000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                3123
_reflns_number_total             3221
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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         0.3256
_refine_diff_density_min         -0.4873
_refine_diff_density_rms         0.0585
_refine_ls_d_res_high            0.7837
_refine_ls_d_res_low             10.0349
_refine_ls_goodness_of_fit_ref   1.0312
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.0312
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.9170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0978
_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:
 C00C(H00a,H00c)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I),
 C00K(H00K)
2.c Idealised Me refined as rotating group:
 C00L(H00f,H00g,H00j), C00M(H00l,H00m,H00n)
;
_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 0.85845(3) 0.693659(19) 0.09160(4) 0.01821(11) Uani 1.000000 .
O002 O 0.88631(10) 0.77853(6) 0.10902(12) 0.0251(2) Uani 1.000000 .
O003 O 0.87013(10) 0.65452(6) -0.04512(11) 0.0246(2) Uani 1.000000 .
O004 O 0.65046(11) 0.48727(7) 0.56509(12) 0.0270(2) Uani 1.000000 .
N005 N 0.97634(12) 0.42609(8) 0.21921(14) 0.0221(3) Uani 1.000000 .
C006 C 0.86937(13) 0.51184(8) 0.32792(15) 0.0184(3) Uani 1.000000 .
C007 C 0.64760(14) 0.72553(9) 0.18991(16) 0.0218(3) Uani 1.000000 .
H007 H 0.70055(14) 0.76583(9) 0.24997(16) 0.0261(3) Uiso 1.000000 R
C008 C 0.69540(14) 0.67725(8) 0.09490(15) 0.0187(3) Uani 1.000000 .
C009 C 0.78775(13) 0.53441(8) 0.41506(16) 0.0198(3) Uani 1.000000 .
H009 H 0.77526(13) 0.58803(8) 0.43436(16) 0.0237(3) Uiso 1.000000 R
C00A C 0.95166(13) 0.55657(8) 0.26022(15) 0.0192(3) Uani 1.000000 .
C00B C 1.01523(14) 0.50156(9) 0.19698(16) 0.0217(3) Uani 1.000000 .
C00C C 0.96806(14) 0.64511(8) 0.26175(16) 0.0204(3) Uani 1.000000 .
H00a H 1.05943(14) 0.65747(8) 0.27052(16) 0.0244(3) Uiso 1.000000 R
H00c H 0.95202(14) 0.66665(8) 0.35313(16) 0.0244(3) Uiso 1.000000 R
C00D C 0.61695(15) 0.61730(8) 0.00367(16) 0.0224(3) Uani 1.000000 .
H00D H 0.65017(15) 0.58491(8) -0.05831(16) 0.0269(4) Uiso 1.000000 R
C00E C 0.82134(14) 0.36994(9) 0.35256(17) 0.0233(3) Uani 1.000000 .
H00E H 0.83129(14) 0.31631(9) 0.33090(17) 0.0280(4) Uiso 1.000000 R
C00F C 0.88749(14) 0.43024(8) 0.30045(16) 0.0200(3) Uani 1.000000 .
C00G C 0.72666(14) 0.47418(9) 0.47109(16) 0.0214(3) Uani 1.000000 .
C00H C 0.51961(15) 0.71248(9) 0.19341(18) 0.0252(3) Uani 1.000000 .
H00H H 0.48740(15) 0.74391(9) 0.25766(18) 0.0303(4) Uiso 1.000000 R
C00I C 0.74078(14) 0.39262(9) 0.43722(17) 0.0238(3) Uani 1.000000 .
H00I H 0.69502(14) 0.35369(9) 0.47259(17) 0.0286(4) Uiso 1.000000 R
C00J C 0.43846(14) 0.65297(9) 0.10213(17) 0.0243(3) Uani 1.000000 .
C00K C 0.48809(15) 0.60642(9) 0.00636(18) 0.0254(3) Uani 1.000000 .
H00K H 0.43410(15) 0.56745(9) -0.05678(18) 0.0305(4) Uiso 1.000000 R
C00L C 0.63149(16) 0.56877(10) 0.59917(18) 0.0287(3) Uani 1.000000 .
H00f H 0.5920(12) 0.5976(2) 0.50363(19) 0.0430(5) Uiso 1.000000 GR
H00g H 0.5737(10) 0.57133(11) 0.6609(13) 0.0430(5) Uiso 1.000000 GR
H00j H 0.7160(2) 0.5923(2) 0.6559(13) 0.0430(5) Uiso 1.000000 GR
C00M C 0.30000(16) 0.63884(12) 0.1080(2) 0.0355(4) Uani 1.000000 .
H00l H 0.30563(17) 0.6198(8) 0.2097(6) 0.0532(6) Uiso 1.000000 GR
H00m H 0.2507(5) 0.6881(2) 0.0868(17) 0.0532(6) Uiso 1.000000 GR
H00n H 0.2556(5) 0.5996(6) 0.0313(12) 0.0532(6) Uiso 1.000000 GR
H005 H 1.008(2) 0.3829(14) 0.200(2) 0.037(5) Uiso 1.000000 .
H00B H 1.0808(18) 0.5094(11) 0.145(2) 0.026(4) Uiso 1.000000 .


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 O002 1.4453(11) . ?
S001 O003 1.4447(10) . ?
S001 C008 1.7642(14) . ?
S001 C00C 1.7941(14) . ?
O004 C00G 1.3742(17) . ?
O004 C00L 1.4242(19) . ?
N005 C00B 1.3616(19) . ?
N005 C00F 1.3785(18) . ?
N005 H005 0.84(2) . ?
C006 C009 1.4048(19) . ?
C006 C00A 1.4335(19) . ?
C006 C00F 1.4094(19) . ?
C007 H007 0.9300 . ?
C007 C008 1.3934(19) . ?
C007 C00H 1.388(2) . ?
C008 C00D 1.3889(19) . ?
C009 H009 0.9300 . ?
C009 C00G 1.3817(19) . ?
C00A C00B 1.373(2) . ?
C00A C00C 1.4876(19) . ?
C00B H00B 0.972(18) . ?
C00C H00a 0.9700 . ?
C00C H00c 0.9700 . ?
C00D H00D 0.9300 . ?
C00D C00K 1.390(2) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.397(2) . ?
C00E C00I 1.379(2) . ?
C00G C00I 1.415(2) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.396(2) . ?
C00I H00I 0.9300 . ?
C00J C00K 1.393(2) . ?
C00J C00M 1.508(2) . ?
C00K H00K 0.9300 . ?
C00L H00f 0.9600 . ?
C00L H00g 0.9600 . ?
C00L H00j 0.9600 . ?
C00M H00l 0.9600 . ?
C00M H00m 0.9600 . ?
C00M H00n 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
O003 S001 O002 117.71(6) . . ?
C008 S001 O002 108.49(6) . . ?
C008 S001 O003 107.90(6) . . ?
C00C S001 O002 107.27(6) . . ?
C00C S001 O003 108.76(6) . . ?
C00C S001 C008 106.14(6) . . ?
C00L O004 C00G 116.20(12) . . ?
C00F N005 C00B 109.13(12) . . ?
H005 N005 C00B 127.2(15) . . ?
H005 N005 C00F 123.1(14) . . ?
C00A C006 C009 132.79(13) . . ?
C00F C006 C009 120.31(13) . . ?
C00F C006 C00A 106.81(12) . . ?
C008 C007 H007 120.55(8) . . ?
C00H C007 H007 120.55(9) . . ?
C00H C007 C008 118.90(13) . . ?
C007 C008 S001 118.77(11) . . ?
C00D C008 S001 120.11(11) . . ?
C00D C008 C007 121.13(13) . . ?
H009 C009 C006 121.15(8) . . ?
C00G C009 C006 117.70(13) . . ?
C00G C009 H009 121.15(8) . . ?
C00B C00A C006 106.56(12) . . ?
C00C C00A C006 126.84(12) . . ?
C00C C00A C00B 126.58(13) . . ?
C00A C00B N005 109.97(12) . . ?
H00B C00B N005 119.9(11) . . ?
H00B C00B C00A 130.1(11) . . ?
C00A C00C S001 113.57(10) . . ?
H00a C00C S001 108.85(5) . . ?
H00a C00C C00A 108.85(7) . . ?
H00c C00C S001 108.85(5) . . ?
H00c C00C C00A 108.85(7) . . ?
H00c C00C H00a 107.7 . . ?
H00D C00D C008 120.49(8) . . ?
C00K C00D C008 119.01(13) . . ?
C00K C00D H00D 120.49(9) . . ?
C00F C00E H00E 121.13(8) . . ?
C00I C00E H00E 121.13(9) . . ?
C00I C00E C00F 117.74(13) . . ?
C006 C00F N005 107.52(12) . . ?
C00E C00F N005 130.94(13) . . ?
C00E C00F C006 121.54(13) . . ?
C009 C00G O004 123.91(13) . . ?
C00I C00G O004 114.50(12) . . ?
C00I C00G C009 121.58(13) . . ?
H00H C00H C007 119.45(9) . . ?
C00J C00H C007 121.10(14) . . ?
C00J C00H H00H 119.45(9) . . ?
C00G C00I C00E 121.03(13) . . ?
H00I C00I C00E 119.49(9) . . ?
H00I C00I C00G 119.49(8) . . ?
C00K C00J C00H 118.77(13) . . ?
C00M C00J C00H 120.62(14) . . ?
C00M C00J C00K 120.61(14) . . ?
C00J C00K C00D 121.07(14) . . ?
H00K C00K C00D 119.47(9) . . ?
H00K C00K C00J 119.47(9) . . ?
H00f C00L O004 109.5 . . ?
H00g C00L O004 109.5 . . ?
H00g C00L H00f 109.5 . . ?
H00j C00L O004 109.5 . . ?
H00j C00L H00f 109.5 . . ?
H00j C00L H00g 109.5 . . ?
H00l C00M C00J 109.5 . . ?
H00m C00M C00J 109.5 . . ?
H00m C00M H00l 109.5 . . ?
H00n C00M C00J 109.5 . . ?
H00n C00M H00l 109.5 . . ?
H00n C00M H00m 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 1.600
_oxdiff_exptl_absorpt_empirical_full_min 0.781
####################################################################### 
# 
# 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_538_23
_database_code_depnum_ccdc_archive 'CCDC 1975054'
loop_
_audit_author_name
_audit_author_address
'A Uppalaiah'
;BITS Pilani Hyderabad Campus 
India
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2019-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         '0.5(C25 H25 N O2 S)'
_chemical_formula_sum            'C12.5 H12.5 N0.5 O S0.5'
_chemical_formula_weight         201.77
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 0.01920 0.00962 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 0.33537 0.55136 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 0.05239 0.03377 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 0.03256 0.01839 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_Int_Tables_number      2
_cell_length_a                   8.4532(2)
_cell_length_b                   10.3709(2)
_cell_length_c                   12.4478(3)
_cell_angle_alpha                96.935(2)
_cell_angle_beta                 104.121(2)
_cell_angle_gamma                102.127(2)
_cell_volume                     1017.51(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7200
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.1210
_cell_measurement_theta_min      5.5970
_exptl_absorpt_coefficient_mu    1.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3171
_exptl_crystal_F_000             429.8533
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0331
_exptl_crystal_description       block
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10533
_diffrn_reflns_theta_full        79.7486
_diffrn_reflns_theta_max         79.75
_diffrn_reflns_theta_min         3.72
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9650
_diffrn_measured_fraction_theta_max 0.9650
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -48.00   0.50    1.00    --    0.00 -19.00-150.00   50
  2  ω     27.00  68.00   0.50    1.00    --    0.00  37.00-180.00   82
  3  ω    -35.00  21.00   0.50    1.00    --    0.00 -19.00-150.00  112
  4  ω    -75.00  17.00   0.50    1.00    --    0.00 -37.00 150.00  184
  5  ω    -11.00  88.00   0.50    1.00    --    0.00  37.00 120.00  198
  6  ω     44.00  94.00   0.50    3.08    --  107.20 -30.00 -90.00  100
  7  ω     81.00 195.00   0.50    3.08    --  107.20  15.00  30.00  228
  8  ω     46.00  77.00   0.50    3.08    --  107.20 -45.00 150.00   62
  9  ω     28.00 140.00   0.50    3.08    --  107.20 -82.00 120.00  224
 10  ω     38.00 135.00   0.50    3.08    --  107.20 -15.00 -30.00  194
 11  ω    102.00 186.00   0.50    3.08    --  107.20  15.00 -60.00  168
 12  ω     39.00 140.00   0.50    3.08    --  107.20 -82.00 -90.00  202
 13  ω     92.00 196.00   0.50    3.08    --  107.20  30.00 -30.00  208
 14  ω     48.00  82.00   0.50    3.08    --  107.20 -61.00  30.00   68
 15  ω     46.00 100.00   0.50    3.08    --  107.20 -82.00 -60.00  108
 16  ω     81.00 117.00   0.50    3.08    --  107.20 -45.00 150.00   72
 17  ω     39.00 127.00   0.50    3.08    --  107.20 -61.00 120.00  176
 18  ω     92.00 136.00   0.50    3.08    --  107.20 -82.00   0.00   88
 19  ω     89.00 114.00   0.50    3.08    --  107.20 -82.00-180.00   50
 20  ω     43.00 110.00   0.50    3.08    --  107.20 -82.00  30.00  134
 21  ω     46.00  71.00   0.50    3.08    --  107.20 -82.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0195809000
_diffrn_orient_matrix_UB_12      0.0035947000
_diffrn_orient_matrix_UB_13      0.1200925000
_diffrn_orient_matrix_UB_21      0.1702189000
_diffrn_orient_matrix_UB_22      0.1048807000
_diffrn_orient_matrix_UB_23      0.0468220000
_diffrn_orient_matrix_UB_31      -0.0910414000
_diffrn_orient_matrix_UB_32      0.1133908000
_diffrn_orient_matrix_UB_33      -0.0150395000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3973
_reflns_number_total             4274
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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         0.3287
_refine_diff_density_min         -0.4861
_refine_diff_density_rms         0.0542
_refine_ls_d_res_high            0.7834
_refine_ls_d_res_low             11.8714
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.0231
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+0.6500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1065
_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:
 C00M(H00a,H00c)
2.b Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00F(H00F), C00L(H00L), C00P(H00q), C00R(H00s), C00J(H00J),
 C00E(H00E), C00Q(H00r), C00G(H00G), C00H(H00H), C00B(H00B)
2.c Idealised Me refined as rotating group:
 C00N(H00d,H00i,H00m), C00O(H00n,H00o,H00p), C00S(H00t,H00u,H00v), C00T(H00w,
 H00x,H00y)
;
_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 0.51274(4) 0.68738(3) 0.78149(3) 0.01830(12) Uani 1.000000 .
O002 O 0.42647(14) 0.62369(11) 0.85519(9) 0.0241(2) Uani 1.000000 .
O003 O 0.44877(14) 0.79276(11) 0.73505(10) 0.0245(2) Uani 1.000000 .
N004 N 0.11964(16) 0.35301(13) 0.46904(11) 0.0196(3) Uani 1.000000 .
C005 C 0.34880(18) 0.50598(14) 0.58246(12) 0.0178(3) Uani 1.000000 .
C006 C 0.27691(18) 0.27290(14) 0.63542(13) 0.0188(3) Uani 1.000000 .
C007 C 0.24897(18) 0.37706(14) 0.56745(12) 0.0182(3) Uani 1.000000 .
C008 C 0.13507(19) 0.46562(15) 0.41976(13) 0.0204(3) Uani 1.000000 .
C009 C 0.73288(19) 0.74662(15) 0.85142(12) 0.0192(3) Uani 1.000000 .
C00A C 0.8297(2) 0.86103(15) 0.82448(13) 0.0212(3) Uani 1.000000 .
C00B C 0.28196(19) 0.14592(15) 0.58482(13) 0.0217(3) Uani 1.000000 .
C00C C 0.27828(19) 0.56332(15) 0.48844(12) 0.0191(3) Uani 1.000000 .
C00D C 0.8104(2) 0.67081(15) 0.92564(13) 0.0218(3) Uani 1.000000 .
C00E C 0.3100(2) 0.30123(15) 0.75241(13) 0.0216(3) Uani 1.000000 .
C00F C 1.0025(2) 0.89814(16) 0.87577(13) 0.0238(3) Uani 1.000000 .
C00G C 0.3559(2) 0.08134(16) 0.76613(14) 0.0243(3) Uani 1.000000 .
C00H C 0.32278(19) 0.05185(15) 0.64979(14) 0.0233(3) Uani 1.000000 .
C00I C 1.0827(2) 0.82675(17) 0.94974(13) 0.0252(3) Uani 1.000000 .
C00J C 0.0375(2) 0.48646(18) 0.31813(13) 0.0260(3) Uani 1.000000 .
C00K C 0.9842(2) 0.71462(16) 0.97349(13) 0.0243(3) Uani 1.000000 .
C00L C 0.3290(2) 0.68460(16) 0.45267(13) 0.0228(3) Uani 1.000000 .
C00M C 0.51513(18) 0.56488(14) 0.66679(12) 0.0185(3) Uani 1.000000 .
C00N C 0.7617(2) 0.94597(17) 0.74266(14) 0.0273(3) Uani 1.000000 .
C00O C -0.02058(19) 0.23410(16) 0.42641(14) 0.0237(3) Uani 1.000000 .
C00P C 0.2354(2) 0.70474(18) 0.35119(14) 0.0281(4) Uani 1.000000 .
C00Q C 0.3487(2) 0.20566(16) 0.81720(14) 0.0249(3) Uani 1.000000 .
C00R C 0.0906(2) 0.60747(19) 0.28547(14) 0.0298(4) Uani 1.000000 .
C00S C 0.7209(2) 0.54423(16) 0.95606(14) 0.0271(3) Uani 1.000000 .
C00T C 1.2707(2) 0.8664(2) 0.99857(16) 0.0342(4) Uani 1.000000 .
H00K H 1.0364(2) 0.66657(16) 1.02356(13) 0.0291(4) Uiso 1.000000 R
H00F H 1.0669(2) 0.97395(16) 0.85979(13) 0.0286(4) Uiso 1.000000 R
H00L H 0.4236(2) 0.75002(16) 0.49624(13) 0.0274(4) Uiso 1.000000 R
H00q H 0.2688(2) 0.78411(18) 0.32588(14) 0.0338(4) Uiso 1.000000 R
H00s H 0.0289(2) 0.62489(19) 0.21841(14) 0.0358(4) Uiso 1.000000 R
H00J H -0.0583(2) 0.42217(18) 0.27468(13) 0.0312(4) Uiso 1.000000 R
H00E H 0.3061(2) 0.38454(15) 0.78736(13) 0.0259(4) Uiso 1.000000 R
H00r H 0.3699(2) 0.22531(16) 0.89504(14) 0.0299(4) Uiso 1.000000 R
H00G H 0.3827(2) 0.01798(16) 0.80962(14) 0.0292(4) Uiso 1.000000 R
H00H H 0.32803(19) -0.03128(15) 0.61538(14) 0.0280(4) Uiso 1.000000 R
H00B H 0.25767(19) 0.12466(15) 0.50684(13) 0.0260(4) Uiso 1.000000 R
H00a H 0.59388(18) 0.60658(14) 0.62850(12) 0.0223(3) Uiso 1.000000 R
H00c H 0.55664(18) 0.49288(14) 0.69756(12) 0.0223(3) Uiso 1.000000 R
H00d H 0.6996(14) 0.8896(2) 0.6714(4) 0.0410(5) Uiso 1.000000 GR
H00i H 0.6887(14) 0.9911(11) 0.7719(5) 0.0410(5) Uiso 1.000000 GR
H00m H 0.8536(2) 1.0111(9) 0.7327(9) 0.0410(5) Uiso 1.000000 GR
H00n H 0.0025(7) 0.1757(6) 0.3694(8) 0.0355(5) Uiso 1.000000 GR
H00o H -0.0348(10) 0.1879(7) 0.4871(2) 0.0355(5) Uiso 1.000000 GR
H00p H -0.1218(4) 0.26044(19) 0.3947(10) 0.0355(5) Uiso 1.000000 GR
H00t H 0.6373(12) 0.5634(3) 0.9913(10) 0.0407(5) Uiso 1.000000 GR
H00u H 0.6676(14) 0.4777(5) 0.8890(2) 0.0407(5) Uiso 1.000000 GR
H00v H 0.8010(3) 0.5111(8) 1.0071(9) 0.0407(5) Uiso 1.000000 GR
H00w H 1.3228(2) 0.8324(13) 0.9446(5) 0.0514(6) Uiso 1.000000 GR
H00x H 1.3090(3) 0.9624(2) 1.0166(12) 0.0514(6) Uiso 1.000000 GR
H00y H 1.3004(3) 0.8296(13) 1.0657(7) 0.0514(6) 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 O002 1.4422(11) . ?
S001 O003 1.4385(11) . ?
S001 C009 1.7884(15) . ?
S001 C00M 1.7999(15) . ?
N004 C007 1.3842(19) . ?
N004 C008 1.3803(19) . ?
N004 C00O 1.4589(19) . ?
C005 C007 1.387(2) . ?
C005 C00C 1.434(2) . ?
C005 C00M 1.489(2) . ?
C006 C007 1.473(2) . ?
C006 C00B 1.403(2) . ?
C006 C00E 1.396(2) . ?
C008 C00C 1.412(2) . ?
C008 C00J 1.400(2) . ?
C009 C00A 1.419(2) . ?
C009 C00D 1.413(2) . ?
C00A C00F 1.393(2) . ?
C00A C00N 1.513(2) . ?
C00B C00H 1.386(2) . ?
C00B H00B 0.9300 . ?
C00C C00L 1.402(2) . ?
C00D C00K 1.395(2) . ?
C00D C00S 1.510(2) . ?
C00E C00Q 1.393(2) . ?
C00E H00E 0.9300 . ?
C00F C00I 1.388(2) . ?
C00F H00F 0.9300 . ?
C00G C00H 1.389(2) . ?
C00G C00Q 1.387(2) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I C00K 1.389(2) . ?
C00I C00T 1.502(2) . ?
C00J C00R 1.385(2) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00P 1.382(2) . ?
C00L H00L 0.9300 . ?
C00M H00a 0.9700 . ?
C00M H00c 0.9700 . ?
C00N H00d 0.9600 . ?
C00N H00i 0.9600 . ?
C00N H00m 0.9600 . ?
C00O H00n 0.9600 . ?
C00O H00o 0.9600 . ?
C00O H00p 0.9600 . ?
C00P C00R 1.407(3) . ?
C00P H00q 0.9300 . ?
C00Q H00r 0.9300 . ?
C00R H00s 0.9300 . ?
C00S H00t 0.9600 . ?
C00S H00u 0.9600 . ?
C00S H00v 0.9600 . ?
C00T H00w 0.9600 . ?
C00T H00x 0.9600 . ?
C00T H00y 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
O003 S001 O002 116.15(7) . . ?
C009 S001 O002 109.76(7) . . ?
C009 S001 O003 110.24(7) . . ?
C00M S001 O002 110.50(7) . . ?
C00M S001 O003 108.20(7) . . ?
C00M S001 C009 100.89(7) . . ?
C008 N004 C007 109.01(12) . . ?
C00O N004 C007 126.95(13) . . ?
C00O N004 C008 123.85(13) . . ?
C00C C005 C007 106.93(13) . . ?
C00M C005 C007 126.66(13) . . ?
C00M C005 C00C 125.45(13) . . ?
C00B C006 C007 120.68(13) . . ?
C00E C006 C007 120.65(13) . . ?
C00E C006 C00B 118.54(14) . . ?
C005 C007 N004 109.10(13) . . ?
C006 C007 N004 122.62(13) . . ?
C006 C007 C005 128.05(13) . . ?
C00C C008 N004 107.94(13) . . ?
C00J C008 N004 129.49(15) . . ?
C00J C008 C00C 122.52(14) . . ?
C00A C009 S001 120.02(11) . . ?
C00D C009 S001 118.84(11) . . ?
C00D C009 C00A 120.89(14) . . ?
C00F C00A C009 117.89(14) . . ?
C00N C00A C009 125.50(14) . . ?
C00N C00A C00F 116.60(14) . . ?
C00H C00B C006 120.71(14) . . ?
H00B C00B C006 119.65(9) . . ?
H00B C00B C00H 119.65(9) . . ?
C008 C00C C005 107.02(13) . . ?
C00L C00C C005 133.53(15) . . ?
C00L C00C C008 119.29(14) . . ?
C00K C00D C009 117.67(14) . . ?
C00S C00D C009 125.32(14) . . ?
C00S C00D C00K 117.01(14) . . ?
C00Q C00E C006 120.50(14) . . ?
H00E C00E C006 119.75(9) . . ?
H00E C00E C00Q 119.75(9) . . ?
C00I C00F C00A 122.77(15) . . ?
H00F C00F C00A 118.62(9) . . ?
H00F C00F C00I 118.62(9) . . ?
C00Q C00G C00H 119.73(14) . . ?
H00G C00G C00H 120.13(9) . . ?
H00G C00G C00Q 120.13(9) . . ?
C00G C00H C00B 120.20(14) . . ?
H00H C00H C00B 119.90(9) . . ?
H00H C00H C00G 119.90(9) . . ?
C00K C00I C00F 117.78(15) . . ?
C00T C00I C00F 120.95(16) . . ?
C00T C00I C00K 121.22(16) . . ?
C00R C00J C008 116.73(16) . . ?
H00J C00J C008 121.64(10) . . ?
H00J C00J C00R 121.64(10) . . ?
C00I C00K C00D 122.97(15) . . ?
H00K C00K C00D 118.51(9) . . ?
H00K C00K C00I 118.51(9) . . ?
C00P C00L C00C 118.51(16) . . ?
H00L C00L C00C 120.75(9) . . ?
H00L C00L C00P 120.75(10) . . ?
C005 C00M S001 114.77(10) . . ?
H00a C00M S001 108.57(5) . . ?
H00a C00M C005 108.57(8) . . ?
H00c C00M S001 108.57(5) . . ?
H00c C00M C005 108.57(8) . . ?
H00c C00M H00a 107.6 . . ?
H00d C00N C00A 109.5 . . ?
H00i C00N C00A 109.5 . . ?
H00i C00N H00d 109.5 . . ?
H00m C00N C00A 109.5 . . ?
H00m C00N H00d 109.5 . . ?
H00m C00N H00i 109.5 . . ?
H00n C00O N004 109.5 . . ?
H00o C00O N004 109.5 . . ?
H00o C00O H00n 109.5 . . ?
H00p C00O N004 109.5 . . ?
H00p C00O H00n 109.5 . . ?
H00p C00O H00o 109.5 . . ?
C00R C00P C00L 121.26(15) . . ?
H00q C00P C00L 119.37(10) . . ?
H00q C00P C00R 119.37(9) . . ?
C00G C00Q C00E 120.30(15) . . ?
H00r C00Q C00E 119.85(9) . . ?
H00r C00Q C00G 119.85(9) . . ?
C00P C00R C00J 121.65(15) . . ?
H00s C00R C00J 119.17(10) . . ?
H00s C00R C00P 119.17(9) . . ?
H00t C00S C00D 109.5 . . ?
H00u C00S C00D 109.5 . . ?
H00u C00S H00t 109.5 . . ?
H00v C00S C00D 109.5 . . ?
H00v C00S H00t 109.5 . . ?
H00v C00S H00u 109.5 . . ?
H00w C00T C00I 109.5 . . ?
H00x C00T C00I 109.5 . . ?
H00x C00T H00w 109.5 . . ?
H00y C00T C00I 109.5 . . ?
H00y C00T H00w 109.5 . . ?
H00y C00T H00x 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 1.799
_oxdiff_exptl_absorpt_empirical_full_min 0.699
