# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_cmpd_1_288K
_database_code_depnum_ccdc_archive 'CCDC 2298630'
loop_
_audit_author_name
_audit_author_address
'Hiroki Takahashi'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C14 H26 N2 O5 S'
_chemical_formula_sum            'C14 H26 N2 O5 S'
_chemical_formula_weight         334.439
_chemical_absolute_configuration unk
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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           ' P 65'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x-y,x,z+5/6
3 y,-x+y,z+1/6
4 -y,x-y,z+2/3
5 -x+y,-x,z+1/3
6 -x,-y,z+1/2

_symmetry_Int_Tables_number      170
_cell_length_a                   11.2868(11)
_cell_length_b                   11.2868(11)
_cell_length_c                   27.130(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2993.1(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    288(2)
_cell_measurement_reflns_used    6073
_cell_measurement_theta_max      29.9460
_cell_measurement_theta_min      2.3240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_coefficient_mu    0.183
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_description       needle
_exptl_crystal_F_000             1081.303
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0965
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9656
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            28458
_diffrn_reflns_point_group_measured_fraction_full 0.9975
_diffrn_reflns_point_group_measured_fraction_max 0.9389
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.12
_diffrn_reflns_theta_min         2.57
_diffrn_ambient_temperature      288
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9656
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    8.00    --  -20.00  44.00 330.00  360
  2  ω   -110.00  70.00   0.50    8.00    --  -20.00  44.00 240.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.911
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              39
_reflns_limit_l_min              -38
_reflns_number_gt                2305
_reflns_number_total             6050
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.5437
_refine_diff_density_min         -0.6635
_refine_diff_density_rms         0.1120
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.14(14)
_refine_ls_d_res_high            0.6876
_refine_ls_d_res_low             7.9303
_refine_ls_goodness_of_fit_ref   1.0392
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     205
_refine_ls_number_reflns         6050
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2396
_refine_ls_R_factor_gt           0.0859
_refine_ls_restrained_S_all      1.0392
_refine_ls_shift/su_max          0.0711
_refine_ls_shift/su_mean         0.0019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0875P)²+0.0279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.2175
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2a)
2.d Idealised Me refined as rotating group:
 C3(H3a,H3b,H3c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C12(H12a,H12b,H12c),
 C13(H13a,H13b,H13c), C14(H14a,H14c,H14b)
;
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
C1 C 0.4546(6) 0.2938(6) 0.1330(2) 0.0950(16) Uani 1.000000 .
C2 C 0.3204(6) 0.2656(5) 0.15774(18) 0.1015(18) Uani 1.000000 .
H2 H 0.2902(6) 0.3254(5) 0.14309(18) 0.122(2) Uiso 1.000000 R
C3 C 0.3417(8) 0.2938(8) 0.2124(2) 0.185(4) Uani 1.000000 .
H3a H 0.388(8) 0.249(7) 0.2259(6) 0.278(7) Uiso 1.000000 GR
H3b H 0.396(8) 0.3906(10) 0.2177(3) 0.278(7) Uiso 1.000000 GR
H3c H 0.2546(10) 0.260(8) 0.2283(5) 0.278(7) Uiso 1.000000 GR
C4 C 0.1632(4) 0.0781(4) 0.10573(14) 0.0653(11) Uani 1.000000 .
C5 C 0.0716(4) -0.0752(4) 0.10118(12) 0.0570(10) Uani 1.000000 .
H5 H 0.0464(4) -0.1146(4) 0.13432(12) 0.0684(12) Uiso 1.000000 R
C6 C 0.1543(5) -0.1307(5) 0.07622(15) 0.0759(12) Uani 1.000000 .
H6a H 0.1811(5) -0.0898(5) 0.04375(15) 0.0911(15) Uiso 1.000000 R
H6b H 0.2372(5) -0.1023(5) 0.09507(15) 0.0911(15) Uiso 1.000000 R
C7 C 0.0810(6) -0.2833(6) 0.0708(2) 0.0979(16) Uani 1.000000 .
H7a H 0.0040(6) -0.3104(6) 0.0487(2) 0.1175(19) Uiso 1.000000 R
H7b H 0.1426(6) -0.3086(6) 0.0553(2) 0.1175(19) Uiso 1.000000 R
C8 C 0.1682(7) -0.3224(9) 0.1614(3) 0.154(3) Uani 1.000000 .
H8a H 0.1455(8) -0.357(5) 0.1944(7) 0.231(4) Uiso 1.000000 GR
H8b H 0.224(3) -0.354(5) 0.1463(14) 0.231(4) Uiso 1.000000 GR
H8c H 0.218(3) -0.2242(9) 0.162(2) 0.231(4) Uiso 1.000000 GR
C9 C 0.6631(8) 0.4650(9) 0.1008(4) 0.200(5) Uani 1.000000 .
H9a H 0.726(3) 0.468(10) 0.1253(8) 0.301(7) Uiso 1.000000 GR
H9b H 0.651(2) 0.399(6) 0.076(3) 0.301(7) Uiso 1.000000 GR
H9c H 0.699(5) 0.554(4) 0.086(3) 0.301(7) Uiso 1.000000 GR
C10 C -0.1606(5) -0.1173(5) 0.09548(16) 0.0734(13) Uani 1.000000 .
C11 C -0.3867(7) -0.1493(10) 0.0767(2) 0.129(3) Uani 1.000000 .
C12 C -0.4629(8) -0.1768(11) 0.0292(3) 0.179(4) Uani 1.000000 .
H12a H -0.478(8) -0.262(4) 0.0157(16) 0.269(6) Uiso 1.000000 GR
H12b H -0.549(4) -0.182(9) 0.0350(6) 0.269(6) Uiso 1.000000 GR
H12c H -0.410(4) -0.104(4) 0.0063(11) 0.269(6) Uiso 1.000000 GR
C13 C -0.4616(10) -0.2591(17) 0.1145(5) 0.262(7) Uani 1.000000 .
H13a H -0.489(15) -0.223(4) 0.141(3) 0.393(10) Uiso 1.000000 GR
H13b H -0.541(10) -0.334(7) 0.0997(15) 0.393(10) Uiso 1.000000 GR
H13c H -0.403(6) -0.291(13) 0.127(5) 0.393(10) Uiso 1.000000 GR
C14 C -0.3477(15) -0.0069(17) 0.0935(5) 0.301(9) Uani 1.000000 .
H14a H -0.298(17) 0.057(3) 0.068(3) 0.451(14) Uiso 1.000000 GR
H14c H -0.429(2) -0.003(5) 0.101(7) 0.451(14) Uiso 1.000000 GR
H14b H -0.291(17) 0.016(8) 0.122(4) 0.451(14) Uiso 1.000000 GR
O1 O 0.5302(5) 0.4253(5) 0.12421(18) 0.1441(17) Uani 1.000000 .
O2 O 0.4846(5) 0.2100(6) 0.1240(2) 0.1408(16) Uani 1.000000 .
O3 O 0.1951(4) 0.1542(3) 0.07016(11) 0.0979(11) Uani 1.000000 .
O4 O -0.1695(5) -0.1032(6) 0.13890(10) 0.143(2) Uani 1.000000 .
O5 O -0.2606(3) -0.1452(4) 0.06335(11) 0.0925(10) Uani 1.000000 .
N1 N 0.2164(4) 0.1256(4) 0.15017(12) 0.0750(10) Uani 1.000000 .
H1 H 0.1876(4) 0.0708(4) 0.17497(12) 0.0899(12) Uiso 1.000000 R
N2 N -0.0514(3) -0.1099(3) 0.07422(11) 0.0650(9) Uani 1.000000 .
H2a H -0.0542(3) -0.1266(3) 0.04317(11) 0.0780(11) Uiso 1.000000 R
S1 S 0.01850(16) -0.37917(13) 0.12733(6) 0.0996(5) Uani 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
C1 C2 1.538(8) . ?
C1 O1 1.312(7) . ?
C1 O2 1.179(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.510(7) . ?
C2 N1 1.436(6) . ?
C3 H3a 0.9600 . ?
C3 H3b 0.9600 . ?
C3 H3c 0.9600 . ?
C4 C5 1.513(6) . ?
C4 O3 1.220(5) . ?
C4 N1 1.334(5) . ?
C5 H5 0.9800 . ?
C5 C6 1.518(6) . ?
C5 N2 1.440(5) . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C6 C7 1.500(7) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 S1 1.805(5) . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C8 S1 1.743(7) . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
C9 O1 1.477(9) . ?
C10 O4 1.199(5) . ?
C10 O5 1.333(5) . ?
C10 N2 1.325(5) . ?
C11 C12 1.493(8) . ?
C11 C13 1.501(11) . ?
C11 C14 1.509(14) . ?
C11 O5 1.447(7) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C14 H14a 0.9600 . ?
C14 H14c 0.9600 . ?
C14 H14b 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2a 0.8600 . ?

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
O1 C1 C2 109.2(6) . . ?
O2 C1 C2 124.9(5) . . ?
O2 C1 O1 125.8(7) . . ?
H2 C2 C1 109.0(3) . . ?
C3 C2 C1 110.4(5) . . ?
C3 C2 H2 109.0(5) . . ?
N1 C2 C1 110.1(5) . . ?
N1 C2 H2 109.0(3) . . ?
N1 C2 C3 109.2(4) . . ?
H3a C3 C2 109.5 . . ?
H3b C3 C2 109.5 . . ?
H3b C3 H3a 109.5 . . ?
H3c C3 C2 109.5 . . ?
H3c C3 H3a 109.5 . . ?
H3c C3 H3b 109.5 . . ?
O3 C4 C5 122.2(3) . . ?
N1 C4 C5 116.5(3) . . ?
N1 C4 O3 121.1(4) . . ?
H5 C5 C4 108.73(18) . . ?
C6 C5 C4 107.4(3) . . ?
C6 C5 H5 108.7(2) . . ?
N2 C5 C4 111.6(3) . . ?
N2 C5 H5 108.73(18) . . ?
N2 C5 C6 111.6(3) . . ?
H6a C6 C5 108.6(2) . . ?
H6b C6 C5 108.6(2) . . ?
H6b C6 H6a 107.6 . . ?
C7 C6 C5 114.7(4) . . ?
C7 C6 H6a 108.6(3) . . ?
C7 C6 H6b 108.6(3) . . ?
H7a C7 C6 108.4(3) . . ?
H7b C7 C6 108.4(3) . . ?
H7b C7 H7a 107.5 . . ?
S1 C7 C6 115.5(4) . . ?
S1 C7 H7a 108.4(2) . . ?
S1 C7 H7b 108.40(18) . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
S1 C8 H8a 109.5 . . ?
S1 C8 H8b 109.5 . . ?
S1 C8 H8c 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
O1 C9 H9a 109.5 . . ?
O1 C9 H9b 109.5 . . ?
O1 C9 H9c 109.5 . . ?
O5 C10 O4 123.8(4) . . ?
N2 C10 O4 123.8(4) . . ?
N2 C10 O5 112.4(4) . . ?
C13 C11 C12 112.9(9) . . ?
C14 C11 C12 108.3(8) . . ?
C14 C11 C13 114.6(10) . . ?
O5 C11 C12 104.2(5) . . ?
O5 C11 C13 109.6(6) . . ?
O5 C11 C14 106.5(8) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14a C14 C11 109.5 . . ?
H14c C14 C11 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14b C14 C11 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14b C14 H14c 109.5 . . ?
C9 O1 C1 114.1(7) . . ?
C11 O5 C10 123.1(4) . . ?
C4 N1 C2 121.8(4) . . ?
H1 N1 C2 119.1(2) . . ?
H1 N1 C4 119.1(2) . . ?
C10 N2 C5 122.4(3) . . ?
H2a N2 C5 118.79(18) . . ?
H2a N2 C10 118.8(2) . . ?
C8 S1 C7 102.4(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
C1 C2 N1 C4 -68.4(5) . . . . ?
C2 N1 C4 C5 170.5(5) . . . . ?
C2 N1 C4 O3 -4.5(6) . . . . ?
C4 C5 C6 C7 177.2(4) . . . . ?
C4 C5 N2 C10 -84.2(4) . . . . ?
C5 C6 C7 S1 -56.8(4) . . . . ?
C5 N2 C10 O4 -4.2(5) . . . . ?
C5 N2 C10 O5 177.3(4) . . . . ?
C10 O5 C11 C12 177.2(8) . . . . ?
C10 O5 C11 C13 -61.7(9) . . . . ?
C10 O5 C11 C14 62.8(7) . . . . ?


_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
;

_exptl_crystal_colour            Colorless
_chemical_melting_point          398.2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
####################################################################### 
# 
# 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_cmpd_1_CO2_188K
_database_code_depnum_ccdc_archive 'CCDC 2298633'
loop_
_audit_author_name
_audit_author_address
'Hiroki Takahashi'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2024-02-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C14 H26 N2 O5 S, 0.254(C O2)'
_chemical_formula_sum            'C14.25 H26 N2 O5.51 S'
_chemical_formula_weight         345.61
_chemical_absolute_configuration unk
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 0.12444 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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           ' P 65'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x-y,x,z+5/6
3 y,-x+y,z+1/6
4 -y,x-y,z+2/3
5 -x+y,-x,z+1/3
6 -x,-y,z+1/2

_symmetry_Int_Tables_number      170
_cell_length_a                   11.239(4)
_cell_length_b                   11.239(4)
_cell_length_c                   27.0392(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2957.9(15)
_cell_formula_units_Z            6
_cell_measurement_temperature    188(2)
_cell_measurement_reflns_used    5390
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5
_exptl_absorpt_coefficient_mu    0.189
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       needle
_exptl_crystal_F_000             1118.444
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.9967
_diffrn_reflns_Laue_measured_fraction_max 0.9970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9839
_diffrn_reflns_point_group_measured_fraction_full 0.9150
_diffrn_reflns_point_group_measured_fraction_max 0.9031
_diffrn_reflns_theta_full        25.2425
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.63
_diffrn_ambient_temperature      188.15
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.805
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              34
_reflns_limit_l_min              -26
_reflns_number_gt                2329
_reflns_number_total             4090
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.3331
_refine_diff_density_min         -0.1966
_refine_diff_density_rms         0.0494
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.05(11)
_refine_ls_d_res_high            0.7702
_refine_ls_d_res_low             5.6195
_refine_ls_goodness_of_fit_ref   0.8487
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    66
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4090
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      0.8476
_refine_ls_shift/su_max          0.0722
_refine_ls_shift/su_mean         0.0019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1201P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1886
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6-C15
 1.2 with sigma of 0.02
 O7-C15
 1.2 with sigma of 0.02
 O7-O6
 2.4 with sigma of 0.02
3. Restrained angles
 O6-C15-O7
 fixed at 180 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C2B) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
5. Others
 Sof(C1B)=Sof(C9B)=Sof(O1B)=Sof(O2B)=Sof(C3B)=Sof(C2B)=Sof(O6)=Sof(O7)=Sof(C15)=
 Sof(H9Ba)=Sof(H9Bb)=Sof(H9Bc)=Sof(H3Ba)=Sof(H3Bb)=Sof(H3Bc)=Sof(H16)=
 Sof(H1nb)=1-FVAR(1)
 Sof(C2A)=Sof(C3A)=Sof(C1A)=Sof(O2A)=Sof(O1A)=Sof(C9A)=Sof(H2A)=Sof(H3Aa)=Sof(H3Ab)=
 Sof(H3Ac)=Sof(H9Aa)=Sof(H9Ab)=Sof(H9Ac)=Sof(H1na)=FVAR(1)
 Sof(C10B)=Sof(O4B)=Sof(O5B)=Sof(C13B)=Sof(C14B)=Sof(C11B)=Sof(C12B)=Sof(H13Ba)=
 Sof(H13Bb)=Sof(H13Bc)=Sof(H12Ba)=Sof(H12Bb)=Sof(H12Bc)=Sof(H2nb)=Sof(H14Ba)=Sof(H14Bb)=
 Sof(H14Bc)=1-FVAR(2)
 Sof(C10A)=Sof(C11A)=Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(O4A)=Sof(O5A)=Sof(H12Aa)=
 Sof(H12Ab)=Sof(H12Ac)=Sof(H13Aa)=Sof(H13Ab)=Sof(H13Ac)=Sof(H14Aa)=Sof(H14Ab)=
 Sof(H14Ac)=Sof(H2na)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C2A(H2A), C5(H5), C2B(H16)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C7(H7a,H7b)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1na), N1(H1nb), N2(H2na), N2(H2nb)
6.d Idealised Me refined as rotating group:
 C3A(H3Aa,H3Ab,H3Ac), C8(H8a,H8b,H8c), C9B(H9Ba,H9Bb,H9Bc), C12A(H12Aa,H12Ab,H12Ac),
 C13A(H13Aa,H13Ab,H13Ac), C14A(H14Aa,H14Ab,H14Ac), C3B(H3Ba,H3Bb,H3Bc), C9A(H9Aa,H9Ab,
 H9Ac), C13B(H13Ba,H13Bb,H13Bc), C12B(H12Ba,H12Bb,H12Bc), C14B(H14Ba,H14Bb,H14Bc)
;
_atom_sites_solution_primary     iterative
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
_atom_site_refinement_flags_adp
_atom_site_disorder_group
C1B C 0.426(4) 0.328(4) 0.1552(16) 0.087(13) Uani 0.254(10) . . 2
C2A C 0.3269(9) 0.2650(8) 0.1814(3) 0.074(2) Uani 0.746(10) . . 1
C3A C 0.3596(13) 0.2858(13) 0.2386(4) 0.124(4) Uani 0.746(10) . . 1
C4 C 0.1654(4) 0.0853(4) 0.12887(18) 0.0675(11) Uani 1.000000 . . .
C5 C 0.0724(4) -0.0693(4) 0.12337(16) 0.0572(9) Uani 1.000000 . . .
C6 C 0.1556(4) -0.1254(5) 0.09736(18) 0.0706(11) Uani 1.000000 . . .
C7 C 0.0811(6) -0.2800(5) 0.0913(2) 0.0823(13) Uani 1.000000 . . .
C8 C 0.1661(7) -0.3238(7) 0.1829(3) 0.116(2) Uani 1.000000 . . .
C9B C 0.622(5) 0.515(6) 0.120(2) 0.16(2) Uani 0.254(10) . . 2
C10A C -0.177(3) -0.122(3) 0.1154(14) 0.056(7) Uani 0.47(3) . . 1
C11A C -0.4042(18) -0.170(2) 0.1033(7) 0.072(4) Uani 0.47(3) . . 1
C12A C -0.444(2) -0.147(4) 0.0509(12) 0.108(8) Uani 0.47(3) . . 1
C13A C -0.4825(18) -0.296(2) 0.1329(10) 0.124(8) Uani 0.47(3) . . 1
C14A C -0.391(2) -0.042(3) 0.1305(12) 0.147(11) Uani 0.47(3) . . 1
O1B O 0.503(3) 0.4744(18) 0.1420(11) 0.119(9) Uani 0.254(10) . . 2
O2B O 0.487(3) 0.266(6) 0.1504(15) 0.16(3) Uani 0.254(10) . . 2
O3 O 0.1975(4) 0.1627(3) 0.09222(16) 0.0956(12) Uani 1.000000 . . .
O4A O -0.1892(15) -0.124(2) 0.1627(4) 0.070(3) Uani 0.47(3) . . 1
O5A O -0.261(3) -0.120(3) 0.0818(8) 0.080(6) Uani 0.47(3) . . 1
N1 N 0.2154(4) 0.1294(4) 0.17295(16) 0.0837(12) Uani 1.000000 . . .
N2 N -0.0510(3) -0.1040(3) 0.09586(15) 0.0601(8) Uani 1.000000 . . .
S1 S 0.01455(14) -0.37672(12) 0.14774(10) 0.0813(4) Uani 1.000000 . . .
C3B C 0.307(3) 0.342(3) 0.2268(9) 0.099(9) Uani 0.254(10) . . 2
C1A C 0.4558(16) 0.2890(19) 0.1545(7) 0.076(5) Uani 0.746(10) . . 1
O2A O 0.4872(10) 0.2090(9) 0.1416(4) 0.100(2) Uani 0.746(10) . . 1
O1A O 0.5325(9) 0.4238(8) 0.1456(3) 0.105(2) Uani 0.746(10) . . 1
C9A C 0.6641(13) 0.4696(14) 0.1200(8) 0.142(6) Uani 0.746(10) . . 1
C10B C -0.142(3) -0.091(3) 0.1189(14) 0.068(7) Uani 0.53(3) . . 2
O4B O -0.136(2) -0.052(2) 0.1595(4) 0.087(4) Uani 0.53(3) . . 2
O5B O -0.2619(16) -0.1527(19) 0.0879(6) 0.055(3) Uani 0.53(3) . . 2
C13B C -0.434(2) -0.185(4) 0.1456(8) 0.145(12) Uani 0.53(3) . . 2
C14B C -0.308(3) 0.046(3) 0.1057(7) 0.141(9) Uani 0.53(3) . . 2
C2B C 0.298(2) 0.3087(19) 0.1773(9) 0.059(5) Uani 0.254(10) . U 2
O6 O 0.425(2) 0.016(2) 0.2058(7) 0.122(8) Uani 0.254(10) D . 2
O7 O 0.512(3) 0.221(3) 0.2548(11) 0.172(12) Uani 0.254(10) D . 2
C15 C 0.470(2) 0.119(2) 0.2300(9) 0.142(13) Uani 0.254(10) D . 2
C11B C -0.363(2) -0.095(4) 0.0976(7) 0.107(8) Uani 0.53(3) . . 2
C12B C -0.490(2) -0.198(3) 0.0559(10) 0.119(8) Uani 0.53(3) . . 2
H2A H 0.3009(9) 0.3333(8) 0.1697(3) 0.089(2) Uiso 0.746(10) R . 1
H3Aa H 0.283(4) 0.286(9) 0.2560(5) 0.187(7) Uiso 0.746(10) GR . 1
H3Ab H 0.372(9) 0.211(5) 0.2511(8) 0.187(7) Uiso 0.746(10) GR . 1
H3Ac H 0.444(5) 0.374(4) 0.2440(4) 0.187(7) Uiso 0.746(10) GR . 1
H5 H 0.0459(4) -0.1113(4) 0.15704(16) 0.0686(11) Uiso 1.000000 R . .
H6a H 0.1827(4) -0.0826(5) 0.06423(18) 0.0848(13) Uiso 1.000000 R . .
H6b H 0.2408(4) -0.0968(5) 0.11644(18) 0.0848(13) Uiso 1.000000 R . .
H7a H 0.0038(6) -0.3070(5) 0.0680(2) 0.0987(15) Uiso 1.000000 R . .
H7b H 0.1451(6) -0.3059(5) 0.0761(2) 0.0987(15) Uiso 1.000000 R . .
H8a H 0.225(3) -0.352(5) 0.1659(10) 0.174(3) Uiso 1.000000 GR . .
H8b H 0.215(3) -0.2236(9) 0.1864(17) 0.174(3) Uiso 1.000000 GR . .
H8c H 0.1416(8) -0.367(4) 0.2156(7) 0.174(3) Uiso 1.000000 GR . .
H9Ba H 0.618(14) 0.54(4) 0.086(5) 0.24(4) Uiso 0.254(10) GR . 2
H9Bb H 0.695(8) 0.59(2) 0.138(8) 0.24(4) Uiso 0.254(10) GR . 2
H9Bc H 0.642(18) 0.439(13) 0.120(12) 0.24(4) Uiso 0.254(10) GR . 2
H12Aa H -0.467(12) -0.228(6) 0.0302(18) 0.163(12) Uiso 0.47(3) GR . 1
H12Ab H -0.525(8) -0.135(14) 0.0531(13) 0.163(12) Uiso 0.47(3) GR . 1
H12Ac H -0.367(5) -0.065(8) 0.036(2) 0.163(12) Uiso 0.47(3) GR . 1
H13Aa H -0.577(5) -0.314(9) 0.137(5) 0.186(12) Uiso 0.47(3) GR . 1
H13Ab H -0.484(12) -0.373(3) 0.116(3) 0.186(12) Uiso 0.47(3) GR . 1
H13Ac H -0.439(9) -0.283(6) 0.165(2) 0.186(12) Uiso 0.47(3) GR . 1
H14Aa H -0.320(14) 0.042(3) 0.114(4) 0.221(16) Uiso 0.47(3) GR . 1
H14Ab H -0.479(6) -0.045(10) 0.130(6) 0.221(16) Uiso 0.47(3) GR . 1
H14Ac H -0.364(19) -0.043(10) 0.165(2) 0.221(16) Uiso 0.47(3) GR . 1
H3Ba H 0.34(2) 0.290(16) 0.2453(14) 0.149(13) Uiso 0.254(10) GR . 2
H3Bb H 0.371(16) 0.441(5) 0.2310(13) 0.149(13) Uiso 0.254(10) GR . 2
H3Bc H 0.216(5) 0.319(19) 0.239(2) 0.149(13) Uiso 0.254(10) GR . 2
H9Aa H 0.6473(17) 0.451(10) 0.0845(9) 0.214(9) Uiso 0.746(10) GR . 1
H9Ab H 0.725(4) 0.568(3) 0.125(3) 0.214(9) Uiso 0.746(10) GR . 1
H9Ac H 0.708(5) 0.419(8) 0.133(3) 0.214(9) Uiso 0.746(10) GR . 1
H13Ba H -0.462(15) -0.282(5) 0.139(2) 0.218(18) Uiso 0.53(3) GR . 2
H13Bb H -0.368(6) -0.152(11) 0.1730(17) 0.218(18) Uiso 0.53(3) GR . 2
H13Bc H -0.514(10) -0.178(13) 0.155(3) 0.218(18) Uiso 0.53(3) GR . 2
H16 H 0.253(2) 0.3494(19) 0.1571(9) 0.071(6) Uiso 0.254(10) R . 2
H12Ba H -0.466(6) -0.155(7) 0.0230(14) 0.179(11) Uiso 0.53(3) GR . 2
H12Bb H -0.499(8) -0.289(5) 0.055(3) 0.179(11) Uiso 0.53(3) GR . 2
H12Bc H -0.578(3) -0.207(10) 0.066(3) 0.179(11) Uiso 0.53(3) GR . 2
H1na H 0.1792(4) 0.0735(4) 0.19831(16) 0.1004(14) Uiso 0.746(10) R . 1
H1nb H 0.2084(4) 0.0752(4) 0.19764(16) 0.1004(14) Uiso 0.254(10) R . 2
H2na H -0.0482(3) -0.1155(3) 0.06377(15) 0.0722(9) Uiso 0.47(3) R . 1
H2nb H -0.0622(3) -0.1321(3) 0.06496(15) 0.0722(9) Uiso 0.53(3) R . 2
H14Ba H -0.248(12) 0.074(5) 0.135(3) 0.212(14) Uiso 0.53(3) GR . 2
H14Bb H -0.255(12) 0.097(3) 0.077(2) 0.212(14) Uiso 0.53(3) GR . 2
H14Bc H -0.383(3) 0.066(4) 0.111(5) 0.212(14) Uiso 0.53(3) GR . 2


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
C1B O1B 1.47(4) . ?
C1B O2B 1.21(7) . ?
C1B C2B 1.47(5) . ?
C2A C3A 1.578(12) . ?
C2A N1 1.427(8) . ?
C2A C1A 1.520(19) . ?
C2A H2A 1.0000 . ?
C3A H3Aa 0.9800 . ?
C3A H3Ab 0.9800 . ?
C3A H3Ac 0.9800 . ?
C4 C5 1.523(5) . ?
C4 O3 1.247(5) . ?
C4 N1 1.305(5) . ?
C5 C6 1.534(6) . ?
C5 N2 1.445(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.514(7) . ?
C6 H6a 0.9900 . ?
C6 H6b 0.9900 . ?
C7 S1 1.805(5) . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C8 S1 1.773(7) . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C8 H8c 0.9800 . ?
C9B O1B 1.32(5) . ?
C9B H9Ba 0.9800 . ?
C9B H9Bb 0.9800 . ?
C9B H9Bc 0.9800 . ?
C10A O4A 1.29(4) . ?
C10A O5A 1.32(4) . ?
C10A N2 1.43(4) . ?
C11A C12A 1.55(4) . ?
C11A C13A 1.47(3) . ?
C11A C14A 1.55(3) . ?
C11A O5A 1.53(3) . ?
C12A H12Aa 0.9800 . ?
C12A H12Ab 0.9800 . ?
C12A H12Ac 0.9800 . ?
C13A H13Aa 0.9800 . ?
C13A H13Ab 0.9800 . ?
C13A H13Ac 0.9800 . ?
C14A H14Aa 0.9800 . ?
C14A H14Ab 0.9800 . ?
C14A H14Ac 0.9800 . ?
N1 C2B 1.751(19) . ?
N1 H1na 0.8800 . ?
N1 H1nb 0.8800 . ?
N2 C10B 1.26(4) . ?
N2 H2na 0.8800 . ?
N2 H2nb 0.8800 . ?
C3B C2B 1.38(3) . ?
C3B H3Ba 0.9800 . ?
C3B H3Bb 0.9800 . ?
C3B H3Bc 0.9800 . ?
C1A O2A 1.17(2) . ?
C1A O1A 1.338(19) . ?
O1A C9A 1.474(17) . ?
C9A H9Aa 0.9800 . ?
C9A H9Ab 0.9800 . ?
C9A H9Ac 0.9800 . ?
C10B O4B 1.17(4) . ?
C10B O5B 1.44(3) . ?
O5B C11B 1.59(3) . ?
C13B C11B 1.59(2) . ?
C13B H13Ba 0.9800 . ?
C13B H13Bb 0.9800 . ?
C13B H13Bc 0.9800 . ?
C14B C11B 1.41(3) . ?
C14B H14Ba 0.9800 . ?
C14B H14Bb 0.9800 . ?
C14B H14Bc 0.9800 . ?
C2B H16 1.0000 . ?
O6 C15 1.204(16) . ?
O7 C15 1.200(16) . ?
C11B C12B 1.73(4) . ?
C12B H12Ba 0.9800 . ?
C12B H12Bb 0.9800 . ?
C12B H12Bc 0.9800 . ?

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
O2B C1B O1B 116(4) . . ?
C2B C1B O1B 105(3) . . ?
C2B C1B O2B 139(4) . . ?
N1 C2A C3A 109.3(6) . . ?
C1A C2A C3A 108.2(10) . . ?
C1A C2A N1 111.2(9) . . ?
H2A C2A C3A 109.4(7) . . ?
H2A C2A N1 109.4(5) . . ?
H2A C2A C1A 109.4(7) . . ?
H3Aa C3A C2A 109.5 . . ?
H3Ab C3A C2A 109.5 . . ?
H3Ab C3A H3Aa 109.5 . . ?
H3Ac C3A C2A 109.5 . . ?
H3Ac C3A H3Aa 109.5 . . ?
H3Ac C3A H3Ab 109.5 . . ?
O3 C4 C5 120.8(3) . . ?
N1 C4 C5 116.2(3) . . ?
N1 C4 O3 122.8(4) . . ?
C6 C5 C4 107.6(3) . . ?
N2 C5 C4 112.1(3) . . ?
N2 C5 C6 110.7(3) . . ?
H5 C5 C4 108.80(19) . . ?
H5 C5 C6 108.8(2) . . ?
H5 C5 N2 108.8(2) . . ?
C7 C6 C5 114.9(3) . . ?
H6a C6 C5 108.6(2) . . ?
H6a C6 C7 108.6(2) . . ?
H6b C6 C5 108.6(2) . . ?
H6b C6 C7 108.6(3) . . ?
H6b C6 H6a 107.5 . . ?
S1 C7 C6 115.1(3) . . ?
H7a C7 C6 108.5(3) . . ?
H7a C7 S1 108.50(19) . . ?
H7b C7 C6 108.5(2) . . ?
H7b C7 S1 108.50(17) . . ?
H7b C7 H7a 107.5 . . ?
H8a C8 S1 109.5 . . ?
H8b C8 S1 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 S1 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
H9Ba C9B O1B 109.5 . . ?
H9Bb C9B O1B 109.5 . . ?
H9Bb C9B H9Ba 109.5 . . ?
H9Bc C9B O1B 109.5 . . ?
H9Bc C9B H9Ba 109.5 . . ?
H9Bc C9B H9Bb 109.5 . . ?
O5A C10A O4A 128(3) . . ?
N2 C10A O4A 117(2) . . ?
N2 C10A O5A 114(3) . . ?
C13A C11A C12A 124.9(18) . . ?
C14A C11A C12A 101(2) . . ?
C14A C11A C13A 111.4(18) . . ?
O5A C11A C12A 86.0(18) . . ?
O5A C11A C13A 125.1(17) . . ?
O5A C11A C14A 104.0(18) . . ?
H12Aa C12A C11A 109.5 . . ?
H12Ab C12A C11A 109.5 . . ?
H12Ab C12A H12Aa 109.5 . . ?
H12Ac C12A C11A 109.5 . . ?
H12Ac C12A H12Aa 109.5 . . ?
H12Ac C12A H12Ab 109.5 . . ?
H13Aa C13A C11A 109.5 . . ?
H13Ab C13A C11A 109.5 . . ?
H13Ab C13A H13Aa 109.5 . . ?
H13Ac C13A C11A 109.5 . . ?
H13Ac C13A H13Aa 109.5 . . ?
H13Ac C13A H13Ab 109.5 . . ?
H14Aa C14A C11A 109.5 . . ?
H14Ab C14A C11A 109.5 . . ?
H14Ab C14A H14Aa 109.5 . . ?
H14Ac C14A C11A 109.5 . . ?
H14Ac C14A H14Aa 109.5 . . ?
H14Ac C14A H14Ab 109.5 . . ?
C9B O1B C1B 115(4) . . ?
C11A O5A C10A 111(2) . . ?
C4 N1 C2A 122.3(5) . . ?
C2B N1 C2A 23.4(7) . . ?
C2B N1 C4 112.2(8) . . ?
H1na N1 C2A 118.9(3) . . ?
H1na N1 C4 118.9(2) . . ?
H1na N1 C2B 124.0(8) . . ?
H1nb N1 C2A 110.1(4) . . ?
H1nb N1 C4 123.9(3) . . ?
H1nb N1 C2B 123.9(8) . . ?
H1nb N1 H1na 21.0 . . ?
C10A N2 C5 126.8(14) . . ?
C10B N2 C5 115.8(14) . . ?
C10B N2 C10A 15(2) . . ?
H2na N2 C5 116.6(2) . . ?
H2na N2 C10A 116.6(14) . . ?
H2na N2 C10B 126.3(15) . . ?
H2nb N2 C5 122.1(2) . . ?
H2nb N2 C10A 110.3(13) . . ?
H2nb N2 C10B 122.1(14) . . ?
H2nb N2 H2na 11.5 . . ?
C8 S1 C7 102.2(3) . . ?
H3Ba C3B C2B 109.5 . . ?
H3Bb C3B C2B 109.5 . . ?
H3Bb C3B H3Ba 109.5 . . ?
H3Bc C3B C2B 109.5 . . ?
H3Bc C3B H3Ba 109.5 . . ?
H3Bc C3B H3Bb 109.5 . . ?
O2A C1A C2A 129.2(15) . . ?
O1A C1A C2A 107.7(13) . . ?
O1A C1A O2A 123.1(15) . . ?
C9A O1A C1A 116.5(11) . . ?
H9Aa C9A O1A 109.5 . . ?
H9Ab C9A O1A 109.5 . . ?
H9Ab C9A H9Aa 109.5 . . ?
H9Ac C9A O1A 109.5 . . ?
H9Ac C9A H9Aa 109.5 . . ?
H9Ac C9A H9Ab 109.5 . . ?
O4B C10B N2 128(3) . . ?
O5B C10B N2 106(3) . . ?
O5B C10B O4B 126(3) . . ?
C11B O5B C10B 114(2) . . ?
H13Ba C13B C11B 109.5 . . ?
H13Bb C13B C11B 109.5 . . ?
H13Bb C13B H13Ba 109.5 . . ?
H13Bc C13B C11B 109.5 . . ?
H13Bc C13B H13Ba 109.5 . . ?
H13Bc C13B H13Bb 109.5 . . ?
H14Ba C14B C11B 109.5 . . ?
H14Bb C14B C11B 109.5 . . ?
H14Bb C14B H14Ba 109.5 . . ?
H14Bc C14B C11B 109.5 . . ?
H14Bc C14B H14Ba 109.5 . . ?
H14Bc C14B H14Bb 109.5 . . ?
N1 C2B C1B 93.6(18) . . ?
C3B C2B C1B 115(2) . . ?
C3B C2B N1 107.6(19) . . ?
H16 C2B C1B 113.1(19) . . ?
H16 C2B N1 113.1(7) . . ?
H16 C2B C3B 113.1(17) . . ?
O7 C15 O6 178.6(11) . . ?
C13B C11B O5B 96.1(14) . . ?
C14B C11B O5B 119.0(18) . . ?
C14B C11B C13B 113(2) . . ?
C12B C11B O5B 98(2) . . ?
C12B C11B C13B 97.4(19) . . ?
C12B C11B C14B 127.1(17) . . ?
H12Ba C12B C11B 109.5 . . ?
H12Bb C12B C11B 109.5 . . ?
H12Bb C12B H12Ba 109.5 . . ?
H12Bc C12B C11B 109.5 . . ?
H12Bc C12B H12Ba 109.5 . . ?
H12Bc C12B H12Bb 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
C2A N1 C4 C5 165.4(6) . . . . ?
C2A N1 C4 O3 -10.1(8) . . . . ?
C2A C1A O1A C9A 179.4(11) . . . . ?
C4 C5 C6 C7 176.8(3) . . . . ?
C4 C5 N2 C10A -87.2(16) . . . . ?
C4 C5 N2 C10B -75.5(17) . . . . ?
C5 C6 C7 S1 -54.9(4) . . . . ?
C5 N2 C10A O4A -9.3(10) . . . . ?
C5 N2 C10A O5A 165(2) . . . . ?
C5 N2 C10B O4B 2.1(15) . . . . ?
C5 N2 C10B O5B -170(2) . . . . ?
C10A O5A C11A C12A -179(3) . . . . ?
C10A O5A C11A C13A -48(3) . . . . ?
C10A O5A C11A C14A 81(3) . . . . ?
C10A N2 C10B O4B 143(11) . . . . ?
C10A N2 C10B O5B -30(13) . . . . ?
N2 C10B O5B C11B -156(2) . . . . ?
C10B O5B C11B C13B -80(3) . . . . ?
C10B O5B C11B C14B 41(3) . . . . ?
C10B O5B C11B C12B -178(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_angle_atom_site_label_1
_restr_angle_atom_site_label_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_1
_restr_angle_site_symmetry_2
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
_restr_angle_diff
O6 C15 O7 1 1 1 180.0000 1.1459 1.3627

loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O6 C15 1 1.2000 0.0200 -0.0037
O7 O6 1 2.4000 0.0200 -0.0039
O7 C15 1 1.2000 0.0200 -0.0004

loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C2B 0.0200

####################################################################### 
# 
# 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_cmpd_1_238K
_database_code_depnum_ccdc_archive 'CCDC 2298631'
loop_
_audit_author_name
_audit_author_address
'Hiroki Takahashi'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C14 H26 N2 O5 S'
_chemical_formula_sum            'C14 H26 N2 O5 S'
_chemical_formula_weight         334.439
_chemical_absolute_configuration unk
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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           ' P 65'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x-y,x,z+5/6
3 y,-x+y,z+1/6
4 -y,x-y,z+2/3
5 -x+y,-x,z+1/3
6 -x,-y,z+1/2

_symmetry_Int_Tables_number      170
_cell_length_a                   11.2333(9)
_cell_length_b                   11.2333(9)
_cell_length_c                   27.046(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2955.6(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    6686
_cell_measurement_temperature    238
_cell_measurement_theta_max      30.4080
_cell_measurement_theta_min      2.2000
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       needle
_exptl_crystal_F_000             1081.303
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9592
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            28134
_diffrn_reflns_point_group_measured_fraction_full 0.9975
_diffrn_reflns_point_group_measured_fraction_max 0.9324
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.20
_diffrn_reflns_theta_min         2.58
_diffrn_ambient_temperature      238
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9592
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    8.00    --  -20.00  44.00 330.00  360
  2  ω   -110.00  70.00   0.50    8.00    --  -20.00  44.00 240.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0705785000
_diffrn_orient_matrix_UB_12      0.0225903000
_diffrn_orient_matrix_UB_13      0.0039531000
_diffrn_orient_matrix_UB_21      0.0170225000
_diffrn_orient_matrix_UB_22      0.0678632000
_diffrn_orient_matrix_UB_23      -0.0064796000
_diffrn_orient_matrix_UB_31      -0.0066845000
_diffrn_orient_matrix_UB_32      0.0140204000
_diffrn_orient_matrix_UB_33      0.0251089000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.905
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              39
_reflns_limit_l_min              -38
_reflns_number_gt                2642
_reflns_number_total             5962
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.0931
_refine_diff_density_min         -0.4943
_refine_diff_density_rms         0.1047
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.10(13)
_refine_ls_d_res_high            0.6861
_refine_ls_d_res_low             7.8972
_refine_ls_goodness_of_fit_ref   0.9909
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     205
_refine_ls_number_reflns         5962
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2013
_refine_ls_R_factor_gt           0.0815
_refine_ls_restrained_S_all      0.9909
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1245P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.2460
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2a)
2.d Idealised Me refined as rotating group:
 C3(H3a,H3b,H3c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C12(H12a,H12b,H12c),
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c)
;
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
C1 C 0.4549(6) 0.2931(6) 0.09549(19) 0.0835(16) Uani 1.000000 .
C2 C 0.3208(6) 0.2663(5) 0.12181(19) 0.0889(18) Uani 1.000000 .
H2 H 0.2904(6) 0.3273(5) 0.10801(19) 0.107(2) Uiso 1.000000 R
C3 C 0.3443(9) 0.2914(8) 0.1768(2) 0.162(4) Uani 1.000000 .
H3a H 0.2582(19) 0.264(10) 0.1929(5) 0.242(7) Uiso 1.000000 GR
H3b H 0.383(10) 0.239(8) 0.1897(7) 0.242(7) Uiso 1.000000 GR
H3c H 0.406(8) 0.3874(18) 0.1826(3) 0.242(7) Uiso 1.000000 GR
C4 C 0.1655(4) 0.0793(4) 0.06889(14) 0.0564(10) Uani 1.000000 .
C5 C 0.0730(4) -0.0748(4) 0.06388(12) 0.0463(9) Uani 1.000000 .
H5 H 0.0472(4) -0.1150(4) 0.09702(12) 0.0556(11) Uiso 1.000000 R
C6 C 0.1567(5) -0.1299(5) 0.03887(16) 0.0631(12) Uani 1.000000 .
H6a H 0.1845(5) -0.0880(5) 0.00644(16) 0.0757(14) Uiso 1.000000 R
H6b H 0.2395(5) -0.1020(5) 0.05803(16) 0.0757(14) Uiso 1.000000 R
C7 C 0.0829(7) -0.2827(6) 0.0330(2) 0.0813(15) Uani 1.000000 .
H7a H 0.0064(7) -0.3091(6) 0.0105(2) 0.0976(18) Uiso 1.000000 R
H7b H 0.1450(7) -0.3082(6) 0.0177(2) 0.0976(18) Uiso 1.000000 R
C8 C 0.1688(8) -0.3221(9) 0.1248(3) 0.133(3) Uani 1.000000 .
H8a H 0.227(3) -0.351(6) 0.1094(14) 0.200(4) Uiso 1.000000 GR
H8b H 0.217(4) -0.2235(10) 0.127(2) 0.200(4) Uiso 1.000000 GR
H8c H 0.1453(9) -0.360(6) 0.1575(8) 0.200(4) Uiso 1.000000 GR
C9 C 0.6634(8) 0.4688(10) 0.0629(4) 0.175(5) Uani 1.000000 .
H9a H 0.722(4) 0.456(9) 0.0857(13) 0.263(7) Uiso 1.000000 GR
H9b H 0.6489(13) 0.413(7) 0.034(2) 0.263(7) Uiso 1.000000 GR
H9c H 0.706(5) 0.564(3) 0.053(3) 0.263(7) Uiso 1.000000 GR
C10 C -0.1613(5) -0.1178(5) 0.05768(16) 0.0643(12) Uani 1.000000 .
C11 C -0.3871(7) -0.1490(10) 0.0387(2) 0.112(3) Uani 1.000000 .
C12 C -0.4639(8) -0.1780(11) -0.0088(3) 0.152(4) Uani 1.000000 .
H12a H -0.413(4) -0.104(4) -0.0315(11) 0.228(6) Uiso 1.000000 GR
H12b H -0.476(8) -0.262(5) -0.0227(16) 0.228(6) Uiso 1.000000 GR
H12c H -0.552(4) -0.187(9) -0.0028(6) 0.228(6) Uiso 1.000000 GR
C13 C -0.4629(11) -0.2582(18) 0.0775(5) 0.247(8) Uani 1.000000 .
H13a H -0.435(14) -0.326(10) 0.076(5) 0.371(12) Uiso 1.000000 GR
H13b H -0.442(15) -0.217(3) 0.1097(7) 0.371(12) Uiso 1.000000 GR
H13c H -0.5600(14) -0.301(13) 0.072(4) 0.371(12) Uiso 1.000000 GR
C14 C -0.3466(16) -0.0070(19) 0.0549(5) 0.281(11) Uani 1.000000 .
H14a H -0.30(2) 0.010(8) 0.087(4) 0.421(16) Uiso 1.000000 GR
H14b H -0.284(17) 0.058(2) 0.031(4) 0.421(16) Uiso 1.000000 GR
H14c H -0.427(3) 0.002(7) 0.057(8) 0.421(16) Uiso 1.000000 GR
O1 O 0.5297(5) 0.4273(5) 0.08668(19) 0.1266(17) Uani 1.000000 .
O2 O 0.4866(5) 0.2098(6) 0.0860(2) 0.1206(15) Uani 1.000000 .
O3 O 0.1979(4) 0.1572(3) 0.03305(12) 0.0835(11) Uani 1.000000 .
O4 O -0.1704(5) -0.1036(7) 0.10133(11) 0.132(2) Uani 1.000000 .
O5 O -0.2610(3) -0.1457(4) 0.02542(11) 0.0775(10) Uani 1.000000 .
N1 N 0.2169(4) 0.1259(4) 0.11363(13) 0.0649(10) Uani 1.000000 .
H1 H 0.1870(4) 0.0703(4) 0.13833(13) 0.0779(12) Uiso 1.000000 R
N2 N -0.0505(3) -0.1094(3) 0.03658(11) 0.0535(8) Uani 1.000000 .
H2a H -0.0525(3) -0.1253(3) 0.00540(11) 0.0642(10) Uiso 1.000000 R
S1 S 0.01790(15) -0.37975(13) 0.08969(6) 0.0825(5) Uani 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
C1 C2 1.553(9) . ?
C1 O1 1.330(7) . ?
C1 O2 1.183(8) . ?
C2 H2 0.9800 . ?
C2 C3 1.511(8) . ?
C2 N1 1.434(6) . ?
C3 H3a 0.9600 . ?
C3 H3b 0.9600 . ?
C3 H3c 0.9600 . ?
C4 C5 1.515(6) . ?
C4 O3 1.232(5) . ?
C4 N1 1.330(5) . ?
C5 H5 0.9800 . ?
C5 C6 1.519(6) . ?
C5 N2 1.443(5) . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C6 C7 1.495(7) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 S1 1.811(5) . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C8 S1 1.759(8) . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
C9 O1 1.479(10) . ?
C10 O4 1.202(5) . ?
C10 O5 1.327(5) . ?
C10 N2 1.330(6) . ?
C11 C12 1.490(9) . ?
C11 C13 1.511(12) . ?
C11 C14 1.490(16) . ?
C11 O5 1.443(7) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2a 0.8600 . ?

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
O1 C1 C2 107.6(6) . . ?
O2 C1 C2 126.3(5) . . ?
O2 C1 O1 126.0(7) . . ?
H2 C2 C1 109.5(3) . . ?
C3 C2 C1 110.7(6) . . ?
C3 C2 H2 109.5(5) . . ?
N1 C2 C1 108.6(5) . . ?
N1 C2 H2 109.5(3) . . ?
N1 C2 C3 109.1(5) . . ?
H3a C3 C2 109.5 . . ?
H3b C3 C2 109.5 . . ?
H3b C3 H3a 109.5 . . ?
H3c C3 C2 109.5 . . ?
H3c C3 H3a 109.5 . . ?
H3c C3 H3b 109.5 . . ?
O3 C4 C5 122.1(3) . . ?
N1 C4 C5 116.5(3) . . ?
N1 C4 O3 121.3(4) . . ?
H5 C5 C4 108.70(18) . . ?
C6 C5 C4 107.2(3) . . ?
C6 C5 H5 108.7(2) . . ?
N2 C5 C4 111.8(3) . . ?
N2 C5 H5 108.70(18) . . ?
N2 C5 C6 111.7(3) . . ?
H6a C6 C5 108.6(2) . . ?
H6b C6 C5 108.6(2) . . ?
H6b C6 H6a 107.6 . . ?
C7 C6 C5 114.5(4) . . ?
C7 C6 H6a 108.6(3) . . ?
C7 C6 H6b 108.6(3) . . ?
H7a C7 C6 108.5(3) . . ?
H7b C7 C6 108.5(3) . . ?
H7b C7 H7a 107.5 . . ?
S1 C7 C6 115.2(3) . . ?
S1 C7 H7a 108.5(2) . . ?
S1 C7 H7b 108.47(18) . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
S1 C8 H8a 109.5 . . ?
S1 C8 H8b 109.5 . . ?
S1 C8 H8c 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
O1 C9 H9a 109.5 . . ?
O1 C9 H9b 109.5 . . ?
O1 C9 H9c 109.5 . . ?
O5 C10 O4 124.0(4) . . ?
N2 C10 O4 123.4(4) . . ?
N2 C10 O5 112.6(4) . . ?
C13 C11 C12 113.0(9) . . ?
C14 C11 C12 108.7(8) . . ?
C14 C11 C13 114.3(11) . . ?
O5 C11 C12 104.2(5) . . ?
O5 C11 C13 109.9(6) . . ?
O5 C11 C14 106.0(8) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14a C14 C11 109.5 . . ?
H14b C14 C11 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C11 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C9 O1 C1 113.6(7) . . ?
C11 O5 C10 122.9(4) . . ?
C4 N1 C2 121.8(4) . . ?
H1 N1 C2 119.1(3) . . ?
H1 N1 C4 119.1(2) . . ?
C10 N2 C5 122.7(3) . . ?
H2a N2 C5 118.67(18) . . ?
H2a N2 C10 118.7(2) . . ?
C8 S1 C7 102.2(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
C1 C2 N1 C4 -66.5(6) . . . . ?
C2 N1 C4 C5 170.9(5) . . . . ?
C2 N1 C4 O3 -5.2(6) . . . . ?
C4 C5 C6 C7 177.3(4) . . . . ?
C4 C5 N2 C10 -84.5(4) . . . . ?
C5 C6 C7 S1 -56.6(4) . . . . ?
C5 N2 C10 O4 -3.6(6) . . . . ?
C5 N2 C10 O5 177.5(4) . . . . ?
C10 O5 C11 C12 177.7(8) . . . . ?
C10 O5 C11 C13 -61.0(9) . . . . ?
C10 O5 C11 C14 63.0(8) . . . . ?


_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 1.101
_oxdiff_exptl_absorpt_empirical_full_min 0.921
_chemical_melting_point          398.2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
####################################################################### 
# 
# 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_cmpd_2_188K
_database_code_depnum_ccdc_archive 'CCDC 2342412'
loop_
_audit_author_name
_audit_author_address
'Hiroki Takahashi'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2024-03-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C16 H30 N2 O5 S'
_chemical_formula_sum            'C16 H30 N2 O5 S'
_chemical_formula_weight         362.493
_chemical_absolute_configuration unk
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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           ' P 65'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x-y,x,z+5/6
3 y,-x+y,z+1/6
4 -y,x-y,z+2/3
5 -x+y,-x,z+1/3
6 -x,-y,z+1/2

_symmetry_Int_Tables_number      170
_cell_length_a                   11.3887(8)
_cell_length_b                   11.3887(8)
_cell_length_c                   27.3424(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3071.3(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    8199
_cell_measurement_temperature    188(2)
_cell_measurement_theta_max      30.4340
_cell_measurement_theta_min      2.3550
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       needle
_exptl_crystal_F_000             1177.333
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_Laue_measured_fraction_full 0.9984
_diffrn_reflns_Laue_measured_fraction_max 0.9487
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            29375
_diffrn_reflns_point_group_measured_fraction_full 0.9677
_diffrn_reflns_point_group_measured_fraction_max 0.8591
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.31
_diffrn_reflns_theta_min         3.04
_diffrn_ambient_temperature      188.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9487
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   16.00    --  -20.00  50.00 300.00  360
  2  ω   -110.00  70.00   0.50   16.00    --  -20.00  50.00 210.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0511991000
_diffrn_orient_matrix_UB_12      0.0048572000
_diffrn_orient_matrix_UB_13      0.0131098000
_diffrn_orient_matrix_UB_21      -0.0505379000
_diffrn_orient_matrix_UB_22      -0.0557517000
_diffrn_orient_matrix_UB_23      -0.0133796000
_diffrn_orient_matrix_UB_31      -0.0003001000
_diffrn_orient_matrix_UB_32      -0.0450605000
_diffrn_orient_matrix_UB_33      0.0179584000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.766
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              30
_reflns_limit_l_min              -39
_reflns_number_gt                3510
_reflns_number_total             5754
_reflns_odcompleteness_completeness 94.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.24
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.8235
_refine_diff_density_min         -0.6762
_refine_diff_density_rms         0.1095
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_d_res_high            0.6838
_refine_ls_d_res_low             6.6937
_refine_ls_goodness_of_fit_ref   1.0308
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5754
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0754
_refine_ls_restrained_S_all      1.0308
_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)+(0.0687P)²+0.8027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1646
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2a)
2.d Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C12(H12a,H12b,H12c), C13(H13a,H13b,H13c),
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
;
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
C1 C 0.4614(4) 0.2889(4) 0.15569(14) 0.0400(9) Uani 1.000000 .
C2 C 0.3370(4) 0.2821(3) 0.17664(12) 0.0360(8) Uani 1.000000 .
H2 H 0.3121(4) 0.3355(3) 0.15543(12) 0.0431(10) Uiso 1.000000 R
C4 C 0.1623(3) 0.0871(3) 0.13404(12) 0.0261(6) Uani 1.000000 .
C5 C 0.0638(3) -0.0670(3) 0.13494(11) 0.0252(6) Uani 1.000000 .
H5 H 0.0430(3) -0.0984(3) 0.16888(11) 0.0303(8) Uiso 1.000000 R
C3 C 0.3664(4) 0.3464(4) 0.22748(15) 0.0481(10) Uani 1.000000 .
H3 H 0.4374(4) 0.4412(4) 0.22316(15) 0.0577(12) Uiso 1.000000 R
C6 C 0.1402(4) -0.1300(3) 0.11023(12) 0.0323(7) Uani 1.000000 .
H6a H 0.1647(4) -0.0935(3) 0.07740(12) 0.0387(9) Uiso 1.000000 R
H6b H 0.2238(4) -0.1018(3) 0.12808(12) 0.0387(9) Uiso 1.000000 R
C7 C 0.0647(4) -0.2812(4) 0.10699(13) 0.0382(8) Uani 1.000000 .
H7a H -0.0134(4) -0.3088(4) 0.08593(13) 0.0458(10) Uiso 1.000000 R
H7b H 0.1229(4) -0.3096(4) 0.09141(13) 0.0458(10) Uiso 1.000000 R
C8 C 0.1607(5) -0.3121(5) 0.19663(16) 0.0631(13) Uani 1.000000 .
H8a H 0.2175(14) -0.338(3) 0.1791(6) 0.0946(19) Uiso 1.000000 GR
H8b H 0.2059(16) -0.2151(6) 0.1995(10) 0.0946(19) Uiso 1.000000 GR
H8c H 0.1422(6) -0.352(2) 0.2287(4) 0.0946(19) Uiso 1.000000 GR
C9 C 0.6779(5) 0.4413(6) 0.1226(2) 0.099(2) Uani 1.000000 .
H9a H 0.717(2) 0.403(4) 0.1438(9) 0.149(3) Uiso 1.000000 GR
H9b H 0.6636(9) 0.401(4) 0.0907(8) 0.149(3) Uiso 1.000000 GR
H9c H 0.7385(18) 0.5373(7) 0.1200(17) 0.149(3) Uiso 1.000000 GR
C10 C -0.1697(3) -0.1162(3) 0.13272(12) 0.0307(7) Uani 1.000000 .
C11 C -0.4042(4) -0.1697(4) 0.11725(13) 0.0406(9) Uani 1.000000 .
C12 C -0.4777(5) -0.1872(6) 0.06962(16) 0.0679(15) Uani 1.000000 .
H12a H -0.4280(19) -0.1074(15) 0.0500(6) 0.102(2) Uiso 1.000000 GR
H12b H -0.485(3) -0.264(2) 0.0525(6) 0.102(2) Uiso 1.000000 GR
H12c H -0.5666(14) -0.201(4) 0.07607(17) 0.102(2) Uiso 1.000000 GR
C13 C -0.4725(5) -0.2990(5) 0.14633(18) 0.0613(13) Uani 1.000000 .
H13a H -0.465(3) -0.3685(10) 0.1291(6) 0.0919(19) Uiso 1.000000 GR
H13b H -0.430(2) -0.2843(10) 0.1777(5) 0.0919(19) Uiso 1.000000 GR
H13c H -0.5664(9) -0.3266(19) 0.1507(11) 0.0919(19) Uiso 1.000000 GR
C14 C -0.3936(5) -0.0515(5) 0.1457(2) 0.0667(13) Uani 1.000000 .
H14a H -0.348(3) -0.043(2) 0.1762(6) 0.100(2) Uiso 1.000000 GR
H14b H -0.343(3) 0.0303(7) 0.1271(6) 0.100(2) Uiso 1.000000 GR
H14c H -0.4828(5) -0.0659(18) 0.1519(11) 0.100(2) Uiso 1.000000 GR
C15 C 0.4227(5) 0.2849(4) 0.26246(16) 0.0673(14) Uani 1.000000 .
H15a H 0.3576(15) 0.1906(10) 0.2670(10) 0.101(2) Uiso 1.000000 GR
H15b H 0.5050(19) 0.294(3) 0.2493(6) 0.101(2) Uiso 1.000000 GR
H15c H 0.441(3) 0.331(2) 0.2933(4) 0.101(2) Uiso 1.000000 GR
C16 C 0.2432(5) 0.3492(6) 0.2471(2) 0.087(2) Uani 1.000000 .
H16a H 0.1708(16) 0.2580(6) 0.2523(16) 0.131(3) Uiso 1.000000 GR
H16b H 0.2659(14) 0.398(4) 0.2775(9) 0.131(3) Uiso 1.000000 GR
H16c H 0.215(3) 0.394(4) 0.2239(8) 0.131(3) Uiso 1.000000 GR
O1 O 0.5497(3) 0.4161(3) 0.14242(12) 0.0672(9) Uani 1.000000 .
O2 O 0.4834(3) 0.1974(3) 0.15141(11) 0.0589(8) Uani 1.000000 .
O3 O 0.1868(3) 0.1512(2) 0.09582(8) 0.0414(6) Uani 1.000000 .
O4 O -0.1800(3) -0.1106(3) 0.17657(8) 0.0510(8) Uani 1.000000 .
O5 O -0.2694(2) -0.1415(3) 0.10054(8) 0.0366(6) Uani 1.000000 .
S1 S 0.00644(11) -0.37023(10) 0.16456(4) 0.0445(3) Uani 1.000000 .
N1 N 0.2244(3) 0.1426(3) 0.17625(9) 0.0288(6) Uani 1.000000 .
H1 H 0.1984(3) 0.0965(3) 0.20293(9) 0.0346(7) Uiso 1.000000 R
N2 N -0.0599(3) -0.1009(3) 0.10933(9) 0.0326(6) Uani 1.000000 .
H2a H -0.0631(3) -0.1116(3) 0.07812(9) 0.0391(8) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.494(5) . ?
C1 O1 1.336(5) . ?
C1 O2 1.192(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.528(5) . ?
C2 N1 1.460(4) . ?
C4 C5 1.539(4) . ?
C4 O3 1.225(4) . ?
C4 N1 1.336(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.534(4) . ?
C5 N2 1.443(4) . ?
C3 H3 0.9800 . ?
C3 C15 1.504(6) . ?
C3 C16 1.517(7) . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C6 C7 1.494(5) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 S1 1.809(4) . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C8 S1 1.769(5) . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
C9 O1 1.446(6) . ?
C10 O4 1.209(4) . ?
C10 O5 1.349(4) . ?
C10 N2 1.336(4) . ?
C11 C12 1.507(5) . ?
C11 C13 1.503(6) . ?
C11 C14 1.506(6) . ?
C11 O5 1.475(4) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?
C16 H16a 0.9600 . ?
C16 H16b 0.9600 . ?
C16 H16c 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2a 0.8600 . ?

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
O1 C1 C2 109.9(3) . . ?
O2 C1 C2 126.9(4) . . ?
O2 C1 O1 123.2(4) . . ?
H2 C2 C1 107.6(2) . . ?
C3 C2 C1 110.4(3) . . ?
C3 C2 H2 107.6(2) . . ?
N1 C2 C1 110.3(3) . . ?
N1 C2 H2 107.62(17) . . ?
N1 C2 C3 113.0(3) . . ?
O3 C4 C5 120.8(3) . . ?
N1 C4 C5 115.9(3) . . ?
N1 C4 O3 123.1(3) . . ?
H5 C5 C4 109.66(16) . . ?
C6 C5 C4 105.4(2) . . ?
C6 C5 H5 109.66(17) . . ?
N2 C5 C4 110.8(2) . . ?
N2 C5 H5 109.66(16) . . ?
N2 C5 C6 111.6(3) . . ?
H3 C3 C2 106.33(19) . . ?
C15 C3 C2 113.4(3) . . ?
C15 C3 H3 106.3(2) . . ?
C16 C3 C2 110.3(4) . . ?
C16 C3 H3 106.3(3) . . ?
C16 C3 C15 113.5(4) . . ?
H6a C6 C5 108.39(17) . . ?
H6b C6 C5 108.39(17) . . ?
H6b C6 H6a 107.5 . . ?
C7 C6 C5 115.5(3) . . ?
C7 C6 H6a 108.39(19) . . ?
C7 C6 H6b 108.4(2) . . ?
H7a C7 C6 108.4(2) . . ?
H7b C7 C6 108.37(19) . . ?
H7b C7 H7a 107.4 . . ?
S1 C7 C6 115.6(3) . . ?
S1 C7 H7a 108.37(13) . . ?
S1 C7 H7b 108.37(12) . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
S1 C8 H8a 109.5 . . ?
S1 C8 H8b 109.5 . . ?
S1 C8 H8c 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
O1 C9 H9a 109.5 . . ?
O1 C9 H9b 109.5 . . ?
O1 C9 H9c 109.5 . . ?
O5 C10 O4 124.4(3) . . ?
N2 C10 O4 125.2(3) . . ?
N2 C10 O5 110.4(3) . . ?
C13 C11 C12 110.3(4) . . ?
C14 C11 C12 110.8(4) . . ?
C14 C11 C13 112.0(4) . . ?
O5 C11 C12 102.1(3) . . ?
O5 C11 C13 110.5(3) . . ?
O5 C11 C14 110.8(3) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14a C14 C11 109.5 . . ?
H14b C14 C11 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C11 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H15a C15 C3 109.5 . . ?
H15b C15 C3 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C3 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H16a C16 C3 109.5 . . ?
H16b C16 C3 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C3 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
C9 O1 C1 117.1(4) . . ?
C11 O5 C10 121.2(2) . . ?
C8 S1 C7 101.8(2) . . ?
C4 N1 C2 119.4(3) . . ?
H1 N1 C2 120.32(17) . . ?
H1 N1 C4 120.32(17) . . ?
C10 N2 C5 121.8(3) . . ?
H2a N2 C5 119.08(16) . . ?
H2a N2 C10 119.08(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C15 -55.8(4) . . . . ?
C1 C2 C3 C16 175.7(4) . . . . ?
C1 C2 N1 C4 -75.0(3) . . . . ?
C2 N1 C4 C5 168.8(3) . . . . ?
C2 N1 C4 O3 -6.7(3) . . . . ?
C4 C5 C6 C7 179.6(3) . . . . ?
C4 C5 N2 C10 -95.0(3) . . . . ?
C5 C6 C7 S1 -57.1(3) . . . . ?
C5 N2 C10 O4 -4.0(4) . . . . ?
C5 N2 C10 O5 177.2(3) . . . . ?
C10 O5 C11 C12 178.5(4) . . . . ?
C10 O5 C11 C13 -64.2(3) . . . . ?
C10 O5 C11 C14 60.5(4) . . . . ?


_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 1.109
_oxdiff_exptl_absorpt_empirical_full_min 0.934
_chemical_melting_point          393.2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
####################################################################### 
# 
# 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_cmpd_3_188K
_database_code_depnum_ccdc_archive 'CCDC 2342427'
loop_
_audit_author_name
_audit_author_address
'Hiroki Takahashi'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2024-03-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C17 H32 N2 O5 S'
_chemical_formula_sum            'C17 H32 N2 O5 S'
_chemical_formula_weight         376.520
_chemical_absolute_configuration unk
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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           ' P 65'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x-y,x,z+5/6
3 y,-x+y,z+1/6
4 -y,x-y,z+2/3
5 -x+y,-x,z+1/3
6 -x,-y,z+1/2

_symmetry_Int_Tables_number      170
_cell_length_a                   11.4929(7)
_cell_length_b                   11.4929(7)
_cell_length_c                   27.9288(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3194.8(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9683
_cell_measurement_temperature    188(2)
_cell_measurement_theta_max      31.0920
_cell_measurement_theta_min      2.2290
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       needle
_exptl_crystal_F_000             1225.348
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9612
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            30468
_diffrn_reflns_point_group_measured_fraction_full 0.9984
_diffrn_reflns_point_group_measured_fraction_max 0.9276
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.17
_diffrn_reflns_theta_min         3.00
_diffrn_ambient_temperature      188.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9612
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   16.00    --  -20.00  35.00  30.00  360
  2  ω   -110.00  70.00   0.50   16.00    --  -20.00  35.00 120.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0572140000
_diffrn_orient_matrix_UB_12      -0.0131600000
_diffrn_orient_matrix_UB_13      -0.0137720000
_diffrn_orient_matrix_UB_21      0.0303598000
_diffrn_orient_matrix_UB_22      0.0692001000
_diffrn_orient_matrix_UB_23      -0.0057269000
_diffrn_orient_matrix_UB_31      0.0298215000
_diffrn_orient_matrix_UB_32      -0.0105416000
_diffrn_orient_matrix_UB_33      -0.0205514000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.893
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              40
_reflns_limit_l_min              -39
_reflns_number_gt                4224
_reflns_number_total             6393
_reflns_odcompleteness_completeness 96.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.11
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.8384
_refine_diff_density_min         -0.4986
_refine_diff_density_rms         0.1002
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_d_res_high            0.6865
_refine_ls_d_res_low             6.7990
_refine_ls_goodness_of_fit_ref   1.0291
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    47
_refine_ls_number_parameters     233
_refine_ls_number_reflns         6393
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      1.0291
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0785P)²+0.9938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1700
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C6(H6a,H6b), C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2a)
2.d Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C12(H12a,H12b,H12c), C13(H13a,H13b,H13c),
 C14(H14a,H14b,H14c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
;
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
C1 C 0.4314(3) 0.2464(3) 0.12848(11) 0.0303(6) Uani 1.000000 .
C2 C 0.3072(3) 0.2302(3) 0.15417(10) 0.0255(6) Uani 1.000000 .
H2 H 0.2831(3) 0.2938(3) 0.14043(10) 0.0306(7) Uiso 1.000000 R
C3 C 0.3380(3) 0.2619(3) 0.20711(10) 0.0280(6) Uani 1.000000 .
H3a H 0.3415(3) 0.1878(3) 0.22229(10) 0.0336(7) Uiso 1.000000 R
H3b H 0.4261(3) 0.3412(3) 0.21027(10) 0.0336(7) Uiso 1.000000 R
C4 C 0.1399(3) 0.0487(3) 0.10540(10) 0.0224(5) Uani 1.000000 .
C5 C 0.0366(3) -0.1013(3) 0.10385(9) 0.0234(5) Uani 1.000000 .
H5 H 0.0130(3) -0.1342(3) 0.13679(9) 0.0281(7) Uiso 1.000000 R
C6 C 0.1062(3) -0.1706(3) 0.08041(11) 0.0325(7) Uani 1.000000 .
H6a H 0.1250(3) -0.1421(3) 0.04725(11) 0.0390(8) Uiso 1.000000 R
H6b H 0.1916(3) -0.1406(3) 0.09630(11) 0.0390(8) Uiso 1.000000 R
C7 C 0.0266(4) -0.3221(3) 0.08185(13) 0.0432(8) Uani 1.000000 .
H7a H -0.0533(4) -0.3521(3) 0.06237(13) 0.0519(10) Uiso 1.000000 R
H7b H 0.0801(4) -0.3563(3) 0.06728(13) 0.0519(10) Uiso 1.000000 R
C8 C 0.1342(6) -0.3357(5) 0.16848(19) 0.0764(15) Uani 1.000000 .
H8a H 0.1213(6) -0.362(3) 0.2016(4) 0.115(2) Uiso 1.000000 GR
H8b H 0.1821(17) -0.373(3) 0.1528(9) 0.115(2) Uiso 1.000000 GR
H8c H 0.1849(16) -0.2395(6) 0.1662(12) 0.115(2) Uiso 1.000000 GR
C9 C 0.6376(4) 0.4117(5) 0.0957(2) 0.0723(15) Uani 1.000000 .
H9a H 0.6986(12) 0.416(4) 0.1201(3) 0.108(2) Uiso 1.000000 GR
H9b H 0.6255(7) 0.345(2) 0.0724(10) 0.108(2) Uiso 1.000000 GR
H9c H 0.6737(18) 0.4977(18) 0.0804(12) 0.108(2) Uiso 1.000000 GR
C10 C -0.1954(3) -0.1494(3) 0.10225(10) 0.0269(6) Uani 1.000000 .
C11 C -0.4345(3) -0.2221(3) 0.08961(12) 0.0379(8) Uani 1.000000 .
C12 C -0.5216(4) -0.2825(9) 0.04617(17) 0.117(3) Uani 1.000000 .
H12a H -0.608(2) -0.292(5) 0.0519(8) 0.175(4) Uiso 1.000000 GR
H12b H -0.481(3) -0.225(3) 0.0191(5) 0.175(4) Uiso 1.000000 GR
H12c H -0.531(5) -0.369(3) 0.0398(12) 0.175(4) Uiso 1.000000 GR
C13 C -0.4848(4) -0.3211(5) 0.12950(18) 0.0666(13) Uani 1.000000 .
H13a H -0.429(2) -0.2820(12) 0.1572(4) 0.100(2) Uiso 1.000000 GR
H13b H -0.5757(12) -0.345(3) 0.1369(8) 0.100(2) Uiso 1.000000 GR
H13c H -0.482(3) -0.3999(14) 0.1201(5) 0.100(2) Uiso 1.000000 GR
C14 C -0.4262(5) -0.0955(5) 0.1026(3) 0.119(3) Uani 1.000000 .
H14a H -0.376(5) -0.063(3) 0.1318(11) 0.178(4) Uiso 1.000000 GR
H14b H -0.382(5) -0.0311(19) 0.0775(9) 0.178(4) Uiso 1.000000 GR
H14c H -0.5151(6) -0.1095(13) 0.107(2) 0.178(4) Uiso 1.000000 GR
C15 C 0.2346(3) 0.2861(3) 0.23379(11) 0.0288(6) Uani 1.000000 .
H15 H 0.1441(3) 0.2174(3) 0.22388(11) 0.0346(7) Uiso 1.000000 R
C16 C 0.2473(4) 0.2757(3) 0.28784(11) 0.0433(8) Uani 1.000000 .
H16a H 0.229(3) 0.1868(8) 0.29580(15) 0.0649(13) Uiso 1.000000 GR
H16b H 0.3368(8) 0.3399(18) 0.29778(17) 0.0649(13) Uiso 1.000000 GR
H16c H 0.1842(18) 0.294(3) 0.30392(12) 0.0649(13) Uiso 1.000000 GR
C17 C 0.2549(4) 0.4241(3) 0.22093(14) 0.0433(8) Uani 1.000000 .
H17a H 0.3457(8) 0.4918(4) 0.2280(8) 0.0649(12) Uiso 1.000000 GR
H17b H 0.238(2) 0.4266(9) 0.1874(2) 0.0649(12) Uiso 1.000000 GR
H17c H 0.1940(18) 0.4407(11) 0.2392(7) 0.0649(12) Uiso 1.000000 GR
N1 N 0.1945(2) 0.0950(2) 0.14823(8) 0.0239(5) Uani 1.000000 .
H1 H 0.1625(2) 0.0437(2) 0.17286(8) 0.0287(6) Uiso 1.000000 R
N2 N -0.0857(2) -0.1316(2) 0.07845(8) 0.0278(5) Uani 1.000000 .
H2a H -0.0881(2) -0.1384(2) 0.04776(8) 0.0334(6) Uiso 1.000000 R
O1 O 0.5095(2) 0.3757(2) 0.11726(11) 0.0572(8) Uani 1.000000 .
O2 O 0.4585(3) 0.1610(3) 0.12141(9) 0.0454(6) Uani 1.000000 .
O3 O 0.1747(2) 0.1193(2) 0.06930(7) 0.0309(5) Uani 1.000000 .
O4 O -0.1980(2) -0.1277(3) 0.14438(8) 0.0431(6) Uani 1.000000 .
O5 O -0.3017(2) -0.1962(3) 0.07273(8) 0.0476(6) Uani 1.000000 .
S1 S -0.02452(11) -0.39579(9) 0.14058(4) 0.0490(3) Uani 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
C1 C2 1.524(4) . ?
C1 O1 1.333(4) . ?
C1 O2 1.185(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.522(4) . ?
C2 N1 1.451(4) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 C15 1.542(4) . ?
C4 C5 1.529(4) . ?
C4 N1 1.332(3) . ?
C4 O3 1.229(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.529(4) . ?
C5 N2 1.452(4) . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C6 C7 1.510(5) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 S1 1.804(4) . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C8 S1 1.775(5) . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
C9 O1 1.445(4) . ?
C10 N2 1.348(4) . ?
C10 O4 1.206(4) . ?
C10 O5 1.343(4) . ?
C11 C12 1.504(6) . ?
C11 C13 1.487(5) . ?
C11 C14 1.456(6) . ?
C11 O5 1.478(4) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C15 H15 0.9800 . ?
C15 C16 1.527(4) . ?
C15 C17 1.525(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 H1 0.8600 . ?
N2 H2a 0.8600 . ?

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
O1 C1 C2 108.4(3) . . ?
O2 C1 C2 126.5(3) . . ?
O2 C1 O1 125.0(3) . . ?
H2 C2 C1 108.73(16) . . ?
C3 C2 C1 109.6(2) . . ?
C3 C2 H2 108.73(16) . . ?
N1 C2 C1 110.9(2) . . ?
N1 C2 H2 108.73(15) . . ?
N1 C2 C3 110.1(2) . . ?
H3a C3 C2 108.79(16) . . ?
H3b C3 C2 108.79(15) . . ?
H3b C3 H3a 107.7 . . ?
C15 C3 C2 113.9(2) . . ?
C15 C3 H3a 108.79(16) . . ?
C15 C3 H3b 108.79(15) . . ?
N1 C4 C5 114.9(2) . . ?
O3 C4 C5 122.3(2) . . ?
O3 C4 N1 122.7(2) . . ?
H5 C5 C4 108.51(14) . . ?
C6 C5 C4 106.6(2) . . ?
C6 C5 H5 108.51(15) . . ?
N2 C5 C4 113.4(2) . . ?
N2 C5 H5 108.51(14) . . ?
N2 C5 C6 111.2(2) . . ?
H6a C6 C5 108.62(15) . . ?
H6b C6 C5 108.62(16) . . ?
H6b C6 H6a 107.6 . . ?
C7 C6 C5 114.6(3) . . ?
C7 C6 H6a 108.62(18) . . ?
C7 C6 H6b 108.62(19) . . ?
H7a C7 C6 108.36(19) . . ?
H7b C7 C6 108.36(18) . . ?
H7b C7 H7a 107.4 . . ?
S1 C7 C6 115.7(2) . . ?
S1 C7 H7a 108.36(12) . . ?
S1 C7 H7b 108.36(12) . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
S1 C8 H8a 109.5 . . ?
S1 C8 H8b 109.5 . . ?
S1 C8 H8c 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
O1 C9 H9a 109.5 . . ?
O1 C9 H9b 109.5 . . ?
O1 C9 H9c 109.5 . . ?
O4 C10 N2 124.6(3) . . ?
O5 C10 N2 110.7(2) . . ?
O5 C10 O4 124.8(3) . . ?
C13 C11 C12 109.7(4) . . ?
C14 C11 C12 111.0(5) . . ?
C14 C11 C13 112.6(5) . . ?
O5 C11 C12 102.6(3) . . ?
O5 C11 C13 111.1(3) . . ?
O5 C11 C14 109.5(3) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14a C14 C11 109.5 . . ?
H14b C14 C11 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C11 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H15 C15 C3 108.70(15) . . ?
C16 C15 C3 110.6(3) . . ?
C16 C15 H15 108.70(18) . . ?
C17 C15 C3 110.1(2) . . ?
C17 C15 H15 108.70(18) . . ?
C17 C15 C16 110.1(3) . . ?
H16a C16 C15 109.5 . . ?
H16b C16 C15 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C15 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
H17a C17 C15 109.5 . . ?
H17b C17 C15 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C15 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
C4 N1 C2 121.3(2) . . ?
H1 N1 C2 119.33(14) . . ?
H1 N1 C4 119.33(15) . . ?
C10 N2 C5 121.0(2) . . ?
H2a N2 C5 119.48(14) . . ?
H2a N2 C10 119.48(15) . . ?
C9 O1 C1 116.0(3) . . ?
C11 O5 C10 121.7(2) . . ?
C8 S1 C7 100.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C15 164.3(2) . . . . ?
C1 C2 N1 C4 -65.3(3) . . . . ?
C2 C3 C15 C16 163.2(3) . . . . ?
C2 C3 C15 C17 -75.0(3) . . . . ?
C2 N1 C4 C5 171.3(2) . . . . ?
C2 N1 C4 O3 -4.9(3) . . . . ?
C4 C5 C6 C7 171.8(2) . . . . ?
C4 C5 N2 C10 -96.7(3) . . . . ?
C5 C6 C7 S1 -56.1(3) . . . . ?
C5 N2 C10 O4 8.6(3) . . . . ?
C5 N2 C10 O5 -170.6(3) . . . . ?
C10 O5 C11 C12 -175.7(5) . . . . ?
C10 O5 C11 C13 -58.5(4) . . . . ?
C10 O5 C11 C14 66.5(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.075
_oxdiff_exptl_absorpt_empirical_full_min 0.926
_chemical_melting_point          381.8
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
####################################################################### 
# 
# 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_cmpd_1_188K
_database_code_depnum_ccdc_archive 'CCDC 2298632'
loop_
_audit_author_name
_audit_author_address
'Hiroki Takahashi'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C14 H26 N2 O5 S'
_chemical_formula_sum            'C14 H26 N2 O5 S'
_chemical_formula_weight         334.439
_chemical_absolute_configuration unk
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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           ' P 65'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x-y,x,z+5/6
3 y,-x+y,z+1/6
4 -y,x-y,z+2/3
5 -x+y,-x,z+1/3
6 -x,-y,z+1/2

_symmetry_Int_Tables_number      170
_cell_length_a                   11.1876(8)
_cell_length_b                   11.1876(8)
_cell_length_c                   26.9537(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2921.6(5)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    7863
_cell_measurement_temperature    188(2)
_cell_measurement_theta_max      31.0260
_cell_measurement_theta_min      2.3390
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_F_000             1081.303
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.9983
_diffrn_reflns_Laue_measured_fraction_max 0.9644
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            27857
_diffrn_reflns_point_group_measured_fraction_full 0.9963
_diffrn_reflns_point_group_measured_fraction_max 0.9338
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.20
_diffrn_reflns_theta_min         2.59
_diffrn_ambient_temperature      188.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9644
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   16.00    --  -20.00  50.00 270.00  360
  2  ω   -110.00  70.00   0.50   16.00    --  -20.00  50.00 180.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0643920000
_diffrn_orient_matrix_UB_12      0.0024027000
_diffrn_orient_matrix_UB_13      0.0021754000
_diffrn_orient_matrix_UB_21      -0.0343771000
_diffrn_orient_matrix_UB_22      -0.0694295000
_diffrn_orient_matrix_UB_23      0.0083590000
_diffrn_orient_matrix_UB_31      -0.0059188000
_diffrn_orient_matrix_UB_32      -0.0230603000
_diffrn_orient_matrix_UB_33      -0.0248458000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.902
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              39
_reflns_limit_l_min              -38
_reflns_number_gt                3321
_reflns_number_total             5911
_reflns_odcompleteness_completeness 96.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.13
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.5713
_refine_diff_density_min         -0.3609
_refine_diff_density_rms         0.0840
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.04(12)
_refine_ls_d_res_high            0.6859
_refine_ls_d_res_low             7.8668
_refine_ls_goodness_of_fit_ref   1.0289
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     205
_refine_ls_number_reflns         5911
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.0774
_refine_ls_restrained_S_all      1.0289
_refine_ls_shift/su_max          0.0040
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0838P)²+0.9196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1692
_refine_ls_wR_factor_ref         0.1984
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2a)
2.d Idealised Me refined as rotating group:
 C3(H3a,H3b,H3c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C12(H12a,H12b,H12c),
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c)
;
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
C1 C 0.4559(5) 0.2960(5) 0.11377(16) 0.0803(15) Uani 1.000000 .
C2 C 0.3212(5) 0.2695(4) 0.14058(16) 0.0796(14) Uani 1.000000 .
H2 H 0.2907(5) 0.3306(4) 0.12650(16) 0.0955(17) Uiso 1.000000 R
C3 C 0.3444(8) 0.2962(7) 0.1956(2) 0.146(3) Uani 1.000000 .
H3a H 0.2571(9) 0.262(7) 0.2120(4) 0.219(5) Uiso 1.000000 GR
H3b H 0.390(7) 0.250(6) 0.2084(5) 0.219(5) Uiso 1.000000 GR
H3c H 0.400(6) 0.3936(9) 0.2013(3) 0.219(5) Uiso 1.000000 GR
C4 C 0.1665(4) 0.0822(3) 0.08733(11) 0.0479(8) Uani 1.000000 .
C5 C 0.0735(3) -0.0732(3) 0.08195(10) 0.0393(7) Uani 1.000000 .
H5 H 0.0472(3) -0.1142(3) 0.11509(10) 0.0472(8) Uiso 1.000000 R
C6 C 0.1567(4) -0.1283(4) 0.05663(13) 0.0529(9) Uani 1.000000 .
H6a H 0.1839(4) -0.0865(4) 0.02403(13) 0.0634(10) Uiso 1.000000 R
H6b H 0.2403(4) -0.1001(4) 0.07560(13) 0.0634(10) Uiso 1.000000 R
C7 C 0.0823(5) -0.2823(4) 0.05084(15) 0.0659(11) Uani 1.000000 .
H7a H 0.0057(5) -0.3089(4) 0.02818(15) 0.0791(13) Uiso 1.000000 R
H7b H 0.1448(5) -0.3081(4) 0.03565(15) 0.0791(13) Uiso 1.000000 R
C8 C 0.1670(7) -0.3236(7) 0.1430(2) 0.117(2) Uani 1.000000 .
H8a H 0.229(2) -0.345(5) 0.1259(10) 0.176(3) Uiso 1.000000 GR
H8b H 0.211(3) -0.2256(11) 0.1479(17) 0.176(3) Uiso 1.000000 GR
H8c H 0.1432(9) -0.369(4) 0.1746(8) 0.176(3) Uiso 1.000000 GR
C9 C 0.6620(7) 0.4743(8) 0.0806(3) 0.163(4) Uani 1.000000 .
H9a H 0.724(3) 0.469(8) 0.1039(9) 0.244(6) Uiso 1.000000 GR
H9b H 0.6483(15) 0.415(5) 0.0530(19) 0.244(6) Uiso 1.000000 GR
H9c H 0.700(4) 0.568(3) 0.069(3) 0.244(6) Uiso 1.000000 GR
C10 C -0.1611(4) -0.1154(5) 0.07584(13) 0.0580(10) Uani 1.000000 .
C11 C -0.3895(6) -0.1495(8) 0.05710(18) 0.102(2) Uani 1.000000 .
C12 C -0.4675(6) -0.1797(9) 0.0096(2) 0.131(3) Uani 1.000000 .
H12a H -0.418(3) -0.105(3) -0.0131(9) 0.196(4) Uiso 1.000000 GR
H12b H -0.478(6) -0.263(4) -0.0046(12) 0.196(4) Uiso 1.000000 GR
H12c H -0.557(3) -0.191(7) 0.0158(4) 0.196(4) Uiso 1.000000 GR
C13 C -0.4649(9) -0.2579(16) 0.0961(4) 0.252(7) Uani 1.000000 .
H13a H -0.435(13) -0.325(10) 0.095(4) 0.378(11) Uiso 1.000000 GR
H13b H -0.445(14) -0.215(3) 0.1282(7) 0.378(11) Uiso 1.000000 GR
H13c H -0.5624(14) -0.303(12) 0.090(4) 0.378(11) Uiso 1.000000 GR
C14 C -0.3536(13) -0.0105(14) 0.0734(4) 0.241(7) Uani 1.000000 .
H14a H -0.308(15) 0.008(6) 0.105(3) 0.362(11) Uiso 1.000000 GR
H14b H -0.293(13) 0.0559(18) 0.050(3) 0.362(11) Uiso 1.000000 GR
H14c H -0.4361(18) -0.005(5) 0.076(6) 0.362(11) Uiso 1.000000 GR
N1 N 0.2153(3) 0.1272(3) 0.13226(11) 0.0584(8) Uani 1.000000 .
H1 H 0.1838(3) 0.0713(3) 0.15698(11) 0.0701(10) Uiso 1.000000 R
N2 N -0.0510(3) -0.1071(3) 0.05421(9) 0.0449(6) Uani 1.000000 .
H2a H -0.0531(3) -0.1222(3) 0.02285(9) 0.0539(8) Uiso 1.000000 R
O1 O 0.5304(4) 0.4314(4) 0.10467(16) 0.1223(15) Uani 1.000000 .
O2 O 0.4858(4) 0.2118(5) 0.10373(19) 0.1104(13) Uani 1.000000 .
O3 O 0.1990(3) 0.1597(3) 0.05130(10) 0.0725(8) Uani 1.000000 .
O4 O -0.1699(5) -0.1003(6) 0.11930(9) 0.130(2) Uani 1.000000 .
O5 O -0.2621(3) -0.1448(3) 0.04353(9) 0.0653(7) Uani 1.000000 .
S1 S 0.01650(13) -0.37943(10) 0.10740(5) 0.0719(4) Uani 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
C1 C2 1.561(8) . ?
C1 O1 1.336(6) . ?
C1 O2 1.178(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.509(7) . ?
C2 N1 1.450(5) . ?
C3 H3a 0.9600 . ?
C3 H3b 0.9600 . ?
C3 H3c 0.9600 . ?
C4 C5 1.522(4) . ?
C4 N1 1.321(4) . ?
C4 O3 1.230(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.513(5) . ?
C5 N2 1.454(4) . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C6 C7 1.500(6) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 S1 1.802(4) . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C8 S1 1.759(7) . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
C9 O1 1.453(9) . ?
C10 N2 1.324(5) . ?
C10 O4 1.194(4) . ?
C10 O5 1.331(4) . ?
C11 C12 1.490(7) . ?
C11 C13 1.504(10) . ?
C11 C14 1.466(12) . ?
C11 O5 1.447(6) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2a 0.8600 . ?

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
O1 C1 C2 107.2(6) . . ?
O2 C1 C2 126.0(4) . . ?
O2 C1 O1 126.7(6) . . ?
H2 C2 C1 109.2(3) . . ?
C3 C2 C1 111.3(5) . . ?
C3 C2 H2 109.2(4) . . ?
N1 C2 C1 108.5(4) . . ?
N1 C2 H2 109.2(3) . . ?
N1 C2 C3 109.5(4) . . ?
H3a C3 C2 109.5 . . ?
H3b C3 C2 109.5 . . ?
H3b C3 H3a 109.5 . . ?
H3c C3 C2 109.5 . . ?
H3c C3 H3a 109.5 . . ?
H3c C3 H3b 109.5 . . ?
N1 C4 C5 116.1(3) . . ?
O3 C4 C5 121.5(3) . . ?
O3 C4 N1 122.4(3) . . ?
H5 C5 C4 108.79(15) . . ?
C6 C5 C4 107.5(3) . . ?
C6 C5 H5 108.79(16) . . ?
N2 C5 C4 111.5(3) . . ?
N2 C5 H5 108.79(15) . . ?
N2 C5 C6 111.5(2) . . ?
H6a C6 C5 108.65(16) . . ?
H6b C6 C5 108.65(17) . . ?
H6b C6 H6a 107.6 . . ?
C7 C6 C5 114.4(3) . . ?
C7 C6 H6a 108.6(2) . . ?
C7 C6 H6b 108.6(2) . . ?
H7a C7 C6 108.4(2) . . ?
H7b C7 C6 108.4(2) . . ?
H7b C7 H7a 107.5 . . ?
S1 C7 C6 115.4(3) . . ?
S1 C7 H7a 108.42(16) . . ?
S1 C7 H7b 108.42(14) . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
S1 C8 H8a 109.5 . . ?
S1 C8 H8b 109.5 . . ?
S1 C8 H8c 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
O1 C9 H9a 109.5 . . ?
O1 C9 H9b 109.5 . . ?
O1 C9 H9c 109.5 . . ?
O4 C10 N2 124.1(3) . . ?
O5 C10 N2 112.0(3) . . ?
O5 C10 O4 123.9(4) . . ?
C13 C11 C12 112.9(7) . . ?
C14 C11 C12 108.5(6) . . ?
C14 C11 C13 113.1(9) . . ?
O5 C11 C12 104.2(4) . . ?
O5 C11 C13 110.6(5) . . ?
O5 C11 C14 107.1(7) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14a C14 C11 109.5 . . ?
H14b C14 C11 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C11 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C4 N1 C2 121.1(3) . . ?
H1 N1 C2 119.5(2) . . ?
H1 N1 C4 119.47(18) . . ?
C10 N2 C5 121.9(2) . . ?
H2a N2 C5 119.05(15) . . ?
H2a N2 C10 119.05(18) . . ?
C9 O1 C1 114.3(6) . . ?
C11 O5 C10 122.9(3) . . ?
C8 S1 C7 102.5(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
C1 C2 N1 C4 -65.2(5) . . . . ?
C2 N1 C4 C5 170.4(4) . . . . ?
C2 N1 C4 O3 -6.2(5) . . . . ?
C4 C5 C6 C7 176.9(3) . . . . ?
C4 C5 N2 C10 -84.6(3) . . . . ?
C5 C6 C7 S1 -55.8(3) . . . . ?
C5 N2 C10 O4 -2.3(5) . . . . ?
C5 N2 C10 O5 178.7(3) . . . . ?
C10 O5 C11 C12 177.7(6) . . . . ?
C10 O5 C11 C13 -60.8(8) . . . . ?
C10 O5 C11 C14 62.8(6) . . . . ?


_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 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.863
_chemical_melting_point          398.2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
