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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_cu_2067_cg_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2338773'
loop_
_audit_author_name
_audit_author_address
'Christopher Golz'
;Georg August University Goettingen
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
loop_
_audit_author_email
shahilan.ratnam@uni-goettingen.de
'cgolz@gwdg.de '
djansse@gwdg.de

_audit_creation_method           
;FinalCif V123 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2023-08-09
_diffrn_source_power             0.05
_exptl_crystal_colour_primary    colourless
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.662(4)
 0.198(3) 0.140(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C18(H18), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C15(H15A,
 H15B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B),
 C24(H24A,H24B), C31(H31A,H31B)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C32(H32A,
 H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C16 H29 N3 O3'
_chemical_formula_moiety         'C16 H27 N3 O2, H2 O'
_chemical_formula_weight         311.42
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7086(15)
_cell_length_b                   9.5131(12)
_cell_length_c                   31.662(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.913(3)
_cell_angle_gamma                90
_cell_volume                     3513.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    2387
_cell_measurement_theta_min      2.803
_cell_measurement_theta_max      77.996
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'from a mixture of ethyl acetate and pentane by vapor diffusion.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          1.045
_exptl_crystal_size_mid          0.604
_exptl_crystal_size_min          0.372
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.253174
_exptl_absorpt_correction_T_max  0.445117
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1205 before and 0.0687 after correction.
 
For component 2:
 wR2(int) was 0.1787 before and 0.0736 after correction.
 
For component 3:
 wR2(int) was 0.1652 before and 0.0819 after correction.
 The Ratio of minimum to maximum transmission is 0.57.

Final HKLF 4 output contains 188191 reflections, Rint = 0.1048
 (128998 with I > 3sig(I), Rint = 0.0999)
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.547
_shelx_estimated_absorpt_T_max   0.792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.0
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            8927
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.1048
_diffrn_reflns_theta_min         2.801
_diffrn_reflns_theta_max         78.598
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       39
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8927
_reflns_number_gt                8293
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       
'Bruker BIS V6.2.15/2021-03-16 && APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          
'The material is severly multicrystalline and brittle with a tendency to break even further when attempted tu cut clean. The used relatively big scpecimen was centered on a visually well defined corer, in hope to obtain a relatively clean diffraction pattern. That was only a limited success, as there were still at least two minor domains found and used for twin indexation. There are more and more minor domains that were not possible to index but cause notable interference with the data. Presumably, this is the main cause for the modest R index.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1501P)²+0.9557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         8927
_refine_ls_number_parameters     431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2248
_refine_ls_wR_factor_gt          0.2155
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.662(4)
2 0.198(3)
3 0.140(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 -1.00 2.00 0.5110
-1.00 0.00 -1.00 0.4790
-1.00 -1.00 2.00 0.4710
-1.00 -1.00 -1.00 0.5420
-1.00 0.00 2.00 0.3470
-1.00 1.00 2.00 0.3670
0.00 0.00 1.00 0.0520
0.00 0.00 -1.00 0.1860
0.00 2.00 1.00 0.2130
0.00 -2.00 -1.00 0.3540
0.00 -1.00 1.00 0.3130
0.00 1.00 -1.00 0.2470
1.00 0.00 1.00 0.1610
1.00 1.00 -1.00 0.1230
1.00 0.00 2.00 0.1470
1.00 1.00 -2.00 0.1240
1.00 1.00 1.00 0.1290
1.00 0.00 -2.00 0.1830
1.00 -1.00 -2.00 0.1530
2.00 1.00 -2.00 0.1280
2.00 -2.00 -1.00 0.1410

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32561(12) 0.22411(13) 0.40255(5) 0.0336(3) Uani 1 1 d . . . . .
O2 O 0.44079(11) 0.38000(13) 0.37367(4) 0.0303(3) Uani 1 1 d . . . . .
N1 N 0.27685(13) 0.72553(15) 0.41580(5) 0.0263(3) Uani 1 1 d . . . . .
H1 H 0.3106(19) 0.806(3) 0.4150(7) 0.024(5) Uiso 1 1 d . . . . .
N2 N 0.14642(12) 0.58119(15) 0.44823(5) 0.0268(3) Uani 1 1 d . . . . .
N3 N 0.13352(13) 0.82185(15) 0.45317(5) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.18651(15) 0.70786(18) 0.43842(5) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.31855(14) 0.61129(17) 0.39000(6) 0.0259(4) Uani 1 1 d . . . . .
H2 H 0.403755 0.620595 0.390646 0.031 Uiso 1 1 calc R U . . .
C3 C 0.26960(16) 0.62031(18) 0.34312(6) 0.0289(4) Uani 1 1 d . . . . .
H3 H 0.304301 0.541147 0.327841 0.035 Uiso 1 1 calc R U . . .
C4 C 0.13932(17) 0.6017(2) 0.33669(6) 0.0351(4) Uani 1 1 d . . . . .
H4A H 0.101249 0.679629 0.350751 0.042 Uiso 1 1 calc R U . . .
H4B H 0.117310 0.512334 0.349800 0.042 Uiso 1 1 calc R U . . .
C5 C 0.0993(2) 0.6004(3) 0.28907(7) 0.0436(5) Uani 1 1 d . . . . .
H5A H 0.132433 0.517783 0.275543 0.052 Uiso 1 1 calc R U . . .
H5B H 0.014789 0.591963 0.285405 0.052 Uiso 1 1 calc R U . . .
C6 C 0.1359(2) 0.7338(3) 0.26744(8) 0.0518(6) Uani 1 1 d . . . . .
H6A H 0.094661 0.815121 0.278395 0.062 Uiso 1 1 calc R U . . .
H6B H 0.114314 0.726756 0.236591 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2651(2) 0.7587(3) 0.27498(7) 0.0473(5) Uani 1 1 d . . . . .
H7A H 0.306135 0.685023 0.260189 0.057 Uiso 1 1 calc R U . . .
H7B H 0.284250 0.850826 0.262896 0.057 Uiso 1 1 calc R U . . .
C8 C 0.30524(19) 0.7562(2) 0.32218(7) 0.0376(4) Uani 1 1 d . . . . .
H8A H 0.389750 0.765229 0.325755 0.045 Uiso 1 1 calc R U . . .
H8B H 0.271979 0.837446 0.336357 0.045 Uiso 1 1 calc R U . . .
C9 C 0.29290(15) 0.47143(17) 0.41040(6) 0.0259(4) Uani 1 1 d . . . . .
C10 C 0.20858(15) 0.46573(17) 0.43768(6) 0.0261(4) Uani 1 1 d . . . . .
C11 C 0.17012(15) 0.33574(18) 0.45971(6) 0.0287(4) Uani 1 1 d . . . . .
H11A H 0.100136 0.299063 0.444387 0.043 Uiso 1 1 calc R U . . .
H11B H 0.154709 0.359341 0.488806 0.043 Uiso 1 1 calc R U . . .
H11C H 0.230528 0.264287 0.460244 0.043 Uiso 1 1 calc R U . . .
C12 C 0.35149(15) 0.34704(18) 0.39645(6) 0.0272(4) Uani 1 1 d . . . . .
C13 C 0.16604(16) 0.96465(18) 0.44279(6) 0.0312(4) Uani 1 1 d . . . . .
H13A H 0.231073 0.994588 0.462256 0.047 Uiso 1 1 calc R U . . .
H13B H 0.101050 1.027942 0.445516 0.047 Uiso 1 1 calc R U . . .
H13C H 0.187899 0.967523 0.413607 0.047 Uiso 1 1 calc R U . . .
C14 C 0.05182(15) 0.80915(19) 0.48533(6) 0.0296(4) Uani 1 1 d . . . . .
H14A H -0.025793 0.827573 0.472397 0.044 Uiso 1 1 calc R U . . .
H14B H 0.070982 0.877463 0.508000 0.044 Uiso 1 1 calc R U . . .
H14C H 0.055456 0.713908 0.497157 0.044 Uiso 1 1 calc R U . . .
C15 C 0.49323(17) 0.26431(19) 0.35291(6) 0.0319(4) Uani 1 1 d . . . . .
H15A H 0.435158 0.214388 0.333899 0.038 Uiso 1 1 calc R U . . .
H15B H 0.527108 0.196745 0.374225 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5850(2) 0.3246(2) 0.32775(7) 0.0428(5) Uani 1 1 d . . . . .
H16A H 0.550676 0.392146 0.307018 0.064 Uiso 1 1 calc R U . . .
H16B H 0.621567 0.248638 0.312913 0.064 Uiso 1 1 calc R U . . .
H16C H 0.642681 0.372319 0.346947 0.064 Uiso 1 1 calc R U . . .
O3 O 0.42080(12) -0.04286(14) 0.41003(6) 0.0434(4) Uani 1 1 d . . . . .
H3A H 0.491(4) -0.037(4) 0.4241(13) 0.077(11) Uiso 1 1 d . . . . .
H3B H 0.401(3) 0.044(4) 0.4081(11) 0.062(9) Uiso 1 1 d . . . . .
O4 O 0.88027(15) 0.26330(16) 0.40140(6) 0.0445(4) Uani 1 1 d . . . . .
O5 O 0.96077(11) 0.09193(14) 0.36588(4) 0.0322(3) Uani 1 1 d . . . . .
N4 N 0.65132(13) -0.05110(16) 0.44375(5) 0.0287(3) Uani 1 1 d . . . . .
N5 N 0.77741(13) -0.21931(15) 0.41884(5) 0.0272(3) Uani 1 1 d . . . . .
H5 H 0.807(2) -0.305(3) 0.4219(8) 0.032(6) Uiso 1 1 d . . . . .
N6 N 0.62408(13) -0.28763(16) 0.45573(5) 0.0302(3) Uani 1 1 d . . . . .
C17 C 0.68558(15) -0.18442(19) 0.43897(5) 0.0271(4) Uani 1 1 d . . . . .
C18 C 0.82619(15) -0.12064(18) 0.38955(6) 0.0274(4) Uani 1 1 d . . . . .
H18 H 0.910555 -0.138628 0.390761 0.033 Uiso 1 1 calc R U . . .
C19 C 0.77624(15) -0.14484(18) 0.34322(6) 0.0294(4) Uani 1 1 d . . . . .
H19 H 0.818598 -0.081348 0.324813 0.035 Uiso 1 1 calc R U . . .
C20 C 0.64835(16) -0.1089(2) 0.33536(6) 0.0329(4) Uani 1 1 d . . . . .
H20A H 0.603625 -0.170069 0.353129 0.039 Uiso 1 1 calc R U . . .
H20B H 0.635839 -0.010105 0.343665 0.039 Uiso 1 1 calc R U . . .
C21 C 0.6061(2) -0.1291(2) 0.28856(7) 0.0419(5) Uani 1 1 d . . . . .
H21A H 0.522889 -0.109202 0.284528 0.050 Uiso 1 1 calc R U . . .
H21B H 0.645920 -0.061821 0.271004 0.050 Uiso 1 1 calc R U . . .
C22 C 0.6285(2) -0.2784(3) 0.27412(7) 0.0495(6) Uani 1 1 d . . . . .
H22A H 0.605292 -0.286946 0.243417 0.059 Uiso 1 1 calc R U . . .
H22B H 0.581571 -0.344800 0.289366 0.059 Uiso 1 1 calc R U . . .
C23 C 0.7548(2) -0.3172(3) 0.28248(8) 0.0494(6) Uani 1 1 d . . . . .
H23A H 0.800841 -0.258271 0.264539 0.059 Uiso 1 1 calc R U . . .
H23B H 0.765627 -0.416692 0.274588 0.059 Uiso 1 1 calc R U . . .
C24 C 0.79730(19) -0.2961(2) 0.32908(7) 0.0386(5) Uani 1 1 d . . . . .
H24A H 0.880323 -0.317130 0.333119 0.046 Uiso 1 1 calc R U . . .
H24B H 0.756916 -0.362099 0.346844 0.046 Uiso 1 1 calc R U . . .
C25 C 0.80935(15) 0.02774(18) 0.40542(6) 0.0275(4) Uani 1 1 d . . . . .
C26 C 0.72130(15) 0.05263(18) 0.43039(6) 0.0284(4) Uani 1 1 d . . . . .
C27 C 0.68831(17) 0.19614(19) 0.44569(7) 0.0344(4) Uani 1 1 d . . . . .
H27A H 0.736386 0.220009 0.471563 0.052 Uiso 1 1 calc R U . . .
H27B H 0.607601 0.195394 0.451718 0.052 Uiso 1 1 calc R U . . .
H27C H 0.699541 0.266172 0.423726 0.052 Uiso 1 1 calc R U . . .
C28 C 0.88291(16) 0.13969(19) 0.39181(6) 0.0305(4) Uani 1 1 d . . . . .
C29 C 0.54342(16) -0.2584(2) 0.48729(6) 0.0346(4) Uani 1 1 d . . . . .
H29A H 0.547222 -0.158465 0.494840 0.052 Uiso 1 1 calc R U . . .
H29B H 0.563323 -0.315279 0.512660 0.052 Uiso 1 1 calc R U . . .
H29C H 0.465538 -0.281698 0.475579 0.052 Uiso 1 1 calc R U . . .
C30 C 0.64103(16) -0.43607(19) 0.44668(7) 0.0337(4) Uani 1 1 d . . . . .
H30A H 0.667316 -0.446093 0.418271 0.051 Uiso 1 1 calc R U . . .
H30B H 0.568481 -0.486578 0.448016 0.051 Uiso 1 1 calc R U . . .
H30C H 0.698699 -0.475330 0.467679 0.051 Uiso 1 1 calc R U . . .
C31 C 1.03649(17) 0.1981(2) 0.35065(6) 0.0354(4) Uani 1 1 d . . . . .
H31A H 1.083513 0.240885 0.374775 0.042 Uiso 1 1 calc R U . . .
H31B H 0.991058 0.273228 0.335517 0.042 Uiso 1 1 calc R U . . .
C32 C 1.11236(19) 0.1273(2) 0.32116(7) 0.0421(5) Uani 1 1 d . . . . .
H32A H 1.064925 0.084142 0.297639 0.063 Uiso 1 1 calc R U . . .
H32B H 1.158084 0.054492 0.336607 0.063 Uiso 1 1 calc R U . . .
H32C H 1.163542 0.196980 0.309987 0.063 Uiso 1 1 calc R U . . .
O6 O 0.90887(13) -0.46153(15) 0.43260(6) 0.0427(4) Uani 1 1 d . . . . .
H6C H 0.991(3) -0.448(4) 0.4384(11) 0.066(9) Uiso 1 1 d . . . . .
H6D H 0.904(3) -0.541(4) 0.4212(11) 0.055(8) Uiso 1 1 d . . . . .


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
O1 C12 1.228(2) . ?
O2 C12 1.357(2) . ?
O2 C15 1.445(2) . ?
N1 H1 0.86(2) . ?
N1 C1 1.338(2) . ?
N1 C2 1.468(2) . ?
N2 C1 1.339(2) . ?
N2 C10 1.374(2) . ?
N3 C1 1.352(2) . ?
N3 C13 1.456(2) . ?
N3 C14 1.461(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.547(2) . ?
C2 C9 1.520(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.532(3) . ?
C3 C8 1.527(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.540(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.521(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.529(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.528(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.367(2) . ?
C9 C12 1.455(2) . ?
C10 C11 1.507(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.505(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O3 H3A 0.90(4) . ?
O3 H3B 0.86(4) . ?
O4 C28 1.216(2) . ?
O5 C28 1.356(2) . ?
O5 C31 1.453(2) . ?
N4 C17 1.343(2) . ?
N4 C26 1.372(2) . ?
N5 H5 0.88(3) . ?
N5 C17 1.338(2) . ?
N5 C18 1.469(2) . ?
N6 C17 1.353(2) . ?
N6 C29 1.459(2) . ?
N6 C30 1.458(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.549(2) . ?
C18 C25 1.517(2) . ?
C19 H19 1.0000 . ?
C19 C20 1.535(3) . ?
C19 C24 1.533(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.534(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.522(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.525(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.529(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.372(3) . ?
C25 C28 1.458(2) . ?
C26 C27 1.510(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.502(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O6 H6C 0.98(4) . ?
O6 H6D 0.84(4) . ?

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
C12 O2 C15 116.26(14) . . ?
C1 N1 H1 120.9(15) . . ?
C1 N1 C2 121.38(14) . . ?
C2 N1 H1 117.7(15) . . ?
C1 N2 C10 117.34(15) . . ?
C1 N3 C13 122.25(15) . . ?
C1 N3 C14 121.45(14) . . ?
C13 N3 C14 115.73(14) . . ?
N1 C1 N2 123.10(15) . . ?
N1 C1 N3 119.42(15) . . ?
N2 C1 N3 117.46(15) . . ?
N1 C2 H2 107.6 . . ?
N1 C2 C3 112.29(14) . . ?
N1 C2 C9 108.92(14) . . ?
C3 C2 H2 107.6 . . ?
C9 C2 H2 107.6 . . ?
C9 C2 C3 112.69(14) . . ?
C2 C3 H3 106.9 . . ?
C4 C3 C2 113.83(15) . . ?
C4 C3 H3 106.9 . . ?
C8 C3 C2 111.77(15) . . ?
C8 C3 H3 106.9 . . ?
C8 C3 C4 110.24(16) . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C3 C4 C5 110.29(17) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.13(19) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.80(19) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.6(2) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C3 C8 C7 111.40(18) . . ?
C3 C8 H8A 109.3 . . ?
C3 C8 H8B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C2 118.86(15) . . ?
C10 C9 C12 122.97(15) . . ?
C12 C9 C2 117.86(15) . . ?
N2 C10 C11 110.97(15) . . ?
C9 C10 N2 123.21(15) . . ?
C9 C10 C11 125.82(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 O2 121.04(16) . . ?
O1 C12 C9 126.70(17) . . ?
O2 C12 C9 112.22(15) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 110.2 . . ?
O2 C15 H15B 110.2 . . ?
O2 C15 C16 107.51(15) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H3A O3 H3B 102(3) . . ?
C28 O5 C31 115.40(15) . . ?
C17 N4 C26 116.90(15) . . ?
C17 N5 H5 119.6(16) . . ?
C17 N5 C18 120.93(15) . . ?
C18 N5 H5 119.3(16) . . ?
C17 N6 C29 121.85(15) . . ?
C17 N6 C30 122.69(16) . . ?
C30 N6 C29 115.23(15) . . ?
N4 C17 N6 117.86(16) . . ?
N5 C17 N4 123.23(16) . . ?
N5 C17 N6 118.91(16) . . ?
N5 C18 H18 107.6 . . ?
N5 C18 C19 111.54(14) . . ?
N5 C18 C25 108.47(14) . . ?
C19 C18 H18 107.6 . . ?
C25 C18 H18 107.6 . . ?
C25 C18 C19 113.75(14) . . ?
C18 C19 H19 107.2 . . ?
C20 C19 C18 113.85(15) . . ?
C20 C19 H19 107.2 . . ?
C24 C19 C18 111.04(15) . . ?
C24 C19 H19 107.2 . . ?
C24 C19 C20 109.92(15) . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 C19 110.99(17) . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 C20 110.96(18) . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C21 C22 C23 111.31(19) . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C22 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
C22 C23 C24 111.50(19) . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C19 C24 H24A 109.4 . . ?
C19 C24 H24B 109.4 . . ?
C23 C24 C19 110.97(18) . . ?
C23 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 C18 118.47(16) . . ?
C26 C25 C28 122.42(16) . . ?
C28 C25 C18 119.02(15) . . ?
N4 C26 C27 112.04(16) . . ?
C25 C26 N4 123.46(16) . . ?
C25 C26 C27 124.49(17) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O4 C28 O5 120.54(18) . . ?
O4 C28 C25 127.20(18) . . ?
O5 C28 C25 112.26(15) . . ?
N6 C29 H29A 109.5 . . ?
N6 C29 H29B 109.5 . . ?
N6 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N6 C30 H30A 109.5 . . ?
N6 C30 H30B 109.5 . . ?
N6 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O5 C31 H31A 110.2 . . ?
O5 C31 H31B 110.2 . . ?
O5 C31 C32 107.74(16) . . ?
H31A C31 H31B 108.5 . . ?
C32 C31 H31A 110.2 . . ?
C32 C31 H31B 110.2 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
H6C O6 H6D 103(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.86(2) 1.95(2) 2.790(2) 165(2) 1_565 yes
C11 H11C O1 0.98 2.25 2.878(2) 120.6 . yes
O3 H3A N4 0.90(4) 1.93(4) 2.817(2) 167(4) . yes
O3 H3B O1 0.86(4) 1.93(4) 2.7755(19) 169(3) . yes
N5 H5 O6 0.88(3) 1.93(3) 2.785(2) 164(2) . yes
O6 H6C N2 0.98(4) 1.84(4) 2.813(2) 179(3) 1_645 yes
O6 H6D O4 0.84(4) 1.97(4) 2.808(2) 172(3) 1_545 yes

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
N1 C2 C3 C4 -64.17(19) . . . . ?
N1 C2 C3 C8 61.54(19) . . . . ?
N1 C2 C9 C10 21.4(2) . . . . ?
N1 C2 C9 C12 -164.83(15) . . . . ?
C1 N1 C2 C3 95.67(19) . . . . ?
C1 N1 C2 C9 -29.9(2) . . . . ?
C1 N2 C10 C9 -14.3(3) . . . . ?
C1 N2 C10 C11 166.21(15) . . . . ?
C2 N1 C1 N2 17.7(3) . . . . ?
C2 N1 C1 N3 -163.86(16) . . . . ?
C2 C3 C4 C5 -175.52(16) . . . . ?
C2 C3 C8 C7 175.21(17) . . . . ?
C2 C9 C10 N2 -1.0(3) . . . . ?
C2 C9 C10 C11 178.34(16) . . . . ?
C2 C9 C12 O1 -164.14(18) . . . . ?
C2 C9 C12 O2 14.0(2) . . . . ?
C3 C2 C9 C10 -103.88(18) . . . . ?
C3 C2 C9 C12 69.9(2) . . . . ?
C3 C4 C5 C6 -57.0(2) . . . . ?
C4 C3 C8 C7 -57.1(2) . . . . ?
C4 C5 C6 C7 54.6(3) . . . . ?
C5 C6 C7 C8 -53.4(3) . . . . ?
C6 C7 C8 C3 54.7(3) . . . . ?
C8 C3 C4 C5 58.0(2) . . . . ?
C9 C2 C3 C4 59.28(19) . . . . ?
C9 C2 C3 C8 -175.01(15) . . . . ?
C10 N2 C1 N1 6.2(3) . . . . ?
C10 N2 C1 N3 -172.29(15) . . . . ?
C10 C9 C12 O1 9.3(3) . . . . ?
C10 C9 C12 O2 -172.54(16) . . . . ?
C12 O2 C15 C16 176.95(16) . . . . ?
C12 C9 C10 N2 -174.44(16) . . . . ?
C12 C9 C10 C11 4.9(3) . . . . ?
C13 N3 C1 N1 4.5(3) . . . . ?
C13 N3 C1 N2 -176.92(16) . . . . ?
C14 N3 C1 N1 -166.44(16) . . . . ?
C14 N3 C1 N2 12.1(2) . . . . ?
C15 O2 C12 O1 7.5(2) . . . . ?
C15 O2 C12 C9 -170.76(15) . . . . ?
N5 C18 C19 C20 67.16(19) . . . . ?
N5 C18 C19 C24 -57.53(19) . . . . ?
N5 C18 C25 C26 -24.9(2) . . . . ?
N5 C18 C25 C28 158.39(16) . . . . ?
C17 N4 C26 C25 13.4(3) . . . . ?
C17 N4 C26 C27 -167.67(16) . . . . ?
C17 N5 C18 C19 -93.28(19) . . . . ?
C17 N5 C18 C25 32.8(2) . . . . ?
C18 N5 C17 N4 -19.1(3) . . . . ?
C18 N5 C17 N6 161.44(16) . . . . ?
C18 C19 C20 C21 177.50(15) . . . . ?
C18 C19 C24 C23 -176.38(17) . . . . ?
C18 C25 C26 N4 3.7(3) . . . . ?
C18 C25 C26 C27 -175.06(17) . . . . ?
C18 C25 C28 O4 179.7(2) . . . . ?
C18 C25 C28 O5 -0.7(2) . . . . ?
C19 C18 C25 C26 99.86(19) . . . . ?
C19 C18 C25 C28 -76.9(2) . . . . ?
C19 C20 C21 C22 56.7(2) . . . . ?
C20 C19 C24 C23 56.7(2) . . . . ?
C20 C21 C22 C23 -55.3(3) . . . . ?
C21 C22 C23 C24 55.2(3) . . . . ?
C22 C23 C24 C19 -56.0(3) . . . . ?
C24 C19 C20 C21 -57.2(2) . . . . ?
C25 C18 C19 C20 -55.9(2) . . . . ?
C25 C18 C19 C24 179.39(15) . . . . ?
C26 N4 C17 N5 -6.0(3) . . . . ?
C26 N4 C17 N6 173.52(16) . . . . ?
C26 C25 C28 O4 3.1(3) . . . . ?
C26 C25 C28 O5 -177.29(16) . . . . ?
C28 O5 C31 C32 -177.51(16) . . . . ?
C28 C25 C26 N4 -179.67(17) . . . . ?
C28 C25 C26 C27 1.5(3) . . . . ?
C29 N6 C17 N4 -16.3(3) . . . . ?
C29 N6 C17 N5 163.27(17) . . . . ?
C30 N6 C17 N4 169.57(16) . . . . ?
C30 N6 C17 N5 -10.9(3) . . . . ?
C31 O5 C28 O4 -0.9(3) . . . . ?
C31 O5 C28 C25 179.39(15) . . . . ?

####################################################################### 
# 
# 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_2234_pna21
_database_code_depnum_ccdc_archive 'CCDC 2338775'
loop_
_audit_author_name
_audit_author_address
'Christopher Golz'
;Georg August University Goettingen
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
loop_
_audit_author_email
djansse@gwdg.de
'cgolz@gwdg.de '

_audit_creation_method           
;FinalCif V134 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2024-02-13
_diffrn_source_power             0.05
_exptl_crystal_colour_primary    colourless
_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. Restrained distances
 N1'-H1' = N1-H1
 0.88 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C3'(H3'), C4'(H4')
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C15(H15A,
 H15B), C5'(H5'A,H5'B), C6'(H6'A,H6'B), C7'(H7'A,H7'B), C8'(H8'A,H8'B),
 C9'(H9'A,H9'B), C15'(H15C,H15D)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C13'(H13'), C14'(H14')
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C11'(H11D,H11E,H11F), C16'(H16D,
 H16E,H16F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C16 H23 N3 O2'
_chemical_formula_moiety         'C16 H23 N3 O2'
_chemical_formula_weight         289.37
_chemical_melting_point          ?
_chemical_absolute_configuration unk
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   18.2950(5)
_cell_length_b                   10.1722(3)
_cell_length_c                   16.2289(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3020.21(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.363
_cell_measurement_theta_max      27.838
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'from a mixture of ethyl acetate and pentane.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8155
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1313 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.8155.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.991
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.0
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            55755
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         27.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7221
_reflns_number_gt                6352
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS V6.2.15/2021-03-16 and APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0727P)²+1.5480P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         7221
_refine_ls_number_parameters     389
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_abs_structure_details 
;
 Flack x determined using 2726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -2.00 0.00 0.1240
2.00 -1.00 0.00 0.1510
-1.00 -1.00 0.00 0.0360
1.00 -1.00 -1.00 0.1300
2.00 -1.00 -2.00 0.1300
-1.00 -1.00 2.00 0.0530
2.00 -1.00 2.00 0.1330
2.00 0.00 -1.00 0.1260
-2.00 0.00 1.00 0.1260
0.00 0.00 -1.00 0.0330
0.00 0.00 1.00 0.0510
2.00 1.00 0.00 0.0790
1.00 1.00 0.00 0.0960
-1.00 1.00 1.00 0.1060
-2.00 1.00 2.00 0.1060
1.00 1.00 -2.00 0.0700
-2.00 1.00 -2.00 0.0960
2.00 1.00 1.00 0.0840
-2.00 1.00 -1.00 0.1030
-1.00 2.00 0.00 0.1190
-2.00 2.00 1.00 0.1130
-1.00 2.00 2.00 0.0980

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.72003(13) 0.7217(2) 0.42973(16) 0.0232(5) Uani 1 1 d . . . . .
O2 O 0.69294(14) 0.5592(2) 0.34052(17) 0.0269(6) Uani 1 1 d . . . . .
N1 N 0.48104(16) 0.5613(3) 0.44851(18) 0.0186(6) Uani 1 1 d D . . . .
H1 H 0.4466(18) 0.506(3) 0.443(3) 0.022 Uiso 1 1 d D U . . .
N2 N 0.42211(15) 0.6195(3) 0.57629(16) 0.0166(5) Uani 1 1 d . . . . .
N3 N 0.52656(15) 0.7177(2) 0.54210(16) 0.0146(5) Uani 1 1 d . . . . .
C1 C 0.67271(18) 0.6381(3) 0.3920(2) 0.0190(6) Uani 1 1 d . . . . .
C2 C 0.59890(17) 0.6526(3) 0.42478(19) 0.0155(6) Uani 1 1 d . . . . .
C3 C 0.58329(16) 0.7639(3) 0.48535(18) 0.0141(6) Uani 1 1 d . . . . .
H3 H 0.628741 0.781426 0.517772 0.017 Uiso 1 1 calc R U . . .
C4 C 0.55794(17) 0.8949(3) 0.44538(19) 0.0134(6) Uani 1 1 d . . . . .
H4 H 0.549873 0.958679 0.491369 0.016 Uiso 1 1 calc R U . . .
C5 C 0.61596(16) 0.9551(3) 0.3890(2) 0.0159(6) Uani 1 1 d . . . . .
H5A H 0.625648 0.895009 0.342261 0.019 Uiso 1 1 calc R U . . .
H5B H 0.662098 0.966753 0.420032 0.019 Uiso 1 1 calc R U . . .
C6 C 0.58991(17) 1.0885(3) 0.35617(19) 0.0173(6) Uani 1 1 d . . . . .
H6A H 0.584446 1.150607 0.402722 0.021 Uiso 1 1 calc R U . . .
H6B H 0.627134 1.124585 0.318121 0.021 Uiso 1 1 calc R U . . .
C7 C 0.51727(18) 1.0762(3) 0.3111(2) 0.0187(6) Uani 1 1 d . . . . .
H7A H 0.500584 1.164632 0.293817 0.022 Uiso 1 1 calc R U . . .
H7B H 0.524104 1.022395 0.260845 0.022 Uiso 1 1 calc R U . . .
C8 C 0.45934(17) 1.0134(3) 0.3651(2) 0.0192(6) Uani 1 1 d . . . . .
H8A H 0.414363 0.999388 0.332317 0.023 Uiso 1 1 calc R U . . .
H8B H 0.447283 1.073512 0.411081 0.023 Uiso 1 1 calc R U . . .
C9 C 0.48532(17) 0.8818(3) 0.3999(2) 0.0181(6) Uani 1 1 d . . . . .
H9A H 0.447908 0.847128 0.438272 0.022 Uiso 1 1 calc R U . . .
H9B H 0.490888 0.817972 0.354305 0.022 Uiso 1 1 calc R U . . .
C10 C 0.54567(18) 0.5627(3) 0.4058(2) 0.0158(6) Uani 1 1 d . . . . .
C11 C 0.5499(2) 0.4580(3) 0.3407(2) 0.0233(7) Uani 1 1 d . . . . .
H11A H 0.582598 0.387612 0.359303 0.035 Uiso 1 1 calc R U . . .
H11B H 0.568957 0.496165 0.289604 0.035 Uiso 1 1 calc R U . . .
H11C H 0.501053 0.421937 0.330831 0.035 Uiso 1 1 calc R U . . .
C12 C 0.47493(17) 0.6306(3) 0.52118(19) 0.0154(6) Uani 1 1 d . . . . .
C13 C 0.44221(18) 0.7088(3) 0.6371(2) 0.0180(7) Uani 1 1 d . . . . .
H13 H 0.415131 0.724450 0.686082 0.022 Uiso 1 1 calc R U . . .
C14 C 0.50553(17) 0.7706(3) 0.61736(19) 0.0166(6) Uani 1 1 d . . . . .
H14 H 0.530229 0.836201 0.648389 0.020 Uiso 1 1 calc R U . . .
C15 C 0.79666(19) 0.7108(4) 0.4071(2) 0.0255(7) Uani 1 1 d . . . . .
H15A H 0.809169 0.617038 0.398638 0.031 Uiso 1 1 calc R U . . .
H15B H 0.827336 0.744793 0.452569 0.031 Uiso 1 1 calc R U . . .
C16 C 0.8131(2) 0.7864(4) 0.3296(3) 0.0307(8) Uani 1 1 d . . . . .
H16A H 0.784195 0.750579 0.284004 0.046 Uiso 1 1 calc R U . . .
H16B H 0.865223 0.778812 0.316669 0.046 Uiso 1 1 calc R U . . .
H16C H 0.800508 0.879170 0.337757 0.046 Uiso 1 1 calc R U . . .
O1' O 0.06486(12) 0.2751(2) 0.56620(14) 0.0201(5) Uani 1 1 d . . . . .
O2' O 0.09075(14) 0.4328(2) 0.65883(16) 0.0243(5) Uani 1 1 d . . . . .
N1' N 0.30300(15) 0.4396(3) 0.54951(17) 0.0177(5) Uani 1 1 d D . . . .
H1' H 0.3381(17) 0.493(3) 0.566(2) 0.021 Uiso 1 1 d D U . . .
N2' N 0.36339(15) 0.3809(3) 0.42292(17) 0.0186(5) Uani 1 1 d . . . . .
N3' N 0.25935(14) 0.2807(2) 0.45587(16) 0.0151(5) Uani 1 1 d . . . . .
C1' C 0.11145(18) 0.3581(3) 0.60536(19) 0.0171(6) Uani 1 1 d . . . . .
C2' C 0.18574(17) 0.3463(3) 0.5723(2) 0.0149(6) Uani 1 1 d . . . . .
C3' C 0.20225(16) 0.2341(3) 0.51219(19) 0.0150(6) Uani 1 1 d . . . . .
H3' H 0.157143 0.215944 0.479301 0.018 Uiso 1 1 calc R U . . .
C4' C 0.22752(17) 0.1039(3) 0.55261(19) 0.0155(6) Uani 1 1 d . . . . .
H4' H 0.237512 0.040514 0.506858 0.019 Uiso 1 1 calc R U . . .
C5' C 0.16816(18) 0.0420(3) 0.6068(2) 0.0184(7) Uani 1 1 d . . . . .
H5'A H 0.156682 0.101771 0.653158 0.022 Uiso 1 1 calc R U . . .
H5'B H 0.123062 0.029613 0.573958 0.022 Uiso 1 1 calc R U . . .
C6' C 0.1937(2) -0.0904(3) 0.6404(2) 0.0226(7) Uani 1 1 d . . . . .
H6'A H 0.155540 -0.126674 0.677248 0.027 Uiso 1 1 calc R U . . .
H6'B H 0.200297 -0.152562 0.594055 0.027 Uiso 1 1 calc R U . . .
C7' C 0.2651(2) -0.0788(3) 0.6878(2) 0.0232(7) Uani 1 1 d . . . . .
H7'A H 0.256919 -0.026706 0.738521 0.028 Uiso 1 1 calc R U . . .
H7'B H 0.281782 -0.167565 0.704458 0.028 Uiso 1 1 calc R U . . .
C8' C 0.32371(19) -0.0138(3) 0.6365(2) 0.0246(7) Uani 1 1 d . . . . .
H8'A H 0.337381 -0.072942 0.590567 0.030 Uiso 1 1 calc R U . . .
H8'B H 0.367690 0.000247 0.670915 0.030 Uiso 1 1 calc R U . . .
C9' C 0.29853(18) 0.1186(3) 0.6012(2) 0.0205(7) Uani 1 1 d . . . . .
H9'A H 0.291032 0.181782 0.646804 0.025 Uiso 1 1 calc R U . . .
H9'B H 0.337033 0.154278 0.564604 0.025 Uiso 1 1 calc R U . . .
C10' C 0.23798(18) 0.4377(3) 0.59169(19) 0.0161(6) Uani 1 1 d . . . . .
C11' C 0.23230(19) 0.5413(3) 0.6575(2) 0.0195(6) Uani 1 1 d . . . . .
H11D H 0.276702 0.595149 0.657420 0.029 Uiso 1 1 calc R U . . .
H11E H 0.226717 0.498955 0.711395 0.029 Uiso 1 1 calc R U . . .
H11F H 0.189763 0.597191 0.646610 0.029 Uiso 1 1 calc R U . . .
C12' C 0.31051(17) 0.3698(3) 0.47768(19) 0.0165(6) Uani 1 1 d . . . . .
C13' C 0.34458(18) 0.2902(3) 0.3627(2) 0.0188(6) Uani 1 1 d . . . . .
H13' H 0.372607 0.274237 0.314474 0.023 Uiso 1 1 calc R U . . .
C14' C 0.28142(18) 0.2270(3) 0.38105(19) 0.0173(7) Uani 1 1 d . . . . .
H14' H 0.257539 0.160736 0.349776 0.021 Uiso 1 1 calc R U . . .
C15' C -0.01101(18) 0.2796(4) 0.5925(2) 0.0249(7) Uani 1 1 d . . . . .
H15C H -0.042722 0.248532 0.547061 0.030 Uiso 1 1 calc R U . . .
H15D H -0.024618 0.371634 0.605108 0.030 Uiso 1 1 calc R U . . .
C16' C -0.0236(2) 0.1958(4) 0.6673(2) 0.0304(8) Uani 1 1 d . . . . .
H16D H -0.010065 0.104643 0.654989 0.046 Uiso 1 1 calc R U . . .
H16E H -0.075296 0.199567 0.682853 0.046 Uiso 1 1 calc R U . . .
H16F H 0.006442 0.228380 0.712975 0.046 Uiso 1 1 calc R U . . .


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
O1 C1 1.359(4) . ?
O1 C15 1.454(4) . ?
O2 C1 1.216(4) . ?
N1 H1 0.85(2) . ?
N1 C10 1.370(4) . ?
N1 C12 1.379(4) . ?
N2 C12 1.322(4) . ?
N2 C13 1.391(4) . ?
N3 C3 1.465(4) . ?
N3 C12 1.339(4) . ?
N3 C14 1.389(4) . ?
C1 C2 1.459(4) . ?
C2 C3 1.527(4) . ?
C2 C10 1.371(5) . ?
C3 H3 1.0000 . ?
C3 C4 1.553(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.529(4) . ?
C4 C9 1.525(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.534(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.522(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.517(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.529(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.502(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.357(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.504(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O1' C1' 1.358(4) . ?
O1' C15' 1.453(4) . ?
O2' C1' 1.214(4) . ?
N1' H1' 0.89(2) . ?
N1' C10' 1.372(4) . ?
N1' C12' 1.372(4) . ?
N2' C12' 1.318(4) . ?
N2' C13' 1.387(4) . ?
N3' C3' 1.467(4) . ?
N3' C12' 1.350(4) . ?
N3' C14' 1.391(4) . ?
C1' C2' 1.466(4) . ?
C2' C3' 1.532(4) . ?
C2' C10' 1.370(4) . ?
C3' H3' 1.0000 . ?
C3' C4' 1.549(4) . ?
C4' H4' 1.0000 . ?
C4' C5' 1.532(5) . ?
C4' C9' 1.527(4) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C5' C6' 1.527(4) . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C6' C7' 1.522(5) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C7' C8' 1.510(5) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C8' C9' 1.534(4) . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C10' C11' 1.504(4) . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C13' H13' 0.9500 . ?
C13' C14' 1.355(5) . ?
C14' H14' 0.9500 . ?
C15' H15C 0.9900 . ?
C15' H15D 0.9900 . ?
C15' C16' 1.502(5) . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 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
C1 O1 C15 116.9(3) . . ?
C10 N1 H1 126(3) . . ?
C10 N1 C12 119.8(3) . . ?
C12 N1 H1 112(3) . . ?
C12 N2 C13 103.3(2) . . ?
C12 N3 C3 123.6(3) . . ?
C12 N3 C14 106.5(3) . . ?
C14 N3 C3 128.6(3) . . ?
O1 C1 C2 111.2(3) . . ?
O2 C1 O1 121.9(3) . . ?
O2 C1 C2 126.8(3) . . ?
C1 C2 C3 118.9(3) . . ?
C10 C2 C1 120.5(3) . . ?
C10 C2 C3 120.4(3) . . ?
N3 C3 C2 107.4(2) . . ?
N3 C3 H3 108.4 . . ?
N3 C3 C4 109.0(2) . . ?
C2 C3 H3 108.4 . . ?
C2 C3 C4 115.0(2) . . ?
C4 C3 H3 108.4 . . ?
C3 C4 H4 106.8 . . ?
C5 C4 C3 112.7(2) . . ?
C5 C4 H4 106.8 . . ?
C9 C4 C3 112.8(2) . . ?
C9 C4 H4 106.8 . . ?
C9 C4 C5 110.5(3) . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 C6 110.3(2) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.5(3) . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.5(3) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C9 111.4(3) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C4 C9 C8 111.9(3) . . ?
C4 C9 H9A 109.2 . . ?
C4 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N1 C10 C2 120.4(3) . . ?
N1 C10 C11 113.1(3) . . ?
C2 C10 C11 126.4(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 N1 126.5(3) . . ?
N2 C12 N3 113.6(3) . . ?
N3 C12 N1 119.9(3) . . ?
N2 C13 H13 124.4 . . ?
C14 C13 N2 111.2(3) . . ?
C14 C13 H13 124.4 . . ?
N3 C14 H14 127.3 . . ?
C13 C14 N3 105.3(3) . . ?
C13 C14 H14 127.3 . . ?
O1 C15 H15A 109.3 . . ?
O1 C15 H15B 109.3 . . ?
O1 C15 C16 111.4(3) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1' O1' C15' 116.3(3) . . ?
C10' N1' H1' 119(3) . . ?
C12' N1' H1' 121(3) . . ?
C12' N1' C10' 120.2(3) . . ?
C12' N2' C13' 103.6(3) . . ?
C12' N3' C3' 123.2(3) . . ?
C12' N3' C14' 106.9(3) . . ?
C14' N3' C3' 128.6(3) . . ?
O1' C1' C2' 111.1(3) . . ?
O2' C1' O1' 121.9(3) . . ?
O2' C1' C2' 127.0(3) . . ?
C1' C2' C3' 118.5(3) . . ?
C10' C2' C1' 120.5(3) . . ?
C10' C2' C3' 121.0(3) . . ?
N3' C3' C2' 107.2(2) . . ?
N3' C3' H3' 108.3 . . ?
N3' C3' C4' 109.1(2) . . ?
C2' C3' H3' 108.3 . . ?
C2' C3' C4' 115.2(3) . . ?
C4' C3' H3' 108.3 . . ?
C3' C4' H4' 106.9 . . ?
C5' C4' C3' 112.5(3) . . ?
C5' C4' H4' 106.9 . . ?
C9' C4' C3' 112.9(3) . . ?
C9' C4' H4' 106.9 . . ?
C9' C4' C5' 110.3(3) . . ?
C4' C5' H5'A 109.5 . . ?
C4' C5' H5'B 109.5 . . ?
H5'A C5' H5'B 108.1 . . ?
C6' C5' C4' 110.5(3) . . ?
C6' C5' H5'A 109.5 . . ?
C6' C5' H5'B 109.5 . . ?
C5' C6' H6'A 109.2 . . ?
C5' C6' H6'B 109.2 . . ?
H6'A C6' H6'B 107.9 . . ?
C7' C6' C5' 112.0(3) . . ?
C7' C6' H6'A 109.2 . . ?
C7' C6' H6'B 109.2 . . ?
C6' C7' H7'A 109.4 . . ?
C6' C7' H7'B 109.4 . . ?
H7'A C7' H7'B 108.0 . . ?
C8' C7' C6' 111.4(3) . . ?
C8' C7' H7'A 109.4 . . ?
C8' C7' H7'B 109.4 . . ?
C7' C8' H8'A 109.2 . . ?
C7' C8' H8'B 109.2 . . ?
C7' C8' C9' 112.2(3) . . ?
H8'A C8' H8'B 107.9 . . ?
C9' C8' H8'A 109.2 . . ?
C9' C8' H8'B 109.2 . . ?
C4' C9' C8' 111.2(3) . . ?
C4' C9' H9'A 109.4 . . ?
C4' C9' H9'B 109.4 . . ?
C8' C9' H9'A 109.4 . . ?
C8' C9' H9'B 109.4 . . ?
H9'A C9' H9'B 108.0 . . ?
N1' C10' C11' 113.9(3) . . ?
C2' C10' N1' 120.0(3) . . ?
C2' C10' C11' 126.2(3) . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
N2' C12' N1' 127.0(3) . . ?
N2' C12' N3' 112.9(3) . . ?
N3' C12' N1' 120.0(3) . . ?
N2' C13' H13' 124.1 . . ?
C14' C13' N2' 111.9(3) . . ?
C14' C13' H13' 124.1 . . ?
N3' C14' H14' 127.7 . . ?
C13' C14' N3' 104.6(3) . . ?
C13' C14' H14' 127.7 . . ?
O1' C15' H15C 109.3 . . ?
O1' C15' H15D 109.3 . . ?
O1' C15' C16' 111.4(3) . . ?
H15C C15' H15D 108.0 . . ?
C16' C15' H15C 109.3 . . ?
C16' C15' H15D 109.3 . . ?
C15' C16' H16D 109.5 . . ?
C15' C16' H16E 109.5 . . ?
C15' C16' H16F 109.5 . . ?
H16D C16' H16E 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N2' 0.85(2) 2.01(2) 2.859(4) 177(4) . yes
N1' H1' N2 0.89(2) 2.01(3) 2.878(4) 166(4) . yes

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
O1 C1 C2 C3 7.2(4) . . . . ?
O1 C1 C2 C10 -168.5(3) . . . . ?
O2 C1 C2 C3 -176.1(3) . . . . ?
O2 C1 C2 C10 8.2(5) . . . . ?
N2 C13 C14 N3 -0.7(4) . . . . ?
N3 C3 C4 C5 176.4(2) . . . . ?
N3 C3 C4 C9 -57.6(3) . . . . ?
C1 O1 C15 C16 83.5(4) . . . . ?
C1 C2 C3 N3 -147.9(3) . . . . ?
C1 C2 C3 C4 90.5(3) . . . . ?
C1 C2 C10 N1 167.3(3) . . . . ?
C1 C2 C10 C11 -11.9(5) . . . . ?
C2 C3 C4 C5 -62.8(3) . . . . ?
C2 C3 C4 C9 63.1(3) . . . . ?
C3 N3 C12 N1 12.1(4) . . . . ?
C3 N3 C12 N2 -169.0(3) . . . . ?
C3 N3 C14 C13 168.1(3) . . . . ?
C3 C2 C10 N1 -8.3(5) . . . . ?
C3 C2 C10 C11 172.5(3) . . . . ?
C3 C4 C5 C6 -176.1(2) . . . . ?
C3 C4 C9 C8 176.9(3) . . . . ?
C4 C5 C6 C7 -56.8(3) . . . . ?
C5 C4 C9 C8 -55.9(3) . . . . ?
C5 C6 C7 C8 55.5(3) . . . . ?
C6 C7 C8 C9 -53.8(4) . . . . ?
C7 C8 C9 C4 54.4(4) . . . . ?
C9 C4 C5 C6 56.7(3) . . . . ?
C10 N1 C12 N2 -166.4(3) . . . . ?
C10 N1 C12 N3 12.3(5) . . . . ?
C10 C2 C3 N3 27.8(4) . . . . ?
C10 C2 C3 C4 -93.8(3) . . . . ?
C12 N1 C10 C2 -13.6(5) . . . . ?
C12 N1 C10 C11 165.7(3) . . . . ?
C12 N2 C13 C14 0.1(4) . . . . ?
C12 N3 C3 C2 -30.1(4) . . . . ?
C12 N3 C3 C4 95.1(3) . . . . ?
C12 N3 C14 C13 0.9(3) . . . . ?
C13 N2 C12 N1 179.4(3) . . . . ?
C13 N2 C12 N3 0.5(4) . . . . ?
C14 N3 C3 C2 164.7(3) . . . . ?
C14 N3 C3 C4 -70.1(4) . . . . ?
C14 N3 C12 N1 -179.9(3) . . . . ?
C14 N3 C12 N2 -1.0(4) . . . . ?
C15 O1 C1 O2 -1.3(5) . . . . ?
C15 O1 C1 C2 175.7(3) . . . . ?
O1' C1' C2' C3' -9.2(4) . . . . ?
O1' C1' C2' C10' 167.5(3) . . . . ?
O2' C1' C2' C3' 172.7(3) . . . . ?
O2' C1' C2' C10' -10.6(5) . . . . ?
N2' C13' C14' N3' 0.3(4) . . . . ?
N3' C3' C4' C5' -175.0(3) . . . . ?
N3' C3' C4' C9' 59.4(3) . . . . ?
C1' O1' C15' C16' -83.7(4) . . . . ?
C1' C2' C3' N3' 149.1(3) . . . . ?
C1' C2' C3' C4' -89.2(3) . . . . ?
C1' C2' C10' N1' -168.4(3) . . . . ?
C1' C2' C10' C11' 11.9(5) . . . . ?
C2' C3' C4' C5' 64.3(3) . . . . ?
C2' C3' C4' C9' -61.3(4) . . . . ?
C3' N3' C12' N1' -12.4(4) . . . . ?
C3' N3' C12' N2' 169.1(3) . . . . ?
C3' N3' C14' C13' -167.9(3) . . . . ?
C3' C2' C10' N1' 8.2(5) . . . . ?
C3' C2' C10' C11' -171.4(3) . . . . ?
C3' C4' C5' C6' 176.1(3) . . . . ?
C3' C4' C9' C8' -177.1(3) . . . . ?
C4' C5' C6' C7' 56.3(4) . . . . ?
C5' C4' C9' C8' 56.1(4) . . . . ?
C5' C6' C7' C8' -54.3(4) . . . . ?
C6' C7' C8' C9' 53.2(4) . . . . ?
C7' C8' C9' C4' -54.7(4) . . . . ?
C9' C4' C5' C6' -56.9(4) . . . . ?
C10' N1' C12' N2' 166.2(3) . . . . ?
C10' N1' C12' N3' -12.0(4) . . . . ?
C10' C2' C3' N3' -27.6(4) . . . . ?
C10' C2' C3' C4' 94.1(4) . . . . ?
C12' N1' C10' C2' 13.5(5) . . . . ?
C12' N1' C10' C11' -166.8(3) . . . . ?
C12' N2' C13' C14' 0.4(4) . . . . ?
C12' N3' C3' C2' 29.9(4) . . . . ?
C12' N3' C3' C4' -95.5(3) . . . . ?
C12' N3' C14' C13' -0.9(3) . . . . ?
C13' N2' C12' N1' -179.4(3) . . . . ?
C13' N2' C12' N3' -1.0(4) . . . . ?
C14' N3' C3' C2' -164.9(3) . . . . ?
C14' N3' C3' C4' 69.6(4) . . . . ?
C14' N3' C12' N1' 179.7(3) . . . . ?
C14' N3' C12' N2' 1.2(4) . . . . ?
C15' O1' C1' O2' -0.7(4) . . . . ?
C15' O1' C1' C2' -178.8(3) . . . . ?

####################################################################### 
# 
# 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_2076_P21c
_database_code_depnum_ccdc_archive 'CCDC 2338774'
loop_
_audit_author_name
_audit_author_address
'Christopher Golz'
;Georg August University Goettingen
Germany
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
loop_
_audit_author_email
shahilan.ratnam@uni-goettingen.de
'cgolz@gwdg.de '
djansse@gwdg.de

_audit_creation_method           
;FinalCif V123 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2023-08-16
_diffrn_source_power             0.05
_exptl_crystal_colour_primary    colourless
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      def2-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2023-08-16_09-10-10
;
_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
;
_olex2_submission_special_instructions 'No special instructions were received'
_refine_ls_d_res_high            0.6504
_refine_ls_d_res_low             7.5045
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C15 H24 N2 O2 S'
_chemical_formula_moiety         'C15 H24 N2 O2 S'
_chemical_formula_weight         296.436
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_symmetry_Int_Tables_number      14
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_vrf_PLAT230_2076_P21c           
;PROBLEM: Hirshfeld Test Diff for    S1       --C1       .       10.3 s.u.  
RESPONSE: ADP of S1 may have been influenced by absorption effects that become 
more apparent in non-spherical refinements. Indeed the highest residual 
densities are located around S1. However, the ellipsoids do not appear 
particularly problematic, given that C1 is a terminal methyl group.
;

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_cell_length_a                   13.3817(7)
_cell_length_b                   9.0674(5)
_cell_length_c                   12.4298(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.322(2)
_cell_angle_gamma                90
_cell_volume                     1506.96(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9639
_cell_measurement_theta_min      2.715
_cell_measurement_theta_max      33.151
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'from a mixture of ethyl acetate and pentane.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             640.849
_exptl_crystal_size_max          0.594
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7542
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1592 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.7542.
The λ/2 correction factor is Not present.
;
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.0
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            53044
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         33.12
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.9527
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9527
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9527
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_reflns_number_total             5461
_reflns_number_gt                5179
_reflns_threshold_expression     I>=2u(I)
_reflns_Friedel_coverage         0.0
_reflns_Friedel_fraction_max     ?
_reflns_Friedel_fraction_full    ?
_reflns_limit_h_min              -20
_reflns_limit_h_max              20
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              18
_reflns_special_details          ?
_computing_data_collection       
'Bruker BIS V6.2.15/2021-03-16 && APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0141P)²+0.0246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         5461
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0162
_refine_ls_R_factor_gt           0.0144
_refine_ls_wR_factor_ref         0.0334
_refine_ls_wR_factor_gt          0.0325
_refine_ls_goodness_of_fit_ref   1.1160
_refine_ls_restrained_S_all      1.1160
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_diff_density_max         0.1678
_refine_diff_density_min         -0.1356
_refine_diff_density_rms         0.0297
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_geom_special_details            ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -2.00 0.2540
-2.00 -1.00 -2.00 0.2110
-1.00 0.00 -2.00 0.2790
0.00 1.00 -2.00 0.2620
1.00 2.00 -2.00 0.2040
1.00 0.00 -1.00 0.2310
-1.00 -1.00 -1.00 0.1740
0.00 0.00 -1.00 0.2960
-2.00 2.00 -1.00 0.1270
2.00 1.00 0.00 0.0680
-2.00 -1.00 0.00 0.0800
-1.00 0.00 0.00 0.0510
1.00 0.00 0.00 0.0450
-2.00 1.00 0.00 0.0720
1.00 -1.00 0.00 0.1110
-1.00 1.00 0.00 0.0720
0.00 1.00 0.00 0.0760
0.00 -1.00 0.00 0.1130
-1.00 0.00 1.00 0.2170
1.00 1.00 1.00 0.1870
0.00 0.00 1.00 0.2650
0.00 -2.00 1.00 0.1770
0.00 1.00 2.00 0.2540
2.00 1.00 2.00 0.2050
1.00 0.00 2.00 0.2450
0.00 -1.00 2.00 0.2450

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
S1 S 0.306917(6) 0.528079(8) 0.824539(6) 0.01330(2) Uani 1.000000 .
O1 O 0.357891(16) 0.42755(2) 0.316690(17) 0.01272(4) Uani 1.000000 .
O2 O 0.442050(17) 0.64251(2) 0.317054(17) 0.01384(4) Uani 1.000000 .
N1 N 0.368649(19) 0.65769(3) 0.64966(2) 0.01155(5) Uani 1.000000 .
H1 H 0.4015(4) 0.7217(6) 0.7047(5) 0.0305(13) Uani 1.000000 .
N2 N 0.262633(19) 0.45162(3) 0.62054(2) 0.01149(5) Uani 1.000000 .
C1 C 0.21243(2) 0.38840(4) 0.83656(3) 0.01633(6) Uani 1.000000 .
H1a H 0.1501(4) 0.4117(7) 0.7815(5) 0.0427(16) Uani 1.000000 .
H1b H 0.1883(5) 0.3927(7) 0.9179(4) 0.0506(18) Uani 1.000000 .
H1c H 0.2420(5) 0.2815(6) 0.8199(6) 0.0564(19) Uani 1.000000 .
C2 C 0.30961(2) 0.54156(3) 0.68284(2) 0.01052(5) Uani 1.000000 .
C3 C 0.48496(2) 0.76366(3) 0.52577(2) 0.01298(5) Uani 1.000000 .
H3a H 0.4604(4) 0.8550(6) 0.4751(5) 0.0379(15) Uani 1.000000 .
H3b H 0.5432(4) 0.7080(6) 0.4830(5) 0.0389(15) Uani 1.000000 .
H3c H 0.5161(4) 0.8060(6) 0.6007(4) 0.0410(15) Uani 1.000000 .
C4 C 0.39950(2) 0.66101(3) 0.54480(2) 0.00999(5) Uani 1.000000 .
C5 C 0.35184(2) 0.57085(3) 0.47154(2) 0.00978(5) Uani 1.000000 .
C6 C 0.26053(2) 0.48451(3) 0.50442(2) 0.01022(5) Uani 1.000000 .
H6 H 0.2599(3) 0.3770(5) 0.4632(4) 0.0219(11) Uani 1.000000 .
C7 C 0.15999(2) 0.56127(3) 0.47285(2) 0.01117(5) Uani 1.000000 .
H7 H 0.1018(4) 0.4881(5) 0.5045(4) 0.0248(12) Uani 1.000000 .
C8 C 0.14226(2) 0.57138(4) 0.35035(2) 0.01487(6) Uani 1.000000 .
H8a H 0.1998(4) 0.6426(6) 0.3166(4) 0.0335(13) Uani 1.000000 .
H8b H 0.1507(4) 0.4619(6) 0.3138(4) 0.0315(13) Uani 1.000000 .
C9 C 0.03897(2) 0.63527(4) 0.32048(3) 0.01868(6) Uani 1.000000 .
H9a H 0.0286(4) 0.6448(7) 0.2330(4) 0.0391(15) Uani 1.000000 .
H9b H -0.0185(4) 0.5590(6) 0.3477(4) 0.0354(14) Uani 1.000000 .
C10 C 0.02451(3) 0.78619(4) 0.37253(3) 0.02253(7) Uani 1.000000 .
H10a H -0.0513(4) 0.8269(7) 0.3541(5) 0.0443(16) Uani 1.000000 .
H10b H 0.0770(5) 0.8653(6) 0.3362(5) 0.0455(16) Uani 1.000000 .
C11 C 0.04496(2) 0.78017(4) 0.49453(3) 0.01912(6) Uani 1.000000 .
H11a H -0.0133(4) 0.7135(6) 0.5316(4) 0.0369(14) Uani 1.000000 .
H11b H 0.0395(4) 0.8910(6) 0.5289(5) 0.0403(15) Uani 1.000000 .
C12 C 0.14776(2) 0.71377(3) 0.52390(3) 0.01441(6) Uani 1.000000 .
H12a H 0.1574(4) 0.7067(6) 0.6118(4) 0.0304(13) Uani 1.000000 .
H12b H 0.2058(4) 0.7866(5) 0.4956(4) 0.0298(12) Uani 1.000000 .
C13 C 0.38875(2) 0.55478(3) 0.36287(2) 0.01010(5) Uani 1.000000 .
C14 C 0.38821(2) 0.39622(3) 0.20846(2) 0.01403(6) Uani 1.000000 .
H14a H 0.3984(4) 0.2787(5) 0.2068(4) 0.0332(13) Uani 1.000000 .
H14b H 0.4589(4) 0.4518(6) 0.1948(4) 0.0313(13) Uani 1.000000 .
C15 C 0.30786(3) 0.44247(4) 0.12644(3) 0.01796(6) Uani 1.000000 .
H15a H 0.3332(5) 0.4192(7) 0.0466(4) 0.0457(16) Uani 1.000000 .
H15b H 0.2910(5) 0.5583(6) 0.1316(5) 0.0428(16) Uani 1.000000 .
H15c H 0.2397(4) 0.3812(7) 0.1373(5) 0.0392(14) 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
S1 C1 1.8001(3) . ?
S1 C2 1.7673(3) . ?
O1 C13 1.3460(3) . ?
O1 C14 1.4490(4) . ?
O2 C13 1.2242(4) . ?
N1 H1 0.987(6) . ?
N1 C2 1.3890(4) . ?
N1 C4 1.3835(4) . ?
N2 C2 1.2729(4) . ?
N2 C6 1.4731(4) . ?
C1 H1a 1.079(5) . ?
C1 H1b 1.074(5) . ?
C1 H1c 1.070(6) . ?
C3 H3a 1.084(5) . ?
C3 H3b 1.086(5) . ?
C3 H3c 1.076(5) . ?
C3 C4 1.5006(4) . ?
C4 C5 1.3628(4) . ?
C5 C6 1.5210(4) . ?
C5 C13 1.4641(4) . ?
C6 H6 1.101(4) . ?
C6 C7 1.5510(4) . ?
C7 H7 1.108(5) . ?
C7 C8 1.5342(4) . ?
C7 C12 1.5329(4) . ?
C8 H8a 1.101(5) . ?
C8 H8b 1.099(5) . ?
C8 C9 1.5305(4) . ?
C9 H9a 1.094(5) . ?
C9 H9b 1.098(5) . ?
C9 C10 1.5293(5) . ?
C10 H10a 1.095(5) . ?
C10 H10b 1.112(5) . ?
C10 C11 1.5309(5) . ?
C11 H11a 1.102(5) . ?
C11 H11b 1.095(5) . ?
C11 C12 1.5321(4) . ?
C12 H12a 1.096(5) . ?
C12 H12b 1.089(5) . ?
C14 H14a 1.074(5) . ?
C14 H14b 1.091(5) . ?
C14 C15 1.5108(4) . ?
C15 H15a 1.082(5) . ?
C15 H15b 1.077(6) . ?
C15 H15c 1.081(5) . ?

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
C2 S1 C1 100.029(14) . . ?
C14 O1 C13 118.13(2) . . ?
C2 N1 H1 118.9(3) . . ?
C4 N1 H1 119.9(3) . . ?
C4 N1 C2 119.43(2) . . ?
C6 N2 C2 117.11(2) . . ?
H1a C1 S1 109.7(3) . . ?
H1b C1 S1 107.0(3) . . ?
H1b C1 H1a 109.6(5) . . ?
H1c C1 S1 110.7(3) . . ?
H1c C1 H1a 109.7(5) . . ?
H1c C1 H1b 110.1(5) . . ?
N1 C2 S1 112.53(2) . . ?
N2 C2 S1 122.17(2) . . ?
N2 C2 N1 125.30(3) . . ?
H3b C3 H3a 106.1(5) . . ?
H3c C3 H3a 109.2(4) . . ?
H3c C3 H3b 109.3(4) . . ?
C4 C3 H3a 110.5(3) . . ?
C4 C3 H3b 110.8(3) . . ?
C4 C3 H3c 110.8(3) . . ?
C3 C4 N1 114.86(2) . . ?
C5 C4 N1 117.84(3) . . ?
C5 C4 C3 127.28(3) . . ?
C6 C5 C4 119.25(3) . . ?
C13 C5 C4 120.65(3) . . ?
C13 C5 C6 120.09(2) . . ?
C5 C6 N2 112.57(2) . . ?
H6 C6 N2 106.0(2) . . ?
H6 C6 C5 108.8(2) . . ?
C7 C6 N2 108.71(2) . . ?
C7 C6 C5 113.52(2) . . ?
C7 C6 H6 106.8(2) . . ?
H7 C7 C6 104.9(3) . . ?
C8 C7 C6 112.06(2) . . ?
C8 C7 H7 107.8(3) . . ?
C12 C7 C6 113.96(2) . . ?
C12 C7 H7 107.7(3) . . ?
C12 C7 C8 110.01(2) . . ?
H8a C8 C7 109.3(3) . . ?
H8b C8 C7 110.0(3) . . ?
H8b C8 H8a 106.7(4) . . ?
C9 C8 C7 111.42(3) . . ?
C9 C8 H8a 108.9(3) . . ?
C9 C8 H8b 110.4(3) . . ?
H9a C9 C8 110.3(3) . . ?
H9b C9 C8 108.9(3) . . ?
H9b C9 H9a 107.1(4) . . ?
C10 C9 C8 111.38(3) . . ?
C10 C9 H9a 109.7(3) . . ?
C10 C9 H9b 109.3(3) . . ?
H10a C10 C9 110.2(3) . . ?
H10b C10 C9 108.2(3) . . ?
H10b C10 H10a 107.0(4) . . ?
C11 C10 C9 111.50(3) . . ?
C11 C10 H10a 110.3(3) . . ?
C11 C10 H10b 109.5(3) . . ?
H11a C11 C10 109.4(3) . . ?
H11b C11 C10 110.0(3) . . ?
H11b C11 H11a 106.3(4) . . ?
C12 C11 C10 111.89(3) . . ?
C12 C11 H11a 109.2(3) . . ?
C12 C11 H11b 109.9(3) . . ?
C11 C12 C7 111.45(2) . . ?
H12a C12 C7 110.5(3) . . ?
H12a C12 C11 109.2(3) . . ?
H12b C12 C7 108.9(3) . . ?
H12b C12 C11 109.3(3) . . ?
H12b C12 H12a 107.5(4) . . ?
O2 C13 O1 122.21(3) . . ?
C5 C13 O1 111.69(2) . . ?
C5 C13 O2 126.10(3) . . ?
H14a C14 O1 104.6(3) . . ?
H14b C14 O1 109.3(3) . . ?
H14b C14 H14a 110.0(4) . . ?
C15 C14 O1 110.71(3) . . ?
C15 C14 H14a 110.5(3) . . ?
C15 C14 H14b 111.4(3) . . ?
H15a C15 C14 108.9(3) . . ?
H15b C15 C14 112.0(3) . . ?
H15b C15 H15a 108.6(5) . . ?
H15c C15 C14 110.8(3) . . ?
H15c C15 H15a 108.1(5) . . ?
H15c C15 H15b 108.3(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
S1 C2 N1 C4 163.430(19) . . . . ?
S1 C2 N2 C6 172.80(2) . . . . ?
O1 C13 C5 C4 157.38(2) . . . . ?
O1 C13 C5 C6 -21.54(3) . . . . ?
O2 C13 C5 C4 -21.88(3) . . . . ?
O2 C13 C5 C6 159.21(3) . . . . ?
N1 C2 N2 C6 -8.09(3) . . . . ?
N1 C4 C5 C6 6.74(3) . . . . ?
N1 C4 C5 C13 -172.18(2) . . . . ?
N2 C6 C5 C4 -28.10(3) . . . . ?
N2 C6 C5 C13 150.83(2) . . . . ?
N2 C6 C7 C8 -168.49(2) . . . . ?
N2 C6 C7 C12 65.77(2) . . . . ?
C3 C4 C5 C6 -174.72(3) . . . . ?
C3 C4 C5 C13 6.36(3) . . . . ?
C4 C5 C6 C7 95.93(3) . . . . ?
C5 C6 C7 C8 65.41(3) . . . . ?
C5 C6 C7 C12 -60.34(3) . . . . ?
C6 C7 C8 C9 175.13(2) . . . . ?
C6 C7 C12 C11 -176.97(3) . . . . ?
C7 C8 C9 C10 56.18(3) . . . . ?
C7 C12 C11 C10 -54.91(3) . . . . ?
C8 C9 C10 C11 -53.86(3) . . . . ?
C9 C10 C11 C12 53.36(3) . . . . ?


