# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_crocu
_database_code_depnum_ccdc_archive 'CCDC 2289675'
loop_
_audit_author_name
_audit_author_address
'Peter G. Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-08-20 deposited with the CCDC.	2023-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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'

_cell_length_a                   6.14568(10)
_cell_length_b                   12.1476(2)
_cell_length_c                   16.5252(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.6799(16)
_cell_angle_gamma                90
_cell_volume                     1233.61(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    74405
_cell_measurement_theta_min      2.0660
_cell_measurement_theta_max      41.4180

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73275
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      99.97(18)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            123169
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.465
_diffrn_reflns_theta_max         41.172
_diffrn_reflns_theta_full        40.500
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             16066
_reflns_number_gt                15117
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.981
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.998

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;
 The structure was refined as a 2-component pseudomerohedral twin (by 180
 degree rotation about the "a" axis). The relative volume of the minor twin
 component refined to 0.0977(9). The size of the integration box (used in
 the data reduction) was multiplied by 1.5 to enable better measurement
 of the split reflections.

 The hydrogen atoms of the NH groups were refined freely, but with N-H distances
 restrained to be approximately equal (command "SADI").

 In the second independent molecule, the atoms C1' to C4' are disordered over
 two sets of positions. The occupation factors of the minor disorder component
 refined to 0.078(5). Appropriate restraints were employed to improve
 refinement stability, but the dimensions of disordered groups should always be
 intepreted with caution.

 CHECKCIF suggests the higher symmetry space group Pca2(1), but only with an 87%
 fit. The clear deviation of the beta angle from 90 degrees rules out this
 possibility, so the "extra" symmetry in fact corresponds to pseudosymmetry.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0684P)²+0.0805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 7119 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration .
_refine_ls_number_reflns         16066
_refine_ls_number_parameters     353
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.87091(18) 0.86477(9) 0.64304(7) 0.01551(16) Uani 1 1 d . . . . .
H1A H 0.969204 0.929053 0.639015 0.019 Uiso 1 1 calc R U . . .
H1B H 0.947439 0.807417 0.675027 0.019 Uiso 1 1 calc R U . . .
C2 C 0.6646(2) 0.89944(10) 0.68805(7) 0.01787(17) Uani 1 1 d . . . . .
H2A H 0.628527 0.976404 0.673460 0.021 Uiso 1 1 calc R U . . .
H2B H 0.694405 0.897114 0.747031 0.021 Uiso 1 1 calc R U . . .
C3 C 0.46684(19) 0.82564(10) 0.66861(7) 0.01760(17) Uani 1 1 d . . . . .
H3A H 0.380062 0.815662 0.718168 0.021 Uiso 1 1 calc R U . . .
H3B H 0.373372 0.862408 0.627574 0.021 Uiso 1 1 calc R U . . .
C4 C 0.53624(19) 0.71274(9) 0.63672(7) 0.01611(16) Uani 1 1 d . . . . .
H4A H 0.405461 0.666357 0.628329 0.019 Uiso 1 1 calc R U . . .
H4B H 0.630338 0.676217 0.677678 0.019 Uiso 1 1 calc R U . . .
C4A C 0.66079(16) 0.72174(8) 0.55618(6) 0.01254(14) Uani 1 1 d . . . . .
C4B C 0.51112(16) 0.75848(8) 0.48900(6) 0.01205(14) Uani 1 1 d . . . . .
N5 N 0.33352(15) 0.71302(7) 0.45324(6) 0.01322(13) Uani 1 1 d D . . . .
H05 H 0.281(5) 0.651(2) 0.4634(16) 0.030(6) Uiso 1 1 d D . . . .
C5A C 0.24585(17) 0.79038(8) 0.39908(6) 0.01234(14) Uani 1 1 d . . . . .
C6 C 0.05758(18) 0.78307(9) 0.35146(7) 0.01539(16) Uani 1 1 d . . . . .
H6 H -0.029585 0.718484 0.351057 0.018 Uiso 1 1 calc R U . . .
C7 C 0.0026(2) 0.87444(10) 0.30445(7) 0.01746(17) Uani 1 1 d . . . . .
H7 H -0.125560 0.872452 0.271743 0.021 Uiso 1 1 calc R U . . .
C8 C 0.1329(2) 0.96930(10) 0.30455(7) 0.01761(17) Uani 1 1 d . . . . .
H8 H 0.092286 1.029806 0.271228 0.021 Uiso 1 1 calc R U . . .
C9 C 0.32027(18) 0.97673(9) 0.35237(6) 0.01488(15) Uani 1 1 d . . . . .
H9 H 0.406858 1.041508 0.352167 0.018 Uiso 1 1 calc R U . . .
C9A C 0.37833(16) 0.88643(8) 0.40085(6) 0.01213(14) Uani 1 1 d . . . . .
C9B C 0.54826(16) 0.86321(8) 0.45919(6) 0.01227(14) Uani 1 1 d . . . . .
C10 C 0.73445(16) 0.90924(8) 0.50040(6) 0.01206(13) Uani 1 1 d . . . . .
O1 O 0.81634(15) 1.00174(7) 0.49473(6) 0.01658(13) Uani 1 1 d . . . . .
C10A C 0.82469(16) 0.82034(8) 0.55811(6) 0.01255(14) Uani 1 1 d . . . . .
H10A H 0.965509 0.793652 0.535602 0.015 Uiso 1 1 calc R U . . .
C11 C 0.7733(2) 0.61201(9) 0.53828(8) 0.01898(18) Uani 1 1 d . . . . .
H11A H 0.666417 0.552243 0.540425 0.028 Uiso 1 1 calc R U . . .
H11B H 0.888324 0.598897 0.578722 0.028 Uiso 1 1 calc R U . . .
H11C H 0.837132 0.614702 0.484257 0.028 Uiso 1 1 calc R U . . .
C4B' C 0.51739(16) 0.25384(8) 0.47958(6) 0.01246(14) Uani 1 1 d . . . . .
N5' N 0.69013(16) 0.20982(7) 0.44130(6) 0.01411(14) Uani 1 1 d D . . . .
H05' H 0.745(5) 0.148(2) 0.4523(17) 0.032(7) Uiso 1 1 d D . . . .
C5A' C 0.76692(18) 0.28839(9) 0.38651(7) 0.01393(15) Uani 1 1 d . . . . .
C6' C 0.95127(19) 0.28462(10) 0.33836(7) 0.01747(17) Uani 1 1 d . . . . .
H6'1 H 1.041633 0.221217 0.337018 0.021 Uiso 1 1 calc R U . . .
C7' C 0.9979(2) 0.37746(11) 0.29229(8) 0.0202(2) Uani 1 1 d . . . . .
H7' H 1.123156 0.377640 0.259153 0.024 Uiso 1 1 calc R U . . .
C8' C 0.8631(2) 0.47089(11) 0.29387(7) 0.01947(19) Uani 1 1 d . . . . .
H8' H 0.897819 0.532614 0.261158 0.023 Uiso 1 1 calc R U . . .
C9' C 0.6800(2) 0.47469(9) 0.34239(7) 0.01686(17) Uani 1 1 d . . . . .
H9' H 0.589929 0.538215 0.343131 0.020 Uiso 1 1 calc R U . . .
C9A' C 0.63123(18) 0.38307(8) 0.39011(6) 0.01382(15) Uani 1 1 d . . . . .
C9B' C 0.47092(17) 0.35818(8) 0.45037(6) 0.01345(14) Uani 1 1 d . . . . .
C10' C 0.30378(16) 0.40621(8) 0.49919(7) 0.01317(14) Uani 1 1 d . . . . .
O1' O 0.23058(16) 0.50067(7) 0.49938(7) 0.01912(15) Uani 1 1 d . . . . .
C11' C 0.3084(2) 0.10816(9) 0.56009(8) 0.01842(18) Uani 1 1 d . . . . .
H11D H 0.197756 0.099066 0.517415 0.028 Uiso 1 1 calc R U . . .
H11E H 0.241903 0.096661 0.613033 0.028 Uiso 1 1 calc R U . . .
H11F H 0.424923 0.054230 0.552413 0.028 Uiso 1 1 calc R U . . .
C10" C 0.22212(16) 0.31493(8) 0.55598(6) 0.01252(14) Uani 1 1 d D . . . .
H10" H 0.091006 0.281901 0.529039 0.015 Uiso 1 1 calc R U . A 1
C1' C 0.1493(3) 0.3549(2) 0.63886(11) 0.0138(4) Uani 0.922(4) 1 d D U P B 1
H1A' H 0.051215 0.299229 0.662545 0.017 Uiso 0.922(4) 1 calc R U P B 1
H1B' H 0.065215 0.423869 0.631922 0.017 Uiso 0.922(4) 1 calc R U P B 1
C2' C 0.3386(2) 0.37604(14) 0.69798(10) 0.0166(2) Uani 0.922(4) 1 d D U P B 1
H2A' H 0.428187 0.437888 0.678049 0.020 Uiso 0.922(4) 1 calc R U P B 1
H2B' H 0.281016 0.396696 0.751572 0.020 Uiso 0.922(4) 1 calc R U P B 1
C3' C 0.4796(2) 0.27269(10) 0.70626(7) 0.0159(2) Uani 0.922(4) 1 d D . P B 1
H3A' H 0.597530 0.285671 0.746446 0.019 Uiso 0.922(4) 1 calc R U P B 1
H3B' H 0.389876 0.210448 0.725433 0.019 Uiso 0.922(4) 1 calc R U P B 1
C4' C 0.57713(18) 0.24446(10) 0.62436(7) 0.0136(2) Uani 0.922(4) 1 d D U P B 1
H4A' H 0.668079 0.177628 0.630368 0.016 Uiso 0.922(4) 1 calc R U P B 1
H4B' H 0.673336 0.305491 0.607563 0.016 Uiso 0.922(4) 1 calc R U P B 1
C1" C 0.159(5) 0.356(6) 0.641(2) 0.034(10) Uiso 0.078(4) 1 d D U P B 2
H1"1 H 0.048687 0.414645 0.635841 0.041 Uiso 0.078(4) 1 calc R U P B 2
H1"2 H 0.096056 0.294394 0.672074 0.041 Uiso 0.078(4) 1 calc R U P B 2
C2" C 0.360(3) 0.3998(19) 0.6845(15) 0.024(5) Uiso 0.078(4) 1 d D U P B 2
H2"1 H 0.388847 0.476100 0.666539 0.029 Uiso 0.078(4) 1 calc R U P B 2
H2"2 H 0.333619 0.401345 0.743487 0.029 Uiso 0.078(4) 1 calc R U P B 2
C3" C 0.556(2) 0.3294(12) 0.6679(10) 0.019(3) Uiso 0.078(4) 1 d D . P B 2
H3"1 H 0.641526 0.321214 0.718593 0.022 Uiso 0.078(4) 1 calc R U P B 2
H3"2 H 0.648265 0.367626 0.628149 0.022 Uiso 0.078(4) 1 calc R U P B 2
C4" C 0.500(3) 0.2164(12) 0.6357(9) 0.017(3) Uiso 0.078(4) 1 d D U P B 2
H4"1 H 0.634315 0.171298 0.633206 0.020 Uiso 0.078(4) 1 calc R U P B 2
H4"2 H 0.398189 0.179561 0.672897 0.020 Uiso 0.078(4) 1 calc R U P B 2
C4A' C 0.40253(16) 0.22399(8) 0.55606(6) 0.01240(14) Uani 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10A 1.5273(15) . ?
C1 C2 1.5363(17) . ?
C2 C3 1.5412(17) . ?
C3 C4 1.5316(17) . ?
C4 C4A 1.5470(15) . ?
C4A C4B 1.5013(14) . ?
C4A C11 1.5320(15) . ?
C4A C10A 1.5651(14) . ?
C4B N5 1.3528(14) . ?
C4B C9B 1.3841(14) . ?
N5 C5A 1.4011(13) . ?
C5A C6 1.3944(15) . ?
C5A C9A 1.4229(14) . ?
C6 C7 1.3941(16) . ?
C7 C8 1.4033(17) . ?
C8 C9 1.3919(16) . ?
C9 C9A 1.4019(14) . ?
C9A C9B 1.4408(14) . ?
C9B C10 1.4378(14) . ?
C10 O1 1.2352(13) . ?
C10 C10A 1.5397(13) . ?
C4B' N5' 1.3525(14) . ?
C4B' C9B' 1.3849(14) . ?
C4B' C4A' 1.4993(14) . ?
N5' C5A' 1.4013(14) . ?
C5A' C6' 1.3929(16) . ?
C5A' C9A' 1.4223(15) . ?
C6' C7' 1.3924(18) . ?
C7' C8' 1.405(2) . ?
C8' C9' 1.3903(17) . ?
C9' C9A' 1.3985(15) . ?
C9A' C9B' 1.4412(15) . ?
C9B' C10' 1.4373(15) . ?
C10' O1' 1.2325(13) . ?
C10' C10" 1.5405(14) . ?
C11' C4A' 1.5231(14) . ?
C10" C1' 1.5253(18) . ?
C10" C1" 1.54(2) . ?
C10" C4A' 1.5652(14) . ?
C1' C2' 1.532(2) . ?
C2' C3' 1.5305(19) . ?
C3' C4' 1.5257(17) . ?
C4' C4A' 1.5680(15) . ?
C1" C2" 1.52(3) . ?
C2" C3" 1.50(2) . ?
C3" C4" 1.510(18) . ?
C4" C4A' 1.444(15) . ?

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
C10A C1 C2 113.34(9) . . ?
C1 C2 C3 113.14(9) . . ?
C4 C3 C2 111.74(10) . . ?
C3 C4 C4A 112.05(9) . . ?
C4B C4A C11 112.95(9) . . ?
C4B C4A C4 110.62(9) . . ?
C11 C4A C4 109.49(9) . . ?
C4B C4A C10A 100.14(8) . . ?
C11 C4A C10A 112.20(9) . . ?
C4 C4A C10A 111.19(8) . . ?
N5 C4B C9B 110.82(9) . . ?
N5 C4B C4A 133.29(9) . . ?
C9B C4B C4A 115.74(9) . . ?
C4B N5 C5A 107.90(8) . . ?
C6 C5A N5 128.90(9) . . ?
C6 C5A C9A 122.32(9) . . ?
N5 C5A C9A 108.74(9) . . ?
C7 C6 C5A 117.26(10) . . ?
C6 C7 C8 121.23(10) . . ?
C9 C8 C7 121.49(10) . . ?
C8 C9 C9A 118.49(10) . . ?
C9 C9A C5A 119.22(9) . . ?
C9 C9A C9B 135.49(9) . . ?
C5A C9A C9B 105.26(8) . . ?
C4B C9B C10 108.82(8) . . ?
C4B C9B C9A 107.27(9) . . ?
C10 C9B C9A 143.82(9) . . ?
O1 C10 C9B 129.83(9) . . ?
O1 C10 C10A 122.75(9) . . ?
C9B C10 C10A 107.42(8) . . ?
C1 C10A C10 112.52(8) . . ?
C1 C10A C4A 113.69(8) . . ?
C10 C10A C4A 107.29(8) . . ?
N5' C4B' C9B' 111.01(9) . . ?
N5' C4B' C4A' 132.74(9) . . ?
C9B' C4B' C4A' 114.70(9) . . ?
C4B' N5' C5A' 107.77(9) . . ?
C6' C5A' N5' 128.99(10) . . ?
C6' C5A' C9A' 122.12(10) . . ?
N5' C5A' C9A' 108.76(9) . . ?
C7' C6' C5A' 117.38(11) . . ?
C6' C7' C8' 121.25(11) . . ?
C9' C8' C7' 121.24(11) . . ?
C8' C9' C9A' 118.64(11) . . ?
C9' C9A' C5A' 119.35(10) . . ?
C9' C9A' C9B' 135.19(10) . . ?
C5A' C9A' C9B' 105.38(9) . . ?
C4B' C9B' C10' 108.76(9) . . ?
C4B' C9B' C9A' 107.04(9) . . ?
C10' C9B' C9A' 143.29(9) . . ?
O1' C10' C9B' 129.98(10) . . ?
O1' C10' C10" 123.16(10) . . ?
C9B' C10' C10" 106.86(8) . . ?
C1' C10" C10' 114.76(14) . . ?
C1" C10" C10' 114(3) . . ?
C1' C10" C4A' 116.07(13) . . ?
C1" C10" C4A' 114(2) . . ?
C10' C10" C4A' 105.82(8) . . ?
C10" C1' C2' 113.41(13) . . ?
C3' C2' C1' 110.15(14) . . ?
C4' C3' C2' 109.45(10) . . ?
C3' C4' C4A' 113.66(9) . . ?
C2" C1" C10" 110(2) . . ?
C3" C2" C1" 111(2) . . ?
C2" C3" C4" 113.9(14) . . ?
C4A' C4" C3" 110.6(11) . . ?
C4" C4A' C4B' 126.1(7) . . ?
C4" C4A' C11' 93.2(6) . . ?
C4B' C4A' C11' 116.30(9) . . ?
C4" C4A' C10" 109.5(6) . . ?
C4B' C4A' C10" 99.74(8) . . ?
C11' C4A' C10" 112.50(9) . . ?
C4B' C4A' C4' 104.09(8) . . ?
C11' C4A' C4' 111.85(9) . . ?
C10" C4A' C4' 111.55(8) . . ?

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
C10A C1 C2 C3 35.14(14) . . . . ?
C1 C2 C3 C4 21.92(14) . . . . ?
C2 C3 C4 C4A -62.47(13) . . . . ?
C3 C4 C4A C4B -68.73(12) . . . . ?
C3 C4 C4A C11 166.16(10) . . . . ?
C3 C4 C4A C10A 41.61(12) . . . . ?
C11 C4A C4B N5 59.20(16) . . . . ?
C4 C4A C4B N5 -63.93(15) . . . . ?
C10A C4A C4B N5 178.71(11) . . . . ?
C11 C4A C4B C9B -125.78(10) . . . . ?
C4 C4A C4B C9B 111.09(10) . . . . ?
C10A C4A C4B C9B -6.27(11) . . . . ?
C9B C4B N5 C5A -1.32(12) . . . . ?
C4A C4B N5 C5A 173.88(11) . . . . ?
C4B N5 C5A C6 -176.65(11) . . . . ?
C4B N5 C5A C9A 1.13(12) . . . . ?
N5 C5A C6 C7 177.76(11) . . . . ?
C9A C5A C6 C7 0.25(16) . . . . ?
C5A C6 C7 C8 0.66(17) . . . . ?
C6 C7 C8 C9 -0.97(19) . . . . ?
C7 C8 C9 C9A 0.33(18) . . . . ?
C8 C9 C9A C5A 0.56(16) . . . . ?
C8 C9 C9A C9B -177.10(12) . . . . ?
C6 C5A C9A C9 -0.86(16) . . . . ?
N5 C5A C9A C9 -178.82(10) . . . . ?
C6 C5A C9A C9B 177.44(10) . . . . ?
N5 C5A C9A C9B -0.52(11) . . . . ?
N5 C4B C9B C10 178.46(9) . . . . ?
C4A C4B C9B C10 2.33(12) . . . . ?
N5 C4B C9B C9A 0.99(12) . . . . ?
C4A C4B C9B C9A -175.14(9) . . . . ?
C9 C9A C9B C4B 177.62(12) . . . . ?
C5A C9A C9B C4B -0.26(11) . . . . ?
C9 C9A C9B C10 1.7(3) . . . . ?
C5A C9A C9B C10 -176.20(14) . . . . ?
C4B C9B C10 O1 -176.51(11) . . . . ?
C9A C9B C10 O1 -0.6(2) . . . . ?
C4B C9B C10 C10A 2.96(11) . . . . ?
C9A C9B C10 C10A 178.86(14) . . . . ?
C2 C1 C10A C10 66.56(12) . . . . ?
C2 C1 C10A C4A -55.67(12) . . . . ?
O1 C10 C10A C1 46.94(14) . . . . ?
C9B C10 C10A C1 -132.58(9) . . . . ?
O1 C10 C10A C4A 172.71(10) . . . . ?
C9B C10 C10A C4A -6.80(11) . . . . ?
C4B C4A C10A C1 132.54(9) . . . . ?
C11 C4A C10A C1 -107.41(11) . . . . ?
C4 C4A C10A C1 15.61(11) . . . . ?
C4B C4A C10A C10 7.47(10) . . . . ?
C11 C4A C10A C10 127.52(9) . . . . ?
C4 C4A C10A C10 -109.47(9) . . . . ?
C9B' C4B' N5' C5A' 2.01(12) . . . . ?
C4A' C4B' N5' C5A' -162.69(11) . . . . ?
C4B' N5' C5A' C6' 174.26(11) . . . . ?
C4B' N5' C5A' C9A' -1.65(12) . . . . ?
N5' C5A' C6' C7' -176.24(11) . . . . ?
C9A' C5A' C6' C7' -0.81(17) . . . . ?
C5A' C6' C7' C8' -0.49(18) . . . . ?
C6' C7' C8' C9' 0.9(2) . . . . ?
C7' C8' C9' C9A' -0.06(18) . . . . ?
C8' C9' C9A' C5A' -1.20(16) . . . . ?
C8' C9' C9A' C9B' 175.02(12) . . . . ?
C6' C5A' C9A' C9' 1.68(16) . . . . ?
N5' C5A' C9A' C9' 177.93(10) . . . . ?
C6' C5A' C9A' C9B' -175.56(11) . . . . ?
N5' C5A' C9A' C9B' 0.69(12) . . . . ?
N5' C4B' C9B' C10' -173.29(9) . . . . ?
C4A' C4B' C9B' C10' -5.61(13) . . . . ?
N5' C4B' C9B' C9A' -1.57(12) . . . . ?
C4A' C4B' C9B' C9A' 166.12(9) . . . . ?
C9' C9A' C9B' C4B' -176.10(12) . . . . ?
C5A' C9A' C9B' C4B' 0.49(12) . . . . ?
C9' C9A' C9B' C10' -9.3(3) . . . . ?
C5A' C9A' C9B' C10' 167.32(15) . . . . ?
C4B' C9B' C10' O1' 171.93(12) . . . . ?
C9A' C9B' C10' O1' 5.2(2) . . . . ?
C4B' C9B' C10' C10" -8.16(12) . . . . ?
C9A' C9B' C10' C10" -174.85(14) . . . . ?
O1' C10' C10" C1' -32.81(16) . . . . ?
C9B' C10' C10" C1' 147.27(12) . . . . ?
O1' C10' C10" C1" -35.5(15) . . . . ?
C9B' C10' C10" C1" 144.5(15) . . . . ?
O1' C10' C10" C4A' -162.13(11) . . . . ?
C9B' C10' C10" C4A' 17.94(11) . . . . ?
C10' C10" C1' C2' -79.7(2) . . . . ?
C4A' C10" C1' C2' 44.3(2) . . . . ?
C10" C1' C2' C3' -55.4(2) . . . . ?
C1' C2' C3' C4' 62.08(17) . . . . ?
C2' C3' C4' C4A' -58.63(13) . . . . ?
C10' C10" C1" C2" -65(4) . . . . ?
C4A' C10" C1" C2" 57(5) . . . . ?
C10" C1" C2" C3" -39(5) . . . . ?
C1" C2" C3" C4" -18(3) . . . . ?
C2" C3" C4" C4A' 66.8(19) . . . . ?
C3" C4" C4A' C4B' 71.7(12) . . . . ?
C3" C4" C4A' C11' -162.1(11) . . . . ?
C3" C4" C4A' C10" -46.9(13) . . . . ?
N5' C4B' C4A' C4" 57.5(7) . . . . ?
C9B' C4B' C4A' C4" -106.8(7) . . . . ?
N5' C4B' C4A' C11' -58.41(16) . . . . ?
C9B' C4B' C4A' C11' 137.32(10) . . . . ?
N5' C4B' C4A' C10" -179.61(11) . . . . ?
C9B' C4B' C4A' C10" 16.12(11) . . . . ?
N5' C4B' C4A' C4' 65.09(14) . . . . ?
C9B' C4B' C4A' C4' -99.18(10) . . . . ?
C1" C10" C4A' C4" -12(2) . . . . ?
C10' C10" C4A' C4" 114.5(7) . . . . ?
C1' C10" C4A' C4B' -148.09(13) . . . . ?
C1" C10" C4A' C4B' -146(2) . . . . ?
C10' C10" C4A' C4B' -19.53(10) . . . . ?
C1' C10" C4A' C11' 88.01(15) . . . . ?
C1" C10" C4A' C11' 90(2) . . . . ?
C10' C10" C4A' C11' -143.43(9) . . . . ?
C1' C10" C4A' C4' -38.62(15) . . . . ?
C10' C10" C4A' C4' 89.94(10) . . . . ?
C3' C4' C4A' C4B' 152.71(9) . . . . ?
C3' C4' C4A' C11' -80.93(12) . . . . ?
C3' C4' C4A' C10" 46.05(12) . . . . ?

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
N5 H05 O1' 0.83(2) 1.95(2) 2.7654(12) 166(3) . yes
N5' H05' O1 0.84(2) 1.96(3) 2.7846(12) 167(3) 1_545 yes

_refine_diff_density_max         0.658
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_fremini
_database_code_depnum_ccdc_archive 'CCDC 2289676'
loop_
_audit_author_name
_audit_author_address
'Peter G. Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-08-20 deposited with the CCDC.	2023-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 N O2 S'
_chemical_formula_sum            'C23 H27 N O2 S'
_chemical_formula_weight         381.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'

_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+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   12.34580(14)
_cell_length_b                   27.6089(3)
_cell_length_c                   18.0509(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.9373(12)
_cell_angle_gamma                90
_cell_volume                     5916.24(12)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    69573
_cell_measurement_theta_min      2.9980
_cell_measurement_theta_max      79.2190

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             2448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.589
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100.03(12)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       '      ω scans'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            116565
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.007
_diffrn_reflns_theta_max         80.519
_diffrn_reflns_theta_full        77.500
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             12388
_reflns_number_gt                12162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_max     0.917
_reflns_Friedel_fraction_full    0.935

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0498P)²+2.6737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 The structure was refined as a 2-component inversion twin. The relative volume
 of the smaller component refined to 0.471(10).
;
_refine_ls_abs_structure_Flack   0.471(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         12388
_refine_ls_number_parameters     737
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
S1 S 0.41967(4) 0.84990(2) 0.53789(3) 0.01599(10) Uani 1 1 d . . . . .
O1 O 0.39827(13) 0.79932(6) 0.52305(9) 0.0205(3) Uani 1 1 d . . . . .
O2 O 0.52528(13) 0.87024(6) 0.53556(10) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.1180(2) 0.85901(8) 0.22515(13) 0.0213(4) Uani 1 1 d . . . . .
H1A H 0.103623 0.888367 0.192414 0.026 Uiso 1 1 calc R U . . .
H1B H 0.047926 0.839599 0.213436 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2126(2) 0.82931(8) 0.20768(14) 0.0233(5) Uani 1 1 d . . . . .
H2A H 0.278799 0.850444 0.211848 0.028 Uiso 1 1 calc R U . . .
H2B H 0.187269 0.817108 0.154114 0.028 Uiso 1 1 calc R U . . .
C3 C 0.24717(19) 0.78644(8) 0.26289(13) 0.0200(4) Uani 1 1 d . . . . .
H3A H 0.311788 0.769575 0.251857 0.024 Uiso 1 1 calc R U . . .
H3B H 0.183801 0.763207 0.253977 0.024 Uiso 1 1 calc R U . . .
C4 C 0.28014(17) 0.80248(7) 0.34798(12) 0.0166(4) Uani 1 1 d . . . . .
H4A H 0.298211 0.773633 0.381720 0.020 Uiso 1 1 calc R U . . .
H4B H 0.348104 0.823201 0.358502 0.020 Uiso 1 1 calc R U . . .
C4A C 0.18344(17) 0.83062(7) 0.36594(12) 0.0147(4) Uani 1 1 d . . . . .
C4B C 0.20594(16) 0.85652(7) 0.44505(12) 0.0148(4) Uani 1 1 d . . . . .
H4C H 0.190743 0.834407 0.484911 0.018 Uiso 1 1 calc R U . . .
N5 N 0.32094(14) 0.87904(6) 0.47282(10) 0.0152(3) Uani 1 1 d . . . . .
C5A C 0.31063(18) 0.93038(7) 0.47966(12) 0.0161(4) Uani 1 1 d . . . . .
C6 C 0.39589(19) 0.96453(8) 0.50359(13) 0.0199(4) Uani 1 1 d . . . . .
H6 H 0.472813 0.955088 0.519425 0.024 Uiso 1 1 calc R U . . .
C7 C 0.3647(2) 1.01320(8) 0.50360(14) 0.0238(5) Uani 1 1 d . . . . .
H7 H 0.421291 1.037168 0.520668 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2521(2) 1.02714(8) 0.47899(14) 0.0239(5) Uani 1 1 d . . . . .
H8 H 0.232495 1.060411 0.479140 0.029 Uiso 1 1 calc R U . . .
C9 C 0.1682(2) 0.99249(8) 0.45423(14) 0.0212(4) Uani 1 1 d . . . . .
H9 H 0.091496 1.001977 0.436336 0.025 Uiso 1 1 calc R U . . .
C9A C 0.19779(18) 0.94378(8) 0.45588(12) 0.0165(4) Uani 1 1 d . . . . .
C9B C 0.12256(17) 0.90068(7) 0.42954(13) 0.0168(4) Uani 1 1 d . . . . .
H9B H 0.064618 0.897630 0.458601 0.020 Uiso 1 1 calc R U . . .
C10 C 0.06799(18) 0.90202(8) 0.34126(13) 0.0197(4) Uani 1 1 d . . . . .
H10A H -0.006987 0.886322 0.327401 0.024 Uiso 1 1 calc R U . . .
H10B H 0.060113 0.935701 0.321690 0.024 Uiso 1 1 calc R U . . .
C10A C 0.15159(17) 0.87354(7) 0.30982(12) 0.0165(4) Uani 1 1 d . . . . .
H10C H 0.220526 0.894137 0.318129 0.020 Uiso 1 1 calc R U . . .
C11 C 0.40087(18) 0.86295(8) 0.62932(13) 0.0177(4) Uani 1 1 d . . . . .
C12 C 0.3256(2) 0.83539(9) 0.65654(14) 0.0238(5) Uani 1 1 d . . . . .
H12 H 0.283213 0.810279 0.625809 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3132(2) 0.84508(9) 0.72903(15) 0.0276(5) Uani 1 1 d . . . . .
H13 H 0.261315 0.826528 0.747619 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3754(2) 0.88164(9) 0.77547(14) 0.0247(5) Uani 1 1 d . . . . .
C15 C 0.4488(2) 0.90915(9) 0.74639(14) 0.0253(5) Uani 1 1 d . . . . .
H15 H 0.490448 0.934574 0.776746 0.030 Uiso 1 1 calc R U . . .
C16 C 0.46228(18) 0.90011(9) 0.67374(14) 0.0219(4) Uani 1 1 d . . . . .
H16 H 0.512870 0.919080 0.654595 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3633(3) 0.89039(11) 0.85515(15) 0.0340(6) Uani 1 1 d . . . . .
H17A H 0.422360 0.912682 0.882871 0.051 Uiso 1 1 calc R U . . .
H17B H 0.370451 0.859583 0.883060 0.051 Uiso 1 1 calc R U . . .
H17C H 0.289239 0.904585 0.851384 0.051 Uiso 1 1 calc R U . . .
C18 C 0.08316(18) 0.79643(8) 0.36162(14) 0.0203(4) Uani 1 1 d . . . . .
H18A H 0.044331 0.789669 0.307550 0.030 Uiso 1 1 calc R U . . .
H18B H 0.030675 0.811845 0.386404 0.030 Uiso 1 1 calc R U . . .
H18C H 0.110746 0.766027 0.388174 0.030 Uiso 1 1 calc R U . . .
S1' S 0.90839(4) 0.82371(2) 0.53368(3) 0.01623(10) Uani 1 1 d . . . . .
O1' O 0.88663(14) 0.86928(6) 0.49456(10) 0.0220(3) Uani 1 1 d . . . . .
O2' O 1.01686(13) 0.80146(6) 0.54657(10) 0.0224(3) Uani 1 1 d . . . . .
C1' C 0.6033(2) 0.76491(10) 0.22912(15) 0.0316(6) Uani 1 1 d . . . . .
H1A' H 0.537823 0.786741 0.210481 0.038 Uiso 1 1 calc R U . . .
H1B' H 0.580790 0.731965 0.209049 0.038 Uiso 1 1 calc R U . . .
C2' C 0.7023(3) 0.78277(10) 0.20041(16) 0.0346(6) Uani 1 1 d . . . . .
H2A' H 0.762798 0.758112 0.212551 0.041 Uiso 1 1 calc R U . . .
H2B' H 0.676857 0.786519 0.143715 0.041 Uiso 1 1 calc R U . . .
C3' C 0.7495(2) 0.83083(10) 0.23655(15) 0.0301(5) Uani 1 1 d . . . . .
H3A' H 0.693255 0.856634 0.216995 0.036 Uiso 1 1 calc R U . . .
H3B' H 0.817828 0.838833 0.220386 0.036 Uiso 1 1 calc R U . . .
C4' C 0.7799(2) 0.83016(9) 0.32535(14) 0.0240(5) Uani 1 1 d . . . . .
H4A' H 0.843875 0.807820 0.345632 0.029 Uiso 1 1 calc R U . . .
H4B' H 0.803513 0.862988 0.345462 0.029 Uiso 1 1 calc R U . . .
C4A' C 0.67945(18) 0.81390(8) 0.35313(13) 0.0184(4) Uani 1 1 d . . . . .
C4B' C 0.69877(17) 0.80371(7) 0.44045(13) 0.0165(4) Uani 1 1 d . . . . .
H4C' H 0.678936 0.832902 0.466810 0.020 Uiso 1 1 calc R U . . .
N5' N 0.81460(15) 0.78584(6) 0.48247(10) 0.0156(3) Uani 1 1 d . . . . .
C5A' C 0.80714(18) 0.73704(7) 0.50751(12) 0.0164(4) Uani 1 1 d . . . . .
C6' C 0.89430(19) 0.70692(8) 0.54593(13) 0.0212(4) Uani 1 1 d . . . . .
H6' H 0.969555 0.718444 0.563247 0.025 Uiso 1 1 calc R U . . .
C7' C 0.8674(2) 0.65906(8) 0.55824(14) 0.0254(5) Uani 1 1 d . . . . .
H7' H 0.925443 0.637703 0.584835 0.031 Uiso 1 1 calc R U . . .
C8' C 0.7577(2) 0.64198(8) 0.53247(14) 0.0262(5) Uani 1 1 d . . . . .
H8' H 0.741714 0.608966 0.539903 0.031 Uiso 1 1 calc R U . . .
C9' C 0.6712(2) 0.67330(8) 0.49568(13) 0.0225(5) Uani 1 1 d . . . . .
H9' H 0.595763 0.661984 0.478735 0.027 Uiso 1 1 calc R U . . .
C9A' C 0.69637(19) 0.72127(8) 0.48402(13) 0.0182(4) Uani 1 1 d . . . . .
C9B' C 0.61756(18) 0.76055(8) 0.44437(14) 0.0194(4) Uani 1 1 d . . . . .
H9B' H 0.563007 0.769535 0.474033 0.023 Uiso 1 1 calc R U . . .
C10' C 0.55656(19) 0.74744(8) 0.36007(15) 0.0239(5) Uani 1 1 d . . . . .
H10D H 0.542747 0.712152 0.353997 0.029 Uiso 1 1 calc R U . . .
H10E H 0.483929 0.764834 0.342083 0.029 Uiso 1 1 calc R U . . .
C01' C 0.63958(19) 0.76416(8) 0.31696(13) 0.0213(4) Uani 1 1 d . . . . .
H10F H 0.705946 0.741953 0.332557 0.026 Uiso 1 1 calc R U . . .
C11' C 0.88207(18) 0.83093(8) 0.62456(13) 0.0175(4) Uani 1 1 d . . . . .
C12' C 0.9534(2) 0.81081(8) 0.69050(14) 0.0235(5) Uani 1 1 d . . . . .
H12' H 1.016296 0.791953 0.687176 0.028 Uiso 1 1 calc R U . . .
C13' C 0.9326(2) 0.81836(9) 0.76112(14) 0.0269(5) Uani 1 1 d . . . . .
H13' H 0.982648 0.805045 0.806190 0.032 Uiso 1 1 calc R U . . .
C14' C 0.83966(19) 0.84512(8) 0.76759(14) 0.0212(4) Uani 1 1 d . . . . .
C15' C 0.7686(2) 0.86443(10) 0.70036(15) 0.0270(5) Uani 1 1 d . . . . .
H15' H 0.704558 0.882549 0.703333 0.032 Uiso 1 1 calc R U . . .
C16' C 0.7889(2) 0.85793(10) 0.62955(14) 0.0262(5) Uani 1 1 d . . . . .
H16' H 0.739825 0.871746 0.584560 0.031 Uiso 1 1 calc R U . . .
C17' C 0.8163(2) 0.85389(9) 0.84380(15) 0.0278(5) Uani 1 1 d . . . . .
H17D H 0.853094 0.828713 0.880371 0.042 Uiso 1 1 calc R U . . .
H17E H 0.734892 0.852979 0.837205 0.042 Uiso 1 1 calc R U . . .
H17F H 0.845832 0.885709 0.863590 0.042 Uiso 1 1 calc R U . . .
C18' C 0.5864(2) 0.85288(8) 0.33343(15) 0.0243(5) Uani 1 1 d . . . . .
H18D H 0.553349 0.854033 0.277509 0.037 Uiso 1 1 calc R U . . .
H18E H 0.619039 0.884522 0.351644 0.037 Uiso 1 1 calc R U . . .
H18F H 0.527813 0.844866 0.358628 0.037 Uiso 1 1 calc R U . . .
S1" S 0.09087(4) 0.51385(2) 0.45801(3) 0.01609(11) Uani 1 1 d . . . . .
O1" O 0.11136(14) 0.46442(6) 0.48165(10) 0.0225(3) Uani 1 1 d . . . . .
O2" O -0.01700(13) 0.53501(6) 0.45179(10) 0.0217(3) Uani 1 1 d . . . . .
C1" C 0.4031(2) 0.53725(8) 0.76931(13) 0.0224(5) Uani 1 1 d . . . . .
H1A" H 0.419387 0.567574 0.799605 0.027 Uiso 1 1 calc R U . . .
H1B" H 0.473200 0.517920 0.780127 0.027 Uiso 1 1 calc R U . . .
C2" C 0.3116(2) 0.50853(8) 0.79293(15) 0.0258(5) Uani 1 1 d . . . . .
H2A" H 0.341720 0.497493 0.846862 0.031 Uiso 1 1 calc R U . . .
H2B" H 0.246802 0.530145 0.790769 0.031 Uiso 1 1 calc R U . . .
C3" C 0.27064(19) 0.46458(8) 0.74143(13) 0.0192(4) Uani 1 1 d . . . . .
H3A" H 0.206472 0.449553 0.755817 0.023 Uiso 1 1 calc R U . . .
H3B" H 0.331994 0.440356 0.750242 0.023 Uiso 1 1 calc R U . . .
C4" C 0.23368(17) 0.47800(7) 0.65573(13) 0.0162(4) Uani 1 1 d . . . . .
H4A" H 0.212592 0.448284 0.624400 0.019 Uiso 1 1 calc R U . . .
H4B" H 0.166720 0.499327 0.645454 0.019 Uiso 1 1 calc R U . . .
C4A" C 0.32896(17) 0.50401(7) 0.63268(13) 0.0141(4) Uani 1 1 d . . . . .
C4B" C 0.30221(17) 0.52608(8) 0.55047(13) 0.0151(4) Uani 1 1 d . . . . .
H4C" H 0.318189 0.502195 0.513168 0.018 Uiso 1 1 calc R U . . .
N5" N 0.18515(15) 0.54642(6) 0.52092(11) 0.0162(4) Uani 1 1 d . . . . .
C5A" C 0.19169(18) 0.59777(8) 0.51001(12) 0.0165(4) Uani 1 1 d . . . . .
C6" C 0.1034(2) 0.63035(8) 0.48569(14) 0.0217(4) Uani 1 1 d . . . . .
H6" H 0.027233 0.619820 0.472509 0.026 Uiso 1 1 calc R U . . .
C7" C 0.1306(2) 0.67912(8) 0.48132(14) 0.0241(5) Uani 1 1 d . . . . .
H7" H 0.071856 0.702077 0.463664 0.029 Uiso 1 1 calc R U . . .
C8" C 0.2423(2) 0.69489(9) 0.50232(14) 0.0238(5) Uani 1 1 d . . . . .
H8" H 0.259067 0.728281 0.499074 0.029 Uiso 1 1 calc R U . . .
C9" C 0.3288(2) 0.66170(8) 0.52794(13) 0.0210(4) Uani 1 1 d . . . . .
H9" H 0.404891 0.672298 0.543315 0.025 Uiso 1 1 calc R U . . .
C9A" C 0.30344(18) 0.61277(8) 0.53102(12) 0.0171(4) Uani 1 1 d . . . . .
C9B" C 0.38251(18) 0.57127(8) 0.55925(13) 0.0170(4) Uani 1 1 d . . . . .
H9B" H 0.437649 0.567507 0.528122 0.020 Uiso 1 1 calc R U . . .
C10" C 0.44268(19) 0.57592(8) 0.64631(13) 0.0193(4) Uani 1 1 d . . . . .
H10G H 0.517909 0.560465 0.659261 0.023 Uiso 1 1 calc R U . . .
H10H H 0.451125 0.610292 0.662502 0.023 Uiso 1 1 calc R U . . .
C01" C 0.36332(17) 0.54916(7) 0.68384(13) 0.0156(4) Uani 1 1 d . . . . .
H10I H 0.294308 0.569645 0.676059 0.019 Uiso 1 1 calc R U . . .
C11" C 0.11855(19) 0.51978(8) 0.36759(13) 0.0178(4) Uani 1 1 d . . . . .
C12" C 0.1994(2) 0.49052(9) 0.34952(15) 0.0244(5) Uani 1 1 d . . . . .
H12" H 0.240463 0.467617 0.385755 0.029 Uiso 1 1 calc R U . . .
C13" C 0.2193(2) 0.49521(10) 0.27805(16) 0.0298(5) Uani 1 1 d . . . . .
H13" H 0.275298 0.475636 0.265877 0.036 Uiso 1 1 calc R U . . .
C14" C 0.1587(2) 0.52812(10) 0.22338(15) 0.0296(5) Uani 1 1 d . . . . .
C15" C 0.0782(2) 0.55690(10) 0.24291(15) 0.0303(5) Uani 1 1 d . . . . .
H15" H 0.036104 0.579418 0.206410 0.036 Uiso 1 1 calc R U . . .
C16" C 0.0583(2) 0.55335(9) 0.31431(14) 0.0236(5) Uani 1 1 d . . . . .
H16" H 0.003950 0.573649 0.327081 0.028 Uiso 1 1 calc R U . . .
C17" C 0.1789(3) 0.53234(14) 0.14488(17) 0.0434(7) Uani 1 1 d . . . . .
H17G H 0.251458 0.517509 0.146048 0.065 Uiso 1 1 calc R U . . .
H17H H 0.179832 0.566601 0.130882 0.065 Uiso 1 1 calc R U . . .
H17I H 0.118496 0.515649 0.106740 0.065 Uiso 1 1 calc R U . . .
C18" C 0.42785(18) 0.46915(8) 0.63789(14) 0.0198(4) Uani 1 1 d . . . . .
H18G H 0.399487 0.438870 0.611247 0.030 Uiso 1 1 calc R U . . .
H18H H 0.465556 0.462305 0.692118 0.030 Uiso 1 1 calc R U . . .
H18I H 0.481567 0.484054 0.613622 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4309(17) . ?
S1 O1 1.4326(16) . ?
S1 N5 1.6512(18) . ?
S1 C11 1.766(2) . ?
C1 C10A 1.523(3) . ?
C1 C2 1.529(3) . ?
C2 C3 1.531(3) . ?
C3 C4 1.542(3) . ?
C4 C4A 1.532(3) . ?
C4A C10A 1.538(3) . ?
C4A C18 1.542(3) . ?
C4A C4B 1.552(3) . ?
C4B N5 1.504(2) . ?
C4B C9B 1.570(3) . ?
N5 C5A 1.431(3) . ?
C5A C9A 1.390(3) . ?
C5A C6 1.391(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.393(4) . ?
C8 C9 1.390(3) . ?
C9 C9A 1.392(3) . ?
C9A C9B 1.504(3) . ?
C9B C10 1.551(3) . ?
C10 C10A 1.525(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.391(3) . ?
C12 C13 1.385(4) . ?
C13 C14 1.400(4) . ?
C14 C15 1.391(4) . ?
C14 C17 1.506(3) . ?
C15 C16 1.389(4) . ?
S1' O1' 1.4316(16) . ?
S1' O2' 1.4331(16) . ?
S1' N5' 1.6433(18) . ?
S1' C11' 1.769(2) . ?
C1' C01' 1.525(3) . ?
C1' C2' 1.534(4) . ?
C2' C3' 1.522(4) . ?
C3' C4' 1.543(3) . ?
C4' C4A' 1.527(3) . ?
C4A' C01' 1.542(3) . ?
C4A' C18' 1.542(3) . ?
C4A' C4B' 1.554(3) . ?
C4B' N5' 1.506(3) . ?
C4B' C9B' 1.571(3) . ?
N5' C5A' 1.432(3) . ?
C5A' C6' 1.386(3) . ?
C5A' C9A' 1.386(3) . ?
C6' C7' 1.395(3) . ?
C7' C8' 1.388(4) . ?
C8' C9' 1.393(3) . ?
C9' C9A' 1.389(3) . ?
C9A' C9B' 1.501(3) . ?
C9B' C10' 1.544(3) . ?
C10' C01' 1.519(3) . ?
C11' C12' 1.388(3) . ?
C11' C16' 1.394(3) . ?
C12' C13' 1.384(4) . ?
C13' C14' 1.397(3) . ?
C14' C15' 1.393(3) . ?
C14' C17' 1.500(3) . ?
C15' C16' 1.380(4) . ?
S1" O2" 1.4302(17) . ?
S1" O1" 1.4314(17) . ?
S1" N5" 1.6514(18) . ?
S1" C11" 1.765(2) . ?
C1" C01" 1.521(3) . ?
C1" C2" 1.533(3) . ?
C2" C3" 1.528(3) . ?
C3" C4" 1.533(3) . ?
C4" C4A" 1.530(3) . ?
C4A" C18" 1.537(3) . ?
C4A" C01" 1.540(3) . ?
C4A" C4B" 1.553(3) . ?
C4B" N5" 1.505(3) . ?
C4B" C9B" 1.574(3) . ?
N5" C5A" 1.437(3) . ?
C5A" C6" 1.388(3) . ?
C5A" C9A" 1.390(3) . ?
C6" C7" 1.395(3) . ?
C7" C8" 1.396(3) . ?
C8" C9" 1.386(4) . ?
C9" C9A" 1.391(3) . ?
C9A" C9B" 1.501(3) . ?
C9B" C10" 1.548(3) . ?
C10" C01" 1.526(3) . ?
C11" C12" 1.391(3) . ?
C11" C16" 1.394(3) . ?
C12" C13" 1.384(4) . ?
C13" C14" 1.398(4) . ?
C14" C15" 1.391(4) . ?
C14" C17" 1.509(4) . ?
C15" C16" 1.380(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
O2 S1 O1 119.99(10) . . ?
O2 S1 N5 106.76(10) . . ?
O1 S1 N5 106.24(9) . . ?
O2 S1 C11 107.57(10) . . ?
O1 S1 C11 108.00(10) . . ?
N5 S1 C11 107.74(10) . . ?
C10A C1 C2 109.60(18) . . ?
C1 C2 C3 111.9(2) . . ?
C2 C3 C4 112.13(18) . . ?
C4A C4 C3 110.40(17) . . ?
C4 C4A C10A 108.94(18) . . ?
C4 C4A C18 109.89(17) . . ?
C10A C4A C18 112.45(17) . . ?
C4 C4A C4B 118.38(16) . . ?
C10A C4A C4B 101.52(16) . . ?
C18 C4A C4B 105.49(18) . . ?
N5 C4B C4A 114.27(17) . . ?
N5 C4B C9B 104.55(16) . . ?
C4A C4B C9B 104.52(16) . . ?
C5A N5 C4B 109.86(16) . . ?
C5A N5 S1 119.14(14) . . ?
C4B N5 S1 118.72(14) . . ?
C9A C5A C6 121.6(2) . . ?
C9A C5A N5 110.01(18) . . ?
C6 C5A N5 128.4(2) . . ?
C5A C6 C7 117.8(2) . . ?
C8 C7 C6 121.1(2) . . ?
C9 C8 C7 120.2(2) . . ?
C8 C9 C9A 119.4(2) . . ?
C5A C9A C9 119.9(2) . . ?
C5A C9A C9B 111.50(18) . . ?
C9 C9A C9B 128.5(2) . . ?
C9A C9B C10 111.24(18) . . ?
C9A C9B C4B 103.90(16) . . ?
C10 C9B C4B 106.27(17) . . ?
C10A C10 C9B 102.86(16) . . ?
C1 C10A C10 118.91(18) . . ?
C1 C10A C4A 114.06(17) . . ?
C10 C10A C4A 103.22(18) . . ?
C12 C11 C16 120.7(2) . . ?
C12 C11 S1 119.37(17) . . ?
C16 C11 S1 119.90(18) . . ?
C13 C12 C11 119.1(2) . . ?
C12 C13 C14 121.4(2) . . ?
C15 C14 C13 118.4(2) . . ?
C15 C14 C17 121.2(2) . . ?
C13 C14 C17 120.4(2) . . ?
C16 C15 C14 121.2(2) . . ?
C15 C16 C11 119.3(2) . . ?
O1' S1' O2' 119.82(10) . . ?
O1' S1' N5' 105.89(10) . . ?
O2' S1' N5' 107.54(9) . . ?
O1' S1' C11' 107.51(10) . . ?
O2' S1' C11' 107.41(10) . . ?
N5' S1' C11' 108.23(10) . . ?
C01' C1' C2' 108.8(2) . . ?
C3' C2' C1' 112.5(2) . . ?
C2' C3' C4' 113.0(2) . . ?
C4A' C4' C3' 110.9(2) . . ?
C4' C4A' C01' 108.45(19) . . ?
C4' C4A' C18' 109.84(19) . . ?
C01' C4A' C18' 113.13(18) . . ?
C4' C4A' C4B' 118.30(18) . . ?
C01' C4A' C4B' 102.15(17) . . ?
C18' C4A' C4B' 104.92(18) . . ?
N5' C4B' C4A' 115.49(17) . . ?
N5' C4B' C9B' 104.97(16) . . ?
C4A' C4B' C9B' 105.12(17) . . ?
C5A' N5' C4B' 109.43(16) . . ?
C5A' N5' S1' 121.16(14) . . ?
C4B' N5' S1' 119.99(14) . . ?
C6' C5A' C9A' 122.0(2) . . ?
C6' C5A' N5' 127.9(2) . . ?
C9A' C5A' N5' 110.03(18) . . ?
C5A' C6' C7' 117.5(2) . . ?
C8' C7' C6' 121.4(2) . . ?
C7' C8' C9' 119.9(2) . . ?
C9A' C9' C8' 119.3(2) . . ?
C5A' C9A' C9' 119.7(2) . . ?
C5A' C9A' C9B' 112.02(18) . . ?
C9' C9A' C9B' 128.2(2) . . ?
C9A' C9B' C10' 112.18(19) . . ?
C9A' C9B' C4B' 103.37(17) . . ?
C10' C9B' C4B' 106.14(18) . . ?
C01' C10' C9B' 102.62(18) . . ?
C10' C01' C1' 119.3(2) . . ?
C10' C01' C4A' 103.63(19) . . ?
C1' C01' C4A' 113.38(19) . . ?
C12' C11' C16' 120.0(2) . . ?
C12' C11' S1' 121.01(18) . . ?
C16' C11' S1' 119.02(17) . . ?
C13' C12' C11' 119.7(2) . . ?
C12' C13' C14' 121.4(2) . . ?
C15' C14' C13' 117.7(2) . . ?
C15' C14' C17' 120.2(2) . . ?
C13' C14' C17' 122.1(2) . . ?
C16' C15' C14' 121.7(2) . . ?
C15' C16' C11' 119.5(2) . . ?
O2" S1" O1" 119.83(10) . . ?
O2" S1" N5" 107.27(10) . . ?
O1" S1" N5" 106.30(10) . . ?
O2" S1" C11" 107.58(10) . . ?
O1" S1" C11" 107.51(11) . . ?
N5" S1" C11" 107.85(10) . . ?
C01" C1" C2" 109.69(19) . . ?
C3" C2" C1" 112.8(2) . . ?
C2" C3" C4" 112.27(18) . . ?
C4A" C4" C3" 110.48(17) . . ?
C4" C4A" C18" 110.28(17) . . ?
C4" C4A" C01" 108.81(18) . . ?
C18" C4A" C01" 112.75(17) . . ?
C4" C4A" C4B" 117.79(17) . . ?
C18" C4A" C4B" 105.13(18) . . ?
C01" C4A" C4B" 101.94(16) . . ?
N5" C4B" C4A" 114.61(18) . . ?
N5" C4B" C9B" 104.88(16) . . ?
C4A" C4B" C9B" 104.58(16) . . ?
C5A" N5" C4B" 109.40(16) . . ?
C5A" N5" S1" 119.91(15) . . ?
C4B" N5" S1" 117.87(14) . . ?
C6" C5A" C9A" 121.8(2) . . ?
C6" C5A" N5" 127.9(2) . . ?
C9A" C5A" N5" 110.23(18) . . ?
C5A" C6" C7" 117.6(2) . . ?
C6" C7" C8" 121.4(2) . . ?
C9" C8" C7" 119.8(2) . . ?
C8" C9" C9A" 119.6(2) . . ?
C5A" C9A" C9" 119.7(2) . . ?
C5A" C9A" C9B" 111.68(18) . . ?
C9" C9A" C9B" 128.5(2) . . ?
C9A" C9B" C10" 111.56(18) . . ?
C9A" C9B" C4B" 103.77(17) . . ?
C10" C9B" C4B" 106.34(17) . . ?
C01" C10" C9B" 102.88(17) . . ?
C1" C01" C10" 119.17(18) . . ?
C1" C01" C4A" 113.11(17) . . ?
C10" C01" C4A" 103.32(17) . . ?
C12" C11" C16" 120.4(2) . . ?
C12" C11" S1" 119.79(19) . . ?
C16" C11" S1" 119.84(18) . . ?
C13" C12" C11" 119.1(2) . . ?
C12" C13" C14" 121.5(2) . . ?
C15" C14" C13" 118.2(2) . . ?
C15" C14" C17" 120.5(3) . . ?
C13" C14" C17" 121.3(3) . . ?
C16" C15" C14" 121.2(2) . . ?
C15" C16" C11" 119.6(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
C10A C1 C2 C3 53.1(2) . . . . ?
C1 C2 C3 C4 -55.1(2) . . . . ?
C2 C3 C4 C4A 56.4(2) . . . . ?
C3 C4 C4A C10A -55.8(2) . . . . ?
C3 C4 C4A C18 67.8(2) . . . . ?
C3 C4 C4A C4B -171.02(17) . . . . ?
C4 C4A C4B N5 37.7(2) . . . . ?
C10A C4A C4B N5 -81.39(19) . . . . ?
C18 C4A C4B N5 161.17(16) . . . . ?
C4 C4A C4B C9B 151.39(17) . . . . ?
C10A C4A C4B C9B 32.28(19) . . . . ?
C18 C4A C4B C9B -85.17(19) . . . . ?
C4A C4B N5 C5A 117.68(19) . . . . ?
C9B C4B N5 C5A 4.0(2) . . . . ?
C4A C4B N5 S1 -100.31(18) . . . . ?
C9B C4B N5 S1 146.04(15) . . . . ?
O2 S1 N5 C5A -59.60(18) . . . . ?
O1 S1 N5 C5A 171.24(16) . . . . ?
C11 S1 N5 C5A 55.70(18) . . . . ?
O2 S1 N5 C4B 161.91(15) . . . . ?
O1 S1 N5 C4B 32.75(18) . . . . ?
C11 S1 N5 C4B -82.79(17) . . . . ?
C4B N5 C5A C9A -2.2(2) . . . . ?
S1 N5 C5A C9A -143.99(16) . . . . ?
C4B N5 C5A C6 179.7(2) . . . . ?
S1 N5 C5A C6 37.9(3) . . . . ?
C9A C5A C6 C7 0.4(3) . . . . ?
N5 C5A C6 C7 178.4(2) . . . . ?
C5A C6 C7 C8 -1.2(4) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C9A 1.4(4) . . . . ?
C6 C5A C9A C9 1.3(3) . . . . ?
N5 C5A C9A C9 -177.0(2) . . . . ?
C6 C5A C9A C9B 177.4(2) . . . . ?
N5 C5A C9A C9B -0.8(3) . . . . ?
C8 C9 C9A C5A -2.2(3) . . . . ?
C8 C9 C9A C9B -177.6(2) . . . . ?
C5A C9A C9B C10 -110.7(2) . . . . ?
C9 C9A C9B C10 65.0(3) . . . . ?
C5A C9A C9B C4B 3.2(2) . . . . ?
C9 C9A C9B C4B 179.0(2) . . . . ?
N5 C4B C9B C9A -4.2(2) . . . . ?
C4A C4B C9B C9A -124.63(18) . . . . ?
N5 C4B C9B C10 113.21(18) . . . . ?
C4A C4B C9B C10 -7.2(2) . . . . ?
C9A C9B C10 C10A 91.4(2) . . . . ?
C4B C9B C10 C10A -21.0(2) . . . . ?
C2 C1 C10A C10 -177.83(19) . . . . ?
C2 C1 C10A C4A -55.6(2) . . . . ?
C9B C10 C10A C1 169.37(18) . . . . ?
C9B C10 C10A C4A 41.91(19) . . . . ?
C4 C4A C10A C1 57.4(2) . . . . ?
C18 C4A C10A C1 -64.7(2) . . . . ?
C4B C4A C10A C1 -176.93(17) . . . . ?
C4 C4A C10A C10 -172.13(16) . . . . ?
C18 C4A C10A C10 65.8(2) . . . . ?
C4B C4A C10A C10 -46.48(19) . . . . ?
O2 S1 C11 C12 -159.81(18) . . . . ?
O1 S1 C11 C12 -28.9(2) . . . . ?
N5 S1 C11 C12 85.43(19) . . . . ?
O2 S1 C11 C16 19.4(2) . . . . ?
O1 S1 C11 C16 150.22(17) . . . . ?
N5 S1 C11 C16 -95.40(19) . . . . ?
C16 C11 C12 C13 -0.7(3) . . . . ?
S1 C11 C12 C13 178.50(19) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C12 C13 C14 C17 -177.9(2) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C17 C14 C15 C16 178.1(2) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
C12 C11 C16 C15 0.8(3) . . . . ?
S1 C11 C16 C15 -178.34(17) . . . . ?
C01' C1' C2' C3' -53.1(3) . . . . ?
C1' C2' C3' C4' 52.7(3) . . . . ?
C2' C3' C4' C4A' -54.0(3) . . . . ?
C3' C4' C4A' C01' 55.6(2) . . . . ?
C3' C4' C4A' C18' -68.5(3) . . . . ?
C3' C4' C4A' C4B' 171.17(19) . . . . ?
C4' C4A' C4B' N5' -30.2(3) . . . . ?
C01' C4A' C4B' N5' 88.7(2) . . . . ?
C18' C4A' C4B' N5' -153.09(18) . . . . ?
C4' C4A' C4B' C9B' -145.41(19) . . . . ?
C01' C4A' C4B' C9B' -26.5(2) . . . . ?
C18' C4A' C4B' C9B' 91.75(19) . . . . ?
C4A' C4B' N5' C5A' -113.70(19) . . . . ?
C9B' C4B' N5' C5A' 1.6(2) . . . . ?
C4A' C4B' N5' S1' 99.46(19) . . . . ?
C9B' C4B' N5' S1' -145.29(15) . . . . ?
O1' S1' N5' C5A' -176.15(17) . . . . ?
O2' S1' N5' C5A' 54.64(19) . . . . ?
C11' S1' N5' C5A' -61.11(19) . . . . ?
O1' S1' N5' C4B' -33.22(19) . . . . ?
O2' S1' N5' C4B' -162.43(16) . . . . ?
C11' S1' N5' C4B' 81.82(18) . . . . ?
C4B' N5' C5A' C6' 177.8(2) . . . . ?
S1' N5' C5A' C6' -35.8(3) . . . . ?
C4B' N5' C5A' C9A' 1.2(2) . . . . ?
S1' N5' C5A' C9A' 147.54(16) . . . . ?
C9A' C5A' C6' C7' 2.1(3) . . . . ?
N5' C5A' C6' C7' -174.2(2) . . . . ?
C5A' C6' C7' C8' 0.6(4) . . . . ?
C6' C7' C8' C9' -2.2(4) . . . . ?
C7' C8' C9' C9A' 1.1(4) . . . . ?
C6' C5A' C9A' C9' -3.1(3) . . . . ?
N5' C5A' C9A' C9' 173.8(2) . . . . ?
C6' C5A' C9A' C9B' 179.5(2) . . . . ?
N5' C5A' C9A' C9B' -3.6(3) . . . . ?
C8' C9' C9A' C5A' 1.4(3) . . . . ?
C8' C9' C9A' C9B' 178.4(2) . . . . ?
C5A' C9A' C9B' C10' 118.3(2) . . . . ?
C9' C9A' C9B' C10' -58.9(3) . . . . ?
C5A' C9A' C9B' C4B' 4.4(2) . . . . ?
C9' C9A' C9B' C4B' -172.8(2) . . . . ?
N5' C4B' C9B' C9A' -3.4(2) . . . . ?
C4A' C4B' C9B' C9A' 118.85(18) . . . . ?
N5' C4B' C9B' C10' -121.62(18) . . . . ?
C4A' C4B' C9B' C10' 0.6(2) . . . . ?
C9A' C9B' C10' C01' -86.3(2) . . . . ?
C4B' C9B' C10' C01' 25.9(2) . . . . ?
C9B' C10' C01' C1' -170.51(19) . . . . ?
C9B' C10' C01' C4A' -43.3(2) . . . . ?
C2' C1' C01' C10' -179.6(2) . . . . ?
C2' C1' C01' C4A' 57.9(3) . . . . ?
C4' C4A' C01' C10' 169.34(17) . . . . ?
C18' C4A' C01' C10' -68.6(2) . . . . ?
C4B' C4A' C01' C10' 43.7(2) . . . . ?
C4' C4A' C01' C1' -59.8(2) . . . . ?
C18' C4A' C01' C1' 62.3(3) . . . . ?
C4B' C4A' C01' C1' 174.5(2) . . . . ?
O1' S1' C11' C12' -138.14(19) . . . . ?
O2' S1' C11' C12' -7.9(2) . . . . ?
N5' S1' C11' C12' 107.89(19) . . . . ?
O1' S1' C11' C16' 40.9(2) . . . . ?
O2' S1' C11' C16' 171.07(18) . . . . ?
N5' S1' C11' C16' -73.1(2) . . . . ?
C16' C11' C12' C13' -1.0(4) . . . . ?
S1' C11' C12' C13' 177.98(19) . . . . ?
C11' C12' C13' C14' 1.3(4) . . . . ?
C12' C13' C14' C15' -0.5(4) . . . . ?
C12' C13' C14' C17' -179.6(2) . . . . ?
C13' C14' C15' C16' -0.5(4) . . . . ?
C17' C14' C15' C16' 178.6(2) . . . . ?
C14' C15' C16' C11' 0.7(4) . . . . ?
C12' C11' C16' C15' 0.0(4) . . . . ?
S1' C11' C16' C15' -179.0(2) . . . . ?
C01" C1" C2" C3" 51.8(3) . . . . ?
C1" C2" C3" C4" -52.9(3) . . . . ?
C2" C3" C4" C4A" 55.6(2) . . . . ?
C3" C4" C4A" C18" 66.8(2) . . . . ?
C3" C4" C4A" C01" -57.3(2) . . . . ?
C3" C4" C4A" C4B" -172.56(18) . . . . ?
C4" C4A" C4B" N5" 35.1(3) . . . . ?
C18" C4A" C4B" N5" 158.38(17) . . . . ?
C01" C4A" C4B" N5" -83.8(2) . . . . ?
C4" C4A" C4B" C9B" 149.41(18) . . . . ?
C18" C4A" C4B" C9B" -87.35(19) . . . . ?
C01" C4A" C4B" C9B" 30.5(2) . . . . ?
C4A" C4B" N5" C5A" 115.89(19) . . . . ?
C9B" C4B" N5" C5A" 1.8(2) . . . . ?
C4A" C4B" N5" S1" -102.47(19) . . . . ?
C9B" C4B" N5" S1" 143.44(15) . . . . ?
O2" S1" N5" C5A" -54.92(19) . . . . ?
O1" S1" N5" C5A" 175.77(17) . . . . ?
C11" S1" N5" C5A" 60.71(19) . . . . ?
O2" S1" N5" C4B" 167.55(15) . . . . ?
O1" S1" N5" C4B" 38.24(19) . . . . ?
C11" S1" N5" C4B" -76.82(18) . . . . ?
C4B" N5" C5A" C6" -178.1(2) . . . . ?
S1" N5" C5A" C6" 41.2(3) . . . . ?
C4B" N5" C5A" C9A" -0.8(2) . . . . ?
S1" N5" C5A" C9A" -141.55(16) . . . . ?
C9A" C5A" C6" C7" 1.4(4) . . . . ?
N5" C5A" C6" C7" 178.3(2) . . . . ?
C5A" C6" C7" C8" -1.5(4) . . . . ?
C6" C7" C8" C9" 0.2(4) . . . . ?
C7" C8" C9" C9A" 1.3(4) . . . . ?
C6" C5A" C9A" C9" 0.1(3) . . . . ?
N5" C5A" C9A" C9" -177.4(2) . . . . ?
C6" C5A" C9A" C9B" 176.8(2) . . . . ?
N5" C5A" C9A" C9B" -0.6(3) . . . . ?
C8" C9" C9A" C5A" -1.4(3) . . . . ?
C8" C9" C9A" C9B" -177.6(2) . . . . ?
C5A" C9A" C9B" C10" -112.4(2) . . . . ?
C9" C9A" C9B" C10" 64.0(3) . . . . ?
C5A" C9A" C9B" C4B" 1.7(2) . . . . ?
C9" C9A" C9B" C4B" 178.1(2) . . . . ?
N5" C4B" C9B" C9A" -2.0(2) . . . . ?
C4A" C4B" C9B" C9A" -122.99(18) . . . . ?
N5" C4B" C9B" C10" 115.75(19) . . . . ?
C4A" C4B" C9B" C10" -5.2(2) . . . . ?
C9A" C9B" C10" C01" 90.1(2) . . . . ?
C4B" C9B" C10" C01" -22.4(2) . . . . ?
C2" C1" C01" C10" -177.47(19) . . . . ?
C2" C1" C01" C4A" -55.8(2) . . . . ?
C9B" C10" C01" C1" 168.56(18) . . . . ?
C9B" C10" C01" C4A" 42.1(2) . . . . ?
C4" C4A" C01" C1" 59.2(2) . . . . ?
C18" C4A" C01" C1" -63.5(2) . . . . ?
C4B" C4A" C01" C1" -175.69(18) . . . . ?
C4" C4A" C01" C10" -170.61(16) . . . . ?
C18" C4A" C01" C10" 66.7(2) . . . . ?
C4B" C4A" C01" C10" -45.48(19) . . . . ?
O2" S1" C11" C12" -160.87(18) . . . . ?
O1" S1" C11" C12" -30.5(2) . . . . ?
N5" S1" C11" C12" 83.71(19) . . . . ?
O2" S1" C11" C16" 18.4(2) . . . . ?
O1" S1" C11" C16" 148.69(18) . . . . ?
N5" S1" C11" C16" -97.06(19) . . . . ?
C16" C11" C12" C13" 0.0(3) . . . . ?
S1" C11" C12" C13" 179.27(18) . . . . ?
C11" C12" C13" C14" -1.0(4) . . . . ?
C12" C13" C14" C15" 0.9(4) . . . . ?
C12" C13" C14" C17" -178.7(2) . . . . ?
C13" C14" C15" C16" 0.1(4) . . . . ?
C17" C14" C15" C16" 179.7(2) . . . . ?
C14" C15" C16" C11" -1.1(4) . . . . ?
C12" C11" C16" C15" 1.0(4) . . . . ?
S1" C11" C16" C15" -178.24(19) . . . . ?

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
C9B H9B O1' 1.00 2.58 3.534(3) 160.0 1_455 yes
C9B' H9B' O1 1.00 2.57 3.550(3) 168.1 . yes
C16' H16' O2 0.95 2.55 3.249(3) 130.4 . yes
C9B" H9B" O1" 1.00 2.66 3.618(3) 160.8 2_565 yes

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.040

