# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 2159993'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_audit_creation_date             2022-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H32 F4 N O2 Rh S'
_chemical_formula_sum            'C29 H32 F4 N O2 Rh S'
_chemical_formula_weight         637.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.8702(10)
_cell_length_b                   14.0428(12)
_cell_length_c                   18.3564(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2802.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1494 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.8081.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.993
_diffrn_reflns_theta_min         1.826
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6433
_reflns_number_total             6771
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 2732 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.031(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         6771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+0.2673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0631
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C13(H13), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Rh1 Rh 0.30868(2) 0.48604(2) 0.50696(2) 0.03459(7) Uani 1 1 d . . . . .
S1 S 0.27792(8) 0.71953(6) 0.52435(5) 0.0504(2) Uani 1 1 d . . . . .
F1 F 0.82651(18) 0.43702(19) 0.45715(12) 0.0659(6) Uani 1 1 d . . . . .
F2 F 0.9105(2) 0.3737(2) 0.32780(13) 0.0738(7) Uani 1 1 d . . . . .
F3 F 0.7539(2) 0.31873(19) 0.22263(12) 0.0676(6) Uani 1 1 d . . . . .
F4 F 0.5077(2) 0.33292(17) 0.24359(11) 0.0599(6) Uani 1 1 d . . . . .
O1 O 0.1844(2) 0.40844(15) 0.56435(12) 0.0467(5) Uani 1 1 d . . . . .
O2 O 0.1768(3) 0.78919(18) 0.5184(2) 0.0793(9) Uani 1 1 d . . . . .
N1 N 0.2140(2) 0.60754(18) 0.53695(15) 0.0403(6) Uani 1 1 d . . . . .
C1 C 0.3789(3) 0.3641(2) 0.45386(16) 0.0367(6) Uani 1 1 d . . . . .
H1 H 0.3331 0.3024 0.4560 0.044 Uiso 1 1 calc R U . . .
C2 C 0.4595(3) 0.3891(2) 0.50936(16) 0.0380(6) Uani 1 1 d . . . . .
C3 C 0.5563(3) 0.4623(2) 0.48343(16) 0.0387(6) Uani 1 1 d . . . . .
H3 H 0.6145 0.4824 0.5227 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4692(3) 0.5418(2) 0.45908(16) 0.0392(6) Uani 1 1 d . . . . .
H4 H 0.4920 0.6102 0.4661 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3879(3) 0.5152(2) 0.40426(15) 0.0381(6) Uani 1 1 d . . . . .
C6 C 0.4053(3) 0.4109(2) 0.38114(16) 0.0372(6) Uani 1 1 d . . . . .
H6 H 0.3473 0.3906 0.3418 0.045 Uiso 1 1 calc R U . . .
C7 C 0.6204(3) 0.4228(2) 0.41653(17) 0.0386(7) Uani 1 1 d . . . . .
C8 C 0.7452(3) 0.4136(3) 0.40497(19) 0.0463(8) Uani 1 1 d . . . . .
C9 C 0.7890(3) 0.3798(3) 0.33944(19) 0.0493(8) Uani 1 1 d . . . . .
C10 C 0.7100(3) 0.3535(3) 0.28560(17) 0.0488(8) Uani 1 1 d . . . . .
C11 C 0.5846(3) 0.3616(2) 0.29665(17) 0.0422(7) Uani 1 1 d . . . . .
C12 C 0.5398(3) 0.3960(2) 0.36127(17) 0.0377(6) Uani 1 1 d . . . . .
C13 C 0.4766(3) 0.3302(3) 0.57791(19) 0.0486(8) Uani 1 1 d . . . . .
H13 H 0.4044 0.2864 0.5819 0.058 Uiso 1 1 calc R U . . .
C14 C 0.5913(4) 0.2688(3) 0.5690(2) 0.0633(10) Uani 1 1 d . . . . .
H14A H 0.5814 0.2271 0.5266 0.095 Uiso 1 1 calc R U . . .
H14B H 0.6030 0.2299 0.6129 0.095 Uiso 1 1 calc R U . . .
H14C H 0.6632 0.3098 0.5619 0.095 Uiso 1 1 calc R U . . .
C15 C 0.4815(5) 0.3883(4) 0.6469(2) 0.0711(13) Uani 1 1 d . . . . .
H15A H 0.5429 0.4389 0.6416 0.107 Uiso 1 1 calc R U . . .
H15B H 0.5042 0.3470 0.6878 0.107 Uiso 1 1 calc R U . . .
H15C H 0.4006 0.4166 0.6561 0.107 Uiso 1 1 calc R U . . .
C16 C 0.3218(4) 0.5821(3) 0.35313(18) 0.0555(9) Uani 1 1 d . . . . .
H16 H 0.3169 0.6459 0.3772 0.067 Uiso 1 1 calc R U . . .
C17 C 0.1916(4) 0.5498(4) 0.3362(3) 0.0932(17) Uani 1 1 d . . . . .
H17A H 0.1942 0.4885 0.3107 0.140 Uiso 1 1 calc R U . . .
H17B H 0.1513 0.5973 0.3052 0.140 Uiso 1 1 calc R U . . .
H17C H 0.1454 0.5428 0.3817 0.140 Uiso 1 1 calc R U . . .
C18 C 0.3955(5) 0.5931(3) 0.2836(2) 0.0803(15) Uani 1 1 d . . . . .
H18A H 0.4759 0.6209 0.2949 0.120 Uiso 1 1 calc R U . . .
H18B H 0.3512 0.6349 0.2499 0.120 Uiso 1 1 calc R U . . .
H18C H 0.4070 0.5305 0.2610 0.120 Uiso 1 1 calc R U . . .
C19 C 0.1011(3) 0.6079(2) 0.55986(17) 0.0434(7) Uani 1 1 d . . . . .
H19 H 0.0616 0.6682 0.5618 0.052 Uiso 1 1 calc R U . . .
C20 C 0.0303(3) 0.5292(3) 0.58216(17) 0.0434(7) Uani 1 1 d . . . . .
C21 C 0.0766(3) 0.4344(2) 0.58560(16) 0.0409(7) Uani 1 1 d . . . . .
C22 C -0.0021(3) 0.3640(3) 0.61544(19) 0.0526(9) Uani 1 1 d . . . . .
H22 H 0.0260 0.3000 0.6182 0.063 Uiso 1 1 calc R U . . .
C23 C -0.1164(4) 0.3855(4) 0.6401(2) 0.0642(12) Uani 1 1 d . . . . .
H23 H -0.1659 0.3367 0.6606 0.077 Uiso 1 1 calc R U . . .
C24 C -0.1625(3) 0.4782(4) 0.6360(2) 0.0657(11) Uani 1 1 d . . . . .
H24 H -0.2433 0.4922 0.6527 0.079 Uiso 1 1 calc R U . . .
C25 C -0.0910(3) 0.5477(3) 0.6079(2) 0.0559(9) Uani 1 1 d . . . . .
H25 H -0.1224 0.6107 0.6053 0.067 Uiso 1 1 calc R U . . .
C26 C 0.3454(4) 0.7388(3) 0.6168(2) 0.0587(10) Uani 1 1 d . . . . .
C27 C 0.4494(5) 0.6702(4) 0.6278(3) 0.0980(19) Uani 1 1 d . . . . .
H27A H 0.4166 0.6055 0.6328 0.147 Uiso 1 1 calc R U . . .
H27B H 0.4949 0.6873 0.6720 0.147 Uiso 1 1 calc R U . . .
H27C H 0.5048 0.6728 0.5857 0.147 Uiso 1 1 calc R U . . .
C28 C 0.2504(5) 0.7288(5) 0.6748(3) 0.106(2) Uani 1 1 d . . . . .
H28A H 0.1841 0.7749 0.6663 0.159 Uiso 1 1 calc R U . . .
H28B H 0.2878 0.7410 0.7225 0.159 Uiso 1 1 calc R U . . .
H28C H 0.2166 0.6641 0.6738 0.159 Uiso 1 1 calc R U . . .
C29 C 0.3920(7) 0.8403(4) 0.6132(4) 0.117(2) Uani 1 1 d . . . . .
H29A H 0.4423 0.8485 0.5693 0.176 Uiso 1 1 calc R U . . .
H29B H 0.4421 0.8538 0.6564 0.176 Uiso 1 1 calc R U . . .
H29C H 0.3220 0.8842 0.6116 0.176 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
Rh1 O1 2.030(2) . ?
Rh1 N1 2.067(3) . ?
Rh1 C1 2.113(3) . ?
Rh1 C2 2.131(3) . ?
Rh1 C4 2.104(3) . ?
Rh1 C5 2.113(3) . ?
S1 O2 1.476(3) . ?
S1 N1 1.735(3) . ?
S1 C26 1.869(4) . ?
F1 C8 1.344(4) . ?
F2 C9 1.341(4) . ?
F3 C10 1.343(4) . ?
F4 C11 1.345(4) . ?
O1 C21 1.288(4) . ?
N1 C19 1.297(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.389(4) . ?
C1 C6 1.515(4) . ?
C2 C3 1.546(4) . ?
C2 C13 1.517(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.531(4) . ?
C3 C7 1.517(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.390(4) . ?
C5 C6 1.537(4) . ?
C5 C16 1.510(4) . ?
C6 H6 1.0000 . ?
C6 C12 1.521(4) . ?
C7 C8 1.380(4) . ?
C7 C12 1.392(4) . ?
C8 C9 1.378(5) . ?
C9 C10 1.360(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.370(4) . ?
C13 H13 1.0000 . ?
C13 C14 1.525(5) . ?
C13 C15 1.507(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.518(6) . ?
C16 C18 1.515(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.408(5) . ?
C20 C21 1.424(5) . ?
C20 C25 1.424(5) . ?
C21 C22 1.417(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.357(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.397(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.350(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.500(7) . ?
C26 C28 1.490(6) . ?
C26 C29 1.513(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
O1 Rh1 N1 88.48(9) . . ?
O1 Rh1 C1 92.57(10) . . ?
O1 Rh1 C2 99.10(10) . . ?
O1 Rh1 C4 165.45(11) . . ?
O1 Rh1 C5 146.96(11) . . ?
N1 Rh1 C1 166.28(11) . . ?
N1 Rh1 C2 154.78(11) . . ?
N1 Rh1 C4 102.54(11) . . ?
N1 Rh1 C5 106.29(11) . . ?
C1 Rh1 C2 38.20(11) . . ?
C1 Rh1 C5 66.31(12) . . ?
C4 Rh1 C1 79.01(12) . . ?
C4 Rh1 C2 66.96(12) . . ?
C4 Rh1 C5 38.49(12) . . ?
C5 Rh1 C2 80.14(11) . . ?
O2 S1 N1 108.19(15) . . ?
O2 S1 C26 105.3(2) . . ?
N1 S1 C26 99.65(16) . . ?
C21 O1 Rh1 127.6(2) . . ?
S1 N1 Rh1 120.86(14) . . ?
C19 N1 Rh1 124.1(2) . . ?
C19 N1 S1 114.8(2) . . ?
Rh1 C1 H1 120.3 . . ?
C2 C1 Rh1 71.61(17) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C6 114.6(3) . . ?
C6 C1 Rh1 97.10(19) . . ?
C6 C1 H1 120.3 . . ?
C1 C2 Rh1 70.19(17) . . ?
C1 C2 C3 111.8(3) . . ?
C1 C2 C13 123.2(3) . . ?
C3 C2 Rh1 95.32(17) . . ?
C13 C2 Rh1 117.4(2) . . ?
C13 C2 C3 122.3(3) . . ?
C2 C3 H3 113.3 . . ?
C4 C3 C2 98.8(2) . . ?
C4 C3 H3 113.3 . . ?
C7 C3 C2 108.6(2) . . ?
C7 C3 H3 113.3 . . ?
C7 C3 C4 108.3(2) . . ?
Rh1 C4 H4 120.6 . . ?
C3 C4 Rh1 96.86(18) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 Rh1 71.07(17) . . ?
C5 C4 C3 114.1(3) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 Rh1 70.44(16) . . ?
C4 C5 C6 112.2(3) . . ?
C4 C5 C16 125.8(3) . . ?
C6 C5 Rh1 96.42(18) . . ?
C16 C5 Rh1 118.8(2) . . ?
C16 C5 C6 118.7(3) . . ?
C1 C6 C5 98.4(2) . . ?
C1 C6 H6 113.2 . . ?
C1 C6 C12 109.5(3) . . ?
C5 C6 H6 113.2 . . ?
C12 C6 C5 108.4(3) . . ?
C12 C6 H6 113.2 . . ?
C8 C7 C3 127.6(3) . . ?
C8 C7 C12 118.8(3) . . ?
C12 C7 C3 113.5(3) . . ?
F1 C8 C7 120.9(3) . . ?
F1 C8 C9 118.6(3) . . ?
C9 C8 C7 120.4(3) . . ?
F2 C9 C8 120.1(3) . . ?
F2 C9 C10 119.3(3) . . ?
C10 C9 C8 120.6(3) . . ?
F3 C10 C9 120.0(3) . . ?
F3 C10 C11 120.4(3) . . ?
C9 C10 C11 119.6(3) . . ?
F4 C11 C10 118.8(3) . . ?
F4 C11 C12 120.8(3) . . ?
C12 C11 C10 120.4(3) . . ?
C7 C12 C6 113.1(3) . . ?
C11 C12 C6 126.7(3) . . ?
C11 C12 C7 120.1(3) . . ?
C2 C13 H13 107.5 . . ?
C2 C13 C14 108.7(3) . . ?
C14 C13 H13 107.5 . . ?
C15 C13 C2 114.0(3) . . ?
C15 C13 H13 107.5 . . ?
C15 C13 C14 111.5(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16 108.0 . . ?
C5 C16 C17 112.7(3) . . ?
C5 C16 C18 109.6(3) . . ?
C17 C16 H16 108.0 . . ?
C18 C16 H16 108.0 . . ?
C18 C16 C17 110.5(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19 116.3 . . ?
N1 C19 C20 127.5(3) . . ?
C20 C19 H19 116.3 . . ?
C19 C20 C21 123.6(3) . . ?
C19 C20 C25 117.3(3) . . ?
C21 C20 C25 118.9(3) . . ?
O1 C21 C20 124.9(3) . . ?
O1 C21 C22 117.9(3) . . ?
C22 C21 C20 117.1(3) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.7(4) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.2(4) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.1(4) . . ?
C25 C24 H24 120.4 . . ?
C20 C25 H25 119.0 . . ?
C24 C25 C20 121.9(4) . . ?
C24 C25 H25 119.0 . . ?
C27 C26 S1 109.0(3) . . ?
C27 C26 C29 111.0(5) . . ?
C28 C26 S1 111.3(3) . . ?
C28 C26 C27 111.5(5) . . ?
C28 C26 C29 110.6(5) . . ?
C29 C26 S1 103.2(4) . . ?
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 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Rh1 O1 C21 C20 -10.1(5) . . . . ?
Rh1 O1 C21 C22 170.6(2) . . . . ?
Rh1 N1 C19 C20 13.3(5) . . . . ?
Rh1 C1 C2 C3 -87.8(2) . . . . ?
Rh1 C1 C2 C13 110.4(3) . . . . ?
Rh1 C1 C6 C5 11.3(2) . . . . ?
Rh1 C1 C6 C12 124.4(2) . . . . ?
Rh1 C2 C3 C4 -12.1(2) . . . . ?
Rh1 C2 C3 C7 -125.0(2) . . . . ?
Rh1 C2 C13 C14 -178.1(3) . . . . ?
Rh1 C2 C13 C15 -53.0(4) . . . . ?
Rh1 C4 C5 C6 -89.0(2) . . . . ?
Rh1 C4 C5 C16 111.9(3) . . . . ?
Rh1 C5 C6 C1 -11.3(2) . . . . ?
Rh1 C5 C6 C12 -125.2(2) . . . . ?
Rh1 C5 C16 C17 -57.0(4) . . . . ?
Rh1 C5 C16 C18 179.5(3) . . . . ?
S1 N1 C19 C20 -172.7(3) . . . . ?
F1 C8 C9 F2 -2.2(5) . . . . ?
F1 C8 C9 C10 178.8(3) . . . . ?
F2 C9 C10 F3 2.4(6) . . . . ?
F2 C9 C10 C11 -178.5(3) . . . . ?
F3 C10 C11 F4 0.8(5) . . . . ?
F3 C10 C11 C12 179.2(3) . . . . ?
F4 C11 C12 C6 -2.9(5) . . . . ?
F4 C11 C12 C7 178.1(3) . . . . ?
O1 C21 C22 C23 179.0(3) . . . . ?
O2 S1 N1 Rh1 154.89(19) . . . . ?
O2 S1 N1 C19 -19.3(3) . . . . ?
O2 S1 C26 C27 179.8(3) . . . . ?
O2 S1 C26 C28 56.4(4) . . . . ?
O2 S1 C26 C29 -62.2(4) . . . . ?
N1 S1 C26 C27 67.8(4) . . . . ?
N1 S1 C26 C28 -55.6(4) . . . . ?
N1 S1 C26 C29 -174.2(4) . . . . ?
N1 C19 C20 C21 2.8(5) . . . . ?
N1 C19 C20 C25 177.7(3) . . . . ?
C1 C2 C3 C4 58.7(3) . . . . ?
C1 C2 C3 C7 -54.2(3) . . . . ?
C1 C2 C13 C14 98.6(4) . . . . ?
C1 C2 C13 C15 -136.3(4) . . . . ?
C1 C6 C12 C7 -51.7(4) . . . . ?
C1 C6 C12 C11 129.2(3) . . . . ?
C2 C1 C6 C5 -61.7(3) . . . . ?
C2 C1 C6 C12 51.4(3) . . . . ?
C2 C3 C4 Rh1 12.3(2) . . . . ?
C2 C3 C4 C5 -60.0(3) . . . . ?
C2 C3 C7 C8 -127.8(4) . . . . ?
C2 C3 C7 C12 54.0(3) . . . . ?
C3 C2 C13 C14 -61.3(4) . . . . ?
C3 C2 C13 C15 63.7(4) . . . . ?
C3 C4 C5 Rh1 89.1(2) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 C16 -158.9(3) . . . . ?
C3 C7 C8 F1 3.0(6) . . . . ?
C3 C7 C8 C9 -177.2(3) . . . . ?
C3 C7 C12 C6 -1.0(4) . . . . ?
C3 C7 C12 C11 178.1(3) . . . . ?
C4 C3 C7 C8 125.8(4) . . . . ?
C4 C3 C7 C12 -52.4(4) . . . . ?
C4 C5 C6 C1 60.1(3) . . . . ?
C4 C5 C6 C12 -53.8(3) . . . . ?
C4 C5 C16 C17 -142.8(4) . . . . ?
C4 C5 C16 C18 93.8(4) . . . . ?
C5 C6 C12 C7 54.6(3) . . . . ?
C5 C6 C12 C11 -124.4(3) . . . . ?
C6 C1 C2 Rh1 89.5(2) . . . . ?
C6 C1 C2 C3 1.7(4) . . . . ?
C6 C1 C2 C13 -160.2(3) . . . . ?
C6 C5 C16 C17 59.5(4) . . . . ?
C6 C5 C16 C18 -64.0(4) . . . . ?
C7 C3 C4 Rh1 125.3(2) . . . . ?
C7 C3 C4 C5 53.1(3) . . . . ?
C7 C8 C9 F2 178.0(4) . . . . ?
C7 C8 C9 C10 -1.1(6) . . . . ?
C8 C7 C12 C6 -179.4(3) . . . . ?
C8 C7 C12 C11 -0.3(5) . . . . ?
C8 C9 C10 F3 -178.5(3) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C9 C10 C11 F4 -178.2(3) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C6 178.7(3) . . . . ?
C10 C11 C12 C7 -0.3(5) . . . . ?
C12 C7 C8 F1 -178.9(3) . . . . ?
C12 C7 C8 C9 0.9(6) . . . . ?
C13 C2 C3 C4 -139.3(3) . . . . ?
C13 C2 C3 C7 107.8(3) . . . . ?
C16 C5 C6 C1 -139.2(3) . . . . ?
C16 C5 C6 C12 106.9(3) . . . . ?
C19 C20 C21 O1 -5.0(5) . . . . ?
C19 C20 C21 C22 174.3(3) . . . . ?
C19 C20 C25 C24 -174.6(3) . . . . ?
C20 C21 C22 C23 -0.4(5) . . . . ?
C21 C20 C25 C24 0.6(5) . . . . ?
C21 C22 C23 C24 1.2(6) . . . . ?
C22 C23 C24 C25 -1.1(6) . . . . ?
C23 C24 C25 C20 0.2(6) . . . . ?
C25 C20 C21 O1 -179.8(3) . . . . ?
C25 C20 C21 C22 -0.5(4) . . . . ?
C26 S1 N1 Rh1 -95.42(19) . . . . ?
C26 S1 N1 C19 90.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9a
_database_code_depnum_ccdc_archive 'CCDC 2159992'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2022-03-21 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H23 N O3'
_chemical_formula_weight         301.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0026 0.0018 '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 0.0049 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0092 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.1340(18)
_cell_length_b                   6.2150(12)
_cell_length_c                   14.976(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.66(3)
_cell_angle_gamma                90
_cell_volume                     814.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3026
_cell_measurement_temperature    120
_cell_measurement_theta_max      14.85
_cell_measurement_theta_min      2.26

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5296
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_measurement_device_type  
'MarExperts mardtb goniostat and Rayonix SX 165 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.745
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8466
_diffrn_reflns_av_unetI/netI     0.1191
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.467
_diffrn_reflns_theta_max         31.098
_diffrn_reflns_theta_full        26.551
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4400
_reflns_number_gt                4250
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.957

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0790P)²+0.0622P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 
;
 Flack x determined using 1825 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4400
_refine_ls_number_parameters     206
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_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
O1 O -0.7241(2) -0.8120(3) -0.43780(12) 0.0269(4) Uani 1 1 d . . . . .
O2 O -0.26965(18) -0.4988(3) -0.26243(11) 0.0263(4) Uani 1 1 d . . . . .
O3 O -0.42384(16) -0.5949(2) -0.17472(10) 0.0199(3) Uani 1 1 d . . . . .
N1 N -0.7022(2) -0.4571(3) -0.47337(11) 0.0183(3) Uani 1 1 d . . . . .
C1 C -0.5522(2) -0.4342(3) -0.41081(13) 0.0178(4) Uani 1 1 d . . . . .
H1 H -0.4736 -0.5323 -0.4234 0.021 Uiso 1 1 calc R U . . .
C2 C -0.5295(2) -0.3819(3) -0.30720(12) 0.0164(3) Uani 1 1 d . . . . .
C3 C -0.4941(2) -0.2186(3) -0.37367(14) 0.0210(4) Uani 1 1 d . . . . .
H3A H -0.5642 -0.0945 -0.3923 0.025 Uiso 1 1 calc R U . . .
H3B H -0.3854 -0.1860 -0.3667 0.025 Uiso 1 1 calc R U . . .
C4 C -0.7697(2) -0.6542(3) -0.48711(14) 0.0214(4) Uani 1 1 d . . . . .
C6 C -0.9138(3) -0.4124(4) -0.60503(15) 0.0254(4) Uani 1 1 d . . . . .
H6BC H -0.9299 -0.3961 -0.6729 0.030 Uiso 0.768(13) 1 calc R U P A 2
H6BD H -1.0006 -0.3454 -0.5883 0.030 Uiso 0.768(13) 1 calc R U P A 2
H6AA H -0.9996 -0.3137 -0.6068 0.030 Uiso 0.232(13) 1 calc R U P A 1
H6AB H -0.9129 -0.4414 -0.6699 0.030 Uiso 0.232(13) 1 calc R U P A 1
C7 C -0.7634(3) -0.3104(4) -0.55053(17) 0.0313(5) Uani 1 1 d . U . . .
H7A H -0.6930 -0.2972 -0.5897 0.038 Uiso 1 1 calc R U . . .
H7B H -0.7805 -0.1659 -0.5276 0.038 Uiso 1 1 calc R U . . .
C8 C -0.3927(2) -0.4959(3) -0.24639(13) 0.0193(4) Uani 1 1 d . . . . .
C9 C -0.3047(2) -0.7151(4) -0.10484(13) 0.0204(4) Uani 1 1 d . . . . .
C10 C -0.3934(3) -0.8022(4) -0.04055(15) 0.0256(4) Uani 1 1 d . . . . .
H10A H -0.4763 -0.8951 -0.0762 0.038 Uiso 1 1 calc R U . . .
H10B H -0.4363 -0.6820 -0.0140 0.038 Uiso 1 1 calc R U . . .
H10C H -0.3244 -0.8854 0.0098 0.038 Uiso 1 1 calc R U . . .
C11 C -0.2429(3) -0.8989(4) -0.15068(17) 0.0301(5) Uani 1 1 d . . . . .
H11A H -0.1819 -0.8403 -0.1892 0.045 Uiso 1 1 calc R U . . .
H11B H -0.3282 -0.9825 -0.1899 0.045 Uiso 1 1 calc R U . . .
H11C H -0.1786 -0.9923 -0.1024 0.045 Uiso 1 1 calc R U . . .
C12 C -0.1794(3) -0.5612(5) -0.05370(16) 0.0314(5) Uani 1 1 d . . . . .
H12A H -0.2253 -0.4356 -0.0326 0.047 Uiso 1 1 calc R U . . .
H12B H -0.1210 -0.5143 -0.0958 0.047 Uiso 1 1 calc R U . . .
H12C H -0.1110 -0.6343 0.0003 0.047 Uiso 1 1 calc R U . . .
C13 C -0.6634(2) -0.3427(3) -0.27082(12) 0.0158(4) Uani 1 1 d . . . . .
C14 C -0.6880(2) -0.1376(3) -0.23963(13) 0.0187(4) Uani 1 1 d . . . . .
H14 H -0.6219 -0.0227 -0.2441 0.022 Uiso 1 1 calc R U . . .
C15 C -0.8088(2) -0.0999(3) -0.20187(14) 0.0208(4) Uani 1 1 d . . . . .
H15 H -0.8226 0.0391 -0.1792 0.025 Uiso 1 1 calc R U . . .
C16 C -0.9088(2) -0.2649(3) -0.19745(14) 0.0206(4) Uani 1 1 d . . . . .
H16 H -0.9919 -0.2389 -0.1726 0.025 Uiso 1 1 calc R U . . .
C17 C -0.8865(2) -0.4687(3) -0.22958(14) 0.0202(4) Uani 1 1 d . . . . .
H17 H -0.9553 -0.5816 -0.2271 0.024 Uiso 1 1 calc R U . . .
C18 C -0.7641(2) -0.5087(3) -0.26531(13) 0.0183(4) Uani 1 1 d . . . . .
H18 H -0.7489 -0.6492 -0.2860 0.022 Uiso 1 1 calc R U . . .
C5' C -0.9328(16) -0.614(2) -0.5589(10) 0.0239(9) Uani 0.232(13) 1 d . . P A 1
H5'A H -0.9612 -0.7332 -0.6044 0.029 Uiso 0.232(13) 1 calc R U P A 1
H5'B H -1.0122 -0.5993 -0.5261 0.029 Uiso 0.232(13) 1 calc R U P A 1
C5 C -0.8981(5) -0.6532(6) -0.5767(3) 0.0239(9) Uani 0.768(13) 1 d . . P A 2
H5A H -0.9938 -0.7083 -0.5667 0.029 Uiso 0.768(13) 1 calc R U P A 2
H5B H -0.8721 -0.7417 -0.6250 0.029 Uiso 0.768(13) 1 calc R U P A 2


_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
O1 C4 1.226(3) . ?
O2 C8 1.215(2) . ?
O3 C8 1.337(2) . ?
O3 C9 1.478(2) . ?
N1 C4 1.360(3) . ?
N1 C1 1.428(3) . ?
N1 C7 1.452(3) . ?
C1 C3 1.488(3) . ?
C1 C2 1.540(3) . ?
C1 H1 1.0000 . ?
C2 C13 1.495(3) . ?
C2 C8 1.497(3) . ?
C2 C3 1.520(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.508(4) . ?
C4 C5' 1.587(13) . ?
C6 C5' 1.465(13) . ?
C6 C7 1.520(3) . ?
C6 C5 1.551(4) . ?
C6 H6BC 0.9900 . ?
C6 H6BD 0.9900 . ?
C6 H6AA 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C12 1.520(3) . ?
C9 C11 1.523(3) . ?
C9 C10 1.524(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.398(3) . ?
C13 C18 1.400(3) . ?
C14 C15 1.397(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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
C8 O3 C9 121.23(15) . . ?
C4 N1 C1 119.80(17) . . ?
C4 N1 C7 113.01(18) . . ?
C1 N1 C7 122.49(18) . . ?
N1 C1 C3 120.47(17) . . ?
N1 C1 C2 120.58(16) . . ?
C3 C1 C2 60.22(12) . . ?
N1 C1 H1 114.9 . . ?
C3 C1 H1 114.9 . . ?
C2 C1 H1 114.9 . . ?
C13 C2 C8 118.90(15) . . ?
C13 C2 C3 118.65(16) . . ?
C8 C2 C3 114.67(16) . . ?
C13 C2 C1 120.91(16) . . ?
C8 C2 C1 111.17(16) . . ?
C3 C2 C1 58.21(13) . . ?
C1 C3 C2 61.57(13) . . ?
C1 C3 H3A 117.6 . . ?
C2 C3 H3A 117.6 . . ?
C1 C3 H3B 117.6 . . ?
C2 C3 H3B 117.6 . . ?
H3A C3 H3B 114.7 . . ?
O1 C4 N1 124.64(19) . . ?
O1 C4 C5 125.6(2) . . ?
N1 C4 C5 109.5(2) . . ?
O1 C4 C5' 128.6(5) . . ?
N1 C4 C5' 104.9(5) . . ?
C5' C6 C7 108.3(5) . . ?
C7 C6 C5 104.9(2) . . ?
C7 C6 H6BC 110.8 . . ?
C5 C6 H6BC 110.8 . . ?
C7 C6 H6BD 110.8 . . ?
C5 C6 H6BD 110.8 . . ?
H6BC C6 H6BD 108.8 . . ?
C5' C6 H6AA 110.0 . . ?
C7 C6 H6AA 110.0 . . ?
C5' C6 H6AB 110.0 . . ?
C7 C6 H6AB 110.0 . . ?
H6AA C6 H6AB 108.4 . . ?
N1 C7 C6 104.34(19) . . ?
N1 C7 H7A 110.9 . . ?
C6 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O2 C8 O3 125.02(18) . . ?
O2 C8 C2 123.03(18) . . ?
O3 C8 C2 111.95(16) . . ?
O3 C9 C12 109.52(18) . . ?
O3 C9 C11 110.66(17) . . ?
C12 C9 C11 112.1(2) . . ?
O3 C9 C10 102.14(16) . . ?
C12 C9 C10 111.42(18) . . ?
C11 C9 C10 110.58(19) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.76(17) . . ?
C14 C13 C2 119.82(16) . . ?
C18 C13 C2 121.40(17) . . ?
C15 C14 C13 120.64(18) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.17(18) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.55(18) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.59(19) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.26(19) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C6 C5' C4 103.8(7) . . ?
C6 C5' H5'A 111.0 . . ?
C4 C5' H5'A 111.0 . . ?
C6 C5' H5'B 111.0 . . ?
C4 C5' H5'B 111.0 . . ?
H5'A C5' H5'B 109.0 . . ?
C4 C5 C6 103.6(2) . . ?
C4 C5 H5A 111.0 . . ?
C6 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
C6 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?

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
C4 N1 C1 C3 -162.28(18) . . . . ?
C7 N1 C1 C3 43.7(3) . . . . ?
C4 N1 C1 C2 -91.1(2) . . . . ?
C7 N1 C1 C2 114.9(2) . . . . ?
N1 C1 C2 C13 -3.3(3) . . . . ?
C3 C1 C2 C13 106.6(2) . . . . ?
N1 C1 C2 C8 143.44(19) . . . . ?
C3 C1 C2 C8 -106.65(18) . . . . ?
N1 C1 C2 C3 -109.9(2) . . . . ?
N1 C1 C3 C2 110.08(19) . . . . ?
C13 C2 C3 C1 -110.49(19) . . . . ?
C8 C2 C3 C1 100.54(18) . . . . ?
C1 N1 C4 O1 13.7(3) . . . . ?
C7 N1 C4 O1 170.0(2) . . . . ?
C1 N1 C4 C5 -160.8(3) . . . . ?
C7 N1 C4 C5 -4.5(3) . . . . ?
C1 N1 C4 C5' 179.4(7) . . . . ?
C7 N1 C4 C5' -24.3(7) . . . . ?
C4 N1 C7 C6 16.8(3) . . . . ?
C1 N1 C7 C6 172.37(18) . . . . ?
C5' C6 C7 N1 -0.9(8) . . . . ?
C5 C6 C7 N1 -21.4(3) . . . . ?
C9 O3 C8 O2 2.0(3) . . . . ?
C9 O3 C8 C2 -179.11(17) . . . . ?
C13 C2 C8 O2 -165.6(2) . . . . ?
C3 C2 C8 O2 -16.8(3) . . . . ?
C1 C2 C8 O2 46.9(3) . . . . ?
C13 C2 C8 O3 15.4(3) . . . . ?
C3 C2 C8 O3 164.33(17) . . . . ?
C1 C2 C8 O3 -132.01(17) . . . . ?
C8 O3 C9 C12 63.3(2) . . . . ?
C8 O3 C9 C11 -60.7(2) . . . . ?
C8 O3 C9 C10 -178.45(18) . . . . ?
C8 C2 C13 C14 103.2(2) . . . . ?
C3 C2 C13 C14 -44.4(2) . . . . ?
C1 C2 C13 C14 -112.5(2) . . . . ?
C8 C2 C13 C18 -75.4(2) . . . . ?
C3 C2 C13 C18 136.95(19) . . . . ?
C1 C2 C13 C18 68.8(2) . . . . ?
C18 C13 C14 C15 1.3(3) . . . . ?
C2 C13 C14 C15 -177.36(17) . . . . ?
C13 C14 C15 C16 -1.9(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C2 C13 C18 C17 178.85(17) . . . . ?
C7 C6 C5' C4 -12.2(11) . . . . ?
O1 C4 C5' C6 -173.1(4) . . . . ?
N1 C4 C5' C6 22.0(10) . . . . ?
O1 C4 C5 C6 176.1(2) . . . . ?
N1 C4 C5 C6 -9.5(4) . . . . ?
C7 C6 C5 C4 18.9(4) . . . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6

