# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_cu_sb632
_publcif_datablock.id            {1919ea22-7769-44af-93c9-dd92095895e6}
_audit_update_record             
;
2013-12-17 # Formatted by publCIF

;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ethyl-4,6-di(1H-indol-3-yl)-1-phenylpiperidin-2-carboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H29 N3 O2'
_chemical_formula_sum            'C30 H29 N3 O2'
_chemical_formula_weight         463.56

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   7.9687(8)
_cell_length_b                   9.4665(9)
_cell_length_c                   9.6211(9)
_cell_angle_alpha                62.398(9)
_cell_angle_beta                 77.124(8)
_cell_angle_gamma                81.985(8)
_cell_volume                     626.45(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8138
_cell_measurement_theta_min      5.26
_cell_measurement_theta_max      76.26

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             246
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.613
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 dx = 54 mm, 57 sets,  1256 frames, 2 deg., 3 and 20 sec.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   
;
SuperNova (Cu) X-ray Source
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans, 2°'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_reflns_number            9604
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.274
_diffrn_reflns_theta_max         76.554
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             4786
_reflns_number_gt                4736
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_max     0.843
_reflns_Friedel_fraction_full    0.896

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;
SHELXL-2013 (Sheldrick, 2013)
;
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  publCif

_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)+(0.0316P)²+0.1014P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0140(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2171 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
 Hooft's y parameter 0.02(5) (Hooft, Straver, Spek (2008), 
 J. Appl. Cryst. 46, 96-103).
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4786
_refine_ls_number_parameters     323
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
N1 N 0.47895(18) 0.37724(16) 0.52724(16) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.5042(2) 0.54805(19) 0.46547(19) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.3904 0.6063 0.4468 0.024 Uiso 1 1 calc R U . . .
C3 C 0.5664(2) 0.58163(19) 0.58577(19) 0.0203(3) Uani 1 1 d . . . . .
H3A H 0.4794 0.5485 0.6852 0.024 Uiso 1 1 calc R U . . .
H3B H 0.5819 0.6974 0.5418 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7380(2) 0.48917(19) 0.62217(18) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.8202 0.5207 0.5186 0.023 Uiso 1 1 calc R U . . .
C5 C 0.7066(2) 0.3124(2) 0.6896(2) 0.0209(3) Uani 1 1 d . . . . .
H5A H 0.6279 0.2784 0.7939 0.025 Uiso 1 1 calc R U . . .
H5B H 0.8174 0.2512 0.7088 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6291(2) 0.26964(19) 0.58160(19) 0.0194(3) Uani 1 1 d . . . . .
H6 H 0.7186 0.2803 0.4865 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3871(2) 0.34568(19) 0.43329(19) 0.0202(3) Uani 1 1 d . . . . .
C12 C 0.4603(2) 0.2663(2) 0.3417(2) 0.0244(4) Uani 1 1 d . . . . .
H12 H 0.5765 0.2264 0.3425 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3640(3) 0.2452(2) 0.2490(2) 0.0291(4) Uani 1 1 d . . . . .
H13 H 0.4150 0.1904 0.1875 0.035 Uiso 1 1 calc R U . . .
C14 C 0.1946(3) 0.3032(2) 0.2453(2) 0.0306(4) Uani 1 1 d . . . . .
H14 H 0.1304 0.2905 0.1800 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1199(2) 0.3800(2) 0.3381(2) 0.0301(4) Uani 1 1 d . . . . .
H15 H 0.0038 0.4198 0.3367 0.036 Uiso 1 1 calc R U . . .
C16 C 0.2145(2) 0.3990(2) 0.4329(2) 0.0248(4) Uani 1 1 d . . . . .
H16 H 0.1611 0.4489 0.4985 0.030 Uiso 1 1 calc R U . . .
C21 C 0.6322(2) 0.6167(2) 0.30706(19) 0.0193(3) Uani 1 1 d . . . . .
O21 O 0.71502(16) 0.54009(15) 0.24145(14) 0.0246(3) Uani 1 1 d . . . . .
O22 O 0.64602(16) 0.77212(14) 0.25447(14) 0.0252(3) Uani 1 1 d . . . . .
C22 C 0.7739(2) 0.8517(2) 0.1120(2) 0.0267(4) Uani 1 1 d . . . . .
H22A H 0.7419 0.8513 0.0185 0.032 Uiso 1 1 calc R U . . .
H22B H 0.8886 0.7973 0.1263 0.032 Uiso 1 1 calc R U . . .
C23 C 0.7764(3) 1.0196(2) 0.0887(3) 0.0367(5) Uani 1 1 d . . . . .
H23A H 0.8602 1.0790 -0.0069 0.055 Uiso 1 1 calc R U . . .
H23B H 0.8090 1.0180 0.1819 0.055 Uiso 1 1 calc R U . . .
H23C H 0.6617 1.0713 0.0760 0.055 Uiso 1 1 calc R U . . .
N1' N 0.8768(2) 0.54191(19) 0.93940(17) 0.0256(3) Uani 1 1 d D . . . .
H1' H 0.856(3) 0.539(3) 1.033(2) 0.031 Uiso 1 1 d D U . . .
C2' C 0.7796(2) 0.4692(2) 0.8907(2) 0.0235(4) Uani 1 1 d . . . . .
H2' H 0.6989 0.3896 0.9598 0.028 Uiso 1 1 calc R U . . .
C3' C 0.8164(2) 0.52846(19) 0.72786(19) 0.0196(3) Uani 1 1 d . . . . .
C3A' C 0.9423(2) 0.6465(2) 0.67244(19) 0.0195(3) Uani 1 1 d . . . . .
C4' C 1.0261(2) 0.7511(2) 0.5202(2) 0.0230(3) Uani 1 1 d . . . . .
H4' H 1.0048 0.7498 0.4275 0.028 Uiso 1 1 calc R U . . .
C5' C 1.1398(3) 0.8556(2) 0.5074(2) 0.0305(4) Uani 1 1 d . . . . .
H5' H 1.1983 0.9254 0.4049 0.037 Uiso 1 1 calc R U . . .
C6' C 1.1707(3) 0.8608(3) 0.6437(3) 0.0340(4) Uani 1 1 d . . . . .
H6' H 1.2487 0.9347 0.6316 0.041 Uiso 1 1 calc R U . . .
C7' C 1.0891(3) 0.7600(3) 0.7945(2) 0.0311(4) Uani 1 1 d . . . . .
H7' H 1.1093 0.7635 0.8865 0.037 Uiso 1 1 calc R U . . .
C7A' C 0.9764(2) 0.6531(2) 0.8072(2) 0.0233(4) Uani 1 1 d . . . . .
N1" N 0.59749(19) -0.16783(17) 0.77263(17) 0.0225(3) Uani 1 1 d D . . . .
H1" H 0.634(3) -0.266(2) 0.786(3) 0.027 Uiso 1 1 d D U . . .
C2" C 0.6620(2) -0.0265(2) 0.6526(2) 0.0222(3) Uani 1 1 d . . . . .
H2" H 0.7521 -0.0174 0.5659 0.027 Uiso 1 1 calc R U . . .
C3" C 0.5785(2) 0.0990(2) 0.67564(19) 0.0197(3) Uani 1 1 d . . . . .
C3A" C 0.4530(2) 0.03146(19) 0.82057(19) 0.0196(3) Uani 1 1 d . . . . .
C4" C 0.3312(2) 0.0947(2) 0.9096(2) 0.0249(4) Uani 1 1 d . . . . .
H4" H 0.3137 0.2067 0.8724 0.030 Uiso 1 1 calc R U . . .
C5" C 0.2373(2) -0.0097(2) 1.0526(2) 0.0286(4) Uani 1 1 d . . . . .
H5" H 0.1554 0.0318 1.1141 0.034 Uiso 1 1 calc R U . . .
C6" C 0.2606(2) -0.1757(2) 1.1088(2) 0.0278(4) Uani 1 1 d . . . . .
H6" H 0.1955 -0.2440 1.2083 0.033 Uiso 1 1 calc R U . . .
C7" C 0.3759(2) -0.2419(2) 1.0226(2) 0.0243(4) Uani 1 1 d . . . . .
H7" H 0.3899 -0.3542 1.0594 0.029 Uiso 1 1 calc R U . . .
C7A" C 0.4711(2) -0.1363(2) 0.8786(2) 0.0205(3) Uani 1 1 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
N1 C11 1.431(2) . ?
N1 C2 1.468(2) . ?
N1 C6 1.479(2) . ?
C2 C3 1.525(2) . ?
C2 C21 1.536(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.534(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C3' 1.504(2) . ?
C4 C5 1.524(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.540(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C3" 1.502(2) . ?
C6 H6 1.0000 . ?
C11 C12 1.395(2) . ?
C11 C16 1.397(2) . ?
C12 C13 1.392(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 O21 1.210(2) . ?
C21 O22 1.328(2) . ?
O22 C22 1.456(2) . ?
C22 C23 1.501(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N1' C7A' 1.378(2) . ?
N1' C2' 1.380(2) . ?
N1' H1' 0.865(19) . ?
C2' C3' 1.371(2) . ?
C2' H2' 0.9500 . ?
C3' C3A' 1.436(3) . ?
C3A' C4' 1.406(2) . ?
C3A' C7A' 1.413(2) . ?
C4' C5' 1.379(3) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.411(3) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.381(3) . ?
C6' H6' 0.9500 . ?
C7' C7A' 1.391(3) . ?
C7' H7' 0.9500 . ?
N1" C2" 1.372(2) . ?
N1" C7A" 1.372(2) . ?
N1" H1" 0.895(19) . ?
C2" C3" 1.364(2) . ?
C2" H2" 0.9500 . ?
C3" C3A" 1.444(2) . ?
C3A" C4" 1.405(2) . ?
C3A" C7A" 1.416(2) . ?
C4" C5" 1.385(3) . ?
C4" H4" 0.9500 . ?
C5" C6" 1.404(3) . ?
C5" H5" 0.9500 . ?
C6" C7" 1.381(3) . ?
C6" H6" 0.9500 . ?
C7" C7A" 1.397(2) . ?
C7" H7" 0.9500 . ?

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
C11 N1 C2 112.54(13) . . ?
C11 N1 C6 117.04(13) . . ?
C2 N1 C6 115.61(13) . . ?
N1 C2 C3 111.28(13) . . ?
N1 C2 C21 113.13(13) . . ?
C3 C2 C21 108.49(14) . . ?
N1 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
C21 C2 H2 107.9 . . ?
C2 C3 C4 109.41(12) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C3' C4 C5 113.67(13) . . ?
C3' C4 C3 112.59(13) . . ?
C5 C4 C3 107.56(13) . . ?
C3' C4 H4 107.6 . . ?
C5 C4 H4 107.6 . . ?
C3 C4 H4 107.6 . . ?
C4 C5 C6 114.36(13) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
N1 C6 C3" 111.11(13) . . ?
N1 C6 C5 110.75(13) . . ?
C3" C6 C5 107.67(13) . . ?
N1 C6 H6 109.1 . . ?
C3" C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
C12 C11 C16 118.46(16) . . ?
C12 C11 N1 123.77(15) . . ?
C16 C11 N1 117.77(14) . . ?
C13 C12 C11 120.33(16) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.72(17) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.32(18) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.17(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.94(16) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
O21 C21 O22 124.11(16) . . ?
O21 C21 C2 125.31(15) . . ?
O22 C21 C2 110.51(13) . . ?
C21 O22 C22 116.92(13) . . ?
O22 C22 C23 106.18(15) . . ?
O22 C22 H22A 110.5 . . ?
C23 C22 H22A 110.5 . . ?
O22 C22 H22B 110.5 . . ?
C23 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7A' N1' C2' 109.03(14) . . ?
C7A' N1' H1' 124.2(16) . . ?
C2' N1' H1' 124.4(16) . . ?
C3' C2' N1' 110.07(16) . . ?
C3' C2' H2' 125.0 . . ?
N1' C2' H2' 125.0 . . ?
C2' C3' C3A' 106.10(15) . . ?
C2' C3' C4 128.86(16) . . ?
C3A' C3' C4 124.96(14) . . ?
C4' C3A' C7A' 118.76(16) . . ?
C4' C3A' C3' 133.54(16) . . ?
C7A' C3A' C3' 107.67(14) . . ?
C5' C4' C3A' 119.03(17) . . ?
C5' C4' H4' 120.5 . . ?
C3A' C4' H4' 120.5 . . ?
C4' C5' C6' 121.15(18) . . ?
C4' C5' H5' 119.4 . . ?
C6' C5' H5' 119.4 . . ?
C7' C6' C5' 120.93(18) . . ?
C7' C6' H6' 119.5 . . ?
C5' C6' H6' 119.5 . . ?
C6' C7' C7A' 117.80(17) . . ?
C6' C7' H7' 121.1 . . ?
C7A' C7' H7' 121.1 . . ?
N1' C7A' C7' 130.54(17) . . ?
N1' C7A' C3A' 107.11(15) . . ?
C7' C7A' C3A' 122.33(17) . . ?
C2" N1" C7A" 109.04(14) . . ?
C2" N1" H1" 127.1(15) . . ?
C7A" N1" H1" 123.8(14) . . ?
C3" C2" N1" 110.34(15) . . ?
C3" C2" H2" 124.8 . . ?
N1" C2" H2" 124.8 . . ?
C2" C3" C3A" 106.36(15) . . ?
C2" C3" C6 125.49(15) . . ?
C3A" C3" C6 127.49(14) . . ?
C4" C3A" C7A" 118.63(15) . . ?
C4" C3A" C3" 134.66(16) . . ?
C7A" C3A" C3" 106.68(14) . . ?
C5" C4" C3A" 118.66(16) . . ?
C5" C4" H4" 120.7 . . ?
C3A" C4" H4" 120.7 . . ?
C4" C5" C6" 121.43(16) . . ?
C4" C5" H5" 119.3 . . ?
C6" C5" H5" 119.3 . . ?
C7" C6" C5" 121.50(17) . . ?
C7" C6" H6" 119.3 . . ?
C5" C6" H6" 119.3 . . ?
C6" C7" C7A" 116.96(16) . . ?
C6" C7" H7" 121.5 . . ?
C7A" C7" H7" 121.5 . . ?
N1" C7A" C7" 129.62(15) . . ?
N1" C7A" C3A" 107.55(14) . . ?
C7" C7A" C3A" 122.79(15) . . ?

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
C11 N1 C2 C3 167.62(13) . . . . ?
C6 N1 C2 C3 -54.25(17) . . . . ?
C11 N1 C2 C21 -69.94(17) . . . . ?
C6 N1 C2 C21 68.19(18) . . . . ?
N1 C2 C3 C4 59.73(17) . . . . ?
C21 C2 C3 C4 -65.36(16) . . . . ?
C2 C3 C4 C3' 174.44(13) . . . . ?
C2 C3 C4 C5 -59.56(16) . . . . ?
C3' C4 C5 C6 -179.06(13) . . . . ?
C3 C4 C5 C6 55.59(17) . . . . ?
C11 N1 C6 C3" -56.77(18) . . . . ?
C2 N1 C6 C3" 167.03(14) . . . . ?
C11 N1 C6 C5 -176.38(14) . . . . ?
C2 N1 C6 C5 47.41(17) . . . . ?
C4 C5 C6 N1 -48.86(18) . . . . ?
C4 C5 C6 C3" -170.52(13) . . . . ?
C2 N1 C11 C12 112.34(17) . . . . ?
C6 N1 C11 C12 -25.1(2) . . . . ?
C2 N1 C11 C16 -67.12(19) . . . . ?
C6 N1 C11 C16 155.39(15) . . . . ?
C16 C11 C12 C13 1.8(3) . . . . ?
N1 C11 C12 C13 -177.70(16) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 1.9(3) . . . . ?
C12 C11 C16 C15 -2.9(3) . . . . ?
N1 C11 C16 C15 176.60(16) . . . . ?
N1 C2 C21 O21 -4.7(2) . . . . ?
C3 C2 C21 O21 119.27(18) . . . . ?
N1 C2 C21 O22 178.08(14) . . . . ?
C3 C2 C21 O22 -57.93(16) . . . . ?
O21 C21 O22 C22 -2.3(2) . . . . ?
C2 C21 O22 C22 174.95(14) . . . . ?
C21 O22 C22 C23 -174.09(16) . . . . ?
C7A' N1' C2' C3' 1.3(2) . . . . ?
N1' C2' C3' C3A' -0.79(19) . . . . ?
N1' C2' C3' C4 -177.65(15) . . . . ?
C5 C4 C3' C2' -40.7(2) . . . . ?
C3 C4 C3' C2' 82.0(2) . . . . ?
C5 C4 C3' C3A' 143.04(15) . . . . ?
C3 C4 C3' C3A' -94.34(18) . . . . ?
C2' C3' C3A' C4' -177.79(18) . . . . ?
C4 C3' C3A' C4' -0.8(3) . . . . ?
C2' C3' C3A' C7A' 0.02(18) . . . . ?
C4 C3' C3A' C7A' 177.03(15) . . . . ?
C7A' C3A' C4' C5' 0.5(2) . . . . ?
C3' C3A' C4' C5' 178.13(18) . . . . ?
C3A' C4' C5' C6' -1.0(3) . . . . ?
C4' C5' C6' C7' 0.7(3) . . . . ?
C5' C6' C7' C7A' 0.3(3) . . . . ?
C2' N1' C7A' C7' 177.12(18) . . . . ?
C2' N1' C7A' C3A' -1.24(19) . . . . ?
C6' C7' C7A' N1' -178.93(18) . . . . ?
C6' C7' C7A' C3A' -0.8(3) . . . . ?
C4' C3A' C7A' N1' 178.94(15) . . . . ?
C3' C3A' C7A' N1' 0.74(18) . . . . ?
C4' C3A' C7A' C7' 0.4(3) . . . . ?
C3' C3A' C7A' C7' -177.78(16) . . . . ?
C7A" N1" C2" C3" -1.0(2) . . . . ?
N1" C2" C3" C3A" 0.1(2) . . . . ?
N1" C2" C3" C6 171.40(15) . . . . ?
N1 C6 C3" C2" 131.29(17) . . . . ?
C5 C6 C3" C2" -107.27(19) . . . . ?
N1 C6 C3" C3A" -59.3(2) . . . . ?
C5 C6 C3" C3A" 62.1(2) . . . . ?
C2" C3" C3A" C4" 178.4(2) . . . . ?
C6 C3" C3A" C4" 7.4(3) . . . . ?
C2" C3" C3A" C7A" 0.73(18) . . . . ?
C6 C3" C3A" C7A" -170.28(16) . . . . ?
C7A" C3A" C4" C5" 1.8(3) . . . . ?
C3" C3A" C4" C5" -175.69(18) . . . . ?
C3A" C4" C5" C6" -0.5(3) . . . . ?
C4" C5" C6" C7" -1.1(3) . . . . ?
C5" C6" C7" C7A" 1.4(3) . . . . ?
C2" N1" C7A" C7" -176.28(17) . . . . ?
C2" N1" C7A" C3A" 1.46(19) . . . . ?
C6" C7" C7A" N1" 177.40(18) . . . . ?
C6" C7" C7A" C3A" 0.0(2) . . . . ?
C4" C3A" C7A" N1" -179.46(16) . . . . ?
C3" C3A" C7A" N1" -1.34(18) . . . . ?
C4" C3A" C7A" C7" -1.5(2) . . . . ?
C3" C3A" C7A" C7" 176.59(16) . . . . ?

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
N1' H1' O21 0.865(19) 2.07(2) 2.8977(19) 159(2) 1_556
N1" H1" N1' 0.895(19) 2.65(2) 3.298(2) 130.3(19) 1_545

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 977608'
