# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 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 
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_541rv1
_database_code_depnum_ccdc_archive 'CCDC 827474'
#TrackingRef '5633_web_deposit_cif_file_0_RossDavidJansen-vanVuuren_1306481695.archive.cif'
_audit_creation_date             2011-02-24T17:13:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         '(C31 H34 N2 O1),0.5(H2O) '
_chemical_formula_sum            'C31 H35 N2 O1.50'
_chemical_formula_weight         459.61
_chemical_compound_source        'synthesis as described'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   11.0893(19)
_cell_length_b                   15.523(2)
_cell_length_c                   15.895(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.150(17)
_cell_angle_gamma                90
_cell_volume                     2641.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1699
_cell_measurement_theta_min      4.0479
_cell_measurement_theta_max      62.6896
_cell_measurement_wavelength     1.5418
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988
_exptl_special_details           
;
?
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.63412
_exptl_absorpt_correction_T_max  1
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 16.0696
_diffrn_orient_matrix_ub_11      0.0963682
_diffrn_orient_matrix_ub_12      -0.0369271
_diffrn_orient_matrix_ub_13      0.0798038
_diffrn_orient_matrix_ub_21      0.1063427
_diffrn_orient_matrix_ub_22      0.026791
_diffrn_orient_matrix_ub_23      -0.0404066
_diffrn_orient_matrix_ub_31      0.0080689
_diffrn_orient_matrix_ub_32      0.088161
_diffrn_orient_matrix_ub_33      0.0458135
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_number            11637
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.05
_diffrn_reflns_theta_max         62.5
_diffrn_reflns_theta_full        62.5
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             4143
_reflns_number_gt                2009
_reflns_threshold_expression     >2sigma(I)
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4143
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   0.763
_refine_ls_restrained_S_all      0.763
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.029
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24281(19) 0.20611(12) 0.21647(13) 0.0579(5) Uani 1 1 d . . .
C2 C 0.19396(18) 0.11389(12) 0.20911(13) 0.0591(5) Uani 1 1 d . . .
C3 C 0.07076(19) 0.12328(13) 0.14167(14) 0.0618(5) Uani 1 1 d . . .
C4 C -0.0175(2) 0.06340(14) 0.10435(16) 0.0820(7) Uani 1 1 d . . .
H4 H -0.0066 0.0058 0.1206 0.098 Uiso 1 1 calc R . .
C5 C -0.1239(2) 0.08980(18) 0.04187(18) 0.0951(8) Uani 1 1 d . . .
H5 H -0.1849 0.0497 0.0164 0.114 Uiso 1 1 calc R . .
C6 C -0.1391(2) 0.17455(19) 0.01775(17) 0.0915(8) Uani 1 1 d . . .
H6 H -0.2106 0.191 -0.0243 0.11 Uiso 1 1 calc R . .
C7 C -0.0514(2) 0.23630(15) 0.05393(15) 0.0751(7) Uani 1 1 d . . .
H7 H -0.0622 0.2938 0.0372 0.09 Uiso 1 1 calc R . .
C8 C 0.05297(19) 0.20892(13) 0.11601(13) 0.0599(5) Uani 1 1 d . . .
C9 C 0.1669(2) 0.34960(12) 0.15122(15) 0.0779(7) Uani 1 1 d . . .
H9A H 0.1775 0.3775 0.2066 0.117 Uiso 1 1 calc R . .
H9B H 0.0929 0.3712 0.1109 0.117 Uiso 1 1 calc R . .
H9C H 0.2381 0.3612 0.1293 0.117 Uiso 1 1 calc R . .
C10 C 0.27916(19) 0.05056(12) 0.17654(14) 0.0737(7) Uani 1 1 d . . .
H10A H 0.3569 0.0445 0.2202 0.111 Uiso 1 1 calc R . .
H10B H 0.2947 0.0724 0.1238 0.111 Uiso 1 1 calc R . .
H10C H 0.2388 -0.0045 0.1653 0.111 Uiso 1 1 calc R . .
C11 C 0.1741(2) 0.08263(13) 0.29647(13) 0.0786(7) Uani 1 1 d . . .
H11A H 0.2537 0.0761 0.3381 0.118 Uiso 1 1 calc R . .
H11B H 0.1314 0.0282 0.2881 0.118 Uiso 1 1 calc R . .
H11C H 0.1249 0.1241 0.3177 0.118 Uiso 1 1 calc R . .
C12 C 0.35194(19) 0.23779(13) 0.26663(14) 0.0669(6) Uani 1 1 d . . .
H12 H 0.3626 0.2972 0.2662 0.08 Uiso 1 1 calc R . .
C13 C 0.45195(19) 0.18906(13) 0.31997(13) 0.0665(6) Uani 1 1 d . . .
H13 H 0.441 0.1298 0.3222 0.08 Uiso 1 1 calc R . .
C14 C 0.56075(19) 0.22175(13) 0.36735(13) 0.0631(6) Uani 1 1 d . . .
C15 C 0.5974(2) 0.31489(13) 0.37789(15) 0.0733(6) Uani 1 1 d . . .
H15A H 0.5363 0.3477 0.3986 0.088 Uiso 1 1 calc R . .
H15B H 0.6033 0.339 0.3228 0.088 Uiso 1 1 calc R . .
C16 C 0.7245(2) 0.31711(13) 0.44472(15) 0.0737(6) Uani 1 1 d . . .
H16A H 0.7841 0.3497 0.4225 0.088 Uiso 1 1 calc R . .
H16B H 0.7175 0.3435 0.4986 0.088 Uiso 1 1 calc R . .
C17 C 0.76487(19) 0.22485(13) 0.45970(14) 0.0642(6) Uani 1 1 d . . .
C18 C 0.6636(2) 0.16842(14) 0.41495(14) 0.0674(6) Uani 1 1 d . . .
C19 C 0.87538(19) 0.19527(13) 0.50797(13) 0.0667(6) Uani 1 1 d . . .
H19 H 0.8892 0.1362 0.5076 0.08 Uiso 1 1 calc R . .
C20 C 0.97259(19) 0.24709(13) 0.55951(14) 0.0680(6) Uani 1 1 d . . .
H20 H 0.9575 0.3061 0.5589 0.082 Uiso 1 1 calc R . .
C21 C 1.08494(19) 0.22033(12) 0.60951(14) 0.0586(5) Uani 1 1 d . . .
C22 C 1.14334(18) 0.13031(12) 0.61679(13) 0.0582(5) Uani 1 1 d . . .
C23 C 1.26489(18) 0.14472(12) 0.68532(13) 0.0584(5) Uani 1 1 d . . .
C24 C 1.3570(2) 0.08821(14) 0.72384(15) 0.0744(6) Uani 1 1 d . . .
H24 H 1.3525 0.0307 0.7068 0.089 Uiso 1 1 calc R . .
C25 C 1.4579(2) 0.11804(16) 0.78900(16) 0.0823(7) Uani 1 1 d . . .
H25 H 1.5207 0.0801 0.8165 0.099 Uiso 1 1 calc R . .
C26 C 1.4654(2) 0.20336(17) 0.81308(15) 0.0803(7) Uani 1 1 d . . .
H26 H 1.5336 0.2221 0.8568 0.096 Uiso 1 1 calc R . .
C27 C 1.37416(19) 0.26182(14) 0.77408(14) 0.0690(6) Uani 1 1 d . . .
H27 H 1.38 0.3196 0.7901 0.083 Uiso 1 1 calc R . .
C28 C 1.27380(18) 0.23085(12) 0.71029(14) 0.0583(5) Uani 1 1 d . . .
C29 C 1.1492(2) 0.36654(12) 0.67252(15) 0.0790(7) Uani 1 1 d . . .
H29A H 1.1358 0.3942 0.6168 0.119 Uiso 1 1 calc R . .
H29B H 1.2214 0.3909 0.7124 0.119 Uiso 1 1 calc R . .
H29C H 1.0774 0.3751 0.6946 0.119 Uiso 1 1 calc R . .
C30 C 1.1665(2) 0.10411(13) 0.52894(13) 0.0743(6) Uani 1 1 d . . .
H30A H 1.0879 0.0956 0.4868 0.111 Uiso 1 1 calc R . .
H30B H 1.2137 0.0515 0.536 0.111 Uiso 1 1 calc R . .
H30C H 1.2124 0.1488 0.5093 0.111 Uiso 1 1 calc R . .
C31 C 1.0667(2) 0.06020(12) 0.64777(14) 0.0782(7) Uani 1 1 d . . .
H31A H 0.9898 0.051 0.604 0.117 Uiso 1 1 calc R . .
H31B H 1.0488 0.0783 0.701 0.117 Uiso 1 1 calc R . .
H31C H 1.1137 0.0075 0.6576 0.117 Uiso 1 1 calc R . .
N1 N 0.15498(15) 0.25691(9) 0.16166(11) 0.0615(5) Uani 1 1 d . . .
N2 N 1.16868(15) 0.27483(9) 0.66299(11) 0.0626(5) Uani 1 1 d . . .
O1 O 0.66473(14) 0.08853(10) 0.41760(11) 0.0935(5) Uani 1 1 d . . .
O2 O -0.0526(4) 0.4690(3) -0.0231(3) 0.173(2) Uani 0.5 1 d P . .
H2A H -0.0683 0.5137 0.0105 0.208 Uiso 0.5 1 d PR . .
H2B H -0.0033 0.4906 -0.0581 0.208 Uiso 0.5 1 d PR . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0630(13) 0.0558(12) 0.0574(14) 0.0025(11) 0.0199(12) 0.0075(11)
C2 0.0641(13) 0.0520(11) 0.0635(14) 0.0027(10) 0.0205(11) 0.0032(10)
C3 0.0619(13) 0.0600(13) 0.0650(14) -0.0063(11) 0.0190(11) 0.0003(11)
C4 0.0804(17) 0.0700(14) 0.0954(19) -0.0111(14) 0.0226(16) -0.0033(14)
C5 0.0745(18) 0.104(2) 0.100(2) -0.0303(17) 0.0116(16) -0.0090(16)
C6 0.0715(17) 0.113(2) 0.0837(19) -0.0120(17) 0.0099(14) 0.0173(16)
C7 0.0680(15) 0.0843(16) 0.0723(17) -0.0035(13) 0.0171(13) 0.0120(14)
C8 0.0587(13) 0.0641(14) 0.0582(14) 0.0002(11) 0.0176(11) 0.0092(11)
C9 0.0872(16) 0.0555(13) 0.0914(18) 0.0067(12) 0.0241(14) 0.0071(12)
C10 0.0821(15) 0.0606(13) 0.0769(16) -0.0013(12) 0.0180(13) 0.0125(12)
C11 0.0866(16) 0.0814(15) 0.0722(17) 0.0130(13) 0.0287(13) -0.0016(12)
C12 0.0676(14) 0.0583(12) 0.0733(16) 0.0009(11) 0.0159(13) 0.0011(11)
C13 0.0716(15) 0.0605(13) 0.0662(15) -0.0034(11) 0.0160(12) 0.0019(12)
C14 0.0626(14) 0.0636(13) 0.0622(15) -0.0041(11) 0.0145(12) 0.0007(11)
C15 0.0747(15) 0.0630(13) 0.0823(16) 0.0016(12) 0.0208(13) -0.0007(11)
C16 0.0731(15) 0.0688(14) 0.0801(17) -0.0113(12) 0.0217(13) -0.0061(11)
C17 0.0639(14) 0.0641(13) 0.0635(15) -0.0059(11) 0.0148(12) -0.0026(12)
C18 0.0712(14) 0.0603(14) 0.0661(13) -0.0061(12) 0.0101(11) 0.0011(12)
C19 0.0683(14) 0.0679(13) 0.0645(15) -0.0069(12) 0.0185(12) -0.0046(12)
C20 0.0679(15) 0.0618(13) 0.0739(16) -0.0104(11) 0.0179(13) -0.0052(11)
C21 0.0591(13) 0.0576(12) 0.0615(14) -0.0112(11) 0.0199(11) -0.0108(11)
C22 0.0647(14) 0.0528(11) 0.0585(13) -0.0083(10) 0.0186(11) -0.0110(10)
C23 0.0622(13) 0.0563(13) 0.0590(13) -0.0068(11) 0.0199(11) -0.0066(11)
C24 0.0776(16) 0.0640(13) 0.0795(17) -0.0042(13) 0.0167(14) -0.0012(13)
C25 0.0732(16) 0.0880(18) 0.0836(18) -0.0018(15) 0.0166(14) 0.0078(14)
C26 0.0626(15) 0.0996(19) 0.0757(17) -0.0142(15) 0.0127(13) -0.0102(14)
C27 0.0681(14) 0.0705(14) 0.0701(16) -0.0149(12) 0.0209(12) -0.0138(12)
C28 0.0561(13) 0.0604(12) 0.0614(14) -0.0086(11) 0.0206(12) -0.0097(11)
C29 0.0795(16) 0.0555(13) 0.1013(19) -0.0145(13) 0.0222(14) -0.0029(12)
C30 0.0845(16) 0.0700(13) 0.0685(15) -0.0165(12) 0.0203(13) -0.0016(12)
C31 0.0866(16) 0.0691(14) 0.0774(17) -0.0023(12) 0.0184(13) -0.0262(12)
N1 0.0649(11) 0.0501(9) 0.0692(12) 0.0044(9) 0.0168(10) 0.0063(9)
N2 0.0621(11) 0.0514(9) 0.0734(13) -0.0140(9) 0.0162(10) -0.0077(9)
O1 0.0882(11) 0.0620(10) 0.1114(13) -0.0055(9) -0.0074(9) 0.0014(8)
O2 0.149(4) 0.152(4) 0.214(6) -0.065(4) 0.039(4) 0.020(3)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_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 C12 1.356(3) . ?
C1 N1 1.373(2) . ?
C1 C2 1.524(3) . ?
C2 C3 1.507(3) . ?
C2 C11 1.540(3) . ?
C2 C10 1.544(3) . ?
C3 C4 1.368(3) . ?
C3 C8 1.389(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.368(3) . ?
C6 C7 1.379(3) . ?
C7 C8 1.377(3) . ?
C8 N1 1.390(2) . ?
C9 N1 1.458(2) . ?
C12 C13 1.425(3) . ?
C13 C14 1.344(2) . ?
C14 C18 1.451(3) . ?
C14 C15 1.499(3) . ?
C15 C16 1.528(3) . ?
C16 C17 1.501(3) . ?
C17 C19 1.345(3) . ?
C17 C18 1.455(3) . ?
C18 O1 1.241(2) . ?
C19 C20 1.421(3) . ?
C20 C21 1.356(3) . ?
C21 N2 1.374(2) . ?
C21 C22 1.532(3) . ?
C22 C23 1.512(3) . ?
C22 C31 1.539(3) . ?
C22 C30 1.539(3) . ?
C23 C24 1.364(3) . ?
C23 C28 1.391(2) . ?
C24 C25 1.390(3) . ?
C25 C26 1.375(3) . ?
C26 C27 1.379(3) . ?
C27 C28 1.381(3) . ?
C28 N2 1.390(2) . ?
C29 N2 1.454(2) . ?
O2 O2 1.542(7) 3_565 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 N1 122.74(18) . . ?
C12 C1 C2 129.10(18) . . ?
N1 C1 C2 108.16(16) . . ?
C3 C2 C1 101.64(16) . . ?
C3 C2 C11 110.81(17) . . ?
C1 C2 C11 110.99(17) . . ?
C3 C2 C10 110.10(16) . . ?
C1 C2 C10 112.80(17) . . ?
C11 C2 C10 110.23(17) . . ?
C4 C3 C8 119.5(2) . . ?
C4 C3 C2 130.98(19) . . ?
C8 C3 C2 109.52(17) . . ?
C3 C4 C5 119.1(2) . . ?
C6 C5 C4 120.2(2) . . ?
C5 C6 C7 122.0(2) . . ?
C8 C7 C6 116.9(2) . . ?
C7 C8 C3 122.3(2) . . ?
C7 C8 N1 128.72(19) . . ?
C3 C8 N1 109.01(17) . . ?
C1 C12 C13 126.43(19) . . ?
C14 C13 C12 125.3(2) . . ?
C13 C14 C18 123.00(19) . . ?
C13 C14 C15 127.16(19) . . ?
C18 C14 C15 109.82(17) . . ?
C14 C15 C16 105.85(17) . . ?
C17 C16 C15 105.77(17) . . ?
C19 C17 C18 123.03(19) . . ?
C19 C17 C16 127.29(19) . . ?
C18 C17 C16 109.67(18) . . ?
O1 C18 C14 126.0(2) . . ?
O1 C18 C17 125.8(2) . . ?
C14 C18 C17 108.20(18) . . ?
C17 C19 C20 125.2(2) . . ?
C21 C20 C19 127.36(19) . . ?
C20 C21 N2 122.87(18) . . ?
C20 C21 C22 129.00(18) . . ?
N2 C21 C22 108.11(16) . . ?
C23 C22 C21 101.49(15) . . ?
C23 C22 C31 109.70(16) . . ?
C21 C22 C31 114.29(17) . . ?
C23 C22 C30 111.33(17) . . ?
C21 C22 C30 109.88(17) . . ?
C31 C22 C30 109.92(16) . . ?
C24 C23 C28 120.06(19) . . ?
C24 C23 C22 130.56(18) . . ?
C28 C23 C22 109.35(17) . . ?
C23 C24 C25 118.9(2) . . ?
C26 C25 C24 120.4(2) . . ?
C25 C26 C27 121.7(2) . . ?
C26 C27 C28 117.1(2) . . ?
C27 C28 N2 128.82(18) . . ?
C27 C28 C23 121.8(2) . . ?
N2 C28 C23 109.32(17) . . ?
C1 N1 C8 111.65(15) . . ?
C1 N1 C9 124.64(17) . . ?
C8 N1 C9 123.70(17) . . ?
C21 N2 C28 111.58(16) . . ?
C21 N2 C29 124.92(17) . . ?
C28 N2 C29 123.46(17) . . ?
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
C12 C1 C2 C3 -178.9(2) . . . . ?
N1 C1 C2 C3 1.3(2) . . . . ?
C12 C1 C2 C11 63.3(3) . . . . ?
N1 C1 C2 C11 -116.56(19) . . . . ?
C12 C1 C2 C10 -61.0(3) . . . . ?
N1 C1 C2 C10 119.17(18) . . . . ?
C1 C2 C3 C4 178.1(2) . . . . ?
C11 C2 C3 C4 -63.9(3) . . . . ?
C10 C2 C3 C4 58.3(3) . . . . ?
C1 C2 C3 C8 -0.7(2) . . . . ?
C11 C2 C3 C8 117.35(19) . . . . ?
C10 C2 C3 C8 -120.44(19) . . . . ?
C8 C3 C4 C5 -0.5(3) . . . . ?
C2 C3 C4 C5 -179.2(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
C6 C7 C8 N1 179.3(2) . . . . ?
C4 C3 C8 C7 0.2(3) . . . . ?
C2 C3 C8 C7 179.12(19) . . . . ?
C4 C3 C8 N1 -179.2(2) . . . . ?
C2 C3 C8 N1 -0.2(2) . . . . ?
N1 C1 C12 C13 -174.8(2) . . . . ?
C2 C1 C12 C13 5.4(4) . . . . ?
C1 C12 C13 C14 178.1(2) . . . . ?
C12 C13 C14 C18 -174.8(2) . . . . ?
C12 C13 C14 C15 3.3(4) . . . . ?
C13 C14 C15 C16 174.8(2) . . . . ?
C18 C14 C15 C16 -6.9(2) . . . . ?
C14 C15 C16 C17 8.4(2) . . . . ?
C15 C16 C17 C19 174.1(2) . . . . ?
C15 C16 C17 C18 -7.2(2) . . . . ?
C13 C14 C18 O1 0.5(4) . . . . ?
C15 C14 C18 O1 -177.9(2) . . . . ?
C13 C14 C18 C17 -179.1(2) . . . . ?
C15 C14 C18 C17 2.5(3) . . . . ?
C19 C17 C18 O1 2.2(4) . . . . ?
C16 C17 C18 O1 -176.5(2) . . . . ?
C19 C17 C18 C14 -178.2(2) . . . . ?
C16 C17 C18 C14 3.1(3) . . . . ?
C18 C17 C19 C20 -173.7(2) . . . . ?
C16 C17 C19 C20 4.8(4) . . . . ?
C17 C19 C20 C21 179.6(2) . . . . ?
C19 C20 C21 N2 -174.2(2) . . . . ?
C19 C20 C21 C22 7.2(4) . . . . ?
C20 C21 C22 C23 -178.0(2) . . . . ?
N2 C21 C22 C23 3.3(2) . . . . ?
C20 C21 C22 C31 -60.0(3) . . . . ?
N2 C21 C22 C31 121.30(18) . . . . ?
C20 C21 C22 C30 64.1(3) . . . . ?
N2 C21 C22 C30 -114.59(18) . . . . ?
C21 C22 C23 C24 176.7(2) . . . . ?
C31 C22 C23 C24 55.4(3) . . . . ?
C30 C22 C23 C24 -66.5(3) . . . . ?
C21 C22 C23 C28 -1.5(2) . . . . ?
C31 C22 C23 C28 -122.78(19) . . . . ?
C30 C22 C23 C28 115.33(19) . . . . ?
C28 C23 C24 C25 1.1(3) . . . . ?
C22 C23 C24 C25 -176.9(2) . . . . ?
C23 C24 C25 C26 -1.0(4) . . . . ?
C24 C25 C26 C27 0.1(4) . . . . ?
C25 C26 C27 C28 0.8(3) . . . . ?
C26 C27 C28 N2 178.0(2) . . . . ?
C26 C27 C28 C23 -0.7(3) . . . . ?
C24 C23 C28 C27 -0.3(3) . . . . ?
C22 C23 C28 C27 178.16(19) . . . . ?
C24 C23 C28 N2 -179.18(19) . . . . ?
C22 C23 C28 N2 -0.8(2) . . . . ?
C12 C1 N1 C8 178.6(2) . . . . ?
C2 C1 N1 C8 -1.6(2) . . . . ?
C12 C1 N1 C9 -0.7(3) . . . . ?
C2 C1 N1 C9 179.17(18) . . . . ?
C7 C8 N1 C1 -178.1(2) . . . . ?
C3 C8 N1 C1 1.2(2) . . . . ?
C7 C8 N1 C9 1.1(3) . . . . ?
C3 C8 N1 C9 -179.59(19) . . . . ?
C20 C21 N2 C28 177.1(2) . . . . ?
C22 C21 N2 C28 -4.1(2) . . . . ?
C20 C21 N2 C29 -0.5(3) . . . . ?
C22 C21 N2 C29 178.31(19) . . . . ?
C27 C28 N2 C21 -175.7(2) . . . . ?
C23 C28 N2 C21 3.1(2) . . . . ?
C27 C28 N2 C29 1.9(3) . . . . ?
C23 C28 N2 C29 -179.25(19) . . . . ?