# 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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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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#
data_1

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   21.828(4)
_cell_length_b                   9.4747(16)
_cell_length_c                   22.495(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.114(10)
_cell_angle_gamma                90
_cell_volume                     4633.8(13)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C96 H124 N12 
# Dc =      1.04 Fooo =   1736.00 Mu =      0.61 M =    723.06
# Found Formula = C108 H136 N12 
# Dc =      1.15 FOOO =   1736.00 Mu =      0.67 M =    801.17

_chemical_formula_sum            'C108 H136 N12'
_chemical_formula_moiety         'C96 H124 N12, 2(C6 H6)'
_chemical_compound_source        ?
_chemical_formula_weight         1602.35


_cell_measurement_reflns_used    5218
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.060
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_max          0.270

_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1736
_exptl_absorpt_coefficient_mu    0.067

# Sheldrick geometric approximatio 0.99 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            53279
_reflns_number_total             9461
_diffrn_reflns_av_R_equivalents  0.148
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 9461 
# Theoretical number of reflections is about 18975 


_diffrn_reflns_theta_min         1.818
_diffrn_reflns_theta_max         26.391
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        26.391
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              -27
_reflns_limit_h_max              27
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   2.36
_oxford_diffrn_Wilson_scale      175.44

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.37
_refine_diff_density_max         0.54


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>1.0\s(I)
_refine_ls_number_reflns         4724
_refine_ls_number_restraints     1047
_refine_ls_number_parameters     596
_oxford_refine_ls_R_factor_ref   0.0836
_refine_ls_wR_factor_ref         0.0778
_refine_ls_goodness_of_fit_ref   1.0530
_refine_ls_shift/su_max          0.0083618
_refine_ls_shift/su_mean         0.0000824


# The values computed from all data 
_oxford_reflns_number_all        9419
_refine_ls_R_factor_all          0.1755
_refine_ls_wR_factor_all         0.1986

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3424
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_gt          0.0657

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.482 0.510 0.218 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.28566(13) -0.3722(3) 0.74407(12) 0.0257 1.0000 Uani . . . . . .
N2 N 0.30535(14) -0.3499(4) 0.49921(13) 0.0345 1.0000 Uani . . . . . .
N3 N 0.26888(15) -0.4252(4) 0.46641(13) 0.0357 1.0000 Uani . . . . . .
N4 N 0.29728(14) -0.4156(3) 0.22350(12) 0.0275 1.0000 Uani . . . . . .
N5 N 0.49215(15) -0.0351(3) 0.24945(13) 0.0324 1.0000 Uani . . . . . .
N6 N 0.51554(14) 0.0095(3) 0.20496(13) 0.0319 1.0000 Uani . . . . . .
C1 C 0.43413(16) -0.1051(4) 0.78032(15) 0.0274 1.0000 Uani . . . . . .
C2 C 0.40639(16) -0.1599(4) 0.82859(15) 0.0288 1.0000 Uani . . . . . .
C3 C 0.35695(17) -0.2493(4) 0.82153(15) 0.0311 1.0000 Uani . . . . . .
C4 C 0.33433(16) -0.2854(4) 0.76329(15) 0.0276 1.0000 Uani . . . . . .
C5 C 0.36342(16) -0.2346(4) 0.71340(15) 0.0262 1.0000 Uani . . . . . .
C6 C 0.41300(16) -0.1427(4) 0.72192(15) 0.0278 1.0000 Uani . . . . . .
C7 C 0.29498(17) -0.3620(4) 0.56144(15) 0.0303 1.0000 Uani . . . . . .
C8 C 0.24838(18) -0.4451(4) 0.58247(15) 0.0329 1.0000 Uani . . . . . .
C9 C 0.24068(18) -0.4546(4) 0.64308(15) 0.0325 1.0000 Uani . . . . . .
C10 C 0.28217(17) -0.3788(4) 0.68211(15) 0.0279 1.0000 Uani . . . . . .
C11 C 0.32989(16) -0.2951(4) 0.66168(15) 0.0274 1.0000 Uani . . . . . .
C12 C 0.33543(17) -0.2873(4) 0.60013(15) 0.0292 1.0000 Uani . . . . . .
C13 C 0.27777(18) -0.4160(4) 0.40405(15) 0.0312 1.0000 Uani . . . . . .
C14 C 0.23682(18) -0.4971(4) 0.36816(16) 0.0350 1.0000 Uani . . . . . .
C15 C 0.23879(18) -0.5036(4) 0.30728(16) 0.0329 1.0000 Uani . . . . . .
C16 C 0.28432(16) -0.4256(4) 0.28275(14) 0.0262 1.0000 Uani . . . . . .
C17 C 0.32641(16) -0.3400(4) 0.31828(15) 0.0277 1.0000 Uani . . . . . .
C18 C 0.32262(17) -0.3353(4) 0.37975(15) 0.0313 1.0000 Uani . . . . . .
C19 C 0.44172(17) -0.1328(4) 0.23668(16) 0.0295 1.0000 Uani . . . . . .
C20 C 0.42165(17) -0.1818(4) 0.17902(16) 0.0308 1.0000 Uani . . . . . .
C21 C 0.37407(16) -0.2769(4) 0.17047(15) 0.0281 1.0000 Uani . . . . . .
C22 C 0.34570(16) -0.3237(4) 0.22008(15) 0.0278 1.0000 Uani . . . . . .
C23 C 0.36584(16) -0.2735(4) 0.27831(15) 0.0271 1.0000 Uani . . . . . .
C24 C 0.41448(17) -0.1790(4) 0.28575(15) 0.0289 1.0000 Uani . . . . . .
C25 C 0.24095(17) -0.4317(4) 0.78201(15) 0.0298 1.0000 Uani . . . . . .
C26 C 0.19159(17) -0.3261(4) 0.79589(15) 0.0326 1.0000 Uani . . . . . .
C27 C 0.15472(17) -0.2671(4) 0.74080(16) 0.0317 1.0000 Uani . . . . . .
C28 C 0.10258(18) -0.1682(4) 0.75375(15) 0.0341 1.0000 Uani . . . . . .
C29 C 0.06836(17) -0.1093(4) 0.69689(15) 0.0315 1.0000 Uani . . . . . .
C30 C 0.01680(18) -0.0076(4) 0.70787(16) 0.0326 1.0000 Uani . . . . . .
C31 C -0.01666(18) 0.0507(4) 0.65027(16) 0.0338 1.0000 Uani . . . . . .
C32 C -0.06802(17) 0.1528(4) 0.66135(16) 0.0341 1.0000 Uani . . . . . .
C33 C -0.10563(19) 0.2056(5) 0.60489(17) 0.0408 1.0000 Uani . . . . . .
C34 C -0.0678(2) 0.2799(5) 0.56086(19) 0.0510 1.0000 Uani . . . . . .
C35 C -0.1082(2) 0.3473(6) 0.5096(2) 0.0614 1.0000 Uani . . . . . .
C36 C -0.0729(3) 0.3933(8) 0.4575(2) 0.1008 1.0000 Uani . . . . . .
C37 C 0.26370(18) -0.4880(4) 0.17286(15) 0.0339 1.0000 Uani . . . . . .
C38 C 0.21615(18) -0.3941(5) 0.13823(16) 0.0394 1.0000 Uani . . . . . .
C39 C 0.16610(18) -0.3378(5) 0.17425(16) 0.0406 1.0000 Uani . . . . . .
C40 C 0.11720(19) -0.2551(5) 0.13609(17) 0.0462 1.0000 Uani . . . . . .
C41 C 0.0652(2) -0.2038(6) 0.1699(2) 0.0628 1.0000 Uani . . . . . .
C42 C 0.0097(2) -0.1411(5) 0.13134(19) 0.0570 1.0000 Uani D U . . . .
C43 C 0.0192(4) 0.0111(8) 0.1160(5) 0.0642 0.5219(15) Uani D U P 1 1 .
C44 C -0.0397(4) 0.0784(7) 0.0836(4) 0.0563 0.5219(15) Uani D U P 1 1 .
C45 C -0.0257(4) 0.2380(8) 0.0792(4) 0.0820 0.5219(15) Uani D U P 1 1 .
C46 C -0.0748(5) 0.321(1) 0.0422(6) 0.1088 0.5219(15) Uani D U P 1 1 .
C47 C -0.0527(7) 0.4793(9) 0.0432(5) 0.1137 0.5219(15) Uani D U P 1 1 .
C48 C -0.0851(7) 0.5597(11) -0.0080(5) 0.1109 0.5219(15) Uani D U P 1 1 .
C49 C 0.1627(4) -0.7636(6) 0.5005(2) 0.0744 1.0000 Uani . . . . . .
C50 C 0.1127(3) -0.8461(7) 0.5142(2) 0.0779 1.0000 Uani . . . . . .
C51 C 0.1251(3) -0.9773(7) 0.5421(2) 0.0709 1.0000 Uani . . . . . .
C52 C 0.1854(3) -1.0192(6) 0.5552(2) 0.0701 1.0000 Uani . . . . . .
C53 C 0.2319(3) -0.9381(8) 0.5416(2) 0.0824 1.0000 Uani . . . . . .
C54 C 0.2206(3) -0.8109(7) 0.5143(2) 0.0769 1.0000 Uani . . . . . .
H21 H 0.4213 -0.1333 0.8669 0.0339 1.0000 Uiso R . . . . .
H31 H 0.3389 -0.2850 0.8545 0.0330 1.0000 Uiso R . . . . .
H61 H 0.4320 -0.1077 0.6896 0.0297 1.0000 Uiso R . . . . .
H81 H 0.2223 -0.4960 0.5558 0.0371 1.0000 Uiso R . . . . .
H91 H 0.2088 -0.5090 0.6573 0.0358 1.0000 Uiso R . . . . .
H121 H 0.3671 -0.2336 0.5855 0.0339 1.0000 Uiso R . . . . .
H141 H 0.2066 -0.5490 0.3859 0.0399 1.0000 Uiso R . . . . .
H151 H 0.2104 -0.5567 0.2832 0.0350 1.0000 Uiso R . . . . .
H181 H 0.3496 -0.2799 0.4036 0.0349 1.0000 Uiso R . . . . .
H201 H 0.4408 -0.1493 0.1467 0.0359 1.0000 Uiso R . . . . .
H211 H 0.3606 -0.3100 0.1326 0.0327 1.0000 Uiso R . . . . .
H241 H 0.4286 -0.1448 0.3240 0.0322 1.0000 Uiso R . . . . .
H251 H 0.2633 -0.4646 0.8187 0.0308 1.0000 Uiso R . . . . .
H252 H 0.2198 -0.5111 0.7614 0.0315 1.0000 Uiso R . . . . .
H261 H 0.1627 -0.3734 0.8197 0.0359 1.0000 Uiso R . . . . .
H262 H 0.2115 -0.2476 0.8187 0.0360 1.0000 Uiso R . . . . .
H272 H 0.1381 -0.3462 0.7172 0.0351 1.0000 Uiso R . . . . .
H271 H 0.1829 -0.2147 0.7176 0.0349 1.0000 Uiso R . . . . .
H282 H 0.0738 -0.2188 0.7763 0.0409 1.0000 Uiso R . . . . .
H281 H 0.1198 -0.0896 0.7775 0.0406 1.0000 Uiso R . . . . .
H291 H 0.0508 -0.1875 0.6733 0.0352 1.0000 Uiso R . . . . .
H292 H 0.0983 -0.0605 0.6747 0.0349 1.0000 Uiso R . . . . .
H301 H -0.0130 -0.0556 0.7298 0.0358 1.0000 Uiso R . . . . .
H302 H 0.0342 0.0719 0.7312 0.0359 1.0000 Uiso R . . . . .
H311 H -0.0345 -0.0284 0.6275 0.0390 1.0000 Uiso R . . . . .
H312 H 0.0133 0.0979 0.6277 0.0388 1.0000 Uiso R . . . . .
H322 H -0.0958 0.1058 0.6862 0.0379 1.0000 Uiso R . . . . .
H321 H -0.0499 0.2331 0.6832 0.0382 1.0000 Uiso R . . . . .
H332 H -0.1364 0.2714 0.6170 0.0500 1.0000 Uiso R . . . . .
H331 H -0.1263 0.1247 0.5847 0.0502 1.0000 Uiso R . . . . .
H341 H -0.0431 0.3535 0.5822 0.0591 1.0000 Uiso R . . . . .
H342 H -0.0406 0.2118 0.5440 0.0589 1.0000 Uiso R . . . . .
H351 H -0.1290 0.4294 0.5249 0.0709 1.0000 Uiso R . . . . .
H352 H -0.1390 0.2778 0.4945 0.0714 1.0000 Uiso R . . . . .
H361 H -0.1013 0.4194 0.4239 0.1490 1.0000 Uiso R . . . . .
H362 H -0.0473 0.4734 0.4702 0.1490 1.0000 Uiso R . . . . .
H363 H -0.0470 0.3165 0.4468 0.1490 1.0000 Uiso R . . . . .
H371 H 0.2938 -0.5205 0.1462 0.0386 1.0000 Uiso R . . . . .
H372 H 0.2422 -0.5692 0.1880 0.0388 1.0000 Uiso R . . . . .
H381 H 0.2371 -0.3140 0.1217 0.0470 1.0000 Uiso R . . . . .
H382 H 0.1959 -0.4511 0.1060 0.0472 1.0000 Uiso R . . . . .
H392 H 0.1463 -0.4168 0.1925 0.0449 1.0000 Uiso R . . . . .
H391 H 0.1848 -0.2751 0.2054 0.0449 1.0000 Uiso R . . . . .
H402 H 0.0990 -0.3186 0.1054 0.0520 1.0000 Uiso R . . . . .
H401 H 0.1369 -0.1744 0.1178 0.0522 1.0000 Uiso R . . . . .
H411 H 0.0493 -0.2850 0.1902 0.0742 1.0000 Uiso R . . . . .
H412 H 0.0817 -0.1330 0.1987 0.0743 1.0000 Uiso R . . . . .
H421 H -0.0247 -0.1285 0.1556 0.0680 1.0000 Uiso R . . . . .
H422 H -0.0024 -0.2053 0.0986 0.0681 1.0000 Uiso R . . . . .
H432 H 0.0306 0.0622 0.1528 0.0661 0.5219(15) Uiso R . P 1 1 .
H431 H 0.0525 0.0160 0.0900 0.0663 0.5219(15) Uiso R . P 1 1 .
H441 H -0.0745 0.0595 0.1059 0.0562 0.5219(15) Uiso R . P 1 1 .
H442 H -0.0487 0.0417 0.0438 0.0563 0.5219(15) Uiso R . P 1 1 .
H451 H -0.0242 0.2777 0.1193 0.0871 0.5219(15) Uiso R . P 1 1 .
H452 H 0.0138 0.2500 0.0631 0.0871 0.5219(15) Uiso R . P 1 1 .
H461 H -0.1156 0.3087 0.0557 0.1070 0.5219(15) Uiso R . P 1 1 .
H462 H -0.0748 0.2845 0.0018 0.1072 0.5219(15) Uiso R . P 1 1 .
H472 H -0.0616 0.5219 0.0805 0.1131 0.5219(15) Uiso R . P 1 1 .
H471 H -0.0089 0.4854 0.0393 0.1129 0.5219(15) Uiso R . P 1 1 .
H482 H -0.0804 0.6592 -0.0002 0.1431 0.5219(15) Uiso R . P 1 1 .
H481 H -0.1281 0.5337 -0.0107 0.1432 0.5219(15) Uiso R . P 1 1 .
H483 H -0.0669 0.5355 -0.0442 0.1431 0.5219(15) Uiso R . P 1 1 .
H491 H 0.1560 -0.6758 0.4817 0.0842 1.0000 Uiso R . . . . .
H501 H 0.0724 -0.8145 0.5056 0.0939 1.0000 Uiso R . . . . .
H511 H 0.0926 -1.0364 0.5504 0.0791 1.0000 Uiso R . . . . .
H521 H 0.1934 -1.1057 0.5748 0.0832 1.0000 Uiso R . . . . .
H531 H 0.2728 -0.9700 0.5502 0.1021 1.0000 Uiso R . . . . .
H541 H 0.2541 -0.7552 0.5051 0.0910 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.07978(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C4 . 1.382(5) yes
N1 . C10 . 1.391(4) yes
N1 . C25 . 1.465(4) yes
N2 . N3 . 1.258(4) yes
N2 . C7 . 1.442(4) yes
N3 . C13 . 1.436(4) yes
N4 . C16 . 1.390(4) yes
N4 . C22 . 1.377(5) yes
N4 . C37 . 1.469(4) yes
N5 . N6 . 1.238(4) yes
N5 . C19 . 1.447(5) yes
N6 . C1 2_656 1.439(5) yes
C1 . C2 . 1.390(5) yes
C1 . C6 . 1.399(5) yes
C2 . C3 . 1.370(5) yes
C2 . H21 . 0.929 no
C3 . C4 . 1.401(5) yes
C3 . H31 . 0.933 no
C4 . C5 . 1.422(5) yes
C5 . C6 . 1.389(5) yes
C5 . C11 . 1.437(5) yes
C6 . H61 . 0.930 no
C7 . C8 . 1.402(5) yes
C7 . C12 . 1.379(5) yes
C8 . C9 . 1.391(5) yes
C8 . H81 . 0.925 no
C9 . C10 . 1.402(5) yes
C9 . H91 . 0.944 no
C10 . C11 . 1.418(5) yes
C11 . C12 . 1.403(5) yes
C12 . H121 . 0.941 no
C13 . C14 . 1.383(5) yes
C13 . C18 . 1.392(5) yes
C14 . C15 . 1.375(5) yes
C14 . H141 . 0.940 no
C15 . C16 . 1.391(5) yes
C15 . H151 . 0.933 no
C16 . C17 . 1.417(5) yes
C17 . C18 . 1.393(5) yes
C17 . C23 . 1.444(5) yes
C18 . H181 . 0.925 no
C19 . C20 . 1.410(5) yes
C19 . C24 . 1.371(5) yes
C20 . C21 . 1.376(5) yes
C20 . H201 . 0.922 no
C21 . C22 . 1.396(5) yes
C21 . H211 . 0.931 no
C22 . C23 . 1.426(5) yes
C23 . C24 . 1.387(5) yes
C24 . H241 . 0.946 no
C25 . C26 . 1.523(5) yes
C25 . H251 . 0.971 no
C25 . H252 . 0.978 no
C26 . C27 . 1.523(5) yes
C26 . H261 . 0.973 no
C26 . H262 . 0.983 no
C27 . C28 . 1.523(5) yes
C27 . H272 . 0.971 no
C27 . H271 . 0.977 no
C28 . C29 . 1.528(5) yes
C28 . H282 . 0.969 no
C28 . H281 . 0.972 no
C29 . C30 . 1.519(5) yes
C29 . H291 . 0.971 no
C29 . H292 . 0.974 no
C30 . C31 . 1.533(5) yes
C30 . H301 . 0.965 no
C30 . H302 . 0.976 no
C31 . C32 . 1.518(5) yes
C31 . H311 . 0.969 no
C31 . H312 . 0.972 no
C32 . C33 . 1.533(5) yes
C32 . H322 . 0.969 no
C32 . H321 . 0.970 no
C33 . C34 . 1.518(6) yes
C33 . H332 . 0.973 no
C33 . H331 . 0.980 no
C34 . C35 . 1.527(6) yes
C34 . H341 . 0.981 no
C34 . H342 . 0.977 no
C35 . C36 . 1.521(7) yes
C35 . H351 . 0.979 no
C35 . H352 . 0.980 no
C36 . H361 . 0.966 no
C36 . H362 . 0.971 no
C36 . H363 . 0.966 no
C37 . C38 . 1.527(6) yes
C37 . H371 . 0.978 no
C37 . H372 . 0.978 no
C38 . C39 . 1.514(5) yes
C38 . H381 . 0.976 no
C38 . H382 . 0.977 no
C39 . C40 . 1.526(6) yes
C39 . H392 . 0.974 no
C39 . H391 . 0.980 no
C40 . C41 . 1.502(6) yes
C40 . H402 . 0.974 no
C40 . H401 . 0.985 no
C41 . C42 . 1.544(6) yes
C41 . H411 . 0.973 no
C41 . H412 . 0.979 no
C42 . C43 . 1.502(7) yes
C42 . H421 . 0.975 no
C42 . H422 . 0.974 no
C42 . C143 . 1.543(7) yes
C42 . H421 . 0.975 no
C42 . H422 . 0.974 no
C43 . C44 . 1.557(7) yes
C43 . H432 . 0.971 no
C43 . H431 . 0.974 no
C44 . C45 . 1.547(7) yes
C44 . H441 . 0.964 no
C44 . H442 . 0.963 no
C45 . C46 . 1.517(8) yes
C45 . H451 . 0.974 no
C45 . H452 . 0.971 no
C46 . C47 . 1.574(8) yes
C46 . H461 . 0.973 no
C46 . H462 . 0.973 no
C47 . C48 . 1.503(8) yes
C47 . H472 . 0.967 no
C47 . H471 . 0.971 no
C48 . H482 . 0.963 no
C48 . H481 . 0.967 no
C48 . H483 . 0.965 no
C143 . C144 . 1.560(7) yes
C143 . H1432 . 0.975 no
C143 . H1431 . 0.973 no
C144 . C145 . 1.530(8) yes
C144 . H1442 . 0.977 no
C144 . H1441 . 0.977 no
C145 . C146 . 1.563(8) yes
C145 . H1451 . 0.975 no
C145 . H1452 . 0.970 no
C146 . C147 . 1.536(8) yes
C146 . H1461 . 0.973 no
C146 . H1462 . 0.974 no
C147 . C148 . 1.530(8) yes
C147 . H1471 . 0.974 no
C147 . H1472 . 0.978 no
C148 . H1483 . 0.970 no
C148 . H1481 . 0.967 no
C148 . H1482 . 0.968 no
C49 . C50 . 1.399(8) yes
C49 . C54 . 1.350(8) yes
C49 . H491 . 0.939 no
C50 . C51 . 1.408(8) yes
C50 . H501 . 0.933 no
C51 . C52 . 1.383(8) yes
C51 . H511 . 0.934 no
C52 . C53 . 1.329(8) yes
C52 . H521 . 0.940 no
C53 . C54 . 1.366(8) yes
C53 . H531 . 0.947 no
C54 . H541 . 0.939 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 . N1 . C10 . 108.2(3) yes
C4 . N1 . C25 . 125.4(3) yes
C10 . N1 . C25 . 125.9(3) yes
N3 . N2 . C7 . 112.2(3) yes
N2 . N3 . C13 . 113.9(3) yes
C16 . N4 . C22 . 108.6(3) yes
C16 . N4 . C37 . 125.6(3) yes
C22 . N4 . C37 . 125.8(3) yes
N6 . N5 . C19 . 114.8(3) yes
C1 2_656 N6 . N5 . 113.0(3) yes
N6 2_656 C1 . C2 . 115.6(3) yes
N6 2_656 C1 . C6 . 123.9(3) yes
C2 . C1 . C6 . 120.5(3) yes
C1 . C2 . C3 . 122.3(3) yes
C1 . C2 . H21 . 118.8 no
C3 . C2 . H21 . 118.9 no
C2 . C3 . C4 . 117.9(3) yes
C2 . C3 . H31 . 121.1 no
C4 . C3 . H31 . 121.0 no
C3 . C4 . N1 . 129.4(3) yes
C3 . C4 . C5 . 120.7(3) yes
N1 . C4 . C5 . 109.9(3) yes
C4 . C5 . C6 . 120.0(3) yes
C4 . C5 . C11 . 105.8(3) yes
C6 . C5 . C11 . 134.1(3) yes
C1 . C6 . C5 . 118.5(3) yes
C1 . C6 . H61 . 120.7 no
C5 . C6 . H61 . 120.8 no
N2 . C7 . C8 . 123.6(3) yes
N2 . C7 . C12 . 115.2(3) yes
C8 . C7 . C12 . 121.2(3) yes
C7 . C8 . C9 . 121.5(3) yes
C7 . C8 . H81 . 119.8 no
C9 . C8 . H81 . 118.7 no
C8 . C9 . C10 . 116.9(3) yes
C8 . C9 . H91 . 121.6 no
C10 . C9 . H91 . 121.5 no
C9 . C10 . N1 . 128.7(3) yes
C9 . C10 . C11 . 122.4(3) yes
N1 . C10 . C11 . 108.9(3) yes
C5 . C11 . C10 . 107.3(3) yes
C5 . C11 . C12 . 134.1(3) yes
C10 . C11 . C12 . 118.7(3) yes
C11 . C12 . C7 . 119.3(3) yes
C11 . C12 . H121 . 120.2 no
C7 . C12 . H121 . 120.4 no
N3 . C13 . C14 . 113.6(3) yes
N3 . C13 . C18 . 125.3(3) yes
C14 . C13 . C18 . 121.1(3) yes
C13 . C14 . C15 . 122.0(4) yes
C13 . C14 . H141 . 118.9 no
C15 . C14 . H141 . 119.1 no
C14 . C15 . C16 . 117.3(3) yes
C14 . C15 . H151 . 121.7 no
C16 . C15 . H151 . 121.1 no
C15 . C16 . N4 . 129.1(3) yes
C15 . C16 . C17 . 122.0(3) yes
N4 . C16 . C17 . 108.9(3) yes
C16 . C17 . C18 . 119.0(3) yes
C16 . C17 . C23 . 106.9(3) yes
C18 . C17 . C23 . 134.1(3) yes
C17 . C18 . C13 . 118.6(3) yes
C17 . C18 . H181 . 120.2 no
C13 . C18 . H181 . 121.2 no
N5 . C19 . C20 . 124.2(3) yes
N5 . C19 . C24 . 114.9(3) yes
C20 . C19 . C24 . 120.9(3) yes
C19 . C20 . C21 . 120.9(3) yes
C19 . C20 . H201 . 119.3 no
C21 . C20 . H201 . 119.8 no
C20 . C21 . C22 . 118.6(3) yes
C20 . C21 . H211 . 121.5 no
C22 . C21 . H211 . 119.9 no
C21 . C22 . N4 . 130.0(3) yes
C21 . C22 . C23 . 120.4(3) yes
N4 . C22 . C23 . 109.6(3) yes
C17 . C23 . C22 . 105.9(3) yes
C17 . C23 . C24 . 134.3(3) yes
C22 . C23 . C24 . 119.7(3) yes
C23 . C24 . C19 . 119.4(3) yes
C23 . C24 . H241 . 121.0 no
C19 . C24 . H241 . 119.6 no
N1 . C25 . C26 . 112.8(3) yes
N1 . C25 . H251 . 107.9 no
C26 . C25 . H251 . 110.4 no
N1 . C25 . H252 . 109.3 no
C26 . C25 . H252 . 106.8 no
H251 . C25 . H252 . 109.6 no
C25 . C26 . C27 . 114.0(3) yes
C25 . C26 . H261 . 108.4 no
C27 . C26 . H261 . 107.2 no
C25 . C26 . H262 . 108.4 no
C27 . C26 . H262 . 108.9 no
H261 . C26 . H262 . 109.9 no
C26 . C27 . C28 . 114.9(3) yes
C26 . C27 . H272 . 107.9 no
C28 . C27 . H272 . 109.3 no
C26 . C27 . H271 . 108.1 no
C28 . C27 . H271 . 107.8 no
H272 . C27 . H271 . 108.8 no
C27 . C28 . C29 . 112.5(3) yes
C27 . C28 . H282 . 109.0 no
C29 . C28 . H282 . 109.1 no
C27 . C28 . H281 . 108.5 no
C29 . C28 . H281 . 108.5 no
H282 . C28 . H281 . 109.1 no
C28 . C29 . C30 . 114.2(3) yes
C28 . C29 . H291 . 108.6 no
C30 . C29 . H291 . 108.1 no
C28 . C29 . H292 . 107.6 no
C30 . C29 . H292 . 108.9 no
H291 . C29 . H292 . 109.4 no
C29 . C30 . C31 . 113.3(3) yes
C29 . C30 . H301 . 109.1 no
C31 . C30 . H301 . 108.1 no
C29 . C30 . H302 . 108.6 no
C31 . C30 . H302 . 108.0 no
H301 . C30 . H302 . 109.6 no
C30 . C31 . C32 . 113.2(3) yes
C30 . C31 . H311 . 107.8 no
C32 . C31 . H311 . 108.2 no
C30 . C31 . H312 . 108.4 no
C32 . C31 . H312 . 109.5 no
H311 . C31 . H312 . 109.7 no
C31 . C32 . C33 . 114.9(3) yes
C31 . C32 . H322 . 108.1 no
C33 . C32 . H322 . 108.1 no
C31 . C32 . H321 . 108.1 no
C33 . C32 . H321 . 109.1 no
H322 . C32 . H321 . 108.4 no
C32 . C33 . C34 . 114.2(3) yes
C32 . C33 . H332 . 108.0 no
C34 . C33 . H332 . 108.4 no
C32 . C33 . H331 . 108.6 no
C34 . C33 . H331 . 108.4 no
H332 . C33 . H331 . 109.3 no
C33 . C34 . C35 . 112.1(4) yes
C33 . C34 . H341 . 108.5 no
C35 . C34 . H341 . 109.2 no
C33 . C34 . H342 . 109.4 no
C35 . C34 . H342 . 108.2 no
H341 . C34 . H342 . 109.4 no
C34 . C35 . C36 . 113.8(4) yes
C34 . C35 . H351 . 108.7 no
C36 . C35 . H351 . 109.1 no
C34 . C35 . H352 . 108.2 no
C36 . C35 . H352 . 107.7 no
H351 . C35 . H352 . 109.2 no
C35 . C36 . H361 . 110.0 no
C35 . C36 . H362 . 108.4 no
H361 . C36 . H362 . 110.1 no
C35 . C36 . H363 . 108.9 no
H361 . C36 . H363 . 110.3 no
H362 . C36 . H363 . 109.1 no
N4 . C37 . C38 . 113.1(3) yes
N4 . C37 . H371 . 107.8 no
C38 . C37 . H371 . 109.6 no
N4 . C37 . H372 . 108.6 no
C38 . C37 . H372 . 108.1 no
H371 . C37 . H372 . 109.6 no
C37 . C38 . C39 . 115.0(3) yes
C37 . C38 . H381 . 109.1 no
C39 . C38 . H381 . 108.3 no
C37 . C38 . H382 . 107.4 no
C39 . C38 . H382 . 106.9 no
H381 . C38 . H382 . 110.1 no
C38 . C39 . C40 . 112.5(3) yes
C38 . C39 . H392 . 109.0 no
C40 . C39 . H392 . 108.5 no
C38 . C39 . H391 . 108.7 no
C40 . C39 . H391 . 108.5 no
H392 . C39 . H391 . 109.7 no
C39 . C40 . C41 . 113.8(3) yes
C39 . C40 . H402 . 107.6 no
C41 . C40 . H402 . 106.2 no
C39 . C40 . H401 . 109.0 no
C41 . C40 . H401 . 109.8 no
H402 . C40 . H401 . 110.4 no
C40 . C41 . C42 . 115.5(4) yes
C40 . C41 . H411 . 107.3 no
C42 . C41 . H411 . 105.9 no
C40 . C41 . H412 . 107.9 no
C42 . C41 . H412 . 109.4 no
H411 . C41 . H412 . 110.8 no
C41 . C42 . C43 . 112.4(4) yes
C41 . C42 . H421 . 109.8 no
C43 . C42 . H421 . 98.0 no
C41 . C42 . H422 . 109.4 no
C43 . C42 . H422 . 117.4 no
H421 . C42 . H422 . 109.2 no
C41 . C42 . C143 . 111.4(4) yes
C41 . C42 . H421 . 109.8 no
C143 . C42 . H421 . 118.1 no
C41 . C42 . H422 . 109.4 no
C143 . C42 . H422 . 98.2 no
H421 . C42 . H422 . 109.2 no
C42 . C43 . C44 . 112.1(4) yes
C42 . C43 . H432 . 108.2 no
C44 . C43 . H432 . 109.4 no
C42 . C43 . H431 . 108.0 no
C44 . C43 . H431 . 109.2 no
H432 . C43 . H431 . 109.9 no
C43 . C44 . C45 . 105.7(4) yes
C43 . C44 . H441 . 109.6 no
C45 . C44 . H441 . 112.6 no
C43 . C44 . H442 . 112.3 no
C45 . C44 . H442 . 108.6 no
H441 . C44 . H442 . 108.1 no
C44 . C45 . C46 . 114.1(4) yes
C44 . C45 . H451 . 108.0 no
C46 . C45 . H451 . 105.7 no
C44 . C45 . H452 . 109.0 no
C46 . C45 . H452 . 110.0 no
H451 . C45 . H452 . 110.0 no
C45 . C46 . C47 . 106.6(4) yes
C45 . C46 . H461 . 112.8 no
C47 . C46 . H461 . 113.4 no
C45 . C46 . H462 . 105.6 no
C47 . C46 . H462 . 109.1 no
H461 . C46 . H462 . 108.9 no
C46 . C47 . C48 . 110.5(4) yes
C46 . C47 . H472 . 108.9 no
C48 . C47 . H472 . 109.6 no
C46 . C47 . H471 . 111.0 no
C48 . C47 . H471 . 107.5 no
H472 . C47 . H471 . 109.3 no
C47 . C48 . H482 . 108.8 no
C47 . C48 . H481 . 107.9 no
H482 . C48 . H481 . 110.4 no
C47 . C48 . H483 . 109.0 no
H482 . C48 . H483 . 110.0 no
H481 . C48 . H483 . 110.8 no
C42 . C143 . C144 . 110.9(4) yes
C42 . C143 . H1432 . 109.1 no
C144 . C143 . H1432 . 108.3 no
C42 . C143 . H1431 . 109.5 no
C144 . C143 . H1431 . 109.4 no
H1432 . C143 . H1431 . 109.6 no
C143 . C144 . C145 . 110.5(4) yes
C143 . C144 . H1442 . 108.4 no
C145 . C144 . H1442 . 108.8 no
C143 . C144 . H1441 . 110.5 no
C145 . C144 . H1441 . 108.5 no
H1442 . C144 . H1441 . 110.2 no
C144 . C145 . C146 . 110.6(4) yes
C144 . C145 . H1451 . 109.0 no
C146 . C145 . H1451 . 109.3 no
C144 . C145 . H1452 . 108.5 no
C146 . C145 . H1452 . 109.4 no
H1451 . C145 . H1452 . 110.1 no
C145 . C146 . C147 . 111.4(4) yes
C145 . C146 . H1461 . 109.3 no
C147 . C146 . H1461 . 109.0 no
C145 . C146 . H1462 . 109.0 no
C147 . C146 . H1462 . 108.8 no
H1461 . C146 . H1462 . 109.3 no
C146 . C147 . C148 . 110.4(4) yes
C146 . C147 . H1471 . 108.1 no
C148 . C147 . H1471 . 106.6 no
C146 . C147 . H1472 . 110.0 no
C148 . C147 . H1472 . 111.1 no
H1471 . C147 . H1472 . 110.5 no
C147 . C148 . H1483 . 107.8 no
C147 . C148 . H1481 . 110.4 no
H1483 . C148 . H1481 . 110.0 no
C147 . C148 . H1482 . 108.5 no
H1483 . C148 . H1482 . 109.6 no
H1481 . C148 . H1482 . 110.6 no
C50 . C49 . C54 . 119.8(6) yes
C50 . C49 . H491 . 119.9 no
C54 . C49 . H491 . 120.2 no
C49 . C50 . C51 . 117.9(6) yes
C49 . C50 . H501 . 121.1 no
C51 . C50 . H501 . 121.0 no
C50 . C51 . C52 . 119.4(6) yes
C50 . C51 . H511 . 119.9 no
C52 . C51 . H511 . 120.7 no
C51 . C52 . C53 . 121.1(6) yes
C51 . C52 . H521 . 119.0 no
C53 . C52 . H521 . 119.9 no
C52 . C53 . C54 . 120.2(7) yes
C52 . C53 . H531 . 119.6 no
C54 . C53 . H531 . 120.2 no
C53 . C54 . C49 . 121.5(6) yes
C53 . C54 . H541 . 118.8 no
C49 . C54 . H541 . 119.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C146 . H461 . C47 . 142 0.98 2.15 2.991(7) yes
C146 . H461 . C148 . 153 0.98 1.60 2.518(7) yes
C47 . H471 . C47 2_565 134 0.97 2.41 3.166(7) yes
C47 . H471 . C48 2_565 161 0.97 2.27 3.200(7) yes
_database_code_depnum_ccdc_archive 'CCDC 966041'
