# Electronic Supplementary Material (ESI) for ChemComm.
# 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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# 
#  For further information on the CCDC, data deposition and
#  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 
#  to carry out CIF format checking respectively.
#
data_1


_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
#Added by publCIF




_diffrn_radiation_source         'fine-focus sealed tube'
#Added by publCIF




_diffrn_detector_area_resol_mean 8.3333
#Added by publCIF




_exptl_absorpt_correction_T_max  0.7441
#Added by publCIF




_exptl_absorpt_correction_T_min  0.6621
#Added by publCIF



_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                   7.8222(3)
_cell_length_b                   16.1122(6)
_cell_length_c                   27.2257(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.413(3)
_cell_angle_gamma                90
_cell_volume                     3430.3(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-p 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 '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            4

# Given Formula = C33 H39 N3 O3 
# Dc =      1.02 Fooo =   1128.00 Mu =      0.65 M =    525.69
# Found Formula = C33 H39 N3 O3 
# Dc =      1.02 FOOO =   1128.00 Mu =      0.65 M =    525.69

_chemical_formula_sum            'C33 H39 N3 O3'
_chemical_formula_moiety         'C33 H39 N3 O3'
_chemical_compound_source        ?
_chemical_formula_weight         525.69


_cell_measurement_reflns_used    704
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      15.35
_cell_measurement_temperature    296

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.35
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_max          1.61

_exptl_crystal_density_diffrn    1.018
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.065

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   multi-scan
_diffrn_measurement_device_type  'Bruker APEXII CCD diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'APEX II (Bruker 2008)'
_computing_cell_refinement       'SAINT (Bruker 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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         .
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      296
_diffrn_reflns_number            9408
_reflns_number_total             9408
_diffrn_reflns_av_R_equivalents  0.072
# Number of reflections without Friedels Law is 9408 
# Number of reflections with Friedels Law is 4809 
# Theoretical number of reflections is about 4810 


_diffrn_reflns_theta_min         1.469
_diffrn_reflns_theta_max         23.092
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        23.092
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              -17
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              30

_oxford_diffrn_Wilson_B_factor   3.73
_oxford_diffrn_Wilson_scale      73.88

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

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.22


# 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>0.0\s(I)
_refine_ls_number_reflns         5126
_refine_ls_number_restraints     0
_refine_ls_number_parameters     353
_oxford_refine_ls_R_factor_ref   0.0566
_refine_ls_wR_factor_ref         0.0596
_refine_ls_goodness_of_fit_ref   1.0713
_refine_ls_shift/su_max          0.0001785
_refine_ls_shift/su_mean         0.0000168


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        9368
_refine_ls_R_factor_all          0.1027
_refine_ls_wR_factor_all         0.1180

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6192
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_gt          0.0654

# 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    constr #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: 
 0.682 0.953 0.594 0.259 0.100 
;

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

# Replace last . with number of unfound hydrogen atoms attached 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
C1 C 0.3191(3) 0.22704(13) 0.42825(9) 0.0541 1.0000 Uani . . . . . .
C2 C 0.3753(2) 0.27364(13) 0.38368(9) 0.0487 1.0000 Uani . . . . . .
C3 C 0.4576(3) 0.34873(14) 0.38971(10) 0.0643 1.0000 Uani . . . . . .
C4 C 0.5194(4) 0.38934(16) 0.34949(12) 0.0765 1.0000 Uani . . . . . .
C5 C 0.5013(3) 0.35562(13) 0.30357(11) 0.0632 1.0000 Uani . . . . . .
C6 C 0.4212(3) 0.27953(12) 0.29648(9) 0.0508 1.0000 Uani . . . . . .
C7 C 0.3584(3) 0.23953(13) 0.33708(9) 0.0531 1.0000 Uani . . . . . .
C8 C 0.4022(4) 0.24751(15) 0.24513(10) 0.0798 1.0000 Uani . . . . . .
C9 C 0.4997(3) 0.10119(17) 0.22634(10) 0.0671 1.0000 Uani . . . . . .
C10 C 0.6423(4) 0.0998(3) 0.26523(14) 0.1238 1.0000 Uani . . . . . .
C11 C 0.5673(4) 0.1213(2) 0.17572(12) 0.1058 1.0000 Uani . . . . . .
C12 C 0.1964(3) 0.13730(13) 0.23998(9) 0.0519 1.0000 Uani . . . . . .
C13 C 0.1444(3) 0.04935(13) 0.23133(9) 0.0480 1.0000 Uani . . . . . .
C14 C 0.0565(3) 0.02837(16) 0.18837(10) 0.0675 1.0000 Uani . . . . . .
C15 C -0.0032(4) -0.05237(19) 0.18236(12) 0.0812 1.0000 Uani . . . . . .
C16 C 0.0221(3) -0.10994(16) 0.21874(11) 0.0700 1.0000 Uani . . . . . .
C17 C 0.1080(3) -0.09007(13) 0.26184(9) 0.0525 1.0000 Uani . . . . . .
C18 C 0.1693(3) -0.00914(12) 0.26784(9) 0.0481 1.0000 Uani . . . . . .
C19 C 0.1334(3) -0.15534(13) 0.30098(10) 0.0641 1.0000 Uani . . . . . .
C20 C -0.0433(3) -0.12641(15) 0.37464(10) 0.0636 1.0000 Uani . . . . . .
C21 C -0.1756(3) -0.07540(19) 0.34600(12) 0.0835 1.0000 Uani . . . . . .
C22 C -0.1022(4) -0.2151(2) 0.38259(13) 0.1042 1.0000 Uani . . . . . .
C23 C 0.2702(3) -0.10582(15) 0.37553(12) 0.0662 1.0000 Uani . . . . . .
C24 C 0.2606(3) -0.06294(14) 0.42401(11) 0.0605 1.0000 Uani . . . . . .
C25 C 0.3277(3) -0.09841(19) 0.46641(15) 0.0765 1.0000 Uani . . . . . .
C26 C 0.3247(3) -0.0562(2) 0.50980(14) 0.0789 1.0000 Uani . . . . . .
C27 C 0.2583(3) 0.02306(19) 0.51178(10) 0.0691 1.0000 Uani . . . . . .
C28 C 0.1926(3) 0.06138(15) 0.46964(10) 0.0565 1.0000 Uani . . . . . .
C29 C 0.1943(3) 0.01718(15) 0.42617(10) 0.0596 1.0000 Uani . . . . . .
C30 C 0.1153(3) 0.14661(15) 0.47206(9) 0.0655 1.0000 Uani . . . . . .
C31 C 0.0144(3) 0.24142(15) 0.40336(10) 0.0611 1.0000 Uani . . . . . .
C32 C -0.0993(3) 0.18097(19) 0.37514(11) 0.0879 1.0000 Uani . . . . . .
C33 C -0.0881(4) 0.2955(2) 0.43760(13) 0.1050 1.0000 Uani . . . . . .
O34 O 0.4233(2) 0.21148(12) 0.46109(7) 0.0837 1.0000 Uani . . . . . .
O35 O 0.0842(2) 0.18932(10) 0.24674(8) 0.0836 1.0000 Uani . . . . . .
O36 O 0.4097(2) -0.11990(15) 0.35723(10) 0.1177 1.0000 Uani . . . . . .
N37 N 0.3620(3) 0.15848(10) 0.23993(7) 0.0563 1.0000 Uani . . . . . .
N38 N 0.1238(2) -0.12388(10) 0.35095(8) 0.0544 1.0000 Uani . . . . . .
N39 N 0.1555(2) 0.19979(11) 0.42974(7) 0.0530 1.0000 Uani . . . . . .
H31 H 0.4705 0.3756 0.4216 0.0802 1.0000 Uiso R . . . . .
H41 H 0.5792 0.4422 0.3550 0.0909 1.0000 Uiso R . . . . .
H51 H 0.5457 0.3826 0.2751 0.0784 1.0000 Uiso R . . . . .
H71 H 0.3011 0.1864 0.3335 0.0646 1.0000 Uiso R . . . . .
H81 H 0.5068 0.2586 0.2271 0.1048 1.0000 Uiso R . . . . .
H82 H 0.3102 0.2779 0.2276 0.1060 1.0000 Uiso R . . . . .
H91 H 0.4491 0.0450 0.2251 0.0873 1.0000 Uiso R . . . . .
H101 H 0.5932 0.0920 0.2968 0.1942 1.0000 Uiso R . . . . .
H102 H 0.7025 0.1514 0.2631 0.1943 1.0000 Uiso R . . . . .
H103 H 0.7158 0.0543 0.2575 0.1936 1.0000 Uiso R . . . . .
H111 H 0.4741 0.1278 0.1527 0.1709 1.0000 Uiso R . . . . .
H112 H 0.6322 0.1725 0.1759 0.1711 1.0000 Uiso R . . . . .
H113 H 0.6400 0.0773 0.1648 0.1710 1.0000 Uiso R . . . . .
H141 H 0.0396 0.0716 0.1620 0.0854 1.0000 Uiso R . . . . .
H151 H -0.0657 -0.0658 0.1525 0.0996 1.0000 Uiso R . . . . .
H161 H -0.0202 -0.1660 0.2148 0.0872 1.0000 Uiso R . . . . .
H181 H 0.2354 0.0063 0.2975 0.0621 1.0000 Uiso R . . . . .
H191 H 0.2480 -0.1804 0.2983 0.0814 1.0000 Uiso R . . . . .
H192 H 0.0420 -0.1992 0.2962 0.0806 1.0000 Uiso R . . . . .
H201 H -0.0296 -0.0981 0.4087 0.0834 1.0000 Uiso R . . . . .
H211 H -0.1375 -0.0184 0.3444 0.1335 1.0000 Uiso R . . . . .
H212 H -0.2804 -0.0767 0.3631 0.1337 1.0000 Uiso R . . . . .
H213 H -0.1875 -0.0986 0.3126 0.1334 1.0000 Uiso R . . . . .
H221 H -0.0128 -0.2436 0.4011 0.1601 1.0000 Uiso R . . . . .
H222 H -0.2032 -0.2132 0.4022 0.1596 1.0000 Uiso R . . . . .
H223 H -0.1279 -0.2415 0.3508 0.1601 1.0000 Uiso R . . . . .
H251 H 0.3791 -0.1535 0.4651 0.0958 1.0000 Uiso R . . . . .
H261 H 0.3710 -0.0838 0.5397 0.0960 1.0000 Uiso R . . . . .
H271 H 0.2572 0.0529 0.5423 0.0902 1.0000 Uiso R . . . . .
H291 H 0.1461 0.0418 0.3966 0.0743 1.0000 Uiso R . . . . .
H301 H 0.1559 0.1741 0.5041 0.0849 1.0000 Uiso R . . . . .
H302 H -0.0119 0.1421 0.4733 0.0847 1.0000 Uiso R . . . . .
H311 H 0.0668 0.2786 0.3778 0.0788 1.0000 Uiso R . . . . .
H321 H -0.0355 0.1535 0.3493 0.1398 1.0000 Uiso R . . . . .
H322 H -0.1436 0.1410 0.3978 0.1404 1.0000 Uiso R . . . . .
H323 H -0.1950 0.2113 0.3607 0.1402 1.0000 Uiso R . . . . .
H331 H -0.0043 0.3286 0.4552 0.1623 1.0000 Uiso R . . . . .
H332 H -0.1498 0.2596 0.4591 0.1636 1.0000 Uiso R . . . . .
H333 H -0.1590 0.3328 0.4184 0.1632 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       400(100)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.1412(3)
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
C1 . C2 . 1.502(3) yes
C1 . O34 . 1.221(3) yes
C1 . N39 . 1.354(3) yes
C2 . C3 . 1.378(3) yes
C2 . C7 . 1.386(3) yes
C3 . C4 . 1.374(4) yes
C3 . H31 . 0.973 no
C4 . C5 . 1.367(4) yes
C4 . H41 . 0.981 no
C5 . C6 . 1.388(3) yes
C5 . H51 . 0.960 no
C6 . C7 . 1.380(3) yes
C6 . C8 . 1.494(3) yes
C7 . H71 . 0.971 no
C8 . N37 . 1.475(3) yes
C8 . H81 . 0.980 no
C8 . H82 . 0.984 no
C9 . C10 . 1.519(4) yes
C9 . C11 . 1.523(4) yes
C9 . N37 . 1.472(3) yes
C9 . H91 . 0.988 no
C10 . H101 . 0.957 no
C10 . H102 . 0.957 no
C10 . H103 . 0.958 no
C11 . H111 . 0.955 no
C11 . H112 . 0.968 no
C11 . H113 . 0.960 no
C12 . C13 . 1.491(3) yes
C12 . O35 . 1.231(3) yes
C12 . N37 . 1.339(3) yes
C13 . C14 . 1.384(3) yes
C13 . C18 . 1.380(3) yes
C14 . C15 . 1.390(4) yes
C14 . H141 . 1.007 no
C15 . C16 . 1.368(4) yes
C15 . H151 . 0.963 no
C16 . C17 . 1.376(3) yes
C16 . H161 . 0.967 no
C17 . C18 . 1.397(3) yes
C17 . C19 . 1.507(3) yes
C18 . H181 . 0.980 no
C19 . N38 . 1.455(3) yes
C19 . H191 . 0.988 no
C19 . H192 . 1.012 no
C20 . C21 . 1.521(4) yes
C20 . C22 . 1.518(4) yes
C20 . N38 . 1.473(3) yes
C20 . H201 . 1.038 no
C21 . H211 . 0.967 no
C21 . H212 . 0.953 no
C21 . H213 . 0.985 no
C22 . H221 . 0.967 no
C22 . H222 . 0.965 no
C22 . H223 . 0.980 no
C23 . C24 . 1.493(4) yes
C23 . O36 . 1.232(3) yes
C23 . N38 . 1.344(3) yes
C24 . C25 . 1.380(4) yes
C24 . C29 . 1.393(3) yes
C25 . C26 . 1.364(4) yes
C25 . H251 . 0.976 no
C26 . C27 . 1.380(4) yes
C26 . H261 . 0.988 no
C27 . C28 . 1.390(3) yes
C27 . H271 . 0.962 no
C28 . C29 . 1.382(3) yes
C28 . C30 . 1.503(3) yes
C29 . H291 . 0.967 no
C30 . N39 . 1.476(3) yes
C30 . H301 . 1.021 no
C30 . H302 . 0.999 no
C31 . C32 . 1.516(3) yes
C31 . C33 . 1.519(4) yes
C31 . N39 . 1.464(3) yes
C31 . H311 . 1.012 no
C32 . H321 . 0.978 no
C32 . H322 . 0.962 no
C32 . H323 . 0.969 no
C33 . H331 . 0.962 no
C33 . H332 . 0.962 no
C33 . H333 . 0.963 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
C2 . C1 . O34 . 119.4(2) yes
C2 . C1 . N39 . 118.8(2) yes
O34 . C1 . N39 . 121.7(2) yes
C1 . C2 . C3 . 119.2(2) yes
C1 . C2 . C7 . 121.20(19) yes
C3 . C2 . C7 . 119.4(2) yes
C2 . C3 . C4 . 119.7(3) yes
C2 . C3 . H31 . 122.3 no
C4 . C3 . H31 . 117.9 no
C3 . C4 . C5 . 120.6(2) yes
C3 . C4 . H41 . 117.9 no
C5 . C4 . H41 . 121.5 no
C4 . C5 . C6 . 121.0(2) yes
C4 . C5 . H51 . 121.7 no
C6 . C5 . H51 . 117.3 no
C5 . C6 . C7 . 118.0(2) yes
C5 . C6 . C8 . 118.0(2) yes
C7 . C6 . C8 . 123.97(19) yes
C2 . C7 . C6 . 121.3(2) yes
C2 . C7 . H71 . 118.4 no
C6 . C7 . H71 . 120.3 no
C6 . C8 . N37 . 116.2(2) yes
C6 . C8 . H81 . 109.8 no
N37 . C8 . H81 . 107.9 no
C6 . C8 . H82 . 109.7 no
N37 . C8 . H82 . 106.6 no
H81 . C8 . H82 . 106.0 no
C10 . C9 . C11 . 111.6(3) yes
C10 . C9 . N37 . 111.3(2) yes
C11 . C9 . N37 . 111.5(2) yes
C10 . C9 . H91 . 107.3 no
C11 . C9 . H91 . 108.1 no
N37 . C9 . H91 . 106.8 no
C9 . C10 . H101 . 108.8 no
C9 . C10 . H102 . 107.4 no
H101 . C10 . H102 . 112.1 no
C9 . C10 . H103 . 107.0 no
H101 . C10 . H103 . 110.6 no
H102 . C10 . H103 . 110.6 no
C9 . C11 . H111 . 109.9 no
C9 . C11 . H112 . 111.7 no
H111 . C11 . H112 . 107.6 no
C9 . C11 . H113 . 110.1 no
H111 . C11 . H113 . 109.0 no
H112 . C11 . H113 . 108.4 no
C13 . C12 . O35 . 118.5(2) yes
C13 . C12 . N37 . 120.13(19) yes
O35 . C12 . N37 . 121.3(2) yes
C12 . C13 . C14 . 119.6(2) yes
C12 . C13 . C18 . 120.1(2) yes
C14 . C13 . C18 . 120.0(2) yes
C13 . C14 . C15 . 119.1(3) yes
C13 . C14 . H141 . 119.2 no
C15 . C14 . H141 . 121.7 no
C14 . C15 . C16 . 120.5(3) yes
C14 . C15 . H151 . 118.2 no
C16 . C15 . H151 . 121.4 no
C15 . C16 . C17 . 121.3(2) yes
C15 . C16 . H161 . 120.7 no
C17 . C16 . H161 . 118.1 no
C16 . C17 . C18 . 118.4(2) yes
C16 . C17 . C19 . 119.6(2) yes
C18 . C17 . C19 . 122.0(2) yes
C17 . C18 . C13 . 120.7(2) yes
C17 . C18 . H181 . 120.3 no
C13 . C18 . H181 . 118.9 no
C17 . C19 . N38 . 114.15(18) yes
C17 . C19 . H191 . 109.7 no
N38 . C19 . H191 . 106.2 no
C17 . C19 . H192 . 108.4 no
N38 . C19 . H192 . 108.1 no
H191 . C19 . H192 . 110.2 no
C21 . C20 . C22 . 112.1(2) yes
C21 . C20 . N38 . 111.1(2) yes
C22 . C20 . N38 . 111.4(2) yes
C21 . C20 . H201 . 106.0 no
C22 . C20 . H201 . 108.1 no
N38 . C20 . H201 . 107.9 no
C20 . C21 . H211 . 109.3 no
C20 . C21 . H212 . 108.7 no
H211 . C21 . H212 . 108.2 no
C20 . C21 . H213 . 108.4 no
H211 . C21 . H213 . 110.0 no
H212 . C21 . H213 . 112.3 no
C20 . C22 . H221 . 107.7 no
C20 . C22 . H222 . 107.8 no
H221 . C22 . H222 . 108.6 no
C20 . C22 . H223 . 109.8 no
H221 . C22 . H223 . 112.5 no
H222 . C22 . H223 . 110.4 no
C24 . C23 . O36 . 120.5(2) yes
C24 . C23 . N38 . 118.6(2) yes
O36 . C23 . N38 . 120.7(3) yes
C23 . C24 . C25 . 121.4(3) yes
C23 . C24 . C29 . 119.5(2) yes
C25 . C24 . C29 . 118.9(3) yes
C24 . C25 . C26 . 120.2(3) yes
C24 . C25 . H251 . 119.6 no
C26 . C25 . H251 . 120.1 no
C25 . C26 . C27 . 120.6(3) yes
C25 . C26 . H261 . 118.3 no
C27 . C26 . H261 . 121.1 no
C26 . C27 . C28 . 120.7(3) yes
C26 . C27 . H271 . 120.6 no
C28 . C27 . H271 . 118.7 no
C27 . C28 . C29 . 117.8(3) yes
C27 . C28 . C30 . 120.7(3) yes
C29 . C28 . C30 . 121.4(2) yes
C24 . C29 . C28 . 121.7(2) yes
C24 . C29 . H291 . 118.9 no
C28 . C29 . H291 . 119.4 no
C28 . C30 . N39 . 113.7(2) yes
C28 . C30 . H301 . 108.4 no
N39 . C30 . H301 . 110.3 no
C28 . C30 . H302 . 109.7 no
N39 . C30 . H302 . 107.5 no
H301 . C30 . H302 . 107.0 no
C32 . C31 . C33 . 111.6(2) yes
C32 . C31 . N39 . 112.3(2) yes
C33 . C31 . N39 . 111.4(2) yes
C32 . C31 . H311 . 106.0 no
C33 . C31 . H311 . 108.1 no
N39 . C31 . H311 . 107.2 no
C31 . C32 . H321 . 110.6 no
C31 . C32 . H322 . 108.8 no
H321 . C32 . H322 . 110.9 no
C31 . C32 . H323 . 108.6 no
H321 . C32 . H323 . 109.9 no
H322 . C32 . H323 . 108.0 no
C31 . C33 . H331 . 105.0 no
C31 . C33 . H332 . 108.0 no
H331 . C33 . H332 . 112.1 no
C31 . C33 . H333 . 109.3 no
H331 . C33 . H333 . 107.5 no
H332 . C33 . H333 . 114.6 no
C8 . N37 . C9 . 118.6(2) yes
C8 . N37 . C12 . 116.8(2) yes
C9 . N37 . C12 . 123.63(18) yes
C20 . N38 . C19 . 117.81(19) yes
C20 . N38 . C23 . 122.9(2) yes
C19 . N38 . C23 . 118.6(2) yes
C30 . N39 . C31 . 118.41(19) yes
C30 . N39 . C1 . 115.57(19) yes
C31 . N39 . C1 . 122.54(19) yes
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
C19 . H192 . O35 3_545 152.39(8) 1.012 2.347 3.277(4) yes
C20 . H201 . C29 . 122.27(8) 1.038 2.589 3.263(4) yes
C21 . H212 . O36 1_455 144.27(9) 0.953 2.523 3.344(4) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 12/09/13 at 13:20:18
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) H   ( 333,X'S) 
END                                                                             
;



_iucr_refine_instruction_details_restraints 
;
#
# Punched on 12/09/13 at 13:20:18
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-1 -2 3 x .
0 3 2 x .
0 0 6 x .
0 3 4 x .
0 -3 4 x .
0 3 5 x .
0 3 3 x .
0 4 3 x .
0 -4 3 x .
0 3 6 x .
0 -3 6 x .

# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: This x-ray structure will be part of a publication dealing with
 synthesis and conformational analysis of novel macrocycles in solution and in
 solid state. The number of authors is then fully justified since it does not
 concerned only X-ray diffraction studies.
;
_vrf_PLAT601_I                   
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of 312 Ang3  
RESPONSE: The large solvent accessible voids in the lattice is due the
 particular crystal packing of this molecule. A the second level of
 organisation into 6 parallel interdigitated tube-like structures
 formed a nanoscale hollow tube (inner 15 x 6 Ang). No ordered or disordered
 density was detected in this tubular cavity.
;
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 967255'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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 
#  to carry out CIF format checking respectively.
#
data_1
_publcif_datablock.id            {b156f4bb-ec04-4b93-92ac-fc072666091b}

_chemical_name_systematic        ?
#Added by publCIF




_exptl_absorpt_correction_T_max  0.7450
#Added by publCIF




_diffrn_detector_area_resol_mean 8.3333
#Added by publCIF




_diffrn_radiation_source         'fine-focus sealed tube'
#Added by publCIF




_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
#Added by publCIF




_exptl_absorpt_correction_T_min  0.6687
#Added by publCIF



_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                   10.0817(5)
_cell_length_b                   11.6133(5)
_cell_length_c                   12.8736(7)
_cell_angle_alpha                87.427(2)
_cell_angle_beta                 72.884(2)
_cell_angle_gamma                73.850(2)
_cell_volume                     1382.54(12)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1 '
_symmetry_space_group_name_Hall  'p 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z

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'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 '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            1

# Given Formula = C60 H66 N6 O6 
# Dc =      1.16 Fooo =    516.00 Mu =      0.75 M =    967.22
# Found Formula = C60 H66 N6 O6 
# Dc =      1.16 FOOO =    516.00 Mu =      0.75 M =    967.22

_chemical_formula_sum            'C60 H66 N6 O6'
_chemical_formula_moiety         'C60 H66 N6 O6'
_chemical_compound_source        ?
_chemical_formula_weight         967.22


_cell_measurement_reflns_used    3853
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      21.63
_cell_measurement_temperature    296

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_max          0.40

_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.075

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   multi-scan
_diffrn_measurement_device_type  'Bruker APEXII CCD diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'APEX II (Bruker 2008)'
_computing_cell_refinement       'SAINT (Bruker 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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         .
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      296
_diffrn_reflns_number            8034
_reflns_number_total             8034
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections without Friedels Law is 8034 
# Number of reflections with Friedels Law is 4438 
# Theoretical number of reflections is about 4470 


_diffrn_reflns_theta_min         1.656
_diffrn_reflns_theta_max         24.254
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        23.769
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -11
_reflns_limit_k_max              13
_reflns_limit_l_min              -14
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   3.27
_oxford_diffrn_Wilson_scale      12.70

_atom_sites_solution_primary     direct

_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.29


# 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>2.0\s(I)
_refine_ls_number_reflns         6046
_refine_ls_number_restraints     3
_refine_ls_number_parameters     650
_oxford_refine_ls_R_factor_ref   0.0576
_refine_ls_wR_factor_ref         0.0629
_refine_ls_goodness_of_fit_ref   1.1046
_refine_ls_shift/su_max          0.0013378
_refine_ls_shift/su_mean         0.0002477


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        8003
_refine_ls_R_factor_all          0.0756
_refine_ls_wR_factor_all         0.0832

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6046
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_gt          0.0629

# 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 unk


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #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: 
 0.819 1.11 0.773 0.365 0.154 
;

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

# Replace last . with number of unfound hydrogen atoms attached 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
O1 O 1.2317(3) 0.3879(3) -0.0412(2) 0.0523 1.0000 Uani . . . . . .
C1 C 1.2512(4) 0.4370(4) 0.0340(3) 0.0391 1.0000 Uani . . . . . .
N3 N 1.2745(3) 0.3756(3) 0.1206(3) 0.0389 1.0000 Uani . . . . . .
C29 C 1.3139(5) 0.4195(4) 0.2102(4) 0.0500 1.0000 Uani . . . . . .
C30 C 1.4722(6) 0.3621(6) 0.2033(5) 0.0690 1.0000 Uani . . . . . .
C28 C 1.2779(5) 0.2467(4) 0.1221(4) 0.0481 1.0000 Uani . . . . . .
C27 C 1.1317(4) 0.2245(3) 0.1386(3) 0.0379 1.0000 Uani . . . . . .
C22 C 1.0280(4) 0.2409(3) 0.2398(3) 0.0350 1.0000 Uani . . . . . .
C21 C 1.0527(4) 0.2672(4) 0.3449(3) 0.0404 1.0000 Uani . . . . . .
O3 O 1.1186(3) 0.1842(3) 0.3888(2) 0.0507 1.0000 Uani . . . . . .
N2 N 0.9950(4) 0.3785(3) 0.3898(3) 0.0389 1.0000 Uani . . . . . .
C19 C 0.9980(5) 0.4012(4) 0.5008(3) 0.0459 1.0000 Uani . . . . . .
C20 C 1.1359(5) 0.4227(4) 0.5052(4) 0.0528 1.0000 Uani . . . . . .
C18 C 0.9475(4) 0.4808(4) 0.3269(3) 0.0385 1.0000 Uani . . . . . .
C17 C 0.7888(4) 0.5245(3) 0.3387(3) 0.0349 1.0000 Uani . . . . . .
C12 C 0.7422(4) 0.6093(4) 0.2678(3) 0.0361 1.0000 Uani . . . . . .
C11 C 0.8472(4) 0.6542(4) 0.1794(3) 0.0365 1.0000 Uani . . . . . .
O2 O 0.8687(4) 0.7525(3) 0.1897(3) 0.0568 1.0000 Uani . . . . . .
N1 N 0.9208(3) 0.5834(3) 0.0873(3) 0.0346 1.0000 Uani . . . . . .
C8 C 1.0045(4) 0.6350(4) -0.0051(3) 0.0386 1.0000 Uani . . . . . .
C7 C 1.1421(4) 0.6560(4) 0.0051(3) 0.0392 1.0000 Uani . . . . . .
C2 C 1.2556(5) 0.5656(4) 0.0237(3) 0.0435 1.0000 Uani . . . . . .
C3 C 1.3833(5) 0.5929(5) 0.0212(4) 0.0540 1.0000 Uani . . . . . .
C4 C 1.3985(6) 0.7084(5) 0.0003(4) 0.0622 1.0000 Uani . . . . . .
C5 C 1.2869(6) 0.7957(5) -0.0159(4) 0.0582 1.0000 Uani . . . . . .
C6 C 1.1604(5) 0.7703(4) -0.0125(4) 0.0511 1.0000 Uani . . . . . .
C9 C 0.8784(4) 0.4794(4) 0.0642(3) 0.0426 1.0000 Uani . . . . . .
C10 C 0.7592(5) 0.5132(5) 0.0087(4) 0.0584 1.0000 Uani . . . . . .
C13 C 0.5958(4) 0.6550(4) 0.2790(3) 0.0433 1.0000 Uani . . . . . .
C14 C 0.4958(5) 0.6138(4) 0.3558(4) 0.0508 1.0000 Uani . . . . . .
C15 C 0.5406(5) 0.5280(5) 0.4251(4) 0.0526 1.0000 Uani . . . . . .
C16 C 0.6851(5) 0.4840(4) 0.4172(3) 0.0457 1.0000 Uani . . . . . .
C23 C 0.8932(5) 0.2218(4) 0.2491(4) 0.0433 1.0000 Uani . . . . . .
C24 C 0.8693(5) 0.1799(4) 0.1600(4) 0.0496 1.0000 Uani . . . . . .
C25 C 0.9729(5) 0.1570(4) 0.0621(4) 0.0551 1.0000 Uani . . . . . .
C26 C 1.1019(5) 0.1808(4) 0.0509(4) 0.0471 1.0000 Uani . . . . . .
O4 O 0.9126(3) 0.9152(3) 0.8192(3) 0.0548 1.0000 Uani . . . . . .
C31 C 0.9884(4) 0.9580(4) 0.7429(4) 0.0426 1.0000 Uani . . . . . .
N4 N 1.0758(4) 0.8886(3) 0.6542(3) 0.0403 1.0000 Uani . . . . . .
C34 C 1.0795(5) 0.7614(4) 0.6522(4) 0.0457 1.0000 Uani . . . . . .
C35 C 0.9439(4) 0.7389(4) 0.6351(3) 0.0400 1.0000 Uani . . . . . .
C36 C 0.9146(4) 0.7535(3) 0.5356(3) 0.0360 1.0000 Uani . . . . . .
C37 C 1.0206(4) 0.7719(4) 0.4299(3) 0.0372 1.0000 Uani . . . . . .
O5 O 1.1194(3) 0.6860(3) 0.3837(3) 0.0527 1.0000 Uani . . . . . .
N5 N 0.9932(3) 0.8805(3) 0.3868(3) 0.0384 1.0000 Uani . . . . . .
C40 C 0.9010(4) 0.9862(3) 0.4517(3) 0.0351 1.0000 Uani . . . . . .
C41 C 0.7483(4) 1.0316(3) 0.4413(3) 0.0339 1.0000 Uani . . . . . .
C42 C 0.6489(4) 1.1225(4) 0.5140(3) 0.0369 1.0000 Uani . . . . . .
C43 C 0.6874(4) 1.1721(4) 0.6032(3) 0.0376 1.0000 Uani . . . . . .
O6 O 0.7143(4) 1.2691(3) 0.5953(3) 0.0592 1.0000 Uani . . . . . .
N6 N 0.6922(3) 1.1063(3) 0.6932(3) 0.0399 1.0000 Uani . . . . . .
C51 C 0.6328(5) 1.0037(4) 0.7165(3) 0.0438 1.0000 Uani . . . . . .
C52 C 0.4775(6) 1.0366(6) 0.7868(5) 0.0782 1.0000 Uani . . . . . .
C44 C 0.7120(5) 1.1621(4) 0.7847(3) 0.0462 1.0000 Uani . . . . . .
C45 C 0.8622(5) 1.1805(4) 0.7685(3) 0.0429 1.0000 Uani . . . . . .
C46 C 0.9868(5) 1.0869(4) 0.7511(3) 0.0444 1.0000 Uani . . . . . .
C47 C 1.1140(5) 1.1147(5) 0.7502(4) 0.0552 1.0000 Uani . . . . . .
C48 C 1.1173(6) 1.2311(5) 0.7626(4) 0.0613 1.0000 Uani . . . . . .
C49 C 0.9932(6) 1.3234(5) 0.7765(4) 0.0578 1.0000 Uani . . . . . .
C50 C 0.8691(5) 1.2955(5) 0.7788(4) 0.0538 1.0000 Uani . . . . . .
C53 C 0.5100(5) 1.1692(4) 0.5054(4) 0.0486 1.0000 Uani . . . . . .
C54 C 0.4687(5) 1.1243(5) 0.4268(4) 0.0545 1.0000 Uani . . . . . .
C55 C 0.5676(5) 1.0341(5) 0.3543(4) 0.0548 1.0000 Uani . . . . . .
C56 C 0.7049(5) 0.9884(4) 0.3622(3) 0.0424 1.0000 Uani . . . . . .
C38 C 1.0793(5) 0.8946(4) 0.2749(3) 0.0467 1.0000 Uani . . . . . .
C39 C 1.2236(5) 0.9099(4) 0.2652(4) 0.0549 1.0000 Uani . . . . . .
C57 C 0.7869(5) 0.7337(4) 0.5283(4) 0.0439 1.0000 Uani . . . . . .
C58 C 0.6944(5) 0.6980(4) 0.6161(4) 0.0513 1.0000 Uani . . . . . .
C59 C 0.7244(5) 0.6803(4) 0.7133(4) 0.0554 1.0000 Uani . . . . . .
C60 C 0.8490(5) 0.7022(4) 0.7220(4) 0.0526 1.0000 Uani . . . . . .
C32 C 1.1823(5) 0.9265(4) 0.5639(4) 0.0496 1.0000 Uani . . . . . .
C33 C 1.3355(6) 0.8725(6) 0.5686(5) 0.0770 1.0000 Uani . . . . . .
H103 H 1.2921 0.5060 0.2088 0.0599 1.0000 Uiso R . . . . .
H102 H 1.2541 0.4015 0.2792 0.0595 1.0000 Uiso R . . . . .
H302 H 1.4894 0.3920 0.2661 0.1042 1.0000 Uiso R . . . . .
H303 H 1.5331 0.3828 0.1349 0.1042 1.0000 Uiso R . . . . .
H301 H 1.4866 0.2772 0.2073 0.1039 1.0000 Uiso R . . . . .
H92 H 1.3151 0.2121 0.1824 0.0577 1.0000 Uiso R . . . . .
H91 H 1.3429 0.2103 0.0533 0.0584 1.0000 Uiso R . . . . .
H191 H 0.9178 0.4719 0.5350 0.0551 1.0000 Uiso R . . . . .
H192 H 0.9863 0.3308 0.5446 0.0555 1.0000 Uiso R . . . . .
H201 H 1.1349 0.4357 0.5807 0.0797 1.0000 Uiso R . . . . .
H203 H 1.1543 0.4895 0.4612 0.0804 1.0000 Uiso R . . . . .
H202 H 1.2112 0.3514 0.4729 0.0799 1.0000 Uiso R . . . . .
H182 H 0.9747 0.5483 0.3495 0.0479 1.0000 Uiso R . . . . .
H181 H 0.9991 0.4607 0.2497 0.0467 1.0000 Uiso R . . . . .
H81 H 0.9425 0.7100 -0.0186 0.0469 1.0000 Uiso R . . . . .
H82 H 1.0305 0.5786 -0.0661 0.0472 1.0000 Uiso R . . . . .
H31 H 1.4616 0.5326 0.0352 0.0645 1.0000 Uiso R . . . . .
H41 H 1.4837 0.7230 -0.0003 0.0755 1.0000 Uiso R . . . . .
H51 H 1.2946 0.8736 -0.0270 0.0700 1.0000 Uiso R . . . . .
H61 H 1.0822 0.8307 -0.0209 0.0621 1.0000 Uiso R . . . . .
H281 H 0.9619 0.4226 0.0180 0.0504 1.0000 Uiso R . . . . .
H282 H 0.8427 0.4440 0.1317 0.0505 1.0000 Uiso R . . . . .
H291 H 0.7437 0.4422 -0.0160 0.0881 1.0000 Uiso R . . . . .
H292 H 0.7774 0.5613 -0.0525 0.0878 1.0000 Uiso R . . . . .
H101 H 0.6696 0.5584 0.0578 0.0875 1.0000 Uiso R . . . . .
H131 H 0.5667 0.7144 0.2308 0.0519 1.0000 Uiso R . . . . .
H141 H 0.3979 0.6437 0.3589 0.0602 1.0000 Uiso R . . . . .
H151 H 0.4729 0.5001 0.4786 0.0634 1.0000 Uiso R . . . . .
H161 H 0.7137 0.4260 0.4636 0.0547 1.0000 Uiso R . . . . .
H231 H 0.8201 0.2369 0.3166 0.0517 1.0000 Uiso R . . . . .
H241 H 0.7814 0.1641 0.1688 0.0600 1.0000 Uiso R . . . . .
H251 H 0.9595 0.1234 0.0037 0.0668 1.0000 Uiso R . . . . .
H261 H 1.1694 0.1708 -0.0179 0.0571 1.0000 Uiso R . . . . .
H325 H 1.0922 0.7258 0.7203 0.0552 1.0000 Uiso R . . . . .
H324 H 1.1618 0.7219 0.5893 0.0542 1.0000 Uiso R . . . . .
H317 H 0.9480 1.0492 0.4336 0.0428 1.0000 Uiso R . . . . .
H316 H 0.8913 0.9679 0.5256 0.0420 1.0000 Uiso R . . . . .
H310 H 0.6901 0.9459 0.7540 0.0525 1.0000 Uiso R . . . . .
H309 H 0.6416 0.9664 0.6479 0.0526 1.0000 Uiso R . . . . .
H304 H 0.4381 0.9701 0.7880 0.1168 1.0000 Uiso R . . . . .
H328 H 0.4751 1.0530 0.8609 0.1174 1.0000 Uiso R . . . . .
H305 H 0.4218 1.1048 0.7584 0.1172 1.0000 Uiso R . . . . .
H318 H 0.6412 1.2409 0.7985 0.0548 1.0000 Uiso R . . . . .
H319 H 0.6922 1.1090 0.8471 0.0556 1.0000 Uiso R . . . . .
H320 H 1.1981 1.0520 0.7422 0.0663 1.0000 Uiso R . . . . .
H321 H 1.2044 1.2461 0.7629 0.0727 1.0000 Uiso R . . . . .
H322 H 0.9950 1.4039 0.7839 0.0702 1.0000 Uiso R . . . . .
H323 H 0.7807 1.3569 0.7877 0.0656 1.0000 Uiso R . . . . .
H329 H 0.4444 1.2327 0.5566 0.0593 1.0000 Uiso R . . . . .
H330 H 0.3727 1.1542 0.4228 0.0654 1.0000 Uiso R . . . . .
H331 H 0.5409 1.0039 0.2989 0.0658 1.0000 Uiso R . . . . .
H332 H 0.7670 0.9266 0.3159 0.0517 1.0000 Uiso R . . . . .
H311 H 1.0231 0.9680 0.2475 0.0560 1.0000 Uiso R . . . . .
H312 H 1.0886 0.8270 0.2297 0.0560 1.0000 Uiso R . . . . .
H315 H 1.2727 0.9274 0.1900 0.0827 1.0000 Uiso R . . . . .
H313 H 1.2149 0.9759 0.3133 0.0828 1.0000 Uiso R . . . . .
H314 H 1.2855 0.8375 0.2865 0.0829 1.0000 Uiso R . . . . .
H333 H 0.7658 0.7423 0.4615 0.0536 1.0000 Uiso R . . . . .
H334 H 0.6112 0.6819 0.6093 0.0625 1.0000 Uiso R . . . . .
H335 H 0.6620 0.6513 0.7718 0.0658 1.0000 Uiso R . . . . .
H336 H 0.8700 0.6912 0.7882 0.0637 1.0000 Uiso R . . . . .
H326 H 1.1592 1.0126 0.5649 0.0595 1.0000 Uiso R . . . . .
H327 H 1.1762 0.8969 0.4972 0.0597 1.0000 Uiso R . . . . .
H307 H 1.4016 0.9006 0.5096 0.1152 1.0000 Uiso R . . . . .
H308 H 1.3466 0.8976 0.6351 0.1150 1.0000 Uiso R . . . . .
H306 H 1.3613 0.7845 0.5646 0.1153 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       300(70)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.2959(7)
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
O1 . C1 . 1.236(5) yes
C1 . N3 . 1.340(5) yes
C1 . C2 . 1.505(6) yes
N3 . C29 . 1.478(6) yes
N3 . C28 . 1.487(6) yes
C29 . C30 . 1.526(7) yes
C29 . H103 . 0.966 no
C29 . H102 . 0.967 no
C30 . H302 . 0.973 no
C30 . H303 . 0.977 no
C30 . H301 . 0.958 no
C28 . C27 . 1.518(6) yes
C28 . H92 . 0.983 no
C28 . H91 . 0.965 no
C27 . C22 . 1.391(6) yes
C27 . C26 . 1.399(6) yes
C22 . C21 . 1.505(6) yes
C22 . C23 . 1.407(6) yes
C21 . O3 . 1.226(5) yes
C21 . N2 . 1.340(5) yes
N2 . C19 . 1.475(5) yes
N2 . C18 . 1.457(5) yes
C19 . C20 . 1.496(7) yes
C19 . H191 . 0.987 no
C19 . H192 . 0.987 no
C20 . H201 . 0.987 no
C20 . H203 . 0.967 no
C20 . H202 . 0.965 no
C18 . C17 . 1.501(5) yes
C18 . H182 . 0.980 no
C18 . H181 . 0.980 no
C17 . C12 . 1.392(5) yes
C17 . C16 . 1.394(6) yes
C12 . C11 . 1.494(6) yes
C12 . C13 . 1.388(5) yes
C11 . O2 . 1.238(5) yes
C11 . N1 . 1.365(5) yes
N1 . C8 . 1.453(5) yes
N1 . C9 . 1.458(5) yes
C8 . C7 . 1.516(6) yes
C8 . H81 . 0.964 no
C8 . H82 . 0.971 no
C7 . C2 . 1.393(6) yes
C7 . C6 . 1.390(6) yes
C2 . C3 . 1.400(6) yes
C3 . C4 . 1.397(7) yes
C3 . H31 . 0.955 no
C4 . C5 . 1.349(7) yes
C4 . H41 . 0.919 no
C5 . C6 . 1.374(7) yes
C5 . H51 . 0.931 no
C6 . H61 . 0.928 no
C9 . C10 . 1.524(6) yes
C9 . H281 . 0.964 no
C9 . H282 . 0.959 no
C10 . H291 . 0.965 no
C10 . H292 . 0.947 no
C10 . H101 . 0.960 no
C13 . C14 . 1.364(6) yes
C13 . H131 . 0.951 no
C14 . C15 . 1.378(7) yes
C14 . H141 . 0.940 no
C15 . C16 . 1.377(6) yes
C15 . H151 . 0.934 no
C16 . H161 . 0.923 no
C23 . C24 . 1.375(6) yes
C23 . H231 . 0.946 no
C24 . C25 . 1.361(7) yes
C24 . H241 . 0.928 no
C25 . C26 . 1.369(7) yes
C25 . H251 . 0.923 no
C26 . H261 . 0.934 no
O4 . C31 . 1.233(5) yes
C31 . N4 . 1.352(6) yes
C31 . C46 . 1.500(7) yes
N4 . C34 . 1.469(6) yes
N4 . C32 . 1.476(6) yes
C34 . C35 . 1.538(6) yes
C34 . H325 . 0.980 no
C34 . H324 . 0.990 no
C35 . C36 . 1.389(6) yes
C35 . C60 . 1.380(6) yes
C36 . C37 . 1.512(6) yes
C36 . C57 . 1.400(6) yes
C37 . O5 . 1.221(5) yes
C37 . N5 . 1.344(5) yes
N5 . C40 . 1.439(5) yes
N5 . C38 . 1.475(5) yes
C40 . C41 . 1.526(5) yes
C40 . H317 . 0.962 no
C40 . H316 . 0.948 no
C41 . C42 . 1.394(5) yes
C41 . C56 . 1.382(6) yes
C42 . C43 . 1.498(6) yes
C42 . C53 . 1.390(6) yes
C43 . O6 . 1.223(5) yes
C43 . N6 . 1.365(5) yes
N6 . C51 . 1.458(5) yes
N6 . C44 . 1.458(5) yes
C51 . C52 . 1.511(7) yes
C51 . H310 . 0.968 no
C51 . H309 . 0.971 no
C52 . H304 . 0.960 no
C52 . H328 . 0.973 no
C52 . H305 . 0.961 no
C44 . C45 . 1.540(6) yes
C44 . H318 . 0.978 no
C44 . H319 . 0.998 no
C45 . C46 . 1.380(6) yes
C45 . C50 . 1.371(6) yes
C46 . C47 . 1.403(6) yes
C47 . C48 . 1.379(7) yes
C47 . H320 . 0.933 no
C48 . C49 . 1.373(8) yes
C48 . H321 . 0.943 no
C49 . C50 . 1.368(7) yes
C49 . H322 . 0.950 no
C50 . H323 . 0.954 no
C53 . C54 . 1.374(7) yes
C53 . H329 . 0.964 no
C54 . C55 . 1.386(7) yes
C54 . H330 . 0.949 no
C55 . C56 . 1.371(6) yes
C55 . H331 . 0.944 no
C56 . H332 . 0.911 no
C38 . C39 . 1.483(7) yes
C38 . H311 . 0.998 no
C38 . H312 . 0.966 no
C39 . H315 . 0.989 no
C39 . H313 . 0.975 no
C39 . H314 . 0.980 no
C57 . C58 . 1.368(7) yes
C57 . H333 . 0.939 no
C58 . C59 . 1.366(7) yes
C58 . H334 . 0.937 no
C59 . C60 . 1.385(7) yes
C59 . H335 . 0.944 no
C60 . H336 . 0.933 no
C32 . C33 . 1.515(7) yes
C32 . H326 . 0.962 no
C32 . H327 . 0.963 no
C33 . H307 . 0.964 no
C33 . H308 . 0.963 no
C33 . H306 . 0.982 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
O1 . C1 . N3 . 120.7(4) yes
O1 . C1 . C2 . 118.5(4) yes
N3 . C1 . C2 . 120.7(4) yes
C1 . N3 . C29 . 126.2(4) yes
C1 . N3 . C28 . 117.8(3) yes
C29 . N3 . C28 . 115.7(3) yes
N3 . C29 . C30 . 111.8(4) yes
N3 . C29 . H103 . 108.7 no
C30 . C29 . H103 . 111.4 no
N3 . C29 . H102 . 109.6 no
C30 . C29 . H102 . 108.8 no
H103 . C29 . H102 . 106.4 no
C29 . C30 . H302 . 107.5 no
C29 . C30 . H303 . 109.1 no
H302 . C30 . H303 . 111.9 no
C29 . C30 . H301 . 107.7 no
H302 . C30 . H301 . 109.1 no
H303 . C30 . H301 . 111.4 no
N3 . C28 . C27 . 114.4(3) yes
N3 . C28 . H92 . 107.0 no
C27 . C28 . H92 . 108.4 no
N3 . C28 . H91 . 106.8 no
C27 . C28 . H91 . 109.4 no
H92 . C28 . H91 . 110.8 no
C28 . C27 . C22 . 122.1(4) yes
C28 . C27 . C26 . 119.4(4) yes
C22 . C27 . C26 . 118.5(4) yes
C27 . C22 . C21 . 124.7(3) yes
C27 . C22 . C23 . 119.3(4) yes
C21 . C22 . C23 . 115.7(3) yes
C22 . C21 . O3 . 118.5(4) yes
C22 . C21 . N2 . 118.7(3) yes
O3 . C21 . N2 . 122.6(4) yes
C21 . N2 . C19 . 119.3(3) yes
C21 . N2 . C18 . 121.6(3) yes
C19 . N2 . C18 . 118.5(3) yes
N2 . C19 . C20 . 113.9(4) yes
N2 . C19 . H191 . 109.6 no
C20 . C19 . H191 . 108.2 no
N2 . C19 . H192 . 109.3 no
C20 . C19 . H192 . 106.8 no
H191 . C19 . H192 . 108.8 no
C19 . C20 . H201 . 111.6 no
C19 . C20 . H203 . 110.2 no
H201 . C20 . H203 . 111.3 no
C19 . C20 . H202 . 105.8 no
H201 . C20 . H202 . 109.8 no
H203 . C20 . H202 . 108.0 no
N2 . C18 . C17 . 117.1(3) yes
N2 . C18 . H182 . 107.6 no
C17 . C18 . H182 . 106.6 no
N2 . C18 . H181 . 108.5 no
C17 . C18 . H181 . 108.1 no
H182 . C18 . H181 . 108.7 no
C18 . C17 . C12 . 118.7(3) yes
C18 . C17 . C16 . 123.3(4) yes
C12 . C17 . C16 . 118.1(4) yes
C17 . C12 . C11 . 121.2(3) yes
C17 . C12 . C13 . 120.2(4) yes
C11 . C12 . C13 . 118.6(3) yes
C12 . C11 . O2 . 121.0(4) yes
C12 . C11 . N1 . 118.3(4) yes
O2 . C11 . N1 . 120.7(4) yes
C11 . N1 . C8 . 118.0(3) yes
C11 . N1 . C9 . 121.5(3) yes
C8 . N1 . C9 . 116.7(3) yes
N1 . C8 . C7 . 116.6(3) yes
N1 . C8 . H81 . 107.8 no
C7 . C8 . H81 . 109.0 no
N1 . C8 . H82 . 105.6 no
C7 . C8 . H82 . 108.0 no
H81 . C8 . H82 . 109.6 no
C8 . C7 . C2 . 123.8(4) yes
C8 . C7 . C6 . 118.2(4) yes
C2 . C7 . C6 . 117.9(4) yes
C1 . C2 . C7 . 121.8(4) yes
C1 . C2 . C3 . 118.9(4) yes
C7 . C2 . C3 . 118.9(4) yes
C2 . C3 . C4 . 121.3(5) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 118.6 no
C3 . C4 . C5 . 119.3(5) yes
C3 . C4 . H41 . 118.8 no
C5 . C4 . H41 . 122.0 no
C4 . C5 . C6 . 120.0(5) yes
C4 . C5 . H51 . 119.9 no
C6 . C5 . H51 . 120.1 no
C7 . C6 . C5 . 122.6(5) yes
C7 . C6 . H61 . 117.1 no
C5 . C6 . H61 . 120.3 no
N1 . C9 . C10 . 112.1(4) yes
N1 . C9 . H281 . 108.7 no
C10 . C9 . H281 . 109.5 no
N1 . C9 . H282 . 108.4 no
C10 . C9 . H282 . 108.2 no
H281 . C9 . H282 . 109.9 no
C9 . C10 . H291 . 110.5 no
C9 . C10 . H292 . 114.7 no
H291 . C10 . H292 . 106.8 no
C9 . C10 . H101 . 111.1 no
H291 . C10 . H101 . 107.8 no
H292 . C10 . H101 . 105.5 no
C12 . C13 . C14 . 120.9(4) yes
C12 . C13 . H131 . 118.5 no
C14 . C13 . H131 . 120.6 no
C13 . C14 . C15 . 119.5(4) yes
C13 . C14 . H141 . 118.8 no
C15 . C14 . H141 . 121.7 no
C14 . C15 . C16 . 120.4(4) yes
C14 . C15 . H151 . 120.2 no
C16 . C15 . H151 . 119.4 no
C17 . C16 . C15 . 120.9(4) yes
C17 . C16 . H161 . 119.6 no
C15 . C16 . H161 . 119.6 no
C22 . C23 . C24 . 119.6(4) yes
C22 . C23 . H231 . 120.0 no
C24 . C23 . H231 . 120.4 no
C23 . C24 . C25 . 121.5(4) yes
C23 . C24 . H241 . 118.3 no
C25 . C24 . H241 . 120.2 no
C24 . C25 . C26 . 119.3(4) yes
C24 . C25 . H251 . 121.5 no
C26 . C25 . H251 . 119.2 no
C27 . C26 . C25 . 121.6(4) yes
C27 . C26 . H261 . 119.7 no
C25 . C26 . H261 . 118.6 no
O4 . C31 . N4 . 120.4(4) yes
O4 . C31 . C46 . 119.5(4) yes
N4 . C31 . C46 . 120.1(4) yes
C31 . N4 . C34 . 118.3(4) yes
C31 . N4 . C32 . 125.0(4) yes
C34 . N4 . C32 . 116.3(3) yes
N4 . C34 . C35 . 114.1(3) yes
N4 . C34 . H325 . 109.8 no
C35 . C34 . H325 . 108.6 no
N4 . C34 . H324 . 106.9 no
C35 . C34 . H324 . 106.7 no
H325 . C34 . H324 . 110.8 no
C34 . C35 . C36 . 122.4(4) yes
C34 . C35 . C60 . 118.3(4) yes
C36 . C35 . C60 . 119.2(4) yes
C35 . C36 . C37 . 124.5(4) yes
C35 . C36 . C57 . 118.5(4) yes
C37 . C36 . C57 . 116.4(4) yes
C36 . C37 . O5 . 118.9(4) yes
C36 . C37 . N5 . 117.6(3) yes
O5 . C37 . N5 . 123.2(4) yes
C37 . N5 . C40 . 121.9(3) yes
C37 . N5 . C38 . 118.5(3) yes
C40 . N5 . C38 . 118.7(3) yes
N5 . C40 . C41 . 116.4(3) yes
N5 . C40 . H317 . 108.1 no
C41 . C40 . H317 . 109.1 no
N5 . C40 . H316 . 107.3 no
C41 . C40 . H316 . 106.7 no
H317 . C40 . H316 . 109.1 no
C40 . C41 . C42 . 118.2(3) yes
C40 . C41 . C56 . 123.2(3) yes
C42 . C41 . C56 . 118.6(4) yes
C41 . C42 . C43 . 121.6(3) yes
C41 . C42 . C53 . 120.2(4) yes
C43 . C42 . C53 . 118.2(4) yes
C42 . C43 . O6 . 120.8(4) yes
C42 . C43 . N6 . 118.4(4) yes
O6 . C43 . N6 . 120.8(4) yes
C43 . N6 . C51 . 122.5(3) yes
C43 . N6 . C44 . 117.6(4) yes
C51 . N6 . C44 . 116.7(3) yes
N6 . C51 . C52 . 113.2(4) yes
N6 . C51 . H310 . 108.7 no
C52 . C51 . H310 . 108.2 no
N6 . C51 . H309 . 108.4 no
C52 . C51 . H309 . 110.2 no
H310 . C51 . H309 . 108.0 no
C51 . C52 . H304 . 109.8 no
C51 . C52 . H328 . 108.5 no
H304 . C52 . H328 . 107.7 no
C51 . C52 . H305 . 109.8 no
H304 . C52 . H305 . 109.5 no
H328 . C52 . H305 . 111.6 no
N6 . C44 . C45 . 116.4(3) yes
N6 . C44 . H318 . 106.3 no
C45 . C44 . H318 . 107.9 no
N6 . C44 . H319 . 106.1 no
C45 . C44 . H319 . 108.6 no
H318 . C44 . H319 . 111.6 no
C44 . C45 . C46 . 123.2(4) yes
C44 . C45 . C50 . 117.5(4) yes
C46 . C45 . C50 . 119.2(4) yes
C31 . C46 . C45 . 122.8(4) yes
C31 . C46 . C47 . 119.4(4) yes
C45 . C46 . C47 . 117.6(4) yes
C46 . C47 . C48 . 121.9(5) yes
C46 . C47 . H320 . 118.6 no
C48 . C47 . H320 . 119.5 no
C47 . C48 . C49 . 119.7(5) yes
C47 . C48 . H321 . 119.5 no
C49 . C48 . H321 . 120.8 no
C48 . C49 . C50 . 118.1(5) yes
C48 . C49 . H322 . 120.1 no
C50 . C49 . H322 . 121.8 no
C45 . C50 . C49 . 123.5(5) yes
C45 . C50 . H323 . 115.6 no
C49 . C50 . H323 . 120.9 no
C42 . C53 . C54 . 120.2(4) yes
C42 . C53 . H329 . 118.0 no
C54 . C53 . H329 . 121.8 no
C53 . C54 . C55 . 119.6(4) yes
C53 . C54 . H330 . 120.1 no
C55 . C54 . H330 . 120.3 no
C54 . C55 . C56 . 120.2(4) yes
C54 . C55 . H331 . 120.2 no
C56 . C55 . H331 . 119.5 no
C41 . C56 . C55 . 121.1(4) yes
C41 . C56 . H332 . 120.0 no
C55 . C56 . H332 . 118.9 no
N5 . C38 . C39 . 114.9(4) yes
N5 . C38 . H311 . 107.0 no
C39 . C38 . H311 . 107.6 no
N5 . C38 . H312 . 109.0 no
C39 . C38 . H312 . 110.3 no
H311 . C38 . H312 . 107.7 no
C38 . C39 . H315 . 111.7 no
C38 . C39 . H313 . 110.5 no
H315 . C39 . H313 . 108.1 no
C38 . C39 . H314 . 110.7 no
H315 . C39 . H314 . 108.5 no
H313 . C39 . H314 . 107.2 no
C36 . C57 . C58 . 120.9(4) yes
C36 . C57 . H333 . 119.7 no
C58 . C57 . H333 . 119.4 no
C57 . C58 . C59 . 121.0(4) yes
C57 . C58 . H334 . 120.1 no
C59 . C58 . H334 . 118.9 no
C58 . C59 . C60 . 118.5(4) yes
C58 . C59 . H335 . 119.7 no
C60 . C59 . H335 . 121.8 no
C59 . C60 . C35 . 121.9(4) yes
C59 . C60 . H336 . 119.2 no
C35 . C60 . H336 . 118.9 no
N4 . C32 . C33 . 112.0(4) yes
N4 . C32 . H326 . 109.6 no
C33 . C32 . H326 . 110.5 no
N4 . C32 . H327 . 107.2 no
C33 . C32 . H327 . 107.4 no
H326 . C32 . H327 . 109.9 no
C32 . C33 . H307 . 109.6 no
C32 . C33 . H308 . 110.7 no
H307 . C33 . H308 . 106.9 no
C32 . C33 . H306 . 111.1 no
H307 . C33 . H306 . 109.9 no
H308 . C33 . H306 . 108.5 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
C20 . H203 . O5 . 161.36(14) 0.967 2.426 3.356(7) yes
C18 . H182 . O5 . 163.49(11) 0.980 2.573 3.523(7) yes
C9 . H281 . O1 . 137.38(12) 0.964 2.518 3.292(7) yes
C16 . H161 . O6 1_545 162.41(13) 0.923 2.433 3.324(7) yes
C40 . H317 . O3 1_565 168.46(10) 0.962 2.566 3.514(7) yes
C51 . H310 . O4 . 140.02(12) 0.968 2.549 3.349(7) yes
C56 . H332 . O2 . 163.63(13) 0.911 2.437 3.322(7) yes
C39 . H313 . O3 1_565 154.55(14) 0.975 2.468 3.374(7) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 09/09/13 at 09:30:12
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (  29,X'S) H   ( 103,X'S) H   ( 102,X'S) 
RIDE C   (  30,X'S) H   ( 302,X'S) H   ( 303,X'S) H   ( 301,X'S) 
RIDE C   (  28,X'S) H   (  92,X'S) H   (  91,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 203,X'S) H   ( 202,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   9,X'S) H   ( 281,X'S) H   ( 282,X'S) 
RIDE C   (  10,X'S) H   ( 291,X'S) H   ( 292,X'S) H   ( 101,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  34,X'S) H   ( 325,X'S) H   ( 324,X'S) 
RIDE C   (  40,X'S) H   ( 317,X'S) H   ( 316,X'S) 
RIDE C   (  51,X'S) H   ( 310,X'S) H   ( 309,X'S) 
RIDE C   (  52,X'S) H   ( 304,X'S) H   ( 328,X'S) H   ( 305,X'S) 
RIDE C   (  44,X'S) H   ( 318,X'S) H   ( 319,X'S) 
RIDE C   (  47,X'S) H   ( 320,X'S) 
RIDE C   (  48,X'S) H   ( 321,X'S) 
RIDE C   (  49,X'S) H   ( 322,X'S) 
RIDE C   (  50,X'S) H   ( 323,X'S) 
RIDE C   (  53,X'S) H   ( 329,X'S) 
RIDE C   (  54,X'S) H   ( 330,X'S) 
RIDE C   (  55,X'S) H   ( 331,X'S) 
RIDE C   (  56,X'S) H   ( 332,X'S) 
RIDE C   (  38,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  39,X'S) H   ( 315,X'S) H   ( 313,X'S) H   ( 314,X'S) 
RIDE C   (  57,X'S) H   ( 333,X'S) 
RIDE C   (  58,X'S) H   ( 334,X'S) 
RIDE C   (  59,X'S) H   ( 335,X'S) 
RIDE C   (  60,X'S) H   ( 336,X'S) 
RIDE C   (  32,X'S) H   ( 326,X'S) H   ( 327,X'S) 
RIDE C   (  33,X'S) H   ( 307,X'S) H   ( 308,X'S) H   ( 306,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 09/09/13 at 09:30:12
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: This x-ray structure will be part of a publication dealing with
 synthesis and conformational analysis of novel macrocycles in solution and in
 solid state. The number of authors is then fully justified since it does not
 concerned only X-ray diffraction studies.
;
_vrf_PLAT027_I                   
;
PROBLEM: _diffrn_reflns_theta_full (too) Low ............      23.77 Deg.  
RESPONSE: The wavelength (0.71 ang) and the crystal-to-detector distance (40 mm)
 were selected for a correct measuring of the intensity of an enough number of
 reflections, without severe overlapping. Crystals exhibited weak diffracting
 power. The crystal used for the experiment was of good quality but too
 small to provide usable data to higher angles. Electron density maps revealed
 the presence of disordered solvent that may diminish the effective resolution
 of a data set.
;
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 967256'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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 
#  to carry out CIF format checking respectively.
#
data_o-3b

_audit_creation_date             2014-01-15T22:44:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
  ?
;
_chemical_formula_moiety         'C66 H78 N6 O6, 2.67(C2 H3 N), 0.59(H2 O)'
_chemical_formula_sum            'C71.34 H87.20 N8.67 O6.59'
_chemical_formula_weight         1171.71
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   33.119(2)
_cell_length_b                   14.712(3)
_cell_length_c                   27.909(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     13599(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5654
_cell_measurement_theta_min      4.92
_cell_measurement_theta_max      20.18
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5029.6
_exptl_special_details           
;
  ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.1608
_diffrn_reflns_av_unetI/netI     0.0777
_diffrn_reflns_number            60660
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         20.18
_diffrn_reflns_theta_full        20.18
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             6501
_reflns_number_gt                4796
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement. R-factors based
  on F² 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/[σ²(Fo²)+(0.0703P)²+56.6601P] where
P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6501
_refine_ls_number_parameters     818
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1524
_refine_ls_R_factor_gt           0.114
_refine_ls_wR_factor_ref         0.2466
_refine_ls_wR_factor_gt          0.229
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_restrained_S_all      1.225
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.064



#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 O 0.25576(17) 0.6305(4) -0.1103(2) 0.0470(19) Uani 1 1 d . . .
O2 O 0.12401(16) 0.7535(4) 0.0063(2) 0.0316(15) Uani 1 1 d . . .
O3 O 0.11706(16) 0.4839(4) 0.1306(2) 0.0310(15) Uani 1 1 d D . .
O4 O 0.24853(16) 0.6190(4) 0.2610(2) 0.0336(16) Uani 1 1 d . . .
O5 O 0.37622(15) 0.5108(4) 0.1396(2) 0.0285(15) Uani 1 1 d . . .
O6 O 0.38905(17) 0.7716(4) 0.01807(19) 0.0309(15) Uani 1 1 d . . .
N1 N 0.37480(18) 0.6298(5) -0.0085(2) 0.0234(18) Uani 1 1 d . . .
N2 N 0.24534(18) 0.7587(5) -0.0652(2) 0.0257(18) Uani 1 1 d . . .
N3 N 0.11500(17) 0.6099(5) -0.0196(2) 0.0199(17) Uani 1 1 d . . .
N4 N 0.12935(18) 0.6247(5) 0.1601(2) 0.0212(17) Uani 1 1 d . . .
N5 N 0.25665(18) 0.4951(5) 0.2150(2) 0.0233(18) Uani 1 1 d . . .
N6 N 0.39074(18) 0.6499(4) 0.1692(2) 0.0192(17) Uani 1 1 d . . .
C1 C 0.3819(2) 0.5304(5) -0.0093(3) 0.024(2) Uani 1 1 d . . .
H1 H 0.409 0.5194 0.0053 0.029 Uiso 1 1 calc R . .
C2 C 0.3501(2) 0.4817(5) 0.0230(3) 0.030(2) Uani 1 1 d . . .
H2A H 0.3228 0.4976 0.0122 0.045 Uiso 1 1 calc R . .
H2B H 0.3536 0.5012 0.0564 0.045 Uiso 1 1 calc R . .
H2C H 0.3538 0.4157 0.0209 0.045 Uiso 1 1 calc R . .
C3 C 0.3832(2) 0.4938(6) -0.0602(3) 0.027(2) Uani 1 1 d . . .
H3A H 0.3564 0.499 -0.0747 0.041 Uiso 1 1 calc R . .
H3B H 0.3914 0.4298 -0.0596 0.041 Uiso 1 1 calc R . .
H3C H 0.4027 0.5289 -0.079 0.041 Uiso 1 1 calc R . .
C4 C 0.3382(2) 0.6658(6) -0.0320(3) 0.027(2) Uani 1 1 d . . .
H4A H 0.3253 0.7102 -0.0102 0.033 Uiso 1 1 calc R . .
H4B H 0.3189 0.615 -0.0366 0.033 Uiso 1 1 calc R . .
C5 C 0.3447(2) 0.7103(5) -0.0790(3) 0.016(2) Uani 1 1 d . . .
C6 C 0.3822(3) 0.7325(6) -0.0982(3) 0.034(2) Uani 1 1 d . . .
H6 H 0.4058 0.7148 -0.0812 0.041 Uiso 1 1 calc R . .
C7 C 0.3867(3) 0.7789(6) -0.1406(3) 0.032(2) Uani 1 1 d . . .
H7 H 0.413 0.7931 -0.1519 0.038 Uiso 1 1 calc R . .
C8 C 0.3537(3) 0.8048(6) -0.1665(3) 0.028(2) Uani 1 1 d . . .
H8 H 0.3569 0.8387 -0.1953 0.034 Uiso 1 1 calc R . .
C9 C 0.3151(3) 0.7807(6) -0.1502(3) 0.029(2) Uani 1 1 d . . .
H9 H 0.2919 0.7956 -0.1687 0.035 Uiso 1 1 calc R . .
C10 C 0.3108(2) 0.7352(5) -0.1071(3) 0.023(2) Uani 1 1 d . . .
C11 C 0.2682(3) 0.7036(7) -0.0936(3) 0.032(2) Uani 1 1 d . . .
C12 C 0.2595(2) 0.8465(7) -0.0462(3) 0.035(3) Uani 1 1 d . . .
H12 H 0.289 0.8506 -0.0537 0.042 Uiso 1 1 calc R . .
C13 C 0.2557(3) 0.8499(7) 0.0081(3) 0.046(3) Uani 1 1 d . . .
H13A H 0.227 0.8516 0.0169 0.069 Uiso 1 1 calc R . .
H13B H 0.2691 0.9045 0.0202 0.069 Uiso 1 1 calc R . .
H13C H 0.2683 0.7958 0.022 0.069 Uiso 1 1 calc R . .
C14 C 0.2397(2) 0.9266(6) -0.0697(3) 0.038(3) Uani 1 1 d . . .
H14A H 0.2103 0.92 -0.0678 0.057 Uiso 1 1 calc R . .
H14B H 0.2479 0.9296 -0.1034 0.057 Uiso 1 1 calc R . .
H14C H 0.2479 0.9826 -0.0533 0.057 Uiso 1 1 calc R . .
C15 C 0.2050(2) 0.7270(7) -0.0536(3) 0.041(3) Uani 1 1 d . . .
H15A H 0.1969 0.7542 -0.0226 0.049 Uiso 1 1 calc R . .
H15B H 0.2061 0.6603 -0.0491 0.049 Uiso 1 1 calc R . .
C16 C 0.1721(2) 0.7482(6) -0.0907(3) 0.029(2) Uani 1 1 d . . .
C17 C 0.1801(2) 0.7837(6) -0.1351(3) 0.027(2) Uani 1 1 d . . .
H17 H 0.2073 0.7925 -0.1446 0.032 Uiso 1 1 calc R . .
C18 C 0.1497(3) 0.8066(6) -0.1659(3) 0.032(2) Uani 1 1 d . . .
H18 H 0.1558 0.8349 -0.1956 0.038 Uiso 1 1 calc R . .
C19 C 0.1095(2) 0.7882(6) -0.1537(3) 0.030(2) Uani 1 1 d . . .
H19 H 0.0885 0.8014 -0.1757 0.036 Uiso 1 1 calc R . .
C20 C 0.1005(2) 0.7513(6) -0.1101(3) 0.029(2) Uani 1 1 d . . .
H20 H 0.0733 0.7392 -0.1017 0.035 Uiso 1 1 calc R . .
C21 C 0.1329(2) 0.7305(5) -0.0765(3) 0.018(2) Uani 1 1 d . . .
C22 C 0.1228(2) 0.6998(6) -0.0279(3) 0.020(2) Uani 1 1 d . . .
C23 C 0.1141(2) 0.5386(5) -0.0573(3) 0.022(2) Uani 1 1 d . . .
H23 H 0.1117 0.57 -0.089 0.026 Uiso 1 1 calc R . .
C24 C 0.1538(3) 0.4841(6) -0.0576(3) 0.043(3) Uani 1 1 d . . .
H24A H 0.1578 0.4556 -0.0262 0.065 Uiso 1 1 calc R . .
H24B H 0.1764 0.525 -0.0645 0.065 Uiso 1 1 calc R . .
H24C H 0.1524 0.4369 -0.0824 0.065 Uiso 1 1 calc R . .
C25 C 0.0791(2) 0.4767(6) -0.0524(3) 0.034(2) Uani 1 1 d . . .
H25A H 0.0545 0.5125 -0.0475 0.051 Uiso 1 1 calc R . .
H25B H 0.0833 0.4363 -0.025 0.051 Uiso 1 1 calc R . .
H25C H 0.0763 0.4403 -0.0817 0.051 Uiso 1 1 calc R . .
C26 C 0.1125(2) 0.5814(6) 0.0307(3) 0.026(2) Uani 1 1 d . . .
H26A H 0.1356 0.608 0.0482 0.031 Uiso 1 1 calc R . .
H26B H 0.1153 0.5144 0.0321 0.031 Uiso 1 1 calc R . .
C27 C 0.0738(2) 0.6078(6) 0.0564(3) 0.029(2) Uani 1 1 d . . .
C28 C 0.0400(2) 0.6396(6) 0.0314(3) 0.027(2) Uani 1 1 d . . .
H28 H 0.041 0.6469 -0.0024 0.032 Uiso 1 1 calc R . .
C29 C 0.0049(2) 0.6606(5) 0.0565(3) 0.029(2) Uani 1 1 d . . .
H29 H -0.0179 0.6833 0.0397 0.035 Uiso 1 1 calc R . .
C30 C 0.0029(2) 0.6489(6) 0.1053(3) 0.031(2) Uani 1 1 d . . .
H30 H -0.0216 0.6609 0.1219 0.037 Uiso 1 1 calc R . .
C31 C 0.0365(2) 0.6196(6) 0.1305(3) 0.026(2) Uani 1 1 d . . .
H31 H 0.0353 0.6123 0.1642 0.031 Uiso 1 1 calc R . .
C32 C 0.0722(2) 0.6008(6) 0.1057(3) 0.026(2) Uani 1 1 d . . .
C33 C 0.1081(2) 0.5641(7) 0.1335(3) 0.022(2) Uani 1 1 d . . .
C34 C 0.1225(2) 0.7250(6) 0.1603(3) 0.029(2) Uani 1 1 d . . .
H34 H 0.095 0.7357 0.1464 0.035 Uiso 1 1 calc R . .
C35 C 0.1522(2) 0.7750(6) 0.1289(3) 0.033(2) Uani 1 1 d . . .
H35A H 0.1496 0.7537 0.0958 0.05 Uiso 1 1 calc R . .
H35B H 0.1797 0.7633 0.1403 0.05 Uiso 1 1 calc R . .
H35C H 0.1467 0.8403 0.1303 0.05 Uiso 1 1 calc R . .
C36 C 0.1216(3) 0.7601(6) 0.2111(3) 0.040(3) Uani 1 1 d . . .
H36A H 0.1175 0.8261 0.2108 0.061 Uiso 1 1 calc R . .
H36B H 0.1474 0.7461 0.2268 0.061 Uiso 1 1 calc R . .
H36C H 0.0995 0.7309 0.2287 0.061 Uiso 1 1 calc R . .
C37 C 0.1661(2) 0.5885(6) 0.1835(3) 0.027(2) Uani 1 1 d . . .
H37A H 0.1852 0.6395 0.1883 0.033 Uiso 1 1 calc R . .
H37B H 0.1791 0.5451 0.1611 0.033 Uiso 1 1 calc R . .
C38 C 0.1601(2) 0.5407(6) 0.2316(3) 0.026(2) Uani 1 1 d . . .
C39 C 0.1210(2) 0.5149(5) 0.2474(3) 0.020(2) Uani 1 1 d . . .
H39 H 0.0978 0.5299 0.229 0.024 Uiso 1 1 calc R . .
C40 C 0.1172(2) 0.4679(6) 0.2897(3) 0.028(2) Uani 1 1 d . . .
H40 H 0.091 0.4518 0.3006 0.034 Uiso 1 1 calc R . .
C41 C 0.1507(3) 0.4433(6) 0.3168(3) 0.029(2) Uani 1 1 d . . .
H41 H 0.1476 0.4096 0.3456 0.035 Uiso 1 1 calc R . .
C42 C 0.1884(3) 0.4689(5) 0.3011(3) 0.027(2) Uani 1 1 d . . .
H42 H 0.2115 0.4537 0.3197 0.032 Uiso 1 1 calc R . .
C43 C 0.1933(2) 0.5162(5) 0.2588(3) 0.020(2) Uani 1 1 d . . .
C44 C 0.2349(2) 0.5486(6) 0.2446(3) 0.021(2) Uani 1 1 d . . .
C45 C 0.2412(2) 0.4096(6) 0.1944(3) 0.026(2) Uani 1 1 d . . .
H45 H 0.2117 0.4076 0.2019 0.031 Uiso 1 1 calc R . .
C46 C 0.2448(3) 0.4080(6) 0.1395(3) 0.039(3) Uani 1 1 d . . .
H46A H 0.2258 0.3635 0.1264 0.058 Uiso 1 1 calc R . .
H46B H 0.2724 0.391 0.1304 0.058 Uiso 1 1 calc R . .
H46C H 0.2386 0.4684 0.1266 0.058 Uiso 1 1 calc R . .
C47 C 0.2599(2) 0.3264(6) 0.2183(3) 0.042(3) Uani 1 1 d . . .
H47A H 0.2526 0.3255 0.2523 0.062 Uiso 1 1 calc R . .
H47B H 0.2893 0.3289 0.2151 0.062 Uiso 1 1 calc R . .
H47C H 0.2497 0.2712 0.2027 0.062 Uiso 1 1 calc R . .
C48 C 0.2969(2) 0.5264(6) 0.2018(3) 0.031(2) Uani 1 1 d . . .
H48A H 0.296 0.5933 0.1978 0.037 Uiso 1 1 calc R . .
H48B H 0.3039 0.4998 0.1703 0.037 Uiso 1 1 calc R . .
C49 C 0.3307(2) 0.5036(5) 0.2372(3) 0.021(2) Uani 1 1 d . . .
C50 C 0.3242(2) 0.4653(5) 0.2813(3) 0.027(2) Uani 1 1 d . . .
H50 H 0.2974 0.4517 0.2907 0.033 Uiso 1 1 calc R . .
C51 C 0.3557(2) 0.4456(6) 0.3126(3) 0.026(2) Uani 1 1 d . . .
H51 H 0.3505 0.4174 0.3426 0.032 Uiso 1 1 calc R . .
C52 C 0.3946(3) 0.4678(6) 0.2992(3) 0.030(2) Uani 1 1 d . . .
H52 H 0.4166 0.4553 0.3201 0.036 Uiso 1 1 calc R . .
C53 C 0.4016(2) 0.5087(6) 0.2549(3) 0.029(2) Uani 1 1 d . . .
H53 H 0.4284 0.5241 0.2459 0.034 Uiso 1 1 calc R . .
C54 C 0.3713(2) 0.5265(5) 0.2250(3) 0.0193(18) Uani 1 1 d U . .
C55 C 0.3796(2) 0.5632(6) 0.1740(3) 0.0192(18) Uani 1 1 d U . .
C56 C 0.3890(2) 0.7167(5) 0.2081(3) 0.024(2) Uani 1 1 d . . .
H56 H 0.3869 0.6826 0.239 0.029 Uiso 1 1 calc R . .
C57 C 0.3514(2) 0.7791(6) 0.2039(3) 0.037(3) Uani 1 1 d . . .
H57A H 0.3268 0.742 0.2054 0.055 Uiso 1 1 calc R . .
H57B H 0.3522 0.8117 0.1732 0.055 Uiso 1 1 calc R . .
H57C H 0.3514 0.8231 0.2302 0.055 Uiso 1 1 calc R . .
C58 C 0.4275(2) 0.7765(6) 0.2107(3) 0.044(3) Uani 1 1 d . . .
H58A H 0.4294 0.8139 0.1817 0.066 Uiso 1 1 calc R . .
H58B H 0.4513 0.7375 0.2131 0.066 Uiso 1 1 calc R . .
H58C H 0.426 0.8161 0.2389 0.066 Uiso 1 1 calc R . .
C59 C 0.3943(2) 0.6824(6) 0.1196(3) 0.027(2) Uani 1 1 d . . .
H59A H 0.3931 0.7497 0.1197 0.033 Uiso 1 1 calc R . .
H59B H 0.3708 0.6601 0.1011 0.033 Uiso 1 1 calc R . .
C60 C 0.4326(2) 0.6532(5) 0.0942(3) 0.018(2) Uani 1 1 d . . .
C61 C 0.4672(2) 0.6292(5) 0.1182(3) 0.024(2) Uani 1 1 d . . .
H61 H 0.4667 0.6257 0.1522 0.028 Uiso 1 1 calc R . .
C62 C 0.5030(2) 0.6099(6) 0.0943(3) 0.026(2) Uani 1 1 d . . .
H62 H 0.5267 0.5953 0.1118 0.031 Uiso 1 1 calc R . .
C63 C 0.5038(3) 0.6123(6) 0.0443(4) 0.041(3) Uani 1 1 d . . .
H63 H 0.528 0.5985 0.0277 0.05 Uiso 1 1 calc R . .
C64 C 0.4685(2) 0.6351(6) 0.0185(3) 0.029(2) Uani 1 1 d . . .
H64 H 0.4689 0.6366 -0.0155 0.035 Uiso 1 1 calc R . .
C65 C 0.4329(2) 0.6557(6) 0.0437(3) 0.026(2) Uani 1 1 d . . .
C66 C 0.3972(2) 0.6903(7) 0.0170(3) 0.020(2) Uani 1 1 d . . .
C70 C 0.2801(5) 0.6582(10) 0.1011(6) 0.059(5) Uani 0.739(15) 1 d P . .
H70A H 0.269 0.6701 0.133 0.088 Uiso 0.739(15) 1 calc PR . .
H70B H 0.2916 0.7144 0.0881 0.088 Uiso 0.739(15) 1 calc PR . .
H70C H 0.3012 0.6117 0.1033 0.088 Uiso 0.739(15) 1 calc PR . .
C71 C 0.2513(6) 0.6295(11) 0.0729(8) 0.077(6) Uani 0.739(15) 1 d P . .
N72 N 0.2244(5) 0.5956(11) 0.0447(6) 0.099(7) Uani 0.739(15) 1 d P . .
C73 C 0.0320(3) 0.3872(6) 0.0786(4) 0.036(3) Uani 0.958(13) 1 d P . .
H73A H 0.0312 0.3297 0.0609 0.053 Uiso 0.958(13) 1 calc PR . .
H73B H 0.0588 0.3949 0.093 0.053 Uiso 0.958(13) 1 calc PR . .
H73C H 0.0267 0.4377 0.0565 0.053 Uiso 0.958(13) 1 calc PR . .
C74 C 0.0020(3) 0.3863(8) 0.1155(4) 0.045(3) Uani 0.958(13) 1 d P . .
N75 N -0.0213(3) 0.3850(7) 0.1443(4) 0.074(4) Uani 0.958(13) 1 d P . .
C76 C -0.0532(3) 0.8891(7) 0.4141(4) 0.050(3) Uani 0.975(13) 1 d P . .
H76A H -0.0732 0.9047 0.3896 0.075 Uiso 0.975(13) 1 calc PR . .
H76B H -0.0531 0.9361 0.4391 0.075 Uiso 0.975(13) 1 calc PR . .
H76C H -0.0601 0.8303 0.4285 0.075 Uiso 0.975(13) 1 calc PR . .
C77 C -0.0133(4) 0.8836(7) 0.3923(4) 0.051(3) Uani 0.975(13) 1 d P . .
N78 N 0.0179(3) 0.8765(7) 0.3766(4) 0.084(4) Uani 0.975(13) 1 d P . .
O1W O 0.1655(3) 0.3709(9) 0.0734(5) 0.067(6) Uani 0.592(17) 1 d PD . .
H1W H 0.151(4) 0.396(7) 0.093(4) 0.101 Uiso 0.592(17) 1 d PD . .
H2W H 0.153(3) 0.331(5) 0.060(5) 0.101 Uiso 0.592(17) 1 d PD . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
  All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell s.u.'s are taken
  into account individually in the estimation of s.u.'s in distances, angles
  and torsion angles; correlations between s.u.'s in cell parameters are
only
  used when they are defined by crystal symmetry.  An approximate
(isotropic)
  treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 1.241(10) . ?
O2 C22 1.238(9) . ?
O3 C33 1.220(9) . ?
O4 C44 1.218(9) . ?
O5 C55 1.237(9) . ?
O6 C66 1.227(9) . ?
N1 C66 1.359(10) . ?
N1 C4 1.477(9) . ?
N1 C1 1.481(10) . ?
N2 C11 1.364(11) . ?
N2 C15 1.452(10) . ?
N2 C12 1.474(11) . ?
N3 C22 1.367(10) . ?
N3 C26 1.467(10) . ?
N3 C23 1.485(10) . ?
N4 C33 1.359(10) . ?
N4 C37 1.480(9) . ?
N4 C34 1.493(10) . ?
N5 C44 1.348(10) . ?
N5 C48 1.459(9) . ?
N5 C45 1.474(10) . ?
N6 C55 1.335(10) . ?
N6 C56 1.466(9) . ?
N6 C59 1.468(10) . ?
C1 C3 1.520(11) . ?
C1 C2 1.562(11) . ?
C1 H1 1 . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 C5 1.481(11) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.392(11) . ?
C5 C10 1.419(10) . ?
C6 C7 1.373(12) . ?
C6 H6 0.95 . ?
C7 C8 1.365(11) . ?
C7 H7 0.95 . ?
C8 C9 1.404(11) . ?
C8 H8 0.95 . ?
C9 C10 1.385(11) . ?
C9 H9 0.95 . ?
C10 C11 1.532(11) . ?
C12 C14 1.501(12) . ?
C12 C13 1.520(12) . ?
C12 H12 1 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C16 1.536(11) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.369(11) . ?
C16 C21 1.380(11) . ?
C17 C18 1.366(11) . ?
C17 H17 0.95 . ?
C18 C19 1.401(11) . ?
C18 H18 0.95 . ?
C19 C20 1.364(11) . ?
C19 H19 0.95 . ?
C20 C21 1.457(11) . ?
C20 H20 0.95 . ?
C21 C22 1.470(11) . ?
C23 C25 1.482(10) . ?
C23 C24 1.540(11) . ?
C23 H23 1 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C26 C27 1.521(11) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 C32 1.380(11) . ?
C27 C28 1.399(11) . ?
C28 C29 1.390(11) . ?
C28 H28 0.95 . ?
C29 C30 1.376(11) . ?
C29 H29 0.95 . ?
C30 C31 1.385(11) . ?
C30 H30 0.95 . ?
C31 C32 1.398(11) . ?
C31 H31 0.95 . ?
C32 C33 1.516(11) . ?
C34 C36 1.509(11) . ?
C34 C35 1.509(11) . ?
C34 H34 1 . ?
C35 H35A 0.98 . ?
C35 H35B 0.98 . ?
C35 H35C 0.98 . ?
C36 H36A 0.98 . ?
C36 H36B 0.98 . ?
C36 H36C 0.98 . ?
C37 C38 1.531(11) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
C38 C43 1.381(11) . ?
C38 C39 1.421(10) . ?
C39 C40 1.373(11) . ?
C39 H39 0.95 . ?
C40 C41 1.391(11) . ?
C40 H40 0.95 . ?
C41 C42 1.376(11) . ?
C41 H41 0.95 . ?
C42 C43 1.381(11) . ?
C42 H42 0.95 . ?
C43 C44 1.513(11) . ?
C45 C47 1.524(11) . ?
C45 C46 1.539(11) . ?
C45 H45 1 . ?
C46 H46A 0.98 . ?
C46 H46B 0.98 . ?
C46 H46C 0.98 . ?
C47 H47A 0.98 . ?
C47 H47B 0.98 . ?
C47 H47C 0.98 . ?
C48 C49 1.529(11) . ?
C48 H48A 0.99 . ?
C48 H48B 0.99 . ?
C49 C50 1.371(11) . ?
C49 C54 1.429(10) . ?
C50 C51 1.390(11) . ?
C50 H50 0.95 . ?
C51 C52 1.382(11) . ?
C51 H51 0.95 . ?
C52 C53 1.394(11) . ?
C52 H52 0.95 . ?
C53 C54 1.331(11) . ?
C53 H53 0.95 . ?
C54 C55 1.545(11) . ?
C56 C58 1.549(11) . ?
C56 C57 1.553(11) . ?
C56 H56 1 . ?
C57 H57A 0.98 . ?
C57 H57B 0.98 . ?
C57 H57C 0.98 . ?
C58 H58A 0.98 . ?
C58 H58B 0.98 . ?
C58 H58C 0.98 . ?
C59 C60 1.515(11) . ?
C59 H59A 0.99 . ?
C59 H59B 0.99 . ?
C60 C61 1.376(10) . ?
C60 C65 1.409(11) . ?
C61 C62 1.388(11) . ?
C61 H61 0.95 . ?
C62 C63 1.395(11) . ?
C62 H62 0.95 . ?
C63 C64 1.412(12) . ?
C63 H63 0.95 . ?
C64 C65 1.406(11) . ?
C64 H64 0.95 . ?
C65 C66 1.487(11) . ?
C70 C71 1.31(3) . ?
C70 H70A 0.98 . ?
C70 H70B 0.98 . ?
C70 H70C 0.98 . ?
C71 N72 1.29(3) . ?
C73 C74 1.434(14) . ?
C73 H73A 0.98 . ?
C73 H73B 0.98 . ?
C73 H73C 0.98 . ?
C74 N75 1.114(13) . ?
C76 C77 1.457(15) . ?
C76 H76A 0.98 . ?
C76 H76B 0.98 . ?
C76 H76C 0.98 . ?
C77 N78 1.126(12) . ?
O1W H1W 0.821(11) . ?
O1W H2W 0.821(11) . ?

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
C66 N1 C4 116.5(7) . . ?
C66 N1 C1 124.6(7) . . ?
C4 N1 C1 118.5(7) . . ?
C11 N2 C15 116.7(7) . . ?
C11 N2 C12 123.6(7) . . ?
C15 N2 C12 119.7(7) . . ?
C22 N3 C26 116.6(7) . . ?
C22 N3 C23 124.6(7) . . ?
C26 N3 C23 118.3(7) . . ?
C33 N4 C37 115.6(7) . . ?
C33 N4 C34 124.8(7) . . ?
C37 N4 C34 118.7(6) . . ?
C44 N5 C48 117.2(7) . . ?
C44 N5 C45 123.5(6) . . ?
C48 N5 C45 119.2(7) . . ?
C55 N6 C56 123.7(7) . . ?
C55 N6 C59 115.4(7) . . ?
C56 N6 C59 118.9(6) . . ?
N1 C1 C3 111.6(7) . . ?
N1 C1 C2 109.7(6) . . ?
C3 C1 C2 113.4(7) . . ?
N1 C1 H1 107.3 . . ?
C3 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 115.5(6) . . ?
N1 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
N1 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C6 C5 C10 115.7(7) . . ?
C6 C5 C4 125.2(7) . . ?
C10 C5 C4 119.1(7) . . ?
C7 C6 C5 123.0(8) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C8 C7 C6 120.7(8) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.1(8) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 119.8(8) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 121.6(7) . . ?
C9 C10 C11 117.0(7) . . ?
C5 C10 C11 121.0(7) . . ?
O1 C11 N2 123.2(8) . . ?
O1 C11 C10 118.5(9) . . ?
N2 C11 C10 118.2(8) . . ?
N2 C12 C14 113.0(7) . . ?
N2 C12 C13 111.2(7) . . ?
C14 C12 C13 111.9(8) . . ?
N2 C12 H12 106.8 . . ?
C14 C12 H12 106.8 . . ?
C13 C12 H12 106.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 116.0(7) . . ?
N2 C15 H15A 108.3 . . ?
C16 C15 H15A 108.3 . . ?
N2 C15 H15B 108.3 . . ?
C16 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
C17 C16 C21 120.9(7) . . ?
C17 C16 C15 123.3(7) . . ?
C21 C16 C15 115.8(7) . . ?
C18 C17 C16 121.4(8) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 119.9(8) . . ?
C17 C18 H18 120 . . ?
C19 C18 H18 120 . . ?
C20 C19 C18 120.1(8) . . ?
C20 C19 H19 120 . . ?
C18 C19 H19 120 . . ?
C19 C20 C21 119.8(7) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 117.8(7) . . ?
C16 C21 C22 122.6(7) . . ?
C20 C21 C22 119.4(7) . . ?
O2 C22 N3 119.6(8) . . ?
O2 C22 C21 120.4(8) . . ?
N3 C22 C21 119.8(8) . . ?
C25 C23 N3 112.6(7) . . ?
C25 C23 C24 110.4(7) . . ?
N3 C23 C24 110.8(6) . . ?
C25 C23 H23 107.6 . . ?
N3 C23 H23 107.6 . . ?
C24 C23 H23 107.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N3 C26 C27 115.3(7) . . ?
N3 C26 H26A 108.5 . . ?
C27 C26 H26A 108.5 . . ?
N3 C26 H26B 108.4 . . ?
C27 C26 H26B 108.4 . . ?
H26A C26 H26B 107.5 . . ?
C32 C27 C28 119.5(7) . . ?
C32 C27 C26 118.9(7) . . ?
C28 C27 C26 121.6(8) . . ?
C29 C28 C27 119.5(8) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C30 C29 C28 120.7(8) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 120.1(8) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 119.5(8) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 H31 120.3 . . ?
C27 C32 C31 120.5(7) . . ?
C27 C32 C33 120.5(7) . . ?
C31 C32 C33 118.7(8) . . ?
O3 C33 N4 123.0(8) . . ?
O3 C33 C32 120.1(8) . . ?
N4 C33 C32 116.9(8) . . ?
N4 C34 C36 110.1(7) . . ?
N4 C34 C35 112.3(7) . . ?
C36 C34 C35 113.0(7) . . ?
N4 C34 H34 107 . . ?
C36 C34 H34 107 . . ?
C35 C34 H34 107 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N4 C37 C38 116.5(6) . . ?
N4 C37 H37A 108.2 . . ?
C38 C37 H37A 108.2 . . ?
N4 C37 H37B 108.2 . . ?
C38 C37 H37B 108.2 . . ?
H37A C37 H37B 107.3 . . ?
C43 C38 C39 119.1(7) . . ?
C43 C38 C37 119.9(7) . . ?
C39 C38 C37 120.9(7) . . ?
C40 C39 C38 119.0(8) . . ?
C40 C39 H39 120.5 . . ?
C38 C39 H39 120.5 . . ?
C39 C40 C41 121.7(8) . . ?
C39 C40 H40 119.1 . . ?
C41 C40 H40 119.1 . . ?
C42 C41 C40 118.6(8) . . ?
C42 C41 H41 120.7 . . ?
C40 C41 H41 120.7 . . ?
C41 C42 C43 121.1(8) . . ?
C41 C42 H42 119.4 . . ?
C43 C42 H42 119.4 . . ?
C38 C43 C42 120.5(7) . . ?
C38 C43 C44 120.0(7) . . ?
C42 C43 C44 119.3(7) . . ?
O4 C44 N5 122.0(7) . . ?
O4 C44 C43 120.4(8) . . ?
N5 C44 C43 117.5(7) . . ?
N5 C45 C47 112.0(7) . . ?
N5 C45 C46 112.1(7) . . ?
C47 C45 C46 113.0(7) . . ?
N5 C45 H45 106.4 . . ?
C47 C45 H45 106.4 . . ?
C46 C45 H45 106.4 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
N5 C48 C49 115.8(6) . . ?
N5 C48 H48A 108.3 . . ?
C49 C48 H48A 108.3 . . ?
N5 C48 H48B 108.3 . . ?
C49 C48 H48B 108.3 . . ?
H48A C48 H48B 107.4 . . ?
C50 C49 C54 117.2(7) . . ?
C50 C49 C48 123.8(7) . . ?
C54 C49 C48 118.9(7) . . ?
C49 C50 C51 122.3(8) . . ?
C49 C50 H50 118.9 . . ?
C51 C50 H50 118.9 . . ?
C52 C51 C50 118.6(8) . . ?
C52 C51 H51 120.7 . . ?
C50 C51 H51 120.7 . . ?
C51 C52 C53 119.8(8) . . ?
C51 C52 H52 120.1 . . ?
C53 C52 H52 120.1 . . ?
C54 C53 C52 121.1(8) . . ?
C54 C53 H53 119.4 . . ?
C52 C53 H53 119.4 . . ?
C53 C54 C49 120.9(8) . . ?
C53 C54 C55 120.8(7) . . ?
C49 C54 C55 118.0(7) . . ?
O5 C55 N6 122.7(8) . . ?
O5 C55 C54 118.8(7) . . ?
N6 C55 C54 118.4(7) . . ?
N6 C56 C58 112.6(6) . . ?
N6 C56 C57 111.8(6) . . ?
C58 C56 C57 109.1(7) . . ?
N6 C56 H56 107.7 . . ?
C58 C56 H56 107.7 . . ?
C57 C56 H56 107.7 . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C56 C58 H58A 109.5 . . ?
C56 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C56 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
N6 C59 C60 114.6(7) . . ?
N6 C59 H59A 108.6 . . ?
C60 C59 H59A 108.6 . . ?
N6 C59 H59B 108.6 . . ?
C60 C59 H59B 108.6 . . ?
H59A C59 H59B 107.6 . . ?
C61 C60 C65 119.3(7) . . ?
C61 C60 C59 122.8(8) . . ?
C65 C60 C59 117.8(7) . . ?
C60 C61 C62 121.9(8) . . ?
C60 C61 H61 119.1 . . ?
C62 C61 H61 119.1 . . ?
C61 C62 C63 119.5(8) . . ?
C61 C62 H62 120.2 . . ?
C63 C62 H62 120.2 . . ?
C62 C63 C64 120.0(8) . . ?
C62 C63 H63 120 . . ?
C64 C63 H63 120 . . ?
C65 C64 C63 119.4(8) . . ?
C65 C64 H64 120.3 . . ?
C63 C64 H64 120.3 . . ?
C64 C65 C60 119.9(7) . . ?
C64 C65 C66 119.4(8) . . ?
C60 C65 C66 120.3(7) . . ?
O6 C66 N1 122.2(7) . . ?
O6 C66 C65 119.7(8) . . ?
N1 C66 C65 118.2(8) . . ?
C71 C70 H70A 109.5 . . ?
C71 C70 H70B 109.5 . . ?
H70A C70 H70B 109.5 . . ?
C71 C70 H70C 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
N72 C71 C70 175.6(18) . . ?
C74 C73 H73A 109.5 . . ?
C74 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
C74 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
N75 C74 C73 179.5(14) . . ?
C77 C76 H76A 109.5 . . ?
C77 C76 H76B 109.5 . . ?
H76A C76 H76B 109.5 . . ?
C77 C76 H76C 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
N78 C77 C76 177.2(13) . . ?
H1W O1W H2W 109(3) . . ?

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
C66 N1 C1 C3 -130.5(8) . . . . ?
C4 N1 C1 C3 57.4(9) . . . . ?
C66 N1 C1 C2 102.9(8) . . . . ?
C4 N1 C1 C2 -69.1(9) . . . . ?
C66 N1 C4 C5 83.0(9) . . . . ?
C1 N1 C4 C5 -104.3(8) . . . . ?
N1 C4 C5 C6 -10.3(12) . . . . ?
N1 C4 C5 C10 171.2(7) . . . . ?
C10 C5 C6 C7 2.7(12) . . . . ?
C4 C5 C6 C7 -175.9(8) . . . . ?
C5 C6 C7 C8 -0.8(14) . . . . ?
C6 C7 C8 C9 -2.2(13) . . . . ?
C7 C8 C9 C10 3.2(12) . . . . ?
C8 C9 C10 C5 -1.3(12) . . . . ?
C8 C9 C10 C11 -174.7(8) . . . . ?
C6 C5 C10 C9 -1.6(12) . . . . ?
C4 C5 C10 C9 177.1(8) . . . . ?
C6 C5 C10 C11 171.6(8) . . . . ?
C4 C5 C10 C11 -9.8(12) . . . . ?
C15 N2 C11 O1 1.7(12) . . . . ?
C12 N2 C11 O1 -178.6(8) . . . . ?
C15 N2 C11 C10 179.4(7) . . . . ?
C12 N2 C11 C10 -0.9(12) . . . . ?
C9 C10 C11 O1 83.4(10) . . . . ?
C5 C10 C11 O1 -90.0(10) . . . . ?
C9 C10 C11 N2 -94.4(10) . . . . ?
C5 C10 C11 N2 92.2(9) . . . . ?
C11 N2 C12 C14 108.2(9) . . . . ?
C15 N2 C12 C14 -72.1(9) . . . . ?
C11 N2 C12 C13 -125.0(8) . . . . ?
C15 N2 C12 C13 54.7(10) . . . . ?
C11 N2 C15 C16 -84.8(10) . . . . ?
C12 N2 C15 C16 95.5(10) . . . . ?
N2 C15 C16 C17 8.6(13) . . . . ?
N2 C15 C16 C21 -170.5(8) . . . . ?
C21 C16 C17 C18 3.0(14) . . . . ?
C15 C16 C17 C18 -176.1(8) . . . . ?
C16 C17 C18 C19 -4.3(13) . . . . ?
C17 C18 C19 C20 3.0(13) . . . . ?
C18 C19 C20 C21 -0.4(13) . . . . ?
C17 C16 C21 C20 -0.3(12) . . . . ?
C15 C16 C21 C20 178.8(7) . . . . ?
C17 C16 C21 C22 -174.7(8) . . . . ?
C15 C16 C21 C22 4.4(12) . . . . ?
C19 C20 C21 C16 -0.9(12) . . . . ?
C19 C20 C21 C22 173.7(8) . . . . ?
C26 N3 C22 O2 -5.8(10) . . . . ?
C23 N3 C22 O2 -177.8(6) . . . . ?
C26 N3 C22 C21 169.1(6) . . . . ?
C23 N3 C22 C21 -2.9(10) . . . . ?
C16 C21 C22 O2 73.8(11) . . . . ?
C20 C21 C22 O2 -100.5(9) . . . . ?
C16 C21 C22 N3 -101.0(9) . . . . ?
C20 C21 C22 N3 84.6(9) . . . . ?
C22 N3 C23 C25 -135.3(7) . . . . ?
C26 N3 C23 C25 52.8(9) . . . . ?
C22 N3 C23 C24 100.6(8) . . . . ?
C26 N3 C23 C24 -71.3(8) . . . . ?
C22 N3 C26 C27 75.6(9) . . . . ?
C23 N3 C26 C27 -111.8(7) . . . . ?
N3 C26 C27 C32 -166.7(8) . . . . ?
N3 C26 C27 C28 12.8(11) . . . . ?
C32 C27 C28 C29 -2.3(13) . . . . ?
C26 C27 C28 C29 178.3(8) . . . . ?
C27 C28 C29 C30 -1.2(13) . . . . ?
C28 C29 C30 C31 2.8(13) . . . . ?
C29 C30 C31 C32 -0.9(13) . . . . ?
C28 C27 C32 C31 4.1(13) . . . . ?
C26 C27 C32 C31 -176.4(8) . . . . ?
C28 C27 C32 C33 178.3(8) . . . . ?
C26 C27 C32 C33 -2.2(12) . . . . ?
C30 C31 C32 C27 -2.5(13) . . . . ?
C30 C31 C32 C33 -176.8(8) . . . . ?
C37 N4 C33 O3 3.6(11) . . . . ?
C34 N4 C33 O3 172.5(7) . . . . ?
C37 N4 C33 C32 -175.0(7) . . . . ?
C34 N4 C33 C32 -6.1(11) . . . . ?
C27 C32 C33 O3 -69.8(11) . . . . ?
C31 C32 C33 O3 104.5(10) . . . . ?
C27 C32 C33 N4 108.9(9) . . . . ?
C31 C32 C33 N4 -76.9(10) . . . . ?
C33 N4 C34 C36 133.8(8) . . . . ?
C37 N4 C34 C36 -57.7(9) . . . . ?
C33 N4 C34 C35 -99.4(8) . . . . ?
C37 N4 C34 C35 69.1(9) . . . . ?
C33 N4 C37 C38 -84.3(9) . . . . ?
C34 N4 C37 C38 106.1(8) . . . . ?
N4 C37 C38 C43 -171.1(7) . . . . ?
N4 C37 C38 C39 13.6(11) . . . . ?
C43 C38 C39 C40 1.3(12) . . . . ?
C37 C38 C39 C40 176.7(7) . . . . ?
C38 C39 C40 C41 -1.4(13) . . . . ?
C39 C40 C41 C42 1.4(13) . . . . ?
C40 C41 C42 C43 -1.4(13) . . . . ?
C39 C38 C43 C42 -1.2(12) . . . . ?
C37 C38 C43 C42 -176.7(7) . . . . ?
C39 C38 C43 C44 -175.6(7) . . . . ?
C37 C38 C43 C44 8.9(12) . . . . ?
C41 C42 C43 C38 1.3(13) . . . . ?
C41 C42 C43 C44 175.8(8) . . . . ?
C48 N5 C44 O4 -2.3(11) . . . . ?
C45 N5 C44 O4 -179.9(7) . . . . ?
C48 N5 C44 C43 -179.5(6) . . . . ?
C45 N5 C44 C43 2.8(11) . . . . ?
C38 C43 C44 O4 92.0(10) . . . . ?
C42 C43 C44 O4 -82.5(10) . . . . ?
C38 C43 C44 N5 -90.7(10) . . . . ?
C42 C43 C44 N5 94.8(9) . . . . ?
C44 N5 C45 C47 -105.9(8) . . . . ?
C48 N5 C45 C47 76.5(9) . . . . ?
C44 N5 C45 C46 125.9(8) . . . . ?
C48 N5 C45 C46 -51.7(9) . . . . ?
C44 N5 C48 C49 84.6(9) . . . . ?
C45 N5 C48 C49 -97.7(9) . . . . ?
N5 C48 C49 C50 -7.1(12) . . . . ?
N5 C48 C49 C54 175.7(7) . . . . ?
C54 C49 C50 C51 -2.6(12) . . . . ?
C48 C49 C50 C51 -179.8(8) . . . . ?
C49 C50 C51 C52 1.8(13) . . . . ?
C50 C51 C52 C53 -0.4(13) . . . . ?
C51 C52 C53 C54 -0.2(13) . . . . ?
C52 C53 C54 C49 -0.6(13) . . . . ?
C52 C53 C54 C55 -174.0(8) . . . . ?
C50 C49 C54 C53 2.0(12) . . . . ?
C48 C49 C54 C53 179.3(8) . . . . ?
C50 C49 C54 C55 175.6(7) . . . . ?
C48 C49 C54 C55 -7.1(11) . . . . ?
C56 N6 C55 O5 170.3(7) . . . . ?
C59 N6 C55 O5 6.7(11) . . . . ?
C56 N6 C55 C54 -10.8(10) . . . . ?
C59 N6 C55 C54 -174.4(6) . . . . ?
C53 C54 C55 O5 104.3(9) . . . . ?
C49 C54 C55 O5 -69.3(10) . . . . ?
C53 C54 C55 N6 -74.7(10) . . . . ?
C49 C54 C55 N6 111.7(8) . . . . ?
C55 N6 C56 C58 136.0(8) . . . . ?
C59 N6 C56 C58 -60.9(9) . . . . ?
C55 N6 C56 C57 -100.8(9) . . . . ?
C59 N6 C56 C57 62.3(9) . . . . ?
C55 N6 C59 C60 -78.0(8) . . . . ?
C56 N6 C59 C60 117.6(7) . . . . ?
N6 C59 C60 C61 -23.3(11) . . . . ?
N6 C59 C60 C65 160.1(7) . . . . ?
C65 C60 C61 C62 2.0(12) . . . . ?
C59 C60 C61 C62 -174.5(8) . . . . ?
C60 C61 C62 C63 -1.9(13) . . . . ?
C61 C62 C63 C64 0.7(13) . . . . ?
C62 C63 C64 C65 0.3(13) . . . . ?
C63 C64 C65 C60 -0.1(12) . . . . ?
C63 C64 C65 C66 172.8(8) . . . . ?
C61 C60 C65 C64 -1.0(12) . . . . ?
C59 C60 C65 C64 175.7(7) . . . . ?
C61 C60 C65 C66 -173.9(7) . . . . ?
C59 C60 C65 C66 2.8(11) . . . . ?
C4 N1 C66 O6 -4.7(11) . . . . ?
C1 N1 C66 O6 -176.9(7) . . . . ?
C4 N1 C66 C65 176.3(7) . . . . ?
C1 N1 C66 C65 4.1(11) . . . . ?
C64 C65 C66 O6 -102.4(10) . . . . ?
C60 C65 C66 O6 70.5(11) . . . . ?
C64 C65 C66 N1 76.6(10) . . . . ?
C60 C65 C66 N1 -110.4(9) . . . . ?

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
O1W H1W O3 0.821(11) 2.01(3) 2.807(12) 165(12) .
O1W H2W O6 0.821(11) 2.01(3) 2.789(13) 160(9) 7_655

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


_database_code_depnum_ccdc_archive 'CCDC 982403'
