# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pyn1604SN
_database_code_depnum_ccdc_archive 'CCDC 1922203'
loop_
_audit_author_name
_audit_author_address
'Anthony Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-03 downloaded from the CCDC.
;
_audit_creation_date             16-03-15
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\pyn1604SN\Tony_pyn1604CSN_dat At 11:15 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.3603(1)
_cell_length_b                   16.0890(2)
_cell_length_c                   16.5566(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.3726(8)
_cell_angle_gamma                90
_cell_volume                     1958.95(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 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'
O 0.0492 0.0322 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'


_cell_formula_units_Z            4

# Given Formula = C23 H22 N2 O2 
# Dc =      1.22 Fooo =    768.00 Mu =      6.20 M =    716.88
# Found Formula = C23 H24 N2 O2 
# Dc =      1.22 FOOO =    768.00 Mu =      6.20 M =    720.91

_chemical_formula_sum            'C23 H24 N2 O2'
_chemical_formula_moiety         'C23 H24 N2 O2'
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_weight         360.46


_cell_measurement_reflns_used    18719
_cell_measurement_theta_min      3
_cell_measurement_theta_max      72
_cell_measurement_temperature    150

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale brown'
_exptl_crystal_size_min          0.073
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_max          0.233

_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.620

# Sheldrick geometric approximatio 0.95 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.96
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2' ####
_diffrn_radiation_source         
'Supernova (Cu) X-ray Source' ################
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            30309
_reflns_number_total             7576
_diffrn_reflns_av_R_equivalents  0.034
# Number of reflections without Friedels Law is 7576 
# Number of reflections with Friedels Law is 4005 
# Theoretical number of reflections is about 3877 


_diffrn_reflns_theta_min         3.833
_diffrn_reflns_theta_max         72.389
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        72.389
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -19
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   3.13
_oxford_diffrn_Wilson_scale      0.01

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

_refine_diff_density_min         -0.14
_refine_diff_density_max         0.12


# 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>-10.0\s(I)
_refine_ls_number_reflns         7576
_refine_ls_number_restraints     23
_refine_ls_number_parameters     501
_oxford_refine_ls_R_factor_ref   0.0324
_refine_ls_wR_factor_ref         0.0820
_refine_ls_goodness_of_fit_ref   1.0042
_refine_ls_shift/su_max          0.0081346
_refine_ls_shift/su_mean         0.0002778


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7576
_refine_ls_R_factor_all          0.0324
_refine_ls_wR_factor_all         0.0820

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7384
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_gt          0.0811

_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_abs_structure_details 'Flack (1983), 3571 Friedel-pairs'
# 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 ad


_refine_ls_structure_factor_coef Fsqd
_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= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.26P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               
One of the C₂₃H₂₄N₂O₂ molecules
shows disorder in the packing of its ---C₃H₅ group.
Alternative sites were found for C51, C55, C56 and C57.
These alternative sites were refined with isotropic displacement parameters
set equal to Ueq of the corresponding atom site from the major orientation.
Restraints were applied to distances and angles within the disorder
to match values obtained from molecule one.
The relative occupancies of disordered sites were refined.


 The compound is enantiomerically pure.
Its absolute configuration  has been determined 
by refinement of the Flack parameter.
The final value of the Flack parameter is 0.05(12) and 
the final value of the Hooft parameter is 0.07(5).

The H atoms 
away from the disorder were located in a difference map, but 
were repositioned geometrically. 
These H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å, N---H = 0.87Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which they  were refined with riding
constraints.
The H atoms within the disordered were included at calculated
positions and ride on the atom sites to which they are respectively bonded.


The peaks in the final difference electron density map 
are all small, with the largest being within methyl groups,
probably suggesting 
some rotational disorder of the H atoms.

;

# 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 0.05681(15) 0.60818(8) 0.75621(6) 0.0409 1.0000 Uani . . . . . .
O2 O 0.09373(11) 0.69377(6) 0.52154(5) 0.0258 1.0000 Uani . . . . . .
O51 O 0.55791(16) 0.41572(8) 0.26604(6) 0.0447 1.0000 Uani . . . . . .
O52 O 0.52642(14) 0.33695(7) 0.01995(6) 0.0337 1.0000 Uani . . . . . .
N1 N 0.26100(15) 0.57888(8) 0.65932(7) 0.0291 1.0000 Uani . . . . . .
N2 N 0.40671(19) 0.49584(9) 0.40381(7) 0.0417 1.0000 Uani . . . . . .
N51 N 0.36674(18) 0.45058(9) 0.15901(7) 0.0397 1.0000 Uani D . . . . .
N52 N 0.21351(19) 0.53170(10) -0.10386(8) 0.0445 1.0000 Uani . . . . . .
C1 C 0.35193(16) 0.61860(9) 0.59055(7) 0.0260 1.0000 Uani . . . . . .
C2 C 0.24000(16) 0.70113(8) 0.57996(7) 0.0248 1.0000 Uani . . . . . .
C3 C 0.15316(17) 0.71391(9) 0.66150(7) 0.0264 1.0000 Uani . . . . . .
C4 C 0.14798(17) 0.62868(9) 0.69848(7) 0.0288 1.0000 Uani . . . . . .
C5 C 0.55137(18) 0.63312(10) 0.61436(8) 0.0342 1.0000 Uani . . . . . .
C6 C 0.62180(19) 0.70996(12) 0.65754(9) 0.0407 1.0000 Uani . . . . . .
C7 C 0.66497(19) 0.69429(13) 0.57084(9) 0.0445 1.0000 Uani . . . . . .
C8 C 0.33653(18) 0.56237(9) 0.51764(8) 0.0292 1.0000 Uani . . . . . .
C9 C 0.18118(19) 0.51392(9) 0.49020(8) 0.0317 1.0000 Uani . . . . . .
C10 C 0.0060(2) 0.50101(9) 0.51768(10) 0.0369 1.0000 Uani . . . . . .
C11 C -0.1124(2) 0.45072(10) 0.47262(12) 0.0466 1.0000 Uani . . . . . .
C12 C -0.0618(3) 0.41404(10) 0.40014(13) 0.0536 1.0000 Uani . . . . . .
C13 C 0.1103(3) 0.42353(11) 0.37277(11) 0.0491 1.0000 Uani . . . . . .
C14 C 0.2322(2) 0.47366(10) 0.41870(9) 0.0383 1.0000 Uani . . . . . .
C15 C 0.46912(19) 0.54917(10) 0.46345(8) 0.0349 1.0000 Uani . . . . . .
C16 C 0.13221(19) 0.72099(10) 0.44172(8) 0.0330 1.0000 Uani . . . . . .
C17 C -0.04256(19) 0.71428(9) 0.39128(7) 0.0321 1.0000 Uani . . . . . .
C18 C -0.1716(2) 0.77767(10) 0.39314(9) 0.0370 1.0000 Uani . . . . . .
C19 C -0.3349(2) 0.77064(11) 0.34838(11) 0.0457 1.0000 Uani . . . . . .
C20 C -0.3695(2) 0.70085(12) 0.30122(11) 0.0502 1.0000 Uani . . . . . .
C21 C -0.2425(3) 0.63748(12) 0.29962(11) 0.0510 1.0000 Uani . . . . . .
C22 C -0.0795(2) 0.64453(11) 0.34459(9) 0.0418 1.0000 Uani . . . . . .
C23 C 0.2985(2) 0.49371(10) 0.68415(9) 0.0414 1.0000 Uani . . . . . .
C51 C 0.2811(4) 0.4137(3) 0.0860(2) 0.0352 0.678(3) Uani D . P . . .
C52 C 0.38748(18) 0.33051(10) 0.07671(8) 0.0326 1.0000 Uani D . . . . .
C53 C 0.48148(18) 0.31640(10) 0.15946(8) 0.0321 1.0000 Uani . . . . . .
C54 C 0.47575(18) 0.39856(10) 0.20161(8) 0.0333 1.0000 Uani . . . . . .
C55 C 0.0799(3) 0.40660(16) 0.10803(12) 0.0314 0.678(3) Uani D . P . . .
C56 C 0.0122(6) 0.3347(2) 0.1577(2) 0.0397 0.678(3) Uani D . P . . .
C57 C -0.0403(3) 0.34237(19) 0.06812(14) 0.0474 0.678(3) Uani D . P . . .
C58 C 0.28750(19) 0.47014(10) 0.01470(8) 0.0357 1.0000 Uani D . . . . .
C59 C 0.4425(2) 0.51702(10) -0.01012(9) 0.0348 1.0000 Uani . . . . . .
C60 C 0.6182(2) 0.53163(11) 0.02185(10) 0.0413 1.0000 Uani . . . . . .
C61 C 0.7365(2) 0.57904(11) -0.02172(12) 0.0480 1.0000 Uani . . . . . .
C62 C 0.6835(3) 0.61194(11) -0.09793(12) 0.0515 1.0000 Uani . . . . . .
C63 C 0.5101(3) 0.60071(11) -0.13023(11) 0.0472 1.0000 Uani . . . . . .
C64 C 0.3894(2) 0.55402(10) -0.08537(9) 0.0393 1.0000 Uani . . . . . .
C65 C 0.1533(2) 0.48144(11) -0.04414(9) 0.0394 1.0000 Uani . . . . . .
C66 C 0.4747(3) 0.30844(13) -0.05961(10) 0.0509 1.0000 Uani . . . . . .
C67 C 0.6436(3) 0.30835(12) -0.10730(10) 0.0491 1.0000 Uani . . . . . .
C68 C 0.6849(3) 0.37462(15) -0.15593(11) 0.0594 1.0000 Uani . . . . . .
C69 C 0.8433(4) 0.37537(19) -0.19910(13) 0.0757 1.0000 Uani . . . . . .
C70 C 0.9625(4) 0.3091(2) -0.19204(14) 0.0773 1.0000 Uani . . . . . .
C71 C 0.9251(4) 0.24391(19) -0.14303(18) 0.0874 1.0000 Uani . . . . . .
C72 C 0.7670(4) 0.24276(15) -0.10115(15) 0.0750 1.0000 Uani . . . . . .
C73 C 0.3274(3) 0.53422(13) 0.18573(11) 0.0532 1.0000 Uani . . . . . .
C151 C 0.2642(9) 0.4110(4) 0.0865(5) 0.0350 0.322(3) Uiso D . P . . .
C155 C 0.0775(6) 0.3666(3) 0.0880(3) 0.0320 0.322(3) Uiso D . P . . .
C156 C 0.0246(19) 0.3151(6) 0.1588(7) 0.0400 0.322(3) Uiso D . P . . .
C157 C -0.0608(7) 0.3992(3) 0.1437(3) 0.0480 0.322(3) Uiso D . P . . .
H1 H 0.4703 0.4759 0.3658 0.0504 1.0000 Uiso R . . . . .
H2 H 0.1464 0.5480 -0.1455 0.0541 1.0000 Uiso R . . . . .
H21 H 0.3184 0.7478 0.5660 0.0273 1.0000 Uiso R . . . . .
H31 H 0.2225 0.7499 0.6970 0.0306 1.0000 Uiso R . . . . .
H32 H 0.0356 0.7389 0.6548 0.0306 1.0000 Uiso R . . . . .
H51 H 0.6194 0.5823 0.6300 0.0405 1.0000 Uiso R . . . . .
H61 H 0.7129 0.7017 0.6990 0.0481 1.0000 Uiso R . . . . .
H62 H 0.5409 0.7549 0.6687 0.0473 1.0000 Uiso R . . . . .
H71 H 0.7868 0.6783 0.5600 0.0524 1.0000 Uiso R . . . . .
H72 H 0.6081 0.7320 0.5295 0.0528 1.0000 Uiso R . . . . .
H101 H -0.0314 0.5257 0.5664 0.0432 1.0000 Uiso R . . . . .
H111 H -0.2303 0.4411 0.4911 0.0538 1.0000 Uiso R . . . . .
H121 H -0.1463 0.3817 0.3695 0.0623 1.0000 Uiso R . . . . .
H131 H 0.1424 0.3990 0.3225 0.0589 1.0000 Uiso R . . . . .
H151 H 0.5862 0.5721 0.4657 0.0420 1.0000 Uiso R . . . . .
H161 H 0.1754 0.7809 0.4433 0.0395 1.0000 Uiso R . . . . .
H162 H 0.2311 0.6868 0.4178 0.0401 1.0000 Uiso R . . . . .
H181 H -0.1510 0.8252 0.4256 0.0424 1.0000 Uiso R . . . . .
H191 H -0.4218 0.8140 0.3511 0.0538 1.0000 Uiso R . . . . .
H201 H -0.4780 0.6940 0.2717 0.0590 1.0000 Uiso R . . . . .
H211 H -0.2672 0.5900 0.2700 0.0599 1.0000 Uiso R . . . . .
H221 H 0.0058 0.6023 0.3442 0.0496 1.0000 Uiso R . . . . .
H231 H 0.2078 0.4740 0.7206 0.0630 1.0000 Uiso R . . . . .
H232 H 0.4155 0.4912 0.7130 0.0619 1.0000 Uiso R . . . . .
H233 H 0.3050 0.4570 0.6399 0.0618 1.0000 Uiso R . . . . .
H521 H 0.3062 0.2835 0.0627 0.0387 1.0000 Uiso R . . . . .
H531 H 0.6060 0.2970 0.1547 0.0386 1.0000 Uiso R . . . . .
H532 H 0.4164 0.2753 0.1888 0.0382 1.0000 Uiso R . . . . .
H601 H 0.6592 0.5082 0.0710 0.0466 1.0000 Uiso R . . . . .
H611 H 0.8564 0.5894 -0.0002 0.0567 1.0000 Uiso R . . . . .
H621 H 0.7671 0.6431 -0.1262 0.0599 1.0000 Uiso R . . . . .
H631 H 0.4729 0.6240 -0.1808 0.0570 1.0000 Uiso R . . . . .
H651 H 0.0337 0.4612 -0.0432 0.0451 1.0000 Uiso R . . . . .
H661 H 0.3759 0.3442 -0.0853 0.0619 1.0000 Uiso R . . . . .
H662 H 0.4309 0.2490 -0.0554 0.0610 1.0000 Uiso R . . . . .
H681 H 0.6064 0.4196 -0.1609 0.0678 1.0000 Uiso R . . . . .
H691 H 0.8653 0.4201 -0.2321 0.0897 1.0000 Uiso R . . . . .
H701 H 1.0698 0.3099 -0.2209 0.0921 1.0000 Uiso R . . . . .
H711 H 1.0099 0.1998 -0.1375 0.1027 1.0000 Uiso R . . . . .
H721 H 0.7412 0.1971 -0.0674 0.0868 1.0000 Uiso R . . . . .
H731 H 0.3983 0.5495 0.2334 0.0786 1.0000 Uiso R . . . . .
H732 H 0.3456 0.5740 0.1460 0.0789 1.0000 Uiso R . . . . .
H733 H 0.2028 0.5376 0.1988 0.0791 1.0000 Uiso R . . . . .
H551 H 0.0220 0.4582 0.1177 0.0377 0.6780 Uiso R . . . . .
H561 H -0.0759 0.3439 0.1970 0.0476 0.6780 Uiso R . . . . .
H562 H 0.0940 0.2924 0.1761 0.0476 0.6780 Uiso R . . . . .
H571 H -0.1617 0.3561 0.0515 0.0570 0.6780 Uiso R . . . . .
H572 H 0.0082 0.3046 0.0305 0.0570 0.6780 Uiso R . . . . .
H1551 H 0.0299 0.3481 0.0369 0.0384 0.3220 Uiso R . . . . .
H1561 H 0.1081 0.3071 0.2034 0.0480 0.3220 Uiso R . . . . .
H1562 H -0.0455 0.2661 0.1502 0.0480 0.3220 Uiso R . . . . .
H1571 H -0.0312 0.4442 0.1789 0.0576 0.3220 Uiso R . . . . .
H1572 H -0.1848 0.4032 0.1258 0.0576 0.3220 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.15(14)
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 . C4 . 1.2353(17) yes
O2 . C2 . 1.4221(14) yes
O2 . C16 . 1.4317(15) yes
O51 . C54 . 1.2355(18) yes
O52 . C52 . 1.4210(16) yes
O52 . C66 . 1.4314(18) yes
N1 . C1 . 1.4886(16) yes
N1 . C4 . 1.3412(18) yes
N1 . C23 . 1.4539(18) yes
N2 . C14 . 1.365(2) yes
N2 . C15 . 1.3728(19) yes
N2 . H1 . 0.861 no
N51 . C51 . 1.465(4) yes
N51 . C54 . 1.3397(19) yes
N51 . C73 . 1.450(2) yes
N51 . C151 . 1.531(7) yes
N52 . C64 . 1.366(2) yes
N52 . C65 . 1.365(2) yes
N52 . H2 . 0.871 no
C1 . C2 . 1.5686(17) yes
C1 . C5 . 1.5222(17) yes
C1 . C8 . 1.5091(17) yes
C2 . C3 . 1.5313(16) yes
C2 . H21 . 0.981 no
C3 . C4 . 1.5028(18) yes
C3 . H31 . 0.958 no
C3 . H32 . 0.956 no
C5 . C6 . 1.509(2) yes
C5 . C7 . 1.496(2) yes
C5 . H51 . 0.988 no
C6 . C7 . 1.504(2) yes
C6 . H61 . 0.949 no
C6 . H62 . 0.960 no
C7 . H71 . 0.957 no
C7 . H72 . 0.994 no
C8 . C9 . 1.4416(19) yes
C8 . C15 . 1.369(2) yes
C9 . C10 . 1.401(2) yes
C9 . C14 . 1.414(2) yes
C10 . C11 . 1.384(2) yes
C10 . H101 . 0.950 no
C11 . C12 . 1.401(3) yes
C11 . H111 . 0.945 no
C12 . C13 . 1.371(3) yes
C12 . H121 . 0.943 no
C13 . C14 . 1.406(2) yes
C13 . H131 . 0.960 no
C15 . H151 . 0.937 no
C16 . C17 . 1.5082(18) yes
C16 . H161 . 1.015 no
C16 . H162 . 1.007 no
C17 . C18 . 1.395(2) yes
C17 . C22 . 1.383(2) yes
C18 . C19 . 1.390(2) yes
C18 . H181 . 0.944 no
C19 . C20 . 1.385(3) yes
C19 . H191 . 0.949 no
C20 . C21 . 1.384(3) yes
C20 . H201 . 0.925 no
C21 . C22 . 1.390(2) yes
C21 . H211 . 0.922 no
C22 . H221 . 0.925 no
C23 . H231 . 0.971 no
C23 . H232 . 0.968 no
C23 . H233 . 0.944 no
C51 . C52 . 1.562(5) yes
C51 . C55 . 1.543(3) yes
C51 . C58 . 1.491(4) yes
C52 . C53 . 1.5261(17) yes
C52 . C151 . 1.593(8) yes
C52 . H521 . 0.986 no
C53 . C54 . 1.496(2) yes
C53 . H531 . 0.974 no
C53 . H532 . 0.960 no
C55 . C56 . 1.516(3) yes
C55 . C57 . 1.497(3) yes
C55 . H551 . 0.950 no
C56 . C57 . 1.522(5) yes
C56 . H561 . 0.950 no
C56 . H562 . 0.950 no
C57 . H571 . 0.950 no
C57 . H572 . 0.950 no
C58 . C59 . 1.441(2) yes
C58 . C65 . 1.370(2) yes
C58 . C151 . 1.537(7) yes
C59 . C60 . 1.397(2) yes
C59 . C64 . 1.421(2) yes
C60 . C61 . 1.383(2) yes
C60 . H601 . 0.936 no
C61 . C62 . 1.408(3) yes
C61 . H611 . 0.953 no
C62 . C63 . 1.375(3) yes
C62 . H621 . 0.935 no
C63 . C64 . 1.400(2) yes
C63 . H631 . 0.947 no
C65 . H651 . 0.939 no
C66 . C67 . 1.500(3) yes
C66 . H661 . 1.007 no
C66 . H662 . 1.012 no
C67 . C68 . 1.378(3) yes
C67 . C72 . 1.393(3) yes
C68 . C69 . 1.392(3) yes
C68 . H681 . 0.927 no
C69 . C70 . 1.382(4) yes
C69 . H691 . 0.923 no
C70 . C71 . 1.361(4) yes
C70 . H701 . 0.940 no
C71 . C72 . 1.379(4) yes
C71 . H711 . 0.947 no
C72 . H721 . 0.947 no
C73 . H731 . 0.960 no
C73 . H732 . 0.932 no
C73 . H733 . 0.952 no
C151 . C155 . 1.550(6) yes
C155 . C156 . 1.499(8) yes
C155 . C157 . 1.496(6) yes
C155 . H1551 . 0.950 no
C156 . C157 . 1.508(7) yes
C156 . H1561 . 0.950 no
C156 . H1562 . 0.950 no
C157 . H1571 . 0.950 no
C157 . H1572 . 0.950 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 . O2 . C16 . 115.42(9) yes
C52 . O52 . C66 . 114.47(12) yes
C1 . N1 . C4 . 114.88(11) yes
C1 . N1 . C23 . 122.33(11) yes
C4 . N1 . C23 . 122.74(12) yes
C14 . N2 . C15 . 108.83(12) yes
C14 . N2 . H1 . 125.3 no
C15 . N2 . H1 . 125.6 no
C51 . N51 . C54 . 114.17(19) yes
C51 . N51 . C73 . 122.9(2) yes
C54 . N51 . C73 . 122.84(14) yes
C54 . N51 . C151 . 114.7(3) yes
C73 . N51 . C151 . 121.8(3) yes
C64 . N52 . C65 . 109.06(13) yes
C64 . N52 . H2 . 126.8 no
C65 . N52 . H2 . 124.1 no
N1 . C1 . C2 . 101.43(9) yes
N1 . C1 . C5 . 109.09(10) yes
C2 . C1 . C5 . 113.29(11) yes
N1 . C1 . C8 . 109.46(11) yes
C2 . C1 . C8 . 113.35(10) yes
C5 . C1 . C8 . 109.81(10) yes
C1 . C2 . O2 . 112.63(10) yes
C1 . C2 . C3 . 104.57(10) yes
O2 . C2 . C3 . 106.19(9) yes
C1 . C2 . H21 . 111.3 no
O2 . C2 . H21 . 109.8 no
C3 . C2 . H21 . 112.1 no
C2 . C3 . C4 . 104.79(10) yes
C2 . C3 . H31 . 113.0 no
C4 . C3 . H31 . 108.9 no
C2 . C3 . H32 . 111.3 no
C4 . C3 . H32 . 113.1 no
H31 . C3 . H32 . 105.8 no
C3 . C4 . N1 . 108.75(11) yes
C3 . C4 . O1 . 125.64(12) yes
N1 . C4 . O1 . 125.60(13) yes
C1 . C5 . C6 . 123.86(12) yes
C1 . C5 . C7 . 121.91(12) yes
C6 . C5 . C7 . 60.09(10) yes
C1 . C5 . H51 . 114.4 no
C6 . C5 . H51 . 113.2 no
C7 . C5 . H51 . 112.6 no
C5 . C6 . C7 . 59.51(10) yes
C5 . C6 . H61 . 116.5 no
C7 . C6 . H61 . 119.7 no
C5 . C6 . H62 . 120.3 no
C7 . C6 . H62 . 117.9 no
H61 . C6 . H62 . 113.1 no
C6 . C7 . C5 . 60.41(10) yes
C6 . C7 . H71 . 117.4 no
C5 . C7 . H71 . 117.4 no
C6 . C7 . H72 . 117.1 no
C5 . C7 . H72 . 120.4 no
H71 . C7 . H72 . 114.0 no
C1 . C8 . C9 . 127.49(12) yes
C1 . C8 . C15 . 125.81(13) yes
C9 . C8 . C15 . 106.69(12) yes
C8 . C9 . C10 . 134.96(13) yes
C8 . C9 . C14 . 106.08(13) yes
C10 . C9 . C14 . 118.95(13) yes
C9 . C10 . C11 . 118.61(15) yes
C9 . C10 . H101 . 121.1 no
C11 . C10 . H101 . 120.3 no
C10 . C11 . C12 . 121.60(17) yes
C10 . C11 . H111 . 119.1 no
C12 . C11 . H111 . 119.3 no
C11 . C12 . C13 . 121.20(14) yes
C11 . C12 . H121 . 120.0 no
C13 . C12 . H121 . 118.8 no
C12 . C13 . C14 . 117.54(16) yes
C12 . C13 . H131 . 120.3 no
C14 . C13 . H131 . 122.1 no
C9 . C14 . C13 . 122.01(16) yes
C9 . C14 . N2 . 108.41(13) yes
C13 . C14 . N2 . 129.51(15) yes
N2 . C15 . C8 . 109.99(13) yes
N2 . C15 . H151 . 123.7 no
C8 . C15 . H151 . 126.3 no
O2 . C16 . C17 . 107.00(10) yes
O2 . C16 . H161 . 109.9 no
C17 . C16 . H161 . 110.0 no
O2 . C16 . H162 . 111.7 no
C17 . C16 . H162 . 110.9 no
H161 . C16 . H162 . 107.4 no
C16 . C17 . C18 . 120.09(13) yes
C16 . C17 . C22 . 120.73(14) yes
C18 . C17 . C22 . 119.15(13) yes
C17 . C18 . C19 . 120.22(15) yes
C17 . C18 . H181 . 120.8 no
C19 . C18 . H181 . 119.0 no
C18 . C19 . C20 . 120.08(16) yes
C18 . C19 . H191 . 119.0 no
C20 . C19 . H191 . 120.9 no
C19 . C20 . C21 . 119.94(15) yes
C19 . C20 . H201 . 121.9 no
C21 . C20 . H201 . 118.1 no
C20 . C21 . C22 . 119.88(16) yes
C20 . C21 . H211 . 120.2 no
C22 . C21 . H211 . 119.9 no
C21 . C22 . C17 . 120.72(16) yes
C21 . C22 . H221 . 120.5 no
C17 . C22 . H221 . 118.8 no
N1 . C23 . H231 . 110.8 no
N1 . C23 . H232 . 109.5 no
H231 . C23 . H232 . 107.4 no
N1 . C23 . H233 . 112.7 no
H231 . C23 . H233 . 109.6 no
H232 . C23 . H233 . 106.5 no
N51 . C51 . C52 . 103.2(2) yes
N51 . C51 . C55 . 102.7(2) yes
C52 . C51 . C55 . 116.7(3) yes
N51 . C51 . C58 . 112.3(3) yes
C52 . C51 . C58 . 114.3(2) yes
C55 . C51 . C58 . 107.1(2) yes
C51 . C52 . O52 . 112.35(15) yes
C51 . C52 . C53 . 104.45(16) yes
O52 . C52 . C53 . 107.02(11) yes
O52 . C52 . C151 . 115.9(3) yes
C53 . C52 . C151 . 105.6(3) yes
C51 . C52 . H521 . 112.3 no
O52 . C52 . H521 . 110.2 no
C53 . C52 . H521 . 110.2 no
C151 . C52 . H521 . 107.8 no
C52 . C53 . C54 . 105.48(11) yes
C52 . C53 . H531 . 111.6 no
C54 . C53 . H531 . 111.4 no
C52 . C53 . H532 . 109.8 no
C54 . C53 . H532 . 110.4 no
H531 . C53 . H532 . 108.1 no
C53 . C54 . N51 . 109.53(12) yes
C53 . C54 . O51 . 125.31(13) yes
N51 . C54 . O51 . 125.17(15) yes
C51 . C55 . C56 . 121.7(3) yes
C51 . C55 . C57 . 120.2(2) yes
C56 . C55 . C57 . 60.7(2) yes
C51 . C55 . H551 . 114.6 no
C56 . C55 . H551 . 114.6 no
C57 . C55 . H551 . 114.6 no
C55 . C56 . C57 . 59.04(17) yes
C55 . C56 . H561 . 120.2 no
C57 . C56 . H561 . 120.2 no
C55 . C56 . H562 . 120.2 no
C57 . C56 . H562 . 120.2 no
H561 . C56 . H562 . 109.5 no
C56 . C57 . C55 . 60.28(18) yes
C56 . C57 . H571 . 120.0 no
C55 . C57 . H571 . 120.0 no
C56 . C57 . H572 . 119.9 no
C55 . C57 . H572 . 120.0 no
C51 . C58 . C59 . 126.56(16) yes
C51 . C58 . C65 . 126.72(17) yes
C59 . C58 . C65 . 106.46(13) yes
C59 . C58 . C151 . 131.2(3) yes
C65 . C58 . C151 . 122.1(3) yes
C58 . C59 . C60 . 135.33(14) yes
C58 . C59 . C64 . 106.10(13) yes
C60 . C59 . C64 . 118.57(14) yes
C59 . C60 . C61 . 119.22(15) yes
C59 . C60 . H601 . 121.5 no
C61 . C60 . H601 . 119.2 no
C60 . C61 . C62 . 121.18(17) yes
C60 . C61 . H611 . 119.7 no
C62 . C61 . H611 . 119.1 no
C61 . C62 . C63 . 121.14(16) yes
C61 . C62 . H621 . 119.1 no
C63 . C62 . H621 . 119.7 no
C62 . C63 . C64 . 117.60(16) yes
C62 . C63 . H631 . 121.4 no
C64 . C63 . H631 . 121.0 no
C59 . C64 . C63 . 122.19(16) yes
C59 . C64 . N52 . 108.05(14) yes
C63 . C64 . N52 . 129.68(15) yes
C58 . C65 . N52 . 110.33(14) yes
C58 . C65 . H651 . 126.2 no
N52 . C65 . H651 . 123.3 no
O52 . C66 . C67 . 106.88(14) yes
O52 . C66 . H661 . 111.4 no
C67 . C66 . H661 . 112.2 no
O52 . C66 . H662 . 108.2 no
C67 . C66 . H662 . 108.0 no
H661 . C66 . H662 . 109.9 no
C66 . C67 . C68 . 120.98(19) yes
C66 . C67 . C72 . 120.95(19) yes
C68 . C67 . C72 . 118.0(2) yes
C67 . C68 . C69 . 121.1(2) yes
C67 . C68 . H681 . 120.2 no
C69 . C68 . H681 . 118.7 no
C68 . C69 . C70 . 119.5(2) yes
C68 . C69 . H691 . 118.8 no
C70 . C69 . H691 . 121.7 no
C69 . C70 . C71 . 120.1(2) yes
C69 . C70 . H701 . 119.4 no
C71 . C70 . H701 . 120.5 no
C70 . C71 . C72 . 120.4(3) yes
C70 . C71 . H711 . 119.1 no
C72 . C71 . H711 . 120.5 no
C67 . C72 . C71 . 120.9(2) yes
C67 . C72 . H721 . 119.0 no
C71 . C72 . H721 . 120.1 no
N51 . C73 . H731 . 112.3 no
N51 . C73 . H732 . 112.8 no
H731 . C73 . H732 . 108.4 no
N51 . C73 . H733 . 109.2 no
H731 . C73 . H733 . 107.1 no
H732 . C73 . H733 . 106.8 no
C58 . C151 . N51 . 106.4(4) yes
C58 . C151 . C52 . 110.0(5) yes
N51 . C151 . C52 . 98.8(4) yes
C58 . C151 . C155 . 115.2(5) yes
N51 . C151 . C155 . 126.0(6) yes
C52 . C151 . C155 . 97.8(4) yes
C151 . C155 . C156 . 121.8(7) yes
C151 . C155 . C157 . 118.4(5) yes
C156 . C155 . C157 . 60.5(4) yes
C151 . C155 . H1551 . 115.1 no
C156 . C155 . H1551 . 115.1 no
C157 . C155 . H1551 . 115.1 no
C155 . C156 . C157 . 59.7(4) yes
C155 . C156 . H1561 . 120.1 no
C157 . C156 . H1561 . 120.1 no
C155 . C156 . H1562 . 120.0 no
C157 . C156 . H1562 . 120.0 no
H1561 . C156 . H1562 . 109.5 no
C156 . C157 . C155 . 59.9(4) yes
C156 . C157 . H1571 . 120.0 no
C155 . C157 . H1571 . 120.0 no
C156 . C157 . H1572 . 120.1 no
C155 . C157 . H1572 . 120.0 no
H1571 . C157 . H1572 . 109.5 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
N2 . H1 . O51 . 165 0.86 2.04 2.883(3) yes
N52 . H2 . O1 1_554 163 0.87 1.98 2.827(3) yes


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 O52 C52 C51 -96.32(19) . . . . no
C66 O52 C52 C53 149.60(14) . . . . no
C52 O52 C66 C67 -172.03(14) . . . . no
C2 O2 C16 C17 -175.74(11) . . . . no
C16 O2 C2 C1 -95.09(13) . . . . no
C16 O2 C2 C3 151.03(11) . . . . no
C54 N51 C51 C52 -12.1(3) . . . . no
C73 N51 C51 C55 -66.4(3) . . . . no
C73 N51 C51 C58 48.3(3) . . . . no
C51 N51 C54 O51 -178.08(18) . . . . no
C51 N51 C54 C53 1.5(2) . . . . no
C73 N51 C54 O51 -2.1(2) . . . . no
C73 N51 C54 C53 177.53(14) . . . . no
C73 N51 C51 C52 171.88(16) . . . . no
C54 N51 C51 C55 109.6(2) . . . . no
C54 N51 C51 C58 -135.7(2) . . . . no
C65 N52 C64 C59 -0.67(19) . . . . no
C65 N52 C64 C63 176.04(17) . . . . no
C64 N52 C65 C58 0.31(19) . . . . no
C23 N1 C4 O1 -3.9(2) . . . . no
C23 N1 C1 C2 170.22(11) . . . . no
C4 N1 C1 C5 107.39(13) . . . . no
C4 N1 C1 C8 -132.43(12) . . . . no
C23 N1 C4 C3 175.13(11) . . . . no
C4 N1 C1 C2 -12.40(13) . . . . no
C23 N1 C1 C5 -69.99(16) . . . . no
C23 N1 C1 C8 50.19(15) . . . . no
C1 N1 C4 O1 178.78(12) . . . . no
C1 N1 C4 C3 -2.23(15) . . . . no
C14 N2 C15 C8 -0.05(18) . . . . no
C15 N2 C14 C13 176.87(17) . . . . no
C15 N2 C14 C9 -0.10(17) . . . . no
C58 C51 C52 O52 23.8(3) . . . . no
C55 C51 C58 C65 -29.3(4) . . . . no
N51 C51 C52 C53 17.2(2) . . . . no
C55 C51 C52 O52 149.83(19) . . . . no
C58 C51 C52 C53 139.4(2) . . . . no
N51 C51 C55 C56 -82.1(3) . . . . no
N51 C51 C55 C57 -154.3(2) . . . . no
C52 C51 C55 C56 29.9(4) . . . . no
C52 C51 C55 C57 -42.3(3) . . . . no
C58 C51 C55 C56 159.4(2) . . . . no
C58 C51 C55 C57 87.3(3) . . . . no
N51 C51 C58 C59 45.5(3) . . . . no
N51 C51 C58 C65 -141.26(19) . . . . no
C52 C51 C58 C59 -71.7(3) . . . . no
C52 C51 C58 C65 101.6(2) . . . . no
C55 C51 C58 C59 157.43(19) . . . . no
N51 C51 C52 O52 -98.5(2) . . . . no
C55 C51 C52 C53 -94.5(2) . . . . no
O52 C52 C53 C54 102.59(13) . . . . no
C51 C52 C53 C54 -16.71(18) . . . . no
C52 C53 C54 O51 -170.28(13) . . . . no
C52 C53 C54 N51 10.14(15) . . . . no
C51 C55 C56 C57 -109.3(3) . . . . no
C51 C55 C57 C56 111.7(3) . . . . no
C51 C58 C59 C60 -5.8(4) . . . . no
C51 C58 C59 C64 173.8(2) . . . . no
C65 C58 C59 C60 179.78(19) . . . . no
C65 C58 C59 C64 -0.56(17) . . . . no
C51 C58 C65 N52 -174.2(2) . . . . no
C59 C58 C65 N52 0.17(19) . . . . no
C58 C59 C60 C61 177.46(18) . . . . no
C64 C59 C60 C61 -2.2(2) . . . . no
C58 C59 C64 N52 0.75(18) . . . . no
C58 C59 C64 C63 -176.25(15) . . . . no
C60 C59 C64 N52 -179.52(15) . . . . no
C60 C59 C64 C63 3.5(2) . . . . no
C59 C60 C61 C62 -0.7(3) . . . . no
C60 C61 C62 C63 2.5(3) . . . . no
C61 C62 C63 C64 -1.3(3) . . . . no
C62 C63 C64 N52 -178.03(17) . . . . no
C62 C63 C64 C59 -1.7(3) . . . . no
O52 C66 C67 C72 81.5(2) . . . . no
O52 C66 C67 C68 -95.9(2) . . . . no
C66 C67 C68 C69 178.8(2) . . . . no
C66 C67 C72 C71 -177.9(2) . . . . no
C68 C67 C72 C71 -0.5(3) . . . . no
C72 C67 C68 C69 1.4(3) . . . . no
C67 C68 C69 C70 -1.0(3) . . . . no
C68 C69 C70 C71 -0.2(4) . . . . no
C69 C70 C71 C72 1.1(4) . . . . no
C70 C71 C72 C67 -0.7(4) . . . . no
N1 C1 C2 O2 -93.58(11) . . . . no
N1 C1 C2 C3 21.29(12) . . . . no
C5 C1 C2 O2 149.65(10) . . . . no
C5 C1 C2 C3 -95.48(12) . . . . no
C8 C1 C2 O2 23.65(14) . . . . no
C8 C1 C2 C3 138.53(11) . . . . no
N1 C1 C5 C6 -87.34(16) . . . . no
N1 C1 C5 C7 -160.50(14) . . . . no
C2 C1 C5 C6 24.83(17) . . . . no
C2 C1 C5 C7 -48.33(17) . . . . no
C8 C1 C5 C6 152.69(13) . . . . no
C8 C1 C5 C7 79.54(17) . . . . no
N1 C1 C8 C9 40.40(18) . . . . no
N1 C1 C8 C15 -141.08(14) . . . . no
C2 C1 C8 C9 -72.03(17) . . . . no
C2 C1 C8 C15 106.49(15) . . . . no
C5 C1 C8 C9 160.14(14) . . . . no
C5 C1 C8 C15 -21.34(19) . . . . no
O2 C2 C3 C4 96.10(11) . . . . no
C1 C2 C3 C4 -23.21(12) . . . . no
C2 C3 C4 O1 -164.60(12) . . . . no
C2 C3 C4 N1 16.41(13) . . . . no
C1 C5 C6 C7 -110.39(15) . . . . no
C1 C5 C7 C6 113.50(15) . . . . no
C1 C8 C9 C10 -0.8(3) . . . . no
C1 C8 C9 C14 178.53(14) . . . . no
C15 C8 C9 C10 -179.52(16) . . . . no
C15 C8 C9 C14 -0.22(16) . . . . no
C1 C8 C15 N2 -178.61(13) . . . . no
C9 C8 C15 N2 0.17(17) . . . . no
C8 C9 C10 C11 177.72(16) . . . . no
C14 C9 C10 C11 -1.5(2) . . . . no
C8 C9 C14 N2 0.20(17) . . . . no
C8 C9 C14 C13 -177.05(15) . . . . no
C10 C9 C14 N2 179.63(13) . . . . no
C10 C9 C14 C13 2.4(2) . . . . no
C9 C10 C11 C12 -1.1(2) . . . . no
C10 C11 C12 C13 3.0(3) . . . . no
C11 C12 C13 C14 -2.1(3) . . . . no
C12 C13 C14 N2 -177.19(17) . . . . no
C12 C13 C14 C9 -0.6(3) . . . . no
O2 C16 C17 C18 82.76(16) . . . . no
O2 C16 C17 C22 -95.34(15) . . . . no
C16 C17 C18 C19 -178.28(14) . . . . no
C22 C17 C18 C19 -0.2(2) . . . . no
C16 C17 C22 C21 178.44(14) . . . . no
C18 C17 C22 C21 0.3(2) . . . . no
C17 C18 C19 C20 -0.5(2) . . . . no
C18 C19 C20 C21 1.0(3) . . . . no
C19 C20 C21 C22 -0.8(3) . . . . no
C20 C21 C22 C17 0.2(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N52 2.8268(18) . 1_556 no
O2 C9 3.0140(17) . . no
O2 C10 3.1679(17) . . no
O2 C7 3.2922(16) . 1_455 no
O2 N1 3.1470(15) . . no
O51 N2 2.8833(17) . . no
O52 C59 3.000(2) . . no
O52 N51 3.2013(17) . . no
O52 C57 3.256(2) . 1_655 no
O52 C60 3.204(2) . . no
N1 C10 3.198(2) . . no
N51 C60 3.261(2) . . no
C3 C12 3.436(2) . 2_556 no
C3 C6 3.4533(19) . . no
C6 C53 3.589(2) . 2_656 no
C7 C15 3.237(2) . . no
C7 C18 3.492(2) . 1_655 no
C8 C16 3.193(2) . . no
C9 C23 3.307(2) . . no
C9 C16 3.442(2) . . no
C10 C23 3.428(2) . . no
C11 C15 3.461(2) . 1_455 no
C52 C62 3.575(2) . 2_645 no
C53 C156 3.362(14) . . no
C53 C56 3.466(5) . . no
C53 C63 3.505(2) . 2_645 no
C54 C157 3.581(5) . 1_655 no
C57 C72 3.479(4) . 1_455 no
C57 C65 3.273(3) . . no
C58 C66 3.213(3) . . no
C59 C66 3.465(3) . . no
C59 C73 3.397(2) . . no
C60 C73 3.525(3) . . no
C61 C65 3.480(2) . 1_655 no

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 15/03/16 at 11:56:02
#
#LIST     12                                                                    
BLOCK SCALE X'S, O(1,U'S) UNTIL C(73) 
CONT C(55,OCC) UNTIL C(57) C(51,OCC) 
CONT C(151,OCC,U[ISO]) UNTIL C(157) 
CONT ENANTIO 
EQUIV C(55,OCC) UNTIL C(57) C(51,OCC) C(151,OCC) UNTIL C(157) 
WEIGHT -1   C(151,OCC) UNTIL C(157) 
FIX C(151,U[ISO]) UNTIL C(157) 
RIDE N   (   2,X'S) H   (   1,X'S) 
RIDE N   (  52,X'S) H   (   2,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C(56,X'S) H(561,X'S) H(562,X'S) 
RIDE C   (  57,X'S) H(571,X'S) H(572,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) H   ( 662,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) 
RIDE C   (  73,X'S) H   ( 731,X'S) H   ( 732,X'S) H   ( 733,X'S) 
RIDE C   (  155,X'S) H   ( 1551,X'S) 
RIDE C(156,X'S)  H(1561,X'S) H(1562,X'S) 
RIDE C   (  157,X'S) H(1571,X'S) H(1572,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 15/03/16 at 11:56:02
#
#LIST     16                                                                    
DIST 1.52, .01 = C(51) TO C(55) 
DIST 1.52, .01 =  C(151) TO C(155) 
DIST 1.51, .01 = C(55) TO C(56), C(155) TO C(156) 
DIST 1.51, .01 = C(55) TO C(57), C(155) TO C(157) 
DIST 1.51, .01 = C(56) TO C(57), C(156) TO C(157) 
ANGLE 124, 2 = C(51) TO C(55) TO C(56), C(51) TO C(155) TO C(56) 
ANGLE 124, 2 = C(51) TO C(55) TO C(57), C(51) TO C(155) TO C(157) 
REM ANGLE 60, 2 = C(56) TO C(55) TO C(57), C(56) TO C(155) TO C(157) 
REM 
DIST 1.49, .01 = C(151) TO N(51) 
DIST 1.57, .01 = C(151) TO C(52) 
DIST 1.51, .01 = C(151) TO C(58) 
DIST 1.52, .01 = C(151) TO C(155) 
ANGLE 101, 2 = N(51) TO C(151) TO C(52) 
ANGLE 109, 2 = N(51) TO C(151) TO C(58) 
ANGLE 109, 2 = N(51) TO C(151) TO C(155) 
ANGLE 113, 2 = C(52) TO C(151) TO C(58) 
ANGLE 113, 2 = C(52) TO C(151) TO C(155) 
ANGLE 110, 2 = C(58) TO C(151) TO C(155) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


#===END

