# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_publ_contact_author_name        'Stephen G. Davies'
_publ_contact_author_address     
;Department of Chemistry
Chemical Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
_publ_contact_author_email       steve.davies@chem.ox.ac.uk

_publ_contact_author_phone       '+44 1865 275695'
_publ_contact_author_fax         '+44 1865 275633'
loop_
_publ_author_name
_publ_author_address
S.G.Davies
;Department of Chemistry
Chemical Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
R.L.Nicholson
;Department of Chemistry
Chemical Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
J.Osborne
;Department of Chemistry
Chemical Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
P.M.Roberts
;Department of Chemistry
Chemical Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
E.D.Savory
;Department of Chemistry
Chemical Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
;
A.D.Smith
;
;Department of Chemistry
Chemical Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
J.E.Thomson
;Department of Chemistry
Chemical Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
_audit_creation_date             08-12-04
_audit_creation_method           CRYSTALS_ver_12.85

_oxford_structure_analysis_title ES3
_chemical_name_systematic        ?
_chemical_melting_point          ?

#looking for refcif

# Check this file using the IUCr facility at:
# http://checkcif.iucr.org/

# The content below is held in the file 'script/refcif.dat'. This is a text
# file which you may edit to reflect local conditions.
# Items which need looking at are represented by a '?'.
# Items for which there are choices are prefixed with 'choose from'.

_publ_contact_letter             
;
Please consider this CIF submission for
publication as a Short Format Paper in
Org Biomol. Chem.
;
_publ_requested_category         EO # choose from: FI FM FO CI CM CO AD
_publ_requested_coeditor_name    'Dr Andrew D. Smith'

_publ_section_title              
# Title of paper - generally just the systematic or trivial name
;
Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements
;
loop_
_publ_author_footnote
;
? # Footnote for author 1
;
;
? # Footnote 2
;

_publ_section_abstract           
# Text of the abstract
# (a) The Abstract must be self-contained and comprehensible
# without the rest of the paper. This means no references
# to atom names or to compound numbers; compounds must be
# identified as the title compound, or by name or by some other
# means such as derivatives of each other (e.g. "the
# corresponding ketone").
# (b) The chemical formula of "the title compound" must be given.
# (c) Any crystallographic molecular symmetry should be
# mentioned, and also the presence of more than one molecule
# in the asymmetric unit (i.e. anything other than Z'=1).
;
?
;

_publ_section_related_literature 
# Not in version 2.3.1
###############################################################
# Essential references (e.g. to the origin of the material studied, related
# structural studies, and to information supporting the reported structure)
# should be cited in this section, with appropriate very brief explanatory
# text, for example `The synthesis of the complex is described by Jones
# (2001). The anhydrous complex has essentially the same coordination
# geometry (Smith, 2003).' In addition, all references included in the
# supplementary materials, but not elsewhere in the published article,
# should be given here. The simple text `For related literature, see:...'
# may be used, but further details should be provided in the Comment
# section, which forms part of the supplementary material.
###############################################################
;
?
;

_publ_section_comment            
# Text of the paper
# Note that atoms are referenced as N2, not N(2) or N~2~
# If text containing () occur within (), the outer ones should be []
# Figures should be referenced as Fig.
;
?
;
_publ_section_acknowledgements   # Acknowledgments
;
?
;
_publ_section_figure_captions    
# Captions to figures - Start each caption on a new line after a blank line
;
Fig. 1.
The title compound with displacement ellipsoids drawn at the 50%
probability level. H atoms are shown as spheres of
arbitary radius.

;
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_diffrn_radiation_probe          ?

data_1
_database_code_depnum_ccdc_archive 'CCDC 719632'

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (G\"orbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The 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--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
\%A)
and
U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# Hand-made tables can be put in the cif. The number of columns
# is set in the loop header.
# The contants of each column can either be a piece of text
# without any spaces (eg a number) or other text enclosed in " "
# Remove the leading # in the following example

#geom_extra_table_head_A
#;
#Table 2.
#Molecular parameters deviating most from MOGUL averages
#;
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
#_geom_extra_tableA_col_4
#
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d"
#N5-C6-C4 129 124 "7 (\%)"
#C3-O10-C2 105 109 "2 (\%)"
#C6-O7 1.25 1.22 ".02 (\%A)"
#
# End of 'script/refcif-b.dat'
#end of refcif
_cell_length_a                   12.3683(17)
_cell_length_b                   4.9903(8)
_cell_length_c                   12.8281(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.207(13)
_cell_angle_gamma                90
_cell_volume                     790.5(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  ?
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 0.0170 0.0090 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 57.7997
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0470 0.0320 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 0.0290 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'

_cell_formula_units_Z            2

# Given Formula = C17 H23 N1 O1
# Dc = 1.08 Fooo = 280.00 Mu = 5.11 M = 257.38
# Found Formula = C17 H23 N1 O1
# Dc = 1.08 FOOO = 280.00 Mu = 5.11 M = 257.38

_chemical_formula_sum            'C17 H23 N1 O1'
_chemical_formula_moiety         'C17 H23 N1 O1'
_chemical_compound_source        ?
_chemical_formula_weight         257.38

_cell_measurement_reflns_used    25
_cell_measurement_theta_min      21
_cell_measurement_theta_max      43
_cell_measurement_temperature    190

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_max          0.80

_exptl_crystal_density_diffrn    1.081
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.511

# Sheldrick geometric approximatio 0.82 0.82
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8151
_exptl_absorpt_correction_T_max  0.8151
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_device_type  Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       \w/2\q

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'CAD4 EXPRESS, (Straver, 1992)'
_computing_cell_refinement       'CAD4 EXPRESS, (Straver, 1992)'
_computing_data_reduction        'RC93 (Watkin et al., 1994)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  600
_diffrn_standards_interval_count .
_diffrn_standards_number         3
_diffrn_standards_decay_%        2.87

_diffrn_ambient_temperature      190
_diffrn_reflns_number            1796
_reflns_number_total             1796
_diffrn_reflns_av_R_equivalents  0.026
# Number of reflections with Friedels Law is 1796
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1606

_diffrn_reflns_theta_min         3.451
_diffrn_reflns_theta_max         74.060
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        74.060
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -15
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.32
_refine_diff_density_max         0.36

# 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>3.0\s(I)
_refine_ls_number_reflns         1692
_refine_ls_number_restraints     1
_refine_ls_number_parameters     242
_oxford_refine_ls_R_factor_ref   0.0508
_refine_ls_wR_factor_ref         0.0557
_refine_ls_goodness_of_fit_ref   1.0335
_refine_ls_shift/su_max          0.000772

# The values computed from all data
_oxford_reflns_number_all        1796
_refine_ls_R_factor_all          0.0533
_refine_ls_wR_factor_all         0.0611

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1706
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_gt          0.0559

# 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    refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
5.24 3.84 4.28
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Straver, L. H. (1992). CAD4-EXPRESS, Nonius, Delft, The Netherlands.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Watkin, D.J., Prout, C.K. & Lilley, P.M.deQ. (1994). RC93, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.71412(12) 0.6496(5) 0.77541(10) 0.0500 1.0000 Uani . . . . 3 . .
C2 C 0.71387(13) 0.4081(5) 0.75325(13) 0.0378 1.0000 Uani . . . . 3 . .
N3 N 0.75289(12) 0.2204(5) 0.81939(11) 0.0401 1.0000 Uani . . . . 3 . .
C4 C 0.80501(13) 0.2859(5) 0.92149(13) 0.0391 1.0000 Uani . . . . 3 . .
C5 C 0.72506(13) 0.2947(5) 1.00719(12) 0.0396 1.0000 Uani . . . . 3 . .
C6 C 0.63975(14) 0.1139(5) 1.00890(16) 0.0497 1.0000 Uani . . . . 3 . .
C7 C 0.56702(17) 0.1259(6) 1.08853(19) 0.0591 1.0000 Uani . . . . 3 . .
C8 C 0.57878(18) 0.3151(6) 1.16537(17) 0.0596 1.0000 Uani . . . . 3 . .
C9 C 0.6636(2) 0.4939(6) 1.16549(17) 0.0650 1.0000 Uani . . . . 3 . .
C10 C 0.73664(18) 0.4823(6) 1.08674(14) 0.0534 1.0000 Uani . . . . 3 . .
C11 C 0.89735(14) 0.0880(5) 0.94603(17) 0.0508 1.0000 Uani . . . . 3 . .
C12 C 0.67037(14) 0.3102(5) 0.64679(13) 0.0410 1.0000 Uani . . . . 3 . .
C13 C 0.55206(15) 0.3974(6) 0.62851(16) 0.0559 1.0000 Uani . . . . 3 . .
C14 C 0.74346(15) 0.4255(6) 0.56356(14) 0.0475 1.0000 Uani . . . . 3 . .
C15 C 0.85869(16) 0.3343(6) 0.58624(17) 0.0559 1.0000 Uani . . . . 3 . .
C16 C 0.93460(16) 0.4812(6) 0.63786(19) 0.0610 1.0000 Uani . . . . 3 . .
C17 C 1.04401(18) 0.3885(9) 0.6670(3) 0.0848 1.0000 Uani . . . . 3 . .
C18 C 1.1122(2) 0.5284(12) 0.7292(3) 0.1018 1.0000 Uani . . . . 3 . .
C19 C 0.7033(2) 0.3446(8) 0.45276(17) 0.0710 1.0000 Uani . . . . 3 . .
H41 H 0.8382(17) 0.463(6) 0.9167(18) 0.0458 1.0000 Uiso . . . . 3 . .
H61 H 0.6292(19) -0.025(7) 0.955(2) 0.0587 1.0000 Uiso . . . . 3 . .
H71 H 0.504(2) 0.005(9) 1.088(2) 0.0698 1.0000 Uiso . . . . 3 . .
H81 H 0.521(2) 0.326(8) 1.219(2) 0.0712 1.0000 Uiso . . . . 3 . .
H91 H 0.674(2) 0.637(9) 1.223(3) 0.0766 1.0000 Uiso . . . . 3 . .
H101 H 0.795(2) 0.613(8) 1.090(2) 0.0624 1.0000 Uiso . . . . 3 . .
H111 H 0.9327(19) 0.126(7) 1.014(2) 0.0599 1.0000 Uiso . . . . 3 . .
H112 H 0.949(2) 0.091(7) 0.896(2) 0.0599 1.0000 Uiso . . . . 3 . .
H113 H 0.862(2) -0.096(8) 0.943(2) 0.0599 1.0000 Uiso . . . . 3 . .
H121 H 0.6719(18) 0.117(7) 0.6476(18) 0.0486 1.0000 Uiso . . . . 3 . .
H131 H 0.520(2) 0.323(7) 0.561(2) 0.0656 1.0000 Uiso . . . . 3 . .
H132 H 0.549(2) 0.633(9) 0.629(2) 0.0656 1.0000 Uiso . . . . 3 . .
H133 H 0.512(2) 0.334(8) 0.685(2) 0.0656 1.0000 Uiso . . . . 3 . .
H141 H 0.7432(19) 0.640(8) 0.569(2) 0.0557 1.0000 Uiso . . . . 3 . .
H151 H 0.880(2) 0.159(9) 0.561(2) 0.0664 1.0000 Uiso . . . . 3 . .
H161 H 0.911(2) 0.678(9) 0.662(2) 0.0731 1.0000 Uiso . . . . 3 . .
H171 H 1.067(3) 0.214(13) 0.641(3) 0.1002 1.0000 Uiso . . . . 3 . .
H181 H 1.190(4) 0.462(13) 0.751(4) 0.1190 1.0000 Uiso . . . . 3 . .
H182 H 1.077(3) 0.712(13) 0.769(4) 0.1190 1.0000 Uiso . . . . 3 . .
H191 H 0.754(3) 0.398(11) 0.401(3) 0.0840 1.0000 Uiso . . . . 3 . .
H192 H 0.697(3) 0.150(10) 0.452(3) 0.0840 1.0000 Uiso . . . . 3 . .
H193 H 0.629(3) 0.414(10) 0.436(3) 0.0840 1.0000 Uiso . . . . 3 . .
H31 H 0.7459(18) 0.042(7) 0.7998(18) 0.0471 1.0000 Uiso . . . . 3 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0738(8) 0.0208(6) 0.0543(7) -0.0031(5) -0.0059(5) 0.0006(5)
C2 0.0504(7) 0.0209(7) 0.0421(7) -0.0025(6) 0.0016(5) -0.0028(6)
N3 0.0562(7) 0.0197(6) 0.0439(7) -0.0022(5) -0.0018(5) -0.0027(5)
C4 0.0472(7) 0.0238(8) 0.0456(7) -0.0011(6) -0.0033(6) -0.0060(6)
C5 0.0473(7) 0.0265(7) 0.0439(7) 0.0044(6) -0.0060(5) 0.0019(6)
C6 0.0499(8) 0.0399(10) 0.0590(9) -0.0015(8) -0.0004(7) -0.0071(7)
C7 0.0542(9) 0.0525(12) 0.0709(11) 0.0046(10) 0.0071(8) -0.0061(9)
C8 0.0696(11) 0.0532(12) 0.0574(10) 0.0130(9) 0.0158(8) 0.0081(10)
C9 0.0978(16) 0.0496(12) 0.0483(9) -0.0027(10) 0.0115(9) -0.0023(12)
C10 0.0743(11) 0.0414(11) 0.0444(8) -0.0042(8) 0.0034(7) -0.0113(9)
C11 0.0458(8) 0.0397(12) 0.0661(11) -0.0032(8) -0.0037(7) 0.0025(7)
C12 0.0507(7) 0.0294(8) 0.0427(7) -0.0040(6) -0.0005(6) -0.0021(6)
C13 0.0490(8) 0.0623(13) 0.0561(9) -0.0086(10) 0.0004(7) -0.0016(9)
C14 0.0538(8) 0.0440(10) 0.0447(8) 0.0035(7) 0.0030(6) 0.0022(8)
C15 0.0528(9) 0.0543(13) 0.0610(10) 0.0013(9) 0.0080(7) 0.0065(9)
C16 0.0502(9) 0.0608(15) 0.0720(12) 0.0170(11) 0.0038(8) -0.0004(9)
C17 0.0493(10) 0.090(2) 0.115(2) 0.034(2) 0.0035(11) 0.0028(13)
C18 0.0628(13) 0.131(4) 0.109(2) 0.047(3) -0.0162(13) -0.0146(18)
C19 0.0713(11) 0.096(2) 0.0455(9) -0.0038(12) 0.0031(8) 0.0018(14)

_refine_ls_extinction_coef       99(15)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          5.73(2)
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 . C2 . 1.238(2) yes
C2 . N3 . 1.336(2) yes
C2 . C12 . 1.520(2) yes
N3 . C4 . 1.464(2) yes
N3 . H31 . 0.93(3) no
C4 . C5 . 1.520(2) yes
C4 . C11 . 1.529(2) yes
C4 . H41 . 0.98(3) no
C5 . C6 . 1.389(2) yes
C5 . C10 . 1.386(3) yes
C6 . C7 . 1.400(3) yes
C6 . H61 . 0.98(3) no
C7 . C8 . 1.367(4) yes
C7 . H71 . 0.99(4) no
C8 . C9 . 1.377(4) yes
C8 . H81 . 1.02(3) no
C9 . C10 . 1.394(3) yes
C9 . H91 . 1.03(4) no
C10 . H101 . 0.97(3) no
C11 . H111 . 0.98(3) no
C11 . H112 . 0.94(3) no
C11 . H113 . 1.01(4) no
C12 . C13 . 1.532(3) yes
C12 . C14 . 1.548(2) yes
C12 . H121 . 0.96(3) no
C13 . H131 . 1.00(3) no
C13 . H132 . 1.18(4) no
C13 . H133 . 0.95(3) no
C14 . C15 . 1.509(3) yes
C14 . C19 . 1.533(3) yes
C14 . H141 . 1.07(4) no
C15 . C16 . 1.337(4) yes
C15 . H151 . 0.98(4) no
C16 . C17 . 1.459(3) yes
C16 . H161 . 1.07(4) no
C17 . C18 . 1.327(6) yes
C17 . H171 . 0.98(6) no
C18 . H181 . 1.04(5) no
C18 . H182 . 1.14(6) no
C19 . H191 . 0.97(4) no
C19 . H192 . 0.97(5) no
C19 . H193 . 0.99(4) 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 . C2 . N3 . 122.72(16) yes
O1 . C2 . C12 . 121.01(16) yes
N3 . C2 . C12 . 116.27(15) yes
C2 . N3 . C4 . 122.47(14) yes
C2 . N3 . H31 . 118.5(15) no
C4 . N3 . H31 . 119.1(15) no
N3 . C4 . C5 . 112.44(13) yes
N3 . C4 . C11 . 109.04(14) yes
C5 . C4 . C11 . 112.23(14) yes
N3 . C4 . H41 . 108.1(13) no
C5 . C4 . H41 . 108.1(13) no
C11 . C4 . H41 . 106.6(13) no
C4 . C5 . C6 . 121.21(16) yes
C4 . C5 . C10 . 120.48(16) yes
C6 . C5 . C10 . 118.30(17) yes
C5 . C6 . C7 . 120.22(19) yes
C5 . C6 . H61 . 121.3(15) no
C7 . C6 . H61 . 118.5(15) no
C6 . C7 . C8 . 120.6(2) yes
C6 . C7 . H71 . 120.7(19) no
C8 . C7 . H71 . 118.6(19) no
C7 . C8 . C9 . 119.91(19) yes
C7 . C8 . H81 . 118(2) no
C9 . C8 . H81 . 122(2) no
C8 . C9 . C10 . 119.8(2) yes
C8 . C9 . H91 . 121.0(19) no
C10 . C9 . H91 . 119.2(19) no
C9 . C10 . C5 . 121.2(2) yes
C9 . C10 . H101 . 117.0(18) no
C5 . C10 . H101 . 121.9(18) no
C4 . C11 . H111 . 110.7(18) no
C4 . C11 . H112 . 112.3(19) no
H111 . C11 . H112 . 109(2) no
C4 . C11 . H113 . 105.2(17) no
H111 . C11 . H113 . 112(3) no
H112 . C11 . H113 . 107(3) no
C2 . C12 . C13 . 109.46(14) yes
C2 . C12 . C14 . 108.01(14) yes
C13 . C12 . C14 . 112.24(15) yes
C2 . C12 . H121 . 107.8(14) no
C13 . C12 . H121 . 107.7(14) no
C14 . C12 . H121 . 111.6(14) no
C12 . C13 . H131 . 110.6(16) no
C12 . C13 . H132 . 108.3(14) no
H131 . C13 . H132 . 111(3) no
C12 . C13 . H133 . 108.8(18) no
H131 . C13 . H133 . 110(3) no
H132 . C13 . H133 . 108(3) no
C12 . C14 . C15 . 109.68(16) yes
C12 . C14 . C19 . 111.72(18) yes
C15 . C14 . C19 . 110.66(18) yes
C12 . C14 . H141 . 108.8(14) no
C15 . C14 . H141 . 107.1(13) no
C19 . C14 . H141 . 108.8(14) no
C14 . C15 . C16 . 124.0(2) yes
C14 . C15 . H151 . 118.6(16) no
C16 . C15 . H151 . 117.4(16) no
C15 . C16 . C17 . 124.7(3) yes
C15 . C16 . H161 . 116.7(16) no
C17 . C16 . H161 . 118.5(16) no
C16 . C17 . C18 . 122.5(4) yes
C16 . C17 . H171 . 118(3) no
C18 . C17 . H171 . 119(2) no
C17 . C18 . H181 . 123(3) no
C17 . C18 . H182 . 116(2) no
H181 . C18 . H182 . 120(4) no
C14 . C19 . H191 . 112(2) no
C14 . C19 . H192 . 107(2) no
H191 . C19 . H192 . 109(4) no
C14 . C19 . H193 . 111(2) no
H191 . C19 . H193 . 112(3) no
H192 . C19 . H193 . 106(4) 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
N3 . H31 . O1 1_545 171 0.93 2.02 2.938(4) yes

# Attachment 'CCDC719633.cif'

data_2
_database_code_depnum_ccdc_archive 'CCDC 719633'

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (G\"orbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The 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--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
\%A)
and
U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# Hand-made tables can be put in the cif. The number of columns
# is set in the loop header.
# The contants of each column can either be a piece of text
# without any spaces (eg a number) or other text enclosed in " "
# Remove the leading # in the following example

#geom_extra_table_head_A
#;
#Table 2.
#Molecular parameters deviating most from MOGUL averages
#;
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
#_geom_extra_tableA_col_4
#
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d"
#N5-C6-C4 129 124 "7 (\%)"
#C3-O10-C2 105 109 "2 (\%)"
#C6-O7 1.25 1.22 ".02 (\%A)"
#
# End of 'script/refcif-b.dat'
#end of refcif
_cell_length_a                   4.87270(10)
_cell_length_b                   10.8284(2)
_cell_length_c                   24.6333(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.4698(9)
_cell_angle_gamma                90
_cell_volume                     1293.82(5)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  ?
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 0.0033 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 57.7997
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'

_cell_formula_units_Z            2

# Given Formula = C30 H35 N1 O2
# Dc = 1.13 Fooo = 476.00 Mu = 0.70 M = 441.61
# Found Formula = C30 H35 N1 O2
# Dc = 1.13 FOOO = 476.00 Mu = 0.70 M = 441.61

_chemical_formula_sum            'C30 H35 N1 O2'
_chemical_formula_moiety         'C30 H35 N1 O2'
_chemical_compound_source        ?
_chemical_formula_weight         441.61

_cell_measurement_reflns_used    2474
_cell_measurement_theta_min      1
_cell_measurement_theta_max      28
_cell_measurement_temperature    190

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.070

# Sheldrick geometric approximatio 0.99 0.99
# No experimental values of Tmin/max available
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      190
_diffrn_reflns_number            4857
_reflns_number_total             2790
_diffrn_reflns_av_R_equivalents  0.015
# Number of reflections with Friedels Law is 2790
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3022

_diffrn_reflns_theta_min         1.661
_diffrn_reflns_theta_max         27.665
_diffrn_measured_fraction_theta_max 0.875

_diffrn_reflns_theta_full        25.175
_diffrn_measured_fraction_theta_full 0.985

_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.20
_refine_diff_density_max         0.23

# 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>0.5\s(I)
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     1
_refine_ls_number_parameters     298
_oxford_refine_ls_R_factor_ref   0.0536
_refine_ls_wR_factor_ref         0.0511
_refine_ls_goodness_of_fit_ref   1.1768
_refine_ls_shift/su_max          0.031673

# The values computed from all data
_oxford_reflns_number_all        2782
_refine_ls_R_factor_all          0.0683
_refine_ls_wR_factor_all         0.0728

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1974
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_gt          0.0444

# 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    noref # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.433 0.286 0.191
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 1.3179(3) 0.6786(2) 0.20017(8) 0.0454 1.0000 Uani . . . . 3 . .
C2 C 1.0631(5) 0.6709(3) 0.19092(10) 0.0341 1.0000 Uani . . . . 3 . .
N3 N 0.8900(4) 0.7456(2) 0.21393(8) 0.0331 1.0000 Uani . . . . 3 . .
C4 C 0.9905(5) 0.8403(3) 0.25337(11) 0.0396 1.0000 Uani . . . . 3 . .
C5 C 0.7801(5) 0.9438(3) 0.25257(13) 0.0431 1.0000 Uani . . . . 3 . .
C6 C 0.6767(6) 0.9944(3) 0.20327(15) 0.0550 1.0000 Uani . . . . 3 . .
C7 C 0.4841(7) 1.0913(4) 0.2017(2) 0.0729 1.0000 Uani . . . . 3 . .
C8 C 0.3985(8) 1.1356(3) 0.2498(2) 0.0793 1.0000 Uani . . . . 3 . .
C9 C 0.5008(8) 1.0865(4) 0.2988(2) 0.0789 1.0000 Uani . . . . 3 . .
C10 C 0.6907(7) 0.9920(4) 0.30023(15) 0.0603 1.0000 Uani . . . . 3 . .
C11 C 1.0682(8) 0.7841(4) 0.30854(13) 0.0664 1.0000 Uani . . . . 3 . .
C12 C 0.9372(5) 0.5751(3) 0.15124(11) 0.0354 1.0000 Uani . . . . 3 . .
C13 C 1.0059(5) 0.4453(3) 0.17479(11) 0.0394 1.0000 Uani . . . . 3 . .
C14 C 0.8918(5) 0.4314(3) 0.22912(11) 0.0403 1.0000 Uani . . . . 3 . .
C15 C 1.0313(5) 0.4346(3) 0.27732(12) 0.0419 1.0000 Uani . . . . 3 . .
C16 C 0.9092(6) 0.4211(3) 0.33050(12) 0.0498 1.0000 Uani . . . . 3 . .
C17 C 1.0205(6) 0.3105(3) 0.36277(11) 0.0437 1.0000 Uani . . . . 3 . .
O18 O 0.8759(4) 0.3004(2) 0.41021(8) 0.0496 1.0000 Uani . . . . 3 . .
C19 C 0.9773(6) 0.2018(3) 0.44488(12) 0.0511 1.0000 Uani . . . . 3 . .
C20 C 0.8028(6) 0.1930(3) 0.49200(11) 0.0454 1.0000 Uani . . . . 3 . .
C21 C 0.7255(7) 0.0783(4) 0.51093(15) 0.0578 1.0000 Uani . . . . 3 . .
C22 C 0.5606(8) 0.0708(4) 0.55417(15) 0.0645 1.0000 Uani . . . . 3 . .
C23 C 0.4775(7) 0.1738(5) 0.57846(13) 0.0674 1.0000 Uani . . . . 3 . .
C24 C 0.5562(8) 0.2890(4) 0.56061(14) 0.0653 1.0000 Uani . . . . 3 . .
C25 C 0.7191(7) 0.2978(3) 0.51741(13) 0.0536 1.0000 Uani . . . . 3 . .
C26 C 0.8969(8) 0.3418(3) 0.13618(15) 0.0595 1.0000 Uani . . . . 3 . .
C27 C 1.0458(6) 0.5974(3) 0.09564(12) 0.0462 1.0000 Uani . . . . 3 . .
C28 C 0.9652(6) 0.7221(4) 0.07109(12) 0.0547 1.0000 Uani . . . . 3 . .
C29 C 1.1097(10) 0.8288(4) 0.08766(16) 0.0757 1.0000 Uani . . . . 3 . .
C30 C 1.0385(14) 0.9446(5) 0.0682(2) 0.1029 1.0000 Uani . . . . 3 . .
C31 C 0.8208(15) 0.9541(7) 0.0316(3) 0.1127 1.0000 Uani . . . . 3 . .
C32 C 0.6666(11) 0.8556(8) 0.0118(2) 0.1197 1.0000 Uani . . . . 3 . .
C33 C 0.7430(9) 0.7330(6) 0.03259(17) 0.0949 1.0000 Uani . . . . 3 . .
H41 H 1.1667 0.8819 0.2436 0.0494 1.0000 Uiso . . . . 3 . .
H61 H 0.7440 0.9614 0.1680 0.0623 1.0000 Uiso . . . . 3 . .
H71 H 0.4117 1.1277 0.1646 0.0916 1.0000 Uiso . . . . 3 . .
H81 H 0.2487 1.2036 0.2492 0.0997 1.0000 Uiso . . . . 3 . .
H91 H 0.4439 1.1254 0.3333 0.0996 1.0000 Uiso . . . . 3 . .
H101 H 0.7711 0.9549 0.3380 0.0774 1.0000 Uiso . . . . 3 . .
H111 H 1.1363 0.8476 0.3364 0.0823 1.0000 Uiso . . . . 3 . .
H112 H 1.2119 0.7187 0.3068 0.0823 1.0000 Uiso . . . . 3 . .
H113 H 0.8981 0.7433 0.3224 0.0823 1.0000 Uiso . . . . 3 . .
H121 H 0.7285 0.5812 0.1456 0.0427 1.0000 Uiso . . . . 3 . .
H131 H 1.2144 0.4374 0.1788 0.0498 1.0000 Uiso . . . . 3 . .
H141 H 0.6857 0.4172 0.2287 0.0496 1.0000 Uiso . . . . 3 . .
H151 H 1.2408 0.4471 0.2790 0.0520 1.0000 Uiso . . . . 3 . .
H161 H 0.9462 0.4966 0.3537 0.0599 1.0000 Uiso . . . . 3 . .
H162 H 0.7025 0.4112 0.3230 0.0599 1.0000 Uiso . . . . 3 . .
H171 H 1.2252 0.3200 0.3720 0.0566 1.0000 Uiso . . . . 3 . .
H172 H 0.9922 0.2332 0.3387 0.0566 1.0000 Uiso . . . . 3 . .
H191 H 1.1754 0.2143 0.4582 0.0642 1.0000 Uiso . . . . 3 . .
H192 H 0.9643 0.1201 0.4233 0.0642 1.0000 Uiso . . . . 3 . .
H211 H 0.7912 0.0003 0.4934 0.0684 1.0000 Uiso . . . . 3 . .
H221 H 0.5045 -0.0142 0.5677 0.0787 1.0000 Uiso . . . . 3 . .
H231 H 0.3537 0.1653 0.6089 0.0811 1.0000 Uiso . . . . 3 . .
H241 H 0.4953 0.3666 0.5798 0.0786 1.0000 Uiso . . . . 3 . .
H251 H 0.7846 0.3829 0.5040 0.0663 1.0000 Uiso . . . . 3 . .
H261 H 0.9427 0.2587 0.1530 0.0697 1.0000 Uiso . . . . 3 . .
H262 H 0.9668 0.3483 0.1004 0.0697 1.0000 Uiso . . . . 3 . .
H263 H 0.6850 0.3479 0.1313 0.0697 1.0000 Uiso . . . . 3 . .
H271 H 1.2515 0.5902 0.0998 0.0579 1.0000 Uiso . . . . 3 . .
H272 H 0.9698 0.5312 0.0691 0.0579 1.0000 Uiso . . . . 3 . .
H291 H 1.2809 0.8205 0.1160 0.0977 1.0000 Uiso . . . . 3 . .
H301 H 1.1475 1.0218 0.0816 0.1237 1.0000 Uiso . . . . 3 . .
H311 H 0.7672 1.0425 0.0187 0.1424 1.0000 Uiso . . . . 3 . .
H321 H 0.4974 0.8678 -0.0166 0.1448 1.0000 Uiso . . . . 3 . .
H331 H 0.6336 0.6544 0.0179 0.1162 1.0000 Uiso . . . . 3 . .
H31 H 0.6794 0.7292 0.2053 0.0500 1.0000 Uiso . . . . 3 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0217(8) 0.0579(12) 0.0569(11) -0.0069(11) 0.0040(7) -0.0014(9)
C2 0.0233(11) 0.0430(15) 0.0363(13) 0.0022(12) 0.0052(9) -0.0020(11)
N3 0.0221(9) 0.0380(12) 0.0392(11) -0.0021(10) 0.0024(8) -0.0013(9)
C4 0.0309(12) 0.0407(15) 0.0467(15) -0.0056(13) 0.0017(11) 0.0004(11)
C5 0.0330(13) 0.0370(14) 0.0604(18) -0.0076(14) 0.0098(12) -0.0045(12)
C6 0.0423(16) 0.0452(18) 0.079(2) 0.0084(17) 0.0156(15) 0.0041(14)
C7 0.0510(19) 0.049(2) 0.118(3) 0.016(2) 0.005(2) 0.0028(17)
C8 0.053(2) 0.0433(19) 0.144(4) -0.019(2) 0.021(2) 0.0054(17)
C9 0.058(2) 0.069(3) 0.110(3) -0.041(3) 0.009(2) 0.007(2)
C10 0.0471(17) 0.059(2) 0.076(2) -0.0291(19) 0.0082(16) -0.0011(16)
C11 0.086(2) 0.063(2) 0.0472(17) -0.0061(17) -0.0081(17) 0.010(2)
C12 0.0271(12) 0.0450(16) 0.0343(13) -0.0022(12) 0.0039(10) -0.0010(11)
C13 0.0332(12) 0.0430(15) 0.0420(14) -0.0050(13) 0.0042(11) 0.0019(12)
C14 0.0322(13) 0.0437(16) 0.0457(15) 0.0050(13) 0.0074(12) 0.0010(12)
C15 0.0368(13) 0.0443(16) 0.0457(15) 0.0024(14) 0.0089(11) 0.0057(13)
C16 0.0519(16) 0.0544(19) 0.0446(15) 0.0060(15) 0.0122(13) 0.0107(15)
C17 0.0401(14) 0.0502(17) 0.0419(14) 0.0040(14) 0.0107(11) 0.0053(13)
O18 0.0497(11) 0.0572(13) 0.0436(10) 0.0087(10) 0.0135(9) 0.0132(10)
C19 0.0487(15) 0.054(2) 0.0504(16) 0.0141(16) 0.0044(13) 0.0089(15)
C20 0.0401(14) 0.0544(19) 0.0409(14) 0.0018(15) -0.0009(11) -0.0002(14)
C21 0.0567(19) 0.055(2) 0.062(2) 0.0109(17) 0.0063(16) 0.0027(17)
C22 0.065(2) 0.073(3) 0.055(2) 0.018(2) 0.0026(17) -0.011(2)
C23 0.066(2) 0.095(3) 0.0408(17) 0.009(2) 0.0072(15) -0.007(2)
C24 0.076(2) 0.075(3) 0.0464(18) -0.0069(18) 0.0118(16) -0.001(2)
C25 0.0605(19) 0.053(2) 0.0467(16) -0.0006(15) 0.0046(14) -0.0044(17)
C26 0.073(2) 0.0467(18) 0.0594(19) -0.0090(16) 0.0070(16) -0.0054(17)
C27 0.0424(15) 0.0582(19) 0.0390(15) -0.0013(14) 0.0089(12) 0.0038(15)
C28 0.0462(16) 0.084(3) 0.0362(14) 0.0109(17) 0.0171(12) 0.0110(17)
C29 0.102(3) 0.065(3) 0.063(2) 0.016(2) 0.020(2) -0.002(2)
C30 0.151(5) 0.087(3) 0.078(3) 0.027(3) 0.042(3) 0.008(4)
C31 0.113(4) 0.138(5) 0.097(4) 0.045(4) 0.062(4) 0.041(4)
C32 0.067(3) 0.196(8) 0.096(4) 0.066(5) 0.008(3) 0.037(4)
C33 0.065(2) 0.147(5) 0.072(3) 0.046(3) 0.000(2) 0.010(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.6597(15)
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 . C2 . 1.243(3) yes
C2 . N3 . 1.334(3) yes
C2 . C12 . 1.514(4) yes
N3 . C4 . 1.464(3) yes
N3 . H31 . 1.044 no
C4 . C5 . 1.517(4) yes
C4 . C11 . 1.504(4) yes
C4 . H41 . 1.019 no
C5 . C6 . 1.383(5) yes
C5 . C10 . 1.393(4) yes
C6 . C7 . 1.406(5) yes
C6 . H61 . 1.021 no
C7 . C8 . 1.381(6) yes
C7 . H71 . 1.025 no
C8 . C9 . 1.368(7) yes
C8 . H81 . 1.035 no
C9 . C10 . 1.377(6) yes
C9 . H91 . 1.011 no
C10 . H101 . 1.054 no
C11 . H111 . 1.005 no
C11 . H112 . 1.000 no
C11 . H113 . 1.026 no
C12 . C13 . 1.545(4) yes
C12 . C27 . 1.534(4) yes
C12 . H121 . 1.016 no
C13 . C14 . 1.505(4) yes
C13 . C26 . 1.532(4) yes
C13 . H131 . 1.015 no
C14 . C15 . 1.311(4) yes
C14 . H141 . 1.015 no
C15 . C16 . 1.497(4) yes
C15 . H151 . 1.027 no
C16 . C17 . 1.509(4) yes
C16 . H161 . 1.004 no
C16 . H162 . 1.012 no
C17 . O18 . 1.425(3) yes
C17 . H171 . 1.007 no
C17 . H172 . 1.028 no
O18 . C19 . 1.426(4) yes
C19 . C20 . 1.506(4) yes
C19 . H191 . 0.999 no
C19 . H192 . 1.030 no
C20 . C21 . 1.391(5) yes
C20 . C25 . 1.377(5) yes
C21 . C22 . 1.396(5) yes
C21 . H211 . 1.014 no
C22 . C23 . 1.346(6) yes
C22 . H221 . 1.025 no
C23 . C24 . 1.388(6) yes
C23 . H231 . 1.011 no
C24 . C25 . 1.390(5) yes
C24 . H241 . 1.021 no
C25 . H251 . 1.038 no
C26 . H261 . 1.007 no
C26 . H262 . 0.978 no
C26 . H263 . 1.030 no
C27 . C28 . 1.516(5) yes
C27 . H271 . 1.001 no
C27 . H272 . 1.016 no
C28 . C29 . 1.393(6) yes
C28 . C33 . 1.375(5) yes
C29 . C30 . 1.376(7) yes
C29 . H291 . 1.039 no
C30 . C31 . 1.328(9) yes
C30 . H301 . 1.028 no
C31 . C32 . 1.368(10) yes
C31 . H311 . 1.034 no
C32 . C33 . 1.459(9) yes
C32 . H321 . 1.038 no
C33 . H331 . 1.050 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 . C2 . N3 . 122.9(2) yes
O1 . C2 . C12 . 120.0(2) yes
N3 . C2 . C12 . 117.1(2) yes
C2 . N3 . C4 . 121.4(2) yes
C2 . N3 . H31 . 117.3 no
C4 . N3 . H31 . 121.0 no
N3 . C4 . C5 . 109.0(2) yes
N3 . C4 . C11 . 110.8(3) yes
C5 . C4 . C11 . 115.0(3) yes
N3 . C4 . H41 . 112.8 no
C5 . C4 . H41 . 104.7 no
C11 . C4 . H41 . 104.4 no
C4 . C5 . C6 . 119.6(3) yes
C4 . C5 . C10 . 122.1(3) yes
C6 . C5 . C10 . 118.3(3) yes
C5 . C6 . C7 . 120.5(3) yes
C5 . C6 . H61 . 119.2 no
C7 . C6 . H61 . 120.3 no
C6 . C7 . C8 . 119.4(4) yes
C6 . C7 . H71 . 119.0 no
C8 . C7 . H71 . 121.6 no
C7 . C8 . C9 . 120.5(4) yes
C7 . C8 . H81 . 120.3 no
C9 . C8 . H81 . 119.1 no
C8 . C9 . C10 . 119.9(4) yes
C8 . C9 . H91 . 118.2 no
C10 . C9 . H91 . 121.7 no
C5 . C10 . C9 . 121.4(4) yes
C5 . C10 . H101 . 118.7 no
C9 . C10 . H101 . 119.9 no
C4 . C11 . H111 . 112.2 no
C4 . C11 . H112 . 111.4 no
H111 . C11 . H112 . 109.1 no
C4 . C11 . H113 . 109.4 no
H111 . C11 . H113 . 107.0 no
H112 . C11 . H113 . 107.4 no
C2 . C12 . C13 . 108.7(2) yes
C2 . C12 . C27 . 108.4(2) yes
C13 . C12 . C27 . 113.4(2) yes
C2 . C12 . H121 . 112.5 no
C13 . C12 . H121 . 106.8 no
C27 . C12 . H121 . 107.0 no
C12 . C13 . C14 . 109.9(2) yes
C12 . C13 . C26 . 112.5(2) yes
C14 . C13 . C26 . 110.0(3) yes
C12 . C13 . H131 . 107.0 no
C14 . C13 . H131 . 110.9 no
C26 . C13 . H131 . 106.4 no
C13 . C14 . C15 . 126.8(2) yes
C13 . C14 . H141 . 117.1 no
C15 . C14 . H141 . 116.1 no
C14 . C15 . C16 . 125.1(3) yes
C14 . C15 . H151 . 117.9 no
C16 . C15 . H151 . 117.0 no
C15 . C16 . C17 . 112.7(2) yes
C15 . C16 . H161 . 110.7 no
C17 . C16 . H161 . 108.1 no
C15 . C16 . H162 . 108.7 no
C17 . C16 . H162 . 108.3 no
H161 . C16 . H162 . 108.2 no
C16 . C17 . O18 . 108.2(2) yes
C16 . C17 . H171 . 109.7 no
O18 . C17 . H171 . 112.3 no
C16 . C17 . H172 . 108.7 no
O18 . C17 . H172 . 111.2 no
H171 . C17 . H172 . 106.8 no
C17 . O18 . C19 . 112.2(2) yes
O18 . C19 . C20 . 108.7(2) yes
O18 . C19 . H191 . 111.3 no
C20 . C19 . H191 . 110.8 no
O18 . C19 . H192 . 109.5 no
C20 . C19 . H192 . 109.4 no
H191 . C19 . H192 . 107.2 no
C19 . C20 . C21 . 120.4(3) yes
C19 . C20 . C25 . 120.8(3) yes
C21 . C20 . C25 . 118.8(3) yes
C20 . C21 . C22 . 120.1(4) yes
C20 . C21 . H211 . 119.6 no
C22 . C21 . H211 . 120.3 no
C21 . C22 . C23 . 120.7(4) yes
C21 . C22 . H221 . 119.4 no
C23 . C22 . H221 . 119.9 no
C22 . C23 . C24 . 120.0(3) yes
C22 . C23 . H231 . 118.7 no
C24 . C23 . H231 . 121.3 no
C23 . C24 . C25 . 120.0(4) yes
C23 . C24 . H241 . 119.4 no
C25 . C24 . H241 . 120.6 no
C24 . C25 . C20 . 120.4(3) yes
C24 . C25 . H251 . 121.3 no
C20 . C25 . H251 . 118.3 no
C13 . C26 . H261 . 110.4 no
C13 . C26 . H262 . 112.2 no
H261 . C26 . H262 . 110.7 no
C13 . C26 . H263 . 108.1 no
H261 . C26 . H263 . 106.6 no
H262 . C26 . H263 . 108.8 no
C12 . C27 . C28 . 113.4(2) yes
C12 . C27 . H271 . 108.9 no
C28 . C27 . H271 . 109.2 no
C12 . C27 . H272 . 109.2 no
C28 . C27 . H272 . 107.9 no
H271 . C27 . H272 . 108.1 no
C27 . C28 . C29 . 121.1(3) yes
C27 . C28 . C33 . 120.6(4) yes
C29 . C28 . C33 . 118.3(4) yes
C28 . C29 . C30 . 123.4(5) yes
C28 . C29 . H291 . 118.5 no
C30 . C29 . H291 . 118.2 no
C29 . C30 . C31 . 117.7(6) yes
C29 . C30 . H301 . 121.5 no
C31 . C30 . H301 . 120.7 no
C30 . C31 . C32 . 123.9(6) yes
C30 . C31 . H311 . 116.3 no
C32 . C31 . H311 . 119.8 no
C31 . C32 . C33 . 118.1(5) yes
C31 . C32 . H321 . 121.0 no
C33 . C32 . H321 . 120.9 no
C32 . C33 . C28 . 118.6(5) yes
C32 . C33 . H331 . 120.8 no
C28 . C33 . H331 . 120.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C29 . H291 . O1 . 126 1.04 2.57 3.290(5) yes
N3 . H31 . O1 1_455 169 1.04 1.84 2.869(5) yes

# Attachment 'CCDC719634.cif'

data_3
_database_code_depnum_ccdc_archive 'CCDC 719634'

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (G\"orbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The 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--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
\%A)
and
U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# Hand-made tables can be put in the cif. The number of columns
# is set in the loop header.
# The contants of each column can either be a piece of text
# without any spaces (eg a number) or other text enclosed in " "
# Remove the leading # in the following example

#geom_extra_table_head_A
#;
#Table 2.
#Molecular parameters deviating most from MOGUL averages
#;
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
#_geom_extra_tableA_col_4
#
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d"
#N5-C6-C4 129 124 "7 (\%)"
#C3-O10-C2 105 109 "2 (\%)"
#C6-O7 1.25 1.22 ".02 (\%A)"
#
# End of 'script/refcif-b.dat'
#end of refcif
_cell_length_a                   8.9487(2)
_cell_length_b                   5.18510(10)
_cell_length_c                   52.2900(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2426.25(8)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

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

_cell_formula_units_Z            4

# Given Formula = C29 H33 N1 O2
# Dc = 1.17 Fooo = 917.30 Mu = 0.72 M = 427.59
# Found Formula = C29 H32.33 N1 O2
# Dc = 1.17 FOOO = 917.30 Mu = 0.72 M = 426.91

_chemical_formula_sum            'C29 H32.33 N1 O2'
_chemical_formula_moiety         'C29 H32.33 N1 O2'
_chemical_compound_source        ?
_chemical_formula_weight         426.91

_cell_measurement_reflns_used    4948
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    190

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.10

_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             917.303
_exptl_absorpt_coefficient_mu    0.072

# Sheldrick geometric approximatio 0.99 0.99
# No experimental values of Tmin/max available
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'USER DEFINED STRUCTURE SOLUTION'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      190
_diffrn_reflns_number            4856
_reflns_number_total             3067
_diffrn_reflns_av_R_equivalents  0.037
# Number of reflections with Friedels Law is 3067
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2762

_diffrn_reflns_theta_min         5.111
_diffrn_reflns_theta_max         27.411
_diffrn_measured_fraction_theta_max 0.939

_diffrn_reflns_theta_full        25.218
_diffrn_measured_fraction_theta_full 0.951

_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -66
_diffrn_reflns_limit_l_max       67
_reflns_limit_h_min              0
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              67

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.40
_refine_diff_density_max         0.63

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

# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>1.5\s(I)
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     24
_refine_ls_number_parameters     302
_oxford_refine_ls_R_factor_ref   0.0809
_refine_ls_wR_factor_ref         0.1587
_refine_ls_goodness_of_fit_ref   0.9860
_refine_ls_shift/su_max          0.023145

# The values computed from all data
_oxford_reflns_number_all        3066
_refine_ls_R_factor_all          0.0983
_refine_ls_wR_factor_all         0.1858

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2375
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_gt          0.1550

# 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 Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref # none, undef, noref, refall,
# refxyz, refU, constr or mixed

# WARNING. The IUCr will not accept Unit Weights
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Quasi-Unit weights
W = 1.0 or 1./2F
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
User-defined structure solution reference

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.6075(4) 0.3652(6) 0.58147(6) 0.0430 1.0000 Uani . . . . 3 . .
O9 O 0.6812(6) 0.6674(9) 0.71230(7) 0.0876 1.0000 Uani . . . . 3 . .
N2 N 0.6753(4) -0.0570(6) 0.57909(7) 0.0341 1.0000 Uani . . . . 3 . .
C3 C 0.8074(4) -0.0126(8) 0.56373(7) 0.0321 1.0000 Uani . . . . 3 . .
C4 C 0.0961(5) 0.3151(9) 0.61685(8) 0.0394 1.0000 Uani . . . . 3 . .
C5 C 0.2159(5) 0.1701(8) 0.62514(8) 0.0339 1.0000 Uani . . . . 3 . .
C6 C 0.5807(5) 0.1332(8) 0.58583(7) 0.0323 1.0000 Uani . . . . 3 . .
C7 C 0.7749(5) -0.0048(8) 0.53514(8) 0.0350 1.0000 Uani . . . . 3 . .
C8 C 0.3732(5) 0.2382(9) 0.61718(8) 0.0353 1.0000 Uani . . . . 3 . .
C10 C 0.4346(5) 0.0419(8) 0.59737(7) 0.0324 1.0000 Uani . . . . 3 . .
C11 C 0.8499(6) 0.1695(9) 0.51957(9) 0.0470 1.0000 Uani . . . . 3 . .
C12 C -0.0490(5) 0.2539(11) 0.62345(9) 0.0461 1.0000 Uani . . . . 3 . .
C13 C 0.3276(5) -0.0054(12) 0.57539(9) 0.0536 1.0000 Uani . . . . 3 . .
C14 C 0.9216(5) -0.2224(9) 0.56988(8) 0.0407 1.0000 Uani . . . . 3 . .
C15 C 0.1851(5) -0.0457(9) 0.64046(8) 0.0418 1.0000 Uani . . . . 3 . .
C16 C 0.6781(6) -0.1778(10) 0.52384(9) 0.0492 1.0000 Uani . . . . 3 . .
C17 C 0.4749(6) 0.2608(11) 0.64002(9) 0.0532 1.0000 Uani . . . . 3 . .
C18 C -0.0765(6) 0.0417(11) 0.63873(9) 0.0519 1.0000 Uani . . . . 3 . .
C19 C 0.6571(6) -0.1780(10) 0.49757(9) 0.0560 1.0000 Uani . . . . 3 . .
C20 C 0.0402(6) -0.1079(10) 0.64723(9) 0.0495 1.0000 Uani . . . . 3 . .
C21 C 0.7327(7) -0.0042(11) 0.48235(9) 0.0555 1.0000 Uani . . . . 3 . .
C22 C 0.8324(7) 0.1683(10) 0.49324(9) 0.0566 1.0000 Uani . . . . 3 . .
C23 C 0.5570(8) 0.4404(12) 0.64808(11) 0.0761 1.0000 Uani . . . . 3 . .
C24 C 0.6456(8) 0.4502(12) 0.67236(11) 0.0730 1.0000 Uani . . . . 3 . .
C25 C 0.8841(8) 0.8303(12) 0.79911(12) 0.0944 1.0000 Uani D . . . 3 . .
C26 C 0.5939(11) 0.6730(16) 0.68932(12) 0.1099 1.0000 Uani . . . . 3 . .
C27 C 0.7470(9) 0.8606(12) 0.75140(11) 0.1113 1.0000 Uani D . . . 3 . .
C28 C 0.6663(19) 0.882(2) 0.72644(18) 0.2148 1.0000 Uani . . . . 3 . .
C29 C 0.7953(10) 0.633(2) 0.79013(16) 0.1128 0.664(7) Uani D . P . 3 . .
C31 C 0.972(3) 0.8270(19) 0.7773(3) 0.1890 0.336(7) Uani D . P . 3 . .
C32 C 0.7266(10) 0.647(2) 0.76655(17) 0.1078 0.664(7) Uani D . P . 3 . .
C33 C 0.9012(14) 0.8418(19) 0.7537(5) 0.2227 0.336(7) Uani D . P . 3 . .
C102 C 0.8379(11) 1.057(2) 0.7604(2) 0.2227 0.664(7) Uani D . P . 3 . .
C101 C 0.7323(14) 0.8487(18) 0.7974(3) 0.1128 0.336(7) Uani D . P . 3 . .
C100 C 0.667(2) 0.8629(19) 0.7737(2) 0.1078 0.336(7) Uani D . P . 3 . .
C103 C 0.9070(12) 1.043(2) 0.78434(18) 0.1890 0.664(7) Uani D . P . 3 . .
H31 H 0.8497 0.1627 0.5683 0.0391 1.0000 Uiso . . . . . . .
H41 H 0.1143 0.4741 0.6054 0.0493 1.0000 Uiso . . . . . . .
H81 H 0.3716 0.4132 0.6081 0.0433 1.0000 Uiso . . . . . . .
H101 H 0.4501 -0.1221 0.6081 0.0394 1.0000 Uiso . . . . . . .
H111 H 0.9203 0.2975 0.5278 0.0561 1.0000 Uiso . . . . . . .
H121 H -0.1361 0.3636 0.6168 0.0577 1.0000 Uiso . . . . . . .
H131 H 0.2283 -0.0691 0.5819 0.0672 1.0000 Uiso . . . . . . .
H132 H 0.3118 0.1576 0.5656 0.0672 1.0000 Uiso . . . . . . .
H133 H 0.3696 -0.1403 0.5635 0.0672 1.0000 Uiso . . . . . . .
H141 H 1.0145 -0.1934 0.5595 0.0481 1.0000 Uiso . . . . . . .
H142 H 0.9471 -0.2169 0.5884 0.0481 1.0000 Uiso . . . . . . .
H143 H 0.8780 -0.3937 0.5654 0.0481 1.0000 Uiso . . . . . . .
H151 H 0.2712 -0.1572 0.6465 0.0487 1.0000 Uiso . . . . . . .
H161 H 0.6232 -0.3022 0.5349 0.0611 1.0000 Uiso . . . . . . .
H171 H 0.4782 0.1012 0.6514 0.0635 1.0000 Uiso . . . . . . .
H181 H -0.1833 0.0025 0.6446 0.0611 1.0000 Uiso . . . . . . .
H191 H 0.5826 -0.3028 0.4898 0.0687 1.0000 Uiso . . . . . . .
H201 H 0.0213 -0.2657 0.6581 0.0582 1.0000 Uiso . . . . . . .
H211 H 0.7163 -0.0057 0.4630 0.0662 1.0000 Uiso . . . . . . .
H221 H 0.8900 0.2886 0.4820 0.0707 1.0000 Uiso . . . . . . .
H231 H 0.5571 0.6030 0.6365 0.0942 1.0000 Uiso . . . . . . .
H241 H 0.6286 0.2827 0.6826 0.0990 1.0000 Uiso . . . . . . .
H242 H 0.7548 0.4649 0.6691 0.0990 1.0000 Uiso . . . . . . .
H261 H 0.4851 0.6589 0.6933 0.1295 1.0000 Uiso . . . . . . .
H262 H 0.6109 0.8413 0.6797 0.1295 1.0000 Uiso . . . . . . .
H281 H 0.5601 0.9303 0.7298 0.2535 1.0000 Uiso . . . . . . .
H282 H 0.7131 1.0426 0.7169 0.2535 1.0000 Uiso . . . . . . .
H21 H 0.6429 -0.2300 0.5816 0.0500 1.0000 Uiso . . . . . . .
H311 H 1.0794 0.8424 0.7785 0.2698 0.3257 Uiso . . . . 3 . .
H331 H 0.9620 0.8649 0.7384 0.2563 0.3257 Uiso . . . . 3 . .
H291 H 0.7799 0.4852 0.8009 0.1249 0.6743 Uiso . . . . 3 . .
H321 H 0.6612 0.5053 0.7607 0.1205 0.6743 Uiso . . . . 3 . .
H1011 H 0.6717 0.8274 0.8124 0.1249 0.3257 Uiso . . . . 3 . .
H1001 H 0.5598 0.8469 0.7724 0.1205 0.3257 Uiso . . . . 3 . .
H1031 H 0.9753 1.1809 0.7899 0.2698 0.6743 Uiso . . . . 3 . .
H1021 H 0.8585 1.2004 0.7493 0.2563 0.6743 Uiso . . . . 3 . .
H251 H 0.9305 0.8206 0.8153 0.1109 0.3257 Uiso . . . . 3 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0427(18) 0.0254(14) 0.0610(19) 0.0024(14) 0.0107(16) -0.0006(15)
O9 0.136(4) 0.071(3) 0.056(2) -0.016(2) -0.046(3) 0.019(3)
N2 0.0377(18) 0.0218(16) 0.0428(19) 0.0011(14) 0.0047(17) -0.0042(16)
C3 0.030(2) 0.0250(19) 0.041(2) -0.0021(18) 0.0018(18) -0.0014(19)
C4 0.042(2) 0.035(2) 0.041(2) -0.0002(19) 0.000(2) 0.006(2)
C5 0.035(2) 0.034(2) 0.0330(19) -0.0053(18) -0.0005(18) 0.003(2)
C6 0.034(2) 0.031(2) 0.0316(19) -0.0028(17) -0.0017(18) 0.0003(19)
C7 0.034(2) 0.030(2) 0.041(2) -0.0001(19) -0.0016(19) 0.003(2)
C8 0.037(2) 0.030(2) 0.039(2) -0.0029(19) -0.0024(18) 0.001(2)
C10 0.035(2) 0.0305(19) 0.0322(19) -0.0021(17) -0.0012(18) -0.0028(19)
C11 0.054(3) 0.039(2) 0.047(2) -0.001(2) 0.003(2) -0.002(2)
C12 0.033(2) 0.052(3) 0.053(3) -0.007(2) 0.002(2) 0.001(2)
C13 0.040(2) 0.078(4) 0.042(2) -0.014(3) 0.001(2) -0.013(3)
C14 0.039(2) 0.038(2) 0.045(2) -0.003(2) -0.004(2) 0.005(2)
C15 0.045(2) 0.042(2) 0.038(2) 0.002(2) 0.002(2) 0.003(2)
C16 0.056(3) 0.045(3) 0.046(2) 0.003(2) -0.010(2) -0.010(3)
C17 0.046(3) 0.054(3) 0.060(3) -0.017(3) -0.018(2) 0.007(3)
C18 0.046(3) 0.059(3) 0.051(3) -0.016(3) 0.015(2) -0.010(3)
C19 0.064(3) 0.055(3) 0.049(3) -0.004(3) -0.011(3) -0.011(3)
C20 0.065(3) 0.045(3) 0.039(2) -0.002(2) 0.010(2) -0.013(3)
C21 0.070(3) 0.053(3) 0.044(2) 0.001(2) -0.004(3) 0.004(3)
C22 0.073(4) 0.051(3) 0.045(3) 0.009(2) 0.005(3) -0.002(3)
C23 0.100(5) 0.059(3) 0.069(3) -0.016(3) -0.039(4) 0.017(4)
C24 0.092(4) 0.058(3) 0.069(3) -0.014(3) -0.039(3) 0.003(4)
C25 0.141(7) 0.089(5) 0.053(3) -0.002(4) -0.029(4) -0.028(5)
C26 0.169(8) 0.096(5) 0.065(4) -0.033(4) -0.060(5) 0.047(6)
C27 0.186(9) 0.090(5) 0.058(4) -0.024(4) -0.070(5) 0.028(6)
C28 0.39(2) 0.142(8) 0.112(6) -0.074(6) -0.157(10) 0.132(12)
C29 0.143(11) 0.139(12) 0.056(6) 0.007(7) -0.004(7) -0.010(10)
C31 0.30(2) 0.181(19) 0.087(8) 0.032(10) -0.086(11) -0.14(2)
C32 0.105(9) 0.131(10) 0.088(7) -0.011(8) -0.041(7) -0.022(9)
C33 0.44(3) 0.154(16) 0.076(8) 0.033(10) -0.093(13) -0.12(2)
C102 0.44(3) 0.154(16) 0.076(8) 0.033(10) -0.093(13) -0.12(2)
C101 0.143(11) 0.139(12) 0.056(6) 0.007(7) -0.004(7) -0.010(10)
C100 0.105(9) 0.131(10) 0.088(7) -0.011(8) -0.041(7) -0.022(9)
C103 0.30(2) 0.181(19) 0.087(8) 0.032(10) -0.086(11) -0.14(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.919(5)
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 . C6 . 1.247(5) yes
O9 . C26 . 1.434(7) yes
O9 . C28 . 1.343(9) yes
N2 . C3 . 1.447(5) yes
N2 . C6 . 1.347(5) yes
N2 . H21 . 0.952 no
C3 . C7 . 1.523(5) yes
C3 . C14 . 1.527(6) yes
C3 . H31 . 1.013 no
C4 . C5 . 1.380(6) yes
C4 . C12 . 1.381(6) yes
C4 . H41 . 1.032 no
C5 . C8 . 1.510(6) yes
C5 . C15 . 1.403(6) yes
C6 . C10 . 1.516(6) yes
C7 . C11 . 1.390(6) yes
C7 . C16 . 1.380(6) yes
C8 . C10 . 1.552(6) yes
C8 . C17 . 1.507(6) yes
C8 . H81 . 1.023 no
C10 . C13 . 1.515(6) yes
C10 . H101 . 1.027 no
C11 . C22 . 1.386(6) yes
C11 . H111 . 1.011 no
C12 . C18 . 1.382(7) yes
C12 . H121 . 1.025 no
C13 . H131 . 1.008 no
C13 . H132 . 0.998 no
C13 . H133 . 1.010 no
C14 . H141 . 1.005 no
C14 . H142 . 0.996 no
C14 . H143 . 0.998 no
C15 . C20 . 1.382(7) yes
C15 . H151 . 1.014 no
C16 . C19 . 1.386(6) yes
C16 . H161 . 0.997 no
C17 . C23 . 1.259(7) yes
C17 . H171 . 1.018 no
C18 . C20 . 1.374(7) yes
C18 . H181 . 1.024 no
C19 . C21 . 1.380(7) yes
C19 . H191 . 1.014 no
C20 . H201 . 1.012 no
C21 . C22 . 1.386(7) yes
C21 . H211 . 1.022 no
C22 . H221 . 1.000 no
C23 . C24 . 1.498(7) yes
C23 . H231 . 1.038 no
C24 . C26 . 1.528(9) yes
C24 . H241 . 1.032 no
C24 . H242 . 0.995 no
C25 . C29 . 1.377(8) yes
C25 . C31 . 1.383(10) yes
C25 . C101 . 1.365(9) yes
C25 . C103 . 1.364(9) yes
C25 . H251 . 0.946 no
C26 . H261 . 0.998 no
C26 . H262 . 1.019 no
C27 . C28 . 1.496(9) yes
C27 . C32 . 1.372(8) yes
C27 . C33 . 1.388(10) yes
C27 . C102 . 1.387(9) yes
C27 . C100 . 1.366(9) yes
C28 . H281 . 0.997 no
C28 . H282 . 1.057 no
C29 . C32 . 1.380(8) yes
C29 . H291 . 0.961 no
C31 . C33 . 1.391(10) yes
C31 . H311 . 0.968 no
C32 . H321 . 0.989 no
C33 . H331 . 0.976 no
C102 . C103 . 1.398(9) yes
C102 . H1021 . 0.960 no
C101 . C100 . 1.371(9) yes
C101 . H1011 . 0.960 no
C100 . H1001 . 0.969 no
C103 . H1031 . 0.983 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
C26 . O9 . C28 . 113.0(6) yes
C3 . N2 . C6 . 122.8(3) yes
C3 . N2 . H21 . 118.4 no
C6 . N2 . H21 . 117.5 no
N2 . C3 . C7 . 113.1(3) yes
N2 . C3 . C14 . 108.4(3) yes
C7 . C3 . C14 . 110.7(3) yes
N2 . C3 . H31 . 108.6 no
C7 . C3 . H31 . 106.1 no
C14 . C3 . H31 . 109.8 no
C5 . C4 . C12 . 121.8(4) yes
C5 . C4 . H41 . 119.7 no
C12 . C4 . H41 . 118.5 no
C4 . C5 . C8 . 120.7(4) yes
C4 . C5 . C15 . 117.5(4) yes
C8 . C5 . C15 . 121.8(4) yes
N2 . C6 . O1 . 122.5(4) yes
N2 . C6 . C10 . 114.7(4) yes
O1 . C6 . C10 . 122.7(4) yes
C3 . C7 . C11 . 120.0(4) yes
C3 . C7 . C16 . 121.5(4) yes
C11 . C7 . C16 . 118.4(4) yes
C5 . C8 . C10 . 111.1(3) yes
C5 . C8 . C17 . 111.3(4) yes
C10 . C8 . C17 . 111.5(4) yes
C5 . C8 . H81 . 108.8 no
C10 . C8 . H81 . 106.1 no
C17 . C8 . H81 . 107.8 no
C8 . C10 . C6 . 111.5(3) yes
C8 . C10 . C13 . 112.9(4) yes
C6 . C10 . C13 . 107.0(3) yes
C8 . C10 . H101 . 103.2 no
C6 . C10 . H101 . 111.0 no
C13 . C10 . H101 . 111.4 no
C7 . C11 . C22 . 121.6(5) yes
C7 . C11 . H111 . 118.6 no
C22 . C11 . H111 . 119.7 no
C4 . C12 . C18 . 119.6(4) yes
C4 . C12 . H121 . 120.1 no
C18 . C12 . H121 . 120.2 no
C10 . C13 . H131 . 110.7 no
C10 . C13 . H132 . 110.0 no
H131 . C13 . H132 . 109.0 no
C10 . C13 . H133 . 110.3 no
H131 . C13 . H133 . 108.0 no
H132 . C13 . H133 . 108.9 no
C3 . C14 . H141 . 109.5 no
C3 . C14 . H142 . 109.8 no
H141 . C14 . H142 . 109.4 no
C3 . C14 . H143 . 108.9 no
H141 . C14 . H143 . 109.3 no
H142 . C14 . H143 . 110.0 no
C5 . C15 . C20 . 121.1(4) yes
C5 . C15 . H151 . 119.0 no
C20 . C15 . H151 . 120.0 no
C7 . C16 . C19 . 120.7(4) yes
C7 . C16 . H161 . 118.7 no
C19 . C16 . H161 . 120.6 no
C8 . C17 . C23 . 132.5(5) yes
C8 . C17 . H171 . 114.6 no
C23 . C17 . H171 . 112.9 no
C12 . C18 . C20 . 120.1(4) yes
C12 . C18 . H181 . 119.8 no
C20 . C18 . H181 . 120.1 no
C16 . C19 . C21 . 120.3(5) yes
C16 . C19 . H191 . 119.1 no
C21 . C19 . H191 . 120.6 no
C15 . C20 . C18 . 119.9(4) yes
C15 . C20 . H201 . 119.3 no
C18 . C20 . H201 . 120.8 no
C19 . C21 . C22 . 120.0(4) yes
C19 . C21 . H211 . 119.7 no
C22 . C21 . H211 . 120.3 no
C11 . C22 . C21 . 118.9(5) yes
C11 . C22 . H221 . 121.5 no
C21 . C22 . H221 . 119.5 no
C17 . C23 . C24 . 128.2(6) yes
C17 . C23 . H231 . 114.0 no
C24 . C23 . H231 . 117.7 no
C23 . C24 . C26 . 110.9(5) yes
C23 . C24 . H241 . 109.5 no
C26 . C24 . H241 . 106.9 no
C23 . C24 . H242 . 112.1 no
C26 . C24 . H242 . 109.9 no
H241 . C24 . H242 . 107.4 no
C29 . C25 . C31 . 92.2(9) yes
C29 . C25 . C101 . 56.9(6) yes
C31 . C25 . C101 . 120.8(14) yes
C29 . C25 . C103 . 119.6(8) yes
C31 . C25 . C103 . 57.2(7) yes
C101 . C25 . C103 . 93.2(9) yes
C29 . C25 . H251 . 121.3 no
C31 . C25 . H251 . 119.3 no
C101 . C25 . H251 . 119.9 no
C103 . C25 . H251 . 119.1 no
C24 . C26 . O9 . 107.8(6) yes
C24 . C26 . H261 . 111.1 no
O9 . C26 . H261 . 110.9 no
C24 . C26 . H262 . 108.3 no
O9 . C26 . H262 . 110.5 no
H261 . C26 . H262 . 108.1 no
C28 . C27 . C32 . 120.0(9) yes
C28 . C27 . C33 . 124.1(14) yes
C32 . C27 . C33 . 91.5(9) yes
C28 . C27 . C102 . 121.6(9) yes
C32 . C27 . C102 . 118.3(8) yes
C33 . C27 . C102 . 55.9(7) yes
C28 . C27 . C100 . 119.5(11) yes
C32 . C27 . C100 . 56.3(6) yes
C33 . C27 . C100 . 116.5(14) yes
C102 . C27 . C100 . 90.6(8) yes
C27 . C28 . O9 . 111.7(7) yes
C27 . C28 . H281 . 109.0 no
O9 . C28 . H281 . 113.5 no
C27 . C28 . H282 . 106.2 no
O9 . C28 . H282 . 110.7 no
H281 . C28 . H282 . 105.3 no
C25 . C29 . C32 . 121.5(10) yes
C25 . C29 . H291 . 118.4 no
C32 . C29 . H291 . 120.1 no
C25 . C31 . C33 . 118(2) yes
C25 . C31 . H311 . 120.6 no
C33 . C31 . H311 . 120.4 no
C29 . C32 . C27 . 120.0(9) yes
C29 . C32 . H321 . 119.9 no
C27 . C32 . H321 . 120.1 no
C31 . C33 . C27 . 122(2) yes
C31 . C33 . H331 . 118.9 no
C27 . C33 . H331 . 118.3 no
C27 . C102 . C103 . 121.7(11) yes
C27 . C102 . H1021 . 118.4 no
C103 . C102 . H1021 . 119.8 no
C25 . C101 . C100 . 119.0(16) yes
C25 . C101 . H1011 . 120.0 no
C100 . C101 . H1011 . 120.4 no
C101 . C100 . C27 . 123.4(16) yes
C101 . C100 . H1001 . 118.6 no
C27 . C100 . H1001 . 117.3 no
C102 . C103 . C25 . 118.9(11) yes
C102 . C103 . H1031 . 120.2 no
C25 . C103 . H1031 . 120.9 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
C26 . H261 . C101 3_646 145 1.00 2.57 3.439(10) yes
N2 . H21 . O1 1_545 168 0.95 2.12 3.059(10) yes
C33 . H331 . C103 3_746 127 0.98 2.36 3.048(10) yes
C102 . H1021 . C31 3_756 139 0.96 2.16 2.958(10) yes