# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Gunther Brunklaus'
_publ_contact_author_email       BRUNKLAUS@MPIP-MAINZ.MPG.DE

_publ_section_title              
;
PROBING ATOMIC LEVEL STRUCTURAL TRANSFORMATION
IN O-H---N HETEROSYNTHON CRYSTAL
;
_publ_contact_author_address     
;
Max-Planck-Institute for Polymer Research
Ackermannweg 10
D-55021 Mainz
Germany
;
_publ_contact_author_fax         '+49 379100'

_publ_contact_author_phone       '+49 379133'
loop_
_publ_author_name
'Gunther Brunklaus'
'Volker Enkelmann'
'Mujeeb Khan'

# Attachment 'khan14.cif'

data_CRYSTALS_cif
_database_code_depnum_ccdc_archive 'CCDC 710270'
_audit_creation_date             09-01-15
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title 'Khan_x1 teilumgesetzt 120K 06-07'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.9360(4)
_cell_length_b                   9.8340(5)
_cell_length_c                   10.9160(5)
_cell_angle_alpha                93.0700(12)
_cell_angle_beta                 106.7800(13)
_cell_angle_gamma                113.5611(13)
_cell_volume                     733.66(6)

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C18 H16 N2 O2
# Dc = 1.32 Fooo = 308.00 Mu = 0.88 M = 292.34
# Found Formula = C18 H16 N2 O2
# Dc = 1.32 FOOO = 308.00 Mu = 0.88 M = 292.34

_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_compound_source        ?
_chemical_formula_weight         292.34

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    120

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.13
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_max          0.39

_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.088

# Sheldrick geometric approximatio 0.98 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_absorpt_correction_T_min  0.90
_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_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      120
_diffrn_reflns_number            12245
_reflns_number_total             3779
_diffrn_reflns_av_R_equivalents  0.045
# Number of reflections with Friedels Law is 3779
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3900

_diffrn_reflns_theta_min         4.079
_diffrn_reflns_theta_max         28.995
_diffrn_measured_fraction_theta_max 0.969

_diffrn_reflns_theta_full        25.225
_diffrn_measured_fraction_theta_full 0.990

_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_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         -0.30
_refine_diff_density_max         0.44

_refine_ls_number_reflns         2050
_refine_ls_number_restraints     5
_refine_ls_number_parameters     194

#_refine_ls_R_factor_ref 0.0672
_refine_ls_wR_factor_ref         0.0214
_refine_ls_goodness_of_fit_ref   1.1864

#_reflns_number_all 3779
_refine_ls_R_factor_all          0.1338
_refine_ls_wR_factor_all         0.0346

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2050
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_gt          0.0214

_refine_ls_shift/su_max          0.016796

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

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
2.73 -8.79 0.158
;

#_publ_section_title
# Title of paper - generally just the systematic or trivial name
#; ?
#;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.
#loop_
# _publ_author_name
# _publ_author_address
# _publ_author_footnote
# 'Other, Anthony N.' # Author 1
#;
# ? # Address for author 1
#;
#;
# ? # Footnote for author 1
#;
# 'Else, S. O.' # Author 2
#;
# ? # Address 2
#;
#;
# ? # 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_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 Fih.
#;
#?
#;
#_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.

#;

#_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
#;
#?
#;

# PROCESSING SUMMARY (IUCr Office Use Only):
#_journal_date_recd_electronic ?
#_journal_date_to_coeditor ?
#_journal_date_from_coeditor ?
#_journal_date_accepted ?
#_journal_date_printers_first ?
#_journal_date_printers_final ?
#_journal_date_proofs_out ?
#_journal_date_proofs_in ?
#_journal_coeditor_name ?
#_journal_coeditor_code ?
#_journal_coeditor_notes ?
#_journal_techeditor_code ?
#_journal_techeditor_notes ?
#_journal_coden_ASTM ?
#_journal_name_full ?
#_journal_year ?
#_journal_volume ?
#_journal_issue ?
#_journal_page_first ?
#_journal_page_last ?
#_journal_suppl_publ_number ?
#_journal_suppl_publ_pages ?
#
# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Blessing, SORTAV ( )

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

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.

Sheldrick, G.M. (1986). SHELXS86. Program for the solution of
crystal structures. Univ. of Göttingen, Federal Republic of Germany.

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
_atom_site_attached_hydrogens
N11 N 0.2459(3) 0.75539(19) 0.43254(17) 0.0374 1.0000 Uani . . . . . .
N12 N 0.3265(2) 0.34793(18) -0.33493(17) 0.0337 1.0000 Uani . . . . . .
C1 C -0.1477(3) 0.8088(2) 0.6601(2) 0.0299 1.0000 Uani . . . . . .
C3 C 0.1870(3) 0.84577(17) 0.72265(18) 0.0262 1.0000 Uani . . . . . .
C13 C 0.2506(3) 0.6605(2) 0.18718(19) 0.0314 1.0000 Uani D . . . . .
C18 C 0.2626(3) 0.4386(2) -0.1103(2) 0.0367 1.0000 Uani D . . . . .
O1 O -0.32645(19) 0.76858(15) 0.56868(15) 0.0383 1.0000 Uani . . . . . .
O2 O 0.34193(19) 0.84276(14) 0.69449(13) 0.0319 1.0000 Uani . . . . . .
C2 C 0.0074(3) 0.80620(19) 0.62682(18) 0.0267 1.0000 Uani . . . . . .
C4 C 0.2116(3) 0.8898(2) 0.85243(18) 0.0318 1.0000 Uani . . . . . .
C5 C 0.0564(3) 0.8931(2) 0.8835(2) 0.0340 1.0000 Uani . . . . . .
C6 C -0.1237(3) 0.8530(2) 0.7894(2) 0.0337 1.0000 Uani . . . . . .
C11 C 0.1825(3) 0.6085(2) 0.3825(2) 0.0368 1.0000 Uani . . . . . .
C12 C 0.1817(3) 0.5575(2) 0.26393(18) 0.0302 1.0000 Uani . . . . . .
C14 C 0.3139(3) 0.81262(19) 0.23772(18) 0.0303 1.0000 Uani . . . . . .
C15 C 0.3086(3) 0.8550(2) 0.3578(2) 0.0334 1.0000 Uani . . . . . .
C19 C 0.2094(3) 0.2876(2) -0.1564(2) 0.0361 1.0000 Uani . . . . . .
C20 C 0.2426(3) 0.2469(2) -0.2667(2) 0.0350 1.0000 Uani . . . . . .
C21 C 0.3789(3) 0.4929(2) -0.2911(2) 0.0385 1.0000 Uani . . . . . .
C22 C 0.3497(3) 0.5419(2) -0.18218(19) 0.0397 1.0000 Uani . . . . . .
C16 C 0.2813(3) 0.6190(2) 0.0637(2) 0.0279 0.8529 Uani . . . . . .
C17 C 0.2352(3) 0.4806(2) 0.0073(2) 0.0279 0.8529 Uani . . . . . .
C26 C 0.1235(17) 0.6025(13) 0.0505(12) 0.0279 0.1471 Uani D . . . . .
C27 C 0.1066(18) 0.4480(13) -0.0045(12) 0.0279 0.1471 Uani D . . . . .
H21 H -0.0095 0.7768 0.5381 0.0342 1.0000 Uiso R . . . . .
H41 H 0.3338 0.9170 0.9187 0.0392 1.0000 Uiso R . . . . .
H51 H 0.0739 0.9240 0.9720 0.0425 1.0000 Uiso R . . . . .
H61 H -0.2291 0.8557 0.8125 0.0417 1.0000 Uiso R . . . . .
H111 H 0.1367 0.5363 0.4338 0.0458 1.0000 Uiso R . . . . .
H121 H 0.1336 0.4522 0.2331 0.0395 1.0000 Uiso R . . . . .
H141 H 0.3604 0.8866 0.1880 0.0410 1.0000 Uiso R . . . . .
H151 H 0.3515 0.9593 0.3896 0.0432 1.0000 Uiso R . . . . .
H191 H 0.1497 0.2122 -0.1118 0.0450 1.0000 Uiso R . . . . .
H201 H 0.2065 0.1432 -0.2958 0.0446 1.0000 Uiso R . . . . .
H211 H 0.4389 0.5651 -0.3379 0.0468 1.0000 Uiso R . . . . .
H221 H 0.3899 0.6467 -0.1550 0.0482 1.0000 Uiso R . . . . .
H161 H 0.3385 0.6985 0.0217 0.0367 0.8529 Uiso R . . . . .
H171 H 0.1790 0.4018 0.0503 0.0367 0.8529 Uiso R . . . . .
H261 H 0.1725 0.6751 0.0003 0.0367 0.1471 Uiso R . . . . .
H271 H 0.1430 0.4050 0.0688 0.0367 0.1471 Uiso R . . . . .
H1 H -0.3264 0.7283 0.4876 0.0497 1.0000 Uiso R . . . . .
H2 H 0.3086 0.8124 0.6033 0.0437 1.0000 Uiso R . . . . .
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
N11 0.0459(10) 0.0387(9) 0.0368(10) 0.0135(8) 0.0221(9) 0.0211(8)
N12 0.0249(8) 0.0321(9) 0.0334(10) 0.0072(7) -0.0003(7) 0.0088(7)
C1 0.0353(11) 0.0200(10) 0.0354(12) 0.0082(9) 0.0137(10) 0.0114(8)
C3 0.0303(11) 0.0140(9) 0.0301(11) 0.0073(8) 0.0101(9) 0.0051(7)
C13 0.0346(12) 0.0263(10) 0.0272(11) 0.0073(8) 0.0053(9) 0.0107(8)
C18 0.0477(13) 0.0253(10) 0.0249(11) 0.0029(8) -0.0019(10) 0.0140(9)
O1 0.0303(8) 0.0426(9) 0.0412(9) 0.0089(7) 0.0121(7) 0.0151(6)
O2 0.0301(7) 0.0296(7) 0.0329(8) 0.0102(6) 0.0110(6) 0.0093(6)
C2 0.0316(10) 0.0198(9) 0.0227(9) 0.0062(7) 0.0078(8) 0.0060(7)
C4 0.0409(12) 0.0203(9) 0.0247(11) 0.0054(7) 0.0058(9) 0.0076(8)
C5 0.0559(14) 0.0220(10) 0.0245(10) 0.0064(8) 0.0173(9) 0.0144(9)
C6 0.0453(13) 0.0240(10) 0.0417(12) 0.0096(9) 0.0258(11) 0.0166(9)
C11 0.0391(12) 0.0331(11) 0.0442(13) 0.0180(10) 0.0203(10) 0.0160(9)
C12 0.0288(10) 0.0264(10) 0.0317(11) 0.0093(9) 0.0062(8) 0.0107(8)
C14 0.0314(10) 0.0230(9) 0.0308(11) 0.0086(8) 0.0070(9) 0.0085(8)
C15 0.0293(10) 0.0275(9) 0.0418(12) 0.0067(9) 0.0119(9) 0.0110(8)
C19 0.0376(12) 0.0232(10) 0.0350(11) 0.0065(8) 0.0044(9) 0.0062(8)
C20 0.0305(10) 0.0251(10) 0.0392(13) 0.0063(9) 0.0032(9) 0.0082(8)
C21 0.0332(12) 0.0332(11) 0.0347(12) 0.0102(9) -0.0015(9) 0.0089(9)
C22 0.0430(13) 0.0223(9) 0.0386(13) 0.0085(9) -0.0005(10) 0.0090(9)
C16 0.0337(4) 0.0249(4) 0.0257(4) 0.0111(4) 0.0120(4) 0.0112(4)
C17 0.0337(4) 0.0249(4) 0.0257(4) 0.0111(4) 0.0120(4) 0.0112(4)
C26 0.0337(4) 0.0249(4) 0.0257(4) 0.0111(4) 0.0120(4) 0.0112(4)
C27 0.0337(4) 0.0249(4) 0.0257(4) 0.0111(4) 0.0120(4) 0.0112(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.095(8)
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
N11 . C11 . 1.347(3) yes
N11 . C15 . 1.343(2) yes
N12 . C20 . 1.350(2) yes
N12 . C21 . 1.331(2) yes
C1 . O1 . 1.363(2) yes
C1 . C2 . 1.389(3) yes
C1 . C6 . 1.390(3) yes
C3 . O2 . 1.362(2) yes
C3 . C2 . 1.389(2) yes
C3 . C4 . 1.393(3) yes
C13 . C12 . 1.393(2) yes
C13 . C14 . 1.394(3) yes
C13 . C16 . 1.501(3) yes
C13 . C26 . 1.466(12) yes
C18 . C19 . 1.390(3) yes
C18 . C22 . 1.401(3) yes
C18 . C17 . 1.429(3) yes
O1 . H1 . 0.950 no
O2 . H2 . 0.950 no
C2 . H21 . 0.950 no
C4 . C5 . 1.380(3) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.382(3) yes
C5 . H51 . 0.950 no
C6 . H61 . 0.950 no
C11 . C12 . 1.360(3) yes
C11 . H111 . 0.950 no
C12 . H121 . 0.950 no
C14 . C15 . 1.372(3) yes
C14 . H141 . 0.950 no
C15 . H151 . 0.950 no
C19 . C20 . 1.377(3) yes
C19 . H191 . 0.950 no
C20 . H201 . 0.950 no
C21 . C22 . 1.373(3) yes
C21 . H211 . 0.950 no
C22 . H221 . 0.950 no
C16 . C17 . 1.322(3) yes
C16 . C26 . 1.160(12) yes
C16 . C27 . 1.647(12) yes
C16 . H161 . 0.950 no
C16 . H261 . 1.267 no
C17 . C27 . 0.904(12) yes
C17 . H171 . 0.950 no
C17 . H271 . 1.200 no
C26 . C27 2_565 1.598(16) yes
C26 . C27 . 1.543(17) yes
C26 . H261 . 0.950 no
C27 . H171 . 0.966 no
C27 . H271 . 0.950 no
H171 . H271 . 0.404 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
C11 . N11 . C15 . 116.60(18) yes
C20 . N12 . C21 . 117.17(19) yes
O1 . C1 . C2 . 121.77(19) yes
O1 . C1 . C6 . 117.97(18) yes
C2 . C1 . C6 . 120.27(19) yes
O2 . C3 . C2 . 122.21(19) yes
O2 . C3 . C4 . 118.16(17) yes
C2 . C3 . C4 . 119.6(2) yes
C12 . C13 . C14 . 116.61(19) yes
C12 . C13 . C16 . 123.86(17) yes
C14 . C13 . C16 . 119.12(18) yes
C12 . C13 . C26 . 110.1(5) yes
C14 . C13 . C26 . 117.8(5) yes
C16 . C13 . C26 . 46.0(5) yes
C19 . C18 . C22 . 116.0(2) yes
C19 . C18 . C17 . 119.9(2) yes
C22 . C18 . C17 . 124.09(18) yes
C1 . O1 . H1 . 108.6 no
C3 . O2 . H2 . 110.6 no
C1 . C2 . C3 . 120.31(19) yes
C1 . C2 . H21 . 119.9 no
C3 . C2 . H21 . 119.8 no
C3 . C4 . C5 . 119.25(19) yes
C3 . C4 . H41 . 120.3 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C6 . 121.9(2) yes
C4 . C5 . H51 . 119.1 no
C6 . C5 . H51 . 119.1 no
C1 . C6 . C5 . 118.7(2) yes
C1 . C6 . H61 . 120.5 no
C5 . C6 . H61 . 120.8 no
N11 . C11 . C12 . 124.09(18) yes
N11 . C11 . H111 . 117.7 no
C12 . C11 . H111 . 118.2 no
C13 . C12 . C11 . 119.56(17) yes
C13 . C12 . H121 . 120.0 no
C11 . C12 . H121 . 120.4 no
C13 . C14 . C15 . 120.35(18) yes
C13 . C14 . H141 . 119.4 no
C15 . C14 . H141 . 120.3 no
C14 . C15 . N11 . 122.76(18) yes
C14 . C15 . H151 . 118.7 no
N11 . C15 . H151 . 118.6 no
C18 . C19 . C20 . 120.21(19) yes
C18 . C19 . H191 . 120.0 no
C20 . C19 . H191 . 119.8 no
C19 . C20 . N12 . 123.03(18) yes
C19 . C20 . H201 . 118.8 no
N12 . C20 . H201 . 118.2 no
N12 . C21 . C22 . 123.1(2) yes
N12 . C21 . H211 . 118.0 no
C22 . C21 . H211 . 119.0 no
C18 . C22 . C21 . 120.53(19) yes
C18 . C22 . H221 . 119.8 no
C21 . C22 . H221 . 119.7 no
C13 . C16 . C17 . 125.71(19) yes
C13 . C16 . C26 . 65.4(6) yes
C17 . C16 . C26 . 97.1(6) yes
C13 . C16 . C27 . 105.6(5) yes
C17 . C16 . C27 . 33.2(4) yes
C26 . C16 . C27 . 64.0(7) yes
C13 . C16 . H161 . 117.7 no
C17 . C16 . H161 . 116.6 no
C26 . C16 . H161 . 108.6 no
C27 . C16 . H161 . 127.9 no
C13 . C16 . H261 . 91.2 no
C17 . C16 . H261 . 113.1 no
C26 . C16 . H261 . 45.8 no
C27 . C16 . H261 . 89.8 no
H161 . C16 . H261 . 63.0 no
C18 . C17 . C16 . 126.6(2) yes
C18 . C17 . C27 . 110.8(8) yes
C16 . C17 . C27 . 93.5(8) yes
C18 . C17 . H171 . 117.3 no
C16 . C17 . H171 . 116.1 no
C27 . C17 . H171 . 62.7 no
C18 . C17 . H271 . 130.7 no
C16 . C17 . H271 . 101.9 no
C27 . C17 . H271 . 51.4 no
H171 . C17 . H271 . 17.1 no
C27 2_565 C26 . C13 . 122.8(9) yes
C27 2_565 C26 . C16 . 167.2(11) yes
C13 . C26 . C16 . 68.6(6) yes
C27 2_565 C26 . C27 . 95.3(10) yes
C13 . C26 . C27 . 113.0(9) yes
C16 . C26 . C27 . 73.5(8) yes
C27 2_565 C26 . H261 . 106.0 no
C13 . C26 . H261 . 108.5 no
C16 . C26 . H261 . 73.0 no
C27 . C26 . H261 . 110.3 no
C26 . C27 . C26 2_565 84.7(10) yes
C26 . C27 . C16 . 42.5(5) yes
C26 2_565 C27 . C16 . 126.9(9) yes
C26 . C27 . C17 . 95.6(10) yes
C26 2_565 C27 . C17 . 169.9(12) yes
C16 . C27 . C17 . 53.2(6) yes
C26 . C27 . H171 . 119.6 no
C26 2_565 C27 . H171 . 127.5 no
C16 . C27 . H171 . 92.0 no
C17 . C27 . H171 . 61.0 no
C26 . C27 . H271 . 106.2 no
C26 2_565 C27 . H271 . 109.1 no
C16 . C27 . H271 . 94.1 no
C17 . C27 . H271 . 80.6 no
H171 . C27 . H271 . 24.3 no
C27 . H171 . C17 . 56.3 no
C27 . H171 . H271 . 75.7 no
C17 . H171 . H271 . 119.2 no
C26 . H261 . C16 . 61.1 no
C17 . H271 . C27 . 48.0 no
C17 . H271 . H171 . 43.7 no
C27 . H271 . H171 . 80.0 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
O1 . H1 . N12 2_565 180 0.95 1.79 2.740(2) yes
O2 . H2 . N11 . 180 0.95 1.78 2.730(2) yes

# Attachment 'khan42.cif'

data_CRYSTALS_cif2
_database_code_depnum_ccdc_archive 'CCDC 710271'
_audit_creation_date             09-01-15
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title 'Khanx1 irrad 120K 02-07'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.7682(4)
_cell_length_b                   9.7938(5)
_cell_length_c                   11.0478(5)
_cell_angle_alpha                94.4493(12)
_cell_angle_beta                 104.8507(13)
_cell_angle_gamma                111.4950(13)
_cell_volume                     742.07(6)

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C18 H16 N2 O2
# Dc = 1.31 Fooo = 308.00 Mu = 0.87 M = 292.34
# Found Formula = C18 H16 N2 O2
# Dc = 1.31 FOOO = 308.00 Mu = 0.87 M = 292.34

_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_compound_source        ?
_chemical_formula_weight         292.34

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    120

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_max          0.33

_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.087

# Sheldrick geometric approximatio 0.98 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_absorpt_correction_T_min  0.88
_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_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      120
_diffrn_reflns_number            13514
_reflns_number_total             3357
_diffrn_reflns_av_R_equivalents  0.067
# Number of reflections with Friedels Law is 3357
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3401

_diffrn_reflns_theta_min         4.101
_diffrn_reflns_theta_max         27.491
_diffrn_measured_fraction_theta_max 0.784

_diffrn_reflns_theta_full        25.017
_diffrn_measured_fraction_theta_full 0.823

_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -10
_reflns_limit_h_max              9
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_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         -0.34
_refine_diff_density_max         0.29

_refine_ls_number_reflns         2100
_refine_ls_number_restraints     0
_refine_ls_number_parameters     217

#_refine_ls_R_factor_ref 0.0528
_refine_ls_wR_factor_ref         0.0561
_refine_ls_goodness_of_fit_ref   0.8852

#_reflns_number_all 2672
_refine_ls_R_factor_all          0.0542
_refine_ls_wR_factor_all         0.0574

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>1.5σ(I)
_reflns_number_gt                2100
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_gt          0.0561

_refine_ls_shift/su_max          0.003586

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

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
1.48 1.45 0.459
;

#_publ_section_title
# Title of paper - generally just the systematic or trivial name
#; ?
#;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.
#loop_
# _publ_author_name
# _publ_author_address
# _publ_author_footnote
# 'Other, Anthony N.' # Author 1
#;
# ? # Address for author 1
#;
#;
# ? # Footnote for author 1
#;
# 'Else, S. O.' # Author 2
#;
# ? # Address 2
#;
#;
# ? # 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_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 Fih.
#;
#?
#;
#_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.

#;

#_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
#;
#?
#;

# PROCESSING SUMMARY (IUCr Office Use Only):
#_journal_date_recd_electronic ?
#_journal_date_to_coeditor ?
#_journal_date_from_coeditor ?
#_journal_date_accepted ?
#_journal_date_printers_first ?
#_journal_date_printers_final ?
#_journal_date_proofs_out ?
#_journal_date_proofs_in ?
#_journal_coeditor_name ?
#_journal_coeditor_code ?
#_journal_coeditor_notes ?
#_journal_techeditor_code ?
#_journal_techeditor_notes ?
#_journal_coden_ASTM ?
#_journal_name_full ?
#_journal_year ?
#_journal_volume ?
#_journal_issue ?
#_journal_page_first ?
#_journal_page_last ?
#_journal_suppl_publ_number ?
#_journal_suppl_publ_pages ?
#
# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Blessing, SORTAV ( )

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

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.

Sheldrick, G.M. (1986). SHELXS86. Program for the solution of
crystal structures. Univ. of Göttingen, Federal Republic of Germany.

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
_atom_site_attached_hydrogens
C1 C 0.3540(3) 0.8051(2) 0.6615(2) 0.0423 1.0000 Uani . . . . . .
C2 C 0.3730(4) 0.8507(2) 0.7893(2) 0.0514 1.0000 Uani . . . . . .
C3 C 0.5508(4) 0.8891(2) 0.8796(2) 0.0534 1.0000 Uani . . . . . .
C4 C 0.7115(3) 0.8871(2) 0.84933(17) 0.0437 1.0000 Uani . . . . . .
C5 C 0.6920(3) 0.84366(16) 0.72038(15) 0.0321 1.0000 Uani . . . . . .
C6 C 0.5132(3) 0.80245(16) 0.62765(15) 0.0314 1.0000 Uani . . . . . .
C11 C 0.8711(3) 0.4897(2) -0.2886(2) 0.0589 1.0000 Uani . . . . . .
C12 C 0.8369(4) 0.5361(2) -0.1799(2) 0.0673 1.0000 Uani . . . . . .
C13 C 0.7474(4) 0.4318(2) -0.11204(19) 0.0629 1.0000 Uani . . . . . .
C14 C 0.7028(3) 0.2820(2) -0.15942(19) 0.0534 1.0000 Uani . . . . . .
C15 C 0.7389(3) 0.2448(2) -0.2699(2) 0.0488 1.0000 Uani . . . . . .
C16 C 0.7433(5) 0.4759(3) 0.0013(3) 0.0419 0.5841 Uani . . . . . .
C17 C 0.7825(5) 0.6152(3) 0.0571(3) 0.0357 0.5841 Uani . . . . . .
C18 C 0.7389(3) 0.65930(19) 0.18656(16) 0.0464 1.0000 Uani . . . . . .
C19 C 0.8085(3) 0.81026(19) 0.23620(16) 0.0393 1.0000 Uani . . . . . .
C20 C 0.8201(3) 0.8562(2) 0.35904(18) 0.0427 1.0000 Uani . . . . . .
C21 C 0.6998(3) 0.6133(2) 0.3874(2) 0.0519 1.0000 Uani . . . . . .
C22 C 0.6816(3) 0.5591(2) 0.26549(18) 0.0420 1.0000 Uani . . . . . .
C26 C 0.6062(7) 0.4473(5) 0.0008(4) 0.0324 0.4159 Uani . . . . . .
C27 C 0.6257(6) 0.6051(4) 0.0538(3) 0.0301 0.4159 Uani . . . . . .
N11 N 0.8210(2) 0.34544(18) -0.33639(17) 0.0505 1.0000 Uani . . . . . .
N12 N 0.7675(3) 0.76087(19) 0.43584(16) 0.0516 1.0000 Uani . . . . . .
H21 H 0.2659 0.8550 0.8134 0.0531 1.0000 Uiso R . . . . .
H31 H 0.5622 0.9198 0.9661 0.0571 1.0000 Uiso R . . . . .
H41 H 0.8323 0.9134 0.9134 0.0515 1.0000 Uiso R . . . . .
H61 H 0.4999 0.7732 0.5406 0.0355 1.0000 Uiso R . . . . .
H111 H 0.9304 0.5627 -0.3336 0.0711 1.0000 Uiso R . . . . .
H121 H 0.8827 0.6403 -0.1487 0.0802 1.0000 Uiso R . . . . .
H141 H 0.6479 0.2066 -0.1149 0.0526 1.0000 Uiso R . . . . .
H151 H 0.7065 0.1425 -0.3008 0.0604 1.0000 Uiso R . . . . .
H161 H 0.7131 0.4012 0.0516 0.0306 0.5841 Uiso R . . . . .
H171 H 0.8424 0.6938 0.0169 0.0306 0.5841 Uiso R . . . . .
H191 H 0.8447 0.8815 0.1839 0.0476 1.0000 Uiso R . . . . .
H201 H 0.8662 0.9600 0.3918 0.0437 1.0000 Uiso R . . . . .
H211 H 0.6609 0.5445 0.4411 0.0592 1.0000 Uiso R . . . . .
H221 H 0.6293 0.4545 0.2344 0.0509 1.0000 Uiso R . . . . .
H261 H 0.6429 0.4043 0.0720 0.0306 0.4159 Uiso R . . . . .
H271 H 0.6870 0.6718 0.0050 0.0306 0.4159 Uiso R . . . . .
O1 O 0.1753(2) 0.76398(17) 0.57356(16) 0.0572 1.0000 Uani . . . . . .
O2 O 0.85341(17) 0.84151(14) 0.69283(11) 0.0380 1.0000 Uani . . . . . .
H1 H 0.1755 0.7259 0.4918 0.0600 1.0000 Uiso R . . . . .
H2 H 0.8245 0.8133 0.6033 0.0450 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0442(10) 0.0308(9) 0.0612(12) 0.0166(8) 0.0279(9) 0.0160(8)
C2 0.0740(15) 0.0369(10) 0.0706(14) 0.0231(10) 0.0543(13) 0.0285(10)
C3 0.0942(18) 0.0326(10) 0.0527(12) 0.0150(9) 0.0421(13) 0.0321(11)
C4 0.0623(13) 0.0348(9) 0.0292(9) 0.0043(7) 0.0102(8) 0.0171(9)
C5 0.0435(9) 0.0158(6) 0.0280(8) 0.0023(6) 0.0083(7) 0.0041(6)
C6 0.0457(10) 0.0225(7) 0.0240(7) 0.0032(6) 0.0156(7) 0.0081(6)
C11 0.0527(12) 0.0426(11) 0.0463(12) 0.0052(9) -0.0048(9) -0.0056(9)
C12 0.0831(17) 0.0333(10) 0.0508(13) 0.0038(9) -0.0118(12) 0.0076(11)
C13 0.0883(18) 0.0382(10) 0.0285(10) 0.0048(8) -0.0075(10) 0.0055(11)
C14 0.0691(14) 0.0270(9) 0.0407(11) 0.0072(8) -0.0106(10) 0.0118(9)
C15 0.0406(10) 0.0275(9) 0.0600(13) 0.0075(8) 0.0001(9) 0.0039(7)
C16 0.058(2) 0.0341(16) 0.0442(18) 0.0203(14) 0.0274(16) 0.0196(15)
C17 0.0445(17) 0.0280(13) 0.0272(14) 0.0047(11) 0.0078(12) 0.0087(12)
C18 0.0565(12) 0.0278(8) 0.0302(9) 0.0057(7) -0.0087(8) 0.0046(8)
C19 0.0445(10) 0.0301(8) 0.0357(9) 0.0093(7) 0.0079(8) 0.0090(7)
C20 0.0421(10) 0.0356(9) 0.0488(11) 0.0055(8) 0.0185(8) 0.0113(8)
C21 0.0592(13) 0.0465(11) 0.0668(13) 0.0247(10) 0.0430(11) 0.0211(10)
C22 0.0392(10) 0.0320(9) 0.0459(11) 0.0127(8) 0.0030(8) 0.0101(7)
C26 0.044(2) 0.035(2) 0.0234(18) 0.0084(15) 0.0131(17) 0.0192(18)
C27 0.035(2) 0.0294(19) 0.0206(17) 0.0130(15) 0.0035(15) 0.0091(16)
N11 0.0360(8) 0.0391(9) 0.0588(10) 0.0187(8) 0.0002(8) 0.0036(7)
N12 0.0726(12) 0.0451(9) 0.0555(10) 0.0154(8) 0.0453(9) 0.0255(8)
O1 0.0405(8) 0.0564(9) 0.0795(10) 0.0212(8) 0.0252(8) 0.0186(7)
O2 0.0339(6) 0.0401(7) 0.0373(7) 0.0093(5) 0.0116(5) 0.0110(5)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.194(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
C1 . C2 . 1.400(3) yes
C1 . C6 . 1.389(2) yes
C1 . O1 . 1.368(2) yes
C2 . C3 . 1.378(3) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.379(3) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.408(2) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.392(2) yes
C5 . O2 . 1.370(2) yes
C6 . H61 . 0.950 no
C11 . C12 . 1.373(3) yes
C11 . N11 . 1.343(3) yes
C11 . H111 . 0.950 no
C12 . C13 . 1.399(3) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.400(3) yes
C13 . C16 . 1.305(4) yes
C14 . C15 . 1.372(3) yes
C14 . H141 . 0.950 no
C15 . N11 . 1.345(3) yes
C15 . H151 . 0.950 no
C16 . C17 . 1.343(4) yes
C16 . C26 . 0.996(5) yes
C16 . H161 . 0.950 no
C16 . H261 . 1.307 no
C17 . C18 . 1.614(4) yes
C17 . C26 . 1.650(5) yes
C17 . C27 . 1.176(5) yes
C17 . H171 . 0.950 no
C17 . H271 . 1.149 no
C18 . C19 . 1.384(2) yes
C18 . C22 . 1.390(2) yes
C18 . C27 . 1.443(4) yes
C19 . C20 . 1.366(2) yes
C19 . H191 . 0.950 no
C20 . N12 . 1.334(2) yes
C20 . H201 . 0.950 no
C21 . C22 . 1.361(3) yes
C21 . N12 . 1.353(3) yes
C21 . H211 . 0.950 no
C22 . H221 . 0.950 no
C26 . C27 2_665 1.609(6) yes
C26 . C27 . 1.548(5) yes
C26 . H161 . 1.133 no
C26 . H261 . 0.950 no
C27 . H271 . 0.950 no
H161 . H261 . 0.651 no
O1 . H1 . 0.950 no
O2 . H2 . 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 . C1 . C6 . 120.1(2) yes
C2 . C1 . O1 . 117.69(18) yes
C6 . C1 . O1 . 122.19(18) yes
C1 . C2 . C3 . 118.51(18) yes
C1 . C2 . H21 . 120.9 no
C3 . C2 . H21 . 120.6 no
C2 . C3 . C4 . 122.84(18) yes
C2 . C3 . H31 . 117.9 no
C4 . C3 . H31 . 119.3 no
C3 . C4 . C5 . 118.3(2) yes
C3 . C4 . H41 . 121.3 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C6 . 119.89(17) yes
C4 . C5 . O2 . 117.17(16) yes
C6 . C5 . O2 . 122.94(14) yes
C5 . C6 . C1 . 120.36(16) yes
C5 . C6 . H61 . 120.0 no
C1 . C6 . H61 . 119.7 no
C12 . C11 . N11 . 123.3(2) yes
C12 . C11 . H111 . 118.7 no
N11 . C11 . H111 . 118.0 no
C11 . C12 . C13 . 120.4(2) yes
C11 . C12 . H121 . 118.9 no
C13 . C12 . H121 . 120.6 no
C12 . C13 . C14 . 116.1(2) yes
C12 . C13 . C16 . 120.3(2) yes
C14 . C13 . C16 . 122.2(2) yes
C13 . C14 . C15 . 119.86(19) yes
C13 . C14 . H141 . 119.9 no
C15 . C14 . H141 . 120.2 no
C14 . C15 . N11 . 123.73(18) yes
C14 . C15 . H151 . 118.5 no
N11 . C15 . H151 . 117.7 no
C13 . C16 . C17 . 127.8(3) yes
C13 . C16 . C26 . 109.8(4) yes
C17 . C16 . C26 . 88.4(3) yes
C13 . C16 . H161 . 116.2 no
C17 . C16 . H161 . 115.9 no
C26 . C16 . H161 . 71.2 no
C13 . C16 . H261 . 130.8 no
C17 . C16 . H261 . 97.6 no
C26 . C16 . H261 . 46.3 no
H161 . C16 . H261 . 28.3 no
C16 . C17 . C18 . 125.5(2) yes
C16 . C17 . C26 . 37.11(19) yes
C18 . C17 . C26 . 100.2(2) yes
C16 . C17 . C27 . 100.8(3) yes
C18 . C17 . C27 . 59.9(2) yes
C26 . C17 . C27 . 63.9(3) yes
C16 . C17 . H171 . 116.5 no
C18 . C17 . H171 . 118.0 no
C26 . C17 . H171 . 132.6 no
C27 . C17 . H171 . 111.1 no
C16 . C17 . H271 . 116.2 no
C18 . C17 . H271 . 89.0 no
C26 . C17 . H271 . 92.2 no
C27 . C17 . H271 . 48.2 no
H171 . C17 . H271 . 63.4 no
C17 . C18 . C19 . 116.73(17) yes
C17 . C18 . C22 . 123.58(18) yes
C19 . C18 . C22 . 117.69(17) yes
C17 . C18 . C27 . 44.8(2) yes
C19 . C18 . C27 . 118.9(2) yes
C22 . C18 . C27 . 114.0(2) yes
C18 . C19 . C20 . 120.01(16) yes
C18 . C19 . H191 . 119.8 no
C20 . C19 . H191 . 120.2 no
C19 . C20 . N12 . 122.66(17) yes
C19 . C20 . H201 . 119.3 no
N12 . C20 . H201 . 118.0 no
C22 . C21 . N12 . 123.30(17) yes
C22 . C21 . H211 . 118.7 no
N12 . C21 . H211 . 118.0 no
C18 . C22 . C21 . 118.99(17) yes
C18 . C22 . H221 . 120.4 no
C21 . C22 . H221 . 120.6 no
C27 2_665 C26 . C17 . 131.0(3) yes
C27 2_665 C26 . C16 . 159.4(4) yes
C17 . C26 . C16 . 54.5(3) yes
C27 2_665 C26 . C27 . 89.6(3) yes
C17 . C26 . C27 . 43.0(2) yes
C16 . C26 . C27 . 97.2(4) yes
C27 2_665 C26 . H161 . 138.1 no
C17 . C26 . H161 . 87.2 no
C16 . C26 . H161 . 52.5 no
C27 . C26 . H161 . 120.2 no
C27 2_665 C26 . H261 . 112.2 no
C17 . C26 . H261 . 96.4 no
C16 . C26 . H261 . 84.3 no
C27 . C26 . H261 . 107.2 no
H161 . C26 . H261 . 35.0 no
C26 . C27 . C26 2_665 90.4(3) yes
C26 . C27 . C18 . 113.7(3) yes
C26 2_665 C27 . C18 . 124.9(3) yes
C26 . C27 . C17 . 73.1(3) yes
C26 2_665 C27 . C17 . 158.5(4) yes
C18 . C27 . C17 . 75.3(3) yes
C26 . C27 . H271 . 107.6 no
C26 2_665 C27 . H271 . 109.6 no
C18 . C27 . H271 . 108.6 no
C17 . C27 . H271 . 64.4 no
C15 . N11 . C11 . 116.6(2) yes
C21 . N12 . C20 . 117.34(16) yes
C26 . H161 . C16 . 56.3 no
C26 . H161 . H261 . 56.9 no
C16 . H161 . H261 . 108.0 no
H161 . H261 . C26 . 88.0 no
H161 . H261 . C16 . 43.8 no
C26 . H261 . C16 . 49.3 no
C17 . H271 . C27 . 67.4 no
C1 . O1 . H1 . 110.7 no
C5 . O2 . H2 . 109.9 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
O1 . H1 . N11 2_665 179 0.95 1.81 2.764(2) yes
O2 . H2 . N12 . 179 0.95 1.77 2.725(2) yes


