Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001

data_global
_journal_coden_Cambridge          1145
_audit_creation_method            SHELXL

#------------------ SUBMISSION DETAILS --------------------------------------#
# Name and address of author for correspondence

_publ_contact_author_name      'Dr A D Woolhouse'
_publ_contact_author_address
;
Dr A D Woolhouse
Industrial Research Ltd
PO Box 31 310
Lower Hutt
NEW ZEALAND
;
_publ_contact_author_email       'T.WOOLHOUSE@IRL.CRI.NZ'
_publ_contact_author_fax         '64(4)5690142'
_publ_contact_author_phone       '64(4)5690815'

#--------

_publ_requested_journal          'Journal of Materials Chemistry'
_publ_contact_letter            # Include date of submission
;
Date of submission March, 2001
;
_publ_section_title
;
Simple zwitterionic merocyanines as potential NLO chromophores
;

loop_
_publ_author_name
_publ_author_address
'Kay, A. J.'
;Industrial Research Limited
PO Box 31-310
Lower Hutt
New Zealand
;
'Woolhouse, A. D.'
;Industrial Research Limited
PO Box 31-310
Lower Hutt
New Zealand
;
'Gainsford, G. J.'
;Industrial Research Limited
PO Box 31-310
Lower Hutt
New Zealand
;
'Haskell, T.G.'
;Industrial Research Limited
PO Box 31-310
Lower Hutt
New Zealand
;
'Wyss, C.P.'
;Department of Physics
University of Otago
PO Box 56
Dunedin
New Zealand
;
'Giffin, S.M.'
;Department of Physics
University of Otago
PO Box 56
Dunedin
New Zealand
;
'McKinnie, I.T.'
;Department of Physics
University of Otago
PO Box 56
Dunedin
New Zealand
;
'Barnes, T.H.'
;Department of Physics
University of Auckland
PO Box 92019
Auckland
New Zealand
;

#------------------ TEXT ----------------------------------------------------#

_publ_section_synopsis
;
SYNOPSIS for an ACTA C/E here
;
_publ_section_abstract
;
ABSTRACT for an ACTA C/E here
;

_publ_section_comment
;
COMMENT  for an ACTA C/E here
;

_publ_section_exptl_prep
;
PREPARE details here for an ACTA C/E here
;
_publ_section_exptl_refinement
;
Atoms C1 and C2 of the -CH2CH(OH)CH2OH terminal group bound to N1
were disordered between two conformations
(labelled A & B) which refined to occupancies of 0.535(4):0.465(4).
This models two alternative conformations of the two atoms C1 and C2 which
bind to the same O1 and O2 atoms.
All H atoms were constrained to an isotropic
thermal parameteer 1.2 times that of the equivalent
U of their parent atom. C-H distances used were 0.95,0.999 and 1.00\%A for
the phenyl, methylene and tertiary hydrogen atoms respectively.
;
_publ_section_references
;
ConQuest Version 1.0, Cambridge Structural Database version 5.19
(April 2000),
The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge,
U.K. CB2 1EZ.

Farrugia, L. J. (1999) WinGX - A Windows Program for Crystal Structure
Analysis, J. Appl. Cryst. 32, 837-838.

Siemens (1996). SMART and SAINT. Versions 4.0.  Siemens Analytical X-ray
Instruments Inc., Madison, Wisconsin, USA.

Sheldrick, G.M. (1996). SADABS. University of G\"ottingen, Germany.

Sheldrick, G.M. (1997) SHELXL97 and SHELXS97. University of G\"ottingen,
Germany.

SMART software (1996), Siemens Analytical X-ray Systems Inc., Madison,
Wisconsin, USA.

Spek, A.L. (1990). PLATON, Acta Cryst., A46, C34.
;

_publ_section_figure_captions
;
Fig 1.  C~17~H~16~N~2~O~4~ [Spek (1990)]
Displacement ellipsoids are drawn at the 30% probability level,
H atoms and the minor(B) conformation positions for C1 and C2
are excluded for clarity.
;

_publ_section_acknowledgements
;
We wish to thank Drs J. Wikaira, C. Richardson and Ward T. Robinson,
University of Canterbury,
for collection of the diffraction data.
;

_publ_section_table_legends
;
Table 1. Selected geometric parameters (\%A ,\% )
;

data_wffb

_database_code_CSD	164244


_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum             'C17 H16 N2 O4'
_chemical_formula_weight          312.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C'  'C'   0.0033   0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H'  'H'   0.0000   0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N'  'N'   0.0061   0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O'  'O'   0.0106   0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting            'Triclinic'
_symmetry_space_group_name_H-M    'P-1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                    7.987(2)
_cell_length_b                    10.300(3)
_cell_length_c                    10.806(3)
_cell_angle_alpha                 118.308(4)
_cell_angle_beta                  106.121(4)
_cell_angle_gamma                 94.752(4)
_cell_volume                      727.3(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     158(2)
_cell_measurement_reflns_used     5411
_cell_measurement_theta_min       2.27
_cell_measurement_theta_max       23.65

_exptl_crystal_description        block
_exptl_crystal_colour             'pale yellow'
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.56
_exptl_crystal_size_min           0.30
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.426
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              328
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.687
_exptl_absorpt_correction_T_max   1.0
#----------- these values output from SADABS
#-----TO BE? - rescaled according to 1998 acceptance standards  Tmax ??
_exptl_absorpt_process_details
;
Blessing, Acta Cryst. (1995) A57, 33-38.
;

_exptl_special_details
;
Crystal decay was monitored by repeating the initial 10 frames
at the end of the data collection and analyzing duplicate
reflections.
;

_diffrn_ambient_temperature       158(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'CCD area detector'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  8.192
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         0
_diffrn_reflns_number             8989
_diffrn_reflns_av_R_equivalents   0.0217
_diffrn_reflns_av_sigmaI/netI     0.0165
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.26
_diffrn_reflns_theta_max          26.34
_diffrn_measured_fraction_theta_max    0.976
_diffrn_reflns_theta_full              26.34
_diffrn_measured_fraction_theta_full   0.976
_reflns_number_total              2897
_reflns_number_gt                 2490
_reflns_threshold_expression      >2sigma(I)


_computing_data_collection        'Bruker SMART (Siemens, 1996)'
_computing_cell_refinement        'Bruker SMART (Siemens, 1996)'
_computing_data_reduction
;
Bruker SAINT (Siemens, 1996) & SADABS (Sheldrick, 1996)
;
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
ORTEP in WinGX (Farrugia, 1999)
;

_refine_special_details
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.0946P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2897
_refine_ls_number_parameters      239
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0449
_refine_ls_R_factor_gt            0.0392
_refine_ls_wR_factor_ref          0.1116
_refine_ls_wR_factor_gt           0.1079
_refine_ls_goodness_of_fit_ref    1.084
_refine_ls_restrained_S_all       1.084
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_diff_density_max    0.189
_refine_diff_density_min   -0.224
_refine_diff_density_rms    0.045

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25988(16) 0.57479(13) 1.54128(12) 0.0539(3) Uani 1 1 d . . .
H1 H 0.279(3) 0.570(2) 1.620(2) 0.065 Uiso 1 1 d . . .
O2 O 0.57027(16) 0.89004(12) 1.58879(13) 0.0512(3) Uani 1 1 d . . .
H2 H 0.616(3) 0.856(2) 1.521(2) 0.061 Uiso 1 1 d . . .
O3 O 0.32766(13) 0.56722(10) 0.80035(10) 0.0387(3) Uani 1 1 d . A .
O13 O 0.27749(13) 0.31197(10) 0.64991(10) 0.0354(2) Uani 1 1 d . A .
N1 N 0.22183(14) 0.67494(12) 1.30292(11) 0.0298(3) Uani 1 1 d . A .
N2 N 0.23771(15) 0.17622(12) 0.65622(12) 0.0330(3) Uani 1 1 d . A .
C3 C 0.2172(2) 0.77492(17) 1.45556(15) 0.0372(3) Uani 1 1 d . . .
H3A H 0.100(2) 0.7365(19) 1.4515(18) 0.045 Uiso 1 1 d . . .
H3B H 0.228(2) 0.8799(19) 1.4726(18) 0.045 Uiso 1 1 d . . .
C4 C 0.15598(17) 0.52143(14) 1.23113(14) 0.0304(3) Uani 1 1 d . . .
H4 H 0.1012 0.4803 1.2768 0.037 Uiso 1 1 calc R A .
C5 C 0.16706(17) 0.42517(13) 1.09448(13) 0.0280(3) Uani 1 1 d . A .
H5 H 0.1216 0.3183 1.0475 0.034 Uiso 1 1 calc R . .
C6 C 0.24560(15) 0.48273(13) 1.02186(13) 0.0242(3) Uani 1 1 d . . .
C7 C 0.30747(16) 0.64389(14) 1.09864(14) 0.0291(3) Uani 1 1 d . A .
H7 H 0.3577 0.6889 1.0537 0.035 Uiso 1 1 calc R . .
C8 C 0.29576(17) 0.73526(14) 1.23653(14) 0.0319(3) Uani 1 1 d . . .
H8 H 0.3401 0.8426 1.2866 0.038 Uiso 1 1 calc R A .
C11 C 0.25792(16) 0.38612(13) 0.87753(13) 0.0253(3) Uani 1 1 d . A .
C12 C 0.22556(16) 0.22344(13) 0.78921(13) 0.0261(3) Uani 1 1 d . . .
C14 C 0.29285(17) 0.43917(14) 0.78490(13) 0.0292(3) Uani 1 1 d . . .
C15 C 0.18952(16) 0.10395(13) 0.82632(13) 0.0267(3) Uani 1 1 d . A .
C16 C 0.30317(17) 0.11584(14) 0.95826(14) 0.0309(3) Uani 1 1 d . . .
H16 H 0.4008 0.2034 1.0282 0.037 Uiso 1 1 calc R A .
C17 C 0.27265(19) -0.00122(16) 0.98656(16) 0.0363(3) Uani 1 1 d . A .
H17 H 0.3489 0.0074 1.0764 0.044 Uiso 1 1 calc R . .
C18 C 0.13085(19) -0.13065(15) 0.88351(17) 0.0389(3) Uani 1 1 d . . .
H18 H 0.1117 -0.2106 0.9027 0.047 Uiso 1 1 calc R A .
C19 C 0.01746(19) -0.14314(15) 0.75284(16) 0.0388(3) Uani 1 1 d . A .
H19 H -0.0793 -0.2314 0.6829 0.047 Uiso 1 1 calc R . .
C20 C 0.04576(17) -0.02582(14) 0.72421(14) 0.0321(3) Uani 1 1 d . . .
H20 H -0.0327 -0.0341 0.6353 0.039 Uiso 1 1 calc R A .
C1A C 0.4297(4) 0.6598(3) 1.5660(3) 0.0383(9) Uani 0.535(5) 1 d P A 1
H1AA H 0.4701 0.6028 1.4808 0.046 Uiso 0.535(5) 1 calc PR A 1
H1AB H 0.5227 0.6801 1.6600 0.046 Uiso 0.535(5) 1 calc PR A 1
C2A C 0.3980(4) 0.8077(4) 1.5784(3) 0.0331(8) Uani 0.535(5) 1 d P A 1
H2A H 0.3840 0.8695 1.6777 0.040 Uiso 0.535(5) 1 calc PR A 1
C1B C 0.5179(4) 0.7448(3) 1.5785(3) 0.0317(9) Uani 0.465(5) 1 d P A 2
H1BA H 0.5972 0.7447 1.6669 0.038 Uiso 0.465(5) 1 calc PR A 2
H1BB H 0.5232 0.6589 1.4856 0.038 Uiso 0.465(5) 1 calc PR A 2
C2B C 0.3257(4) 0.7339(4) 1.5751(3) 0.0279(9) Uani 0.465(5) 1 d P A 2
H2B H 0.3269 0.8095 1.6771 0.034 Uiso 0.465(5) 1 calc PR A 2

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 0.0680(8) 0.0534(7) 0.0354(6) 0.0254(5) 0.0146(5) -0.0093(6)
O2 0.0614(7) 0.0346(6) 0.0446(6) 0.0095(5) 0.0266(5) -0.0038(5)
O3 0.0523(6) 0.0323(5) 0.0340(5) 0.0204(4) 0.0150(4) 0.0044(4)
O13 0.0466(5) 0.0336(5) 0.0266(5) 0.0150(4) 0.0163(4) 0.0064(4)
N1 0.0320(5) 0.0270(5) 0.0243(5) 0.0082(4) 0.0104(4) 0.0107(4)
N2 0.0406(6) 0.0281(6) 0.0286(6) 0.0128(5) 0.0147(5) 0.0060(5)
C3 0.0405(8) 0.0361(7) 0.0263(6) 0.0077(6) 0.0136(6) 0.0180(6)
C4 0.0350(7) 0.0293(6) 0.0285(6) 0.0145(5) 0.0143(5) 0.0093(5)
C5 0.0320(6) 0.0225(6) 0.0269(6) 0.0105(5) 0.0116(5) 0.0058(5)
C6 0.0216(5) 0.0240(6) 0.0245(6) 0.0114(5) 0.0066(4) 0.0061(4)
C7 0.0295(6) 0.0259(6) 0.0311(6) 0.0144(5) 0.0110(5) 0.0062(5)
C8 0.0316(6) 0.0230(6) 0.0322(7) 0.0093(5) 0.0091(5) 0.0061(5)
C11 0.0252(6) 0.0252(6) 0.0250(6) 0.0130(5) 0.0091(5) 0.0050(5)
C12 0.0251(6) 0.0262(6) 0.0236(6) 0.0108(5) 0.0085(5) 0.0056(5)
C14 0.0305(6) 0.0297(6) 0.0247(6) 0.0129(5) 0.0093(5) 0.0053(5)
C15 0.0305(6) 0.0214(6) 0.0278(6) 0.0098(5) 0.0150(5) 0.0084(5)
C16 0.0312(6) 0.0266(6) 0.0307(6) 0.0125(5) 0.0106(5) 0.0052(5)
C17 0.0384(7) 0.0377(7) 0.0390(7) 0.0237(6) 0.0144(6) 0.0124(6)
C18 0.0431(8) 0.0320(7) 0.0516(8) 0.0255(6) 0.0235(7) 0.0105(6)
C19 0.0372(7) 0.0269(7) 0.0440(8) 0.0139(6) 0.0136(6) 0.0008(5)
C20 0.0326(7) 0.0276(6) 0.0301(6) 0.0115(5) 0.0103(5) 0.0054(5)
C1A 0.0451(17) 0.0425(18) 0.0316(13) 0.0209(12) 0.0158(12) 0.0147(15)
C2A 0.0372(15) 0.0322(16) 0.0247(12) 0.0096(10) 0.0140(10) 0.0077(13)
C1B 0.0347(17) 0.0295(17) 0.0293(14) 0.0133(12) 0.0125(12) 0.0095(14)
C2B 0.0344(17) 0.0245(16) 0.0231(13) 0.0101(11) 0.0132(11) 0.0045(13)

_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1A 1.435(3) . ?
O1 C2B 1.510(4) . ?
O1 H1 0.85(2) . ?
O2 C1B 1.462(3) . ?
O2 C2A 1.502(4) . ?
O2 H2 0.85(2) . ?
O3 C14 1.2447(16) . ?
O13 C14 1.3859(15) . ?
O13 N2 1.4454(14) . ?
N1 C8 1.3589(17) . ?
N1 C4 1.3605(17) . ?
N1 C3 1.4872(16) . ?
N2 C12 1.3167(16) . ?
C3 C2A 1.546(3) . ?
C3 C2B 1.598(3) . ?
C3 H3A 0.965(18) . ?
C3 H3B 0.999(17) . ?
C4 C5 1.3674(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4191(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4207(17) . ?
C6 C11 1.4359(17) . ?
C7 C8 1.3698(18) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C11 C14 1.4237(17) . ?
C11 C12 1.4352(17) . ?
C12 C15 1.4940(17) . ?
C15 C20 1.4021(18) . ?
C15 C16 1.4032(18) . ?
C16 C17 1.3962(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3983(19) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C1A C2A 1.514(5) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C2A H2A 1.0000 . ?
C1B C2B 1.519(5) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B H2B 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1 C2B 46.62(16) . . ?
C1A O1 H1 103.8(14) . . ?
C2B O1 H1 112.8(14) . . ?
C1B O2 C2A 47.72(15) . . ?
C1B O2 H2 96.0(13) . . ?
C2A O2 H2 124.5(13) . . ?
C14 O13 N2 109.59(9) . . ?
C8 N1 C4 119.81(11) . . ?
C8 N1 C3 120.55(11) . . ?
C4 N1 C3 119.61(11) . . ?
C12 N2 O13 105.73(10) . . ?
N1 C3 C2A 110.37(13) . . ?
N1 C3 C2B 112.36(13) . . ?
C2A C3 C2B 33.06(13) . . ?
N1 C3 H3A 105.8(10) . . ?
C2A C3 H3A 124.7(10) . . ?
C2B C3 H3A 94.6(10) . . ?
N1 C3 H3B 107.1(9) . . ?
C2A C3 H3B 97.9(10) . . ?
C2B C3 H3B 125.1(10) . . ?
H3A C3 H3B 109.8(14) . . ?
N1 C4 C5 121.30(11) . . ?
N1 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 120.89(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 115.89(11) . . ?
C5 C6 C11 122.80(11) . . ?
C7 C6 C11 121.29(11) . . ?
C8 C7 C6 120.94(12) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
N1 C8 C7 121.13(11) . . ?
N1 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C14 C11 C6 124.01(11) . . ?
C14 C11 C12 104.97(10) . . ?
C6 C11 C12 130.82(11) . . ?
N2 C12 C11 112.56(11) . . ?
N2 C12 C15 116.55(10) . . ?
C11 C12 C15 130.83(11) . . ?
O3 C14 O13 118.68(11) . . ?
O3 C14 C11 134.19(11) . . ?
O13 C14 C11 107.11(11) . . ?
C20 C15 C16 119.43(11) . . ?
C20 C15 C12 119.58(11) . . ?
C16 C15 C12 120.91(11) . . ?
C17 C16 C15 119.92(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.26(13) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.18(13) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.99(12) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.22(12) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
O1 C1A C2A 105.9(2) . . ?
O1 C1A H1AA 110.6 . . ?
C2A C1A H1AA 110.6 . . ?
O1 C1A H1AB 110.6 . . ?
C2A C1A H1AB 110.6 . . ?
H1AA C1A H1AB 108.7 . . ?
O2 C2A C1A 106.0(2) . . ?
O2 C2A C3 120.5(2) . . ?
C1A C2A C3 109.7(2) . . ?
O2 C2A H2A 106.6 . . ?
C1A C2A H2A 106.6 . . ?
C3 C2A H2A 106.6 . . ?
O2 C1B C2B 104.0(2) . . ?
O2 C1B H1BA 111.0 . . ?
C2B C1B H1BA 111.0 . . ?
O2 C1B H1BB 111.0 . . ?
C2B C1B H1BB 111.0 . . ?
H1BA C1B H1BB 109.0 . . ?
O1 C2B C1B 104.7(2) . . ?
O1 C2B C3 116.4(2) . . ?
C1B C2B C3 108.1(2) . . ?
O1 C2B H2B 109.1 . . ?
C1B C2B H2B 109.1 . . ?
C3 C2B H2B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O13 N2 C12 1.65(13) . . . . ?
C8 N1 C3 C2A -83.7(2) . . . . ?
C4 N1 C3 C2A 94.45(19) . . . . ?
C8 N1 C3 C2B -119.23(19) . . . . ?
C4 N1 C3 C2B 58.9(2) . . . . ?
C8 N1 C4 C5 1.88(18) . . . . ?
C3 N1 C4 C5 -176.30(11) . . . . ?
N1 C4 C5 C6 -0.92(19) . . . . ?
C4 C5 C6 C7 -1.01(18) . . . . ?
C4 C5 C6 C11 -179.15(11) . . . . ?
C5 C6 C7 C8 2.04(17) . . . . ?
C11 C6 C7 C8 -179.79(11) . . . . ?
C4 N1 C8 C7 -0.82(18) . . . . ?
C3 N1 C8 C7 177.34(11) . . . . ?
C6 C7 C8 N1 -1.18(19) . . . . ?
C5 C6 C11 C14 163.55(12) . . . . ?
C7 C6 C11 C14 -14.49(18) . . . . ?
C5 C6 C11 C12 -10.6(2) . . . . ?
C7 C6 C11 C12 171.37(12) . . . . ?
O13 N2 C12 C11 -0.98(13) . . . . ?
O13 N2 C12 C15 -178.42(10) . . . . ?
C14 C11 C12 N2 0.00(14) . . . . ?
C6 C11 C12 N2 174.97(12) . . . . ?
C14 C11 C12 C15 176.97(12) . . . . ?
C6 C11 C12 C15 -8.1(2) . . . . ?
N2 O13 C14 O3 179.76(11) . . . . ?
N2 O13 C14 C11 -1.66(13) . . . . ?
C6 C11 C14 O3 3.9(2) . . . . ?
C12 C11 C14 O3 179.30(14) . . . . ?
C6 C11 C14 O13 -174.37(10) . . . . ?
C12 C11 C14 O13 1.04(13) . . . . ?
N2 C12 C15 C20 -51.08(16) . . . . ?
C11 C12 C15 C20 132.05(13) . . . . ?
N2 C12 C15 C16 125.55(13) . . . . ?
C11 C12 C15 C16 -51.33(18) . . . . ?
C20 C15 C16 C17 0.14(18) . . . . ?
C12 C15 C16 C17 -176.49(11) . . . . ?
C15 C16 C17 C18 0.68(19) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C16 C15 C20 C19 -0.81(18) . . . . ?
C12 C15 C20 C19 175.87(11) . . . . ?
C2B O1 C1A C2A -5.64(17) . . . . ?
C1B O2 C2A C1A -1.66(18) . . . . ?
C1B O2 C2A C3 -126.8(3) . . . . ?
O1 C1A C2A O2 -174.50(15) . . . . ?
O1 C1A C2A C3 -42.9(3) . . . . ?
N1 C3 C2A O2 61.9(2) . . . . ?
C2B C3 C2A O2 161.9(4) . . . . ?
N1 C3 C2A C1A -61.5(3) . . . . ?
C2B C3 C2A C1A 38.5(3) . . . . ?
C2A O2 C1B C2B -1.23(17) . . . . ?
C1A O1 C2B C1B 3.19(18) . . . . ?
C1A O1 C2B C3 122.5(3) . . . . ?
O2 C1B C2B O1 171.88(16) . . . . ?
O2 C1B C2B C3 47.2(2) . . . . ?
N1 C3 C2B O1 -60.6(2) . . . . ?
C2A C3 C2B O1 -153.9(4) . . . . ?
N1 C3 C2B C1B 56.8(3) . . . . ?
C2A C3 C2B C1B -36.5(2) . . . . ?