# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
H.Koshima
K.Takechi
H.Uchimoto
M.Shiro
D.Hashimoto
_publ_contact_author_name        'Hideko Koshima'
_publ_contact_author_email       koshima.hideko.mk@ehime-u.ac.jp

data_irradiation-3600sec
_database_code_depnum_ccdc_archive 'CCDC 833512'
#TrackingRef 'CCDC833512_revised.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.1172(4)
_cell_length_b                   10.3417(7)
_cell_length_c                   16.2127(10)
_cell_angle_alpha                102.017(4)
_cell_angle_beta                 92.797(3)
_cell_angle_gamma                103.296(4)
_cell_volume                     971.23(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    123
_cell_measurement_reflns_used    4042
_cell_measurement_theta_min      4.51
_cell_measurement_theta_max      68.16

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_process_details   PROCESS-AUTO

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w-scan
_diffrn_detector_area_resol_mean 10
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6667
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_sigmaI/netI    0.1477
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.51
_diffrn_reflns_theta_max         68.25
_reflns_number_total             3313
_reflns_number_gt                1269
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    SIR-2004
_computing_structure_refinement  SHELXL-97
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  SHELXL-97

_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.

The shape of the specimen was very thin plate, almost needle,
in order to acheve high conversion of photoisomerization.
In addition, the crystallinity of the specimen was
lowered after the isomerization.
These made Bragg spots weak and diffuse
to lower statics of intensities,
the R factor of the analysis became high accordingly.

All bond distances corresponding the photoisomerization were
restrained with the reported distances
(J. Harada, et al., JACS, 1999, 121, 5809)
with the error of 0.002 \%A on the first stage of the refinements.
After converged the parameters, the bond restraints were relaxed,
and finally we imposed the bond restraints with the error of 0.01 \%A.
On the final refinements, the bond distances of the product was converged
within the error on the restraints.
;

_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^)+(0.1806P)^2^] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3313
_refine_ls_number_parameters     306
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.1951
_refine_ls_R_factor_gt           0.1245
_refine_ls_wR_factor_ref         0.3644
_refine_ls_wR_factor_gt          0.2950
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

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
O1A O 0.3320(5) 0.3808(2) 0.31118(16) 0.0693(9) Uani 0.9053(17) 1 d PD A 1
H1A H 0.3010 0.4321 0.3540 0.104 Uiso 0.9053(17) 1 calc PR A 1
O2A O 0.3619(5) 1.0328(3) 0.5995(2) 0.0877(11) Uani 0.9053(17) 1 d PD A 1
O3A O 0.0420(5) 1.0496(3) 0.64967(19) 0.0874(11) Uani 0.9053(17) 1 d PD A 1
N1A N 0.1849(5) 0.5936(3) 0.37868(18) 0.0664(11) Uani 0.9053(17) 1 d PD A 1
N2A N 0.1588(6) 0.9916(3) 0.6023(2) 0.0711(12) Uani 0.9053(17) 1 d PD A 1
C1A C 0.4412(6) 0.5955(3) 0.2716(2) 0.0586(12) Uani 0.9053(17) 1 d PD A 1
C2A C 0.4488(6) 0.4576(3) 0.2620(2) 0.0636(12) Uani 0.9053(17) 1 d PD A 1
C3A C 0.5899(6) 0.4027(3) 0.2047(2) 0.0555(11) Uani 0.9053(17) 1 d PD A 1
C4A C 0.7086(7) 0.4876(3) 0.1571(2) 0.0581(11) Uani 0.9053(17) 1 d PD A 1
H4A H 0.8010 0.4515 0.1175 0.070 Uiso 0.9053(17) 1 calc PR A 1
C5A C 0.6986(6) 0.6258(3) 0.1647(2) 0.0567(11) Uani 0.9053(17) 1 d PD A 1
C6A C 0.5654(6) 0.6755(4) 0.2223(2) 0.0609(12) Uani 0.9053(17) 1 d PD A 1
H6A H 0.5573 0.7677 0.2291 0.073 Uiso 0.9053(17) 1 calc PR A 1
C7A C 0.3057(6) 0.6568(4) 0.3308(2) 0.0681(13) Uani 0.9053(17) 1 d PD A 1
H7A H 0.3067 0.7498 0.3344 0.082 Uiso 0.9053(17) 1 calc PR A 1
C8A C 0.0644(3) 0.6664(2) 0.43819(12) 0.0661(13) Uani 0.9053(17) 1 d PGD A 1
C9A C 0.1679(4) 0.7937(2) 0.48921(14) 0.0682(13) Uani 0.9053(17) 1 d PG A 1
H9A H 0.3212 0.8350 0.4847 0.082 Uiso 0.9053(17) 1 calc PR A 1
C10A C 0.0473(5) 0.8607(2) 0.54690(15) 0.0705(13) Uani 0.9053(17) 1 d PGD A 1
C11A C -0.1770(5) 0.8003(3) 0.55357(17) 0.0655(13) Uani 0.9053(17) 1 d PG A 1
H11A H -0.2594 0.8461 0.5930 0.079 Uiso 0.9053(17) 1 calc PR A 1
C12A C -0.2806(4) 0.6729(3) 0.50255(18) 0.0669(13) Uani 0.9053(17) 1 d PG A 1
H12A H -0.4338 0.6316 0.5071 0.080 Uiso 0.9053(17) 1 calc PR A 1
C13A C -0.1599(4) 0.6060(2) 0.44486(15) 0.0660(13) Uani 0.9053(17) 1 d PG A 1
H13A H -0.2307 0.5189 0.4100 0.079 Uiso 0.9053(17) 1 calc PR A 1
C14A C 0.5996(6) 0.2524(3) 0.1929(2) 0.0627(12) Uani 0.9053(17) 1 d PD A 1
C15A C 0.3656(7) 0.1549(4) 0.1646(3) 0.0761(14) Uani 0.9053(17) 1 d PD A 1
H15A H 0.2669 0.1677 0.2099 0.114 Uiso 0.9053(17) 1 calc PR A 1
H15B H 0.3800 0.0605 0.1524 0.114 Uiso 0.9053(17) 1 calc PR A 1
H15C H 0.3005 0.1742 0.1134 0.114 Uiso 0.9053(17) 1 calc PR A 1
C16A C 0.7008(7) 0.2297(4) 0.2757(3) 0.0715(14) Uani 0.9053(17) 1 d PD A 1
H16A H 0.8403 0.3004 0.2967 0.107 Uiso 0.9053(17) 1 calc PR A 1
H16B H 0.7344 0.1398 0.2651 0.107 Uiso 0.9053(17) 1 calc PR A 1
H16C H 0.5925 0.2343 0.3181 0.107 Uiso 0.9053(17) 1 calc PR A 1
C17A C 0.7526(7) 0.2122(5) 0.1245(3) 0.0789(14) Uani 0.9053(17) 1 d PD A 1
H17A H 0.6883 0.2185 0.0693 0.118 Uiso 0.9053(17) 1 calc PR A 1
H17B H 0.7634 0.1184 0.1220 0.118 Uiso 0.9053(17) 1 calc PR A 1
H17C H 0.9035 0.2741 0.1385 0.118 Uiso 0.9053(17) 1 calc PR A 1
C18A C 0.8374(6) 0.7083(3) 0.1080(2) 0.0596(12) Uani 0.9053(17) 1 d PD A 1
C19A C 0.7738(9) 0.6340(5) 0.0148(2) 0.0720(13) Uani 0.9053(17) 1 d PD A 1
H19A H 0.7967 0.5416 0.0069 0.108 Uiso 0.9053(17) 1 calc PR A 1
H19B H 0.8692 0.6840 -0.0209 0.108 Uiso 0.9053(17) 1 calc PR A 1
H19C H 0.6150 0.6287 -0.0012 0.108 Uiso 0.9053(17) 1 calc PR A 1
C20A C 1.0902(6) 0.7261(4) 0.1324(3) 0.0679(14) Uani 0.9053(17) 1 d PD A 1
H20A H 1.1320 0.7807 0.1905 0.102 Uiso 0.9053(17) 1 calc PR A 1
H20B H 1.1785 0.7725 0.0935 0.102 Uiso 0.9053(17) 1 calc PR A 1
H20C H 1.1213 0.6363 0.1287 0.102 Uiso 0.9053(17) 1 calc PR A 1
C21A C 0.7922(8) 0.8519(3) 0.1203(3) 0.0764(14) Uani 0.9053(17) 1 d PD A 1
H21A H 0.6299 0.8433 0.1096 0.115 Uiso 0.9053(17) 1 calc PR A 1
H21B H 0.8730 0.9002 0.0806 0.115 Uiso 0.9053(17) 1 calc PR A 1
H21C H 0.8452 0.9032 0.1785 0.115 Uiso 0.9053(17) 1 calc PR A 1
O1B O 0.308(3) 0.3054(13) 0.2782(13) 0.0693(9) Uani 0.0947(17) 1 d PD A 2
O2B O 0.2411(18) 1.068(2) 0.6097(18) 0.0877(11) Uani 0.0947(17) 1 d PD A 2
O3B O -0.079(2) 1.028(3) 0.6710(10) 0.0874(11) Uani 0.0947(17) 1 d PD A 2
N1B N 0.2770(19) 0.6963(10) 0.3698(10) 0.0664(11) Uani 0.0947(17) 1 d PD A 2
H1B H 0.3907 0.7602 0.3614 0.080 Uiso 0.0947(17) 1 calc PR A 2
N2B N 0.055(2) 0.9993(11) 0.6207(11) 0.0711(12) Uani 0.0947(17) 1 d PD A 2
C1B C 0.4650(14) 0.5508(10) 0.2833(7) 0.0586(12) Uani 0.0947(17) 1 d PGD A 2
C2B C 0.444(2) 0.4110(9) 0.2605(8) 0.0636(12) Uani 0.0947(17) 1 d PGD A 2
C3B C 0.556(4) 0.3571(11) 0.1941(10) 0.0555(11) Uani 0.0947(17) 1 d PGD A 2
C4B C 0.688(4) 0.4430(17) 0.1504(11) 0.0581(11) Uani 0.0947(17) 1 d PGD A 2
H4B H 0.7641 0.4061 0.1050 0.070 Uiso 0.0947(17) 1 calc PR A 2
C5B C 0.709(3) 0.5828(16) 0.1732(11) 0.0567(11) Uani 0.0947(17) 1 d PGD A 2
C6B C 0.597(2) 0.6367(9) 0.2396(9) 0.0609(12) Uani 0.0947(17) 1 d PG A 2
H6B H 0.6115 0.7323 0.2552 0.073 Uiso 0.0947(17) 1 calc PR A 2
C7B C 0.276(2) 0.5694(12) 0.3270(13) 0.0681(13) Uani 0.0947(17) 1 d PD A 2
H7B H 0.1516 0.4946 0.3261 0.082 Uiso 0.0947(17) 1 calc PR A 2
C8B C 0.129(2) 0.7455(16) 0.4259(10) 0.0661(13) Uani 0.0947(17) 1 d PGD A 2
C9B C 0.183(4) 0.8573(16) 0.4943(11) 0.0682(13) Uani 0.0947(17) 1 d PG A 2
H9B H 0.3178 0.9264 0.4977 0.082 Uiso 0.0947(17) 1 calc PR A 2
C10B C 0.039(5) 0.8680(19) 0.5579(12) 0.0705(13) Uani 0.0947(17) 1 d PGD A 2
C11B C -0.158(5) 0.767(3) 0.5530(16) 0.0655(13) Uani 0.0947(17) 1 d PG A 2
H11B H -0.2563 0.7742 0.5964 0.079 Uiso 0.0947(17) 1 calc PR A 2
C12B C -0.212(4) 0.655(3) 0.4845(17) 0.0669(13) Uani 0.0947(17) 1 d PG A 2
H12B H -0.3467 0.5860 0.4811 0.080 Uiso 0.0947(17) 1 calc PR A 2
C13B C -0.068(3) 0.6444(17) 0.4209(12) 0.0660(13) Uani 0.0947(17) 1 d PG A 2
H13B H -0.1049 0.5680 0.3741 0.079 Uiso 0.0947(17) 1 calc PR A 2
C14B C 0.6054(13) 0.2153(8) 0.1803(6) 0.0627(12) Uani 0.0947(17) 1 d PD A 2
C15B C 0.381(2) 0.106(2) 0.167(3) 0.0761(14) Uani 0.0947(17) 1 d PD A 2
H15D H 0.2559 0.1470 0.1561 0.114 Uiso 0.0947(17) 1 calc PR A 2
H15E H 0.3599 0.0697 0.2181 0.114 Uiso 0.0947(17) 1 calc PR A 2
H15F H 0.3833 0.0320 0.1186 0.114 Uiso 0.0947(17) 1 calc PR A 2
C16B C 0.673(5) 0.163(2) 0.2574(11) 0.0715(14) Uani 0.0947(17) 1 d PD A 2
H16D H 0.6477 0.0637 0.2417 0.107 Uiso 0.0947(17) 1 calc PR A 2
H16E H 0.5822 0.1883 0.3034 0.107 Uiso 0.0947(17) 1 calc PR A 2
H16F H 0.8336 0.2044 0.2765 0.107 Uiso 0.0947(17) 1 calc PR A 2
C17B C 0.803(2) 0.223(6) 0.1247(13) 0.0789(14) Uani 0.0947(17) 1 d PD A 2
H17D H 0.9234 0.3042 0.1498 0.118 Uiso 0.0947(17) 1 calc PR A 2
H17E H 0.7499 0.2278 0.0677 0.118 Uiso 0.0947(17) 1 calc PR A 2
H17F H 0.8608 0.1412 0.1212 0.118 Uiso 0.0947(17) 1 calc PR A 2
C18B C 0.8101(14) 0.6709(8) 0.1134(5) 0.0596(12) Uani 0.0947(17) 1 d PD A 2
C19B C 0.776(10) 0.626(5) 0.0163(6) 0.0720(13) Uani 0.0947(17) 1 d PD A 2
H19D H 0.8007 0.5346 -0.0015 0.108 Uiso 0.0947(17) 1 calc PR A 2
H19E H 0.8830 0.6903 -0.0080 0.108 Uiso 0.0947(17) 1 calc PR A 2
H19F H 0.6212 0.6249 -0.0037 0.108 Uiso 0.0947(17) 1 calc PR A 2
C20B C 1.0622(18) 0.675(4) 0.128(3) 0.0679(14) Uani 0.0947(17) 1 d PD A 2
H20D H 1.1507 0.7448 0.1016 0.102 Uiso 0.0947(17) 1 calc PR A 2
H20E H 1.0872 0.5859 0.1021 0.102 Uiso 0.0947(17) 1 calc PR A 2
H20F H 1.1093 0.6977 0.1887 0.102 Uiso 0.0947(17) 1 calc PR A 2
C21B C 0.802(6) 0.8211(12) 0.127(4) 0.0764(14) Uani 0.0947(17) 1 d PD A 2
H21D H 0.6581 0.8269 0.1007 0.115 Uiso 0.0947(17) 1 calc PR A 2
H21E H 0.9269 0.8711 0.1020 0.115 Uiso 0.0947(17) 1 calc PR A 2
H21F H 0.8146 0.8611 0.1883 0.115 Uiso 0.0947(17) 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
O1A 0.0809(19) 0.0656(16) 0.0632(16) 0.0352(13) 0.0193(14) 0.0008(14)
O2A 0.088(2) 0.0816(19) 0.085(2) 0.0298(15) 0.0241(18) -0.0101(17)
O3A 0.103(2) 0.083(2) 0.070(2) 0.0143(16) 0.0147(18) 0.0123(18)
N1A 0.075(2) 0.069(2) 0.0536(18) 0.0295(15) 0.0070(17) 0.0006(17)
N2A 0.077(3) 0.067(2) 0.067(2) 0.0353(16) 0.022(2) -0.0078(19)
C1A 0.055(2) 0.070(2) 0.058(2) 0.0405(18) 0.0057(19) 0.0081(19)
C2A 0.065(2) 0.071(2) 0.054(2) 0.0371(18) 0.0133(19) -0.008(2)
C3A 0.056(2) 0.057(2) 0.056(2) 0.0372(16) 0.0107(18) -0.0029(18)
C4A 0.061(2) 0.047(2) 0.061(2) 0.0241(17) 0.0083(19) -0.0095(18)
C5A 0.062(2) 0.0483(19) 0.065(2) 0.0363(17) 0.007(2) 0.0020(18)
C6A 0.064(3) 0.071(2) 0.056(2) 0.0408(18) 0.0107(19) 0.009(2)
C7A 0.067(3) 0.076(3) 0.061(2) 0.041(2) 0.008(2) -0.004(2)
C8A 0.085(3) 0.077(3) 0.043(2) 0.0298(19) 0.015(2) 0.014(2)
C9A 0.083(3) 0.067(2) 0.058(2) 0.0388(19) 0.012(2) 0.001(2)
C10A 0.086(3) 0.076(2) 0.055(2) 0.0378(18) 0.021(2) 0.007(2)
C11A 0.076(3) 0.067(2) 0.059(2) 0.0357(18) 0.022(2) 0.007(2)
C12A 0.069(3) 0.083(3) 0.052(2) 0.0294(19) 0.021(2) 0.010(2)
C13A 0.071(3) 0.075(3) 0.054(2) 0.0335(19) 0.017(2) 0.002(2)
C14A 0.078(3) 0.053(2) 0.061(2) 0.0361(17) 0.009(2) 0.0031(19)
C15A 0.078(3) 0.053(2) 0.096(3) 0.039(2) 0.001(3) -0.006(2)
C16A 0.075(3) 0.059(2) 0.081(3) 0.037(2) 0.002(2) -0.001(2)
C17A 0.091(3) 0.072(2) 0.084(3) 0.040(2) 0.029(2) 0.018(2)
C18A 0.061(2) 0.046(2) 0.068(2) 0.0264(18) 0.012(2) -0.0071(18)
C19A 0.082(3) 0.066(2) 0.066(2) 0.0336(18) 0.012(2) -0.004(2)
C20A 0.079(3) 0.055(2) 0.068(3) 0.029(2) 0.009(2) -0.002(2)
C21A 0.094(3) 0.049(2) 0.089(3) 0.041(2) 0.013(3) -0.001(2)
O1B 0.0809(19) 0.0656(16) 0.0632(16) 0.0352(13) 0.0193(14) 0.0008(14)
O2B 0.088(2) 0.0816(19) 0.085(2) 0.0298(15) 0.0241(18) -0.0101(17)
O3B 0.103(2) 0.083(2) 0.070(2) 0.0143(16) 0.0147(18) 0.0123(18)
N1B 0.075(2) 0.069(2) 0.0536(18) 0.0295(15) 0.0070(17) 0.0006(17)
N2B 0.077(3) 0.067(2) 0.067(2) 0.0353(16) 0.022(2) -0.0078(19)
C1B 0.055(2) 0.070(2) 0.058(2) 0.0405(18) 0.0057(19) 0.0081(19)
C2B 0.065(2) 0.071(2) 0.054(2) 0.0371(18) 0.0133(19) -0.008(2)
C3B 0.056(2) 0.057(2) 0.056(2) 0.0372(16) 0.0107(18) -0.0029(18)
C4B 0.061(2) 0.047(2) 0.061(2) 0.0241(17) 0.0083(19) -0.0095(18)
C5B 0.062(2) 0.0483(19) 0.065(2) 0.0363(17) 0.007(2) 0.0020(18)
C6B 0.064(3) 0.071(2) 0.056(2) 0.0408(18) 0.0107(19) 0.009(2)
C7B 0.067(3) 0.076(3) 0.061(2) 0.041(2) 0.008(2) -0.004(2)
C8B 0.085(3) 0.077(3) 0.043(2) 0.0298(19) 0.015(2) 0.014(2)
C9B 0.083(3) 0.067(2) 0.058(2) 0.0388(19) 0.012(2) 0.001(2)
C10B 0.086(3) 0.076(2) 0.055(2) 0.0378(18) 0.021(2) 0.007(2)
C11B 0.076(3) 0.067(2) 0.059(2) 0.0357(18) 0.022(2) 0.007(2)
C12B 0.069(3) 0.083(3) 0.052(2) 0.0294(19) 0.021(2) 0.010(2)
C13B 0.071(3) 0.075(3) 0.054(2) 0.0335(19) 0.017(2) 0.002(2)
C14B 0.078(3) 0.053(2) 0.061(2) 0.0361(17) 0.009(2) 0.0031(19)
C15B 0.078(3) 0.053(2) 0.096(3) 0.039(2) 0.001(3) -0.006(2)
C16B 0.075(3) 0.059(2) 0.081(3) 0.037(2) 0.002(2) -0.001(2)
C17B 0.091(3) 0.072(2) 0.084(3) 0.040(2) 0.029(2) 0.018(2)
C18B 0.061(2) 0.046(2) 0.068(2) 0.0264(18) 0.012(2) -0.0071(18)
C19B 0.082(3) 0.066(2) 0.066(2) 0.0336(18) 0.012(2) -0.004(2)
C20B 0.079(3) 0.055(2) 0.068(3) 0.029(2) 0.009(2) -0.002(2)
C21B 0.094(3) 0.049(2) 0.089(3) 0.041(2) 0.013(3) -0.001(2)

_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
O1A C2A 1.355(4) . ?
O1A H1A 0.8400 . ?
O2A N2A 1.224(4) . ?
O3A N2A 1.233(4) . ?
N1A C7A 1.273(4) . ?
N1A C8A 1.436(3) . ?
N2A C10A 1.454(3) . ?
C1A C6A 1.395(4) . ?
C1A C2A 1.414(5) . ?
C1A C7A 1.441(5) . ?
C2A C3A 1.419(5) . ?
C3A C4A 1.392(4) . ?
C3A C14A 1.542(4) . ?
C4A C5A 1.425(4) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.366(5) . ?
C5A C18A 1.537(4) . ?
C6A H6A 0.9500 . ?
C7A H7A 0.9500 . ?
C8A C9A 1.3900 . ?
C8A C13A 1.3900 . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.3900 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A C15A 1.535(5) . ?
C14A C16A 1.535(5) . ?
C14A C17A 1.539(5) . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A C19A 1.532(4) . ?
C18A C20A 1.537(5) . ?
C18A C21A 1.546(5) . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
O1B C2B 1.305(9) . ?
O2B N2B 1.239(9) . ?
O3B N2B 1.224(10) . ?
N1B C7B 1.349(9) . ?
N1B C8B 1.415(9) . ?
N1B H1B 0.8800 . ?
N2B C10B 1.498(9) . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C1B C7B 1.415(9) . ?
C2B C3B 1.3900 . ?
C3B C4B 1.3900 . ?
C3B C14B 1.539(9) . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3900 . ?
C5B C18B 1.524(9) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
C8B C9B 1.3900 . ?
C8B C13B 1.3900 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3900 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B C16B 1.536(10) . ?
C14B C15B 1.538(9) . ?
C14B C17B 1.538(10) . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B C19B 1.535(9) . ?
C18B C21B 1.536(9) . ?
C18B C20B 1.537(9) . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?

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
C7A N1A C8A 119.2(3) . . ?
O2A N2A O3A 125.6(3) . . ?
O2A N2A C10A 117.1(3) . . ?
O3A N2A C10A 117.2(3) . . ?
C6A C1A C2A 119.9(3) . . ?
C6A C1A C7A 118.3(3) . . ?
C2A C1A C7A 121.8(3) . . ?
O1A C2A C1A 119.9(3) . . ?
O1A C2A C3A 120.2(3) . . ?
C1A C2A C3A 119.8(3) . . ?
C4A C3A C2A 117.4(3) . . ?
C4A C3A C14A 121.9(3) . . ?
C2A C3A C14A 120.6(3) . . ?
C3A C4A C5A 123.3(3) . . ?
C6A C5A C4A 117.2(3) . . ?
C6A C5A C18A 124.7(3) . . ?
C4A C5A C18A 118.1(3) . . ?
C5A C6A C1A 122.3(4) . . ?
N1A C7A C1A 123.8(4) . . ?
C9A C8A C13A 120.0 . . ?
C9A C8A N1A 121.43(17) . . ?
C13A C8A N1A 118.56(17) . . ?
C10A C9A C8A 120.0 . . ?
C11A C10A C9A 120.0 . . ?
C11A C10A N2A 120.2(2) . . ?
C9A C10A N2A 119.8(2) . . ?
C10A C11A C12A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C12A C13A C8A 120.0 . . ?
C15A C14A C16A 110.7(3) . . ?
C15A C14A C17A 106.2(3) . . ?
C16A C14A C17A 106.4(3) . . ?
C15A C14A C3A 111.6(3) . . ?
C16A C14A C3A 109.7(3) . . ?
C17A C14A C3A 112.0(3) . . ?
C19A C18A C20A 110.1(3) . . ?
C19A C18A C5A 109.7(3) . . ?
C20A C18A C5A 109.4(3) . . ?
C19A C18A C21A 109.0(3) . . ?
C20A C18A C21A 107.9(3) . . ?
C5A C18A C21A 110.7(3) . . ?
C7B N1B C8B 131.9(12) . . ?
C7B N1B H1B 114.1 . . ?
C8B N1B H1B 114.1 . . ?
O3B N2B O2B 130.0(18) . . ?
O3B N2B C10B 128.6(17) . . ?
O2B N2B C10B 101.4(18) . . ?
C2B C1B C6B 120.0 . . ?
C2B C1B C7B 106.5(9) . . ?
C6B C1B C7B 129.0(10) . . ?
O1B C2B C3B 105.0(11) . . ?
O1B C2B C1B 134.0(12) . . ?
C3B C2B C1B 120.0 . . ?
C2B C3B C4B 120.0 . . ?
C2B C3B C14B 124.2(9) . . ?
C4B C3B C14B 113.2(10) . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C4B C5B C18B 118.8(10) . . ?
C6B C5B C18B 119.8(10) . . ?
C5B C6B C1B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
N1B C7B C1B 118.3(11) . . ?
N1B C7B H7B 120.9 . . ?
C1B C7B H7B 120.9 . . ?
C9B C8B C13B 120.0 . . ?
C9B C8B N1B 127.6(12) . . ?
C13B C8B N1B 109.8(12) . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C9B C10B C11B 120.0 . . ?
C9B C10B N2B 122.3(16) . . ?
C11B C10B N2B 116.0(17) . . ?
C10B C11B C12B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C13B C12B C11B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C12B C13B C8B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C8B C13B H13B 120.0 . . ?
C16B C14B C15B 88(2) . . ?
C16B C14B C17B 107(2) . . ?
C15B C14B C17B 128(2) . . ?
C16B C14B C3B 119.3(13) . . ?
C15B C14B C3B 109.0(13) . . ?
C17B C14B C3B 105(2) . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C14B C16B H16D 109.5 . . ?
C14B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C14B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C14B C17B H17D 109.5 . . ?
C14B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C14B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C5B C18B C19B 125(2) . . ?
C5B C18B C21B 121(2) . . ?
C19B C18B C21B 101(3) . . ?
C5B C18B C20B 101.6(18) . . ?
C19B C18B C20B 100(3) . . ?
C21B C18B C20B 104.8(19) . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C18B C20B H20D 109.5 . . ?
C18B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C18B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C18B C21B H21D 109.5 . . ?
C18B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C18B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?

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
C6A C1A C2A O1A 178.5(3) . . . . ?
C7A C1A C2A O1A -2.0(5) . . . . ?
C6A C1A C2A C3A 2.5(5) . . . . ?
C7A C1A C2A C3A -178.1(3) . . . . ?
O1A C2A C3A C4A -178.8(3) . . . . ?
C1A C2A C3A C4A -2.8(5) . . . . ?
O1A C2A C3A C14A 4.3(5) . . . . ?
C1A C2A C3A C14A -179.6(3) . . . . ?
C2A C3A C4A C5A 1.4(5) . . . . ?
C14A C3A C4A C5A 178.2(3) . . . . ?
C3A C4A C5A C6A 0.3(5) . . . . ?
C3A C4A C5A C18A -179.7(3) . . . . ?
C4A C5A C6A C1A -0.7(5) . . . . ?
C18A C5A C6A C1A 179.3(3) . . . . ?
C2A C1A C6A C5A -0.7(5) . . . . ?
C7A C1A C6A C5A 179.9(3) . . . . ?
C8A N1A C7A C1A 177.2(3) . . . . ?
C6A C1A C7A N1A 179.7(4) . . . . ?
C2A C1A C7A N1A 0.2(6) . . . . ?
C7A N1A C8A C9A -46.2(4) . . . . ?
C7A N1A C8A C13A 134.6(3) . . . . ?
C13A C8A C9A C10A 0.0 . . . . ?
N1A C8A C9A C10A -179.2(2) . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
C8A C9A C10A N2A 177.7(3) . . . . ?
O2A N2A C10A C11A 172.6(3) . . . . ?
O3A N2A C10A C11A -5.4(4) . . . . ?
O2A N2A C10A C9A -5.1(4) . . . . ?
O3A N2A C10A C9A 176.9(3) . . . . ?
C9A C10A C11A C12A 0.0 . . . . ?
N2A C10A C11A C12A -177.7(3) . . . . ?
C10A C11A C12A C13A 0.0 . . . . ?
C11A C12A C13A C8A 0.0 . . . . ?
C9A C8A C13A C12A 0.0 . . . . ?
N1A C8A C13A C12A 179.2(2) . . . . ?
C4A C3A C14A C15A -118.8(4) . . . . ?
C2A C3A C14A C15A 57.9(5) . . . . ?
C4A C3A C14A C16A 118.1(4) . . . . ?
C2A C3A C14A C16A -65.2(4) . . . . ?
C4A C3A C14A C17A 0.2(5) . . . . ?
C2A C3A C14A C17A 176.9(3) . . . . ?
C6A C5A C18A C19A -124.5(4) . . . . ?
C4A C5A C18A C19A 55.6(5) . . . . ?
C6A C5A C18A C20A 114.7(4) . . . . ?
C4A C5A C18A C20A -65.3(4) . . . . ?
C6A C5A C18A C21A -4.2(5) . . . . ?
C4A C5A C18A C21A 175.9(3) . . . . ?
C6B C1B C2B O1B -166.3(19) . . . . ?
C7B C1B C2B O1B -8(2) . . . . ?
C6B C1B C2B C3B 0.0 . . . . ?
C7B C1B C2B C3B 158.2(13) . . . . ?
O1B C2B C3B C4B 169.8(14) . . . . ?
C1B C2B C3B C4B 0.0 . . . . ?
O1B C2B C3B C14B -29.6(15) . . . . ?
C1B C2B C3B C14B 160.6(16) . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C14B C3B C4B C5B -162.6(13) . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C3B C4B C5B C18B -166.7(16) . . . . ?
C4B C5B C6B C1B 0.0 . . . . ?
C18B C5B C6B C1B 166.6(16) . . . . ?
C2B C1B C6B C5B 0.0 . . . . ?
C7B C1B C6B C5B -152.8(14) . . . . ?
C8B N1B C7B C1B -172.4(18) . . . . ?
C2B C1B C7B N1B 167.6(16) . . . . ?
C6B C1B C7B N1B -37(2) . . . . ?
C7B N1B C8B C9B 148.5(19) . . . . ?
C7B N1B C8B C13B -13(3) . . . . ?
C13B C8B C9B C10B 0.0 . . . . ?
N1B C8B C9B C10B -159.9(18) . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C8B C9B C10B N2B -164(2) . . . . ?
O3B N2B C10B C9B 168(2) . . . . ?
O2B N2B C10B C9B -14(3) . . . . ?
O3B N2B C10B C11B 3(3) . . . . ?
O2B N2B C10B C11B -178.7(17) . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
N2B C10B C11B C12B 165(2) . . . . ?
C10B C11B C12B C13B 0.0 . . . . ?
C11B C12B C13B C8B 0.0 . . . . ?
C9B C8B C13B C12B 0.0 . . . . ?
N1B C8B C13B C12B 163.2(15) . . . . ?
C2B C3B C14B C16B -38(2) . . . . ?
C4B C3B C14B C16B 123.5(15) . . . . ?
C2B C3B C14B C15B 61(3) . . . . ?
C4B C3B C14B C15B -137(2) . . . . ?
C2B C3B C14B C17B -158.4(13) . . . . ?
C4B C3B C14B C17B 3.4(12) . . . . ?
C4B C5B C18B C19B 35(3) . . . . ?
C6B C5B C18B C19B -131(3) . . . . ?
C4B C5B C18B C21B 169.7(18) . . . . ?
C6B C5B C18B C21B 3(2) . . . . ?
C4B C5B C18B C20B -74.9(18) . . . . ?
C6B C5B C18B C20B 118.3(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        68.25
_diffrn_measured_fraction_theta_full 0.929
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.078