# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
'Masaki Yamamura'
;
Graduate School of Pure and Applied Sciences,
University of Tsukuba,
1-1-1 Tennodai Tsukuba, Ibaraki, 305-8571, Japan
;
'Yuki Okazaki'
;
Graduate School of Pure and Applied Sciences,
University of Tsukuba,
1-1-1 Tennodai Tsukuba, Ibaraki, 305-8571, Japan
;
'Tatsuya Nabeshima'
;
Graduate School of Pure and Applied Sciences,
University of Tsukuba,
1-1-1 Tennodai Tsukuba, Ibaraki, 305-8571, Japan
;
_publ_contact_author_address     
;
Graduate School of Pure and Applied Sciences,
University of Tsukuba,
1-1-1 Tennodai Tsukuba, Ibaraki, 305-8571, Japan
;
_publ_contact_author_email       nabesima@chem.tsukuba.ac.jp
_publ_contact_author_fax         +81-29-853-4507
_publ_contact_author_phone       +81-29-853-4507

_publ_contact_author_name        'Tatsuya Nabeshima'
_publ_requested_category         FO
_publ_section_title              
;
Locking of Photoisomerization Behavior of Self-assemble Azobenzene-linked Macrocycles with Structural Restriction
;

data_zaki
_database_code_depnum_ccdc_archive 'CCDC 855272'
#TrackingRef '8340_web_deposit_cif_file_0_MasakiYamamura_
#1322022474.azocat100731.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            azoB
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H34 N2 O6'
_chemical_formula_weight         542.61

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.93(7)
_cell_length_b                   9.11(4)
_cell_length_c                   21.95(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.81(18)
_cell_angle_gamma                90.00
_cell_volume                     2857(23)
_cell_formula_units_Z            4
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    7268
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9627
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_process_details   'Rapid AUTO (Rigaku Corp.)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS Rapid'
_diffrn_measurement_method       IP
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            26005
_diffrn_reflns_av_R_equivalents  0.1342
_diffrn_reflns_av_sigmaI/netI    0.1137
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.49
_reflns_number_total             6416
_reflns_number_gt                3977
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid AUTO (Rigaku Corp.)'
_computing_cell_refinement       'Rapid AUTO (Rigaku Corp.)'
_computing_data_reduction        'Rapid AUTO (Rigaku Corp.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.1813P)^2^+0.0000P] 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         6416
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1114
_refine_ls_wR_factor_ref         0.2944
_refine_ls_wR_factor_gt          0.2674
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.16218(14) 0.3983(2) 0.21930(9) 0.0246(5) Uani 1 1 d . . .
O2 O -0.77918(13) 0.3900(2) -0.28588(9) 0.0265(5) Uani 1 1 d . . .
O3 O 0.32393(13) 0.3970(2) 0.31863(9) 0.0271(5) Uani 1 1 d . . .
O4 O -0.61363(13) 0.38688(19) -0.18769(9) 0.0272(5) Uani 1 1 d . . .
H34 H -0.6559 0.3231 -0.1987 0.041 Uiso 1 1 calc R . .
N1 N -0.22676(17) 0.6304(2) 0.04231(11) 0.0273(6) Uani 1 1 d . . .
C1 C -0.57028(19) 0.6203(3) -0.21913(12) 0.0215(6) Uani 1 1 d . . .
C2 C -0.3114(2) 0.6221(3) -0.06264(13) 0.0240(6) Uani 1 1 d . . .
C3 C 0.18371(18) 0.5164(3) 0.26040(11) 0.0204(6) Uani 1 1 d . . .
N2 N -0.22112(16) 0.6262(2) -0.01404(11) 0.0262(5) Uani 1 1 d . . .
C4 C -0.05070(19) 0.5930(3) 0.08067(12) 0.0241(6) Uani 1 1 d . . .
H1 H -0.0485 0.5671 0.0392 0.029 Uiso 1 1 calc R . .
C5 C -0.71972(18) 0.5092(3) -0.27983(12) 0.0231(6) Uani 1 1 d . . .
C6 C 0.14228(19) 0.7550(3) 0.29195(12) 0.0248(6) Uani 1 1 d . . .
H9 H 0.1002 0.8356 0.2861 0.030 Uiso 1 1 calc R . .
C7 C 0.03168(19) 0.6331(3) 0.19436(12) 0.0232(6) Uani 1 1 d . . .
C8 C -0.39709(19) 0.5882(3) -0.05090(12) 0.0248(6) Uani 1 1 d . . .
H2 H -0.3987 0.5674 -0.0088 0.030 Uiso 1 1 calc R . .
C9 C -0.48031(19) 0.5851(3) -0.10159(12) 0.0233(6) Uani 1 1 d . . .
H3 H -0.5376 0.5613 -0.0933 0.028 Uiso 1 1 calc R . .
C10 C -0.13666(19) 0.6312(3) 0.09130(12) 0.0247(6) Uani 1 1 d . . .
C11 C -0.1382(2) 0.6697(3) 0.15284(12) 0.0276(6) Uani 1 1 d . . .
H4 H -0.1959 0.6942 0.1605 0.033 Uiso 1 1 calc R . .
C12 C 0.12011(19) 0.6346(3) 0.24942(12) 0.0225(6) Uani 1 1 d . . .
C13 C -0.3944(2) 0.6497(3) -0.17600(13) 0.0263(6) Uani 1 1 d . . .
H5 H -0.3925 0.6717 -0.2179 0.032 Uiso 1 1 calc R . .
C14 C 0.03149(19) 0.5933(3) 0.13185(12) 0.0235(6) Uani 1 1 d . . .
H6 H 0.0888 0.5661 0.1244 0.028 Uiso 1 1 calc R . .
C15 C 0.2880(2) 0.6394(3) 0.35306(13) 0.0266(6) Uani 1 1 d . . .
H10 H 0.3441 0.6412 0.3873 0.032 Uiso 1 1 calc R . .
C16 C -0.67726(19) 0.7478(3) -0.31038(13) 0.0271(6) Uani 1 1 d . . .
H11 H -0.6912 0.8314 -0.3373 0.033 Uiso 1 1 calc R . .
C17 C 0.26614(18) 0.5186(3) 0.31192(12) 0.0233(6) Uani 1 1 d . . .
C18 C -0.48015(19) 0.6169(3) -0.16520(12) 0.0231(6) Uani 1 1 d . . .
C19 C -0.63530(18) 0.5046(3) -0.22894(12) 0.0222(6) Uani 1 1 d . . .
C20 C -0.7414(2) 0.6306(3) -0.32010(13) 0.0248(6) Uani 1 1 d . . .
H12 H -0.7984 0.6342 -0.3535 0.030 Uiso 1 1 calc R . .
C21 C -0.59289(19) 0.7418(3) -0.26110(12) 0.0250(6) Uani 1 1 d . . .
H13 H -0.5500 0.8211 -0.2558 0.030 Uiso 1 1 calc R . .
C22 C -0.31041(19) 0.6504(3) -0.12525(13) 0.0271(6) Uani 1 1 d . . .
H7 H -0.2527 0.6704 -0.1337 0.032 Uiso 1 1 calc R . .
C23 C 0.2253(2) 0.7576(3) 0.34264(13) 0.0286(6) Uani 1 1 d . . .
H14 H 0.2390 0.8404 0.3701 0.034 Uiso 1 1 calc R . .
C24 C -0.05491(19) 0.6722(3) 0.20341(13) 0.0264(6) Uani 1 1 d . . .
H8 H -0.0571 0.7010 0.2445 0.032 Uiso 1 1 calc R . .
O5 O -0.93634(14) 0.4163(2) -0.38778(9) 0.0321(5) Uani 1 1 d . . .
O6 O 0.48302(13) 0.4312(2) 0.41334(9) 0.0288(5) Uani 1 1 d . . .
C25 C -1.0148(2) 0.5037(3) -0.38178(14) 0.0333(7) Uani 1 1 d . . .
H23 H -0.9985 0.6094 -0.3789 0.040 Uiso 1 1 calc R . .
H24 H -1.0318 0.4753 -0.3431 0.040 Uiso 1 1 calc R . .
C26 C 0.56085(19) 0.5063(3) 0.39925(13) 0.0283(6) Uani 1 1 d . . .
H15 H 0.5511 0.6140 0.3979 0.034 Uiso 1 1 calc R . .
H16 H 0.5675 0.4737 0.3578 0.034 Uiso 1 1 calc R . .
C27 C -1.0962(2) 0.4733(3) -0.44143(15) 0.0400(8) Uani 1 1 d . . .
H25 H -1.0999 0.5497 -0.4741 0.048 Uiso 1 1 calc R . .
H26 H -1.1564 0.4701 -0.4310 0.048 Uiso 1 1 calc R . .
C28 C 0.6479(2) 0.4646(3) 0.45359(14) 0.0355(7) Uani 1 1 d . . .
H17 H 0.7057 0.4727 0.4404 0.043 Uiso 1 1 calc R . .
H18 H 0.6540 0.5260 0.4918 0.043 Uiso 1 1 calc R . .
C29 C -0.9782(2) 0.2818(3) -0.41766(16) 0.0422(8) Uani 1 1 d . . .
H27 H -0.9872 0.2124 -0.3853 0.051 Uiso 1 1 calc R . .
H28 H -0.9373 0.2349 -0.4404 0.051 Uiso 1 1 calc R . .
C30 C 0.5205(2) 0.3091(3) 0.45617(13) 0.0322(7) Uani 1 1 d . . .
H19 H 0.4912 0.2156 0.4375 0.039 Uiso 1 1 calc R . .
H20 H 0.5077 0.3240 0.4976 0.039 Uiso 1 1 calc R . .
C31 C 0.6260(2) 0.3052(3) 0.46525(13) 0.0351(7) Uani 1 1 d . . .
H21 H 0.6606 0.2735 0.5088 0.042 Uiso 1 1 calc R . .
H22 H 0.6415 0.2386 0.4341 0.042 Uiso 1 1 calc R . .
C32 C -1.0729(2) 0.3225(4) -0.46469(16) 0.0434(8) Uani 1 1 d . . .
H29 H -1.1213 0.2491 -0.4635 0.052 Uiso 1 1 calc R . .
H30 H -1.0681 0.3290 -0.5086 0.052 Uiso 1 1 calc R . .
H31 H 0.386(2) 0.413(3) 0.3558(14) 0.031(8) Uiso 1 1 d . . .
H32 H -0.836(2) 0.412(4) -0.3258(16) 0.051(10) Uiso 1 1 d . . .
H35 H 0.206(3) 0.330(5) 0.234(2) 0.095(16) Uiso 1 1 d . . .

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 0.0276(11) 0.0145(9) 0.0300(10) -0.0030(7) 0.0055(8) 0.0009(8)
O2 0.0250(11) 0.0194(10) 0.0328(11) 0.0010(7) 0.0046(8) -0.0036(8)
O3 0.0254(11) 0.0199(10) 0.0326(11) -0.0029(7) 0.0033(8) 0.0039(8)
O4 0.0304(11) 0.0131(9) 0.0343(11) 0.0029(7) 0.0034(8) -0.0053(8)
N1 0.0328(14) 0.0170(12) 0.0309(13) -0.0005(9) 0.0072(10) 0.0019(10)
C1 0.0269(15) 0.0124(12) 0.0271(13) -0.0020(9) 0.0105(11) -0.0020(11)
C2 0.0269(15) 0.0127(12) 0.0314(15) -0.0027(10) 0.0066(11) -0.0004(11)
C3 0.0245(14) 0.0131(13) 0.0254(13) -0.0005(9) 0.0104(11) -0.0013(11)
N2 0.0279(14) 0.0178(11) 0.0314(13) 0.0024(9) 0.0062(10) -0.0007(10)
C4 0.0303(16) 0.0164(13) 0.0252(13) 0.0005(10) 0.0075(11) 0.0040(11)
C5 0.0254(14) 0.0155(13) 0.0293(14) -0.0032(10) 0.0093(11) -0.0043(11)
C6 0.0285(15) 0.0140(13) 0.0323(14) 0.0005(10) 0.0093(12) 0.0041(11)
C7 0.0291(16) 0.0102(12) 0.0306(14) 0.0044(9) 0.0089(12) 0.0003(11)
C8 0.0318(16) 0.0164(13) 0.0268(13) 0.0005(10) 0.0096(11) -0.0015(11)
C9 0.0293(15) 0.0109(12) 0.0305(14) -0.0010(10) 0.0100(11) -0.0024(11)
C10 0.0251(15) 0.0169(13) 0.0306(14) 0.0010(10) 0.0057(11) -0.0005(11)
C11 0.0277(15) 0.0258(15) 0.0303(14) 0.0024(11) 0.0101(11) 0.0047(12)
C12 0.0267(15) 0.0142(12) 0.0293(14) 0.0003(10) 0.0125(11) -0.0008(11)
C13 0.0312(16) 0.0207(14) 0.0277(14) -0.0014(10) 0.0096(11) -0.0036(12)
C14 0.0254(15) 0.0148(13) 0.0317(14) 0.0026(10) 0.0103(11) 0.0026(11)
C15 0.0280(15) 0.0206(14) 0.0296(14) -0.0006(10) 0.0058(11) -0.0007(12)
C16 0.0356(17) 0.0145(13) 0.0316(15) 0.0017(10) 0.0105(12) 0.0014(12)
C17 0.0250(14) 0.0162(13) 0.0294(13) 0.0001(10) 0.0089(11) 0.0012(11)
C18 0.0288(15) 0.0092(12) 0.0315(14) -0.0028(9) 0.0092(11) -0.0010(11)
C19 0.0268(14) 0.0147(12) 0.0261(13) 0.0009(9) 0.0093(11) 0.0041(11)
C20 0.0261(15) 0.0200(13) 0.0286(14) 0.0013(10) 0.0087(11) 0.0026(11)
C21 0.0304(16) 0.0139(12) 0.0310(14) -0.0016(10) 0.0095(11) -0.0022(11)
C22 0.0234(15) 0.0261(15) 0.0320(14) -0.0001(11) 0.0085(11) -0.0029(12)
C23 0.0345(16) 0.0176(13) 0.0333(15) -0.0041(10) 0.0089(12) 0.0011(12)
C24 0.0309(16) 0.0184(13) 0.0309(14) -0.0002(10) 0.0105(11) 0.0018(12)
O5 0.0309(12) 0.0186(10) 0.0417(11) -0.0061(8) 0.0025(9) 0.0009(9)
O6 0.0287(11) 0.0170(10) 0.0375(11) 0.0028(8) 0.0048(8) 0.0010(8)
C25 0.0365(17) 0.0223(15) 0.0399(16) 0.0006(11) 0.0090(13) 0.0056(13)
C26 0.0300(16) 0.0180(14) 0.0353(15) -0.0010(11) 0.0066(12) 0.0002(12)
C27 0.0306(17) 0.0319(18) 0.0520(19) 0.0038(14) 0.0033(14) 0.0025(14)
C28 0.0311(17) 0.0347(17) 0.0392(16) -0.0062(13) 0.0076(12) -0.0015(14)
C29 0.046(2) 0.0211(16) 0.0509(19) -0.0126(13) 0.0005(15) 0.0008(14)
C30 0.0460(19) 0.0152(13) 0.0337(15) 0.0037(11) 0.0087(13) 0.0011(13)
C31 0.0419(18) 0.0297(16) 0.0325(15) 0.0031(12) 0.0089(13) 0.0124(14)
C32 0.0335(18) 0.0369(19) 0.051(2) -0.0106(14) -0.0020(14) -0.0070(15)

_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 C3 1.380(5) . ?
O1 H35 0.89(5) . ?
O2 C5 1.384(5) . ?
O2 H32 1.05(4) . ?
O3 C17 1.385(5) . ?
O3 H31 1.06(3) . ?
O4 C19 1.380(5) . ?
O4 H34 0.8400 . ?
N1 N2 1.265(7) . ?
N1 C10 1.459(7) . ?
C1 C19 1.406(6) . ?
C1 C21 1.417(6) . ?
C1 C18 1.514(7) . ?
C2 C22 1.403(7) . ?
C2 C8 1.410(7) . ?
C2 N2 1.458(7) . ?
C3 C12 1.410(6) . ?
C3 C17 1.410(7) . ?
C4 C14 1.404(7) . ?
C4 C10 1.413(7) . ?
C4 H1 0.9500 . ?
C5 C20 1.393(6) . ?
C5 C19 1.423(7) . ?
C6 C23 1.406(7) . ?
C6 C12 1.415(6) . ?
C6 H9 0.9500 . ?
C7 C24 1.409(7) . ?
C7 C14 1.419(7) . ?
C7 C12 1.510(7) . ?
C8 C9 1.408(7) . ?
C8 H2 0.9500 . ?
C9 C18 1.427(7) . ?
C9 H3 0.9500 . ?
C10 C11 1.402(7) . ?
C11 C24 1.407(7) . ?
C11 H4 0.9500 . ?
C13 C18 1.400(7) . ?
C13 C22 1.416(7) . ?
C13 H5 0.9500 . ?
C14 H6 0.9500 . ?
C15 C23 1.401(6) . ?
C15 C17 1.401(6) . ?
C15 H10 0.9500 . ?
C16 C21 1.404(7) . ?
C16 C20 1.409(6) . ?
C16 H11 0.9500 . ?
C20 H12 0.9500 . ?
C21 H13 0.9500 . ?
C22 H7 0.9500 . ?
C23 H14 0.9500 . ?
C24 H8 0.9500 . ?
O5 C29 1.443(6) . ?
O5 C25 1.453(6) . ?
O6 C26 1.456(6) . ?
O6 C30 1.459(5) . ?
C25 C27 1.533(7) . ?
C25 H23 0.9900 . ?
C25 H24 0.9900 . ?
C26 C28 1.536(7) . ?
C26 H15 0.9900 . ?
C26 H16 0.9900 . ?
C27 C32 1.540(7) . ?
C27 H25 0.9900 . ?
C27 H26 0.9900 . ?
C28 C31 1.526(7) . ?
C28 H17 0.9900 . ?
C28 H18 0.9900 . ?
C29 C32 1.536(7) . ?
C29 H27 0.9900 . ?
C29 H28 0.9900 . ?
C30 C31 1.530(8) . ?
C30 H19 0.9900 . ?
C30 H20 0.9900 . ?
C31 H21 0.9900 . ?
C31 H22 0.9900 . ?
C32 H29 0.9900 . ?
C32 H30 0.9900 . ?

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
C3 O1 H35 107(3) . . ?
C5 O2 H32 105.5(19) . . ?
C17 O3 H31 110.9(16) . . ?
C19 O4 H34 109.5 . . ?
N2 N1 C10 114.4(4) . . ?
C19 C1 C21 117.5(4) . . ?
C19 C1 C18 121.5(3) . . ?
C21 C1 C18 121.0(3) . . ?
C22 C2 C8 119.1(3) . . ?
C22 C2 N2 116.2(4) . . ?
C8 C2 N2 124.6(4) . . ?
O1 C3 C12 117.7(3) . . ?
O1 C3 C17 121.3(3) . . ?
C12 C3 C17 121.0(3) . . ?
N1 N2 C2 114.0(4) . . ?
C14 C4 C10 119.5(4) . . ?
C14 C4 H1 120.2 . . ?
C10 C4 H1 120.2 . . ?
O2 C5 C20 122.4(3) . . ?
O2 C5 C19 116.8(3) . . ?
C20 C5 C19 120.8(3) . . ?
C23 C6 C12 121.3(3) . . ?
C23 C6 H9 119.3 . . ?
C12 C6 H9 119.3 . . ?
C24 C7 C14 117.1(3) . . ?
C24 C7 C12 120.7(4) . . ?
C14 C7 C12 122.2(4) . . ?
C9 C8 C2 120.0(4) . . ?
C9 C8 H2 120.0 . . ?
C2 C8 H2 120.0 . . ?
C8 C9 C18 121.2(4) . . ?
C8 C9 H3 119.4 . . ?
C18 C9 H3 119.4 . . ?
C11 C10 C4 119.3(3) . . ?
C11 C10 N1 116.3(4) . . ?
C4 C10 N1 124.4(4) . . ?
C10 C11 C24 120.5(4) . . ?
C10 C11 H4 119.8 . . ?
C24 C11 H4 119.8 . . ?
C3 C12 C6 117.5(4) . . ?
C3 C12 C7 121.3(3) . . ?
C6 C12 C7 121.3(3) . . ?
C18 C13 C22 120.8(4) . . ?
C18 C13 H5 119.6 . . ?
C22 C13 H5 119.6 . . ?
C4 C14 C7 122.1(4) . . ?
C4 C14 H6 118.9 . . ?
C7 C14 H6 118.9 . . ?
C23 C15 C17 118.6(4) . . ?
C23 C15 H10 120.7 . . ?
C17 C15 H10 120.7 . . ?
C21 C16 C20 120.4(3) . . ?
C21 C16 H11 119.8 . . ?
C20 C16 H11 119.8 . . ?
O3 C17 C15 122.5(3) . . ?
O3 C17 C3 116.5(3) . . ?
C15 C17 C3 121.0(3) . . ?
C13 C18 C9 118.0(3) . . ?
C13 C18 C1 120.8(4) . . ?
C9 C18 C1 121.1(4) . . ?
O4 C19 C1 117.5(3) . . ?
O4 C19 C5 121.6(3) . . ?
C1 C19 C5 120.9(3) . . ?
C5 C20 C16 118.8(4) . . ?
C5 C20 H12 120.6 . . ?
C16 C20 H12 120.6 . . ?
C16 C21 C1 121.6(3) . . ?
C16 C21 H13 119.2 . . ?
C1 C21 H13 119.2 . . ?
C2 C22 C13 120.8(4) . . ?
C2 C22 H7 119.6 . . ?
C13 C22 H7 119.6 . . ?
C15 C23 C6 120.7(3) . . ?
C15 C23 H14 119.7 . . ?
C6 C23 H14 119.7 . . ?
C11 C24 C7 121.5(4) . . ?
C11 C24 H8 119.3 . . ?
C7 C24 H8 119.3 . . ?
C29 O5 C25 104.6(4) . . ?
C26 O6 C30 108.3(3) . . ?
O5 C25 C27 106.5(4) . . ?
O5 C25 H23 110.4 . . ?
C27 C25 H23 110.4 . . ?
O5 C25 H24 110.4 . . ?
C27 C25 H24 110.4 . . ?
H23 C25 H24 108.6 . . ?
O6 C26 C28 105.4(4) . . ?
O6 C26 H15 110.7 . . ?
C28 C26 H15 110.7 . . ?
O6 C26 H16 110.7 . . ?
C28 C26 H16 110.7 . . ?
H15 C26 H16 108.8 . . ?
C25 C27 C32 104.2(3) . . ?
C25 C27 H25 110.9 . . ?
C32 C27 H25 110.9 . . ?
C25 C27 H26 110.9 . . ?
C32 C27 H26 110.9 . . ?
H25 C27 H26 108.9 . . ?
C31 C28 C26 101.1(3) . . ?
C31 C28 H17 111.6 . . ?
C26 C28 H17 111.6 . . ?
C31 C28 H18 111.6 . . ?
C26 C28 H18 111.6 . . ?
H17 C28 H18 109.4 . . ?
O5 C29 C32 107.1(3) . . ?
O5 C29 H27 110.3 . . ?
C32 C29 H27 110.3 . . ?
O5 C29 H28 110.3 . . ?
C32 C29 H28 110.3 . . ?
H27 C29 H28 108.5 . . ?
O6 C30 C31 106.9(3) . . ?
O6 C30 H19 110.3 . . ?
C31 C30 H19 110.3 . . ?
O6 C30 H20 110.3 . . ?
C31 C30 H20 110.3 . . ?
H19 C30 H20 108.6 . . ?
C28 C31 C30 102.6(2) . . ?
C28 C31 H21 111.2 . . ?
C30 C31 H21 111.2 . . ?
C28 C31 H22 111.2 . . ?
C30 C31 H22 111.2 . . ?
H21 C31 H22 109.2 . . ?
C29 C32 C27 104.1(3) . . ?
C29 C32 H29 110.9 . . ?
C27 C32 H29 110.9 . . ?
C29 C32 H30 110.9 . . ?
C27 C32 H30 110.9 . . ?
H29 C32 H30 108.9 . . ?

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
C10 N1 N2 C2 178.7(2) . . . . ?
C22 C2 N2 N1 166.2(2) . . . . ?
C8 C2 N2 N1 -15.6(3) . . . . ?
C22 C2 C8 C9 -0.9(4) . . . . ?
N2 C2 C8 C9 -179.0(2) . . . . ?
C2 C8 C9 C18 -0.5(4) . . . . ?
C14 C4 C10 C11 0.3(4) . . . . ?
C14 C4 C10 N1 -178.1(2) . . . . ?
N2 N1 C10 C11 165.7(2) . . . . ?
N2 N1 C10 C4 -15.8(3) . . . . ?
C4 C10 C11 C24 0.9(4) . . . . ?
N1 C10 C11 C24 179.4(2) . . . . ?
O1 C3 C12 C6 179.6(2) . . . . ?
C17 C3 C12 C6 0.0(4) . . . . ?
O1 C3 C12 C7 -0.4(3) . . . . ?
C17 C3 C12 C7 -180.0(2) . . . . ?
C23 C6 C12 C3 1.0(4) . . . . ?
C23 C6 C12 C7 -179.0(2) . . . . ?
C24 C7 C12 C3 133.3(3) . . . . ?
C14 C7 C12 C3 -46.9(3) . . . . ?
C24 C7 C12 C6 -46.7(3) . . . . ?
C14 C7 C12 C6 133.0(3) . . . . ?
C10 C4 C14 C7 -0.9(4) . . . . ?
C24 C7 C14 C4 0.2(4) . . . . ?
C12 C7 C14 C4 -179.5(2) . . . . ?
C23 C15 C17 O3 180.0(2) . . . . ?
C23 C15 C17 C3 1.1(4) . . . . ?
O1 C3 C17 O3 0.4(3) . . . . ?
C12 C3 C17 O3 179.9(2) . . . . ?
O1 C3 C17 C15 179.3(2) . . . . ?
C12 C3 C17 C15 -1.1(4) . . . . ?
C22 C13 C18 C9 0.3(4) . . . . ?
C22 C13 C18 C1 178.2(2) . . . . ?
C8 C9 C18 C13 0.8(4) . . . . ?
C8 C9 C18 C1 -177.2(2) . . . . ?
C19 C1 C18 C13 132.1(3) . . . . ?
C21 C1 C18 C13 -48.9(3) . . . . ?
C19 C1 C18 C9 -50.1(3) . . . . ?
C21 C1 C18 C9 129.0(3) . . . . ?
C21 C1 C19 O4 -179.4(2) . . . . ?
C18 C1 C19 O4 -0.4(4) . . . . ?
C21 C1 C19 C5 1.0(4) . . . . ?
C18 C1 C19 C5 -180.0(2) . . . . ?
O2 C5 C19 O4 0.2(3) . . . . ?
C20 C5 C19 O4 178.5(2) . . . . ?
O2 C5 C19 C1 179.7(2) . . . . ?
C20 C5 C19 C1 -2.0(4) . . . . ?
O2 C5 C20 C16 179.6(2) . . . . ?
C19 C5 C20 C16 1.3(4) . . . . ?
C21 C16 C20 C5 0.2(4) . . . . ?
C20 C16 C21 C1 -1.2(4) . . . . ?
C19 C1 C21 C16 0.5(4) . . . . ?
C18 C1 C21 C16 -178.5(2) . . . . ?
C8 C2 C22 C13 2.0(4) . . . . ?
N2 C2 C22 C13 -179.8(2) . . . . ?
C18 C13 C22 C2 -1.7(4) . . . . ?
C17 C15 C23 C6 0.0(4) . . . . ?
C12 C6 C23 C15 -1.0(4) . . . . ?
C10 C11 C24 C7 -1.6(4) . . . . ?
C14 C7 C24 C11 1.0(4) . . . . ?
C12 C7 C24 C11 -179.2(2) . . . . ?
C29 O5 C25 C27 -36.5(3) . . . . ?
C30 O6 C26 C28 -21.2(3) . . . . ?
O5 C25 C27 C32 23.3(3) . . . . ?
O6 C26 C28 C31 36.9(3) . . . . ?
C25 O5 C29 C32 35.3(4) . . . . ?
C26 O6 C30 C31 -3.4(3) . . . . ?
C26 C28 C31 C30 -37.8(3) . . . . ?
O6 C30 C31 C28 26.5(3) . . . . ?
O5 C29 C32 C27 -20.2(4) . . . . ?
C25 C27 C32 C29 -2.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.177