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

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Jung, Suhyun'
'Kim, Youngmee'
'Kim, Sung-Jin'
'Kwon, Tae-Hwan'
'Huh, Seong'
'Park, Seongsoon'

_publ_contact_author_name        'Park, Seongsoon'
_publ_contact_author_email       spark@sungshin.ac.kr

_publ_section_title              
;
Bio-functionalization of metal-organic frameworks
by covalent protein conjugation
;

# Attachment '- CIF_1D.cif'

data_yk372sadcc
_database_code_depnum_ccdc_archive 'CCDC 789848'
#TrackingRef '- CIF_1D.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 In N O8'
_chemical_formula_weight         573.29

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'
In In -0.7276 1.3100 '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   Cc

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

_cell_length_a                   19.192(4)
_cell_length_b                   8.7720(18)
_cell_length_c                   16.666(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.71(3)
_cell_angle_gamma                90.00
_cell_volume                     2412.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1228
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      20.42

_exptl_crystal_description       needle
_exptl_crystal_colour            coloeless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Bruker SMART CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6523
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3280
_reflns_number_gt                2337
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0400P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3280
_refine_ls_number_parameters     309
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.001
_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
In1 In 0.22804(16) -0.16236(5) 0.16884(19) 0.05246(16) Uani 1 1 d . . .
O1 O 0.3270(8) -0.3419(15) 0.2394(10) 0.070(4) Uani 1 1 d . . .
O8 O 0.1323(7) -0.3483(12) 0.0944(10) 0.059(4) Uani 1 1 d . . .
C12 C 0.4018(13) 0.167(2) 0.2247(14) 0.073(6) Uani 1 1 d . . .
H12A H 0.4031 0.2414 0.2685 0.087 Uiso 1 1 calc R . .
H12B H 0.4548 0.1190 0.2551 0.087 Uiso 1 1 calc R . .
C14 C 0.3440(11) 0.362(2) 0.1007(13) 0.057(5) Uani 1 1 d . . .
H14 H 0.3117 0.3969 0.1236 0.068 Uiso 1 1 calc R . .
C17 C 0.1401(10) -0.3496(17) 0.0211(12) 0.047(4) Uani 1 1 d . . .
C1 C 0.3126(11) -0.3464(17) 0.2995(13) 0.058(5) Uani 1 1 d . . .
O2 O 0.2592(7) -0.2727(16) 0.3087(8) 0.069(4) Uani 1 1 d . . .
O7 O 0.1988(6) -0.2678(15) 0.0320(8) 0.062(4) Uani 1 1 d . . .
C4 C 0.0487(12) 0.1777(16) 0.0997(14) 0.058(5) Uani 1 1 d . . .
H4A H -0.0045 0.1331 0.0606 0.070 Uiso 1 1 calc R . .
H4B H 0.0573 0.2554 0.0641 0.070 Uiso 1 1 calc R . .
C5 C 0.0565(9) 0.2496(15) 0.1928(10) 0.048(4) Uani 1 1 d . . .
C13 C 0.3962(9) 0.252(2) 0.1490(11) 0.054(4) Uani 1 1 d . . .
C8 C 0.0785(8) 0.381(2) 0.3571(12) 0.047(4) Uani 1 1 d . . .
C6 C 0.1185(10) 0.3627(18) 0.2376(13) 0.054(5) Uani 1 1 d . . .
H6 H 0.1514 0.3927 0.2144 0.065 Uiso 1 1 calc R . .
C2 C 0.3707(9) -0.440(2) 0.3971(12) 0.068(5) Uani 1 1 d . . .
H2A H 0.3502 -0.5438 0.3876 0.082 Uiso 1 1 calc R . .
H2B H 0.4242 -0.4460 0.4047 0.082 Uiso 1 1 calc R . .
C10 C 0.0096(8) 0.2144(18) 0.2285(13) 0.051(4) Uani 1 1 d . . .
H10 H -0.0287 0.1380 0.1986 0.061 Uiso 1 1 calc R . .
O5 O 0.3324(8) -0.0097(15) 0.2711(9) 0.097(4) Uani 1 1 d . . .
C9 C 0.0127(10) 0.279(2) 0.3026(12) 0.057(4) Uani 1 1 d . . .
H9 H -0.0262 0.2576 0.3185 0.068 Uiso 1 1 calc R . .
O6 O 0.3074(9) -0.0139(18) 0.1327(10) 0.091(4) Uani 1 1 d . . .
C11 C 0.3432(8) 0.0463(12) 0.2159(11) 0.048(4) Uani 1 1 d . . .
O4 O 0.1276(8) 0.0134(19) 0.0671(8) 0.121(6) Uani 1 1 d . . .
C15 C 0.3327(8) 0.4275(16) 0.0235(11) 0.049(4) Uani 1 1 d . . .
H15 H 0.2923 0.5003 -0.0069 0.059 Uiso 1 1 calc R . .
C3 C 0.1175(11) 0.050(2) 0.1352(13) 0.081(6) Uani 1 1 d . . .
C7 C 0.1258(10) 0.4266(19) 0.3218(11) 0.062(5) Uani 1 1 d . . .
H7 H 0.1645 0.5018 0.3533 0.074 Uiso 1 1 calc R . .
O3 O 0.1558(7) -0.0072(16) 0.2068(9) 0.082(4) Uani 1 1 d . . .
C18 C 0.0943(11) -0.453(2) -0.0516(11) 0.071(5) Uani 1 1 d . . .
H18A H 0.0434 -0.4741 -0.0548 0.085 Uiso 1 1 calc R . .
H18B H 0.1238 -0.5476 -0.0405 0.085 Uiso 1 1 calc R . .
C21 C 0.3817(10) 0.387(2) -0.0116(12) 0.055(4) Uani 1 1 d . . .
C20 C 0.4348(11) 0.278(2) 0.0348(14) 0.066(5) Uani 1 1 d . . .
H20 H 0.4657 0.2431 0.0100 0.079 Uiso 1 1 calc R . .
C19 C 0.4491(11) 0.209(2) 0.1189(15) 0.075(6) Uani 1 1 d . . .
H19 H 0.4910 0.1395 0.1517 0.091 Uiso 1 1 calc R . .
N1S N 0.2578(11) 1.0175(12) 0.9378(11) 0.107(7) Uani 1 1 d . . .
H1S1 H 0.2686 1.0923 0.9088 0.128 Uiso 1 1 calc R . .
H1S2 H 0.2825 1.0401 0.9990 0.128 Uiso 1 1 calc R . .
C2S C 0.2858(5) 0.8798(13) 0.9254(7) 0.058(3) Uani 1 1 d . . .
H2S1 H 0.2639 0.8624 0.8593 0.070 Uiso 1 1 calc R . .
H2S2 H 0.2672 0.7982 0.9490 0.070 Uiso 1 1 calc R . .
C4S C 0.1315(9) 1.1663(14) 0.8971(10) 0.086(4) Uani 1 1 d . . .
H4S1 H 0.1585 1.2114 0.9581 0.129 Uiso 1 1 calc R . .
H4S2 H 0.0755 1.1492 0.8772 0.129 Uiso 1 1 calc R . .
H4S3 H 0.1351 1.2337 0.8539 0.129 Uiso 1 1 calc R . .
C1S C 0.3766(6) 0.8776(12) 0.9751(8) 0.079(3) Uani 1 1 d . . .
H1S3 H 0.3951 0.9575 0.9510 0.119 Uiso 1 1 calc R . .
H1S4 H 0.3945 0.7809 0.9653 0.119 Uiso 1 1 calc R . .
H1S5 H 0.3983 0.8931 1.0406 0.119 Uiso 1 1 calc R . .
C3S C 0.1743(14) 1.005(3) 0.9004(11) 0.158(12) Uani 1 1 d . . .
H3S1 H 0.1641 0.9332 0.9374 0.189 Uiso 1 1 calc R . .
H3S2 H 0.1497 0.9645 0.8375 0.189 Uiso 1 1 calc 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
In1 0.0547(3) 0.0659(3) 0.0369(2) 0.0005(8) 0.02345(18) -0.0013(8)
O1 0.075(8) 0.099(11) 0.047(8) 0.007(5) 0.039(7) 0.000(6)
O8 0.073(8) 0.064(8) 0.045(8) 0.000(5) 0.035(7) -0.014(5)
C12 0.057(9) 0.097(13) 0.028(6) -0.007(6) -0.005(5) -0.005(8)
C14 0.058(10) 0.080(12) 0.052(10) -0.019(9) 0.042(9) -0.013(8)
C17 0.057(8) 0.066(8) 0.032(6) 0.001(5) 0.033(6) 0.014(6)
C1 0.058(8) 0.042(7) 0.044(9) 0.003(6) 0.005(6) 0.014(6)
O2 0.076(9) 0.090(10) 0.050(8) 0.013(7) 0.039(7) 0.007(8)
O7 0.052(7) 0.075(8) 0.062(9) -0.024(7) 0.032(7) -0.032(7)
C4 0.071(10) 0.039(8) 0.048(9) 0.003(5) 0.019(7) 0.019(6)
C5 0.056(10) 0.020(6) 0.041(8) 0.005(6) 0.005(7) 0.011(6)
C13 0.037(9) 0.078(10) 0.043(9) -0.008(8) 0.018(8) -0.003(8)
C8 0.029(6) 0.061(9) 0.042(8) 0.025(7) 0.013(6) 0.025(7)
C6 0.041(8) 0.051(10) 0.059(11) -0.004(7) 0.016(7) -0.007(7)
C2 0.060(8) 0.062(10) 0.074(11) 0.018(8) 0.028(7) 0.021(7)
C10 0.028(7) 0.060(9) 0.061(9) 0.002(7) 0.020(7) 0.003(6)
O5 0.144(11) 0.070(6) 0.120(10) 0.008(6) 0.099(9) -0.015(6)
C9 0.048(8) 0.063(10) 0.062(10) 0.011(8) 0.031(7) -0.002(7)
O6 0.108(9) 0.101(10) 0.062(9) -0.007(7) 0.041(8) -0.038(7)
C11 0.051(7) 0.019(5) 0.052(8) -0.004(5) 0.010(6) -0.015(5)
O4 0.154(12) 0.165(13) 0.065(8) 0.043(7) 0.070(8) 0.081(9)
C15 0.044(8) 0.041(9) 0.058(10) -0.019(7) 0.022(7) 0.001(6)
C3 0.078(11) 0.127(14) 0.059(9) -0.032(9) 0.049(9) -0.037(10)
C7 0.063(10) 0.066(11) 0.049(9) -0.020(7) 0.022(8) -0.010(8)
O3 0.081(8) 0.081(9) 0.045(8) -0.005(6) 0.005(6) 0.042(6)
C18 0.108(12) 0.067(10) 0.055(9) -0.012(7) 0.054(8) -0.026(8)
C21 0.086(11) 0.041(8) 0.043(8) -0.011(7) 0.037(8) -0.019(9)
C20 0.044(8) 0.065(11) 0.092(13) -0.025(10) 0.037(9) -0.010(8)
C19 0.075(11) 0.063(10) 0.055(9) 0.000(7) 0.009(8) 0.026(8)
N1S 0.23(2) 0.033(6) 0.071(10) -0.006(5) 0.091(13) -0.041(8)
C2S 0.032(5) 0.090(9) 0.049(5) -0.002(5) 0.018(5) 0.000(5)
C4S 0.081(11) 0.075(8) 0.105(10) 0.015(7) 0.049(10) 0.011(8)
C1S 0.059(6) 0.078(8) 0.074(7) 0.001(5) 0.015(5) 0.029(5)
C3S 0.194(19) 0.20(2) 0.039(7) -0.045(10) 0.032(9) -0.174(19)

_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
In1 O7 2.250(11) . ?
In1 O3 2.251(13) . ?
In1 O1 2.278(14) . ?
In1 O5 2.285(14) . ?
In1 O8 2.291(12) . ?
In1 O2 2.304(11) . ?
In1 O6 2.306(14) . ?
In1 O4 2.373(13) . ?
In1 C1 2.524(16) . ?
In1 C3 2.66(2) . ?
In1 C11 2.660(10) . ?
O1 C1 1.17(2) . ?
O8 C17 1.30(2) . ?
C12 C13 1.42(3) . ?
C12 C11 1.50(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.32(2) . ?
C14 C13 1.33(2) . ?
C14 H14 0.9300 . ?
C17 O7 1.268(18) . ?
C17 C18 1.40(2) . ?
C1 O2 1.286(19) . ?
C1 C2 1.65(2) . ?
C4 C3 1.60(3) . ?
C4 C5 1.61(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.34(2) . ?
C5 C6 1.43(2) . ?
C13 C19 1.40(2) . ?
C8 C7 1.37(2) . ?
C8 C9 1.44(2) . ?
C8 C18 1.52(3) 2 ?
C6 C7 1.45(2) . ?
C6 H6 0.9300 . ?
C2 C21 1.50(3) 2 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 C9 1.33(2) . ?
C10 H10 0.9300 . ?
O5 C11 1.15(2) . ?
C9 H9 0.9300 . ?
O6 C11 1.303(19) . ?
O4 C3 1.28(2) . ?
C15 C21 1.38(2) . ?
C15 H15 0.9300 . ?
C3 O3 1.15(2) . ?
C7 H7 0.9300 . ?
C18 C8 1.52(3) 2_554 ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C21 C20 1.32(3) . ?
C21 C2 1.50(3) 2_554 ?
C20 C19 1.42(3) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
N1S C2S 1.379(17) . ?
N1S C3S 1.40(2) . ?
N1S H1S1 0.9000 . ?
N1S H1S2 0.9000 . ?
C2S C1S 1.499(12) . ?
C2S H2S1 0.9700 . ?
C2S H2S2 0.9700 . ?
C4S C3S 1.62(3) . ?
C4S H4S1 0.9600 . ?
C4S H4S2 0.9600 . ?
C4S H4S3 0.9600 . ?
C1S H1S3 0.9600 . ?
C1S H1S4 0.9600 . ?
C1S H1S5 0.9600 . ?
C3S H3S1 0.9700 . ?
C3S H3S2 0.9700 . ?

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
O7 In1 O3 131.5(4) . . ?
O7 In1 O1 87.1(5) . . ?
O3 In1 O1 138.0(5) . . ?
O7 In1 O5 131.8(4) . . ?
O3 In1 O5 82.4(4) . . ?
O1 In1 O5 80.7(5) . . ?
O7 In1 O8 56.1(4) . . ?
O3 In1 O8 98.3(5) . . ?
O1 In1 O8 90.80(19) . . ?
O5 In1 O8 167.5(5) . . ?
O7 In1 O2 130.87(16) . . ?
O3 In1 O2 81.3(5) . . ?
O1 In1 O2 58.0(5) . . ?
O5 In1 O2 79.4(5) . . ?
O8 In1 O2 88.3(5) . . ?
O7 In1 O6 79.9(5) . . ?
O3 In1 O6 108.4(2) . . ?
O1 In1 O6 92.2(5) . . ?
O5 In1 O6 54.5(5) . . ?
O8 In1 O6 135.6(5) . . ?
O2 In1 O6 129.6(5) . . ?
O7 In1 O4 81.5(5) . . ?
O3 In1 O4 54.3(4) . . ?
O1 In1 O4 167.7(5) . . ?
O5 In1 O4 103.6(3) . . ?
O8 In1 O4 86.6(6) . . ?
O2 In1 O4 133.8(4) . . ?
O6 In1 O4 81.4(5) . . ?
O7 In1 C1 109.2(5) . . ?
O3 In1 C1 111.2(6) . . ?
O1 In1 C1 27.5(6) . . ?
O5 In1 C1 78.4(5) . . ?
O8 In1 C1 89.8(5) . . ?
O2 In1 C1 30.4(5) . . ?
O6 In1 C1 111.5(6) . . ?
O4 In1 C1 164.1(5) . . ?
O7 In1 C3 108.4(5) . . ?
O3 In1 C3 25.4(5) . . ?
O1 In1 C3 163.4(5) . . ?
O5 In1 C3 92.8(5) . . ?
O8 In1 C3 93.0(5) . . ?
O2 In1 C3 106.0(5) . . ?
O6 In1 C3 96.4(6) . . ?
O4 In1 C3 28.9(5) . . ?
C1 In1 C3 136.2(6) . . ?
O7 In1 C11 108.8(4) . . ?
O3 In1 C11 92.2(5) . . ?
O1 In1 C11 88.6(5) . . ?
O5 In1 C11 25.5(5) . . ?
O8 In1 C11 164.8(5) . . ?
O2 In1 C11 104.1(5) . . ?
O6 In1 C11 29.3(5) . . ?
O4 In1 C11 90.7(5) . . ?
C1 In1 C11 96.6(5) . . ?
C3 In1 C11 91.9(2) . . ?
C1 O1 In1 88.1(11) . . ?
C17 O8 In1 94.0(10) . . ?
C13 C12 C11 124.8(16) . . ?
C13 C12 H12A 106.1 . . ?
C11 C12 H12A 106.1 . . ?
C13 C12 H12B 106.1 . . ?
C11 C12 H12B 106.1 . . ?
H12A C12 H12B 106.3 . . ?
C15 C14 C13 127.2(16) . . ?
C15 C14 H14 116.4 . . ?
C13 C14 H14 116.4 . . ?
O7 C17 O8 112.3(16) . . ?
O7 C17 C18 127.3(14) . . ?
O8 C17 C18 119.6(15) . . ?
O1 C1 O2 129.6(17) . . ?
O1 C1 C2 121.7(17) . . ?
O2 C1 C2 108.2(15) . . ?
O1 C1 In1 64.4(11) . . ?
O2 C1 In1 65.3(8) . . ?
C2 C1 In1 169.8(12) . . ?
C1 O2 In1 84.3(10) . . ?
C17 O7 In1 97.0(10) . . ?
C3 C4 C5 105.4(13) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C10 C5 C6 119.7(16) . . ?
C10 C5 C4 125.7(14) . . ?
C6 C5 C4 114.6(15) . . ?
C14 C13 C19 116.1(17) . . ?
C14 C13 C12 127.8(17) . . ?
C19 C13 C12 116.0(18) . . ?
C7 C8 C9 118.1(17) . . ?
C7 C8 C18 118.2(17) . 2 ?
C9 C8 C18 123.5(15) . 2 ?
C5 C6 C7 114.6(16) . . ?
C5 C6 H6 122.7 . . ?
C7 C6 H6 122.7 . . ?
C21 C2 C1 121.2(15) 2 . ?
C21 C2 H2A 107.0 2 . ?
C1 C2 H2A 107.0 . . ?
C21 C2 H2B 107.0 2 . ?
C1 C2 H2B 107.0 . . ?
H2A C2 H2B 106.8 . . ?
C9 C10 C5 126.2(17) . . ?
C9 C10 H10 116.9 . . ?
C5 C10 H10 116.9 . . ?
C11 O5 In1 95.8(10) . . ?
C10 C9 C8 117.5(16) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C11 O6 In1 90.6(10) . . ?
O5 C11 O6 117.8(12) . . ?
O5 C11 C12 131.0(15) . . ?
O6 C11 C12 110.6(15) . . ?
O5 C11 In1 58.7(8) . . ?
O6 C11 In1 60.1(7) . . ?
C12 C11 In1 170.2(12) . . ?
C3 O4 In1 88.0(12) . . ?
C14 C15 C21 119.4(16) . . ?
C14 C15 H15 120.3 . . ?
C21 C15 H15 120.3 . . ?
O3 C3 O4 120.3(19) . . ?
O3 C3 C4 131.3(17) . . ?
O4 C3 C4 108.5(17) . . ?
O3 C3 In1 57.1(11) . . ?
O4 C3 In1 63.2(10) . . ?
C4 C3 In1 171.6(12) . . ?
C8 C7 C6 123.2(16) . . ?
C8 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
C3 O3 In1 97.5(13) . . ?
C17 C18 C8 108.4(15) . 2_554 ?
C17 C18 H18A 110.0 . . ?
C8 C18 H18A 110.0 2_554 . ?
C17 C18 H18B 110.0 . . ?
C8 C18 H18B 110.0 2_554 . ?
H18A C18 H18B 108.4 . . ?
C20 C21 C15 115.3(17) . . ?
C20 C21 C2 119.1(17) . 2_554 ?
C15 C21 C2 125.1(18) . 2_554 ?
C21 C20 C19 126.1(18) . . ?
C21 C20 H20 117.0 . . ?
C19 C20 H20 117.0 . . ?
C13 C19 C20 115.5(17) . . ?
C13 C19 H19 122.3 . . ?
C20 C19 H19 122.3 . . ?
C2S N1S C3S 108.1(10) . . ?
C2S N1S H1S1 110.1 . . ?
C3S N1S H1S1 110.1 . . ?
C2S N1S H1S2 110.1 . . ?
C3S N1S H1S2 110.1 . . ?
H1S1 N1S H1S2 108.4 . . ?
N1S C2S C1S 111.1(11) . . ?
N1S C2S H2S1 109.4 . . ?
C1S C2S H2S1 109.4 . . ?
N1S C2S H2S2 109.4 . . ?
C1S C2S H2S2 109.4 . . ?
H2S1 C2S H2S2 108.0 . . ?
C3S C4S H4S1 109.5 . . ?
C3S C4S H4S2 109.5 . . ?
H4S1 C4S H4S2 109.5 . . ?
C3S C4S H4S3 109.5 . . ?
H4S1 C4S H4S3 109.5 . . ?
H4S2 C4S H4S3 109.5 . . ?
C2S C1S H1S3 109.5 . . ?
C2S C1S H1S4 109.5 . . ?
H1S3 C1S H1S4 109.5 . . ?
C2S C1S H1S5 109.5 . . ?
H1S3 C1S H1S5 109.5 . . ?
H1S4 C1S H1S5 109.5 . . ?
N1S C3S C4S 113.2(11) . . ?
N1S C3S H3S1 108.9 . . ?
C4S C3S H3S1 108.9 . . ?
N1S C3S H3S2 108.9 . . ?
C4S C3S H3S2 108.9 . . ?
H3S1 C3S H3S2 107.8 . . ?

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
O7 In1 O1 C1 -144.0(12) . . . . ?
O3 In1 O1 C1 15.4(15) . . . . ?
O5 In1 O1 C1 82.8(12) . . . . ?
O8 In1 O1 C1 -88.0(13) . . . . ?
O2 In1 O1 C1 -0.4(11) . . . . ?
O6 In1 O1 C1 136.3(12) . . . . ?
O4 In1 O1 C1 -166(3) . . . . ?
C3 In1 O1 C1 15(3) . . . . ?
C11 In1 O1 C1 107.2(12) . . . . ?
O7 In1 O8 C17 -4.8(9) . . . . ?
O3 In1 O8 C17 130.4(10) . . . . ?
O1 In1 O8 C17 -90.8(10) . . . . ?
O5 In1 O8 C17 -137(2) . . . . ?
O2 In1 O8 C17 -148.7(10) . . . . ?
O6 In1 O8 C17 3.2(13) . . . . ?
O4 In1 O8 C17 77.2(10) . . . . ?
C1 In1 O8 C17 -118.3(11) . . . . ?
C3 In1 O8 C17 105.4(11) . . . . ?
C11 In1 O8 C17 -3(2) . . . . ?
In1 O8 C17 O7 7.6(15) . . . . ?
In1 O8 C17 C18 178.1(15) . . . . ?
In1 O1 C1 O2 1(2) . . . . ?
In1 O1 C1 C2 -170.6(16) . . . . ?
O7 In1 C1 O1 38.5(13) . . . . ?
O3 In1 C1 O1 -169.0(11) . . . . ?
O5 In1 C1 O1 -92.0(12) . . . . ?
O8 In1 C1 O1 92.1(12) . . . . ?
O2 In1 C1 O1 179.3(19) . . . . ?
O6 In1 C1 O1 -47.9(12) . . . . ?
O4 In1 C1 O1 169.0(19) . . . . ?
C3 In1 C1 O1 -173.8(11) . . . . ?
C11 In1 C1 O1 -74.1(12) . . . . ?
O7 In1 C1 O2 -140.8(10) . . . . ?
O3 In1 C1 O2 11.7(12) . . . . ?
O1 In1 C1 O2 -179.3(19) . . . . ?
O5 In1 C1 O2 88.7(10) . . . . ?
O8 In1 C1 O2 -87.1(10) . . . . ?
O6 In1 C1 O2 132.8(10) . . . . ?
O4 In1 C1 O2 -10(3) . . . . ?
C3 In1 C1 O2 7.0(14) . . . . ?
C11 In1 C1 O2 106.7(10) . . . . ?
O7 In1 C1 C2 167(7) . . . . ?
O3 In1 C1 C2 -40(7) . . . . ?
O1 In1 C1 C2 129(8) . . . . ?
O5 In1 C1 C2 37(7) . . . . ?
O8 In1 C1 C2 -139(7) . . . . ?
O2 In1 C1 C2 -52(7) . . . . ?
O6 In1 C1 C2 81(7) . . . . ?
O4 In1 C1 C2 -62(8) . . . . ?
C3 In1 C1 C2 -45(8) . . . . ?
C11 In1 C1 C2 55(7) . . . . ?
O1 C1 O2 In1 -1(2) . . . . ?
C2 C1 O2 In1 171.5(13) . . . . ?
O7 In1 O2 C1 52.1(13) . . . . ?
O3 In1 O2 C1 -169.0(11) . . . . ?
O1 In1 O2 C1 0.4(10) . . . . ?
O5 In1 O2 C1 -85.1(11) . . . . ?
O8 In1 O2 C1 92.4(11) . . . . ?
O6 In1 O2 C1 -62.3(13) . . . . ?
O4 In1 O2 C1 176.1(10) . . . . ?
C3 In1 O2 C1 -175.0(10) . . . . ?
C11 In1 O2 C1 -78.8(11) . . . . ?
O8 C17 O7 In1 -7.8(15) . . . . ?
C18 C17 O7 In1 -177.4(18) . . . . ?
O3 In1 O7 C17 -63.8(13) . . . . ?
O1 In1 O7 C17 97.8(11) . . . . ?
O5 In1 O7 C17 172.6(10) . . . . ?
O8 In1 O7 C17 4.9(10) . . . . ?
O2 In1 O7 C17 56.0(14) . . . . ?
O6 In1 O7 C17 -169.5(11) . . . . ?
O4 In1 O7 C17 -86.8(11) . . . . ?
C1 In1 O7 C17 81.1(9) . . . . ?
C3 In1 O7 C17 -76.0(11) . . . . ?
C11 In1 O7 C17 -174.6(10) . . . . ?
C3 C4 C5 C10 -99.9(18) . . . . ?
C3 C4 C5 C6 81.6(17) . . . . ?
C15 C14 C13 C19 5(3) . . . . ?
C15 C14 C13 C12 -171.2(17) . . . . ?
C11 C12 C13 C14 73(3) . . . . ?
C11 C12 C13 C19 -104(2) . . . . ?
C10 C5 C6 C7 2(2) . . . . ?
C4 C5 C6 C7 -179.6(12) . . . . ?
O1 C1 C2 C21 147.6(18) . . . 2 ?
O2 C1 C2 C21 -26(2) . . . 2 ?
In1 C1 C2 C21 23(8) . . . 2 ?
C6 C5 C10 C9 2(3) . . . . ?
C4 C5 C10 C9 -176.3(15) . . . . ?
O7 In1 O5 C11 29.1(14) . . . . ?
O3 In1 O5 C11 -111.9(12) . . . . ?
O1 In1 O5 C11 106.7(11) . . . . ?
O8 In1 O5 C11 154(2) . . . . ?
O2 In1 O5 C11 165.6(12) . . . . ?
O6 In1 O5 C11 7.3(11) . . . . ?
O4 In1 O5 C11 -61.5(13) . . . . ?
C1 In1 O5 C11 134.6(12) . . . . ?
C3 In1 O5 C11 -88.6(10) . . . . ?
C5 C10 C9 C8 -8(3) . . . . ?
C7 C8 C9 C10 10(3) . . . . ?
C18 C8 C9 C10 -174.4(16) 2 . . . ?
O7 In1 O6 C11 -170.0(11) . . . . ?
O3 In1 O6 C11 59.5(12) . . . . ?
O1 In1 O6 C11 -83.3(11) . . . . ?
O5 In1 O6 C11 -6.4(9) . . . . ?
O8 In1 O6 C11 -176.6(9) . . . . ?
O2 In1 O6 C11 -34.4(13) . . . . ?
O4 In1 O6 C11 107.2(11) . . . . ?
C1 In1 O6 C11 -63.2(11) . . . . ?
C3 In1 O6 C11 82.5(9) . . . . ?
In1 O5 C11 O6 -11.9(18) . . . . ?
In1 O5 C11 C12 178.4(17) . . . . ?
In1 O6 C11 O5 11.7(18) . . . . ?
In1 O6 C11 C12 -176.5(12) . . . . ?
C13 C12 C11 O5 -164.1(19) . . . . ?
C13 C12 C11 O6 26(3) . . . . ?
C13 C12 C11 In1 8(9) . . . . ?
O7 In1 C11 O5 -157.5(11) . . . . ?
O3 In1 C11 O5 67.0(12) . . . . ?
O1 In1 C11 O5 -71.0(11) . . . . ?
O8 In1 C11 O5 -158.9(16) . . . . ?
O2 In1 C11 O5 -14.6(12) . . . . ?
O6 In1 C11 O5 -167.9(18) . . . . ?
O4 In1 C11 O5 121.3(11) . . . . ?
C1 In1 C11 O5 -44.6(12) . . . . ?
C3 In1 C11 O5 92.4(11) . . . . ?
O7 In1 C11 O6 10.4(11) . . . . ?
O3 In1 C11 O6 -125.1(10) . . . . ?
O1 In1 C11 O6 96.9(11) . . . . ?
O5 In1 C11 O6 167.9(18) . . . . ?
O8 In1 C11 O6 9(2) . . . . ?
O2 In1 C11 O6 153.3(10) . . . . ?
O4 In1 C11 O6 -70.8(11) . . . . ?
C1 In1 C11 O6 123.3(11) . . . . ?
C3 In1 C11 O6 -99.7(11) . . . . ?
O7 In1 C11 C12 30(7) . . . . ?
O3 In1 C11 C12 -106(7) . . . . ?
O1 In1 C11 C12 116(7) . . . . ?
O5 In1 C11 C12 -173(8) . . . . ?
O8 In1 C11 C12 28(8) . . . . ?
O2 In1 C11 C12 173(7) . . . . ?
O6 In1 C11 C12 19(7) . . . . ?
O4 In1 C11 C12 -51(7) . . . . ?
C1 In1 C11 C12 143(7) . . . . ?
C3 In1 C11 C12 -80(7) . . . . ?
O7 In1 O4 C3 158.5(12) . . . . ?
O3 In1 O4 C3 -0.4(11) . . . . ?
O1 In1 O4 C3 -179(2) . . . . ?
O5 In1 O4 C3 -70.4(13) . . . . ?
O8 In1 O4 C3 102.3(12) . . . . ?
O2 In1 O4 C3 17.9(16) . . . . ?
O6 In1 O4 C3 -120.5(13) . . . . ?
C1 In1 O4 C3 25(3) . . . . ?
C11 In1 O4 C3 -92.6(11) . . . . ?
C13 C14 C15 C21 -3(3) . . . . ?
In1 O4 C3 O3 1(2) . . . . ?
In1 O4 C3 C4 -179.8(12) . . . . ?
C5 C4 C3 O3 14(3) . . . . ?
C5 C4 C3 O4 -164.9(15) . . . . ?
C5 C4 C3 In1 -166(8) . . . . ?
O7 In1 C3 O3 158.3(12) . . . . ?
O1 In1 C3 O3 0(3) . . . . ?
O5 In1 C3 O3 -65.7(13) . . . . ?
O8 In1 C3 O3 103.2(13) . . . . ?
O2 In1 C3 O3 14.0(14) . . . . ?
O6 In1 C3 O3 -120.3(12) . . . . ?
O4 In1 C3 O3 -179(2) . . . . ?
C1 In1 C3 O3 10.4(16) . . . . ?
C11 In1 C3 O3 -91.2(13) . . . . ?
O7 In1 C3 O4 -22.4(13) . . . . ?
O3 In1 C3 O4 179(2) . . . . ?
O1 In1 C3 O4 179.6(17) . . . . ?
O5 In1 C3 O4 113.5(12) . . . . ?
O8 In1 C3 O4 -77.6(12) . . . . ?
O2 In1 C3 O4 -166.7(12) . . . . ?
O6 In1 C3 O4 59.0(13) . . . . ?
C1 In1 C3 O4 -170.4(12) . . . . ?
C11 In1 C3 O4 88.1(12) . . . . ?
O7 In1 C3 C4 -21(9) . . . . ?
O3 In1 C3 C4 -179(100) . . . . ?
O1 In1 C3 C4 -179(8) . . . . ?
O5 In1 C3 C4 115(9) . . . . ?
O8 In1 C3 C4 -76(9) . . . . ?
O2 In1 C3 C4 -165(8) . . . . ?
O6 In1 C3 C4 60(9) . . . . ?
O4 In1 C3 C4 1(8) . . . . ?
C1 In1 C3 C4 -169(8) . . . . ?
C11 In1 C3 C4 89(9) . . . . ?
C9 C8 C7 C6 -7(3) . . . . ?
C18 C8 C7 C6 177.5(16) 2 . . . ?
C5 C6 C7 C8 1(2) . . . . ?
O4 C3 O3 In1 -1(2) . . . . ?
C4 C3 O3 In1 179.9(18) . . . . ?
O7 In1 O3 C3 -27.9(16) . . . . ?
O1 In1 O3 C3 -179.9(12) . . . . ?
O5 In1 O3 C3 113.3(13) . . . . ?
O8 In1 O3 C3 -79.3(14) . . . . ?
O2 In1 O3 C3 -166.3(13) . . . . ?
O6 In1 O3 C3 64.7(14) . . . . ?
O4 In1 O3 C3 0.4(13) . . . . ?
C1 In1 O3 C3 -172.3(12) . . . . ?
C11 In1 O3 C3 89.7(12) . . . . ?
O7 C17 C18 C8 -41(3) . . . 2_554 ?
O8 C17 C18 C8 150.1(15) . . . 2_554 ?
C14 C15 C21 C20 3(2) . . . . ?
C14 C15 C21 C2 173.8(17) . . . 2_554 ?
C15 C21 C20 C19 -5(3) . . . . ?
C2 C21 C20 C19 -176.2(17) 2_554 . . . ?
C14 C13 C19 C20 -6(3) . . . . ?
C12 C13 C19 C20 170.8(16) . . . . ?
C21 C20 C19 C13 6(3) . . . . ?
C3S N1S C2S C1S -172.5(9) . . . . ?
C2S N1S C3S C4S -171.8(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.067