# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Shaozhong Wang'
_publ_contact_author_email       WANGSZ@NJU.EDU.CN

_publ_section_title              
;
Azaanthraquinone Assembly from N-propargylamino quinones
via Iodine-Induced 6-endo-dig Electrophilic Cyclization
;
loop_
_publ_author_name
'Shaozhong Wang'
'Na Fei'
'Huaqing Wang'
'Zhu-Jun Yao'

# Attachment '2009091903.cif'

data_x
_database_code_depnum_ccdc_archive 'CCDC 748375'
#TrackingRef '2009091903.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 I N2 O4'
_chemical_formula_weight         510.27

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'
I I -0.4742 1.8119 '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                   10.348(2)
_cell_length_b                   21.379(4)
_cell_length_c                   9.921(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.70(3)
_cell_angle_gamma                90.00
_cell_volume                     2039.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7399
_exptl_absorpt_correction_T_max  0.8561
_exptl_absorpt_process_details   ?

_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  'Nonius cad4'
_diffrn_measurement_method       \w/2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3919
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.28
_reflns_number_total             3693
_reflns_number_gt                2708
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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^)+(0.0950P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3693
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1508
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
I I 0.47824(4) 0.64398(2) 0.69655(5) 0.0546(2) Uani 1 1 d . . .
O4 O 0.0610(6) 0.85609(17) 0.8735(6) 0.0655(13) Uani 1 1 d . . .
O1 O 0.4110(5) 0.5468(2) 1.1874(4) 0.0541(11) Uani 1 1 d . . .
C1 C 0.4827(9) 0.5737(4) 1.3315(7) 0.073(2) Uani 1 1 d . . .
H1A H 0.4903 0.5428 1.4042 0.110 Uiso 1 1 calc R . .
H1B H 0.4309 0.6089 1.3445 0.110 Uiso 1 1 calc R . .
H1C H 0.5740 0.5872 1.3404 0.110 Uiso 1 1 calc R . .
O2 O 0.4378(5) 0.63620(18) 1.0838(5) 0.0537(11) Uani 1 1 d . . .
C2 C 0.3927(5) 0.5835(3) 1.0743(6) 0.0392(13) Uani 1 1 d . . .
N1 N 0.2346(5) 0.7889(2) 0.7846(5) 0.0493(12) Uani 1 1 d . . .
C3 C 0.3151(5) 0.5520(2) 0.9340(6) 0.0340(11) Uani 1 1 d . . .
O3 O 0.0490(5) 0.60748(18) 0.9291(6) 0.0666(13) Uani 1 1 d . . .
C4 C 0.3112(6) 0.4864(2) 0.9252(6) 0.0426(13) Uani 1 1 d . . .
H4A H 0.3567 0.4627 1.0079 0.051 Uiso 1 1 calc R . .
C5 C 0.2413(6) 0.4571(3) 0.7966(7) 0.0492(15) Uani 1 1 d . . .
H5A H 0.2392 0.4136 0.7925 0.059 Uiso 1 1 calc R . .
C6 C 0.1741(6) 0.4912(3) 0.6730(7) 0.0489(15) Uani 1 1 d . . .
H6A H 0.1290 0.4710 0.5851 0.059 Uiso 1 1 calc R . .
C7 C 0.1739(6) 0.5564(3) 0.6806(6) 0.0425(13) Uani 1 1 d . . .
H7A H 0.1268 0.5797 0.5978 0.051 Uiso 1 1 calc R . .
C8 C 0.2436(5) 0.5865(2) 0.8106(6) 0.0332(11) Uani 1 1 d . . .
C9 C 0.2415(6) 0.6570(2) 0.8093(5) 0.0341(11) Uani 1 1 d . . .
C10 C 0.1477(6) 0.6932(2) 0.8516(5) 0.0362(12) Uani 1 1 d . . .
C11 C 0.0503(6) 0.6638(2) 0.9115(6) 0.0391(12) Uani 1 1 d . . .
C12 C -0.0472(6) 0.7041(2) 0.9498(6) 0.0382(12) Uani 1 1 d . . .
C13 C -0.1412(6) 0.6776(3) 1.0001(7) 0.0494(15) Uani 1 1 d . . .
H13A H -0.1439 0.6343 1.0076 0.059 Uiso 1 1 calc R . .
C14 C -0.2326(7) 0.7136(3) 1.0401(7) 0.0586(17) Uani 1 1 d . . .
H14A H -0.2977 0.6951 1.0716 0.070 Uiso 1 1 calc R . .
C15 C -0.2237(8) 0.7781(3) 1.0316(8) 0.0642(19) Uani 1 1 d . . .
H15A H -0.2825 0.8030 1.0603 0.077 Uiso 1 1 calc R . .
C16 C -0.1315(7) 0.8057(3) 0.9825(7) 0.0549(16) Uani 1 1 d . . .
H16A H -0.1280 0.8491 0.9780 0.066 Uiso 1 1 calc R . .
C17 C -0.0420(6) 0.7694(2) 0.9386(6) 0.0438(13) Uani 1 1 d . . .
C18 C 0.0567(6) 0.7993(2) 0.8827(6) 0.0440(14) Uani 1 1 d . . .
C19 C 0.1504(6) 0.7584(2) 0.8382(5) 0.0381(12) Uani 1 1 d . . .
C20 C 0.3221(6) 0.7544(3) 0.7471(7) 0.0493(15) Uani 1 1 d . . .
H20A H 0.3828 0.7749 0.7124 0.059 Uiso 1 1 calc R . .
C21 C 0.3291(6) 0.6892(3) 0.7562(6) 0.0399(12) Uani 1 1 d . . .
N2 N 0.7334(8) 0.5739(3) 0.6489(8) 0.083(2) Uani 1 1 d . . .
C22 C 0.7993(8) 0.5340(4) 0.7095(8) 0.0605(17) Uani 1 1 d . . .
C23 C 0.8836(8) 0.4825(3) 0.7898(10) 0.078(2) Uani 1 1 d . . .
H23C H 0.9801 0.4920 0.8133 0.094 Uiso 1 1 calc R . .
H23B H 0.8600 0.4452 0.7317 0.094 Uiso 1 1 calc R . .
H23A H 0.8666 0.4760 0.8776 0.094 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
I 0.0618(3) 0.0570(3) 0.0553(3) 0.0013(2) 0.0339(2) -0.0023(2)
O4 0.104(4) 0.027(2) 0.072(3) 0.002(2) 0.039(3) 0.006(2)
O1 0.069(3) 0.056(3) 0.032(2) 0.0027(19) 0.0116(19) -0.007(2)
C1 0.104(6) 0.077(5) 0.027(3) 0.005(3) 0.011(3) 0.002(4)
O2 0.077(3) 0.039(2) 0.040(2) -0.0042(18) 0.016(2) -0.003(2)
C2 0.040(3) 0.040(3) 0.035(3) 0.005(2) 0.011(2) 0.010(2)
N1 0.063(3) 0.033(2) 0.054(3) 0.005(2) 0.024(3) -0.006(2)
C3 0.038(3) 0.034(3) 0.034(3) -0.001(2) 0.018(2) 0.002(2)
O3 0.087(3) 0.028(2) 0.109(4) 0.015(2) 0.064(3) 0.007(2)
C4 0.054(3) 0.032(3) 0.046(3) 0.008(3) 0.022(3) 0.009(2)
C5 0.066(4) 0.028(3) 0.059(4) -0.005(3) 0.029(3) -0.002(3)
C6 0.062(4) 0.040(3) 0.044(3) -0.009(3) 0.018(3) -0.006(3)
C7 0.054(3) 0.035(3) 0.035(3) -0.003(2) 0.011(3) -0.002(2)
C8 0.039(3) 0.026(2) 0.036(3) 0.002(2) 0.016(2) 0.001(2)
C9 0.046(3) 0.026(3) 0.030(3) 0.003(2) 0.013(2) -0.002(2)
C10 0.048(3) 0.030(3) 0.029(3) 0.002(2) 0.012(2) 0.001(2)
C11 0.043(3) 0.032(3) 0.042(3) 0.003(2) 0.014(2) 0.001(2)
C12 0.044(3) 0.035(3) 0.032(3) 0.002(2) 0.011(2) 0.007(2)
C13 0.054(4) 0.038(3) 0.058(4) 0.006(3) 0.022(3) 0.003(3)
C14 0.064(4) 0.060(4) 0.062(4) 0.002(3) 0.034(3) 0.005(3)
C15 0.080(5) 0.051(4) 0.068(5) -0.003(3) 0.035(4) 0.022(4)
C16 0.079(5) 0.038(3) 0.051(4) 0.004(3) 0.027(3) 0.015(3)
C17 0.058(4) 0.031(3) 0.036(3) 0.000(2) 0.009(3) 0.005(2)
C18 0.063(4) 0.029(3) 0.035(3) -0.003(2) 0.012(3) 0.000(3)
C19 0.051(3) 0.025(3) 0.030(3) -0.002(2) 0.005(2) 0.001(2)
C20 0.059(4) 0.043(3) 0.049(4) 0.013(3) 0.024(3) -0.008(3)
C21 0.050(3) 0.040(3) 0.031(3) -0.001(2) 0.017(2) -0.001(2)
N2 0.096(5) 0.065(4) 0.081(5) 0.018(4) 0.025(4) 0.010(4)
C22 0.068(4) 0.061(4) 0.060(4) 0.000(4) 0.033(4) -0.002(4)
C23 0.083(5) 0.057(4) 0.107(7) 0.006(5) 0.049(5) 0.005(4)

_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
I C21 2.084(6) . ?
O4 C18 1.220(6) . ?
O1 C2 1.325(7) . ?
O1 C1 1.464(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O2 C2 1.209(6) . ?
C2 C3 1.486(7) . ?
N1 C20 1.323(8) . ?
N1 C19 1.346(7) . ?
C3 C8 1.386(7) . ?
C3 C4 1.405(7) . ?
O3 C11 1.217(7) . ?
C4 C5 1.364(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.374(9) . ?
C5 H5A 0.9300 . ?
C6 C7 1.397(8) . ?
C6 H6A 0.9300 . ?
C7 C8 1.381(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.509(6) . ?
C9 C21 1.387(7) . ?
C9 C10 1.420(7) . ?
C10 C19 1.401(7) . ?
C10 C11 1.486(8) . ?
C11 C12 1.479(8) . ?
C12 C13 1.369(8) . ?
C12 C17 1.404(8) . ?
C13 C14 1.386(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.385(9) . ?
C14 H14A 0.9300 . ?
C15 C16 1.357(10) . ?
C15 H15A 0.9300 . ?
C16 C17 1.395(8) . ?
C16 H16A 0.9300 . ?
C17 C18 1.475(8) . ?
C18 C19 1.489(8) . ?
C20 C21 1.398(8) . ?
C20 H20A 0.9300 . ?
N2 C22 1.120(9) . ?
C22 C23 1.447(10) . ?
C23 H23C 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23A 0.9600 . ?

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
C2 O1 C1 117.1(5) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.8(5) . . ?
O2 C2 C3 123.7(5) . . ?
O1 C2 C3 112.5(5) . . ?
C20 N1 C19 116.8(5) . . ?
C8 C3 C4 118.8(5) . . ?
C8 C3 C2 120.9(4) . . ?
C4 C3 C2 120.3(5) . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C7 119.5(6) . . ?
C5 C6 H6A 120.3 . . ?
C7 C6 H6A 120.3 . . ?
C8 C7 C6 120.2(5) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C3 120.1(5) . . ?
C7 C8 C9 117.1(5) . . ?
C3 C8 C9 122.7(5) . . ?
C21 C9 C10 117.2(5) . . ?
C21 C9 C8 119.3(5) . . ?
C10 C9 C8 123.5(5) . . ?
C19 C10 C9 118.3(5) . . ?
C19 C10 C11 119.9(5) . . ?
C9 C10 C11 121.8(5) . . ?
O3 C11 C12 119.7(5) . . ?
O3 C11 C10 121.4(5) . . ?
C12 C11 C10 119.0(5) . . ?
C13 C12 C17 119.6(5) . . ?
C13 C12 C11 119.8(5) . . ?
C17 C12 C11 120.6(5) . . ?
C12 C13 C14 121.7(6) . . ?
C12 C13 H13A 119.1 . . ?
C14 C13 H13A 119.1 . . ?
C15 C14 C13 117.9(6) . . ?
C15 C14 H14A 121.1 . . ?
C13 C14 H14A 121.1 . . ?
C16 C15 C14 121.7(6) . . ?
C16 C15 H15A 119.1 . . ?
C14 C15 H15A 119.1 . . ?
C15 C16 C17 120.5(6) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C16 C17 C12 118.6(6) . . ?
C16 C17 C18 120.6(5) . . ?
C12 C17 C18 120.8(5) . . ?
O4 C18 C17 120.5(6) . . ?
O4 C18 C19 121.1(6) . . ?
C17 C18 C19 118.4(5) . . ?
N1 C19 C10 124.0(5) . . ?
N1 C19 C18 114.8(5) . . ?
C10 C19 C18 121.2(5) . . ?
N1 C20 C21 124.2(5) . . ?
N1 C20 H20A 117.9 . . ?
C21 C20 H20A 117.9 . . ?
C9 C21 C20 119.6(5) . . ?
C9 C21 I 122.3(4) . . ?
C20 C21 I 118.1(4) . . ?
N2 C22 C23 179.1(9) . . ?
C22 C23 H23C 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
C22 C23 H23A 109.5 . . ?
H23C C23 H23A 109.5 . . ?
H23B C23 H23A 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
C1 O1 C2 O2 4.0(9) . . . . ?
C1 O1 C2 C3 -178.2(5) . . . . ?
O2 C2 C3 C8 -25.2(8) . . . . ?
O1 C2 C3 C8 157.0(5) . . . . ?
O2 C2 C3 C4 156.0(6) . . . . ?
O1 C2 C3 C4 -21.8(7) . . . . ?
C8 C3 C4 C5 1.7(8) . . . . ?
C2 C3 C4 C5 -179.4(5) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
C4 C5 C6 C7 -2.0(9) . . . . ?
C5 C6 C7 C8 1.5(9) . . . . ?
C6 C7 C8 C3 0.6(9) . . . . ?
C6 C7 C8 C9 178.6(5) . . . . ?
C4 C3 C8 C7 -2.1(8) . . . . ?
C2 C3 C8 C7 179.0(5) . . . . ?
C4 C3 C8 C9 179.9(5) . . . . ?
C2 C3 C8 C9 1.0(8) . . . . ?
C7 C8 C9 C21 -78.2(7) . . . . ?
C3 C8 C9 C21 99.8(6) . . . . ?
C7 C8 C9 C10 97.7(6) . . . . ?
C3 C8 C9 C10 -84.3(7) . . . . ?
C21 C9 C10 C19 -0.5(7) . . . . ?
C8 C9 C10 C19 -176.6(5) . . . . ?
C21 C9 C10 C11 -179.3(5) . . . . ?
C8 C9 C10 C11 4.7(8) . . . . ?
C19 C10 C11 O3 -177.4(6) . . . . ?
C9 C10 C11 O3 1.3(8) . . . . ?
C19 C10 C11 C12 2.9(8) . . . . ?
C9 C10 C11 C12 -178.4(5) . . . . ?
O3 C11 C12 C13 -2.2(8) . . . . ?
C10 C11 C12 C13 177.6(5) . . . . ?
O3 C11 C12 C17 176.2(6) . . . . ?
C10 C11 C12 C17 -4.1(8) . . . . ?
C17 C12 C13 C14 0.3(9) . . . . ?
C11 C12 C13 C14 178.6(6) . . . . ?
C12 C13 C14 C15 -1.8(10) . . . . ?
C13 C14 C15 C16 1.6(11) . . . . ?
C14 C15 C16 C17 0.0(11) . . . . ?
C15 C16 C17 C12 -1.5(9) . . . . ?
C15 C16 C17 C18 178.9(6) . . . . ?
C13 C12 C17 C16 1.4(8) . . . . ?
C11 C12 C17 C16 -177.0(5) . . . . ?
C13 C12 C17 C18 -179.1(5) . . . . ?
C11 C12 C17 C18 2.5(8) . . . . ?
C16 C17 C18 O4 -0.4(9) . . . . ?
C12 C17 C18 O4 -179.9(6) . . . . ?
C16 C17 C18 C19 179.7(5) . . . . ?
C12 C17 C18 C19 0.2(8) . . . . ?
C20 N1 C19 C10 -2.2(8) . . . . ?
C20 N1 C19 C18 178.4(5) . . . . ?
C9 C10 C19 N1 1.6(8) . . . . ?
C11 C10 C19 N1 -179.7(5) . . . . ?
C9 C10 C19 C18 -179.0(5) . . . . ?
C11 C10 C19 C18 -0.2(8) . . . . ?
O4 C18 C19 N1 -1.8(8) . . . . ?
C17 C18 C19 N1 178.2(5) . . . . ?
O4 C18 C19 C10 178.7(6) . . . . ?
C17 C18 C19 C10 -1.3(8) . . . . ?
C19 N1 C20 C21 1.8(9) . . . . ?
C10 C9 C21 C20 0.2(8) . . . . ?
C8 C9 C21 C20 176.4(5) . . . . ?
C10 C9 C21 I 177.6(4) . . . . ?
C8 C9 C21 I -6.2(7) . . . . ?
N1 C20 C21 C9 -0.9(9) . . . . ?
N1 C20 C21 I -178.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.28
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.579
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.140