# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008



data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182

# SUBMISSION DETAILS

_publ_contact_author_name        'Prof A.J. Blake'
# For crystallographic queries
_publ_contact_author_address     
;
School of Chemistry
The University of Nottingham
University Park
Nottingham NG7 2RD
England UK
;
_publ_contact_author_email       A.J.Blake@nottingham.ac.uk
_publ_contact_author_fax         '0115 951 3563'
_publ_contact_author_phone       '0115 951 3488'

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Highly Enantioselective Synthesis of Cyclopropylcarboxamides using
Sparteine-Mediated Metallation
;
loop_
_publ_author_name
'Nigel S. Simpkins'
'David Gethin'
'Stephanie Lauru'
'Claire Wilson'

data_Compound_3a
_database_code_depnum_ccdc_archive 'CCDC 691338'
# meprco

_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H20 I N O'
_chemical_formula_sum            'C11 H20 I N O'
_chemical_formula_weight         309.18

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           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   12.6264(11)
_cell_length_b                   12.6725(11)
_cell_length_c                   15.9427(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2551.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7555
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.4

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    2.484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_T_max  0.608
_exptl_absorpt_process_details   'Bruker SADABS v2.05'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15696
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.017
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         27.43
_reflns_number_total             2893
_reflns_number_gt                2371
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2000)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  
'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)'

_refine_special_details          
;
;

_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^)+(0.066P)^2^+1.403P] 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         2893
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.102
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_restrained_S_all      1.08
_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 0.348312(17) 0.133294(17) 0.662723(14) 0.03238(12) Uani 1 1 d . . .
N N 0.30618(19) 0.3265(2) 0.83740(14) 0.0217(5) Uani 1 1 d . . .
O O 0.16737(17) 0.36219(18) 0.75267(16) 0.0320(5) Uani 1 1 d . . .
C1 C 0.3378(2) 0.3818(2) 0.6912(2) 0.0238(6) Uani 1 1 d . . .
C2 C 0.3785(3) 0.2937(2) 0.6363(2) 0.0278(6) Uani 1 1 d . . .
H2A H 0.4488 0.3078 0.6096 0.033 Uiso 1 1 calc R . .
C3 C 0.2899(3) 0.3632(3) 0.6056(2) 0.0325(7) Uani 1 1 d . . .
H3A H 0.2179 0.3324 0.6031 0.039 Uiso 1 1 calc R . .
H3B H 0.3062 0.4147 0.5608 0.039 Uiso 1 1 calc R . .
C4 C 0.2639(2) 0.3553(2) 0.76317(18) 0.0230(6) Uani 1 1 d . . .
C5' C 0.4209(2) 0.3161(2) 0.85250(19) 0.0235(6) Uani 1 1 d . . .
H5'A H 0.4573 0.3240 0.7972 0.028 Uiso 1 1 calc R . .
C5 C 0.2357(2) 0.3062(2) 0.90932(18) 0.0254(6) Uani 1 1 d . . .
H5A H 0.2827 0.2899 0.9581 0.030 Uiso 1 1 calc R . .
C7 C 0.4093(3) 0.4779(2) 0.7002(2) 0.0330(7) Uani 1 1 d . . .
H7A H 0.4525 0.4857 0.6495 0.049 Uiso 1 1 calc R . .
H7B H 0.4556 0.4686 0.7489 0.049 Uiso 1 1 calc R . .
H7C H 0.3657 0.5411 0.7079 0.049 Uiso 1 1 calc R . .
C6'1 C 0.4603(2) 0.4053(3) 0.9094(2) 0.0309(7) Uani 1 1 d . . .
H6'A H 0.4397 0.4735 0.8855 0.046 Uiso 1 1 calc R . .
H6'B H 0.5376 0.4017 0.9140 0.046 Uiso 1 1 calc R . .
H6'C H 0.4287 0.3977 0.9653 0.046 Uiso 1 1 calc R . .
C61 C 0.1717(3) 0.4039(3) 0.9339(2) 0.0350(7) Uani 1 1 d . . .
H61A H 0.2197 0.4638 0.9420 0.053 Uiso 1 1 calc R . .
H61B H 0.1332 0.3899 0.9861 0.053 Uiso 1 1 calc R . .
H61C H 0.1210 0.4205 0.8892 0.053 Uiso 1 1 calc R . .
C6'2 C 0.4508(3) 0.2082(3) 0.8876(2) 0.0316(7) Uani 1 1 d . . .
H6'D H 0.4246 0.1529 0.8501 0.047 Uiso 1 1 calc R . .
H6'E H 0.4191 0.1994 0.9433 0.047 Uiso 1 1 calc R . .
H6'F H 0.5281 0.2030 0.8921 0.047 Uiso 1 1 calc R . .
C62 C 0.1673(3) 0.2085(3) 0.8951(2) 0.0345(7) Uani 1 1 d . . .
H62A H 0.2126 0.1488 0.8794 0.052 Uiso 1 1 calc R . .
H62B H 0.1165 0.2223 0.8500 0.052 Uiso 1 1 calc R . .
H62C H 0.1289 0.1914 0.9468 0.052 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 0.03469(17) 0.02559(16) 0.03684(17) -0.00573(8) 0.00278(8) -0.00086(8)
N 0.0153(11) 0.0226(12) 0.0271(13) 0.0017(10) 0.0003(9) 0.0015(10)
O 0.0189(10) 0.0442(15) 0.0330(13) 0.0007(10) -0.0031(9) 0.0073(9)
C1 0.0234(14) 0.0213(14) 0.0267(15) 0.0020(12) 0.0015(12) 0.0030(10)
C2 0.0270(15) 0.0283(16) 0.0281(15) 0.0029(13) 0.0043(12) 0.0030(13)
C3 0.0319(17) 0.0384(18) 0.0273(16) 0.0053(13) -0.0018(13) 0.0079(13)
C4 0.0220(14) 0.0217(13) 0.0252(15) -0.0012(10) 0.0005(11) 0.0026(11)
C5' 0.0161(13) 0.0260(15) 0.0284(15) 0.0017(12) -0.0023(11) 0.0011(11)
C5 0.0208(14) 0.0289(15) 0.0264(15) 0.0009(12) 0.0035(11) -0.0010(12)
C7 0.0313(17) 0.0241(15) 0.044(2) 0.0062(14) 0.0017(14) -0.0017(12)
C6'1 0.0226(15) 0.0330(16) 0.0370(17) -0.0031(13) -0.0048(13) -0.0023(13)
C61 0.0276(16) 0.0384(18) 0.0390(19) -0.0082(15) 0.0082(14) -0.0003(14)
C6'2 0.0286(16) 0.0286(15) 0.0375(17) 0.0047(13) -0.0047(13) 0.0091(13)
C62 0.0288(16) 0.0311(17) 0.0436(19) 0.0014(15) 0.0057(14) -0.0069(13)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I C2 2.111(3) . ?
N C4 1.348(4) . ?
N C5' 1.474(4) . ?
N C5 1.474(3) . ?
O C4 1.233(4) . ?
C1 C2 1.509(4) . ?
C1 C3 1.510(5) . ?
C1 C4 1.517(4) . ?
C1 C7 1.523(4) . ?
C2 C3 1.505(4) . ?
C5' C6'2 1.525(4) . ?
C5' C6'1 1.532(4) . ?
C5 C62 1.527(4) . ?
C5 C61 1.529(4) . ?

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
C4 N C5' 123.8(2) . . ?
C4 N C5 119.4(2) . . ?
C5' N C5 116.8(2) . . ?
C2 C1 C3 59.8(2) . . ?
C2 C1 C4 119.0(2) . . ?
C3 C1 C4 113.7(3) . . ?
C2 C1 C7 116.4(3) . . ?
C3 C1 C7 116.6(3) . . ?
C4 C1 C7 118.1(3) . . ?
C3 C2 C1 60.1(2) . . ?
C3 C2 I 119.6(2) . . ?
C1 C2 I 122.3(2) . . ?
C2 C3 C1 60.0(2) . . ?
O C4 N 122.0(3) . . ?
O C4 C1 119.3(3) . . ?
N C4 C1 118.7(3) . . ?
N C5' C6'2 112.6(2) . . ?
N C5' C6'1 110.5(2) . . ?
C6'2 C5' C6'1 111.3(3) . . ?
N C5 C62 111.6(3) . . ?
N C5 C61 112.1(3) . . ?
C62 C5 C61 113.3(3) . . ?

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
C4 C1 C2 C3 102.1(3) . . . . ?
C7 C1 C2 C3 -106.8(3) . . . . ?
C3 C1 C2 I -108.1(3) . . . . ?
C4 C1 C2 I -6.0(4) . . . . ?
C7 C1 C2 I 145.1(2) . . . . ?
I C2 C3 C1 112.6(3) . . . . ?
C4 C1 C3 C2 -110.9(3) . . . . ?
C7 C1 C3 C2 106.5(3) . . . . ?
C5' N C4 O 179.3(3) . . . . ?
C5 N C4 O -2.2(4) . . . . ?
C5' N C4 C1 -1.8(4) . . . . ?
C5 N C4 C1 176.6(2) . . . . ?
C2 C1 C4 O -95.5(3) . . . . ?
C3 C1 C4 O -28.1(4) . . . . ?
C7 C1 C4 O 113.9(3) . . . . ?
C2 C1 C4 N 85.6(4) . . . . ?
C3 C1 C4 N 153.0(3) . . . . ?
C7 C1 C4 N -65.0(4) . . . . ?
C4 N C5' C6'2 -125.8(3) . . . . ?
C5 N C5' C6'2 55.7(3) . . . . ?
C4 N C5' C6'1 109.1(3) . . . . ?
C5 N C5' C6'1 -69.4(3) . . . . ?
C4 N C5 C62 67.1(3) . . . . ?
C5' N C5 C62 -114.3(3) . . . . ?
C4 N C5 C61 -61.2(3) . . . . ?
C5' N C5 C61 117.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.991

_refine_diff_density_max         2.14
_refine_diff_density_min         -1.08
_refine_diff_density_rms         0.14

#===END of CIF

data_Compound_3i
_database_code_depnum_ccdc_archive 'CCDC 691339'
#iprnop

_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 I N O'
_chemical_formula_sum            'C16 H22 I N O'
_chemical_formula_weight         371.25

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   'P 21/n'

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

_cell_length_a                   8.7467(5)
_cell_length_b                   12.9523(7)
_cell_length_c                   14.2629(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.149(1)
_cell_angle_gamma                90.00
_cell_volume                     1615.52(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6827
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.349
_exptl_absorpt_correction_T_max  0.472
_exptl_absorpt_process_details   'Bruker SADABS v2.05'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10020
_diffrn_reflns_av_R_equivalents  0.013
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.59
_reflns_number_total             3683
_reflns_number_gt                3527
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer (CCDC, 2003); PLATON (Spek, 2003)'

_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^)+(0.0389P)^2^+0.9794P] 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         3683
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_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
I1 I 0.217662(15) 0.986851(11) 0.972286(9) 0.02746(6) Uani 1 1 d . . .
O1 O 0.17230(17) 0.71841(11) 0.82873(10) 0.0288(3) Uani 1 1 d . . .
N1 N 0.08987(18) 0.85549(13) 0.74241(11) 0.0217(3) Uani 1 1 d . . .
C1 C 0.3551(2) 0.85233(15) 0.80610(13) 0.0196(4) Uani 1 1 d . . .
C2 C 0.3902(2) 0.92680(16) 0.88535(13) 0.0225(4) Uani 1 1 d . . .
H2A H 0.4744 0.9766 0.8721 0.027 Uiso 1 1 calc R . .
C3 C 0.4412(2) 0.81719(17) 0.89431(14) 0.0255(4) Uani 1 1 d . . .
H3A H 0.3864 0.7723 0.9387 0.031 Uiso 1 1 calc R . .
H3B H 0.5519 0.8026 0.8893 0.031 Uiso 1 1 calc R . .
C4 C 0.1957(2) 0.80425(15) 0.79495(13) 0.0197(4) Uani 1 1 d . . .
C5 C 0.1111(2) 0.96113(16) 0.70556(16) 0.0280(4) Uani 1 1 d . . .
H5A H 0.2078 0.9892 0.7342 0.034 Uiso 1 1 calc R . .
C6 C -0.0194(3) 1.03208(18) 0.7344(2) 0.0395(6) Uani 1 1 d . . .
H6A H -0.0284 1.0309 0.8028 0.059 Uiso 1 1 calc R . .
H6B H -0.1154 1.0082 0.7052 0.059 Uiso 1 1 calc R . .
H6C H 0.0018 1.1027 0.7138 0.059 Uiso 1 1 calc R . .
C7 C 0.1288(3) 0.9615(2) 0.59960(18) 0.0404(6) Uani 1 1 d . . .
H7A H 0.2127 0.9153 0.5827 0.061 Uiso 1 1 calc R . .
H7B H 0.1515 1.0317 0.5785 0.061 Uiso 1 1 calc R . .
H7C H 0.0336 0.9376 0.5694 0.061 Uiso 1 1 calc R . .
C8 C -0.0530(2) 0.80116(17) 0.71403(15) 0.0276(4) Uani 1 1 d . . .
H8A H -0.1129 0.8501 0.6734 0.033 Uiso 1 1 calc R . .
C9 C -0.0190(3) 0.70697(18) 0.65364(17) 0.0369(5) Uani 1 1 d . . .
H9A H 0.0449 0.7276 0.6012 0.055 Uiso 1 1 calc R . .
H9B H -0.1152 0.6778 0.6292 0.055 Uiso 1 1 calc R . .
H9C H 0.0351 0.6550 0.6917 0.055 Uiso 1 1 calc R . .
C10 C -0.1531(3) 0.7752(2) 0.79664(19) 0.0417(6) Uani 1 1 d . . .
H10A H -0.1719 0.8379 0.8331 0.063 Uiso 1 1 calc R . .
H10B H -0.1013 0.7239 0.8366 0.063 Uiso 1 1 calc R . .
H10C H -0.2508 0.7470 0.7735 0.063 Uiso 1 1 calc R . .
C11 C 0.4396(2) 0.85960(15) 0.71528(13) 0.0213(4) Uani 1 1 d . . .
C12 C 0.4311(2) 0.77567(16) 0.65362(15) 0.0269(4) Uani 1 1 d . . .
H12A H 0.3739 0.7162 0.6701 0.032 Uiso 1 1 calc R . .
C13 C 0.5052(3) 0.77843(18) 0.56871(16) 0.0322(5) Uani 1 1 d . . .
H13A H 0.4988 0.7207 0.5277 0.039 Uiso 1 1 calc R . .
C14 C 0.5887(3) 0.86458(19) 0.54298(15) 0.0324(5) Uani 1 1 d . . .
H14A H 0.6395 0.8662 0.4847 0.039 Uiso 1 1 calc R . .
C15 C 0.5970(2) 0.94830(19) 0.60354(15) 0.0306(4) Uani 1 1 d . . .
H15A H 0.6533 1.0079 0.5864 0.037 Uiso 1 1 calc R . .
C16 C 0.5236(2) 0.94583(17) 0.68904(14) 0.0259(4) Uani 1 1 d . . .
H16A H 0.5309 1.0035 0.7300 0.031 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
I1 0.02740(9) 0.03332(10) 0.02177(9) -0.00407(5) 0.00325(6) 0.00184(5)
O1 0.0317(8) 0.0262(7) 0.0283(8) 0.0097(6) -0.0011(6) -0.0047(6)
N1 0.0212(8) 0.0212(8) 0.0224(8) 0.0007(6) -0.0050(6) -0.0016(6)
C1 0.0199(8) 0.0226(9) 0.0163(9) 0.0020(7) -0.0007(7) 0.0017(7)
C2 0.0203(9) 0.0293(10) 0.0180(9) -0.0009(7) 0.0003(7) -0.0008(7)
C3 0.0232(9) 0.0342(11) 0.0190(10) 0.0038(8) -0.0035(7) 0.0044(8)
C4 0.0222(9) 0.0232(9) 0.0138(8) -0.0008(7) 0.0005(7) 0.0000(7)
C5 0.0271(10) 0.0220(9) 0.0345(12) 0.0055(8) -0.0107(9) -0.0018(8)
C6 0.0338(12) 0.0269(11) 0.0570(17) -0.0053(11) -0.0169(11) 0.0064(9)
C7 0.0433(13) 0.0440(14) 0.0335(13) 0.0177(11) -0.0101(10) -0.0032(11)
C8 0.0236(10) 0.0289(10) 0.0299(11) -0.0023(8) -0.0071(8) -0.0055(8)
C9 0.0445(13) 0.0328(12) 0.0331(13) -0.0087(9) -0.0082(10) -0.0076(10)
C10 0.0253(11) 0.0528(15) 0.0471(15) -0.0053(12) 0.0047(10) -0.0104(10)
C11 0.0205(9) 0.0251(9) 0.0184(9) 0.0017(7) -0.0010(7) 0.0043(7)
C12 0.0322(11) 0.0239(10) 0.0246(10) 0.0002(8) 0.0005(8) 0.0044(8)
C13 0.0388(12) 0.0327(11) 0.0250(11) -0.0048(9) 0.0030(9) 0.0074(9)
C14 0.0311(11) 0.0451(13) 0.0212(10) 0.0021(9) 0.0063(8) 0.0060(9)
C15 0.0294(10) 0.0375(12) 0.0249(11) 0.0043(9) 0.0033(8) -0.0029(9)
C16 0.0275(10) 0.0295(10) 0.0208(10) -0.0013(8) 0.0009(8) -0.0018(8)

_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
I1 C2 2.1202(19) . ?
O1 C4 1.230(2) . ?
N1 C4 1.353(2) . ?
N1 C5 1.479(3) . ?
N1 C8 1.483(2) . ?
C1 C11 1.507(3) . ?
C1 C2 1.513(3) . ?
C1 C3 1.523(3) . ?
C1 C4 1.532(3) . ?
C2 C3 1.493(3) . ?
C5 C7 1.522(3) . ?
C5 C6 1.528(3) . ?
C8 C10 1.520(3) . ?
C8 C9 1.526(3) . ?
C11 C16 1.393(3) . ?
C11 C12 1.399(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.390(3) . ?

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
C4 N1 C5 124.16(16) . . ?
C4 N1 C8 118.79(17) . . ?
C5 N1 C8 116.93(15) . . ?
C11 C1 C2 120.43(16) . . ?
C11 C1 C3 119.06(16) . . ?
C2 C1 C3 58.91(13) . . ?
C11 C1 C4 113.39(15) . . ?
C2 C1 C4 120.50(16) . . ?
C3 C1 C4 113.48(16) . . ?
C3 C2 C1 60.89(13) . . ?
C3 C2 I1 120.92(14) . . ?
C1 C2 I1 122.31(13) . . ?
C2 C3 C1 60.20(12) . . ?
O1 C4 N1 122.90(18) . . ?
O1 C4 C1 118.97(17) . . ?
N1 C4 C1 117.97(16) . . ?
N1 C5 C7 111.81(19) . . ?
N1 C5 C6 111.16(19) . . ?
C7 C5 C6 110.92(19) . . ?
N1 C8 C10 112.88(17) . . ?
N1 C8 C9 111.13(18) . . ?
C10 C8 C9 112.5(2) . . ?
C16 C11 C12 118.41(18) . . ?
C16 C11 C1 123.49(18) . . ?
C12 C11 C1 118.09(18) . . ?
C13 C12 C11 120.6(2) . . ?
C12 C13 C14 120.7(2) . . ?
C13 C14 C15 119.0(2) . . ?
C14 C15 C16 120.6(2) . . ?
C15 C16 C11 120.7(2) . . ?

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
C11 C1 C2 C3 -107.67(19) . . . . ?
C4 C1 C2 C3 100.65(19) . . . . ?
C11 C1 C2 I1 142.23(14) . . . . ?
C3 C1 C2 I1 -110.10(17) . . . . ?
C4 C1 C2 I1 -9.5(2) . . . . ?
I1 C2 C3 C1 112.31(16) . . . . ?
C11 C1 C3 C2 109.98(19) . . . . ?
C4 C1 C3 C2 -112.60(18) . . . . ?
C5 N1 C4 O1 176.23(19) . . . . ?
C8 N1 C4 O1 -7.9(3) . . . . ?
C5 N1 C4 C1 -8.5(3) . . . . ?
C8 N1 C4 C1 167.29(17) . . . . ?
C11 C1 C4 O1 111.1(2) . . . . ?
C2 C1 C4 O1 -95.4(2) . . . . ?
C3 C1 C4 O1 -28.8(3) . . . . ?
C11 C1 C4 N1 -64.3(2) . . . . ?
C2 C1 C4 N1 89.2(2) . . . . ?
C3 C1 C4 N1 155.79(17) . . . . ?
C4 N1 C5 C7 109.8(2) . . . . ?
C8 N1 C5 C7 -66.1(2) . . . . ?
C4 N1 C5 C6 -125.6(2) . . . . ?
C8 N1 C5 C6 58.5(2) . . . . ?
C4 N1 C8 C10 66.1(2) . . . . ?
C5 N1 C8 C10 -117.7(2) . . . . ?
C4 N1 C8 C9 -61.4(2) . . . . ?
C5 N1 C8 C9 114.8(2) . . . . ?
C2 C1 C11 C16 -16.2(3) . . . . ?
C3 C1 C11 C16 -85.2(2) . . . . ?
C4 C1 C11 C16 137.38(19) . . . . ?
C2 C1 C11 C12 164.74(17) . . . . ?
C3 C1 C11 C12 95.8(2) . . . . ?
C4 C1 C11 C12 -41.7(2) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C1 C11 C12 C13 179.38(18) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
C1 C11 C16 C15 -178.95(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986

_refine_diff_density_max         0.74
_refine_diff_density_min         -0.43
_refine_diff_density_rms         0.06

#===END of CIF


# Attachment 'ICPRNO_CIF.txt'

data_icprno
_database_code_depnum_ccdc_archive 'CCDC 695941'

_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 I N O'
_chemical_formula_sum            'C16 H22 I N O'
_chemical_formula_weight         371.25

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   'P 21'

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

_cell_length_a                   8.5952(4)
_cell_length_b                   23.5395(10)
_cell_length_c                   8.7614(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.232(1)
_cell_angle_gamma                90.00
_cell_volume                     1652.34(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12853
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.473
_exptl_absorpt_correction_T_max  0.594
_exptl_absorpt_process_details   'Bruker SADABS v2.05'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14190
_diffrn_reflns_av_R_equivalents  0.011
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         27.62
_reflns_number_total             7310
_reflns_number_gt                7265
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2000)'
_computing_data_reduction        
'Bruker SAINT; Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  
'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)'

_refine_special_details          
;
There is a short intermolecular I1...O1A contact of 2.962(2) Angstroms,
well within the sum of the van der Waals radii for the participating
atoms (3.55 Angstroms). The C2-I1...O1A angle of 170.12(7) degrees is
typical for such an interaction, the mean value from a search of the
Cambridge Structural Database being 166(8) degrees. The I1...O1A-C4A
angle of 172.7(2) degrees is less diagnostically useful, because of the
very wide variation observed for this parameter, but it is not
inconsistent with values in the CSD.
;

_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^)+(0.030P)^2^+0.321P] 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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.022(10)
_refine_ls_number_reflns         7310
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0175
_refine_ls_R_factor_gt           0.0174
_refine_ls_wR_factor_ref         0.0459
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.002
_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
I1 I 0.090266(16) 0.304329(5) 0.196716(16) 0.02985(4) Uani 1 1 d . . .
O1 O 0.3821(2) 0.44501(8) 0.30198(19) 0.0331(4) Uani 1 1 d . . .
N1 N 0.4806(2) 0.37279(7) 0.1918(2) 0.0239(3) Uani 1 1 d . . .
C1 C 0.1993(3) 0.41220(8) 0.0408(3) 0.0223(4) Uani 1 1 d . . .
C2 C 0.0574(3) 0.37162(10) 0.0277(3) 0.0295(4) Uani 1 1 d . . .
H2A H -0.0171 0.3625 -0.0869 0.035 Uiso 1 1 calc R . .
C3 C 0.0494(3) 0.43248(10) 0.0775(3) 0.0334(5) Uani 1 1 d . . .
H3A H 0.0650 0.4401 0.1932 0.040 Uiso 1 1 calc R . .
H3B H -0.0305 0.4581 -0.0030 0.040 Uiso 1 1 calc R . .
C4 C 0.3611(3) 0.41052(9) 0.1900(2) 0.0225(4) Uani 1 1 d . . .
C5 C 0.6479(3) 0.37627(12) 0.3241(3) 0.0376(5) Uani 1 1 d . . .
H5A H 0.7183 0.3464 0.2997 0.045 Uiso 1 1 calc R . .
C6 C 0.6419(4) 0.36193(16) 0.4907(3) 0.0553(8) Uani 1 1 d . . .
H6A H 0.5867 0.3251 0.4851 0.083 Uiso 1 1 calc R . .
H6B H 0.5793 0.3914 0.5229 0.083 Uiso 1 1 calc R . .
H6C H 0.7558 0.3600 0.5716 0.083 Uiso 1 1 calc R . .
C7 C 0.7315(4) 0.43304(14) 0.3194(4) 0.0504(7) Uani 1 1 d . . .
H7A H 0.7327 0.4394 0.2093 0.076 Uiso 1 1 calc R . .
H7B H 0.8463 0.4325 0.3988 0.076 Uiso 1 1 calc R . .
H7C H 0.6692 0.4637 0.3472 0.076 Uiso 1 1 calc R . .
C8 C 0.4593(3) 0.33084(9) 0.0599(3) 0.0280(4) Uani 1 1 d . . .
H8A H 0.3386 0.3308 -0.0121 0.034 Uiso 1 1 calc R . .
C9 C 0.5599(3) 0.34818(11) -0.0472(3) 0.0381(5) Uani 1 1 d . . .
H9A H 0.5293 0.3869 -0.0881 0.057 Uiso 1 1 calc R . .
H9B H 0.5348 0.3220 -0.1399 0.057 Uiso 1 1 calc R . .
H9C H 0.6795 0.3467 0.0185 0.057 Uiso 1 1 calc R . .
C10 C 0.5037(3) 0.27073(10) 0.1271(3) 0.0404(6) Uani 1 1 d . . .
H10A H 0.4382 0.2609 0.1945 0.061 Uiso 1 1 calc R . .
H10B H 0.6229 0.2689 0.1941 0.061 Uiso 1 1 calc R . .
H10C H 0.4785 0.2438 0.0360 0.061 Uiso 1 1 calc R . .
C11 C 0.2230(3) 0.43309(8) -0.1118(2) 0.0215(4) Uani 1 1 d . . .
C12 C 0.3145(3) 0.48314(9) -0.1011(3) 0.0271(4) Uani 1 1 d . . .
H12A H 0.3559 0.5033 -0.0004 0.033 Uiso 1 1 calc R . .
C13 C 0.3454(3) 0.50376(11) -0.2366(3) 0.0348(5) Uani 1 1 d . . .
H13A H 0.4051 0.5383 -0.2287 0.042 Uiso 1 1 calc R . .
C14 C 0.2888(3) 0.47388(12) -0.3832(3) 0.0352(5) Uani 1 1 d . . .
H14A H 0.3116 0.4875 -0.4750 0.042 Uiso 1 1 calc R . .
C15 C 0.1994(3) 0.42426(11) -0.3948(3) 0.0326(5) Uani 1 1 d . . .
H15A H 0.1611 0.4036 -0.4947 0.039 Uiso 1 1 calc R . .
C16 C 0.1649(3) 0.40428(10) -0.2602(3) 0.0267(4) Uani 1 1 d . . .
H16A H 0.1010 0.3706 -0.2703 0.032 Uiso 1 1 calc R . .
I1A I 0.868791(17) 0.541314(6) 0.706325(16) 0.03311(4) Uani 1 1 d . . .
O1A O 0.8207(2) 0.70280(7) 0.5895(2) 0.0339(4) Uani 1 1 d . . .
N1A N 0.8384(2) 0.65086(7) 0.3797(2) 0.0209(3) Uani 1 1 d . . .
C1A C 0.6115(2) 0.63173(8) 0.4830(2) 0.0196(3) Uani 1 1 d . . .
C2A C 0.6311(3) 0.57759(9) 0.5812(3) 0.0264(4) Uani 1 1 d . . .
H2AA H 0.5385 0.5495 0.5354 0.032 Uiso 1 1 calc R . .
C3A C 0.5832(3) 0.63121(10) 0.6449(3) 0.0294(4) Uani 1 1 d . . .
H3AA H 0.6682 0.6496 0.7405 0.035 Uiso 1 1 calc R . .
H3AB H 0.4670 0.6346 0.6409 0.035 Uiso 1 1 calc R . .
C4A C 0.7681(2) 0.66414(8) 0.4895(2) 0.0211(4) Uani 1 1 d . . .
C5A C 0.9793(3) 0.68610(9) 0.3721(3) 0.0285(4) Uani 1 1 d . . .
H5AA H 1.0126 0.6696 0.2832 0.034 Uiso 1 1 calc R . .
C6A C 0.9258(3) 0.74716(11) 0.3225(4) 0.0412(6) Uani 1 1 d . . .
H6AA H 0.8275 0.7473 0.2210 0.062 Uiso 1 1 calc R . .
H6AB H 1.0172 0.7677 0.3049 0.062 Uiso 1 1 calc R . .
H6AC H 0.8984 0.7658 0.4095 0.062 Uiso 1 1 calc R . .
C7A C 1.1324(3) 0.68264(13) 0.5290(4) 0.0444(6) Uani 1 1 d . . .
H7AA H 1.1626 0.6427 0.5554 0.067 Uiso 1 1 calc R . .
H7AB H 1.1073 0.7003 0.6188 0.067 Uiso 1 1 calc R . .
H7AC H 1.2256 0.7027 0.5138 0.067 Uiso 1 1 calc R . .
C8A C 0.7878(3) 0.60145(8) 0.2675(2) 0.0238(4) Uani 1 1 d . . .
H8AA H 0.7021 0.5797 0.2961 0.029 Uiso 1 1 calc R . .
C9A C 0.7063(3) 0.62071(12) 0.0890(3) 0.0367(5) Uani 1 1 d . . .
H9AA H 0.6131 0.6463 0.0786 0.055 Uiso 1 1 calc R . .
H9AB H 0.6646 0.5875 0.0187 0.055 Uiso 1 1 calc R . .
H9AC H 0.7889 0.6406 0.0556 0.055 Uiso 1 1 calc R . .
C10A C 0.9342(3) 0.56140(10) 0.2893(3) 0.0363(5) Uani 1 1 d . . .
H10D H 0.9846 0.5501 0.4045 0.055 Uiso 1 1 calc R . .
H10E H 1.0178 0.5809 0.2563 0.055 Uiso 1 1 calc R . .
H10F H 0.8942 0.5276 0.2211 0.055 Uiso 1 1 calc R . .
C11A C 0.4622(2) 0.64036(9) 0.3293(2) 0.0211(4) Uani 1 1 d . . .
C12A C 0.4150(3) 0.69614(10) 0.2765(3) 0.0279(4) Uani 1 1 d . . .
H12B H 0.4784 0.7271 0.3376 0.034 Uiso 1 1 calc R . .
C13A C 0.2771(3) 0.70670(10) 0.1363(3) 0.0327(5) Uani 1 1 d . . .
H13B H 0.2463 0.7448 0.1028 0.039 Uiso 1 1 calc R . .
C14A C 0.1834(3) 0.66200(11) 0.0443(3) 0.0314(5) Uani 1 1 d . . .
H14B H 0.0896 0.6691 -0.0526 0.038 Uiso 1 1 calc R . .
C15A C 0.2295(3) 0.60672(10) 0.0967(3) 0.0302(4) Uani 1 1 d . . .
H15B H 0.1663 0.5759 0.0348 0.036 Uiso 1 1 calc R . .
C16A C 0.3670(3) 0.59568(9) 0.2388(3) 0.0258(4) Uani 1 1 d . . .
H16B H 0.3956 0.5576 0.2737 0.031 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
I1 0.02816(6) 0.02991(7) 0.02815(7) 0.00997(5) 0.00620(5) -0.00513(5)
O1 0.0471(10) 0.0304(9) 0.0227(8) -0.0050(6) 0.0138(7) 0.0034(7)
N1 0.0224(8) 0.0218(8) 0.0231(8) -0.0038(6) 0.0030(7) 0.0006(6)
C1 0.0253(9) 0.0186(9) 0.0253(10) 0.0047(7) 0.0120(8) 0.0043(7)
C2 0.0236(10) 0.0353(11) 0.0274(10) 0.0123(8) 0.0068(8) 0.0013(8)
C3 0.0323(11) 0.0367(13) 0.0372(12) 0.0175(10) 0.0199(10) 0.0148(9)
C4 0.0299(10) 0.0184(9) 0.0210(9) 0.0022(7) 0.0116(8) -0.0002(7)
C5 0.0245(10) 0.0419(13) 0.0354(12) -0.0044(10) -0.0024(9) 0.0009(9)
C6 0.0509(17) 0.067(2) 0.0311(13) 0.0075(12) -0.0059(12) 0.0071(15)
C7 0.0364(14) 0.0535(17) 0.0509(16) -0.0138(13) 0.0033(12) -0.0173(12)
C8 0.0271(10) 0.0235(10) 0.0282(10) -0.0067(8) 0.0039(8) 0.0060(8)
C9 0.0372(12) 0.0406(13) 0.0368(12) -0.0046(10) 0.0138(10) 0.0127(10)
C10 0.0391(13) 0.0237(11) 0.0510(14) -0.0019(10) 0.0072(11) 0.0098(9)
C11 0.0226(9) 0.0210(9) 0.0219(9) 0.0031(7) 0.0092(7) 0.0044(7)
C12 0.0382(11) 0.0236(10) 0.0227(10) -0.0013(7) 0.0149(9) -0.0028(8)
C13 0.0449(13) 0.0346(12) 0.0296(11) 0.0024(9) 0.0191(10) -0.0094(10)
C14 0.0379(12) 0.0461(14) 0.0257(11) 0.0034(9) 0.0163(9) -0.0019(10)
C15 0.0357(12) 0.0404(13) 0.0202(10) -0.0034(8) 0.0084(9) 0.0025(10)
C16 0.0272(10) 0.0255(10) 0.0250(10) 0.0001(8) 0.0064(8) 0.0012(8)
I1A 0.03118(7) 0.03669(8) 0.02470(6) 0.00731(5) 0.00202(5) 0.00955(6)
O1A 0.0343(8) 0.0328(8) 0.0362(9) -0.0167(7) 0.0145(7) -0.0088(7)
N1A 0.0219(8) 0.0181(8) 0.0229(8) -0.0013(6) 0.0083(7) -0.0013(6)
C1A 0.0187(8) 0.0222(9) 0.0180(8) 0.0013(7) 0.0068(7) 0.0011(7)
C2A 0.0232(9) 0.0305(11) 0.0244(9) 0.0075(8) 0.0073(8) 0.0009(8)
C3A 0.0288(10) 0.0405(12) 0.0217(10) 0.0052(8) 0.0126(8) 0.0064(9)
C4A 0.0194(8) 0.0195(9) 0.0223(8) -0.0001(7) 0.0050(7) 0.0008(7)
C5A 0.0244(10) 0.0265(11) 0.0371(12) 0.0005(9) 0.0144(9) -0.0043(8)
C6A 0.0412(13) 0.0290(12) 0.0559(16) 0.0079(10) 0.0205(12) -0.0055(10)
C7A 0.0204(11) 0.0556(17) 0.0524(16) 0.0029(13) 0.0075(11) -0.0059(10)
C8A 0.0296(10) 0.0205(9) 0.0245(9) -0.0048(7) 0.0139(8) -0.0026(8)
C9A 0.0446(13) 0.0432(13) 0.0223(11) -0.0046(9) 0.0120(10) -0.0054(11)
C10A 0.0422(12) 0.0277(11) 0.0491(14) -0.0029(9) 0.0285(11) 0.0050(9)
C11A 0.0173(8) 0.0251(10) 0.0226(9) 0.0041(7) 0.0090(8) 0.0021(7)
C12A 0.0244(10) 0.0261(11) 0.0324(11) 0.0044(8) 0.0094(9) 0.0002(8)
C13A 0.0260(10) 0.0323(12) 0.0380(12) 0.0144(9) 0.0094(9) 0.0039(9)
C14A 0.0215(10) 0.0451(13) 0.0244(10) 0.0096(10) 0.0044(9) 0.0029(9)
C15A 0.0235(10) 0.0364(12) 0.0269(11) -0.0036(8) 0.0045(8) -0.0004(9)
C16A 0.0237(9) 0.0250(10) 0.0266(10) 0.0004(8) 0.0064(8) 0.0008(7)

_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
I1 C2 2.116(2) . ?
O1 C4 1.236(2) . ?
N1 C4 1.353(3) . ?
N1 C8 1.480(3) . ?
N1 C5 1.487(3) . ?
C1 C11 1.506(3) . ?
C1 C3 1.514(3) . ?
C1 C2 1.521(3) . ?
C1 C4 1.526(3) . ?
C2 C3 1.506(3) . ?
C5 C6 1.517(4) . ?
C5 C7 1.525(4) . ?
C8 C10 1.527(3) . ?
C8 C9 1.543(3) . ?
C11 C16 1.389(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.382(4) . ?
C15 C16 1.398(3) . ?
I1A C2A 2.117(2) . ?
O1A C4A 1.230(3) . ?
N1A C4A 1.345(3) . ?
N1A C8A 1.483(2) . ?
N1A C5A 1.490(3) . ?
C1A C11A 1.500(3) . ?
C1A C2A 1.512(3) . ?
C1A C3A 1.524(3) . ?
C1A C4A 1.530(3) . ?
C2A C3A 1.497(3) . ?
C5A C7A 1.522(4) . ?
C5A C6A 1.524(3) . ?
C8A C10A 1.528(3) . ?
C8A C9A 1.532(3) . ?
C11A C16A 1.391(3) . ?
C11A C12A 1.402(3) . ?
C12A C13A 1.386(3) . ?
C13A C14A 1.391(4) . ?
C14A C15A 1.389(3) . ?
C15A C16A 1.396(3) . ?

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
C4 N1 C8 123.38(17) . . ?
C4 N1 C5 119.23(18) . . ?
C8 N1 C5 117.16(18) . . ?
C11 C1 C3 119.00(17) . . ?
C11 C1 C2 120.07(18) . . ?
C3 C1 C2 59.52(15) . . ?
C11 C1 C4 113.25(17) . . ?
C3 C1 C4 114.09(18) . . ?
C2 C1 C4 120.37(17) . . ?
C3 C2 C1 60.00(14) . . ?
C3 C2 I1 121.20(16) . . ?
C1 C2 I1 121.17(14) . . ?
C2 C3 C1 60.47(14) . . ?
O1 C4 N1 122.01(19) . . ?
O1 C4 C1 119.28(18) . . ?
N1 C4 C1 118.64(17) . . ?
N1 C5 C6 112.2(2) . . ?
N1 C5 C7 111.1(2) . . ?
C6 C5 C7 113.7(2) . . ?
N1 C8 C10 111.95(19) . . ?
N1 C8 C9 111.11(19) . . ?
C10 C8 C9 111.29(19) . . ?
C16 C11 C12 118.46(18) . . ?
C16 C11 C1 123.58(19) . . ?
C12 C11 C1 117.91(18) . . ?
C13 C12 C11 120.7(2) . . ?
C14 C13 C12 120.0(2) . . ?
C15 C14 C13 119.7(2) . . ?
C14 C15 C16 120.3(2) . . ?
C11 C16 C15 120.7(2) . . ?
C4A N1A C8A 123.82(16) . . ?
C4A N1A C5A 119.09(17) . . ?
C8A N1A C5A 117.05(16) . . ?
C11A C1A C2A 120.50(17) . . ?
C11A C1A C3A 117.60(16) . . ?
C2A C1A C3A 59.08(14) . . ?
C11A C1A C4A 114.90(16) . . ?
C2A C1A C4A 118.93(16) . . ?
C3A C1A C4A 113.86(17) . . ?
C3A C2A C1A 60.83(13) . . ?
C3A C2A I1A 119.43(15) . . ?
C1A C2A I1A 121.48(13) . . ?
C2A C3A C1A 60.09(13) . . ?
O1A C4A N1A 122.46(19) . . ?
O1A C4A C1A 119.13(18) . . ?
N1A C4A C1A 118.33(17) . . ?
N1A C5A C7A 112.35(19) . . ?
N1A C5A C6A 111.83(18) . . ?
C7A C5A C6A 112.4(2) . . ?
N1A C8A C10A 111.74(18) . . ?
N1A C8A C9A 111.14(18) . . ?
C10A C8A C9A 111.20(18) . . ?
C16A C11A C12A 118.7(2) . . ?
C16A C11A C1A 123.00(18) . . ?
C12A C11A C1A 118.31(19) . . ?
C13A C12A C11A 120.8(2) . . ?
C12A C13A C14A 120.5(2) . . ?
C15A C14A C13A 118.7(2) . . ?
C14A C15A C16A 121.2(2) . . ?
C11A C16A C15A 120.0(2) . . ?

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
C11 C1 C2 C3 -108.0(2) . . . . ?
C4 C1 C2 C3 101.8(2) . . . . ?
C11 C1 C2 I1 141.50(16) . . . . ?
C3 C1 C2 I1 -110.5(2) . . . . ?
C4 C1 C2 I1 -8.7(3) . . . . ?
I1 C2 C3 C1 110.43(17) . . . . ?
C11 C1 C3 C2 109.8(2) . . . . ?
C4 C1 C3 C2 -112.30(19) . . . . ?
C8 N1 C4 O1 179.83(19) . . . . ?
C5 N1 C4 O1 -5.9(3) . . . . ?
C8 N1 C4 C1 -3.2(3) . . . . ?
C5 N1 C4 C1 171.07(19) . . . . ?
C11 C1 C4 O1 109.7(2) . . . . ?
C3 C1 C4 O1 -30.7(3) . . . . ?
C2 C1 C4 O1 -98.2(2) . . . . ?
C11 C1 C4 N1 -67.3(2) . . . . ?
C3 C1 C4 N1 152.29(18) . . . . ?
C2 C1 C4 N1 84.7(2) . . . . ?
C4 N1 C5 C6 66.9(3) . . . . ?
C8 N1 C5 C6 -118.5(3) . . . . ?
C4 N1 C5 C7 -61.5(3) . . . . ?
C8 N1 C5 C7 113.1(2) . . . . ?
C4 N1 C8 C10 -129.2(2) . . . . ?
C5 N1 C8 C10 56.4(3) . . . . ?
C4 N1 C8 C9 105.7(2) . . . . ?
C5 N1 C8 C9 -68.7(2) . . . . ?
C3 C1 C11 C16 -93.1(3) . . . . ?
C2 C1 C11 C16 -23.5(3) . . . . ?
C4 C1 C11 C16 128.7(2) . . . . ?
C3 C1 C11 C12 89.5(3) . . . . ?
C2 C1 C11 C12 159.1(2) . . . . ?
C4 C1 C11 C12 -48.7(2) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C1 C11 C12 C13 178.0(2) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C12 C13 C14 C15 1.2(4) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C12 C11 C16 C15 1.1(3) . . . . ?
C1 C11 C16 C15 -176.3(2) . . . . ?
C14 C15 C16 C11 -1.5(4) . . . . ?
C11A C1A C2A C3A -105.9(2) . . . . ?
C4A C1A C2A C3A 102.0(2) . . . . ?
C11A C1A C2A I1A 145.55(15) . . . . ?
C3A C1A C2A I1A -108.55(18) . . . . ?
C4A C1A C2A I1A -6.6(2) . . . . ?
I1A C2A C3A C1A 111.82(16) . . . . ?
C11A C1A C3A C2A 110.8(2) . . . . ?
C4A C1A C3A C2A -110.59(19) . . . . ?
C8A N1A C4A O1A 174.4(2) . . . . ?
C5A N1A C4A O1A -3.4(3) . . . . ?
C8A N1A C4A C1A -8.8(3) . . . . ?
C5A N1A C4A C1A 173.33(17) . . . . ?
C11A C1A C4A O1A 112.9(2) . . . . ?
C2A C1A C4A O1A -93.5(2) . . . . ?
C3A C1A C4A O1A -26.9(3) . . . . ?
C11A C1A C4A N1A -64.0(2) . . . . ?
C2A C1A C4A N1A 89.6(2) . . . . ?
C3A C1A C4A N1A 156.22(18) . . . . ?
C4A N1A C5A C7A 64.1(3) . . . . ?
C8A N1A C5A C7A -113.9(2) . . . . ?
C4A N1A C5A C6A -63.4(3) . . . . ?
C8A N1A C5A C6A 118.6(2) . . . . ?
C4A N1A C8A C10A -122.2(2) . . . . ?
C5A N1A C8A C10A 55.7(2) . . . . ?
C4A N1A C8A C9A 113.0(2) . . . . ?
C5A N1A C8A C9A -69.1(2) . . . . ?
C2A C1A C11A C16A -22.4(3) . . . . ?
C3A C1A C11A C16A -91.0(2) . . . . ?
C4A C1A C11A C16A 130.8(2) . . . . ?
C2A C1A C11A C12A 156.42(19) . . . . ?
C3A C1A C11A C12A 87.8(2) . . . . ?
C4A C1A C11A C12A -50.4(2) . . . . ?
C16A C11A C12A C13A -0.5(3) . . . . ?
C1A C11A C12A C13A -179.34(19) . . . . ?
C11A C12A C13A C14A -0.5(4) . . . . ?
C12A C13A C14A C15A 0.8(3) . . . . ?
C13A C14A C15A C16A 0.0(3) . . . . ?
C12A C11A C16A C15A 1.2(3) . . . . ?
C1A C11A C16A C15A -179.98(19) . . . . ?
C14A C15A C16A C11A -1.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.48
_refine_diff_density_min         -0.40
_refine_diff_density_rms         0.05

#===END of CIF

#------------------------------------------------------------------------
#There is a short intermolecular I1...O1A contact of 2.962(2) Angstroms,
#well within the sum of the van der Waals radii for the participating
#atoms (3.55 Angstroms). The C2-I1...O1A angle of 170.12(7) degrees is
#typical for such an interaction, the mean value from a search of the
#Cambridge Structural Database being 166(8) degrees. The I1...O1A-C4A
#angle of 172.7(2) degrees is less diagnostically useful, because of the
#very wide variation observed for this parameter, but it is not
#inconsistent with values in the CSD."