# Electronic Supplementary Material (ESI) for Organic .
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pnma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 I N O'
_chemical_formula_weight         405.26

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   Pnma

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

_cell_length_a                   20.3874(8)
_cell_length_b                   6.9055(3)
_cell_length_c                   12.3088(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1732.90(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5758
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      30.15

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    1.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_T_max  0.7210
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9013
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1755
_reflns_number_gt                1584
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1120P)²+0.3267P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1755
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C1 C 0.3707(2) 0.2500 0.2876(4) 0.0435(10) Uani 1 2 d S . .
C2 C 0.4018(2) 0.2500 0.1890(4) 0.0592(13) Uani 1 2 d S . .
H2 H 0.3784 0.2500 0.1241 0.071 Uiso 1 2 calc SR . .
C3 C 0.4694(3) 0.2500 0.1904(5) 0.088(2) Uani 1 2 d S . .
H3 H 0.4920 0.2500 0.1247 0.106 Uiso 1 2 calc SR . .
C4 C 0.5042(3) 0.2500 0.2849(5) 0.0783(19) Uani 1 2 d S . .
H4 H 0.5498 0.2500 0.2824 0.094 Uiso 1 2 calc SR . .
C5 C 0.4727(2) 0.2500 0.3848(4) 0.0609(15) Uani 1 2 d S . .
H5 H 0.4966 0.2500 0.4492 0.073 Uiso 1 2 calc SR . .
C6 C 0.4044(2) 0.2500 0.3862(3) 0.0426(10) Uani 1 2 d S . .
C7 C 0.35733(18) 0.2500 0.4793(3) 0.0385(9) Uani 1 2 d S . .
C8 C 0.29234(19) 0.2500 0.4174(3) 0.0353(8) Uani 1 2 d S . .
C9 C 0.2285(2) 0.2500 0.4638(3) 0.0430(9) Uani 1 2 d S . .
H9 H 0.1931 0.2500 0.4160 0.052 Uiso 1 2 calc SR . .
C10 C 0.21474(19) 0.2500 0.5710(3) 0.0423(9) Uani 1 2 d S . .
H10 H 0.2502 0.2500 0.6185 0.051 Uiso 1 2 calc SR . .
C11 C 0.1502(3) 0.2500 0.6189(3) 0.0478(11) Uani 1 2 d S . .
C12 C 0.0921(2) 0.2500 0.5592(4) 0.0731(17) Uani 1 2 d S . .
H12 H 0.0944 0.2500 0.4838 0.088 Uiso 1 2 calc SR . .
C13 C 0.0321(3) 0.2500 0.6076(4) 0.082(2) Uani 1 2 d S . .
H13 H -0.0058 0.2500 0.5655 0.098 Uiso 1 2 calc SR . .
C14 C 0.0277(2) 0.2500 0.7200(4) 0.0619(14) Uani 1 2 d S . .
C15 C 0.0845(2) 0.2500 0.7818(4) 0.0518(11) Uani 1 2 d S . .
H15 H 0.0817 0.2500 0.8572 0.062 Uiso 1 2 calc SR . .
C16 C 0.1446(2) 0.2500 0.7325(4) 0.0468(10) Uani 1 2 d S . .
H16 H 0.1824 0.2500 0.7749 0.056 Uiso 1 2 calc SR . .
C17 C 0.2526(2) 0.2500 0.2286(4) 0.0536(11) Uani 1 2 d S . .
H17A H 0.2323 0.3754 0.2251 0.080 Uiso 0.50 1 calc PR . .
H17B H 0.2200 0.1542 0.2452 0.080 Uiso 0.50 1 calc PR . .
H17C H 0.2724 0.2204 0.1598 0.080 Uiso 0.50 1 calc PR . .
C18 C 0.36543(15) 0.0635(4) 0.5470(2) 0.0487(7) Uani 1 1 d . . .
H18A H 0.3553 -0.0469 0.5027 0.073 Uiso 1 1 calc R . .
H18B H 0.3362 0.0673 0.6081 0.073 Uiso 1 1 calc R . .
H18C H 0.4098 0.0540 0.5724 0.073 Uiso 1 1 calc R . .
I1 I 0.326766(16) 0.2500 0.87257(3) 0.0585(3) Uani 1 2 d S . .
N1 N 0.30300(19) 0.2500 0.3135(3) 0.0397(8) Uani 1 2 d S . .
O1 O -0.03010(18) 0.2500 0.7736(3) 0.0830(14) Uani 1 2 d S . .
H1 H -0.0587 0.2951 0.7343 0.125 Uiso 0.50 1 calc PR . .

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
C1 0.040(2) 0.057(2) 0.034(2) 0.000 0.0012(17) 0.000
C2 0.055(3) 0.090(4) 0.033(2) 0.000 0.0063(19) 0.000
C3 0.058(3) 0.163(7) 0.044(3) 0.000 0.022(2) 0.000
C4 0.046(3) 0.130(6) 0.059(3) 0.000 0.015(2) 0.000
C5 0.035(2) 0.103(5) 0.044(3) 0.000 0.0031(17) 0.000
C6 0.040(2) 0.058(3) 0.031(2) 0.000 0.0028(15) 0.000
C7 0.0309(19) 0.056(2) 0.0289(19) 0.000 0.0005(15) 0.000
C8 0.036(2) 0.0426(19) 0.0277(19) 0.000 0.0002(15) 0.000
C9 0.0325(18) 0.057(2) 0.040(2) 0.000 -0.0006(15) 0.000
C10 0.0327(19) 0.055(2) 0.040(2) 0.000 -0.0026(15) 0.000
C11 0.034(2) 0.071(3) 0.038(3) 0.000 0.0016(15) 0.000
C12 0.037(2) 0.150(6) 0.032(2) 0.000 -0.0005(18) 0.000
C13 0.032(2) 0.173(7) 0.039(2) 0.000 -0.002(2) 0.000
C14 0.044(2) 0.098(4) 0.044(3) 0.000 0.008(2) 0.000
C15 0.049(2) 0.075(3) 0.032(2) 0.000 0.0058(17) 0.000
C16 0.046(2) 0.058(2) 0.037(2) 0.000 -0.0063(17) 0.000
C17 0.045(2) 0.078(3) 0.038(2) 0.000 -0.0149(18) 0.000
C18 0.0505(16) 0.0588(18) 0.0369(14) 0.0067(12) 0.0005(12) 0.0114(13)
I1 0.0542(3) 0.0754(4) 0.0459(3) 0.000 -0.00675(11) 0.000
N1 0.0402(18) 0.0461(18) 0.0329(18) 0.000 -0.0003(15) 0.000
O1 0.0416(19) 0.158(5) 0.049(2) 0.000 0.0141(16) 0.000

_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
C1 C2 1.370(6) . ?
C1 C6 1.394(6) . ?
C1 N1 1.416(6) . ?
C2 C3 1.380(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(5) . ?
C7 C8 1.528(6) . ?
C7 C18 1.543(3) 7_565 ?
C7 C18 1.543(3) . ?
C8 N1 1.297(6) . ?
C8 C9 1.421(6) . ?
C9 C10 1.349(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.442(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(6) . ?
C11 C16 1.403(6) . ?
C12 C13 1.360(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(7) . ?
C13 H13 0.9300 . ?
C14 O1 1.350(6) . ?
C14 C15 1.385(7) . ?
C15 C16 1.369(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N1 1.467(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O1 H1 0.8200 . ?

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 C1 C6 122.9(4) . . ?
C2 C1 N1 130.6(4) . . ?
C6 C1 N1 106.5(4) . . ?
C1 C2 C3 116.8(5) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 122.1(5) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.3(5) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 118.8(4) . . ?
C5 C6 C7 130.6(4) . . ?
C1 C6 C7 110.6(4) . . ?
C6 C7 C8 100.0(3) . . ?
C6 C7 C18 110.2(2) . 7_565 ?
C8 C7 C18 111.2(2) . 7_565 ?
C6 C7 C18 110.2(2) . . ?
C8 C7 C18 111.2(2) . . ?
C18 C7 C18 113.2(3) 7_565 . ?
N1 C8 C9 123.3(4) . . ?
N1 C8 C7 110.3(3) . . ?
C9 C8 C7 126.4(4) . . ?
C10 C9 C8 125.7(4) . . ?
C10 C9 H9 117.2 . . ?
C8 C9 H9 117.2 . . ?
C9 C10 C11 126.1(4) . . ?
C9 C10 H10 116.9 . . ?
C11 C10 H10 116.9 . . ?
C12 C11 C16 117.1(4) . . ?
C12 C11 C10 124.1(4) . . ?
C16 C11 C10 118.8(4) . . ?
C13 C12 C11 122.3(4) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 119.7(5) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
O1 C14 C15 117.5(5) . . ?
O1 C14 C13 123.0(5) . . ?
C15 C14 C13 119.6(4) . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 N1 C1 112.7(3) . . ?
C8 N1 C17 125.8(4) . . ?
C1 N1 C17 121.5(4) . . ?
C14 O1 H1 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
C6 C1 C2 C3 0.0 . . . . ?
N1 C1 C2 C3 180.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 180.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
N1 C1 C6 C5 180.0 . . . . ?
C2 C1 C6 C7 180.0 . . . . ?
N1 C1 C6 C7 0.0 . . . . ?
C5 C6 C7 C8 180.0 . . . . ?
C1 C6 C7 C8 0.0 . . . . ?
C5 C6 C7 C18 62.8(2) . . . 7_565 ?
C1 C6 C7 C18 -117.2(2) . . . 7_565 ?
C5 C6 C7 C18 -62.8(2) . . . . ?
C1 C6 C7 C18 117.2(2) . . . . ?
C6 C7 C8 N1 0.0 . . . . ?
C18 C7 C8 N1 116.4(2) 7_565 . . . ?
C18 C7 C8 N1 -116.4(2) . . . . ?
C6 C7 C8 C9 180.0 . . . . ?
C18 C7 C8 C9 -63.6(2) 7_565 . . . ?
C18 C7 C8 C9 63.6(2) . . . . ?
N1 C8 C9 C10 180.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 180.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C9 C10 C11 C16 180.0 . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C10 C11 C12 C13 180.0 . . . . ?
C11 C12 C13 C14 0.000(1) . . . . ?
C12 C13 C14 O1 180.0 . . . . ?
C12 C13 C14 C15 0.000(1) . . . . ?
O1 C14 C15 C16 180.000(1) . . . . ?
C13 C14 C15 C16 0.000(1) . . . . ?
C14 C15 C16 C11 0.000(1) . . . . ?
C12 C11 C16 C15 0.000(1) . . . . ?
C10 C11 C16 C15 180.0 . . . . ?
C9 C8 N1 C1 180.0 . . . . ?
C7 C8 N1 C1 0.0 . . . . ?
C9 C8 N1 C17 0.0 . . . . ?
C7 C8 N1 C17 180.0 . . . . ?
C2 C1 N1 C8 180.0 . . . . ?
C6 C1 N1 C8 0.0 . . . . ?
C2 C1 N1 C17 0.0 . . . . ?
C6 C1 N1 C17 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 970856'
