# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2011ncs0537
_database_code_depnum_ccdc_archive 'CCDC 1042672'

_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_date             2015-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.25 svn.r3098 for OlexSys, GUI svn.r4951)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'I, C15 H18 N O2'
_chemical_formula_sum            'C15 H18 I N O2'
_chemical_formula_weight         371.20
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3649(2)
_cell_length_b                   15.0028(4)
_cell_length_c                   11.1821(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.996(7)
_cell_angle_gamma                90.00
_cell_volume                     1568.93(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    2.039
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17143
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.08
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3416
_reflns_number_total             3585
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0143
_refine_ls_R_factor_gt           0.0134
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0151P)²+0.7348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0337
_refine_ls_wR_factor_ref         0.0340
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C003(H00A,H00B), C007(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C010(H010), C011(H011), C012(H012), C013(H013),
 C016(H016), C017(H017), C018(H018)
2.d Idealised Me refined as rotating group:
 C009(H00E,H00F,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I1 I 0.033869(8) 0.709595(5) 0.016739(7) 0.01572(3) Uani 1 d . . .
C003 C -0.44866(14) 0.70389(8) -0.13199(12) 0.0171(2) Uani 1 d . . .
H00A H -0.4174 0.6734 -0.0566 0.020 Uiso 1 calc . . R
H00B H -0.3783 0.6912 -0.1929 0.020 Uiso 1 calc . . R
N004 N -0.39098(11) 1.11802(7) -0.14340(9) 0.0142(2) Uani 1 d . . .
C005 C -0.69154(14) 0.51698(9) -0.14346(12) 0.0202(3) Uani 1 d . . .
H005 H -0.7461 0.5401 -0.0812 0.024 Uiso 1 calc . . R
C006 C -0.32840(13) 0.83977(8) -0.08298(11) 0.0147(2) Uani 1 d . . .
H006 H -0.2546 0.8180 -0.1375 0.018 Uiso 1 calc . . R
C007 C -0.59584(13) 0.67211(8) -0.17497(11) 0.0163(2) Uani 1 d . . .
H00C H -0.6271 0.7060 -0.2477 0.020 Uiso 1 calc . . R
H00D H -0.6640 0.6850 -0.1125 0.020 Uiso 1 calc . . R
C008 C -0.51925(14) 0.53748(9) -0.29255(11) 0.0177(2) Uani 1 d . . .
H008 H -0.4560 0.5748 -0.3335 0.021 Uiso 1 calc . . R
C009 C -0.41459(15) 1.21454(8) -0.16391(12) 0.0177(3) Uani 1 d . . .
H00E H -0.4995 1.2337 -0.1232 0.027 Uiso 1 calc . . GR
H00F H -0.4289 1.2259 -0.2500 0.027 Uiso 1 calc . . GR
H00G H -0.3310 1.2479 -0.1321 0.027 Uiso 1 calc . . GR
C010 C -0.32825(13) 1.09032(8) -0.03896(11) 0.0148(2) Uani 1 d . . .
H010 H -0.2976 1.1329 0.0198 0.018 Uiso 1 calc . . R
C011 C -0.30798(13) 1.00067(8) -0.01651(11) 0.0145(2) Uani 1 d . . .
H011 H -0.2636 0.9815 0.0574 0.017 Uiso 1 calc . . R
C012 C -0.62213(15) 0.39230(9) -0.26327(13) 0.0216(3) Uani 1 d . . .
H012 H -0.6302 0.3311 -0.2844 0.026 Uiso 1 calc . . R
C013 C -0.43611(15) 1.05894(9) -0.22851(11) 0.0204(3) Uani 1 d . . .
H013 H -0.4806 1.0797 -0.3015 0.024 Uiso 1 calc . . R
C014 C -0.60119(13) 0.57350(8) -0.20340(11) 0.0153(2) Uani 1 d . . .
C015 C -0.35293(13) 0.93853(8) -0.10275(11) 0.0142(2) Uani 1 d . . .
C016 C -0.70289(15) 0.42698(9) -0.17361(13) 0.0230(3) Uani 1 d . . .
H016 H -0.7659 0.3894 -0.1328 0.028 Uiso 1 calc . . R
C017 C -0.52950(14) 0.44744(9) -0.32181(12) 0.0206(3) Uani 1 d . . .
H017 H -0.4728 0.4236 -0.3822 0.025 Uiso 1 calc . . R
C018 C -0.41795(15) 0.96882(9) -0.21007(11) 0.0199(3) Uani 1 d . . .
H018 H -0.4496 0.9275 -0.2702 0.024 Uiso 1 calc . . R
O1 O -0.46007(10) 0.79823(6) -0.11287(8) 0.01536(18) Uani 1 d . . .
O2 O -0.28278(11) 0.82315(6) 0.03628(8) 0.01831(19) Uani 1 d . . .
H2 H -0.214(2) 0.7946(12) 0.0353(18) 0.032(5) Uiso 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01563(5) 0.01775(5) 0.01382(5) 0.00123(3) 0.00113(3) 0.00122(3)
C003 0.0184(6) 0.0108(6) 0.0217(6) -0.0029(5) -0.0015(5) 0.0012(5)
N004 0.0139(5) 0.0135(5) 0.0152(5) 0.0004(4) 0.0009(4) -0.0005(4)
C005 0.0201(6) 0.0198(6) 0.0209(6) 0.0000(5) 0.0032(5) -0.0012(5)
C006 0.0137(6) 0.0141(6) 0.0163(6) -0.0022(4) 0.0002(4) 0.0002(4)
C007 0.0161(6) 0.0139(6) 0.0191(6) -0.0026(5) 0.0016(5) -0.0005(5)
C008 0.0149(6) 0.0174(6) 0.0206(6) -0.0023(5) -0.0001(5) -0.0016(5)
C009 0.0218(6) 0.0130(6) 0.0183(6) 0.0020(4) 0.0007(5) 0.0008(5)
C010 0.0141(6) 0.0162(6) 0.0140(5) -0.0028(4) 0.0000(4) 0.0002(5)
C011 0.0123(5) 0.0161(6) 0.0151(5) -0.0006(5) -0.0003(4) 0.0006(5)
C012 0.0230(7) 0.0117(6) 0.0290(7) -0.0004(5) -0.0101(5) 0.0028(5)
C013 0.0264(7) 0.0196(6) 0.0146(6) 0.0006(5) -0.0049(5) -0.0019(5)
C014 0.0146(6) 0.0142(6) 0.0168(6) -0.0012(4) -0.0022(4) -0.0002(5)
C015 0.0122(5) 0.0145(6) 0.0160(5) -0.0012(4) 0.0026(4) -0.0001(4)
C016 0.0238(7) 0.0173(6) 0.0277(7) 0.0062(5) -0.0018(5) -0.0043(5)
C017 0.0173(6) 0.0201(7) 0.0240(6) -0.0069(5) -0.0028(5) 0.0048(5)
C018 0.0265(7) 0.0170(6) 0.0156(6) -0.0026(5) -0.0032(5) -0.0023(5)
O1 0.0145(4) 0.0108(4) 0.0206(4) -0.0029(3) -0.0011(3) -0.0004(3)
O2 0.0184(5) 0.0169(5) 0.0192(5) -0.0002(4) -0.0040(4) 0.0038(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
C003 C007 1.5129(18) . ?
C003 O1 1.4362(14) . ?
N004 C009 1.4809(15) . ?
N004 C010 1.3453(16) . ?
N004 C013 1.3520(16) . ?
C005 C014 1.3940(18) . ?
C005 C016 1.3945(19) . ?
C006 C015 1.5138(17) . ?
C006 O1 1.4063(15) . ?
C006 O2 1.4013(15) . ?
C007 C014 1.5135(17) . ?
C008 C014 1.3981(18) . ?
C008 C017 1.3920(19) . ?
C010 C011 1.3795(17) . ?
C011 C015 1.3907(16) . ?
C012 C016 1.388(2) . ?
C012 C017 1.387(2) . ?
C013 C018 1.3769(19) . ?
C015 C018 1.3932(17) . ?

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
O1 C003 C007 106.51(10) . . ?
C010 N004 C009 119.43(10) . . ?
C010 N004 C013 120.98(11) . . ?
C013 N004 C009 119.56(11) . . ?
C014 C005 C016 120.88(13) . . ?
O1 C006 C015 105.94(10) . . ?
O2 C006 C015 110.46(10) . . ?
O2 C006 O1 111.54(10) . . ?
C003 C007 C014 113.23(10) . . ?
C017 C008 C014 120.60(12) . . ?
N004 C010 C011 120.59(11) . . ?
C010 C011 C015 119.58(11) . . ?
C017 C012 C016 119.67(12) . . ?
N004 C013 C018 120.45(12) . . ?
C005 C014 C007 120.51(12) . . ?
C005 C014 C008 118.51(12) . . ?
C008 C014 C007 120.95(11) . . ?
C011 C015 C006 121.12(11) . . ?
C011 C015 C018 118.78(11) . . ?
C018 C015 C006 120.08(11) . . ?
C012 C016 C005 119.99(13) . . ?
C012 C017 C008 120.32(13) . . ?
C013 C018 C015 119.63(12) . . ?
C006 O1 C003 113.64(10) . . ?
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'
