# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1422194'
_audit_update_record             
;
2015-09-03 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 I N3 O0'
_chemical_formula_weight         349.17

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   'P2(1)/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                   8.7065(17)
_cell_length_b                   13.352(3)
_cell_length_c                   11.519(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.24(3)
_cell_angle_gamma                90.00
_cell_volume                     1321.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4398
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    2.408
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4771
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2315
_reflns_number_gt                2139
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2315
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.71217(3) 0.072424(18) 0.78272(2) 0.02315(18) Uani 1 1 d . . .
N1 N 0.9148(3) 0.2868(2) 0.8121(3) 0.0180(6) Uani 1 1 d . . .
N2 N 0.9108(3) 0.2858(2) 0.6932(3) 0.0208(7) Uani 1 1 d . . .
C4 C 1.4114(4) 0.2853(3) 0.8933(3) 0.0261(9) Uani 1 1 d . . .
H4A H 1.4710 0.3253 0.8517 0.031 Uiso 1 1 calc R . .
C14 C 0.8402(4) 0.3702(3) 0.8435(3) 0.0165(7) Uani 1 1 d . . .
C2 C 1.3922(4) 0.1786(3) 1.0543(3) 0.0245(8) Uani 1 1 d . . .
H2A H 1.4406 0.1445 1.1206 0.029 Uiso 1 1 calc R . .
C1 C 1.2364(4) 0.1725(3) 1.0242(3) 0.0225(8) Uani 1 1 d . . .
H1A H 1.1788 0.1359 1.0707 0.027 Uiso 1 1 calc R . .
C7 C 0.9859(4) 0.2064(3) 0.8875(3) 0.0189(7) Uani 1 1 d . . .
H7A H 0.9388 0.2062 0.9593 0.023 Uiso 1 1 calc R . .
C11 C 0.6856(5) 0.5483(3) 0.8419(4) 0.0272(9) Uani 1 1 d . . .
H11A H 0.6361 0.6098 0.8442 0.033 Uiso 1 1 calc R . .
C10 C 0.7093(4) 0.5107(3) 0.7346(4) 0.0223(8) Uani 1 1 d . . .
H10A H 0.6740 0.5440 0.6645 0.027 Uiso 1 1 calc R . .
C8 C 0.9569(4) 0.1053(3) 0.8291(3) 0.0213(8) Uani 1 1 d . . .
H8A H 1.0058 0.0539 0.8819 0.026 Uiso 1 1 calc R . .
H8B H 1.0047 0.1038 0.7586 0.026 Uiso 1 1 calc R . .
C6 C 1.1604(4) 0.2213(3) 0.9226(3) 0.0181(7) Uani 1 1 d . . .
C12 C 0.7335(4) 0.4970(3) 0.9472(4) 0.0277(9) Uani 1 1 d . . .
H12A H 0.7105 0.5244 1.0166 0.033 Uiso 1 1 calc R . .
C13 C 0.8138(5) 0.4070(3) 0.9528(4) 0.0224(8) Uani 1 1 d . . .
H13A H 0.8475 0.3738 1.0232 0.027 Uiso 1 1 calc R . .
C5 C 1.2491(4) 0.2779(3) 0.8567(3) 0.0246(8) Uani 1 1 d . . .
H5A H 1.2019 0.3106 0.7890 0.029 Uiso 1 1 calc R . .
N3 N 0.8364(3) 0.3648(3) 0.6466(3) 0.0224(7) Uani 1 1 d . . .
C3 C 1.4808(4) 0.2335(3) 0.9902(3) 0.0239(8) Uani 1 1 d . . .
H3A H 1.5882 0.2357 1.0122 0.029 Uiso 1 1 calc R . .
C9 C 0.7900(4) 0.4187(3) 0.7369(4) 0.0178(9) Uani 1 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 0.0192(2) 0.0154(3) 0.0350(3) 0.00006(9) 0.00503(15) -0.00247(8)
N1 0.0193(15) 0.0090(15) 0.0263(15) -0.0005(12) 0.0053(12) -0.0011(12)
N2 0.0233(16) 0.0143(17) 0.0269(15) 0.0001(13) 0.0101(13) 0.0001(13)
C4 0.0203(19) 0.026(2) 0.033(2) 0.0008(17) 0.0070(16) -0.0041(16)
C14 0.0116(15) 0.0091(18) 0.0289(18) -0.0011(14) 0.0036(14) -0.0032(13)
C2 0.025(2) 0.020(2) 0.0258(18) -0.0008(16) -0.0011(16) 0.0055(16)
C1 0.0215(19) 0.016(2) 0.0293(18) 0.0000(16) 0.0030(16) -0.0002(16)
C7 0.0172(17) 0.0146(19) 0.0249(17) 0.0013(15) 0.0033(14) 0.0030(14)
C11 0.0209(19) 0.0111(18) 0.051(3) -0.0004(19) 0.0109(19) -0.0005(17)
C10 0.0144(16) 0.017(2) 0.036(2) 0.0080(17) 0.0059(15) -0.0015(15)
C8 0.0151(17) 0.015(2) 0.033(2) 0.0009(17) 0.0018(15) 0.0004(16)
C6 0.0226(18) 0.0072(17) 0.0247(17) 0.0000(14) 0.0038(15) 0.0039(14)
C12 0.027(2) 0.021(2) 0.037(2) -0.0108(18) 0.0110(17) 0.0007(17)
C13 0.025(2) 0.0150(18) 0.028(2) -0.0025(16) 0.0047(17) -0.0054(16)
C5 0.025(2) 0.021(2) 0.0272(18) 0.0017(17) 0.0027(16) 0.0009(17)
N3 0.0208(15) 0.0204(18) 0.0259(16) 0.0068(14) 0.0034(13) 0.0017(14)
C3 0.0169(17) 0.024(2) 0.0303(19) -0.0050(17) 0.0021(15) 0.0028(16)
C9 0.015(2) 0.010(2) 0.0294(19) 0.0051(14) 0.0082(16) -0.0030(12)

_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 C8 2.157(4) . ?
N1 N2 1.364(4) . ?
N1 C14 1.367(5) . ?
N1 C7 1.455(5) . ?
N2 N3 1.308(4) . ?
C4 C3 1.368(5) . ?
C4 C5 1.412(5) . ?
C4 H4A 0.9300 . ?
C14 C9 1.395(6) . ?
C14 C13 1.404(5) . ?
C2 C1 1.348(5) . ?
C2 C3 1.364(5) . ?
C2 H2A 0.9300 . ?
C1 C6 1.408(5) . ?
C1 H1A 0.9300 . ?
C7 C8 1.512(5) . ?
C7 C6 1.522(5) . ?
C7 H7A 0.9800 . ?
C11 C10 1.381(6) . ?
C11 C12 1.397(6) . ?
C11 H11A 0.9300 . ?
C10 C9 1.413(5) . ?
C10 H10A 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 C5 1.390(5) . ?
C12 C13 1.386(6) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C5 H5A 0.9300 . ?
N3 C9 1.377(5) . ?
C3 H3A 0.9300 . ?

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
N2 N1 C14 109.7(3) . . ?
N2 N1 C7 122.1(3) . . ?
C14 N1 C7 128.1(3) . . ?
N3 N2 N1 109.5(3) . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
N1 C14 C9 103.9(3) . . ?
N1 C14 C13 132.5(4) . . ?
C9 C14 C13 123.6(4) . . ?
C1 C2 C3 121.7(4) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C2 C1 C6 120.4(4) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
N1 C7 C8 111.6(3) . . ?
N1 C7 C6 111.9(3) . . ?
C8 C7 C6 108.8(3) . . ?
N1 C7 H7A 108.1 . . ?
C8 C7 H7A 108.1 . . ?
C6 C7 H7A 108.1 . . ?
C10 C11 C12 122.2(4) . . ?
C10 C11 H11A 118.9 . . ?
C12 C11 H11A 118.9 . . ?
C11 C10 C9 116.4(4) . . ?
C11 C10 H10A 121.8 . . ?
C9 C10 H10A 121.8 . . ?
C7 C8 I1 112.3(2) . . ?
C7 C8 H8A 109.1 . . ?
I1 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
I1 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 123.0(3) . . ?
C1 C6 C7 118.5(3) . . ?
C13 C12 C11 122.9(4) . . ?
C13 C12 H12A 118.5 . . ?
C11 C12 H12A 118.5 . . ?
C12 C13 C14 114.6(4) . . ?
C12 C13 H13A 122.7 . . ?
C14 C13 H13A 122.7 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
N2 N3 C9 107.3(3) . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
N3 C9 C14 109.5(3) . . ?
N3 C9 C10 130.1(4) . . ?
C14 C9 C10 120.3(4) . . ?

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
C14 N1 N2 N3 -0.2(4) . . . . ?
C7 N1 N2 N3 178.0(3) . . . . ?
N2 N1 C14 C9 0.5(4) . . . . ?
C7 N1 C14 C9 -177.6(3) . . . . ?
N2 N1 C14 C13 -178.9(4) . . . . ?
C7 N1 C14 C13 3.0(6) . . . . ?
C3 C2 C1 C6 1.6(6) . . . . ?
N2 N1 C7 C8 -37.2(4) . . . . ?
C14 N1 C7 C8 140.7(3) . . . . ?
N2 N1 C7 C6 85.1(4) . . . . ?
C14 N1 C7 C6 -97.0(4) . . . . ?
C12 C11 C10 C9 -2.3(6) . . . . ?
N1 C7 C8 I1 -58.8(3) . . . . ?
C6 C7 C8 I1 177.2(2) . . . . ?
C2 C1 C6 C5 -1.9(5) . . . . ?
C2 C1 C6 C7 175.8(3) . . . . ?
N1 C7 C6 C5 -24.1(5) . . . . ?
C8 C7 C6 C5 99.7(4) . . . . ?
N1 C7 C6 C1 158.3(3) . . . . ?
C8 C7 C6 C1 -77.9(4) . . . . ?
C10 C11 C12 C13 2.8(6) . . . . ?
C11 C12 C13 C14 -1.4(6) . . . . ?
N1 C14 C13 C12 179.0(4) . . . . ?
C9 C14 C13 C12 -0.3(5) . . . . ?
C1 C6 C5 C4 -0.3(5) . . . . ?
C7 C6 C5 C4 -177.9(3) . . . . ?
C3 C4 C5 C6 2.8(6) . . . . ?
N1 N2 N3 C9 -0.2(4) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C5 C4 C3 C2 -3.1(6) . . . . ?
N2 N3 C9 C14 0.5(4) . . . . ?
N2 N3 C9 C10 178.5(4) . . . . ?
N1 C14 C9 N3 -0.6(4) . . . . ?
C13 C14 C9 N3 178.9(3) . . . . ?
N1 C14 C9 C10 -178.8(3) . . . . ?
C13 C14 C9 C10 0.7(5) . . . . ?
C11 C10 C9 N3 -177.2(4) . . . . ?
C11 C10 C9 C14 0.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.676
_refine_diff_density_min         -1.418
_refine_diff_density_rms         0.148
