# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_red
_database_code_depnum_ccdc_archive 'CCDC 1435261'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;
_audit_creation_date             2015-11-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        amit
_chemical_formula_moiety         'C15 H15 I N4'
_chemical_formula_sum            'C15 H15 I N4'
_chemical_formula_weight         378.21
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_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                   7.5445(7)
_cell_length_b                   14.1434(15)
_cell_length_c                   14.8389(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.417(4)
_cell_angle_gamma                90
_cell_volume                     1557.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    298
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.052
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0728 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.8020.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22538
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.005
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2536
_reflns_number_total             2739
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2739
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+2.5208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0943
_refine_special_details          ?
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.17340(4) 0.22049(2) -0.11913(2) 0.06845(15) Uani 1 1 d . . . . .
N1 N 0.5409(4) 0.3207(2) 0.09384(18) 0.0435(7) Uani 1 1 d . . . . .
N2 N 0.3877(4) 0.1829(2) 0.08757(19) 0.0484(7) Uani 1 1 d . . . . .
N3 N 0.4714(4) 0.3653(2) -0.0664(2) 0.0493(7) Uani 1 1 d . . . . .
C1 C 1.1611(7) 0.4557(6) 0.1344(4) 0.099(2) Uani 1 1 d . . . . .
H1A H 1.2157 0.4020 0.1682 0.149 Uiso 1 1 calc GR . . . .
H1B H 1.2302 0.5114 0.1538 0.149 Uiso 1 1 calc GR . . . .
H1C H 1.1580 0.4457 0.0701 0.149 Uiso 1 1 calc GR . . . .
C2 C 0.9713(6) 0.4681(4) 0.1518(4) 0.0778(14) Uani 1 1 d . . . . .
H2A H 0.9753 0.4771 0.2170 0.093 Uiso 1 1 calc R . . . .
H2B H 0.9197 0.5247 0.1206 0.093 Uiso 1 1 calc R . . . .
C3 C 0.8514(6) 0.3850(4) 0.1196(3) 0.0662(11) Uani 1 1 d . . . . .
H3A H 0.8999 0.3291 0.1531 0.079 Uiso 1 1 calc R . . . .
H3B H 0.8527 0.3741 0.0552 0.079 Uiso 1 1 calc R . . . .
C4 C 0.6583(5) 0.3990(3) 0.1324(3) 0.0529(9) Uani 1 1 d . . . . .
H4A H 0.6556 0.4046 0.1973 0.063 Uiso 1 1 calc R . . . .
H4B H 0.6125 0.4575 0.1030 0.063 Uiso 1 1 calc R . . . .
C5 C 0.4620(4) 0.3088(3) 0.0042(2) 0.0404(7) Uani 1 1 d . . . . .
C6 C 0.3670(5) 0.2233(3) 0.0009(2) 0.0409(8) Uani 1 1 d . . . . .
C7 C 0.2731(5) 0.1949(3) -0.0843(2) 0.0429(8) Uani 1 1 d . . . . .
C8 C 0.1732(5) 0.1037(3) -0.0987(2) 0.0430(8) Uani 1 1 d . . . . .
C9 C -0.0128(5) 0.0978(3) -0.1157(2) 0.0467(8) Uani 1 1 d . . . . .
C10 C -0.1005(6) 0.0109(3) -0.1268(3) 0.0555(10) Uani 1 1 d . . . . .
H10 H -0.2257 0.0084 -0.1372 0.067 Uiso 1 1 calc R . . . .
C11 C -0.0026(7) -0.0709(3) -0.1223(3) 0.0642(11) Uani 1 1 d . . . . .
H11 H -0.0609 -0.1290 -0.1301 0.077 Uiso 1 1 calc R . . . .
C12 C 0.4903(5) 0.2438(3) 0.1392(2) 0.0507(9) Uani 1 1 d . . . . .
H12 H 0.5262 0.2355 0.2020 0.061 Uiso 1 1 calc R . . . .
C13 C 0.3739(6) 0.3306(3) -0.1441(2) 0.0544(9) Uani 1 1 d . . . . .
H13 H 0.3737 0.3671 -0.1962 0.065 Uiso 1 1 calc R . . . .
N14 N 0.2778(5) 0.2514(3) -0.1569(2) 0.0520(8) Uani 1 1 d . . . . .
C15 C 0.1830(7) -0.0667(3) -0.1061(3) 0.0660(12) Uani 1 1 d . . . . .
H15 H 0.2451 -0.1237 -0.1039 0.079 Uiso 1 1 calc R . . . .
C16 C 0.2817(6) 0.0131(3) -0.0931(2) 0.0532(10) Uani 1 1 d . . . . .
H16 H 0.4071 0.0126 -0.0817 0.064 Uiso 1 1 calc R . . . .


_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 C9 2.111(4) . ?
N1 C4 1.468(5) . ?
N1 C5 1.366(4) . ?
N1 C12 1.368(5) . ?
N2 C6 1.390(4) . ?
N2 C12 1.310(5) . ?
N3 C5 1.328(5) . ?
N3 C13 1.343(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.511(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.507(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.515(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.402(5) . ?
C6 C7 1.392(5) . ?
C7 C8 1.490(5) . ?
C7 N14 1.348(5) . ?
C8 C9 1.383(5) . ?
C8 C16 1.515(6) . ?
C9 C10 1.392(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(6) . ?
C11 H11 0.9300 . ?
C11 C15 1.378(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 N14 1.329(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.347(6) . ?
C16 H16 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
C5 N1 C4 126.7(3) . . ?
C5 N1 C12 105.7(3) . . ?
C12 N1 C4 127.6(3) . . ?
C12 N2 C6 103.0(3) . . ?
C5 N3 C13 110.9(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.8(5) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.2(4) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
N1 C4 C3 112.3(3) . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C6 105.6(3) . . ?
N3 C5 N1 128.2(3) . . ?
N3 C5 C6 126.3(3) . . ?
N2 C6 C5 110.6(3) . . ?
N2 C6 C7 132.4(3) . . ?
C7 C6 C5 117.0(3) . . ?
C6 C7 C8 122.8(3) . . ?
N14 C7 C6 118.2(3) . . ?
N14 C7 C8 119.0(3) . . ?
C7 C8 C16 118.0(3) . . ?
C9 C8 C7 123.3(3) . . ?
C9 C8 C16 118.7(3) . . ?
C8 C9 I1 121.0(3) . . ?
C8 C9 C10 121.3(4) . . ?
C10 C9 I1 117.7(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C15 119.7(4) . . ?
C15 C11 H11 120.2 . . ?
N1 C12 H12 122.5 . . ?
N2 C12 N1 115.0(3) . . ?
N2 C12 H12 122.5 . . ?
N3 C13 H13 115.4 . . ?
N14 C13 N3 129.1(3) . . ?
N14 C13 H13 115.4 . . ?
C13 N14 C7 118.5(3) . . ?
C11 C15 H15 117.3 . . ?
C16 C15 C11 125.4(4) . . ?
C16 C15 H15 117.3 . . ?
C8 C16 H16 122.5 . . ?
C15 C16 C8 114.9(4) . . ?
C15 C16 H16 122.5 . . ?

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
I1 C9 C10 C11 -178.0(3) . . . . ?
N1 C5 C6 N2 -0.1(4) . . . . ?
N1 C5 C6 C7 179.9(3) . . . . ?
N2 C6 C7 C8 -2.7(6) . . . . ?
N2 C6 C7 N14 179.2(4) . . . . ?
N3 C5 C6 N2 179.7(3) . . . . ?
N3 C5 C6 C7 -0.2(5) . . . . ?
N3 C13 N14 C7 -0.4(7) . . . . ?
C1 C2 C3 C4 -177.0(4) . . . . ?
C2 C3 C4 N1 175.4(4) . . . . ?
C4 N1 C5 N3 -1.2(6) . . . . ?
C4 N1 C5 C6 178.7(3) . . . . ?
C4 N1 C12 N2 -178.3(3) . . . . ?
C5 N1 C4 C3 -81.9(5) . . . . ?
C5 N1 C12 N2 0.6(4) . . . . ?
C5 N3 C13 N14 -0.6(6) . . . . ?
C5 C6 C7 C8 177.2(3) . . . . ?
C5 C6 C7 N14 -0.9(5) . . . . ?
C6 N2 C12 N1 -0.6(4) . . . . ?
C6 C7 C8 C9 108.2(4) . . . . ?
C6 C7 C8 C16 -71.1(4) . . . . ?
C6 C7 N14 C13 1.1(5) . . . . ?
C7 C8 C9 I1 -1.7(4) . . . . ?
C7 C8 C9 C10 -178.6(3) . . . . ?
C7 C8 C16 C15 179.5(3) . . . . ?
C8 C7 N14 C13 -177.0(4) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C9 C8 C16 C15 0.2(5) . . . . ?
C9 C10 C11 C15 0.5(6) . . . . ?
C10 C11 C15 C16 0.5(7) . . . . ?
C11 C15 C16 C8 -0.8(6) . . . . ?
C12 N1 C4 C3 96.7(5) . . . . ?
C12 N1 C5 N3 179.9(4) . . . . ?
C12 N1 C5 C6 -0.2(4) . . . . ?
C12 N2 C6 C5 0.5(4) . . . . ?
C12 N2 C6 C7 -179.6(4) . . . . ?
C13 N3 C5 N1 -179.3(4) . . . . ?
C13 N3 C5 C6 0.9(5) . . . . ?
N14 C7 C8 C9 -73.8(4) . . . . ?
N14 C7 C8 C16 107.0(4) . . . . ?
C16 C8 C9 I1 177.5(2) . . . . ?
C16 C8 C9 C10 0.6(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id Amit
_olex2_submission_special_instructions 'No special instructions were received'
