# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is © The Owner Societies 2011


data_global
_journal_name_full               Phys.Chem.Chem.Phys.(PCCP)
_journal_coden_cambridge         1326
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       morton@citrus.ucr.edu
_publ_contact_author_name        'Thomas Morton'
loop_
_publ_author_name
'Thomas Morton'
'Gregory J.O.Beran'
'Eric Chronister'
'Luke Daemen'
'Aaron Moehlig'
'Leonard Mueller'
'Jos Oomens'
'Andrew Rice'
'David Santiago-Dieppa'
'Fook Tham'
'Kelly Theel'
'Sepideh Yaghmaei'

data_tm13-no-hsym
_database_code_depnum_ccdc_archive 'CCDC 831398'
#TrackingRef '- tm13-no-Hsym.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H21 I N2'
_chemical_formula_weight         272.17

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'
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   Cmcm

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

_cell_length_a                   8.8848(6)
_cell_length_b                   10.8203(7)
_cell_length_c                   11.8758(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1141.69(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    3730
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      30.37

_exptl_crystal_description       'thin plate frag'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    2.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6340
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         30.02
_reflns_number_total             923
_reflns_number_gt                863
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0211P)^2^+1.3735P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         923
_refine_ls_number_parameters     55
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0446
_refine_ls_wR_factor_gt          0.0437
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.071
_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
I1 I 0.5000 0.69496(2) 0.7500 0.01833(8) Uani 1 4 d S . .
C1 C 0.6429(7) 0.6195(5) 0.3999(6) 0.0204(11) Uani 0.50 1 d PDU A -1
H1A H 0.6207 0.5347 0.3760 0.031 Uiso 0.50 1 calc PR A -1
H1B H 0.6487 0.6228 0.4822 0.031 Uiso 0.50 1 calc PR A -1
H1C H 0.7393 0.6457 0.3677 0.031 Uiso 0.50 1 calc PR A -1
C2 C 0.3760(6) 0.6640(5) 0.4074(5) 0.0220(11) Uani 0.50 1 d PDU A -1
H2A H 0.3559 0.5780 0.3862 0.033 Uiso 0.50 1 calc PR A -1
H2B H 0.2961 0.7172 0.3776 0.033 Uiso 0.50 1 calc PR A -1
H2C H 0.3788 0.6709 0.4897 0.033 Uiso 0.50 1 calc PR A -1
N1 N 0.5222(5) 0.7029(2) 0.3603(2) 0.0143(10) Uani 0.50 1 d PDU A -1
H1 H 0.518(2) 0.704(5) 0.288(5) 0.017 Uiso 0.25 1 d PD B -1
C3 C 0.5566(4) 0.8345(3) 0.3865(3) 0.0201(7) Uani 0.50 1 d PDU A -1
H3A H 0.6663 0.8479 0.3787 0.024 Uiso 0.50 1 calc PR A -1
H3B H 0.5294 0.8510 0.4660 0.024 Uiso 0.50 1 calc PR A -1
C4 C 0.4745(5) 0.9263(3) 0.3117(3) 0.0215(12) Uani 0.50 1 d PU A -1
H4A H 0.5100 1.0065 0.3339 0.026 Uiso 0.50 1 d PR A -1
H4B H 0.3707 0.9224 0.3339 0.026 Uiso 0.50 1 d PR A -1

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 0.01436(10) 0.01625(11) 0.02438(13) 0.000 0.000 0.000
C1 0.0162(19) 0.019(3) 0.026(2) 0.000(2) -0.0040(16) 0.0026(19)
C2 0.018(2) 0.026(3) 0.022(2) 0.002(2) -0.0022(16) -0.003(2)
N1 0.010(3) 0.0147(10) 0.0184(12) -0.0002(9) 0.0013(10) -0.0010(10)
C3 0.0204(13) 0.0183(15) 0.0217(17) -0.0049(13) -0.0002(13) -0.0003(12)
C4 0.023(4) 0.0136(12) 0.0281(16) -0.0037(12) -0.0008(13) 0.0026(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
C1 N1 1.478(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.476(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N1 C3 1.490(4) . ?
N1 H1 0.86(6) . ?
C3 C4 1.519(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?

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 N1 C1 110.1(3) . . ?
C2 N1 C3 111.9(3) . . ?
C1 N1 C3 111.6(3) . . ?
C2 N1 H1 110(2) . . ?
C1 N1 H1 111(2) . . ?
C3 N1 H1 102(4) . . ?
N1 C3 C4 113.9(3) . . ?
N1 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
N1 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 H4A 105.9 . . ?
C3 C4 H4B 105.8 . . ?
H4A C4 H4B 106.2 . . ?

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
C2 N1 C3 C4 -78.8(4) . . . . ?
C1 N1 C3 C4 157.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N1 0.86(6) 1.79(6) 2.648(6) 171(2) 3_655

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.546
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.096