# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Pamela Dean'
_publ_contact_author_email       PAMELA.DEAN@SCI.MONASH.EDU.AU

_publ_section_title              
;
The effect of alkyl chain length
in a series of novel N-alkyl-3-benzylimidazolium iodide salts
;
loop_
_publ_author_name
'Pamela Dean'
'Maria Forsyth'
'Jacob J. Golding'
'Douglas MacFarlane'
'Jennifer M. Pringle'
;
B.W.Skelton
;
'Allan H. White'

#===============================================================================

data_jak255
_database_code_depnum_ccdc_archive 'CCDC 711758'

_audit_creation_date             2008-06-15T18:48:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C13 H17 I N2'
_chemical_formula_moiety         'C13 H17 N2, I'
_chemical_formula_weight         328.19

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P_1_21/c_1
_symmetry_space_group_name_Hall  -p_2ybc

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                   18.041(2)
_cell_length_b                   11.0850(10)
_cell_length_c                   14.137(2)
_cell_angle_alpha                90.000
_cell_angle_beta                 105.013(2)
_cell_angle_gamma                90.000
_cell_volume                     2730.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4058
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      29.93

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_size_max          .63
_exptl_crystal_size_mid          .5
_exptl_crystal_size_min          .12
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.323

_diffrn_measurement_device_type  
;
Bruker SMART CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS; Sheldrick, 1996
;
_exptl_absorpt_correction_T_min  .77
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  .027
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_number            7865
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_full        28.5
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.983
_reflns_number_total             7865
_reflns_number_gt                6013
_reflns_threshold_expression     I>2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'xtal ADDREF SORTRF'
_computing_structure_solution    xtal
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0485P)²+1.0111P] 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_number_reflns         7865
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.482
_refine_diff_density_min         -1.155
_refine_diff_density_rms         0.113

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.620038(11) 0.281890(19) 0.187622(15) 0.03074(7) Uani 1 1 d . . .
I2 I 0.933597(13) 0.85184(2) 0.187446(17) 0.04181(8) Uani 1 1 d . . .
C11 C 0.71394(17) 0.3540(3) 0.4828(2) 0.0295(6) Uani 1 1 d . . .
H11A H 0.7107 0.3176 0.5455 0.035 Uiso 0.797(5) 1 calc PR A 1
H11B H 0.6772 0.3108 0.4292 0.035 Uiso 0.797(5) 1 calc PR A 1
H11C H 0.6808 0.3072 0.5153 0.035 Uiso 0.203(5) 1 d PR A 2
H11D H 0.7035 0.325 0.4143 0.035 Uiso 0.203(5) 1 d PR A 2
C111 C 0.69084(16) 0.4851(3) 0.4811(2) 0.0242(6) Uani 1 1 d . A .
C112 C 0.74262(18) 0.5791(3) 0.4923(2) 0.0304(6) Uani 1 1 d . . .
H112 H 0.7957 0.562 0.5027 0.037 Uiso 1 1 calc R A .
C113 C 0.7181(2) 0.6987(3) 0.4885(3) 0.0381(8) Uani 1 1 d . A .
H113 H 0.7542 0.7626 0.4962 0.046 Uiso 1 1 calc R . .
C114 C 0.6410(2) 0.7234(3) 0.4736(3) 0.0404(8) Uani 1 1 d . . .
H114 H 0.6238 0.8047 0.47 0.049 Uiso 1 1 calc R A .
C115 C 0.5887(2) 0.6305(3) 0.4639(3) 0.0401(8) Uani 1 1 d . A .
H115 H 0.5358 0.6481 0.4545 0.048 Uiso 1 1 calc R . .
C116 C 0.61300(17) 0.5122(3) 0.4678(2) 0.0323(7) Uani 1 1 d . . .
H116 H 0.5767 0.4487 0.4615 0.039 Uiso 1 1 calc R A .
N11 N 0.79135(18) 0.3370(3) 0.4716(2) 0.0270(8) Uani 0.797(5) 1 d PD A 1
C12 C 0.8555(2) 0.3132(3) 0.5425(3) 0.0265(9) Uani 0.797(5) 1 d PD A 1
C121 C 0.8615(3) 0.3056(4) 0.6477(3) 0.0342(10) Uani 0.797(5) 1 d PD A 1
H12A H 0.9023 0.2487 0.6782 0.051 Uiso 0.797(5) 1 calc PR A 1
H12B H 0.8126 0.2775 0.6578 0.051 Uiso 0.797(5) 1 calc PR A 1
H12C H 0.8736 0.3854 0.6775 0.051 Uiso 0.797(5) 1 calc PR A 1
N13 N 0.91256(17) 0.2998(3) 0.4993(2) 0.0264(8) Uani 0.797(5) 1 d PD A 1
C14 C 0.8846(3) 0.3174(4) 0.3991(3) 0.0291(9) Uani 0.797(5) 1 d PD A 1
H14 H 0.9134 0.3138 0.3516 0.035 Uiso 0.797(5) 1 calc PR A 1
C15 C 0.8090(3) 0.3408(4) 0.3819(3) 0.0316(9) Uani 0.797(5) 1 d PD A 1
H15 H 0.7744 0.3568 0.32 0.038 Uiso 0.797(5) 1 calc PR A 1
C131 C 0.99174(18) 0.2652(3) 0.5470(2) 0.0332(7) Uani 1 1 d . . .
H13A H 1.0131 0.2213 0.499 0.04 Uiso 0.797(5) 1 calc PR A 1
H13B H 0.9913 0.2088 0.6012 0.04 Uiso 0.797(5) 1 calc PR A 1
H13F H 0.9896 0.253 0.4769 0.04 Uiso 0.203(5) 1 d PR A 2
H13G H 1.0113 0.1903 0.583 0.04 Uiso 0.203(5) 1 d PR A 2
C132 C 1.04406(19) 0.3695(4) 0.5874(3) 0.0413(8) Uani 1 1 d . A .
H13C H 1.0463 0.4247 0.5341 0.062 Uiso 1 1 calc R . .
H13D H 1.0957 0.339 0.6182 0.062 Uiso 1 1 calc R . .
H13E H 1.0242 0.4126 0.6363 0.062 Uiso 1 1 calc R . .
N31 N 0.7924(6) 0.3280(11) 0.5309(8) 0.023(3) Uiso 0.203(5) 1 d PD A 2
C32 C 0.8503(7) 0.3127(14) 0.4878(9) 0.028(3) Uiso 0.203(5) 1 d PD A 2
C321 C 0.8443(13) 0.3193(16) 0.3833(10) 0.027(4) Uiso 0.203(5) 1 d PD A 2
H32A H 0.8286 0.4008 0.3595 0.04 Uiso 0.203(5) 1 calc PR A 2
H32B H 0.8061 0.2609 0.3485 0.04 Uiso 0.203(5) 1 calc PR A 2
H32C H 0.8943 0.3006 0.3714 0.04 Uiso 0.203(5) 1 calc PR A 2
N33 N 0.9130(6) 0.2938(11) 0.5585(9) 0.025(3) Uiso 0.203(5) 1 d PD A 2
C34 C 0.8960(9) 0.2946(17) 0.6494(11) 0.033(4) Uiso 0.203(5) 1 d PD A 2
H34 H 0.9312 0.2827 0.7115 0.039 Uiso 0.203(5) 1 calc PR A 2
C35 C 0.8198(8) 0.3153(14) 0.6321(9) 0.023(3) Uiso 0.203(5) 1 d PD A 2
H35 H 0.7908 0.3203 0.6793 0.028 Uiso 0.203(5) 1 calc PR A 2
C21 C 0.7426(2) 0.9674(3) 0.2600(3) 0.0384(8) Uani 1 1 d . . .
H21A H 0.7853 0.9756 0.2284 0.046 Uiso 0.5 1 calc PR B 1
H21B H 0.7039 1.0301 0.2326 0.046 Uiso 0.5 1 calc PR B 1
H21C H 0.7341 1.0472 0.2276 0.046 Uiso 0.5 1 d PR B 2
H21D H 0.7817 0.9242 0.2351 0.046 Uiso 0.5 1 d PR B 2
C211 C 0.77231(19) 0.9850(3) 0.3690(3) 0.0336(7) Uani 1 1 d . C .
C212 C 0.7246(2) 1.0285(3) 0.4240(3) 0.0407(8) Uani 1 1 d . . .
H212 H 0.6734 1.0512 0.3922 0.049 Uiso 1 1 calc R C .
C213 C 0.7507(3) 1.0392(3) 0.5254(3) 0.0498(10) Uani 1 1 d . C .
H213 H 0.7173 1.0682 0.5623 0.06 Uiso 1 1 calc R . .
C214 C 0.8240(3) 1.0081(3) 0.5711(3) 0.0536(11) Uani 1 1 d . . .
H214 H 0.8414 1.0131 0.6405 0.064 Uiso 1 1 calc R C .
C215 C 0.8737(3) 0.9689(4) 0.5170(3) 0.0512(10) Uani 1 1 d . C .
H215 H 0.9256 0.9506 0.549 0.061 Uiso 1 1 calc R . .
C216 C 0.8475(2) 0.9565(3) 0.4163(3) 0.0432(9) Uani 1 1 d . . .
H216 H 0.8813 0.9284 0.3795 0.052 Uiso 1 1 calc R C .
N21 N 0.7053(3) 0.8391(5) 0.2377(4) 0.0217(10) Uani 0.5 1 d PD C 1
C22 C 0.6307(4) 0.8134(6) 0.2278(4) 0.0220(11) Uani 0.5 1 d PD C 1
C221 C 0.5683(5) 0.9017(8) 0.2230(7) 0.0329(18) Uani 0.5 1 d PD C 1
H22A H 0.5251 0.883 0.1668 0.049 Uiso 0.5 1 calc PR C 1
H22B H 0.5871 0.9832 0.2156 0.049 Uiso 0.5 1 calc PR C 1
H22C H 0.5513 0.8974 0.2834 0.049 Uiso 0.5 1 calc PR C 1
N23 N 0.6230(3) 0.6934(5) 0.2193(4) 0.0207(10) Uani 0.5 1 d PD C 1
C24 C 0.6933(4) 0.6419(6) 0.2242(5) 0.0238(12) Uani 0.5 1 d PD C 1
H24 H 0.7039 0.5582 0.2215 0.029 Uiso 0.5 1 calc PR C 1
C25 C 0.7440(7) 0.7328(11) 0.2334(15) 0.026(3) Uani 0.5 1 d PD C 1
H25 H 0.797 0.7252 0.2363 0.031 Uiso 0.5 1 calc PR C 1
C231 C 0.5562(3) 0.6274(3) 0.2054(3) 0.0467(9) Uani 1 1 d . . .
H23A H 0.5237 0.6673 0.2428 0.056 Uiso 0.5 1 calc PR C 1
H23B H 0.57 0.5469 0.2352 0.056 Uiso 0.5 1 calc PR C 1
H23F H 0.5935 0.5605 0.224 0.056 Uiso 0.5 1 d PR C 2
H23G H 0.523 0.6275 0.2512 0.056 Uiso 0.5 1 d PR C 2
C232 C 0.5091(2) 0.6088(4) 0.1051(3) 0.0557(11) Uani 1 1 d . C .
H23C H 0.4922 0.6871 0.075 0.084 Uiso 1 1 calc R . .
H23D H 0.4642 0.5598 0.1065 0.084 Uiso 1 1 calc R . .
H23E H 0.5395 0.5671 0.0668 0.084 Uiso 1 1 calc R . .
N41 N 0.6742(4) 0.9021(6) 0.2355(5) 0.0418(14) Uani 0.5 1 d PD C 2
C42 C 0.6720(6) 0.7846(7) 0.2298(5) 0.0397(18) Uani 0.5 1 d PD C 2
C421 C 0.7384(9) 0.7022(13) 0.2405(17) 0.045(5) Uani 0.5 1 d PD C 2
H42A H 0.7838 0.7489 0.2372 0.067 Uiso 0.5 1 calc PR C 2
H42B H 0.727 0.6426 0.1875 0.067 Uiso 0.5 1 calc PR C 2
H42C H 0.7484 0.6607 0.3037 0.067 Uiso 0.5 1 calc PR C 2
N43 N 0.5992(4) 0.7476(7) 0.2126(5) 0.0410(16) Uani 0.5 1 d PD C 2
C44 C 0.5529(5) 0.8500(7) 0.2108(7) 0.039(2) Uani 0.5 1 d PD C 2
H44 H 0.4989 0.8513 0.2023 0.047 Uiso 0.5 1 calc PR C 2
C45 C 0.5995(5) 0.9441(7) 0.2232(7) 0.0422(19) Uani 0.5 1 d PD C 2
H45 H 0.5847 1.0263 0.2237 0.051 Uiso 0.5 1 calc PR C 2


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
C11 N31 1.432(11) . ?
C11 N11 1.458(4) . ?
C11 C111 1.510(4) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C11 H11C 0.99 . ?
C11 H11D 0.99 . ?
C111 C112 1.381(4) . ?
C111 C116 1.400(4) . ?
C112 C113 1.394(5) . ?
C112 H112 0.95 . ?
C113 C114 1.379(5) . ?
C113 H113 0.95 . ?
C114 C115 1.379(5) . ?
C114 H114 0.95 . ?
C115 C116 1.379(5) . ?
C115 H115 0.95 . ?
C116 H116 0.95 . ?
N11 C12 1.347(5) . ?
N11 C15 1.387(5) . ?
C12 N13 1.335(4) . ?
C12 C121 1.465(5) . ?
C121 H12A 0.98 . ?
C121 H12B 0.98 . ?
C121 H12C 0.98 . ?
N13 C14 1.388(5) . ?
N13 C131 1.464(4) . ?
C14 C15 1.348(5) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C131 N33 1.505(11) . ?
C131 C132 1.509(5) . ?
C131 H13A 0.99 . ?
C131 H13B 0.99 . ?
C131 H13F 0.99 . ?
C131 H13G 0.99 . ?
C132 H13C 0.98 . ?
C132 H13D 0.98 . ?
C132 H13E 0.98 . ?
N31 C32 1.349(13) . ?
N31 C35 1.395(14) . ?
C32 N33 1.317(14) . ?
C32 C321 1.456(14) . ?
C321 H32A 0.98 . ?
C321 H32B 0.98 . ?
C321 H32C 0.98 . ?
N33 C34 1.397(15) . ?
C34 C35 1.353(16) . ?
C34 H34 0.95 . ?
C35 H35 0.95 . ?
C21 N41 1.394(7) . ?
C21 C211 1.508(5) . ?
C21 N21 1.570(7) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C21 H21C 0.99 . ?
C21 H21D 0.99 . ?
C211 C216 1.385(5) . ?
C211 C212 1.388(4) . ?
C212 C213 1.392(6) . ?
C212 H212 0.95 . ?
C213 C214 1.357(6) . ?
C213 H213 0.95 . ?
C214 C215 1.392(6) . ?
C214 H214 0.95 . ?
C215 C216 1.385(6) . ?
C215 H215 0.95 . ?
C216 H216 0.95 . ?
N21 C22 1.346(7) . ?
N21 C25 1.378(13) . ?
C22 N23 1.340(7) . ?
C22 C221 1.480(9) . ?
C221 H22A 0.98 . ?
C221 H22B 0.98 . ?
C221 H22C 0.98 . ?
N23 C24 1.376(7) . ?
N23 C231 1.380(6) . ?
C24 C25 1.345(12) . ?
C24 H24 0.95 . ?
C25 H25 0.95 . ?
C231 C232 1.466(6) . ?
C231 N43 1.532(8) . ?
C231 H23A 0.99 . ?
C231 H23B 0.99 . ?
C231 H23F 0.99 . ?
C231 H23G 0.99 . ?
C232 H23C 0.98 . ?
C232 H23D 0.98 . ?
C232 H23E 0.98 . ?
N41 C42 1.305(9) . ?
N41 C45 1.393(9) . ?
C42 N43 1.335(10) . ?
C42 C421 1.483(14) . ?
C421 H42A 0.98 . ?
C421 H42B 0.98 . ?
C421 H42C 0.98 . ?
N43 C44 1.406(10) . ?
C44 C45 1.324(10) . ?
C44 H44 0.95 . ?
C45 H45 0.95 . ?

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
N11 C11 C111 113.0(3) . . ?
N11 C11 H11A 109 . . ?
C111 C11 H11A 109 . . ?
N11 C11 H11B 109 . . ?
C111 C11 H11B 109 . . ?
H11A C11 H11B 107.8 . . ?
N31 C11 H11C 108.3 . . ?
C111 C11 H11C 108.3 . . ?
N31 C11 H11D 108.3 . . ?
C111 C11 H11D 108.3 . . ?
H11C C11 H11D 107.4 . . ?
C112 C111 C116 118.6(3) . . ?
C112 C111 C11 123.3(3) . . ?
C116 C111 C11 118.1(3) . . ?
C111 C112 C113 121.0(3) . . ?
C111 C112 H112 119.5 . . ?
C113 C112 H112 119.5 . . ?
C114 C113 C112 119.5(3) . . ?
C114 C113 H113 120.2 . . ?
C112 C113 H113 120.2 . . ?
C113 C114 C115 120.2(3) . . ?
C113 C114 H114 119.9 . . ?
C115 C114 H114 119.9 . . ?
C114 C115 C116 120.3(3) . . ?
C114 C115 H115 119.9 . . ?
C116 C115 H115 119.9 . . ?
C115 C116 C111 120.4(3) . . ?
C115 C116 H116 119.8 . . ?
C111 C116 H116 119.8 . . ?
C12 N11 C15 109.3(3) . . ?
C12 N11 C11 127.5(3) . . ?
C15 N11 C11 123.2(3) . . ?
N13 C12 N11 107.3(3) . . ?
N13 C12 C121 126.6(4) . . ?
N11 C12 C121 126.1(4) . . ?
C12 N13 C14 109.4(3) . . ?
C12 N13 C131 126.4(3) . . ?
C14 N13 C131 124.0(3) . . ?
C15 C14 N13 107.1(3) . . ?
C15 C14 H14 126.4 . . ?
N13 C14 H14 126.4 . . ?
C14 C15 N11 106.9(4) . . ?
C14 C15 H15 126.6 . . ?
N11 C15 H15 126.6 . . ?
N13 C131 C132 114.5(3) . . ?
N33 C131 C132 108.2(5) . . ?
N13 C131 H13A 108.6 . . ?
C132 C131 H13A 108.6 . . ?
N13 C131 H13B 108.6 . . ?
C132 C131 H13B 108.6 . . ?
H13A C131 H13B 107.6 . . ?
N33 C131 H13F 110.1 . . ?
C132 C131 H13F 110.1 . . ?
N13 C131 H13G 129.2 . . ?
N33 C131 H13G 110.1 . . ?
C132 C131 H13G 110.1 . . ?
H13F C131 H13G 108.4 . . ?
C131 C132 H13C 109.5 . . ?
C131 C132 H13D 109.5 . . ?
H13C C132 H13D 109.5 . . ?
C131 C132 H13E 109.5 . . ?
H13C C132 H13E 109.5 . . ?
H13D C132 H13E 109.5 . . ?
C32 N31 C35 109.9(10) . . ?
C32 N31 C11 126.6(10) . . ?
C35 N31 C11 123.5(10) . . ?
N33 C32 N31 106.9(10) . . ?
N33 C32 C321 127.0(14) . . ?
N31 C32 C321 126.1(13) . . ?
C32 C321 H32A 109.5 . . ?
C32 C321 H32B 109.5 . . ?
H32A C321 H32B 109.5 . . ?
C32 C321 H32C 109.5 . . ?
H32A C321 H32C 109.5 . . ?
H32B C321 H32C 109.5 . . ?
C32 N33 C34 110.3(11) . . ?
C32 N33 C131 126.9(10) . . ?
C34 N33 C131 122.6(10) . . ?
C35 C34 N33 106.8(13) . . ?
C35 C34 H34 126.6 . . ?
N33 C34 H34 126.6 . . ?
C34 C35 N31 106.0(12) . . ?
C34 C35 H35 127 . . ?
N31 C35 H35 127 . . ?
N41 C21 C211 112.2(3) . . ?
C211 C21 N21 110.1(3) . . ?
C211 C21 H21A 109.6 . . ?
N21 C21 H21A 109.6 . . ?
C211 C21 H21B 109.6 . . ?
N21 C21 H21B 109.6 . . ?
H21A C21 H21B 108.2 . . ?
N41 C21 H21C 109.2 . . ?
C211 C21 H21C 109.2 . . ?
N41 C21 H21D 109.1 . . ?
C211 C21 H21D 109.1 . . ?
H21C C21 H21D 107.9 . . ?
C216 C211 C212 118.8(4) . . ?
C216 C211 C21 120.6(3) . . ?
C212 C211 C21 120.7(3) . . ?
C211 C212 C213 120.8(4) . . ?
C211 C212 H212 119.6 . . ?
C213 C212 H212 119.6 . . ?
C214 C213 C212 119.9(3) . . ?
C214 C213 H213 120.1 . . ?
C212 C213 H213 120.1 . . ?
C213 C214 C215 120.2(4) . . ?
C213 C214 H214 119.9 . . ?
C215 C214 H214 119.9 . . ?
C216 C215 C214 120.0(4) . . ?
C216 C215 H215 120 . . ?
C214 C215 H215 120 . . ?
C215 C216 C211 120.2(3) . . ?
C215 C216 H216 119.9 . . ?
C211 C216 H216 119.9 . . ?
C22 N21 C25 108.6(7) . . ?
C22 N21 C21 125.2(5) . . ?
C25 N21 C21 126.0(7) . . ?
N23 C22 N21 107.3(5) . . ?
N23 C22 C221 126.3(6) . . ?
N21 C22 C221 126.4(6) . . ?
C22 N23 C24 109.6(5) . . ?
C22 N23 C231 127.3(5) . . ?
C24 N23 C231 123.1(5) . . ?
C25 C24 N23 106.8(7) . . ?
C25 C24 H24 126.6 . . ?
N23 C24 H24 126.6 . . ?
C24 C25 N21 107.8(9) . . ?
C24 C25 H25 126.1 . . ?
N21 C25 H25 126.1 . . ?
N23 C231 C232 118.6(4) . . ?
C232 C231 N43 110.1(4) . . ?
N23 C231 H23A 107.7 . . ?
C232 C231 H23A 107.7 . . ?
N23 C231 H23B 107.7 . . ?
C232 C231 H23B 107.7 . . ?
H23A C231 H23B 107.1 . . ?
C232 C231 H23F 109.6 . . ?
N43 C231 H23F 109.6 . . ?
N23 C231 H23G 124 . . ?
C232 C231 H23G 109.7 . . ?
N43 C231 H23G 109.6 . . ?
H23F C231 H23G 108.2 . . ?
C231 C232 H23C 109.5 . . ?
C231 C232 H23D 109.5 . . ?
H23C C232 H23D 109.5 . . ?
C231 C232 H23E 109.5 . . ?
H23C C232 H23E 109.5 . . ?
H23D C232 H23E 109.5 . . ?
C42 N41 C45 108.2(7) . . ?
C42 N41 C21 123.0(7) . . ?
C45 N41 C21 128.5(6) . . ?
N41 C42 N43 109.3(7) . . ?
N41 C42 C421 126.6(11) . . ?
N43 C42 C421 124.1(9) . . ?
C42 C421 H42A 109.5 . . ?
C42 C421 H42B 109.5 . . ?
H42A C421 H42B 109.5 . . ?
C42 C421 H42C 109.5 . . ?
H42A C421 H42C 109.5 . . ?
H42B C421 H42C 109.5 . . ?
C42 N43 C44 107.9(7) . . ?
C42 N43 C231 137.4(7) . . ?
C44 N43 C231 114.3(6) . . ?
C45 C44 N43 106.2(8) . . ?
C45 C44 H44 126.9 . . ?
N43 C44 H44 126.9 . . ?
C44 C45 N41 108.3(7) . . ?
C44 C45 H45 125.8 . . ?
N41 C45 H45 125.8 . . ?

#===============================================================================
data_jak249
_database_code_depnum_ccdc_archive 'CCDC 711759'

_audit_creation_date             2008-06-22T10:16:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C14 H19 I N2'
_chemical_formula_moiety         'C14 H19 N2, I'
_chemical_formula_weight         342.21

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P_-1
_symmetry_space_group_name_Hall  -p_1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.232(2)
_cell_length_b                   9.316(2)
_cell_length_c                   10.209(3)
_cell_angle_alpha                86.158(5)
_cell_angle_beta                 84.638(5)
_cell_angle_gamma                64.690(4)
_cell_volume                     704.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1688
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      28.7

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_size_max          .43
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .35
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.255
_diffrn_measurement_device_type  
;
Bruker SMART CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS; Sheldrick, 1996
;
_exptl_absorpt_correction_T_min  .90
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  .015
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_number            2190
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2
_diffrn_reflns_theta_max         28.83
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.705
_diffrn_measured_fraction_theta_max 0.594
_reflns_number_total             2190
_reflns_number_gt                2107
_reflns_threshold_expression     I>2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_reduction        'xtal ADDREF SORTRF'
_computing_structure_solution    xtal
_computing_molecular_graphics    xtal
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0383P)²+0.4899P] 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_number_reflns         2190
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0638
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.775
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.087

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'

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
I I 0.10248(3) 0.69266(3) 0.206737(15) 0.02265(12) Uani 1 1 d . . .
N1 N 0.2443(4) 0.8027(4) 0.7565(2) 0.0167(8) Uani 1 1 d . . .
C1 C 0.2772(5) 0.8693(5) 0.8735(3) 0.0178(9) Uani 1 1 d . . .
H1A H 0.2791 0.7994 0.9514 0.021 Uiso 1 1 calc R . .
H1B H 0.1771 0.9751 0.8898 0.021 Uiso 1 1 calc R . .
C11 C 0.4527(4) 0.8849(5) 0.8560(2) 0.0164(9) Uani 1 1 d . . .
C12 C 0.4519(5) 1.0309(5) 0.8243(3) 0.0215(10) Uani 1 1 d . . .
H12 H 0.3415 1.121 0.8115 0.026 Uiso 1 1 calc R . .
C13 C 0.6133(5) 1.0461(5) 0.8112(3) 0.0280(11) Uani 1 1 d . . .
H13 H 0.6134 1.1466 0.7882 0.034 Uiso 1 1 calc R . .
C14 C 0.7713(5) 0.9177(5) 0.8312(3) 0.0295(11) Uani 1 1 d . . .
H14 H 0.8811 0.9291 0.8233 0.035 Uiso 1 1 calc R . .
C15 C 0.7725(5) 0.7713(6) 0.8628(3) 0.0325(11) Uani 1 1 d . . .
H15 H 0.883 0.682 0.8769 0.039 Uiso 1 1 calc R . .
C16 C 0.6127(5) 0.7544(5) 0.8740(3) 0.0269(11) Uani 1 1 d . . .
H16 H 0.6135 0.653 0.8941 0.032 Uiso 1 1 calc R . .
C2 C 0.2475(4) 0.6608(5) 0.7463(3) 0.0171(9) Uani 1 1 d . . .
C21 C 0.2967(5) 0.5304(5) 0.8474(3) 0.0255(10) Uani 1 1 d . . .
H21A H 0.428 0.4712 0.8442 0.038 Uiso 1 1 calc R . .
H21B H 0.2425 0.4587 0.8302 0.038 Uiso 1 1 calc R . .
H21C H 0.252 0.575 0.9347 0.038 Uiso 1 1 calc R . .
N3 N 0.2039(4) 0.6516(4) 0.6251(2) 0.0178(8) Uani 1 1 d . . .
C31 C 0.1845(4) 0.5169(5) 0.5729(3) 0.0191(10) Uani 1 1 d . . .
H31A H 0.1086 0.5554 0.497 0.023 Uiso 1 1 calc R . .
H31B H 0.1207 0.4758 0.6416 0.023 Uiso 1 1 calc R . .
C32 C 0.3587(5) 0.3840(5) 0.5299(3) 0.0236(11) Uani 1 1 d . . .
H32A H 0.4389 0.3485 0.6033 0.028 Uiso 1 1 calc R . .
H32B H 0.4189 0.4209 0.4556 0.028 Uiso 1 1 calc R . .
C33 C 0.3254(6) 0.2473(5) 0.4878(3) 0.0306(11) Uani 1 1 d . . .
H33A H 0.2584 0.2159 0.5596 0.046 Uiso 1 1 calc R . .
H33B H 0.4409 0.1572 0.4665 0.046 Uiso 1 1 calc R . .
H33C H 0.2552 0.2801 0.41 0.046 Uiso 1 1 calc R . .
C4 C 0.1727(4) 0.7925(5) 0.5576(3) 0.0203(10) Uani 1 1 d . . .
H4 H 0.1399 0.818 0.4694 0.024 Uiso 1 1 calc R . .
C5 C 0.1972(4) 0.8878(5) 0.6397(3) 0.0209(10) Uani 1 1 d . . .
H5 H 0.1845 0.9932 0.6207 0.025 Uiso 1 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
N1 C2 1.321(5) . ?
N1 C5 1.378(3) . ?
N1 C1 1.479(4) . ?
C1 C11 1.507(4) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C11 C12 1.374(5) . ?
C11 C16 1.376(5) . ?
C12 C13 1.389(4) . ?
C12 H12 0.95 . ?
C13 C14 1.361(6) . ?
C13 H13 0.95 . ?
C14 C15 1.376(6) . ?
C14 H14 0.95 . ?
C15 C16 1.384(5) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C2 N3 1.338(3) . ?
C2 C21 1.481(4) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
N3 C4 1.374(4) . ?
N3 C31 1.471(4) . ?
C31 C32 1.490(5) . ?
C31 H31A 0.99 . ?
C31 H31B 0.99 . ?
C32 C33 1.508(5) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C33 H33C 0.98 . ?
C4 C5 1.348(5) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?

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 C5 109.4(2) . . ?
C2 N1 C1 127.6(2) . . ?
C5 N1 C1 122.9(3) . . ?
N1 C1 C11 111.9(2) . . ?
N1 C1 H1A 109.2 . . ?
C11 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C11 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C12 C11 C16 120.2(3) . . ?
C12 C11 C1 119.6(3) . . ?
C16 C11 C1 120.2(3) . . ?
C11 C12 C13 119.7(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15 120 . . ?
C16 C15 H15 120 . . ?
C11 C16 C15 119.7(4) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N1 C2 N3 108.0(3) . . ?
N1 C2 C21 127.1(3) . . ?
N3 C2 C21 124.9(3) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 N3 C4 108.7(3) . . ?
C2 N3 C31 126.4(3) . . ?
C4 N3 C31 124.9(2) . . ?
N3 C31 C32 114.0(2) . . ?
N3 C31 H31A 108.8 . . ?
C32 C31 H31A 108.8 . . ?
N3 C31 H31B 108.8 . . ?
C32 C31 H31B 108.8 . . ?
H31A C31 H31B 107.7 . . ?
C31 C32 C33 109.9(3) . . ?
C31 C32 H32A 109.7 . . ?
C33 C32 H32A 109.7 . . ?
C31 C32 H32B 109.7 . . ?
C33 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C5 C4 N3 107.3(2) . . ?
C5 C4 H4 126.3 . . ?
N3 C4 H4 126.3 . . ?
C4 C5 N1 106.6(3) . . ?
C4 C5 H5 126.7 . . ?
N1 C5 H5 126.7 . . ?

# Attachment 'global1.cif'

data_jak216
_database_code_depnum_ccdc_archive 'CCDC 720677'

_audit_creation_date             2009-02-11T16:28:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C12 H15 I N2'
_chemical_formula_moiety         'C12 H15 N2, I'

_chemical_formula_weight         314.16

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  -p_2ac_2ab

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

_cell_length_a                   12.5337(1)
_cell_length_b                   11.6484(1)
_cell_length_c                   17.1447(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2503.08(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    72687
_cell_measurement_theta_min      3.5565
_cell_measurement_theta_max      43.4336

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5078
_exptl_crystal_size_mid          0.2625
_exptl_crystal_size_min          0.1746
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.53
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_correction_T_min  0.468
_exptl_absorpt_correction_T_max  0.704

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      0.0421318353
_diffrn_orient_matrix_ub_12      -0.0370420462
_diffrn_orient_matrix_ub_13      -0.0123698059
_diffrn_orient_matrix_ub_21      -0.0430019864
_diffrn_orient_matrix_ub_22      -0.0394527492
_diffrn_orient_matrix_ub_23      -0.0044687756
_diffrn_orient_matrix_ub_31      -0.0082954707
_diffrn_orient_matrix_ub_32      0.0162104802
_diffrn_orient_matrix_ub_33      -0.0391696902
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_number            169801
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         43.64
_diffrn_reflns_theta_full        43.64
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  
;
Oxford Diffraction Gemini diffractometer
;
_diffrn_measurement_method       'ω scans'
_reflns_number_total             9534
_reflns_number_gt                7484
_reflns_threshold_expression     I>2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    OrtepII
_computing_publication_material  WinGX

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0255P)²+0.2191P] 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_number_reflns         9534
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0489
_refine_ls_wR_factor_gt          0.0474
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.64
_refine_diff_density_min         -1.45
_refine_diff_density_rms         0.113

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.618559(4) 0.466917(4) 0.653683(3) 0.014790(10) Uani 1 1 d . . .
N1 N 0.30038(5) 0.22443(5) 0.58013(3) 0.01236(9) Uani 1 1 d . . .
C1 C 0.38492(6) 0.28927(6) 0.53948(4) 0.01440(10) Uani 1 1 d . . .
H1A H 0.4252 0.3354 0.578 0.017 Uiso 1 1 calc R . .
H1B H 0.3517 0.3428 0.5018 0.017 Uiso 1 1 calc R . .
C11 C 0.46092(5) 0.21119(6) 0.49680(4) 0.01270(10) Uani 1 1 d . . .
C12 C 0.54385(6) 0.15706(6) 0.53650(4) 0.01501(11) Uani 1 1 d . . .
H12 H 0.5514 0.1678 0.5912 0.018 Uiso 1 1 calc R . .
C13 C 0.61574(6) 0.08738(7) 0.49665(5) 0.01730(12) Uani 1 1 d . . .
H13 H 0.6719 0.0503 0.524 0.021 Uiso 1 1 calc R . .
C14 C 0.60482(6) 0.07228(7) 0.41621(5) 0.01844(13) Uani 1 1 d . . .
H14 H 0.6543 0.0256 0.3887 0.022 Uiso 1 1 calc R . .
C15 C 0.52193(7) 0.12525(7) 0.37635(4) 0.01842(13) Uani 1 1 d . . .
H15 H 0.5143 0.1144 0.3217 0.022 Uiso 1 1 calc R . .
C16 C 0.44996(6) 0.19443(7) 0.41669(4) 0.01584(11) Uani 1 1 d . . .
H16 H 0.3931 0.2304 0.3894 0.019 Uiso 1 1 calc R . .
C2 C 0.28101(5) 0.22230(6) 0.65717(4) 0.01272(10) Uani 1 1 d . . .
C21 C 0.34268(6) 0.27780(7) 0.72045(4) 0.01852(13) Uani 1 1 d . . .
H21A H 0.2966 0.3317 0.7486 0.028 Uiso 1 1 calc R . .
H21B H 0.4033 0.3194 0.698 0.028 Uiso 1 1 calc R . .
H21C H 0.3689 0.219 0.7566 0.028 Uiso 1 1 calc R . .
N3 N 0.19349(5) 0.15823(6) 0.66845(4) 0.01367(9) Uani 1 1 d . . .
C31 C 0.14221(6) 0.13837(8) 0.74421(5) 0.01865(13) Uani 1 1 d . . .
H31A H 0.1901 0.0937 0.7777 0.028 Uiso 1 1 calc R . .
H31B H 0.0756 0.0959 0.7365 0.028 Uiso 1 1 calc R . .
H31C H 0.1267 0.2123 0.7691 0.028 Uiso 1 1 calc R . .
C4 C 0.15632(6) 0.11927(6) 0.59734(4) 0.01497(11) Uani 1 1 d . . .
H4 H 0.0954 0.0724 0.5889 0.018 Uiso 1 1 calc R . .
C5 C 0.22327(5) 0.16050(6) 0.54205(4) 0.01437(10) Uani 1 1 d . . .
H5 H 0.2183 0.1479 0.4874 0.017 Uiso 1 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
N1 C2 1.3432(9) . ?
N1 C5 1.3838(9) . ?
N1 C1 1.4761(9) . ?
C1 C11 1.5066(10) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C11 C12 1.3933(10) . ?
C11 C16 1.3941(10) . ?
C12 C13 1.3920(11) . ?
C12 H12 0.95 . ?
C13 C14 1.3970(12) . ?
C13 H13 0.95 . ?
C14 C15 1.3882(12) . ?
C14 H14 0.95 . ?
C15 C16 1.3934(11) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C2 N3 1.3409(9) . ?
C2 C21 1.4805(10) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
N3 C4 1.3818(10) . ?
N3 C31 1.4675(10) . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C4 C5 1.3540(11) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?

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 C5 109.14(6) . . ?
C2 N1 C1 127.12(6) . . ?
C5 N1 C1 123.64(6) . . ?
N1 C1 C11 111.98(6) . . ?
N1 C1 H1A 109.2 . . ?
C11 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C11 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C12 C11 C16 119.43(7) . . ?
C12 C11 C1 120.51(6) . . ?
C16 C11 C1 120.05(6) . . ?
C13 C12 C11 120.47(7) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.64(7) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.22(7) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.81(7) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.42(7) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N3 C2 N1 107.46(6) . . ?
N3 C2 C21 124.36(6) . . ?
N1 C2 C21 128.18(6) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 N3 C4 109.35(6) . . ?
C2 N3 C31 125.01(6) . . ?
C4 N3 C31 125.56(6) . . ?
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C5 C4 N3 107.00(6) . . ?
C5 C4 H4 126.5 . . ?
N3 C4 H4 126.5 . . ?
C4 C5 N1 107.06(6) . . ?
C4 C5 H5 126.5 . . ?
N1 C5 H5 126.5 . . ?

#============================================================================
data_jak281
_database_code_depnum_ccdc_archive 'CCDC 720678'

_audit_creation_date             2009-02-10T14:44:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C15 H21 I N2'
_chemical_formula_moiety         'C15 H21 N2, I'
_chemical_formula_weight         356.24
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  p_2ac_2ab
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.4229(1)
_cell_length_b                   11.8744(1)
_cell_length_c                   13.8521(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1549.93(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29783
_cell_measurement_theta_min      3.7248
_cell_measurement_theta_max      45.5547

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4915
_exptl_crystal_size_mid          0.2721
_exptl_crystal_size_min          0.1627
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.053
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_T_max  0.751

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      -0.0243975307
_diffrn_orient_matrix_ub_12      0.0187334162
_diffrn_orient_matrix_ub_13      -0.0456977352
_diffrn_orient_matrix_ub_21      -0.0154177316
_diffrn_orient_matrix_ub_22      -0.0563776501
_diffrn_orient_matrix_ub_23      -0.0131411065
_diffrn_orient_matrix_ub_31      -0.0694822214
_diffrn_orient_matrix_ub_32      0.0059719268
_diffrn_orient_matrix_ub_33      0.0189924677
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_number            58825
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         45.73
_diffrn_reflns_theta_full        45.73
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  
;
Oxford Diffraction Gemini diffractometer
;
_diffrn_measurement_method       'ω scans'
_reflns_number_total             13178
_reflns_number_gt                11264
_reflns_threshold_expression     I>2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep2
_computing_publication_material  WinGX

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0193P)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_number_reflns         13178
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0435
_refine_ls_wR_factor_gt          0.0417
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(8)
_refine_diff_density_max         1.522
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.086

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.288490(5) 0.245047(5) 0.797157(4) 0.015110(10) Uani 1 1 d . . .
N1 N 0.56958(8) 0.37730(7) 0.46461(6) 0.01455(13) Uani 1 1 d . . .
C1 C 0.64995(9) 0.27225(7) 0.48022(7) 0.01617(15) Uani 1 1 d . . .
H1A H 0.7044 0.2783 0.5411 0.019 Uiso 1 1 calc R . .
H1B H 0.7185 0.262 0.4268 0.019 Uiso 1 1 calc R . .
C11 C 0.55379(9) 0.17084(8) 0.48538(7) 0.01417(14) Uani 1 1 d . . .
C12 C 0.51333(11) 0.12530(9) 0.57371(8) 0.01850(16) Uani 1 1 d . . .
H12 H 0.5463 0.1583 0.632 0.022 Uiso 1 1 calc R . .
C13 C 0.42461(12) 0.03154(9) 0.57709(9) 0.02180(18) Uani 1 1 d . . .
H13 H 0.3974 0.0007 0.6376 0.026 Uiso 1 1 calc R . .
C14 C 0.37604(10) -0.01670(8) 0.49222(9) 0.02020(17) Uani 1 1 d . . .
H14 H 0.3162 -0.081 0.4946 0.024 Uiso 1 1 calc R . .
C15 C 0.41472(10) 0.02892(8) 0.40367(8) 0.01841(17) Uani 1 1 d . . .
H15 H 0.3804 -0.0037 0.3456 0.022 Uiso 1 1 calc R . .
C16 C 0.50369(10) 0.12233(8) 0.40006(8) 0.01615(15) Uani 1 1 d . . .
H16 H 0.5304 0.1532 0.3395 0.019 Uiso 1 1 calc R . .
C2 C 0.52406(9) 0.44955(7) 0.53252(7) 0.01334(13) Uani 1 1 d . . .
C21 C 0.54331(11) 0.43875(9) 0.63829(7) 0.01831(16) Uani 1 1 d . . .
H21A H 0.5534 0.5138 0.6669 0.027 Uiso 1 1 calc R . .
H21B H 0.6288 0.3944 0.6516 0.027 Uiso 1 1 calc R . .
H21C H 0.4605 0.4009 0.6663 0.027 Uiso 1 1 calc R . .
N3 N 0.45563(8) 0.53289(7) 0.48729(6) 0.01457(13) Uani 1 1 d . . .
C31 C 0.38886(9) 0.63141(8) 0.53344(7) 0.01443(14) Uani 1 1 d . . .
H31A H 0.3823 0.6935 0.486 0.017 Uiso 1 1 calc R . .
H31B H 0.4491 0.6573 0.5876 0.017 Uiso 1 1 calc R . .
C32 C 0.24094(10) 0.60398(8) 0.57124(8) 0.01742(16) Uani 1 1 d . . .
H32A H 0.2483 0.5472 0.6233 0.021 Uiso 1 1 calc R . .
H32B H 0.1834 0.5712 0.5185 0.021 Uiso 1 1 calc R . .
C33 C 0.16701(10) 0.70900(9) 0.61009(8) 0.01819(16) Uani 1 1 d . . .
H33A H 0.1642 0.7665 0.5584 0.022 Uiso 1 1 calc R . .
H33B H 0.0678 0.6895 0.6265 0.022 Uiso 1 1 calc R . .
C34 C 0.23772(11) 0.76004(12) 0.69879(8) 0.0286(2) Uani 1 1 d . . .
H34A H 0.2348 0.7058 0.752 0.043 Uiso 1 1 calc R . .
H34B H 0.1872 0.8287 0.7176 0.043 Uiso 1 1 calc R . .
H34C H 0.3367 0.7784 0.6837 0.043 Uiso 1 1 calc R . .
C4 C 0.45605(11) 0.51325(9) 0.38909(8) 0.01902(16) Uani 1 1 d . . .
H4 H 0.4141 0.5593 0.3408 0.023 Uiso 1 1 calc R . .
C5 C 0.52805(12) 0.41546(9) 0.37470(8) 0.01896(17) Uani 1 1 d . . .
H5 H 0.5463 0.3801 0.3144 0.023 Uiso 1 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
N1 C2 1.3435(12) . ?
N1 C5 1.3818(14) . ?
N1 C1 1.4753(12) . ?
C1 C11 1.5087(13) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C11 C12 1.3910(15) . ?
C11 C16 1.3969(14) . ?
C12 C13 1.3931(15) . ?
C12 H12 0.95 . ?
C13 C14 1.3855(17) . ?
C13 H13 0.95 . ?
C14 C15 1.3895(17) . ?
C14 H14 0.95 . ?
C15 C16 1.3913(14) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C2 N3 1.3370(12) . ?
C2 C21 1.4819(14) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
N3 C4 1.3802(14) . ?
N3 C31 1.4741(12) . ?
C31 C32 1.5242(13) . ?
C31 H31A 0.99 . ?
C31 H31B 0.99 . ?
C32 C33 1.5264(14) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
C33 C34 1.5234(15) . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
C34 H34A 0.98 . ?
C34 H34B 0.98 . ?
C34 H34C 0.98 . ?
C4 C5 1.3595(14) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?

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 C5 109.35(8) . . ?
C2 N1 C1 126.95(8) . . ?
C5 N1 C1 123.70(8) . . ?
N1 C1 C11 111.93(7) . . ?
N1 C1 H1A 109.2 . . ?
C11 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C11 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C12 C11 C16 119.43(9) . . ?
C12 C11 C1 121.10(9) . . ?
C16 C11 C1 119.47(9) . . ?
C11 C12 C13 120.31(10) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.01(10) . . ?
C14 C13 H13 120 . . ?
C12 C13 H13 120 . . ?
C13 C14 C15 120.08(9) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C14 C15 C16 120.04(10) . . ?
C14 C15 H15 120 . . ?
C16 C15 H15 120 . . ?
C15 C16 C11 120.13(10) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N3 C2 N1 107.36(8) . . ?
N3 C2 C21 125.90(9) . . ?
N1 C2 C21 126.73(9) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 N3 C4 109.60(8) . . ?
C2 N3 C31 126.16(9) . . ?
C4 N3 C31 124.24(8) . . ?
N3 C31 C32 111.69(8) . . ?
N3 C31 H31A 109.3 . . ?
C32 C31 H31A 109.3 . . ?
N3 C31 H31B 109.3 . . ?
C32 C31 H31B 109.3 . . ?
H31A C31 H31B 107.9 . . ?
C31 C32 C33 111.34(8) . . ?
C31 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
C31 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108 . . ?
C34 C33 C32 114.19(9) . . ?
C34 C33 H33A 108.7 . . ?
C32 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
C32 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C5 C4 N3 106.87(9) . . ?
C5 C4 H4 126.6 . . ?
N3 C4 H4 126.6 . . ?
C4 C5 N1 106.82(9) . . ?
C4 C5 H5 126.6 . . ?
N1 C5 H5 126.6 . . ?

#============================================================================
data_jak131
_database_code_depnum_ccdc_archive 'CCDC 720679'

_audit_creation_date             2009-02-11T18:50:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C16 H23 I N2'
_chemical_formula_moiety         'C16 H23 N2, I'
_chemical_formula_weight         370.26

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  -p_2ac_2ab
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   20.7565(3)
_cell_length_b                   14.0490(2)
_cell_length_c                   23.2945(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6792.86(18)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30690
_cell_measurement_theta_min      2.5833
_cell_measurement_theta_max      34.4721

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2976
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_T_max  0.735

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0009
_diffrn_orient_matrix_ub_11      0.0111948857
_diffrn_orient_matrix_ub_12      0.0028378196
_diffrn_orient_matrix_ub_13      -0.0296122652
_diffrn_orient_matrix_ub_21      0.0002430399
_diffrn_orient_matrix_ub_22      -0.0340595187
_diffrn_orient_matrix_ub_23      -0.0025790843
_diffrn_orient_matrix_ub_31      -0.0492644206
_diffrn_orient_matrix_ub_32      0.0004518824
_diffrn_orient_matrix_ub_33      -0.0067449301
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_number            101051
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         34.56
_diffrn_reflns_theta_full        33.75
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur diffractometer
;
_diffrn_measurement_method       'ω scans'
_reflns_number_total             13863
_reflns_number_gt                8921
_reflns_threshold_expression     I>2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    OrtepII
_computing_publication_material  WinGX

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0681P)²+10.9425P] 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_number_reflns         13863
_refine_ls_number_parameters     346
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_diff_density_max         3.21
_refine_diff_density_min         -1.1
_refine_diff_density_rms         0.14

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.280303(11) 0.718105(15) 0.011446(10) 0.02647(6) Uani 1 1 d . . .
I2 I 0.985058(14) 0.283960(19) 0.272303(12) 0.03958(8) Uani 1 1 d . . .
N11 N 0.11370(17) 0.5682(2) 0.12466(14) 0.0341(7) Uani 1 1 d . . .
C11 C 0.11868(17) 0.6581(2) 0.09305(15) 0.0254(6) Uani 1 1 d . . .
H11A H 0.1626 0.6651 0.0771 0.03 Uiso 1 1 calc R . .
H11B H 0.1106 0.7122 0.1193 0.03 Uiso 1 1 calc R . .
C111 C 0.07008(18) 0.6590(2) 0.04517(15) 0.0280(7) Uani 1 1 d . . .
C112 C 0.0844(2) 0.6188(4) -0.00755(18) 0.0510(12) Uani 1 1 d . . .
H112 H 0.1258 0.5922 -0.0141 0.061 Uiso 1 1 calc R . .
C113 C 0.0383(3) 0.6172(5) -0.0512(2) 0.0673(17) Uani 1 1 d . . .
H113 H 0.0482 0.5897 -0.0874 0.081 Uiso 1 1 calc R . .
C114 C -0.0217(3) 0.6558(4) -0.0413(2) 0.0640(17) Uani 1 1 d . . .
H114 H -0.0534 0.6545 -0.0707 0.077 Uiso 1 1 calc R . .
C115 C -0.0362(3) 0.6959(4) 0.0103(3) 0.0629(15) Uani 1 1 d . . .
H115 H -0.0777 0.7226 0.0164 0.076 Uiso 1 1 calc R . .
C116 C 0.0096(2) 0.6981(3) 0.0545(2) 0.0421(10) Uani 1 1 d . . .
H116 H -0.0007 0.7261 0.0905 0.05 Uiso 1 1 calc R . .
C12 C 0.1478(2) 0.4902(3) 0.11851(18) 0.0383(9) Uani 1 1 d . . .
C121 C 0.2038(3) 0.4780(5) 0.0803(3) 0.090(3) Uani 1 1 d . . .
H12A H 0.1891 0.457 0.0424 0.135 Uiso 1 1 calc R . .
H12B H 0.2329 0.4301 0.0965 0.135 Uiso 1 1 calc R . .
H12C H 0.2267 0.5387 0.0766 0.135 Uiso 1 1 calc R . .
N13 N 0.12691(19) 0.4233(2) 0.15362(14) 0.0380(8) Uani 1 1 d . . .
C131 C 0.1479(2) 0.3258(3) 0.16232(18) 0.0378(9) Uani 1 1 d . . .
H13A H 0.1622 0.2988 0.1252 0.045 Uiso 1 1 calc R . .
H13B H 0.1111 0.2873 0.1762 0.045 Uiso 1 1 calc R . .
C132 C 0.2014(3) 0.3193(4) 0.2044(3) 0.0701(18) Uani 1 1 d . . .
H13C H 0.187 0.3413 0.2426 0.084 Uiso 1 1 calc R . .
H13D H 0.2382 0.3592 0.1919 0.084 Uiso 1 1 calc R . .
C133 C 0.2219(3) 0.2107(3) 0.2069(3) 0.0563(13) Uani 1 1 d . . .
H13E H 0.1852 0.173 0.2217 0.068 Uiso 1 1 calc R . .
H13F H 0.2311 0.1884 0.1674 0.068 Uiso 1 1 calc R . .
C134 C 0.2763(3) 0.1927(4) 0.2416(4) 0.0722(19) Uani 1 1 d . . .
H13G H 0.27 0.2233 0.2795 0.087 Uiso 1 1 calc R . .
H13H H 0.3147 0.222 0.2236 0.087 Uiso 1 1 calc R . .
C135 C 0.2889(3) 0.0869(3) 0.2505(2) 0.0554(13) Uani 1 1 d . . .
H13I H 0.2499 0.0565 0.2656 0.083 Uiso 1 1 calc R . .
H13J H 0.3243 0.0786 0.2778 0.083 Uiso 1 1 calc R . .
H13K H 0.3004 0.0577 0.2137 0.083 Uiso 1 1 calc R . .
C14 C 0.0726(3) 0.4611(4) 0.1830(2) 0.0519(12) Uani 1 1 d . . .
H14 H 0.0467 0.4287 0.2103 0.062 Uiso 1 1 calc R . .
C15 C 0.0650(2) 0.5479(4) 0.1655(2) 0.0590(15) Uani 1 1 d . . .
H15 H 0.0324 0.5906 0.178 0.071 Uiso 1 1 calc R . .
N21 N 0.32836(16) 0.4305(2) 0.90637(15) 0.0342(7) Uani 1 1 d . . .
C21 C 0.26827(17) 0.4676(3) 0.93310(16) 0.0299(7) Uani 1 1 d . . .
H21A H 0.2772 0.5303 0.9508 0.036 Uiso 1 1 calc R . .
H21B H 0.2543 0.4236 0.9639 0.036 Uiso 1 1 calc R . .
C211 C 0.21415(18) 0.4783(3) 0.88942(17) 0.0308(7) Uani 1 1 d . . .
C212 C 0.2033(2) 0.5643(3) 0.8623(2) 0.0408(10) Uani 1 1 d . . .
H212 H 0.2294 0.6178 0.8714 0.049 Uiso 1 1 calc R . .
C213 C 0.1548(2) 0.5731(3) 0.8218(2) 0.0465(11) Uani 1 1 d . . .
H213 H 0.1481 0.6324 0.8031 0.056 Uiso 1 1 calc R . .
C214 C 0.1160(2) 0.4961(4) 0.8086(2) 0.0466(11) Uani 1 1 d . . .
H214 H 0.0831 0.5019 0.7805 0.056 Uiso 1 1 calc R . .
C215 C 0.1256(2) 0.4104(4) 0.8366(2) 0.0488(11) Uani 1 1 d . . .
H215 H 0.0988 0.3574 0.8281 0.059 Uiso 1 1 calc R . .
C216 C 0.1742(2) 0.4014(3) 0.87712(19) 0.0385(9) Uani 1 1 d . . .
H216 H 0.1802 0.3425 0.8965 0.046 Uiso 1 1 calc R . .
C22 C 0.37660(19) 0.4807(3) 0.88446(17) 0.0334(8) Uani 1 1 d . . .
C221 C 0.3810(3) 0.5859(3) 0.8840(2) 0.0537(13) Uani 1 1 d . . .
H22A H 0.3484 0.6118 0.8578 0.08 Uiso 1 1 calc R . .
H22B H 0.424 0.6051 0.8709 0.08 Uiso 1 1 calc R . .
H22C H 0.3735 0.6104 0.9228 0.08 Uiso 1 1 calc R . .
N23 N 0.41980(16) 0.4204(2) 0.86221(16) 0.0384(8) Uani 1 1 d . . .
C231 C 0.4813(2) 0.4408(3) 0.8335(2) 0.0437(11) Uani 1 1 d . . .
H23A H 0.487 0.5106 0.83 0.052 Uiso 1 1 calc R . .
H23B H 0.4808 0.4134 0.7943 0.052 Uiso 1 1 calc R . .
C232 C 0.5370(3) 0.3989(4) 0.8674(4) 0.084(2) Uani 1 1 d D B .
H23C H 0.5274 0.331 0.8746 0.101 Uiso 1 1 calc R . .
H23D H 0.576 0.4014 0.8429 0.101 Uiso 1 1 calc R . .
C233 C 0.5520(4) 0.4411(5) 0.9196(4) 0.100(3) Uani 1 1 d D . .
H23E H 0.578 0.3976 0.9437 0.12 Uiso 0.5 1 calc PR A 1
H23F H 0.5123 0.4582 0.9408 0.12 Uiso 0.5 1 calc PR A 1
H23L H 0.5907 0.4058 0.9323 0.12 Uiso 0.5 1 d PR A 2
H23M H 0.5169 0.4194 0.9453 0.12 Uiso 0.5 1 d PR A 2
C234 C 0.5924(5) 0.5346(7) 0.9033(4) 0.048(2) Uiso 0.5 1 d PD B 1
H23G H 0.6301 0.5182 0.8793 0.058 Uiso 0.5 1 calc PR B 1
H23H H 0.5652 0.5809 0.8823 0.058 Uiso 0.5 1 calc PR B 1
C235 C 0.6137(5) 0.5749(7) 0.9607(5) 0.051(2) Uiso 0.5 1 d PD B 1
H23I H 0.5757 0.588 0.9844 0.077 Uiso 0.5 1 calc PR B 1
H23J H 0.6376 0.6342 0.9544 0.077 Uiso 0.5 1 calc PR B 1
H23K H 0.6414 0.5288 0.9802 0.077 Uiso 0.5 1 calc PR B 1
C236 C 0.5644(10) 0.5427(14) 0.9399(10) 0.136(7) Uiso 0.5 1 d PD B 2
H23N H 0.5348 0.5867 0.9197 0.163 Uiso 0.5 1 calc PR B 2
H23O H 0.5556 0.5473 0.9815 0.163 Uiso 0.5 1 calc PR B 2
C237 C 0.6304(6) 0.5702(9) 0.9287(6) 0.063(3) Uiso 0.5 1 d PD B 2
H23P H 0.6593 0.5345 0.9541 0.094 Uiso 0.5 1 calc PR B 2
H23Q H 0.6355 0.6385 0.9358 0.094 Uiso 0.5 1 calc PR B 2
H23R H 0.6412 0.5561 0.8886 0.094 Uiso 0.5 1 calc PR B 2
C24 C 0.3979(2) 0.3274(3) 0.8721(2) 0.0500(12) Uani 1 1 d . . .
H24 H 0.4193 0.2704 0.8614 0.06 Uiso 1 1 calc R . .
C25 C 0.3421(2) 0.3334(3) 0.8990(2) 0.0444(11) Uani 1 1 d . . .
H25 H 0.3161 0.2816 0.9111 0.053 Uiso 1 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
N11 C12 1.312(5) . ?
N11 C15 1.417(6) . ?
N11 C11 1.466(5) . ?
C11 C111 1.504(5) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C111 C112 1.384(6) . ?
C111 C116 1.388(6) . ?
C112 C113 1.396(7) . ?
C112 H112 0.95 . ?
C113 C114 1.379(9) . ?
C113 H113 0.95 . ?
C114 C115 1.361(9) . ?
C114 H114 0.95 . ?
C115 C116 1.401(7) . ?
C115 H115 0.95 . ?
C116 H116 0.95 . ?
C12 N13 1.319(5) . ?
C12 C121 1.476(6) . ?
C121 H12A 0.98 . ?
C121 H12B 0.98 . ?
C121 H12C 0.98 . ?
N13 C14 1.420(6) . ?
N13 C131 1.452(5) . ?
C131 C132 1.484(7) . ?
C131 H13A 0.99 . ?
C131 H13B 0.99 . ?
C132 C133 1.585(7) . ?
C132 H13C 0.99 . ?
C132 H13D 0.99 . ?
C133 C134 1.412(9) . ?
C133 H13E 0.99 . ?
C133 H13F 0.99 . ?
C134 C135 1.522(7) . ?
C134 H13G 0.99 . ?
C134 H13H 0.99 . ?
C135 H13I 0.98 . ?
C135 H13J 0.98 . ?
C135 H13K 0.98 . ?
C14 C15 1.294(7) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
N21 C22 1.327(5) . ?
N21 C25 1.404(5) . ?
N21 C21 1.488(5) . ?
C21 C211 1.523(6) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C211 C212 1.382(6) . ?
C211 C216 1.392(5) . ?
C212 C213 1.385(7) . ?
C212 H212 0.95 . ?
C213 C214 1.385(7) . ?
C213 H213 0.95 . ?
C214 C215 1.384(7) . ?
C214 H214 0.95 . ?
C215 C216 1.386(6) . ?
C215 H215 0.95 . ?
C216 H216 0.95 . ?
C22 N23 1.338(5) . ?
C22 C221 1.481(6) . ?
C221 H22A 0.98 . ?
C221 H22B 0.98 . ?
C221 H22C 0.98 . ?
N23 C24 1.402(5) . ?
N23 C231 1.469(5) . ?
C231 C232 1.521(8) . ?
C231 H23A 0.99 . ?
C231 H23B 0.99 . ?
C232 C233 1.388(11) . ?
C232 H23C 0.99 . ?
C232 H23D 0.99 . ?
C233 C236 1.524(19) . ?
C233 C234 1.605(12) . ?
C233 H23E 0.99 . ?
C233 H23F 0.99 . ?
C233 H23L 0.99 . ?
C233 H23M 0.99 . ?
C234 C235 1.516(14) . ?
C234 H23G 0.99 . ?
C234 H23H 0.99 . ?
C235 H23I 0.98 . ?
C235 H23J 0.98 . ?
C235 H23K 0.98 . ?
C236 C237 1.45(2) . ?
C236 H23N 0.99 . ?
C236 H23O 0.99 . ?
C237 H23P 0.98 . ?
C237 H23Q 0.98 . ?
C237 H23R 0.98 . ?
C24 C25 1.317(6) . ?
C24 H24 0.95 . ?
C25 H25 0.95 . ?

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
C12 N11 C15 106.8(4) . . ?
C12 N11 C11 128.8(4) . . ?
C15 N11 C11 124.1(4) . . ?
N11 C11 C111 109.4(3) . . ?
N11 C11 H11A 109.8 . . ?
C111 C11 H11A 109.8 . . ?
N11 C11 H11B 109.8 . . ?
C111 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C112 C111 C116 119.7(4) . . ?
C112 C111 C11 120.7(4) . . ?
C116 C111 C11 119.6(3) . . ?
C111 C112 C113 120.4(5) . . ?
C111 C112 H112 119.8 . . ?
C113 C112 H112 119.8 . . ?
C114 C113 C112 119.3(5) . . ?
C114 C113 H113 120.3 . . ?
C112 C113 H113 120.3 . . ?
C115 C114 C113 120.7(5) . . ?
C115 C114 H114 119.7 . . ?
C113 C114 H114 119.7 . . ?
C114 C115 C116 120.6(5) . . ?
C114 C115 H115 119.7 . . ?
C116 C115 H115 119.7 . . ?
C111 C116 C115 119.3(5) . . ?
C111 C116 H116 120.4 . . ?
C115 C116 H116 120.4 . . ?
N11 C12 N13 110.5(4) . . ?
N11 C12 C121 126.0(4) . . ?
N13 C12 C121 123.4(4) . . ?
C12 C121 H12A 109.5 . . ?
C12 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
C12 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C12 N13 C14 107.0(4) . . ?
C12 N13 C131 131.4(4) . . ?
C14 N13 C131 121.6(4) . . ?
N13 C131 C132 112.0(4) . . ?
N13 C131 H13A 109.2 . . ?
C132 C131 H13A 109.2 . . ?
N13 C131 H13B 109.2 . . ?
C132 C131 H13B 109.2 . . ?
H13A C131 H13B 107.9 . . ?
C131 C132 C133 106.5(5) . . ?
C131 C132 H13C 110.4 . . ?
C133 C132 H13C 110.4 . . ?
C131 C132 H13D 110.4 . . ?
C133 C132 H13D 110.4 . . ?
H13C C132 H13D 108.6 . . ?
C134 C133 C132 114.1(5) . . ?
C134 C133 H13E 108.7 . . ?
C132 C133 H13E 108.7 . . ?
C134 C133 H13F 108.7 . . ?
C132 C133 H13F 108.7 . . ?
H13E C133 H13F 107.6 . . ?
C133 C134 C135 112.9(6) . . ?
C133 C134 H13G 109 . . ?
C135 C134 H13G 109 . . ?
C133 C134 H13H 109 . . ?
C135 C134 H13H 109 . . ?
H13G C134 H13H 107.8 . . ?
C134 C135 H13I 109.5 . . ?
C134 C135 H13J 109.5 . . ?
H13I C135 H13J 109.5 . . ?
C134 C135 H13K 109.5 . . ?
H13I C135 H13K 109.5 . . ?
H13J C135 H13K 109.5 . . ?
C15 C14 N13 107.4(4) . . ?
C15 C14 H14 126.3 . . ?
N13 C14 H14 126.3 . . ?
C14 C15 N11 108.3(4) . . ?
C14 C15 H15 125.9 . . ?
N11 C15 H15 125.9 . . ?
C22 N21 C25 108.4(3) . . ?
C22 N21 C21 127.3(3) . . ?
C25 N21 C21 124.2(3) . . ?
N21 C21 C211 111.9(3) . . ?
N21 C21 H21A 109.2 . . ?
C211 C21 H21A 109.2 . . ?
N21 C21 H21B 109.2 . . ?
C211 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C212 C211 C216 119.2(4) . . ?
C212 C211 C21 120.8(4) . . ?
C216 C211 C21 120.0(4) . . ?
C211 C212 C213 120.5(4) . . ?
C211 C212 H212 119.7 . . ?
C213 C212 H212 119.7 . . ?
C214 C213 C212 120.3(4) . . ?
C214 C213 H213 119.9 . . ?
C212 C213 H213 119.9 . . ?
C215 C214 C213 119.4(4) . . ?
C215 C214 H214 120.3 . . ?
C213 C214 H214 120.3 . . ?
C214 C215 C216 120.4(4) . . ?
C214 C215 H215 119.8 . . ?
C216 C215 H215 119.8 . . ?
C215 C216 C211 120.2(4) . . ?
C215 C216 H216 119.9 . . ?
C211 C216 H216 119.9 . . ?
N21 C22 N23 108.5(3) . . ?
N21 C22 C221 125.5(4) . . ?
N23 C22 C221 126.0(4) . . ?
C22 C221 H22A 109.5 . . ?
C22 C221 H22B 109.5 . . ?
H22A C221 H22B 109.5 . . ?
C22 C221 H22C 109.5 . . ?
H22A C221 H22C 109.5 . . ?
H22B C221 H22C 109.5 . . ?
C22 N23 C24 108.0(3) . . ?
C22 N23 C231 129.4(4) . . ?
C24 N23 C231 122.6(3) . . ?
N23 C231 C232 110.4(4) . . ?
N23 C231 H23A 109.6 . . ?
C232 C231 H23A 109.6 . . ?
N23 C231 H23B 109.6 . . ?
C232 C231 H23B 109.6 . . ?
H23A C231 H23B 108.1 . . ?
C233 C232 C231 117.4(6) . . ?
C233 C232 H23C 108 . . ?
C231 C232 H23C 108 . . ?
C233 C232 H23D 108 . . ?
C231 C232 H23D 108 . . ?
H23C C232 H23D 107.2 . . ?
C232 C233 C236 135.1(12) . . ?
C232 C233 C234 105.0(8) . . ?
C232 C233 H23E 110.7 . . ?
C236 C233 H23E 108.1 . . ?
C234 C233 H23E 110.7 . . ?
C232 C233 H23F 110.7 . . ?
C234 C233 H23F 110.7 . . ?
H23E C233 H23F 108.8 . . ?
C232 C233 H23L 103.3 . . ?
C236 C233 H23L 103.8 . . ?
C232 C233 H23M 103.5 . . ?
C236 C233 H23M 103 . . ?
H23L C233 H23M 105.2 . . ?
C235 C234 C233 104.4(8) . . ?
C235 C234 H23G 110.9 . . ?
C233 C234 H23G 110.9 . . ?
C235 C234 H23H 110.9 . . ?
C233 C234 H23H 110.9 . . ?
H23G C234 H23H 108.9 . . ?
C237 C236 C233 110.7(15) . . ?
C237 C236 H23N 109.5 . . ?
C233 C236 H23N 109.5 . . ?
C237 C236 H23O 109.5 . . ?
C233 C236 H23O 109.5 . . ?
H23N C236 H23O 108.1 . . ?
C236 C237 H23P 109.5 . . ?
C236 C237 H23Q 109.5 . . ?
H23P C237 H23Q 109.5 . . ?
C236 C237 H23R 109.5 . . ?
H23P C237 H23R 109.5 . . ?
H23Q C237 H23R 109.5 . . ?
C25 C24 N23 107.7(4) . . ?
C25 C24 H24 126.2 . . ?
N23 C24 H24 126.2 . . ?
C24 C25 N21 107.4(4) . . ?
C24 C25 H25 126.3 . . ?
N21 C25 H25 126.3 . . ?
#============================================================================
data_jak230
_database_code_depnum_ccdc_archive 'CCDC 720680'

_audit_creation_date             2009-02-09T23:32:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C15 H21 I N2'
_chemical_formula_moiety         'C15 H21 N2, I'
_chemical_formula_weight         356.24

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  -p_2ybc

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                   12.2127(2)
_cell_length_b                   11.3954(2)
_cell_length_c                   11.6217(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.097(2)
_cell_angle_gamma                90
_cell_volume                     1553.96(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19441
_cell_measurement_theta_min      3.354
_cell_measurement_theta_max      38.7772

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.048
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_T_max  0.664

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      0.0139896577
_diffrn_orient_matrix_ub_12      0.0408910665
_diffrn_orient_matrix_ub_13      0.0455563733
_diffrn_orient_matrix_ub_21      -0.0149740249
_diffrn_orient_matrix_ub_22      -0.0424575187
_diffrn_orient_matrix_ub_23      0.0362322102
_diffrn_orient_matrix_ub_31      0.0601345147
_diffrn_orient_matrix_ub_32      -0.0200686396
_diffrn_orient_matrix_ub_33      0.0161465376
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_number            34403
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         38.86
_diffrn_reflns_theta_full        38
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  
;
Oxford Diffraction Gemini diffractometer
;
_diffrn_measurement_method       'ω scans'
_reflns_number_total             8685
_reflns_number_gt                7000
_reflns_threshold_expression     I>2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    OrtepII
_computing_publication_material  WinGX
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0251P)²] 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_number_reflns         8685
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.021
_refine_ls_wR_factor_ref         0.0501
_refine_ls_wR_factor_gt          0.0477
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.36
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.094

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.348302(5) 0.472798(5) 0.198795(5) 0.01588(2) Uani 1 1 d . . .
N1 N 0.32756(7) 0.55015(7) 0.81273(7) 0.01370(13) Uani 1 1 d . . .
C1 C 0.30835(8) 0.64953(9) 0.88559(9) 0.01596(16) Uani 1 1 d . . .
H1A H 0.3482 0.7197 0.8672 0.019 Uiso 1 1 calc R . .
H1B H 0.3407 0.6308 0.9715 0.019 Uiso 1 1 calc R . .
C11 C 0.18250(8) 0.67623(8) 0.86135(8) 0.01453(15) Uani 1 1 d . . .
C12 C 0.13583(9) 0.77781(10) 0.80091(9) 0.02094(19) Uani 1 1 d . . .
H12 H 0.1829 0.8315 0.774 0.025 Uiso 1 1 calc R . .
C13 C 0.01969(10) 0.80056(11) 0.78000(11) 0.0255(2) Uani 1 1 d . . .
H13 H -0.0121 0.8703 0.7395 0.031 Uiso 1 1 calc R . .
C14 C -0.04937(9) 0.72219(11) 0.81791(10) 0.0236(2) Uani 1 1 d . . .
H14 H -0.1285 0.738 0.803 0.028 Uiso 1 1 calc R . .
C15 C -0.00353(9) 0.62043(12) 0.87772(10) 0.0241(2) Uani 1 1 d . . .
H15 H -0.0512 0.5665 0.9034 0.029 Uiso 1 1 calc R . .
C16 C 0.11266(9) 0.59748(10) 0.90013(9) 0.01988(18) Uani 1 1 d . . .
H16 H 0.1443 0.5282 0.9418 0.024 Uiso 1 1 calc R . .
C2 C 0.32567(8) 0.55512(9) 0.69672(8) 0.01407(15) Uani 1 1 d . . .
C21 C 0.31370(11) 0.66355(10) 0.62407(10) 0.0226(2) Uani 1 1 d . . .
H21A H 0.3568 0.6553 0.5648 0.034 Uiso 1 1 calc R . .
H21B H 0.3434 0.7304 0.6765 0.034 Uiso 1 1 calc R . .
H21C H 0.2331 0.6767 0.5828 0.034 Uiso 1 1 calc R . .
N3 N 0.33620(7) 0.44529(7) 0.66014(7) 0.01382(13) Uani 1 1 d . . .
C31 C 0.33303(8) 0.40786(9) 0.53720(8) 0.01534(15) Uani 1 1 d . . .
H31 H 0.3347 0.4799 0.4885 0.018 Uiso 1 1 calc R . .
C32 C 0.43810(8) 0.33495(10) 0.53993(9) 0.01847(17) Uani 1 1 d . . .
H32A H 0.5067 0.378 0.5831 0.028 Uiso 1 1 calc R . .
H32B H 0.4408 0.3196 0.4578 0.028 Uiso 1 1 calc R . .
H32C H 0.4345 0.2603 0.5807 0.028 Uiso 1 1 calc R . .
C33 C 0.22211(8) 0.34245(10) 0.48014(9) 0.01874(17) Uani 1 1 d . . .
H33A H 0.222 0.3172 0.3986 0.022 Uiso 1 1 calc R . .
H33B H 0.2193 0.271 0.5277 0.022 Uiso 1 1 calc R . .
C34 C 0.11545(9) 0.41562(11) 0.47180(10) 0.0237(2) Uani 1 1 d . . .
H34A H 0.1122 0.4367 0.5525 0.036 Uiso 1 1 calc R . .
H34B H 0.0477 0.3699 0.4316 0.036 Uiso 1 1 calc R . .
H34C H 0.118 0.4872 0.4259 0.036 Uiso 1 1 calc R . .
C4 C 0.34549(8) 0.36867(8) 0.75513(8) 0.01545(16) Uani 1 1 d . . .
H4 H 0.3541 0.2859 0.7536 0.019 Uiso 1 1 calc R . .
C5 C 0.34002(8) 0.43456(9) 0.85053(8) 0.01562(16) Uani 1 1 d . . .
H5 H 0.344 0.4066 0.9286 0.019 Uiso 1 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
N1 C2 1.3432(12) . ?
N1 C5 1.3835(13) . ?
N1 C1 1.4713(12) . ?
C1 C11 1.5146(13) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C11 C12 1.3915(15) . ?
C11 C16 1.3961(14) . ?
C12 C13 1.3954(15) . ?
C12 H12 0.95 . ?
C13 C14 1.3817(18) . ?
C13 H13 0.95 . ?
C14 C15 1.3876(18) . ?
C14 H14 0.95 . ?
C15 C16 1.3945(14) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C2 N3 1.3395(13) . ?
C2 C21 1.4806(14) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
N3 C4 1.3873(13) . ?
N3 C31 1.4812(12) . ?
C31 C32 1.5217(14) . ?
C31 C33 1.5271(14) . ?
C31 H31 1 . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
C33 C34 1.5269(15) . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
C34 H34A 0.98 . ?
C34 H34B 0.98 . ?
C34 H34C 0.98 . ?
C4 C5 1.3560(14) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?

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 C5 109.19(8) . . ?
C2 N1 C1 125.74(9) . . ?
C5 N1 C1 124.82(8) . . ?
N1 C1 C11 111.29(8) . . ?
N1 C1 H1A 109.4 . . ?
C11 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
C11 C1 H1B 109.4 . . ?
H1A C1 H1B 108 . . ?
C12 C11 C16 119.76(9) . . ?
C12 C11 C1 120.90(9) . . ?
C16 C11 C1 119.35(9) . . ?
C11 C12 C13 119.78(10) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.35(11) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.18(10) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 119.91(11) . . ?
C14 C15 H15 120 . . ?
C16 C15 H15 120 . . ?
C15 C16 C11 120.02(10) . . ?
C15 C16 H16 120 . . ?
C11 C16 H16 120 . . ?
N3 C2 N1 107.62(8) . . ?
N3 C2 C21 126.99(9) . . ?
N1 C2 C21 125.39(9) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 N3 C4 109.23(8) . . ?
C2 N3 C31 126.59(8) . . ?
C4 N3 C31 124.12(8) . . ?
N3 C31 C32 109.92(8) . . ?
N3 C31 C33 110.01(8) . . ?
C32 C31 C33 112.58(9) . . ?
N3 C31 H31 108.1 . . ?
C32 C31 H31 108.1 . . ?
C33 C31 H31 108.1 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C31 113.55(9) . . ?
C34 C33 H33A 108.9 . . ?
C31 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C31 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C5 C4 N3 106.89(9) . . ?
C5 C4 H4 126.6 . . ?
N3 C4 H4 126.6 . . ?
C4 C5 N1 107.07(8) . . ?
C4 C5 H5 126.5 . . ?
N1 C5 H5 126.5 . . ?

#=========================================================================END


