# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
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data_1 #
_database_code_depnum_ccdc_archive 'CCDC 910540'
#TrackingRef '15367_web_deposit_cif_file_0_AnnaM.Plonka_1352733474.Jin_etal_CrystEngComm.cif'
_audit_creation_date             11/12/2012
_audit_creation_method           'from SHELXL97 CIF and IUCr SHELXL97-template'
_chemical_name_systematic        
;
?
;
_chemical_name_common            'PIDA cocrystal with oxalamide host'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 I2 N4 O2'
_chemical_formula_weight         572.13
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   4.9330(3)
_cell_length_b                   8.4214(5)
_cell_length_c                   12.3642(8)
_cell_angle_alpha                100.542(5)
_cell_angle_beta                 82.986(5)
_cell_angle_gamma                97.144(5)
_cell_volume                     498.45(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    3.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2998
_exptl_absorpt_correction_T_max  0.7420
_exptl_absorpt_process_details   CrysAlisPRO
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13901
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2038
_reflns_number_gt                1220
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1060P)^2^+1.5117P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2038
_refine_ls_number_parameters     118
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1787
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.43319(16) 0.74718(9) 0.58459(8) 0.0863(5) Uani 1 1 d . . .
O1 O -0.7244(17) 0.0489(12) 0.9163(7) 0.086(2) Uani 1 1 d . . .
N2 N -0.2666(18) 0.0687(11) 0.8935(8) 0.069(2) Uani 1 1 d . . .
H2 H -0.1231 0.0573 0.9233 0.082 Uiso 1 1 calc R . .
C3 C -0.008(4) 0.631(2) 0.8141(16) 0.128(6) Uani 1 1 d D . .
H3 H 0.0434 0.7424 0.8188 0.154 Uiso 1 1 calc R . .
C6 C -0.149(2) 0.3089(14) 0.7997(10) 0.071(3) Uani 1 1 d D . .
C1 C 0.5860(19) 0.9533(12) 0.5131(9) 0.059(2) Uani 1 1 d . . .
C8 C -0.229(3) 0.1254(15) 0.7900(10) 0.074(3) Uani 1 1 d . . .
H8A H -0.3974 0.0972 0.7548 0.089 Uiso 1 1 calc R . .
H8B H -0.0863 0.0694 0.7425 0.089 Uiso 1 1 calc R . .
C9 C -0.511(2) 0.0327(13) 0.9462(9) 0.064(3) Uani 1 1 d . . .
C2 C 0.8770(19) 0.9890(13) 0.5034(9) 0.060(3) Uani 1 1 d . . .
N1 N 0.111(3) 0.5319(19) 0.7367(14) 0.139(6) Uani 1 1 d D . .
C5 C -0.266(4) 0.413(3) 0.8768(18) 0.182(10) Uani 1 1 d DU . .
H5 H -0.4010 0.3754 0.9284 0.219 Uiso 1 1 calc R . .
C7 C 0.034(3) 0.3718(19) 0.7330(13) 0.122(6) Uani 1 1 d D . .
H7 H 0.1216 0.3008 0.6770 0.146 Uiso 1 1 calc R . .
C4 C -0.192(5) 0.582(3) 0.8835(19) 0.194(11) Uani 1 1 d DU . .
H4 H -0.2776 0.6558 0.9384 0.233 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0801(6) 0.0700(6) 0.1169(8) 0.0505(5) -0.0060(4) -0.0076(4)
O1 0.059(5) 0.118(7) 0.090(6) 0.054(5) 0.000(4) -0.001(4)
N2 0.065(5) 0.068(6) 0.075(6) 0.031(5) -0.001(4) -0.009(4)
C3 0.161(16) 0.064(9) 0.153(16) 0.052(10) 0.037(13) -0.006(9)
C6 0.076(7) 0.065(7) 0.074(7) 0.026(6) 0.008(6) 0.007(5)
C1 0.058(6) 0.053(5) 0.067(6) 0.027(5) 0.001(4) -0.006(4)
C8 0.079(7) 0.074(7) 0.070(7) 0.029(6) -0.001(5) -0.004(6)
C9 0.062(7) 0.059(6) 0.070(7) 0.024(5) 0.004(5) -0.003(5)
C2 0.053(5) 0.065(6) 0.066(6) 0.026(5) 0.000(5) 0.000(5)
N1 0.152(13) 0.084(9) 0.171(15) 0.057(10) 0.052(11) -0.016(8)
C5 0.215(19) 0.105(13) 0.200(18) 0.059(13) 0.119(16) -0.001(12)
C7 0.143(14) 0.077(9) 0.134(14) 0.039(9) 0.052(11) 0.000(9)
C4 0.24(2) 0.106(14) 0.20(2) 0.026(14) 0.118(17) 0.014(14)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.106(9) . ?
O1 C9 1.189(13) . ?
N2 C9 1.326(13) . ?
N2 C8 1.429(14) . ?
N2 H2 0.8600 . ?
C3 C4 1.25(2) . ?
C3 N1 1.29(2) . ?
C3 H3 0.9300 . ?
C6 C7 1.279(17) . ?
C6 C5 1.30(2) . ?
C6 C8 1.532(16) . ?
C1 C1 1.33(2) 2_676 ?
C1 C2 1.424(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C9 1.55(2) 2_457 ?
C2 C2 1.200(19) 2_776 ?
N1 C7 1.348(19) . ?
C5 C4 1.42(3) . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N2 C8 123.6(10) . . ?
C9 N2 H2 118.2 . . ?
C8 N2 H2 118.2 . . ?
C4 C3 N1 121.5(17) . . ?
C4 C3 H3 119.3 . . ?
N1 C3 H3 119.3 . . ?
C7 C6 C5 114.9(14) . . ?
C7 C6 C8 123.1(13) . . ?
C5 C6 C8 122.0(12) . . ?
C1 C1 C2 124.0(11) 2_676 . ?
C1 C1 I1 120.3(9) 2_676 . ?
C2 C1 I1 115.5(7) . . ?
N2 C8 C6 114.0(10) . . ?
N2 C8 H8A 108.8 . . ?
C6 C8 H8A 108.8 . . ?
N2 C8 H8B 108.8 . . ?
C6 C8 H8B 108.8 . . ?
H8A C8 H8B 107.6 . . ?
O1 C9 N2 124.9(10) . . ?
O1 C9 C9 122.9(12) . 2_457 ?
N2 C9 C9 112.2(13) . 2_457 ?
C2 C2 C1 176.5(14) 2_776 . ?
C3 N1 C7 117.7(13) . . ?
C6 C5 C4 121.1(16) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C6 C7 N1 125.9(16) . . ?
C6 C7 H7 117.1 . . ?
N1 C7 H7 117.1 . . ?
C3 C4 C5 119.0(19) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.511
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.156