# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_stu8016
_database_code_depnum_ccdc_archive 'CCDC 1526301'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 I2'
_chemical_formula_weight         462.09
_chemical_absolute_configuration ad


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   8.4867(2)
_cell_length_b                   11.5788(2)
_cell_length_c                   16.5698(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.762(4)
_cell_angle_gamma                90.00
_cell_volume                     1626.35(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4202
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    3.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4713
_exptl_absorpt_correction_T_max  0.6345
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13607
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         28.24
_reflns_number_total             6158
_reflns_number_gt                5928
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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. 

 One Iod-atom was disordered over two positions. Several restraints (SADI,
 SAME, ISOR and SIMU) were used in order to improve refinement stability.
;

_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)+(0.0260P)²+4.0991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.49(3)
_refine_ls_number_reflns         6158
_refine_ls_number_parameters     344
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1A I 0.97588(11) 0.15193(4) -0.61682(5) 0.04871(12) Uani 1 1 d . . .
C7A C 0.3498(8) 0.1818(6) -0.1860(4) 0.0411(15) Uani 1 1 d D . .
I2A I 0.2156(5) 0.1745(6) -0.0814(2) 0.0551(6) Uani 0.76(3) 1 d PDU A 1
I2C I 0.188(2) 0.204(2) -0.0945(12) 0.057(3) Uani 0.24(3) 1 d PDU A 2
C1A C 0.8270(7) 0.1585(6) -0.5196(4) 0.0362(13) Uani 1 1 d . . .
C2A C 0.8136(7) 0.2608(6) -0.4789(4) 0.0405(14) Uani 1 1 d . . .
H2A H 0.8697 0.3262 -0.4950 0.049 Uiso 1 1 calc R . .
C3A C 0.7163(8) 0.2676(6) -0.4132(4) 0.0416(14) Uani 1 1 d . . .
C4A C 0.6347(7) 0.1688(5) -0.3907(3) 0.0342(13) Uani 1 1 d . . .
C5A C 0.6463(7) 0.0665(5) -0.4332(3) 0.0325(11) Uani 1 1 d . . .
C6A C 0.7452(7) 0.0611(5) -0.4984(3) 0.0328(12) Uani 1 1 d . . .
H6A H 0.7556 -0.0081 -0.5274 0.039 Uiso 1 1 calc R . .
C8A C 0.5080(8) 0.1657(6) -0.1750(4) 0.0426(15) Uani 1 1 d . A .
H8A H 0.5536 0.1579 -0.1224 0.051 Uiso 1 1 calc R . .
C9A C 0.6037(8) 0.1608(6) -0.2417(4) 0.0402(14) Uani 1 1 d . . .
C10A C 0.5331(8) 0.1744(5) -0.3187(4) 0.0377(13) Uani 1 1 d . A .
C11A C 0.3703(7) 0.1936(6) -0.3297(4) 0.0384(13) Uani 1 1 d . . .
C12A C 0.2790(7) 0.1956(6) -0.2617(4) 0.0424(14) Uani 1 1 d . A .
H12A H 0.1693 0.2064 -0.2677 0.051 Uiso 1 1 calc R . .
C13A C 0.7040(12) 0.3809(7) -0.3687(6) 0.068(2) Uani 1 1 d . . .
H13A H 0.7740 0.4371 -0.3916 0.101 Uiso 1 1 calc R . .
H13B H 0.7338 0.3695 -0.3120 0.101 Uiso 1 1 calc R . .
H13C H 0.5962 0.4089 -0.3740 0.101 Uiso 1 1 calc R . .
C14A C 0.5590(8) -0.0407(6) -0.4090(4) 0.0459(15) Uani 1 1 d . . .
H14A H 0.4483 -0.0225 -0.4042 0.069 Uiso 1 1 calc R . .
H14B H 0.6030 -0.0686 -0.3575 0.069 Uiso 1 1 calc R . .
H14C H 0.5695 -0.1000 -0.4498 0.069 Uiso 1 1 calc R . .
C15A C 0.7796(8) 0.1414(8) -0.2267(4) 0.056(2) Uani 1 1 d . A .
H15A H 0.8367 0.2085 -0.2448 0.083 Uiso 1 1 calc R . .
H15B H 0.8116 0.0738 -0.2564 0.083 Uiso 1 1 calc R . .
H15C H 0.8028 0.1296 -0.1695 0.083 Uiso 1 1 calc R . .
C16A C 0.2934(9) 0.2136(8) -0.4128(4) 0.0545(18) Uani 1 1 d . A .
H16A H 0.1859 0.2400 -0.4075 0.082 Uiso 1 1 calc R . .
H16B H 0.2927 0.1420 -0.4431 0.082 Uiso 1 1 calc R . .
H16C H 0.3524 0.2716 -0.4409 0.082 Uiso 1 1 calc R . .
I1B I 1.80304(12) 0.66807(5) -0.50668(5) 0.05532(13) Uani 1 1 d . . .
I2B I 1.02049(11) 0.07624(4) -0.88379(5) 0.04529(11) Uani 1 1 d . . .
C1B C 1.6622(8) 0.5548(6) -0.5775(4) 0.0401(14) Uani 1 1 d . . .
C2B C 1.5077(8) 0.5407(6) -0.5589(5) 0.0468(15) Uani 1 1 d . . .
H2B H 1.4692 0.5804 -0.5145 0.056 Uiso 1 1 calc R . .
C3B C 1.4073(8) 0.4690(6) -0.6044(4) 0.0412(13) Uani 1 1 d . . .
C4B C 1.4678(7) 0.4099(6) -0.6696(4) 0.0379(13) Uani 1 1 d . . .
C5B C 1.6273(8) 0.4218(6) -0.6882(4) 0.0412(14) Uani 1 1 d . . .
C6B C 1.7216(7) 0.4978(6) -0.6404(4) 0.0428(14) Uani 1 1 d . . .
H6B H 1.8276 0.5091 -0.6525 0.051 Uiso 1 1 calc R . .
C7B C 1.1730(7) 0.1863(6) -0.8150(3) 0.0352(12) Uani 1 1 d . . .
C8B C 1.2677(7) 0.1393(6) -0.7527(4) 0.0348(12) Uani 1 1 d . . .
H8B H 1.2668 0.0593 -0.7429 0.042 Uiso 1 1 calc R . .
C9B C 1.3638(7) 0.2119(5) -0.7048(3) 0.0342(12) Uani 1 1 d . . .
C10B C 1.3624(7) 0.3312(6) -0.7203(4) 0.0358(13) Uani 1 1 d . . .
C11B C 1.2674(9) 0.3757(6) -0.7837(4) 0.0454(15) Uani 1 1 d . . .
C12B C 1.1724(8) 0.3022(6) -0.8306(4) 0.0446(15) Uani 1 1 d . . .
H12B H 1.1074 0.3320 -0.8731 0.054 Uiso 1 1 calc R . .
C13B C 1.2377(8) 0.4551(7) -0.5832(6) 0.058(2) Uani 1 1 d . . .
H13D H 1.2153 0.3740 -0.5747 0.087 Uiso 1 1 calc R . .
H13E H 1.1691 0.4845 -0.6271 0.087 Uiso 1 1 calc R . .
H13F H 1.2194 0.4980 -0.5343 0.087 Uiso 1 1 calc R . .
C14B C 1.6911(9) 0.3574(7) -0.7589(5) 0.0517(17) Uani 1 1 d . . .
H14D H 1.6281 0.3757 -0.8076 0.078 Uiso 1 1 calc R . .
H14E H 1.6866 0.2750 -0.7488 0.078 Uiso 1 1 calc R . .
H14F H 1.7997 0.3802 -0.7656 0.078 Uiso 1 1 calc R . .
C15B C 1.4648(8) 0.1600(6) -0.6373(4) 0.0448(15) Uani 1 1 d . . .
H15D H 1.5710 0.1487 -0.6550 0.067 Uiso 1 1 calc R . .
H15E H 1.4209 0.0863 -0.6221 0.067 Uiso 1 1 calc R . .
H15F H 1.4677 0.2116 -0.5911 0.067 Uiso 1 1 calc R . .
C16B C 1.2633(12) 0.5045(7) -0.8023(6) 0.074(3) Uani 1 1 d . . .
H16D H 1.2005 0.5178 -0.8519 0.110 Uiso 1 1 calc R . .
H16E H 1.3699 0.5321 -0.8086 0.110 Uiso 1 1 calc R . .
H16F H 1.2170 0.5455 -0.7582 0.110 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1A C1A 2.095(6) . ?
C7A C8A 1.359(10) . ?
C7A C12A 1.374(10) . ?
C7A I2C 2.111(9) . ?
C7A I2A 2.120(6) . ?
C1A C2A 1.371(9) . ?
C1A C6A 1.379(9) . ?
C2A C3A 1.399(9) . ?
C2A H2A 0.9400 . ?
C3A C4A 1.397(9) . ?
C3A C13A 1.511(10) . ?
C4A C5A 1.384(8) . ?
C4A C10A 1.507(7) . ?
C5A C6A 1.401(8) . ?
C5A C14A 1.510(9) . ?
C6A H6A 0.9400 . ?
C8A C9A 1.405(8) . ?
C8A H8A 0.9400 . ?
C9A C10A 1.392(9) . ?
C9A C15A 1.518(9) . ?
C10A C11A 1.402(9) . ?
C11A C12A 1.398(9) . ?
C11A C16A 1.512(9) . ?
C12A H12A 0.9400 . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C13A H13C 0.9700 . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C14A H14C 0.9700 . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C15A H15C 0.9700 . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C16A H16C 0.9700 . ?
I1B C1B 2.095(6) . ?
I2B C7B 2.111(6) . ?
C1B C6B 1.352(10) . ?
C1B C2B 1.371(9) . ?
C2B C3B 1.387(9) . ?
C2B H2B 0.9400 . ?
C3B C4B 1.397(9) . ?
C3B C13B 1.507(9) . ?
C4B C5B 1.410(9) . ?
C4B C10B 1.504(8) . ?
C5B C6B 1.407(9) . ?
C5B C14B 1.510(10) . ?
C6B H6B 0.9400 . ?
C7B C12B 1.366(9) . ?
C7B C8B 1.388(8) . ?
C8B C9B 1.392(8) . ?
C8B H8B 0.9400 . ?
C9B C10B 1.405(9) . ?
C9B C15B 1.502(8) . ?
C10B C11B 1.393(9) . ?
C11B C12B 1.384(9) . ?
C11B C16B 1.522(10) . ?
C12B H12B 0.9400 . ?
C13B H13D 0.9700 . ?
C13B H13E 0.9700 . ?
C13B H13F 0.9700 . ?
C14B H14D 0.9700 . ?
C14B H14E 0.9700 . ?
C14B H14F 0.9700 . ?
C15B H15D 0.9700 . ?
C15B H15E 0.9700 . ?
C15B H15F 0.9700 . ?
C16B H16D 0.9700 . ?
C16B H16E 0.9700 . ?
C16B H16F 0.9700 . ?

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
C8A C7A C12A 121.6(6) . . ?
C8A C7A I2C 126.5(9) . . ?
C12A C7A I2C 111.7(10) . . ?
C8A C7A I2A 116.8(5) . . ?
C12A C7A I2A 121.5(5) . . ?
I2C C7A I2A 12.6(8) . . ?
C2A C1A C6A 121.7(6) . . ?
C2A C1A I1A 118.5(5) . . ?
C6A C1A I1A 119.7(5) . . ?
C1A C2A C3A 119.9(6) . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A H2A 120.1 . . ?
C4A C3A C2A 118.7(6) . . ?
C4A C3A C13A 122.3(6) . . ?
C2A C3A C13A 119.1(6) . . ?
C5A C4A C3A 121.1(5) . . ?
C5A C4A C10A 119.8(5) . . ?
C3A C4A C10A 119.1(5) . . ?
C4A C5A C6A 119.4(5) . . ?
C4A C5A C14A 121.4(5) . . ?
C6A C5A C14A 119.2(6) . . ?
C1A C6A C5A 119.2(5) . . ?
C1A C6A H6A 120.4 . . ?
C5A C6A H6A 120.4 . . ?
C7A C8A C9A 120.3(6) . . ?
C7A C8A H8A 119.8 . . ?
C9A C8A H8A 119.8 . . ?
C10A C9A C8A 118.5(6) . . ?
C10A C9A C15A 122.9(6) . . ?
C8A C9A C15A 118.6(6) . . ?
C9A C10A C11A 121.0(6) . . ?
C9A C10A C4A 118.9(6) . . ?
C11A C10A C4A 120.1(5) . . ?
C12A C11A C10A 118.6(6) . . ?
C12A C11A C16A 120.0(6) . . ?
C10A C11A C16A 121.4(6) . . ?
C7A C12A C11A 120.0(6) . . ?
C7A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C3A C13A H13A 109.5 . . ?
C3A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C3A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C5A C14A H14A 109.5 . . ?
C5A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C5A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C9A C15A H15A 109.5 . . ?
C9A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C9A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C11A C16A H16A 109.5 . . ?
C11A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C11A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C6B C1B C2B 120.8(6) . . ?
C6B C1B I1B 120.9(5) . . ?
C2B C1B I1B 118.3(5) . . ?
C1B C2B C3B 121.2(7) . . ?
C1B C2B H2B 119.4 . . ?
C3B C2B H2B 119.4 . . ?
C2B C3B C4B 118.3(6) . . ?
C2B C3B C13B 120.4(7) . . ?
C4B C3B C13B 121.2(6) . . ?
C3B C4B C5B 120.9(6) . . ?
C3B C4B C10B 119.8(6) . . ?
C5B C4B C10B 119.3(6) . . ?
C6B C5B C4B 117.7(6) . . ?
C6B C5B C14B 122.0(6) . . ?
C4B C5B C14B 120.4(6) . . ?
C1B C6B C5B 121.1(6) . . ?
C1B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C12B C7B C8B 121.5(6) . . ?
C12B C7B I2B 119.6(4) . . ?
C8B C7B I2B 118.9(5) . . ?
C7B C8B C9B 119.3(6) . . ?
C7B C8B H8B 120.4 . . ?
C9B C8B H8B 120.4 . . ?
C8B C9B C10B 119.4(5) . . ?
C8B C9B C15B 118.7(6) . . ?
C10B C9B C15B 121.9(6) . . ?
C11B C10B C9B 120.1(6) . . ?
C11B C10B C4B 120.3(6) . . ?
C9B C10B C4B 119.6(5) . . ?
C12B C11B C10B 119.7(6) . . ?
C12B C11B C16B 118.8(6) . . ?
C10B C11B C16B 121.4(6) . . ?
C7B C12B C11B 120.1(6) . . ?
C7B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C3B C13B H13D 109.5 . . ?
C3B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C3B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C5B C14B H14D 109.5 . . ?
C5B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C5B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C9B C15B H15D 109.5 . . ?
C9B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C9B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C11B C16B H16D 109.5 . . ?
C11B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C11B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A C3A 0.8(10) . . . . ?
I1A C1A C2A C3A -179.4(5) . . . . ?
C1A C2A C3A C4A 0.1(10) . . . . ?
C1A C2A C3A C13A 179.6(7) . . . . ?
C2A C3A C4A C5A -1.4(10) . . . . ?
C13A C3A C4A C5A 179.1(7) . . . . ?
C2A C3A C4A C10A 178.3(6) . . . . ?
C13A C3A C4A C10A -1.2(10) . . . . ?
C3A C4A C5A C6A 1.8(9) . . . . ?
C10A C4A C5A C6A -177.9(5) . . . . ?
C3A C4A C5A C14A 179.7(6) . . . . ?
C10A C4A C5A C14A 0.0(9) . . . . ?
C2A C1A C6A C5A -0.4(9) . . . . ?
I1A C1A C6A C5A 179.8(4) . . . . ?
C4A C5A C6A C1A -0.9(8) . . . . ?
C14A C5A C6A C1A -178.9(6) . . . . ?
C12A C7A C8A C9A -1.1(11) . . . . ?
I2C C7A C8A C9A -175.2(10) . . . . ?
I2A C7A C8A C9A 175.3(5) . . . . ?
C7A C8A C9A C10A 0.9(10) . . . . ?
C7A C8A C9A C15A -179.3(7) . . . . ?
C8A C9A C10A C11A 0.5(10) . . . . ?
C15A C9A C10A C11A -179.2(7) . . . . ?
C8A C9A C10A C4A -179.8(6) . . . . ?
C15A C9A C10A C4A 0.5(10) . . . . ?
C5A C4A C10A C9A 96.9(7) . . . . ?
C3A C4A C10A C9A -82.9(8) . . . . ?
C5A C4A C10A C11A -83.4(8) . . . . ?
C3A C4A C10A C11A 96.8(7) . . . . ?
C9A C10A C11A C12A -1.8(10) . . . . ?
C4A C10A C11A C12A 178.5(6) . . . . ?
C9A C10A C11A C16A 177.3(7) . . . . ?
C4A C10A C11A C16A -2.4(10) . . . . ?
C8A C7A C12A C11A -0.1(11) . . . . ?
I2C C7A C12A C11A 174.7(8) . . . . ?
I2A C7A C12A C11A -176.4(5) . . . . ?
C10A C11A C12A C7A 1.6(10) . . . . ?
C16A C11A C12A C7A -177.5(7) . . . . ?
C6B C1B C2B C3B -0.9(11) . . . . ?
I1B C1B C2B C3B 178.6(5) . . . . ?
C1B C2B C3B C4B 0.8(10) . . . . ?
C1B C2B C3B C13B -179.7(7) . . . . ?
C2B C3B C4B C5B 0.6(10) . . . . ?
C13B C3B C4B C5B -178.9(7) . . . . ?
C2B C3B C4B C10B 180.0(6) . . . . ?
C13B C3B C4B C10B 0.4(10) . . . . ?
C3B C4B C5B C6B -1.9(10) . . . . ?
C10B C4B C5B C6B 178.8(6) . . . . ?
C3B C4B C5B C14B -180.0(6) . . . . ?
C10B C4B C5B C14B 0.7(9) . . . . ?
C2B C1B C6B C5B -0.5(10) . . . . ?
I1B C1B C6B C5B -179.9(5) . . . . ?
C4B C5B C6B C1B 1.8(10) . . . . ?
C14B C5B C6B C1B 179.9(6) . . . . ?
C12B C7B C8B C9B 0.2(9) . . . . ?
I2B C7B C8B C9B -177.3(4) . . . . ?
C7B C8B C9B C10B 0.4(9) . . . . ?
C7B C8B C9B C15B 179.6(6) . . . . ?
C8B C9B C10B C11B -1.0(9) . . . . ?
C15B C9B C10B C11B 179.8(6) . . . . ?
C8B C9B C10B C4B -179.1(5) . . . . ?
C15B C9B C10B C4B 1.7(9) . . . . ?
C3B C4B C10B C11B 84.7(8) . . . . ?
C5B C4B C10B C11B -96.0(8) . . . . ?
C3B C4B C10B C9B -97.3(7) . . . . ?
C5B C4B C10B C9B 82.0(8) . . . . ?
C9B C10B C11B C12B 1.1(10) . . . . ?
C4B C10B C11B C12B 179.2(6) . . . . ?
C9B C10B C11B C16B -179.8(7) . . . . ?
C4B C10B C11B C16B -1.8(11) . . . . ?
C8B C7B C12B C11B -0.1(10) . . . . ?
I2B C7B C12B C11B 177.4(5) . . . . ?
C10B C11B C12B C7B -0.6(11) . . . . ?
C16B C11B C12B C7B -179.7(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.108
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_stu8104
_database_code_depnum_ccdc_archive 'CCDC 1526302'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 I2'
_chemical_formula_weight         460.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   11.4988(3)
_cell_length_b                   15.9491(3)
_cell_length_c                   8.2449(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.9060(10)
_cell_angle_gamma                90.00
_cell_volume                     1497.71(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3511
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    4.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4095
_exptl_absorpt_correction_T_max  0.8848
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11238
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         28.55
_reflns_number_total             3703
_reflns_number_gt                3202
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.

 One I atom is disordered over two positions. Several restraints (SADI,
 SAME, ISOR and SIMU) were used in order to improve refinement stability.
;

_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)+(0.0323P)²+5.3086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     173
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.45780(3) 0.29641(2) 0.34239(4) 0.05025(11) Uani 1 1 d U . .
C10 C -0.2092(4) 0.5821(3) 1.2860(5) 0.0362(9) Uani 1 1 d D . .
I2 I -0.1542(5) 0.6390(3) 1.5172(6) 0.0489(5) Uani 0.62(5) 1 d PDU A 1
I2A I -0.1608(10) 0.6505(13) 1.497(2) 0.0566(16) Uani 0.38(5) 1 d PDU A 2
C1 C -0.3979(4) 0.3705(3) 0.5475(5) 0.0345(8) Uani 1 1 d . . .
C2 C -0.2790(4) 0.3729(3) 0.6020(5) 0.0346(8) Uani 1 1 d . . .
H2 H -0.2265 0.3445 0.5432 0.042 Uiso 1 1 calc R . .
C3 C -0.2359(3) 0.4170(3) 0.7439(5) 0.0319(8) Uani 1 1 d . . .
C4 C -0.3151(3) 0.4572(3) 0.8327(5) 0.0324(8) Uani 1 1 d . . .
C5 C -0.4355(4) 0.4563(3) 0.7706(5) 0.0383(9) Uani 1 1 d . . .
H5 H -0.4887 0.4854 0.8269 0.046 Uiso 1 1 calc R . .
C6 C -0.4770(4) 0.4136(3) 0.6282(5) 0.0385(9) Uani 1 1 d . . .
H6 H -0.5575 0.4138 0.5873 0.046 Uiso 1 1 calc R . .
C7 C -0.2762(3) 0.4995(3) 0.9914(5) 0.0330(8) Uani 1 1 d . A .
C8 C -0.2160(3) 0.4559(3) 1.1242(5) 0.0319(8) Uani 1 1 d . . .
C9 C -0.1834(4) 0.4986(3) 1.2715(5) 0.0358(8) Uani 1 1 d . A .
H9 H -0.1432 0.4698 1.3617 0.043 Uiso 1 1 calc R . .
C11 C -0.2688(4) 0.6265(3) 1.1558(6) 0.0413(10) Uani 1 1 d . A .
H11 H -0.2861 0.6837 1.1662 0.050 Uiso 1 1 calc R . .
C12 C -0.3021(4) 0.5844(3) 1.0096(6) 0.0387(9) Uani 1 1 d . . .
H12 H -0.3432 0.6136 0.9206 0.046 Uiso 1 1 calc R A .
C13 C -0.1040(3) 0.4189(3) 0.7945(5) 0.0364(9) Uani 1 1 d . . .
H13A H -0.0837 0.4691 0.8609 0.044 Uiso 1 1 calc R . .
H13B H -0.0655 0.4234 0.6959 0.044 Uiso 1 1 calc R . .
C14 C -0.0558(4) 0.3421(3) 0.8915(5) 0.0382(9) Uani 1 1 d . A .
H14A H 0.0267 0.3349 0.8767 0.046 Uiso 1 1 calc R . .
H14B H -0.0986 0.2925 0.8453 0.046 Uiso 1 1 calc R . .
C15 C -0.0636(4) 0.3452(3) 1.0749(5) 0.0372(9) Uani 1 1 d . . .
H15A H -0.0097 0.3886 1.1247 0.045 Uiso 1 1 calc R A .
H15B H -0.0366 0.2914 1.1236 0.045 Uiso 1 1 calc R . .
C16 C -0.1863(4) 0.3633(3) 1.1187(5) 0.0372(9) Uani 1 1 d . A .
H16A H -0.2445 0.3358 1.0380 0.045 Uiso 1 1 calc R . .
H16B H -0.1926 0.3385 1.2259 0.045 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.100(4) . ?
C10 C9 1.374(6) . ?
C10 C11 1.386(6) . ?
C10 I2A 2.064(9) . ?
C10 I2 2.127(6) . ?
C1 C2 1.380(6) . ?
C1 C6 1.382(6) . ?
C2 C3 1.397(6) . ?
C2 H2 0.9400 . ?
C3 C4 1.400(6) . ?
C3 C13 1.517(5) . ?
C4 C5 1.408(6) . ?
C4 C7 1.486(6) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.397(6) . ?
C7 C12 1.399(6) . ?
C8 C9 1.398(6) . ?
C8 C16 1.518(6) . ?
C9 H9 0.9400 . ?
C11 C12 1.387(6) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.525(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.528(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.532(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?

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 C10 C11 121.1(4) . . ?
C9 C10 I2A 123.3(8) . . ?
C11 C10 I2A 115.5(8) . . ?
C9 C10 I2 116.8(4) . . ?
C11 C10 I2 122.1(4) . . ?
I2A C10 I2 6.7(7) . . ?
C2 C1 C6 121.2(4) . . ?
C2 C1 I1 118.6(3) . . ?
C6 C1 I1 120.2(3) . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 C13 117.8(4) . . ?
C4 C3 C13 123.0(4) . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 C7 122.0(4) . . ?
C5 C4 C7 119.1(4) . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 118.7(4) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C12 119.2(4) . . ?
C8 C7 C4 121.4(4) . . ?
C12 C7 C4 119.4(4) . . ?
C7 C8 C9 118.9(4) . . ?
C7 C8 C16 123.4(4) . . ?
C9 C8 C16 117.7(4) . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C10 C11 C12 118.3(4) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C7 121.6(4) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
C3 C13 C14 113.9(3) . . ?
C3 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C3 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 115.2(4) . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 C16 114.9(4) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C8 C16 C15 114.1(3) . . ?
C8 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C8 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.0(7) . . . . ?
I1 C1 C2 C3 -175.9(3) . . . . ?
C1 C2 C3 C4 1.6(6) . . . . ?
C1 C2 C3 C13 -178.4(4) . . . . ?
C2 C3 C4 C5 -4.0(6) . . . . ?
C13 C3 C4 C5 176.1(4) . . . . ?
C2 C3 C4 C7 175.1(4) . . . . ?
C13 C3 C4 C7 -4.9(6) . . . . ?
C3 C4 C5 C6 2.9(6) . . . . ?
C7 C4 C5 C6 -176.1(4) . . . . ?
C2 C1 C6 C5 -3.0(7) . . . . ?
I1 C1 C6 C5 174.8(3) . . . . ?
C4 C5 C6 C1 0.6(7) . . . . ?
C3 C4 C7 C8 -58.2(6) . . . . ?
C5 C4 C7 C8 120.9(4) . . . . ?
C3 C4 C7 C12 123.0(4) . . . . ?
C5 C4 C7 C12 -57.9(5) . . . . ?
C12 C7 C8 C9 0.0(6) . . . . ?
C4 C7 C8 C9 -178.8(4) . . . . ?
C12 C7 C8 C16 178.4(4) . . . . ?
C4 C7 C8 C16 -0.4(6) . . . . ?
C11 C10 C9 C8 0.3(6) . . . . ?
I2A C10 C9 C8 -178.5(4) . . . . ?
I2 C10 C9 C8 -180.0(3) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C16 C8 C9 C10 -178.9(4) . . . . ?
C9 C10 C11 C12 0.1(7) . . . . ?
I2A C10 C11 C12 179.0(4) . . . . ?
I2 C10 C11 C12 -179.6(4) . . . . ?
C10 C11 C12 C7 -0.5(7) . . . . ?
C8 C7 C12 C11 0.5(6) . . . . ?
C4 C7 C12 C11 179.3(4) . . . . ?
C2 C3 C13 C14 -83.4(5) . . . . ?
C4 C3 C13 C14 96.6(5) . . . . ?
C3 C13 C14 C15 -83.6(5) . . . . ?
C13 C14 C15 C16 53.6(5) . . . . ?
C7 C8 C16 C15 94.4(5) . . . . ?
C9 C8 C16 C15 -87.2(5) . . . . ?
C14 C15 C16 C8 -85.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        28.55
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.113
#=============================================================================
#  end of cif data for "stu8104" (compound 10j) 
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
