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

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

data_se100896
_database_code_depnum_ccdc_archive 'CCDC 1510562'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H8 I2'
_chemical_formula_sum            'C8 H8 I2'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      213(1)
_chemical_formula_weight         357.94

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.8117(9)
_cell_length_b                   7.4263(8)
_cell_length_c                   14.7072(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     962.41(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(1)
_cell_measurement_reflns_used    5500
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      28.14
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    6.466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1404
_exptl_absorpt_correction_T_max  0.5641
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
Crystal decay was monitored by repeating the initial 50 frames
at the end of the data collection and analyzing duplicate
reflections
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6219
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.743
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2159
_reflns_number_gt                2132
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;

_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)+(0.0526P)²+0.5429P] 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, 1133 Friedel Pairs.
;
_refine_ls_abs_structure_Flack   0.26(5)
_refine_ls_number_reflns         2159
_refine_ls_number_parameters     94
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.090
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4817(8) 0.4573(9) 0.4579(5) 0.0309(15) Uani 1 1 d . . . . .
C2 C 0.3998(8) 0.5636(11) 0.5185(6) 0.0326(17) Uani 1 1 d . . . . .
H2 H 0.4044 0.6891 0.5110 0.039 Uiso 1 1 calc R U . . .
C3 C 0.3127(8) 0.4978(10) 0.5887(6) 0.0305(14) Uani 1 1 d . . . . .
C4 C 0.3073(9) 0.3108(9) 0.5979(7) 0.0314(17) Uani 1 1 d . . . . .
C5 C 0.3887(9) 0.1975(10) 0.5413(6) 0.0310(15) Uani 1 1 d . . . . .
H5 H 0.3844 0.0721 0.5496 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4760(8) 0.2697(10) 0.4727(6) 0.0301(14) Uani 1 1 d . . . . .
C7 C 0.5679(11) 0.5430(13) 0.3807(8) 0.046(2) Uani 1 1 d . . . . .
H7A H 0.5385 0.6684 0.3753 0.070 Uiso 1 1 calc R U . . .
H7B H 0.5446 0.4805 0.3245 0.070 Uiso 1 1 calc R U . . .
H7C H 0.6759 0.5353 0.3926 0.070 Uiso 1 1 calc R U . . .
C8 C 0.2297(10) 0.6247(11) 0.6516(7) 0.0398(18) Uani 1 1 d . . . . .
H8A H 0.2356 0.7463 0.6277 0.060 Uiso 1 1 calc R U . . .
H8B H 0.2759 0.6208 0.7114 0.060 Uiso 1 1 calc R U . . .
H8C H 0.1241 0.5886 0.6560 0.060 Uiso 1 1 calc R U . . .
I1 I 0.17074(5) 0.19069(7) 0.69869(5) 0.04150(18) Uani 1 1 d . . . . .
I2 I 0.60230(5) 0.09254(6) 0.39179(5) 0.03999(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(12) . ?
C1 C6 1.411(9) . ?
C1 C7 1.507(12) . ?
C2 C3 1.375(12) . ?
C2 H2 0.9400 . ?
C3 C4 1.397(10) . ?
C3 C8 1.510(11) . ?
C4 C5 1.384(12) . ?
C4 I1 2.107(9) . ?
C5 C6 1.377(12) . ?
C5 H5 0.9400 . ?
C6 I2 2.094(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 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
C2 C1 C6 116.2(7) . . ?
C2 C1 C7 120.3(7) . . ?
C6 C1 C7 123.5(7) . . ?
C3 C2 C1 124.7(7) . . ?
C3 C2 H2 117.7 . . ?
C1 C2 H2 117.7 . . ?
C2 C3 C4 116.4(8) . . ?
C2 C3 C8 120.6(7) . . ?
C4 C3 C8 123.0(8) . . ?
C5 C4 C3 121.9(8) . . ?
C5 C4 I1 117.5(5) . . ?
C3 C4 I1 120.6(6) . . ?
C6 C5 C4 119.6(7) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 121.1(7) . . ?
C5 C6 I2 118.0(5) . . ?
C1 C6 I2 120.9(6) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.971
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.171

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_se150755
_database_code_depnum_ccdc_archive 'CCDC 1510564'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H8 I2'
_chemical_formula_sum            'C8 H8 I2'
_exptl_crystal_recrystallization_method EtOH/H2O
_chemical_melting_point          ?

_exptl_crystal_description       Rhombus
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      198(2)
_chemical_formula_weight         357.94

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.572(5)
_cell_length_b                   8.414(5)
_cell_length_c                   11.973(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.341(8)
_cell_angle_gamma                90.00
_cell_volume                     929.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    198(2)
_cell_measurement_reflns_used    2410
_cell_measurement_theta_min      3.273
_cell_measurement_theta_max      28.222
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    6.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0977
_exptl_absorpt_correction_T_max  0.2029
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
Crystal decay was monitored by repeating the initial 50 frames
at the end of the data collection and analyzing duplicate
reflections
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2976
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_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         3.276
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1036
_reflns_number_gt                941
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'

_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)+(0.0317P)²+1.0768P] 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     SHELXL
_refine_ls_extinction_coef       0.0207(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1036
_refine_ls_number_parameters     48
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_restrained_S_all      1.241
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.27160(3) 0.99659(2) 0.27165(2) 0.0299(2) Uani 1 1 d . . . . .
C1 C 0.2625(3) 0.8449(3) 0.4099(2) 0.0243(6) Uani 1 1 d . . . . .
C2 C 0.1299(3) 0.8311(3) 0.4371(3) 0.0257(6) Uani 1 1 d . . . . .
H2 H 0.0486 0.8880 0.3924 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3860(3) 0.7638(3) 0.4721(2) 0.0251(6) Uani 1 1 d . . . . .
C4 C 0.5300(3) 0.7742(4) 0.4445(3) 0.0318(7) Uani 1 1 d . . . . .
H4A H 0.5192 0.7401 0.3644 0.048 Uiso 1 1 calc R U . . .
H4B H 0.5998 0.7051 0.4971 0.048 Uiso 1 1 calc R U . . .
H4C H 0.5648 0.8842 0.4539 0.048 Uiso 1 1 calc R U . . .


_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 2.110(3) . ?
C1 C2 1.395(4) . ?
C1 C3 1.397(4) . ?
C2 C3 1.390(4) 7_566 ?
C2 H2 0.9500 . ?
C3 C2 1.390(4) 7_566 ?
C3 C4 1.502(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 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
C2 C1 C3 121.9(3) . . ?
C2 C1 I1 117.5(2) . . ?
C3 C1 I1 120.6(2) . . ?
C3 C2 C1 121.7(3) 7_566 . ?
C3 C2 H2 119.2 7_566 . ?
C1 C2 H2 119.2 . . ?
C2 C3 C1 116.4(3) 7_566 . ?
C2 C3 C4 120.2(2) 7_566 . ?
C1 C3 C4 123.4(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_refine_diff_density_max         1.390
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.222

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_se151077
_database_code_depnum_ccdc_archive 'CCDC 1510565'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H8 I2'
_chemical_formula_sum            'C8 H8 I2'
_exptl_crystal_recrystallization_method EtOH
_chemical_melting_point          ?

_exptl_crystal_description       parallelpiped
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      213(2)
_chemical_formula_weight         357.94

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.2216(7)
_cell_length_b                   22.988(2)
_cell_length_c                   17.6581(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.2350(10)
_cell_angle_gamma                90.00
_cell_volume                     2875.3(5)
_cell_formula_units_Z            12
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    5938
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.37
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1944
_exptl_absorpt_coefficient_mu    6.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1397
_exptl_absorpt_correction_T_max  0.2096
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
Crystal decay was monitored by repeating the initial 50 frames
at the end of the data collection and analyzing duplicate
reflections
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19591
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.472
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6346
_reflns_number_gt                5518
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'

_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)+(0.0246P)²+3.5687P] 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     SHELXL
_refine_ls_extinction_coef       0.01173(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6346
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7009(5) 0.1794(2) 0.6730(2) 0.0421(9) Uani 1 1 d . . . . .
C2 C 0.6592(5) 0.17202(17) 0.5932(2) 0.0345(8) Uani 1 1 d . . . . .
C3 C 0.6300(5) 0.21995(17) 0.5435(2) 0.0345(8) Uani 1 1 d . . . . .
C4 C 0.6391(5) 0.27637(17) 0.5722(3) 0.0396(9) Uani 1 1 d . . . . .
C5 C 0.6784(6) 0.28339(19) 0.6518(3) 0.0477(11) Uani 1 1 d . . . . .
H5 H 0.6838 0.3211 0.6727 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7095(5) 0.2364(2) 0.7004(3) 0.0485(10) Uani 1 1 d . . . . .
H6 H 0.7376 0.2428 0.7540 0.058 Uiso 1 1 calc R U . . .
C7 C 0.7369(7) 0.1296(3) 0.7293(3) 0.0612(13) Uani 1 1 d . . . . .
H7A H 0.7896 0.1444 0.7804 0.092 Uiso 1 1 calc R U . . .
H7B H 0.8251 0.1026 0.7133 0.092 Uiso 1 1 calc R U . . .
H7C H 0.6190 0.1097 0.7304 0.092 Uiso 1 1 calc R U . . .
C8 C 0.6107(6) 0.3297(2) 0.5209(3) 0.0571(12) Uani 1 1 d . . . . .
H8A H 0.7087 0.3312 0.4904 0.086 Uiso 1 1 calc R U . . .
H8B H 0.6169 0.3643 0.5526 0.086 Uiso 1 1 calc R U . . .
H8C H 0.4881 0.3276 0.4867 0.086 Uiso 1 1 calc R U . . .
C9 C 0.1025(5) 0.27856(16) 0.4928(2) 0.0326(8) Uani 1 1 d . . . . .
C10 C 0.1346(4) 0.31240(15) 0.5595(2) 0.0289(7) Uani 1 1 d . . . . .
C11 C 0.1735(4) 0.28686(15) 0.6324(2) 0.0280(7) Uani 1 1 d . . . . .
C12 C 0.1777(5) 0.22650(16) 0.6414(2) 0.0330(8) Uani 1 1 d . . . . .
C13 C 0.1439(5) 0.19295(16) 0.5742(2) 0.0374(8) Uani 1 1 d . . . . .
H13 H 0.1460 0.1522 0.5781 0.045 Uiso 1 1 calc R U . . .
C14 C 0.1078(5) 0.21832(17) 0.5025(2) 0.0371(8) Uani 1 1 d . . . . .
H14 H 0.0859 0.1944 0.4586 0.044 Uiso 1 1 calc R U . . .
C15 C 0.0626(6) 0.3033(2) 0.4127(2) 0.0490(10) Uani 1 1 d . . . . .
H15A H -0.0556 0.3246 0.4046 0.074 Uiso 1 1 calc R U . . .
H15B H 0.0535 0.2720 0.3754 0.074 Uiso 1 1 calc R U . . .
H15C H 0.1640 0.3294 0.4064 0.074 Uiso 1 1 calc R U . . .
C16 C 0.2183(6) 0.1961(2) 0.7183(3) 0.0505(11) Uani 1 1 d . . . . .
H16A H 0.3451 0.2056 0.7450 0.076 Uiso 1 1 calc R U . . .
H16B H 0.2079 0.1544 0.7104 0.076 Uiso 1 1 calc R U . . .
H16C H 0.1282 0.2086 0.7491 0.076 Uiso 1 1 calc R U . . .
C17 C 0.6169(6) 0.48315(17) 0.6846(2) 0.0400(9) Uani 1 1 d . . . . .
C18 C 0.4657(5) 0.50095(14) 0.7178(2) 0.0334(8) Uani 1 1 d . . . . .
C19 C 0.4529(5) 0.48529(15) 0.7923(2) 0.0321(7) Uani 1 1 d . . . . .
C20 C 0.5913(5) 0.45035(16) 0.8368(2) 0.0369(8) Uani 1 1 d . . . . .
C21 C 0.7389(5) 0.43261(18) 0.8034(3) 0.0449(10) Uani 1 1 d . . . . .
H21 H 0.8336 0.4089 0.8319 0.054 Uiso 1 1 calc R U . . .
C22 C 0.7520(6) 0.44871(19) 0.7293(3) 0.0455(10) Uani 1 1 d . . . . .
H22 H 0.8555 0.4359 0.7088 0.055 Uiso 1 1 calc R U . . .
C23 C 0.6408(8) 0.4997(2) 0.6044(3) 0.0602(12) Uani 1 1 d . . . . .
H23A H 0.6501 0.5417 0.6009 0.090 Uiso 1 1 calc R U . . .
H23B H 0.5327 0.4862 0.5670 0.090 Uiso 1 1 calc R U . . .
H23C H 0.7548 0.4820 0.5937 0.090 Uiso 1 1 calc R U . . .
C24 C 0.5845(6) 0.4326(2) 0.9182(3) 0.0510(11) Uani 1 1 d . . . . .
H24A H 0.6925 0.4082 0.9383 0.076 Uiso 1 1 calc R U . . .
H24B H 0.4691 0.4111 0.9186 0.076 Uiso 1 1 calc R U . . .
H24C H 0.5875 0.4670 0.9502 0.076 Uiso 1 1 calc R U . . .
I1 I 0.64989(5) 0.08643(2) 0.55035(2) 0.05674(10) Uani 1 1 d . . . . .
I2 I 0.57759(4) 0.20849(2) 0.42296(2) 0.05279(10) Uani 1 1 d . . . . .
I3 I 0.12556(4) 0.40357(2) 0.54743(2) 0.04853(10) Uani 1 1 d . . . . .
I4 I 0.23041(4) 0.33792(2) 0.73309(2) 0.05266(10) Uani 1 1 d . . . . .
I5 I 0.25661(4) 0.55272(2) 0.64844(2) 0.04961(10) Uani 1 1 d . . . . .
I6 I 0.22878(4) 0.51404(2) 0.84347(2) 0.04888(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(5) . ?
C1 C6 1.395(7) . ?
C1 C7 1.505(6) . ?
C2 C3 1.399(5) . ?
C2 I1 2.104(4) . ?
C3 C4 1.390(6) . ?
C3 I2 2.104(4) . ?
C4 C5 1.388(6) . ?
C4 C8 1.514(6) . ?
C5 C6 1.371(7) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 C10 1.393(5) . ?
C9 C14 1.395(5) . ?
C9 C15 1.499(5) . ?
C10 C11 1.392(5) . ?
C10 I3 2.106(3) . ?
C11 C12 1.396(5) . ?
C11 I4 2.103(3) . ?
C12 C13 1.397(6) . ?
C12 C16 1.505(5) . ?
C13 C14 1.371(6) . ?
C13 H13 0.9400 . ?
C14 H14 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C22 1.378(6) . ?
C17 C18 1.397(5) . ?
C17 C23 1.510(6) . ?
C18 C19 1.385(5) . ?
C18 I5 2.115(3) . ?
C19 C20 1.398(5) . ?
C19 I6 2.108(4) . ?
C20 C21 1.376(6) . ?
C20 C24 1.504(6) . ?
C21 C22 1.382(6) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 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
C2 C1 C6 116.8(4) . . ?
C2 C1 C7 123.5(4) . . ?
C6 C1 C7 119.7(4) . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 I1 117.5(3) . . ?
C3 C2 I1 121.4(3) . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 I2 118.2(3) . . ?
C2 C3 I2 120.7(3) . . ?
C5 C4 C3 117.6(4) . . ?
C5 C4 C8 119.3(4) . . ?
C3 C4 C8 123.1(4) . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 122.2(4) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 117.0(3) . . ?
C10 C9 C15 123.7(4) . . ?
C14 C9 C15 119.3(4) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 I3 120.6(3) . . ?
C9 C10 I3 118.2(3) . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 I4 121.1(2) . . ?
C12 C11 I4 117.5(3) . . ?
C11 C12 C13 117.1(3) . . ?
C11 C12 C16 124.1(4) . . ?
C13 C12 C16 118.8(4) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C9 122.1(4) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 116.9(4) . . ?
C22 C17 C23 119.0(4) . . ?
C18 C17 C23 124.1(4) . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 I5 121.6(3) . . ?
C17 C18 I5 116.8(3) . . ?
C18 C19 C20 120.7(3) . . ?
C18 C19 I6 121.7(3) . . ?
C20 C19 I6 117.6(3) . . ?
C21 C20 C19 117.3(4) . . ?
C21 C20 C24 120.0(4) . . ?
C19 C20 C24 122.7(4) . . ?
C20 C21 C22 121.8(4) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C17 C22 C21 121.7(4) . . ?
C17 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         1.082
_refine_diff_density_min         -1.499
_refine_diff_density_rms         0.134

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_se151178
_database_code_depnum_ccdc_archive 'CCDC 1510566'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H8 I2'
_chemical_formula_sum            'C8 H8 I2'
_exptl_crystal_recrystallization_method C6H12/MeCN
_chemical_melting_point          ?

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         357.94

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.107(3)
_cell_length_b                   16.238(5)
_cell_length_c                   14.621(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.570(4)
_cell_angle_gamma                90.00
_cell_volume                     1920.8(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8662
_cell_measurement_theta_min      2.5085
_cell_measurement_theta_max      28.437
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    6.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0927
_exptl_absorpt_correction_T_max  0.4432
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
Crystal decay was monitored by repeating the initial 50 frames
at the end of the data collection and analyzing duplicate
reflections
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12928
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4294
_reflns_number_gt                3783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'

_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)+(0.0355P)²+0.3139P] 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         4294
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0687
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0140(4) 0.4725(2) 0.7330(2) 0.0300(7) Uani 1 1 d . . . . .
C2 C 0.0636(4) 0.4895(2) 0.8193(2) 0.0290(7) Uani 1 1 d . . . . .
C3 C 0.1289(4) 0.4296(2) 0.8786(2) 0.0297(7) Uani 1 1 d . . . . .
H3 H 0.1812 0.4451 0.9359 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1183(5) 0.3471(2) 0.8544(2) 0.0303(7) Uani 1 1 d . . . . .
C5 C 0.0398(5) 0.3272(2) 0.7694(2) 0.0319(8) Uani 1 1 d . . . . .
H5 H 0.0292 0.2712 0.7513 0.038 Uiso 1 1 calc R U . . .
C6 C -0.0222(4) 0.3883(2) 0.7120(2) 0.0303(8) Uani 1 1 d . . . . .
C7 C -0.0821(5) 0.5376(3) 0.6690(3) 0.0398(9) Uani 1 1 d . . . . .
H7A H -0.0474 0.5266 0.6072 0.060 Uiso 1 1 calc R U . . .
H7B H -0.0404 0.5915 0.6896 0.060 Uiso 1 1 calc R U . . .
H7C H -0.2031 0.5373 0.6683 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1854(5) 0.2817(3) 0.9183(3) 0.0391(9) Uani 1 1 d . . . . .
H8A H 0.2677 0.3059 0.9624 0.059 Uiso 1 1 calc R U . . .
H8B H 0.2375 0.2385 0.8832 0.059 Uiso 1 1 calc R U . . .
H8C H 0.0952 0.2579 0.9512 0.059 Uiso 1 1 calc R U . . .
C9 C 0.4996(4) 0.4382(2) 0.2302(2) 0.0295(7) Uani 1 1 d . . . . .
C10 C 0.4720(4) 0.5224(2) 0.2150(2) 0.0293(7) Uani 1 1 d . . . . .
C11 C 0.5183(4) 0.5829(2) 0.2780(2) 0.0317(8) Uani 1 1 d . . . . .
H11 H 0.4946 0.6390 0.2642 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5993(5) 0.5621(2) 0.3615(2) 0.0333(8) Uani 1 1 d . . . . .
C13 C 0.6318(5) 0.4793(2) 0.3794(2) 0.0327(8) Uani 1 1 d . . . . .
H13 H 0.6871 0.4634 0.4358 0.039 Uiso 1 1 calc R U . . .
C14 C 0.5834(4) 0.4194(2) 0.3148(2) 0.0299(7) Uani 1 1 d . . . . .
C15 C 0.4434(5) 0.3730(2) 0.1633(3) 0.0376(9) Uani 1 1 d . . . . .
H15A H 0.4500 0.3939 0.1008 0.056 Uiso 1 1 calc R U . . .
H15B H 0.3289 0.3579 0.1733 0.056 Uiso 1 1 calc R U . . .
H15C H 0.5144 0.3244 0.1720 0.056 Uiso 1 1 calc R U . . .
C16 C 0.6479(5) 0.6276(3) 0.4310(3) 0.0420(10) Uani 1 1 d . . . . .
H16A H 0.7226 0.6670 0.4041 0.063 Uiso 1 1 calc R U . . .
H16B H 0.7041 0.6019 0.4850 0.063 Uiso 1 1 calc R U . . .
H16C H 0.5488 0.6564 0.4489 0.063 Uiso 1 1 calc R U . . .
I1 I 0.07960(3) 0.61238(2) 0.86791(2) 0.03473(8) Uani 1 1 d . . . . .
I2 I -0.14134(3) 0.34820(2) 0.58672(2) 0.03748(8) Uani 1 1 d . . . . .
I3 I 0.34916(3) 0.56427(2) 0.09197(2) 0.03401(8) Uani 1 1 d . . . . .
I4 I 0.64263(3) 0.29644(2) 0.34983(2) 0.03681(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.402(5) . ?
C1 C6 1.402(5) . ?
C1 C7 1.494(5) . ?
C2 C3 1.385(5) . ?
C2 I1 2.120(4) . ?
C3 C4 1.386(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(5) . ?
C4 C8 1.494(5) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9500 . ?
C6 I2 2.119(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.401(5) . ?
C9 C14 1.407(5) . ?
C9 C15 1.492(5) . ?
C10 C11 1.384(5) . ?
C10 I3 2.113(3) . ?
C11 C12 1.392(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(6) . ?
C12 C16 1.506(5) . ?
C13 C14 1.394(5) . ?
C13 H13 0.9500 . ?
C14 I4 2.109(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C2 C1 C6 113.7(3) . . ?
C2 C1 C7 123.5(3) . . ?
C6 C1 C7 122.8(3) . . ?
C3 C2 C1 123.9(3) . . ?
C3 C2 I1 116.0(3) . . ?
C1 C2 I1 120.1(3) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 117.9(3) . . ?
C3 C4 C8 120.9(3) . . ?
C5 C4 C8 121.3(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 124.0(3) . . ?
C5 C6 I2 115.9(3) . . ?
C1 C6 I2 120.1(3) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 114.5(3) . . ?
C10 C9 C15 123.3(3) . . ?
C14 C9 C15 122.2(3) . . ?
C11 C10 C9 123.6(3) . . ?
C11 C10 I3 115.6(3) . . ?
C9 C10 I3 120.8(2) . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.2(3) . . ?
C13 C12 C16 121.2(3) . . ?
C11 C12 C16 120.6(4) . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 123.0(3) . . ?
C13 C14 I4 116.4(2) . . ?
C9 C14 I4 120.6(3) . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.832
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.144

_shelxl_version_number           2013-2

