# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_hmb-118K
_database_code_depnum_ccdc_archive 'CCDC 1057989'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
Hexamethylbenzene 
;
_chemical_formula_moiety         'C12 H18'
_chemical_formula_sum            'C12 H18'
_chemical_formula_weight         162.26
_chemical_melting_point          ?

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.2460(5)
_cell_length_b                   6.1956(7)
_cell_length_c                   7.9824(7)
_cell_angle_alpha                103.859(9)
_cell_angle_beta                 98.602(8)
_cell_angle_gamma                100.131(9)
_cell_volume                     242.93(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    995
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      29.0265
_cell_measurement_theta_min      4.3610
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             90
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2269
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         4.37
_diffrn_ambient_temperature      118(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9909
_diffrn_measured_fraction_theta_max 0.9082
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00    4.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -27.00    0.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  107.0000   33.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -39.00   51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960   57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00    4.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega  -93.00  -45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960 -178.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega    2.00   41.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928   57.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
  8 omega   17.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928   37.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
  9 omega  -43.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960   37.0000    0.0000 78
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0723795000
_diffrn_orient_matrix_UB_12      -0.0493838000
_diffrn_orient_matrix_UB_13      -0.0875050000
_diffrn_orient_matrix_UB_21      0.0571900000
_diffrn_orient_matrix_UB_22      0.0976682000
_diffrn_orient_matrix_UB_23      -0.0242235000
_diffrn_orient_matrix_UB_31      0.1055740000
_diffrn_orient_matrix_UB_32      -0.0513572000
_diffrn_orient_matrix_UB_33      -0.0219877000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                949
_reflns_number_total             1103
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0702
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1468P)²+0.0434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2140
_refine_ls_wR_factor_ref         0.2237
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H6A,H6B,H6C} of C6, {H5A,H5B,H5C} of C5, {H4A,H4B,H4C} of C4
2.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
C2 C 0.4316(3) 0.3853(2) 0.31958(18) 0.0180(5) Uani 1 1 d . . .
C3 C 0.6150(3) 0.3177(2) 0.43309(18) 0.0176(5) Uani 1 1 d . . .
C1 C 0.3205(3) 0.5702(2) 0.38639(19) 0.0182(5) Uani 1 1 d . . .
C6 C 0.7482(3) 0.1269(2) 0.3612(2) 0.0242(5) Uani 1 1 d . . .
H6A H 0.6655 -0.0125 0.3874 0.036 Uiso 1 1 calc R . .
H6B H 0.9364 0.1698 0.4163 0.036 Uiso 1 1 calc R . .
H6C H 0.7287 0.1001 0.2334 0.036 Uiso 1 1 calc R . .
C5 C 0.3508(3) 0.2560(3) 0.1263(2) 0.0262(5) Uani 1 1 d . . .
H5A H 0.4840 0.3100 0.0629 0.039 Uiso 1 1 calc R . .
H5B H 0.1794 0.2814 0.0772 0.039 Uiso 1 1 calc R . .
H5C H 0.3367 0.0928 0.1136 0.039 Uiso 1 1 calc R . .
C4 C 0.1316(3) 0.6513(3) 0.2651(2) 0.0250(5) Uani 1 1 d . . .
H4A H 0.1736 0.6185 0.1473 0.038 Uiso 1 1 calc R . .
H4B H 0.1492 0.8158 0.3112 0.038 Uiso 1 1 calc R . .
H4C H -0.0501 0.5719 0.2584 0.038 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
C2 0.0189(8) 0.0189(8) 0.0161(8) 0.0048(5) 0.0033(6) 0.0044(6)
C3 0.0180(8) 0.0174(7) 0.0180(8) 0.0054(5) 0.0034(6) 0.0053(5)
C1 0.0170(8) 0.0190(8) 0.0200(8) 0.0074(6) 0.0029(6) 0.0058(5)
C6 0.0269(9) 0.0216(8) 0.0246(9) 0.0037(6) 0.0054(6) 0.0099(6)
C5 0.0330(9) 0.0275(9) 0.0171(8) 0.0036(6) 0.0023(6) 0.0101(6)
C4 0.0244(8) 0.0299(9) 0.0210(8) 0.0084(6) -0.0011(6) 0.0098(6)

_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
C2 C3 1.409(2) . ?
C2 C1 1.404(2) . ?
C2 C5 1.515(2) . ?
C3 C1 1.402(2) 2_666 ?
C3 C6 1.5165(19) . ?
C1 C3 1.402(2) 2_666 ?
C1 C4 1.514(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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
C3 C2 C5 119.99(13) . . ?
C1 C2 C3 119.94(14) . . ?
C1 C2 C5 120.06(14) . . ?
C2 C3 C6 120.54(13) . . ?
C1 C3 C2 120.00(13) 2_666 . ?
C1 C3 C6 119.45(13) 2_666 . ?
C2 C1 C4 120.66(14) . . ?
C3 C1 C2 120.02(14) 2_666 . ?
C3 C1 C4 119.32(13) 2_666 . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_hmb-154K
_database_code_depnum_ccdc_archive 'CCDC 1057990'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
Hexamethylbenzene  
;
_chemical_formula_moiety         'C12 H18'
_chemical_formula_sum            'C12 H18'
_chemical_formula_weight         162.26
_chemical_melting_point          ?

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.2512(5)
_cell_length_b                   6.2279(7)
_cell_length_c                   7.9892(7)
_cell_angle_alpha                103.846(9)
_cell_angle_beta                 98.464(8)
_cell_angle_gamma                99.919(9)
_cell_volume                     245.00(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    983
_cell_measurement_temperature    154(2)
_cell_measurement_theta_max      28.9368
_cell_measurement_theta_min      4.0101
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             90
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2309
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         4.02
_diffrn_ambient_temperature      154(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9940
_diffrn_measured_fraction_theta_max 0.9400
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -77.00  -35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960 -178.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00    6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega   18.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928   57.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928  -99.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928   37.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega  -44.00   39.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928  -37.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
  8 omega   -7.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928   37.0000  -60.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0715052000
_diffrn_orient_matrix_UB_12      -0.0490750000
_diffrn_orient_matrix_UB_13      -0.0874005000
_diffrn_orient_matrix_UB_21      0.0563123000
_diffrn_orient_matrix_UB_22      0.0973459000
_diffrn_orient_matrix_UB_23      -0.0241289000
_diffrn_orient_matrix_UB_31      0.1061975000
_diffrn_orient_matrix_UB_32      -0.0504788000
_diffrn_orient_matrix_UB_33      -0.0218574000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                945
_reflns_number_total             1121
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0769
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1600P)²+0.0610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2292
_refine_ls_wR_factor_ref         0.2438
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H5A,H5B,H5C} of C5, {H4A,H4B,H4C} of C4, {H6A,H6B,H6C} of C6
2.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C2 C 0.4316(3) 0.3856(3) 0.3198(2) 0.0246(5) Uani 1 1 d . . .
C3 C 0.6141(3) 0.3181(3) 0.4330(2) 0.0240(5) Uani 1 1 d . . .
C1 C 0.3202(3) 0.5702(3) 0.3872(2) 0.0244(5) Uani 1 1 d . . .
C6 C 0.7445(4) 0.1258(3) 0.3610(2) 0.0322(5) Uani 1 1 d . . .
H6A H 0.6703 -0.0084 0.3960 0.048 Uiso 1 1 calc R . .
H6B H 0.9347 0.1712 0.4082 0.048 Uiso 1 1 calc R . .
H6C H 0.7128 0.0905 0.2325 0.048 Uiso 1 1 calc R . .
C5 C 0.3530(4) 0.2590(3) 0.1266(2) 0.0354(5) Uani 1 1 d . . .
H5A H 0.4940 0.3035 0.0659 0.053 Uiso 1 1 calc R . .
H5B H 0.1904 0.2959 0.0752 0.053 Uiso 1 1 calc R . .
H5C H 0.3237 0.0957 0.1138 0.053 Uiso 1 1 calc R . .
C4 C 0.1290(4) 0.6494(3) 0.2664(2) 0.0346(5) Uani 1 1 d . . .
H4A H 0.1748 0.6227 0.1497 0.052 Uiso 1 1 calc R . .
H4B H 0.1393 0.8116 0.3147 0.052 Uiso 1 1 calc R . .
H4C H -0.0507 0.5652 0.2568 0.052 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
C2 0.0251(9) 0.0245(9) 0.0248(9) 0.0075(6) 0.0046(6) 0.0062(6)
C3 0.0240(8) 0.0224(8) 0.0274(9) 0.0084(7) 0.0059(6) 0.0071(6)
C1 0.0226(8) 0.0239(9) 0.0288(9) 0.0099(7) 0.0042(6) 0.0071(6)
C6 0.0357(10) 0.0263(9) 0.0354(10) 0.0047(7) 0.0082(7) 0.0129(7)
C5 0.0436(11) 0.0361(10) 0.0256(10) 0.0048(7) 0.0039(7) 0.0141(8)
C4 0.0336(10) 0.0385(10) 0.0333(10) 0.0121(8) 0.0005(7) 0.0144(8)

_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
C2 C3 1.407(2) . ?
C2 C1 1.408(2) . ?
C2 C5 1.514(2) . ?
C3 C1 1.400(2) 2_666 ?
C3 C6 1.517(2) . ?
C1 C3 1.400(2) 2_666 ?
C1 C4 1.515(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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
C3 C2 C1 119.74(16) . . ?
C3 C2 C5 120.19(15) . . ?
C1 C2 C5 120.06(15) . . ?
C2 C3 C6 120.37(15) . . ?
C1 C3 C2 120.27(15) 2_666 . ?
C1 C3 C6 119.35(14) 2_666 . ?
C2 C1 C4 120.50(15) . . ?
C3 C1 C2 119.97(15) 2_666 . ?
C3 C1 C4 119.53(15) 2_666 . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
####################################################################### 
# 
# 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_hmb-190K
_database_code_depnum_ccdc_archive 'CCDC 1057991'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
Hexamethylbenzene  
;
_chemical_formula_moiety         'C12 H18'
_chemical_formula_sum            'C12 H18'
_chemical_formula_weight         162.26
_chemical_melting_point          ?

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.2639(9)
_cell_length_b                   6.2567(9)
_cell_length_c                   8.0155(10)
_cell_angle_alpha                103.858(12)
_cell_angle_beta                 98.504(12)
_cell_angle_gamma                99.750(13)
_cell_volume                     247.65(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    860
_cell_measurement_temperature    190.00(14)
_cell_measurement_theta_max      29.0680
_cell_measurement_theta_min      4.6795
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             90
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2274
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         4.69
_diffrn_ambient_temperature      190.00(14)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9891
_diffrn_measured_fraction_theta_max 0.9208
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960   57.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -81.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -77.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   20.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega  -52.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960   19.0000  150.0000 104

#__ type_ start__ end____ width___ exp.time_
  6 omega  -93.00  -35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960 -178.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega  -11.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928   77.0000  150.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0707775000
_diffrn_orient_matrix_UB_12      -0.0489712000
_diffrn_orient_matrix_UB_13      -0.0872171000
_diffrn_orient_matrix_UB_21      0.0553717000
_diffrn_orient_matrix_UB_22      0.0970907000
_diffrn_orient_matrix_UB_23      -0.0239240000
_diffrn_orient_matrix_UB_31      0.1066398000
_diffrn_orient_matrix_UB_32      -0.0495866000
_diffrn_orient_matrix_UB_33      -0.0215234000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                923
_reflns_number_total             1119
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0818
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1765P)²+0.0561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2496
_refine_ls_wR_factor_ref         0.2681
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H6A,H6B,H6C} of C6, {H5A,H5B,H5C} of C5, {H4A,H4B,H4C} of C4
2.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C2 C 0.4319(3) 0.3864(3) 0.3206(2) 0.0271(5) Uani 1 1 d . . .
C3 C 0.6139(3) 0.3184(3) 0.4327(2) 0.0270(5) Uani 1 1 d . . .
C1 C 0.3200(3) 0.5697(3) 0.3877(2) 0.0272(6) Uani 1 1 d . . .
C6 C 0.7420(4) 0.1257(3) 0.3611(3) 0.0377(6) Uani 1 1 d . . .
H6A H 0.6674 -0.0049 0.3946 0.057 Uiso 1 1 calc R . .
H6B H 0.9276 0.1680 0.4078 0.057 Uiso 1 1 calc R . .
H6C H 0.7122 0.0920 0.2356 0.057 Uiso 1 1 calc R . .
C5 C 0.3547(4) 0.2613(4) 0.1272(3) 0.0414(6) Uani 1 1 d . . .
H5A H 0.4984 0.2961 0.0703 0.062 Uiso 1 1 calc R . .
H5B H 0.2039 0.3066 0.0748 0.062 Uiso 1 1 calc R . .
H5C H 0.3129 0.1020 0.1143 0.062 Uiso 1 1 calc R . .
C4 C 0.1278(4) 0.6479(4) 0.2674(3) 0.0404(6) Uani 1 1 d . . .
H4A H 0.1722 0.6221 0.1534 0.061 Uiso 1 1 calc R . .
H4B H 0.1367 0.8058 0.3145 0.061 Uiso 1 1 calc R . .
H4C H -0.0472 0.5653 0.2582 0.061 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
C2 0.0266(9) 0.0274(9) 0.0272(9) 0.0072(7) 0.0044(7) 0.0064(7)
C3 0.0265(9) 0.0241(9) 0.0317(10) 0.0086(7) 0.0058(7) 0.0074(6)
C1 0.0254(9) 0.0263(9) 0.0316(10) 0.0104(7) 0.0036(7) 0.0082(7)
C6 0.0409(11) 0.0303(10) 0.0431(11) 0.0054(8) 0.0099(9) 0.0155(8)
C5 0.0496(12) 0.0426(12) 0.0298(10) 0.0051(8) 0.0026(8) 0.0152(9)
C4 0.0372(11) 0.0448(12) 0.0404(12) 0.0148(9) -0.0022(8) 0.0161(9)

_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
C2 C3 1.404(3) . ?
C2 C1 1.407(2) . ?
C2 C5 1.518(3) . ?
C3 C1 1.404(3) 2_666 ?
C3 C6 1.515(2) . ?
C1 C3 1.404(3) 2_666 ?
C1 C4 1.516(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 120.00(17) . . ?
C3 C2 C5 120.04(16) . . ?
C1 C2 C5 119.97(16) . . ?
C2 C3 C6 120.52(17) . . ?
C1 C3 C2 120.00(16) 2_666 . ?
C1 C3 C6 119.48(16) 2_666 . ?
C2 C1 C4 120.51(17) . . ?
C3 C1 C2 119.99(16) 2_666 . ?
C3 C1 C4 119.51(16) 2_666 . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
####################################################################### 
# 
# 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_hmb-226K
_database_code_depnum_ccdc_archive 'CCDC 1057992'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
Hexamethylbenzene  
;
_chemical_formula_moiety         'C12 H18'
_chemical_formula_sum            'C12 H18'
_chemical_formula_weight         162.26
_chemical_melting_point          ?

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.2748(9)
_cell_length_b                   6.2602(15)
_cell_length_c                   8.0316(12)
_cell_angle_alpha                103.949(16)
_cell_angle_beta                 98.651(13)
_cell_angle_gamma                99.531(17)
_cell_volume                     248.77(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    868
_cell_measurement_temperature    226(2)
_cell_measurement_theta_max      28.7458
_cell_measurement_theta_min      5.2206
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             90
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2321
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.81
_diffrn_reflns_theta_min         5.23
_diffrn_ambient_temperature      226(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9901
_diffrn_measured_fraction_theta_max 0.9208
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00  -17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  109.0000   32.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega  -85.00  -41.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  178.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega   25.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928  -99.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928  -37.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928    0.0000  -30.0000 114

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00  -43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960 -178.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega  -86.00    4.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -57.0000    0.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0691614000
_diffrn_orient_matrix_UB_12      -0.0493185000
_diffrn_orient_matrix_UB_13      -0.0874844000
_diffrn_orient_matrix_UB_21      0.0556714000
_diffrn_orient_matrix_UB_22      0.0968245000
_diffrn_orient_matrix_UB_23      -0.0236574000
_diffrn_orient_matrix_UB_31      0.1071209000
_diffrn_orient_matrix_UB_32      -0.0495332000
_diffrn_orient_matrix_UB_33      -0.0202057000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                920
_reflns_number_total             1135
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1670P)²+0.0597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2517
_refine_ls_wR_factor_ref         0.2724
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H5A,H5B,H5C} of C5, {H6A,H6B,H6C} of C6, {H4A,H4B,H4C} of C4
2.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C2 C 0.4317(3) 0.3865(3) 0.3211(2) 0.0323(6) Uani 1 1 d . . .
C3 C 0.6140(3) 0.3187(3) 0.4329(2) 0.0319(6) Uani 1 1 d . . .
C1 C 0.3203(3) 0.5695(3) 0.3878(2) 0.0323(6) Uani 1 1 d . . .
C6 C 0.7400(4) 0.1252(4) 0.3615(3) 0.0460(7) Uani 1 1 d . . .
H6A H 0.6641 -0.0061 0.3953 0.069 Uiso 1 1 calc R . .
H6B H 0.9272 0.1666 0.4086 0.069 Uiso 1 1 calc R . .
H6C H 0.7095 0.0909 0.2349 0.069 Uiso 1 1 calc R . .
C5 C 0.3551(5) 0.2621(4) 0.1281(3) 0.0497(7) Uani 1 1 d . . .
H5A H 0.4996 0.2979 0.0709 0.075 Uiso 1 1 calc R . .
H5B H 0.2025 0.3076 0.0753 0.075 Uiso 1 1 calc R . .
H5C H 0.3141 0.1013 0.1147 0.075 Uiso 1 1 calc R . .
C4 C 0.1272(4) 0.6471(4) 0.2685(3) 0.0484(7) Uani 1 1 d . . .
H4A H 0.1716 0.6219 0.1534 0.073 Uiso 1 1 calc R . .
H4B H 0.1346 0.8063 0.3166 0.073 Uiso 1 1 calc R . .
H4C H -0.0486 0.5628 0.2589 0.073 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
C2 0.0330(10) 0.0326(10) 0.0307(9) 0.0080(7) 0.0048(7) 0.0076(7)
C3 0.0322(10) 0.0294(9) 0.0355(10) 0.0093(7) 0.0073(7) 0.0092(7)
C1 0.0307(10) 0.0323(10) 0.0353(10) 0.0119(8) 0.0035(7) 0.0094(7)
C6 0.0494(13) 0.0386(11) 0.0511(13) 0.0066(9) 0.0119(9) 0.0194(9)
C5 0.0625(14) 0.0521(13) 0.0326(11) 0.0058(9) 0.0054(9) 0.0188(11)
C4 0.0456(12) 0.0551(13) 0.0469(12) 0.0191(10) -0.0011(9) 0.0192(10)

_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
C2 C3 1.404(3) . ?
C2 C1 1.402(3) . ?
C2 C5 1.515(3) . ?
C3 C1 1.403(3) 2_666 ?
C3 C6 1.511(3) . ?
C1 C3 1.403(3) 2_666 ?
C1 C4 1.512(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 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
C3 C2 C5 120.06(16) . . ?
C1 C2 C3 120.01(17) . . ?
C1 C2 C5 119.93(16) . . ?
C2 C3 C6 120.44(17) . . ?
C1 C3 C2 119.95(16) 2_666 . ?
C1 C3 C6 119.61(16) 2_666 . ?
C2 C1 C3 120.02(16) . 2_666 ?
C2 C1 C4 120.64(17) . . ?
C3 C1 C4 119.34(17) 2_666 . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
####################################################################### 
# 
# 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_hmb-262K
_database_code_depnum_ccdc_archive 'CCDC 1057993'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
Hexamethylbenzene  
;
_chemical_formula_moiety         'C12 H18'
_chemical_formula_sum            'C12 H18'
_chemical_formula_weight         162.26
_chemical_melting_point          ?

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.2944(5)
_cell_length_b                   6.2771(6)
_cell_length_c                   8.0612(7)
_cell_angle_alpha                104.026(8)
_cell_angle_beta                 98.839(8)
_cell_angle_gamma                99.456(8)
_cell_volume                     251.09(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    828
_cell_measurement_temperature    262(2)
_cell_measurement_theta_max      29.0423
_cell_measurement_theta_min      4.6668
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.073
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             90
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2311
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         4.68
_diffrn_ambient_temperature      262(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9893
_diffrn_measured_fraction_theta_max 0.9118
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -80.00   12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -77.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928   57.0000  -30.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega  -22.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928   19.0000  -90.0000 106

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928 -178.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2928  178.0000  -30.0000 60
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0730030000
_diffrn_orient_matrix_UB_12      -0.0472899000
_diffrn_orient_matrix_UB_13      -0.0865255000
_diffrn_orient_matrix_UB_21      0.0594014000
_diffrn_orient_matrix_UB_22      0.0945428000
_diffrn_orient_matrix_UB_23      -0.0242481000
_diffrn_orient_matrix_UB_31      0.1018553000
_diffrn_orient_matrix_UB_32      -0.0549336000
_diffrn_orient_matrix_UB_33      -0.0223843000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                890
_reflns_number_total             1142
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0822
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1696P)²+0.0421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2540
_refine_ls_wR_factor_ref         0.2755
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H6A,H6B,H6C} of C6, {H5A,H5B,H5C} of C5, {H4A,H4B,H4C} of C4
2.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C2 C 0.4320(3) 0.3873(3) 0.3218(2) 0.0396(6) Uani 1 1 d . . .
C3 C 0.6133(3) 0.3193(3) 0.4333(2) 0.0393(6) Uani 1 1 d . . .
C1 C 0.3198(3) 0.5695(3) 0.3887(2) 0.0394(6) Uani 1 1 d . . .
C6 C 0.7389(4) 0.1256(4) 0.3620(3) 0.0560(7) Uani 1 1 d . . .
H6A H 0.6652 -0.0036 0.3959 0.084 Uiso 1 1 calc R . .
H6B H 0.9239 0.1668 0.4078 0.084 Uiso 1 1 calc R . .
H6C H 0.7073 0.0908 0.2369 0.084 Uiso 1 1 calc R . .
C5 C 0.3559(5) 0.2638(4) 0.1291(3) 0.0607(7) Uani 1 1 d . . .
H5A H 0.5050 0.2851 0.0759 0.091 Uiso 1 1 calc R . .
H5B H 0.2188 0.3216 0.0740 0.091 Uiso 1 1 calc R . .
H5C H 0.2958 0.1064 0.1153 0.091 Uiso 1 1 calc R . .
C4 C 0.1261(5) 0.6459(4) 0.2691(3) 0.0587(7) Uani 1 1 d . . .
H4A H 0.1632 0.6124 0.1538 0.088 Uiso 1 1 calc R . .
H4B H 0.1403 0.8048 0.3126 0.088 Uiso 1 1 calc R . .
H4C H -0.0480 0.5688 0.2652 0.088 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
C2 0.0391(10) 0.0416(10) 0.0382(10) 0.0117(8) 0.0061(7) 0.0090(7)
C3 0.0373(10) 0.0369(10) 0.0464(11) 0.0135(8) 0.0096(7) 0.0111(7)
C1 0.0356(10) 0.0399(10) 0.0455(11) 0.0170(8) 0.0049(7) 0.0109(7)
C6 0.0570(13) 0.0476(12) 0.0662(15) 0.0101(10) 0.0157(10) 0.0238(9)
C5 0.0726(15) 0.0657(15) 0.0403(12) 0.0081(10) 0.0050(10) 0.0208(12)
C4 0.0543(13) 0.0668(15) 0.0591(14) 0.0257(11) -0.0015(10) 0.0236(10)

_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
C2 C3 1.402(3) . ?
C2 C1 1.405(3) . ?
C2 C5 1.516(3) . ?
C3 C1 1.396(3) 2_666 ?
C3 C6 1.515(3) . ?
C1 C3 1.396(3) 2_666 ?
C1 C4 1.514(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 120.05(17) . . ?
C3 C2 C5 120.07(17) . . ?
C1 C2 C5 119.87(17) . . ?
C2 C3 C6 120.45(18) . . ?
C1 C3 C2 120.13(17) 2_666 . ?
C1 C3 C6 119.41(17) 2_666 . ?
C2 C1 C4 120.48(18) . . ?
C3 C1 C2 119.81(17) 2_666 . ?
C3 C1 C4 119.71(17) 2_666 . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

####################################################################### 
# 
# 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_tbm-118K
_database_code_depnum_ccdc_archive 'CCDC 1057994'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
tribromomesitylene 
;
_chemical_formula_moiety         'C9 H9 Br3'
_chemical_formula_sum            'C9 H9 Br3'
_chemical_formula_weight         356.89
_chemical_melting_point          ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.6628(7)
_cell_length_b                   9.0535(7)
_cell_length_c                   9.0675(7)
_cell_angle_alpha                119.828(8)
_cell_angle_beta                 106.926(8)
_cell_angle_gamma                95.170(7)
_cell_volume                     500.73(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1752
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      29.1355
_cell_measurement_theta_min      4.1346
_exptl_absorpt_coefficient_mu    12.026
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4813
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         4.14
_diffrn_ambient_temperature      118(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9922
_diffrn_measured_fraction_theta_max 0.9366
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -38.00    8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -19.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -80.00   -1.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   24.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega  -42.00   15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  6 omega   27.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega  -74.00   -6.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  150.0000 68

#__ type_ start__ end____ width___ exp.time_
  8 omega  -83.00  -53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -19.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega  -47.00   53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000   90.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0510595000
_diffrn_orient_matrix_UB_12      0.0459680000
_diffrn_orient_matrix_UB_13      0.0538463000
_diffrn_orient_matrix_UB_21      0.0777172000
_diffrn_orient_matrix_UB_22      0.0779265000
_diffrn_orient_matrix_UB_23      0.0538214000
_diffrn_orient_matrix_UB_31      -0.0391142000
_diffrn_orient_matrix_UB_32      0.0260879000
_diffrn_orient_matrix_UB_33      -0.0615051000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1940
_reflns_number_total             2296
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         1.159
_refine_diff_density_min         -1.649
_refine_diff_density_rms         0.215
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0430P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0885
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H7A,H7B,H7C} of C7, {H9A,H9B,H9C} of C9, {H8A,H8B,H8C} of C8
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Br3 Br 0.73210(7) 0.60129(6) 0.74179(6) 0.01673(14) Uani 1 1 d . . .
Br2 Br 0.78217(7) 0.73157(6) 1.43514(6) 0.01544(14) Uani 1 1 d . . .
Br1 Br 0.73351(7) 0.04338(6) 0.86219(7) 0.01797(14) Uani 1 1 d . . .
C5 C 0.7436(6) 0.5195(6) 0.9011(6) 0.0099(9) Uani 1 1 d . . .
C7 C 0.7613(7) 0.3266(6) 1.2513(7) 0.0179(10) Uani 1 1 d . . .
H7A H 0.8821 0.2992 1.2834 0.027 Uiso 1 1 calc R . .
H7B H 0.6557 0.2189 1.1856 0.027 Uiso 1 1 calc R . .
H7C H 0.7496 0.4172 1.3642 0.027 Uiso 1 1 calc R . .
C6 C 0.7381(6) 0.3411(6) 0.8291(6) 0.0111(9) Uani 1 1 d . . .
C9 C 0.7244(7) 0.2177(6) 0.6347(6) 0.0162(10) Uani 1 1 d . . .
H9A H 0.8220 0.2730 0.6133 0.024 Uiso 1 1 calc R . .
H9B H 0.5983 0.1944 0.5469 0.024 Uiso 1 1 calc R . .
H9C H 0.7440 0.1057 0.6176 0.024 Uiso 1 1 calc R . .
C1 C 0.7436(6) 0.2854(6) 0.9484(6) 0.0111(9) Uani 1 1 d . . .
C2 C 0.7559(6) 0.3951(6) 1.1297(6) 0.0113(9) Uani 1 1 d . . .
C8 C 0.7637(7) 0.8320(6) 1.1504(7) 0.0168(10) Uani 1 1 d . . .
H8A H 0.7613 0.8543 1.0546 0.025 Uiso 1 1 calc R . .
H8B H 0.8812 0.9090 1.2600 0.025 Uiso 1 1 calc R . .
H8C H 0.6538 0.8574 1.1828 0.025 Uiso 1 1 calc R . .
C4 C 0.7558(6) 0.6393(6) 1.0787(6) 0.0113(9) Uani 1 1 d . . .
C3 C 0.7611(6) 0.5709(6) 1.1881(6) 0.0105(9) Uani 1 1 d . . .

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
Br3 0.0270(3) 0.0131(2) 0.0131(3) 0.0096(2) 0.0074(2) 0.0049(2)
Br2 0.0237(3) 0.0103(2) 0.0088(3) 0.0030(2) 0.0065(2) 0.0032(2)
Br1 0.0308(3) 0.0071(2) 0.0167(3) 0.0062(2) 0.0104(2) 0.0065(2)
C5 0.008(2) 0.008(2) 0.012(2) 0.0069(19) 0.0000(18) 0.0005(17)
C7 0.034(3) 0.016(2) 0.015(3) 0.012(2) 0.014(2) 0.012(2)
C6 0.009(2) 0.010(2) 0.011(2) 0.0056(19) 0.0014(19) 0.0001(18)
C9 0.019(2) 0.014(2) 0.011(2) 0.005(2) 0.004(2) 0.002(2)
C1 0.013(2) 0.003(2) 0.018(3) 0.0070(19) 0.0039(19) 0.0026(18)
C2 0.012(2) 0.007(2) 0.013(2) 0.0050(19) 0.004(2) 0.0020(18)
C8 0.027(3) 0.003(2) 0.017(3) 0.003(2) 0.008(2) 0.003(2)
C4 0.011(2) 0.005(2) 0.012(2) 0.0032(18) 0.0016(19) -0.0002(18)
C3 0.011(2) 0.010(2) 0.006(2) 0.0025(18) 0.0026(18) 0.0023(18)

_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
Br3 C5 1.909(4) . ?
Br2 C3 1.915(4) . ?
Br1 C1 1.910(4) . ?
C5 C6 1.399(6) . ?
C5 C4 1.391(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C2 1.504(6) . ?
C6 C9 1.510(6) . ?
C6 C1 1.395(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C1 C2 1.402(6) . ?
C2 C3 1.397(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C4 1.517(6) . ?
C4 C3 1.400(6) . ?

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
C6 C5 Br3 117.0(3) . . ?
C4 C5 Br3 118.4(3) . . ?
C4 C5 C6 124.6(4) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
C5 C6 C9 122.0(4) . . ?
C1 C6 C5 115.4(4) . . ?
C1 C6 C9 122.6(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C1 Br1 118.7(3) . . ?
C6 C1 C2 124.6(4) . . ?
C2 C1 Br1 116.8(3) . . ?
C1 C2 C7 121.9(4) . . ?
C3 C2 C7 122.7(4) . . ?
C3 C2 C1 115.4(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C5 C4 C8 122.4(4) . . ?
C5 C4 C3 115.7(4) . . ?
C3 C4 C8 121.9(4) . . ?
C2 C3 Br2 118.4(3) . . ?
C2 C3 C4 124.3(4) . . ?
C4 C3 Br2 117.3(3) . . ?
####################################################################### 
# 
# 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_tbm-154K
_database_code_depnum_ccdc_archive 'CCDC 1057995'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
tribromomesitylene 
;
_chemical_formula_moiety         'C9 H9 Br3'
_chemical_formula_sum            'C9 H9 Br3'
_chemical_formula_weight         356.89
_chemical_melting_point          ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.6795(6)
_cell_length_b                   9.0494(7)
_cell_length_c                   9.0657(8)
_cell_angle_alpha                119.817(9)
_cell_angle_beta                 106.887(7)
_cell_angle_gamma                95.081(7)
_cell_volume                     502.03(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1684
_cell_measurement_temperature    154(2)
_cell_measurement_theta_max      29.0477
_cell_measurement_theta_min      4.1291
_exptl_absorpt_coefficient_mu    11.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4843
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         4.14
_diffrn_ambient_temperature      154(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9951
_diffrn_measured_fraction_theta_max 0.9512
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   51.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00   16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -103.0000    8.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega  -42.00  -16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   12.00   52.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega   42.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366  178.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega  -86.00  -61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega  -86.00    4.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000   90.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0509660000
_diffrn_orient_matrix_UB_12      0.0460621000
_diffrn_orient_matrix_UB_13      0.0538919000
_diffrn_orient_matrix_UB_21      0.0774170000
_diffrn_orient_matrix_UB_22      0.0778104000
_diffrn_orient_matrix_UB_23      0.0536591000
_diffrn_orient_matrix_UB_31      -0.0390239000
_diffrn_orient_matrix_UB_32      0.0261316000
_diffrn_orient_matrix_UB_33      -0.0614936000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1909
_reflns_number_total             2317
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.671
_refine_diff_density_min         -1.306
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0921
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H9A,H9B,H9C} of C9, {H7A,H7B,H7C} of C7, {H8A,H8B,H8C} of C8
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Br3 Br 0.73343(7) 0.60157(7) 0.74213(7) 0.02257(15) Uani 1 1 d . . .
Br2 Br 0.78200(7) 0.73121(7) 1.43419(7) 0.02092(15) Uani 1 1 d . . .
Br1 Br 0.73260(8) 0.04399(7) 0.86179(7) 0.02418(16) Uani 1 1 d . . .
C5 C 0.7452(6) 0.5191(7) 0.9011(6) 0.0143(10) Uani 1 1 d . . .
C7 C 0.7610(8) 0.3275(8) 1.2510(7) 0.0245(12) Uani 1 1 d . . .
H7A H 0.8889 0.3189 1.2995 0.037 Uiso 1 1 calc R . .
H7B H 0.6699 0.2098 1.1793 0.037 Uiso 1 1 calc R . .
H7C H 0.7282 0.4090 1.3537 0.037 Uiso 1 1 calc R . .
C6 C 0.7384(6) 0.3416(6) 0.8300(6) 0.0138(10) Uani 1 1 d . . .
C9 C 0.7273(8) 0.2209(7) 0.6379(7) 0.0219(11) Uani 1 1 d . . .
H9A H 0.8386 0.2667 0.6249 0.033 Uiso 1 1 calc R . .
H9B H 0.6120 0.2150 0.5501 0.033 Uiso 1 1 calc R . .
H9C H 0.7239 0.1019 0.6129 0.033 Uiso 1 1 calc R . .
C1 C 0.7431(6) 0.2861(6) 0.9480(6) 0.0142(9) Uani 1 1 d . . .
C2 C 0.7546(6) 0.3959(7) 1.1289(6) 0.0145(10) Uani 1 1 d . . .
C8 C 0.7637(7) 0.8302(7) 1.1486(7) 0.0219(11) Uani 1 1 d . . .
H8A H 0.6665 0.8362 1.0555 0.033 Uiso 1 1 calc R . .
H8B H 0.8891 0.8941 1.1732 0.033 Uiso 1 1 calc R . .
H8C H 0.7404 0.8845 1.2627 0.033 Uiso 1 1 calc R . .
C4 C 0.7565(6) 0.6418(7) 1.0798(6) 0.0146(10) Uani 1 1 d . . .
C3 C 0.7617(6) 0.5715(6) 1.1884(6) 0.0123(9) Uani 1 1 d . . .

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
Br3 0.0368(3) 0.0187(3) 0.0194(3) 0.0144(2) 0.0121(2) 0.0086(2)
Br2 0.0328(3) 0.0148(3) 0.0138(3) 0.0057(2) 0.0113(2) 0.0064(2)
Br1 0.0420(3) 0.0109(3) 0.0241(3) 0.0101(2) 0.0165(2) 0.0107(2)
C5 0.015(2) 0.012(3) 0.017(2) 0.010(2) 0.0053(19) 0.0032(19)
C7 0.045(3) 0.024(3) 0.022(3) 0.019(3) 0.022(3) 0.018(3)
C6 0.013(2) 0.013(3) 0.014(2) 0.006(2) 0.0060(19) 0.004(2)
C9 0.034(3) 0.013(3) 0.020(3) 0.008(2) 0.012(2) 0.007(2)
C1 0.019(2) 0.009(2) 0.015(2) 0.007(2) 0.0063(19) 0.0038(19)
C2 0.017(2) 0.013(3) 0.013(2) 0.007(2) 0.0054(19) 0.004(2)
C8 0.033(3) 0.012(3) 0.025(3) 0.011(2) 0.014(2) 0.007(2)
C4 0.015(2) 0.016(3) 0.014(2) 0.009(2) 0.0053(19) 0.005(2)
C3 0.015(2) 0.009(2) 0.010(2) 0.004(2) 0.0043(18) 0.0020(19)

_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
Br3 C5 1.910(4) . ?
Br2 C3 1.906(5) . ?
Br1 C1 1.910(5) . ?
C5 C6 1.390(7) . ?
C5 C4 1.407(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C2 1.506(6) . ?
C6 C9 1.496(6) . ?
C6 C1 1.384(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C1 C2 1.402(6) . ?
C2 C3 1.390(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C4 1.485(7) . ?
C4 C3 1.407(6) . ?

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
C6 C5 Br3 117.5(3) . . ?
C6 C5 C4 125.1(4) . . ?
C4 C5 Br3 117.4(3) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
C5 C6 C9 121.3(4) . . ?
C1 C6 C5 115.7(4) . . ?
C1 C6 C9 123.0(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C1 Br1 118.7(4) . . ?
C6 C1 C2 124.4(5) . . ?
C2 C1 Br1 116.9(3) . . ?
C1 C2 C7 121.8(4) . . ?
C3 C2 C7 122.4(4) . . ?
C3 C2 C1 115.8(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C5 C4 C8 122.8(4) . . ?
C5 C4 C3 114.4(4) . . ?
C3 C4 C8 122.8(4) . . ?
C2 C3 Br2 118.7(3) . . ?
C2 C3 C4 124.5(4) . . ?
C4 C3 Br2 116.8(4) . . ?
####################################################################### 
# 
# 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_tbm-190K
_database_code_depnum_ccdc_archive 'CCDC 1057996'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
tribromomesitylene 
;
_chemical_formula_moiety         'C9 H9 Br3'
_chemical_formula_sum            'C9 H9 Br3'
_chemical_formula_weight         356.89
_chemical_melting_point          ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.7114(7)
_cell_length_b                   9.0669(8)
_cell_length_c                   9.0829(8)
_cell_angle_alpha                119.802(9)
_cell_angle_beta                 106.864(8)
_cell_angle_gamma                95.034(7)
_cell_volume                     506.39(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1569
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      29.0684
_cell_measurement_theta_min      4.1155
_exptl_absorpt_coefficient_mu    11.892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4841
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         4.12
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9923
_diffrn_measured_fraction_theta_max 0.9372
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   17.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -103.0000    8.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   23.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000 -120.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -38.00   47.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000  120.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega  -26.00   49.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega  -71.00  -19.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega  -32.00   50.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega  -86.00  -59.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega  -86.00    4.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000   90.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0506953000
_diffrn_orient_matrix_UB_12      0.0460782000
_diffrn_orient_matrix_UB_13      0.0538518000
_diffrn_orient_matrix_UB_21      0.0770602000
_diffrn_orient_matrix_UB_22      0.0775334000
_diffrn_orient_matrix_UB_23      0.0533896000
_diffrn_orient_matrix_UB_31      -0.0388723000
_diffrn_orient_matrix_UB_32      0.0260856000
_diffrn_orient_matrix_UB_33      -0.0613747000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1852
_reflns_number_total             2332
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.839
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       0.0155(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0373P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0911
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H9A,H9B,H9C} of C9, {H8A,H8B,H8C} of C8, {H7A,H7B,H7C} of C7
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Br3 Br 0.73439(8) 0.60195(7) 0.74264(7) 0.02855(18) Uani 1 1 d . . .
Br2 Br 0.78213(7) 0.73092(7) 1.43341(7) 0.02673(17) Uani 1 1 d . . .
Br1 Br 0.73182(8) 0.04450(7) 0.86130(8) 0.03049(18) Uani 1 1 d . . .
C5 C 0.7445(6) 0.5200(7) 0.9010(7) 0.0182(10) Uani 1 1 d . . .
C7 C 0.7594(8) 0.3257(7) 1.2491(7) 0.0293(13) Uani 1 1 d . . .
H7A H 0.8352 0.2413 1.2268 0.044 Uiso 1 1 calc R . .
H7B H 0.6304 0.2658 1.2193 0.044 Uiso 1 1 calc R . .
H7C H 0.8153 0.4237 1.3788 0.044 Uiso 1 1 calc R . .
C6 C 0.7380(6) 0.3433(6) 0.8289(6) 0.0179(10) Uani 1 1 d . . .
C9 C 0.7271(7) 0.2197(7) 0.6371(7) 0.0246(11) Uani 1 1 d . . .
H9A H 0.8406 0.2612 0.6248 0.037 Uiso 1 1 calc R . .
H9B H 0.6153 0.2166 0.5487 0.037 Uiso 1 1 calc R . .
H9C H 0.7183 0.1005 0.6125 0.037 Uiso 1 1 calc R . .
C1 C 0.7441(6) 0.2869(6) 0.9494(7) 0.0187(10) Uani 1 1 d . . .
C2 C 0.7555(6) 0.3972(7) 1.1291(6) 0.0182(10) Uani 1 1 d . . .
C8 C 0.7631(7) 0.8304(7) 1.1481(7) 0.0266(12) Uani 1 1 d . . .
H8A H 0.6969 0.8403 1.0449 0.040 Uiso 1 1 calc R . .
H8B H 0.8948 0.9022 1.2088 0.040 Uiso 1 1 calc R . .
H8C H 0.7017 0.8729 1.2363 0.040 Uiso 1 1 calc R . .
C4 C 0.7569(6) 0.6412(7) 1.0781(7) 0.0194(10) Uani 1 1 d . . .
C3 C 0.7619(6) 0.5721(6) 1.1882(6) 0.0166(10) Uani 1 1 d . . .

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
Br3 0.0453(3) 0.0233(3) 0.0238(3) 0.0170(3) 0.0141(2) 0.0097(3)
Br2 0.0402(3) 0.0186(3) 0.0174(3) 0.0064(2) 0.0130(2) 0.0070(2)
Br1 0.0512(4) 0.0135(3) 0.0297(3) 0.0116(3) 0.0191(3) 0.0118(3)
C5 0.018(2) 0.018(3) 0.018(3) 0.010(2) 0.0057(19) 0.003(2)
C7 0.048(3) 0.030(3) 0.028(3) 0.021(3) 0.023(3) 0.020(3)
C6 0.020(2) 0.013(3) 0.016(3) 0.006(2) 0.0051(19) 0.002(2)
C9 0.040(3) 0.020(3) 0.018(3) 0.011(2) 0.014(2) 0.013(2)
C1 0.021(2) 0.010(2) 0.026(3) 0.011(2) 0.008(2) 0.004(2)
C2 0.019(2) 0.018(3) 0.017(3) 0.009(2) 0.007(2) 0.003(2)
C8 0.039(3) 0.013(3) 0.028(3) 0.011(3) 0.013(2) 0.005(2)
C4 0.018(2) 0.016(3) 0.020(3) 0.009(2) 0.0028(19) 0.002(2)
C3 0.023(2) 0.010(2) 0.011(2) 0.004(2) 0.0040(19) 0.001(2)

_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
Br3 C5 1.906(4) . ?
Br2 C3 1.905(5) . ?
Br1 C1 1.911(5) . ?
C5 C6 1.387(7) . ?
C5 C4 1.392(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C2 1.515(6) . ?
C6 C9 1.503(6) . ?
C6 C1 1.411(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C1 C2 1.397(6) . ?
C2 C3 1.389(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C4 1.495(7) . ?
C4 C3 1.413(6) . ?

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
C6 C5 Br3 116.8(3) . . ?
C6 C5 C4 125.5(4) . . ?
C4 C5 Br3 117.8(4) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
C5 C6 C9 122.9(4) . . ?
C5 C6 C1 115.2(4) . . ?
C1 C6 C9 121.9(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C1 Br1 118.4(4) . . ?
C2 C1 Br1 117.7(3) . . ?
C2 C1 C6 123.9(4) . . ?
C1 C2 C7 120.6(4) . . ?
C3 C2 C7 123.1(4) . . ?
C3 C2 C1 116.3(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C5 C4 C8 123.0(4) . . ?
C5 C4 C3 115.1(4) . . ?
C3 C4 C8 121.9(4) . . ?
C2 C3 Br2 118.5(3) . . ?
C2 C3 C4 124.0(4) . . ?
C4 C3 Br2 117.5(3) . . ?
####################################################################### 
# 
# 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_tbm-226K
_database_code_depnum_ccdc_archive 'CCDC 1057997'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
tribromomesitylene 
;
_chemical_formula_moiety         'C9 H9 Br3'
_chemical_formula_sum            'C9 H9 Br3'
_chemical_formula_weight         356.89
_chemical_melting_point          ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.7305(7)
_cell_length_b                   9.0698(8)
_cell_length_c                   9.0855(9)
_cell_angle_alpha                119.773(10)
_cell_angle_beta                 106.867(9)
_cell_angle_gamma                95.034(8)
_cell_volume                     508.12(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1388
_cell_measurement_temperature    226(2)
_cell_measurement_theta_max      29.0661
_cell_measurement_theta_min      4.1097
_exptl_absorpt_coefficient_mu    11.851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4728
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         4.12
_diffrn_ambient_temperature      226(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9928
_diffrn_measured_fraction_theta_max 0.9327
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -34.00   51.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   25.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -102.0000    7.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -32.00   46.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000  120.0000 78

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00    3.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -29.00   51.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   62.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  178.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   32.00   61.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -99.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega  -87.00   13.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000 -120.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0503276000
_diffrn_orient_matrix_UB_12      0.0459088000
_diffrn_orient_matrix_UB_13      0.0541869000
_diffrn_orient_matrix_UB_21      0.0773922000
_diffrn_orient_matrix_UB_22      0.0771027000
_diffrn_orient_matrix_UB_23      0.0541417000
_diffrn_orient_matrix_UB_31      -0.0380347000
_diffrn_orient_matrix_UB_32      0.0274008000
_diffrn_orient_matrix_UB_33      -0.0603171000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1794
_reflns_number_total             2329
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       0.0204(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0307P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0827
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H7A,H7B,H7C} of C7, {H9A,H9B,H9C} of C9, {H8A,H8B,H8C} of C8
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Br3 Br 0.73497(8) 0.60221(7) 0.74296(7) 0.03469(18) Uani 1 1 d . . .
Br2 Br 0.78229(7) 0.73068(7) 1.43256(6) 0.03289(17) Uani 1 1 d . . .
Br1 Br 0.73120(8) 0.04540(7) 0.86119(7) 0.03689(18) Uani 1 1 d . . .
C5 C 0.7449(6) 0.5201(6) 0.9004(6) 0.0229(10) Uani 1 1 d . . .
C7 C 0.7594(8) 0.3271(7) 1.2495(7) 0.0358(12) Uani 1 1 d . . .
H7A H 0.8813 0.3079 1.2886 0.054 Uiso 1 1 calc R . .
H7B H 0.6618 0.2162 1.1812 0.054 Uiso 1 1 calc R . .
H7C H 0.7380 0.4125 1.3565 0.054 Uiso 1 1 calc R . .
C6 C 0.7382(6) 0.3426(6) 0.8286(6) 0.0193(9) Uani 1 1 d . . .
C9 C 0.7267(7) 0.2193(6) 0.6365(6) 0.0294(11) Uani 1 1 d . . .
H9A H 0.8483 0.2448 0.6310 0.044 Uiso 1 1 calc R . .
H9B H 0.6333 0.2354 0.5519 0.044 Uiso 1 1 calc R . .
H9C H 0.6910 0.0980 0.6025 0.044 Uiso 1 1 calc R . .
C1 C 0.7429(6) 0.2872(6) 0.9489(6) 0.0219(10) Uani 1 1 d . . .
C2 C 0.7547(6) 0.3967(6) 1.1280(6) 0.0235(10) Uani 1 1 d . . .
C8 C 0.7649(7) 0.8314(6) 1.1492(6) 0.0326(12) Uani 1 1 d . . .
H8A H 0.6674 0.8378 1.0589 0.049 Uiso 1 1 calc R . .
H8B H 0.8871 0.8937 1.1705 0.049 Uiso 1 1 calc R . .
H8C H 0.7451 0.8855 1.2634 0.049 Uiso 1 1 calc R . .
C4 C 0.7572(6) 0.6397(6) 1.0786(6) 0.0215(9) Uani 1 1 d . . .
C3 C 0.7616(6) 0.5723(6) 1.1880(6) 0.0205(9) Uani 1 1 d . . .

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
Br3 0.0545(4) 0.0300(3) 0.0284(3) 0.0209(2) 0.0175(2) 0.0131(2)
Br2 0.0493(3) 0.0251(3) 0.0201(3) 0.0081(2) 0.0164(2) 0.0097(2)
Br1 0.0614(4) 0.0179(3) 0.0350(3) 0.0141(2) 0.0230(3) 0.0151(2)
C5 0.026(2) 0.023(3) 0.020(2) 0.014(2) 0.0070(19) 0.003(2)
C7 0.053(3) 0.036(3) 0.031(3) 0.023(3) 0.022(2) 0.018(3)
C6 0.019(2) 0.016(2) 0.018(2) 0.0069(19) 0.0058(17) 0.0039(18)
C9 0.046(3) 0.022(3) 0.024(2) 0.012(2) 0.017(2) 0.012(2)
C1 0.025(2) 0.011(2) 0.029(2) 0.011(2) 0.0097(19) 0.0069(19)
C2 0.029(2) 0.021(3) 0.019(2) 0.010(2) 0.0093(19) 0.009(2)
C8 0.051(3) 0.019(3) 0.026(3) 0.011(2) 0.017(2) 0.010(2)
C4 0.021(2) 0.017(2) 0.021(2) 0.008(2) 0.0061(18) 0.0032(19)
C3 0.026(2) 0.017(2) 0.015(2) 0.0062(19) 0.0083(18) 0.0057(19)

_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
Br3 C5 1.900(4) . ?
Br2 C3 1.900(4) . ?
Br1 C1 1.908(4) . ?
C5 C6 1.394(6) . ?
C5 C4 1.398(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C7 C2 1.514(6) . ?
C6 C9 1.503(6) . ?
C6 C1 1.406(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C1 C2 1.391(6) . ?
C2 C3 1.394(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C8 C4 1.513(6) . ?
C4 C3 1.396(6) . ?

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
C6 C5 Br3 117.1(3) . . ?
C6 C5 C4 124.4(4) . . ?
C4 C5 Br3 118.5(3) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
C5 C6 C9 122.5(4) . . ?
C5 C6 C1 115.1(4) . . ?
C1 C6 C9 122.4(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C1 Br1 118.0(3) . . ?
C2 C1 Br1 117.6(3) . . ?
C2 C1 C6 124.4(4) . . ?
C1 C2 C7 121.3(4) . . ?
C1 C2 C3 116.4(4) . . ?
C3 C2 C7 122.4(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C5 C4 C8 122.0(4) . . ?
C3 C4 C5 116.3(4) . . ?
C3 C4 C8 121.8(4) . . ?
C2 C3 Br2 118.7(3) . . ?
C2 C3 C4 123.5(4) . . ?
C4 C3 Br2 117.8(3) . . ?
####################################################################### 
# 
# 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_tbm-262K
_database_code_depnum_ccdc_archive 'CCDC 1057998'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
tribromomesitylene 
;
_chemical_formula_moiety         'C9 H9 Br3'
_chemical_formula_sum            'C9 H9 Br3'
_chemical_formula_weight         356.89
_chemical_melting_point          ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.7631(7)
_cell_length_b                   9.0805(8)
_cell_length_c                   9.0999(8)
_cell_angle_alpha                119.760(9)
_cell_angle_beta                 106.811(8)
_cell_angle_gamma                95.019(7)
_cell_volume                     512.06(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1396
_cell_measurement_temperature    262(2)
_cell_measurement_theta_max      28.9353
_cell_measurement_theta_min      3.6126
_exptl_absorpt_coefficient_mu    11.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4894
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.62
_diffrn_ambient_temperature      262(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9924
_diffrn_measured_fraction_theta_max 0.9330
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   50.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000    0.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   23.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -103.0000    7.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   48.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000 -120.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega  -35.00   51.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000  120.0000 86

#__ type_ start__ end____ width___ exp.time_
  5 omega  -62.00   10.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000  -90.0000 72

#__ type_ start__ end____ width___ exp.time_
  6 omega   -7.00   24.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega  -86.00  -61.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   88.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000  150.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0505032000
_diffrn_orient_matrix_UB_12      0.0459841000
_diffrn_orient_matrix_UB_13      0.0536084000
_diffrn_orient_matrix_UB_21      0.0764001000
_diffrn_orient_matrix_UB_22      0.0773691000
_diffrn_orient_matrix_UB_23      0.0531500000
_diffrn_orient_matrix_UB_31      -0.0385465000
_diffrn_orient_matrix_UB_32      0.0259632000
_diffrn_orient_matrix_UB_33      -0.0613437000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1786
_reflns_number_total             2342
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.984
_refine_diff_density_min         -1.086
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       0.0260(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0384P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1079
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H7A,H7B,H7C} of C7, {H9A,H9B,H9C} of C9, {H8A,H8B,H8C} of C8
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Br3 Br 0.73562(9) 0.60242(9) 0.74354(8) 0.0426(2) Uani 1 1 d . . .
Br2 Br 0.78245(8) 0.73035(8) 1.43177(7) 0.0406(2) Uani 1 1 d . . .
Br1 Br 0.73073(9) 0.04617(8) 0.86086(8) 0.0454(2) Uani 1 1 d . . .
C5 C 0.7447(6) 0.5216(8) 0.9016(7) 0.0281(12) Uani 1 1 d . . .
C7 C 0.7602(9) 0.3282(10) 1.2498(8) 0.0443(16) Uani 1 1 d . . .
H7A H 0.8804 0.3093 1.2881 0.066 Uiso 1 1 calc R . .
H7B H 0.6642 0.2187 1.1830 0.066 Uiso 1 1 calc R . .
H7C H 0.7394 0.4129 1.3556 0.066 Uiso 1 1 calc R . .
C6 C 0.7394(6) 0.3436(7) 0.8294(7) 0.0273(12) Uani 1 1 d . . .
C9 C 0.7263(8) 0.2204(8) 0.6362(7) 0.0370(14) Uani 1 1 d . . .
H9A H 0.8363 0.2605 0.6232 0.056 Uiso 1 1 calc R . .
H9B H 0.6174 0.2188 0.5513 0.056 Uiso 1 1 calc R . .
H9C H 0.7170 0.1034 0.6111 0.056 Uiso 1 1 calc R . .
C1 C 0.7433(7) 0.2890(7) 0.9483(7) 0.0280(11) Uani 1 1 d . . .
C2 C 0.7547(6) 0.3968(7) 1.1283(7) 0.0281(12) Uani 1 1 d . . .
C8 C 0.7643(8) 0.8309(8) 1.1477(8) 0.0376(13) Uani 1 1 d . . .
H8A H 0.6774 0.8379 1.0534 0.056 Uiso 1 1 calc R . .
H8B H 0.8886 0.8958 1.1814 0.056 Uiso 1 1 calc R . .
H8C H 0.7312 0.8804 1.2530 0.056 Uiso 1 1 calc R . .
C4 C 0.7578(6) 0.6418(7) 1.0779(7) 0.0263(11) Uani 1 1 d . . .
C3 C 0.7619(6) 0.5712(8) 1.1867(6) 0.0257(11) Uani 1 1 d . . .

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
Br3 0.0656(4) 0.0377(4) 0.0352(4) 0.0260(3) 0.0210(3) 0.0164(3)
Br2 0.0597(4) 0.0313(4) 0.0251(3) 0.0101(3) 0.0194(3) 0.0120(3)
Br1 0.0745(5) 0.0231(4) 0.0427(4) 0.0171(3) 0.0278(3) 0.0188(3)
C5 0.028(2) 0.033(4) 0.022(3) 0.016(3) 0.009(2) 0.009(2)
C7 0.060(4) 0.053(5) 0.037(3) 0.031(3) 0.025(3) 0.025(4)
C6 0.028(2) 0.023(3) 0.025(3) 0.011(3) 0.008(2) 0.006(2)
C9 0.050(3) 0.026(3) 0.020(3) 0.005(3) 0.011(2) 0.010(3)
C1 0.038(3) 0.018(3) 0.029(3) 0.014(2) 0.014(2) 0.009(2)
C2 0.033(3) 0.020(3) 0.026(3) 0.010(3) 0.010(2) 0.005(2)
C8 0.054(3) 0.021(3) 0.031(3) 0.009(3) 0.018(3) 0.011(3)
C4 0.026(2) 0.019(3) 0.023(2) 0.009(2) 0.004(2) 0.001(2)
C3 0.028(2) 0.026(3) 0.018(2) 0.010(2) 0.009(2) 0.006(2)

_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
Br3 C5 1.901(5) . ?
Br2 C3 1.908(5) . ?
Br1 C1 1.919(6) . ?
C5 C6 1.402(8) . ?
C5 C4 1.387(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 C2 1.508(7) . ?
C6 C9 1.509(7) . ?
C6 C1 1.390(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 C2 1.400(7) . ?
C2 C3 1.388(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C4 1.497(8) . ?
C4 C3 1.417(7) . ?

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
C6 C5 Br3 116.5(4) . . ?
C4 C5 Br3 118.2(4) . . ?
C4 C5 C6 125.3(5) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
C5 C6 C9 122.4(5) . . ?
C1 C6 C5 114.7(5) . . ?
C1 C6 C9 122.8(5) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C1 Br1 118.1(4) . . ?
C6 C1 C2 125.4(5) . . ?
C2 C1 Br1 116.5(4) . . ?
C1 C2 C7 122.3(5) . . ?
C3 C2 C7 122.6(5) . . ?
C3 C2 C1 115.1(5) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C5 C4 C8 122.8(5) . . ?
C5 C4 C3 114.8(5) . . ?
C3 C4 C8 122.4(5) . . ?
C2 C3 Br2 118.4(4) . . ?
C2 C3 C4 124.6(5) . . ?
C4 C3 Br2 117.0(4) . . ?

####################################################################### 
# 
# 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_tcm-118K
_database_code_depnum_ccdc_archive 'CCDC 1057999'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-27
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
trichloromesitylene 
;
_chemical_formula_moiety         'C9 H9 Cl3'
_chemical_formula_sum            'C9 H9 Cl3'
_chemical_formula_weight         223.51
_chemical_melting_point          ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.5031(5)
_cell_length_b                   8.7681(8)
_cell_length_c                   8.7862(7)
_cell_angle_alpha                119.731(9)
_cell_angle_beta                 106.219(6)
_cell_angle_gamma                95.510(7)
_cell_volume                     462.50(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2108
_cell_measurement_temperature    118.2(4)
_cell_measurement_theta_max      29.0168
_cell_measurement_theta_min      4.2105
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4431
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.08
_diffrn_reflns_theta_min         4.22
_diffrn_ambient_temperature      118.2(4)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9899
_diffrn_measured_fraction_theta_max 0.9251
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00   -3.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000 -150.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00    5.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00   35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000  120.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega    4.00   40.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -57.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  178.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
  7 omega   29.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -99.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega  -90.00   -8.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -19.0000   60.0000 82
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0449553000
_diffrn_orient_matrix_UB_12      -0.0926953000
_diffrn_orient_matrix_UB_13      -0.0373211000
_diffrn_orient_matrix_UB_21      -0.0144911000
_diffrn_orient_matrix_UB_22      0.0267674000
_diffrn_orient_matrix_UB_23      0.0851757000
_diffrn_orient_matrix_UB_31      -0.0910760000
_diffrn_orient_matrix_UB_32      0.0107355000
_diffrn_orient_matrix_UB_33      -0.0379206000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1899
_reflns_number_total             2133
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0424P)²+0.2551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0892
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H8A,H8B,H8C} of C8, {H7A,H7B,H7C} of C7, {H9A,H9B,H9C} of C9
2.a Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cl2 Cl 0.77537(7) 0.72377(7) 1.42576(6) 0.02001(14) Uani 1 1 d . . .
Cl1 Cl 0.73949(8) 0.05727(7) 0.86047(7) 0.02258(14) Uani 1 1 d . . .
Cl3 Cl 0.73315(8) 0.61148(7) 0.75300(7) 0.02235(14) Uani 1 1 d . . .
C2 C 0.7552(3) 0.3954(3) 1.1308(3) 0.0159(4) Uani 1 1 d . . .
C6 C 0.7385(3) 0.3467(3) 0.8241(3) 0.0153(4) Uani 1 1 d . . .
C4 C 0.7563(3) 0.6513(3) 1.0842(3) 0.0155(4) Uani 1 1 d . . .
C3 C 0.7606(3) 0.5770(3) 1.1937(3) 0.0148(4) Uani 1 1 d . . .
C1 C 0.7451(3) 0.2856(3) 0.9446(3) 0.0149(4) Uani 1 1 d . . .
C9 C 0.7250(3) 0.2224(3) 0.6232(3) 0.0202(4) Uani 1 1 d . . .
H9A H 0.7483 0.1098 0.6047 0.030 Uiso 1 1 calc R . .
H9B H 0.8199 0.2813 0.6008 0.030 Uiso 1 1 calc R . .
H9C H 0.5982 0.1971 0.5366 0.030 Uiso 1 1 calc R . .
C5 C 0.7438(3) 0.5301(3) 0.9000(3) 0.0149(4) Uani 1 1 d . . .
C7 C 0.7602(3) 0.3201(3) 1.2524(3) 0.0232(4) Uani 1 1 d . . .
H7A H 0.8731 0.2779 1.2693 0.035 Uiso 1 1 calc R . .
H7B H 0.6465 0.2199 1.1919 0.035 Uiso 1 1 calc R . .
H7C H 0.7642 0.4144 1.3735 0.035 Uiso 1 1 calc R . .
C8 C 0.7655(3) 0.8490(3) 1.1619(3) 0.0203(4) Uani 1 1 d . . .
H8A H 0.6592 0.8753 1.2016 0.030 Uiso 1 1 calc R . .
H8B H 0.7580 0.8735 1.0655 0.030 Uiso 1 1 calc R . .
H8C H 0.8852 0.9248 1.2682 0.030 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
Cl2 0.0276(3) 0.0176(3) 0.0130(2) 0.00608(19) 0.00942(19) 0.0071(2)
Cl1 0.0351(3) 0.0144(2) 0.0206(2) 0.0093(2) 0.0131(2) 0.0105(2)
Cl3 0.0342(3) 0.0206(3) 0.0181(2) 0.0136(2) 0.0114(2) 0.0093(2)
C2 0.0168(10) 0.0164(10) 0.0156(9) 0.0096(8) 0.0059(7) 0.0048(8)
C6 0.0131(9) 0.0157(9) 0.0143(9) 0.0066(8) 0.0047(7) 0.0037(7)
C4 0.0152(9) 0.0146(9) 0.0151(9) 0.0075(8) 0.0048(7) 0.0045(7)
C3 0.0157(9) 0.0153(9) 0.0108(8) 0.0055(7) 0.0050(7) 0.0036(7)
C1 0.0167(9) 0.0115(9) 0.0148(9) 0.0058(8) 0.0062(7) 0.0045(7)
C9 0.0256(11) 0.0205(10) 0.0150(9) 0.0084(8) 0.0105(8) 0.0078(8)
C5 0.0153(9) 0.0183(10) 0.0145(9) 0.0111(8) 0.0061(7) 0.0049(7)
C7 0.0349(12) 0.0223(11) 0.0200(10) 0.0145(9) 0.0139(9) 0.0107(9)
C8 0.0260(11) 0.0135(10) 0.0189(9) 0.0072(8) 0.0085(8) 0.0055(8)

_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
Cl2 C3 1.7520(18) . ?
Cl1 C1 1.7481(19) . ?
Cl3 C5 1.7465(19) . ?
C2 C3 1.395(3) . ?
C2 C1 1.402(3) . ?
C2 C7 1.503(3) . ?
C6 C1 1.395(3) . ?
C6 C9 1.511(3) . ?
C6 C5 1.394(3) . ?
C4 C3 1.400(3) . ?
C4 C5 1.396(3) . ?
C4 C8 1.501(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 115.37(17) . . ?
C3 C2 C7 123.04(17) . . ?
C1 C2 C7 121.58(18) . . ?
C1 C6 C9 122.48(17) . . ?
C5 C6 C1 115.81(17) . . ?
C5 C6 C9 121.71(17) . . ?
C3 C4 C8 121.68(17) . . ?
C5 C4 C3 115.69(17) . . ?
C5 C4 C8 122.63(17) . . ?
C2 C3 Cl2 118.23(14) . . ?
C2 C3 C4 124.45(17) . . ?
C4 C3 Cl2 117.32(14) . . ?
C2 C1 Cl1 116.88(14) . . ?
C6 C1 Cl1 118.71(14) . . ?
C6 C1 C2 124.41(18) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C5 Cl3 117.29(14) . . ?
C6 C5 C4 124.27(17) . . ?
C4 C5 Cl3 118.44(15) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
####################################################################### 
# 
# 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_tcm-154K
_database_code_depnum_ccdc_archive 'CCDC 1058000'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-27
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
trichloromesitylene  
;
_chemical_formula_moiety         'C9 H9 Cl3'
_chemical_formula_sum            'C9 H9 Cl3'
_chemical_formula_weight         223.51
_chemical_melting_point          ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.6629(5)
_cell_length_b                   8.7822(6)
_cell_length_c                   8.7994(7)
_cell_angle_alpha                119.644(8)
_cell_angle_beta                 107.474(7)
_cell_angle_gamma                96.230(6)
_cell_volume                     466.72(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1852
_cell_measurement_temperature    154(2)
_cell_measurement_theta_max      29.1490
_cell_measurement_theta_min      4.6386
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4529
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         4.65
_diffrn_ambient_temperature      154(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9932
_diffrn_measured_fraction_theta_max 0.9316
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -8.00   22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   16.00   52.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -88.00  -35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00    8.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega  -43.00   54.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000  120.0000 97

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00    2.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega  -44.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega  -37.00   51.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
 10 omega   -2.00   60.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585   57.0000  120.0000 62
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0450586000
_diffrn_orient_matrix_UB_12      0.0355491000
_diffrn_orient_matrix_UB_13      0.0990561000
_diffrn_orient_matrix_UB_21      0.0143660000
_diffrn_orient_matrix_UB_22      -0.0859196000
_diffrn_orient_matrix_UB_23      -0.0228702000
_diffrn_orient_matrix_UB_31      0.0904543000
_diffrn_orient_matrix_UB_32      0.0301368000
_diffrn_orient_matrix_UB_33      0.0012894000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1809
_reflns_number_total             2155
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.2218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0984
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H7A,H7B,H7C} of C7, {H8A,H8B,H8C} of C8, {H9A,H9B,H9C} of C9
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.73836(8) 0.09597(7) 0.74314(8) 0.02927(16) Uani 1 1 d . . .
Cl2 Cl 0.77565(8) 0.65743(7) 1.41311(7) 0.02827(16) Uani 1 1 d . . .
Cl3 Cl 0.73901(9) 0.75433(8) 0.84652(8) 0.03402(17) Uani 1 1 d . . .
C2 C 0.7570(3) 0.3881(3) 1.0720(3) 0.0219(4) Uani 1 1 d . . .
C4 C 0.7545(3) 0.6880(3) 1.1173(3) 0.0214(4) Uani 1 1 d . . .
C5 C 0.7439(3) 0.6121(3) 0.9325(3) 0.0219(4) Uani 1 1 d . . .
C6 C 0.7365(3) 0.4303(3) 0.8109(3) 0.0203(4) Uani 1 1 d . . .
C1 C 0.7451(3) 0.3239(3) 0.8881(3) 0.0215(4) Uani 1 1 d . . .
C7 C 0.7645(4) 0.2675(3) 1.1487(4) 0.0319(5) Uani 1 1 d . . .
H7A H 0.7853 0.1536 1.0619 0.048 Uiso 1 1 calc R . .
H7B H 0.6427 0.2375 1.1579 0.048 Uiso 1 1 calc R . .
H7C H 0.8705 0.3332 1.2760 0.048 Uiso 1 1 calc R . .
C8 C 0.7625(3) 0.8865(3) 1.2423(3) 0.0287(5) Uani 1 1 d . . .
H8A H 0.8905 0.9681 1.2886 0.043 Uiso 1 1 calc R . .
H8B H 0.7369 0.9049 1.3519 0.043 Uiso 1 1 calc R . .
H8C H 0.6653 0.9149 1.1674 0.043 Uiso 1 1 calc R . .
C3 C 0.7610(3) 0.5713(3) 1.1816(3) 0.0206(4) Uani 1 1 d . . .
C9 C 0.7208(3) 0.3540(3) 0.6102(3) 0.0280(5) Uani 1 1 d . . .
H9A H 0.6635 0.4257 0.5641 0.042 Uiso 1 1 calc R . .
H9B H 0.6394 0.2249 0.5258 0.042 Uiso 1 1 calc R . .
H9C H 0.8493 0.3615 0.6100 0.042 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
Cl1 0.0417(3) 0.0195(3) 0.0244(3) 0.0093(2) 0.0154(2) 0.0120(2)
Cl2 0.0383(3) 0.0300(3) 0.0176(3) 0.0123(2) 0.0140(2) 0.0118(2)
Cl3 0.0560(4) 0.0289(3) 0.0291(3) 0.0210(3) 0.0213(3) 0.0177(3)
C2 0.0235(10) 0.0222(10) 0.0200(10) 0.0118(9) 0.0087(8) 0.0077(8)
C4 0.0212(9) 0.0196(9) 0.0190(10) 0.0085(8) 0.0074(8) 0.0055(8)
C5 0.0241(10) 0.0224(10) 0.0208(11) 0.0135(9) 0.0083(8) 0.0067(8)
C6 0.0195(9) 0.0216(10) 0.0172(10) 0.0093(8) 0.0077(8) 0.0046(8)
C1 0.0212(10) 0.0187(9) 0.0197(10) 0.0075(8) 0.0084(8) 0.0064(8)
C7 0.0475(14) 0.0295(12) 0.0280(12) 0.0201(10) 0.0182(11) 0.0144(10)
C8 0.0383(12) 0.0217(10) 0.0249(12) 0.0111(9) 0.0140(10) 0.0116(9)
C3 0.0211(9) 0.0238(10) 0.0139(9) 0.0087(8) 0.0070(7) 0.0060(8)
C9 0.0361(12) 0.0283(11) 0.0185(11) 0.0116(9) 0.0126(9) 0.0099(9)

_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
Cl1 C1 1.746(2) . ?
Cl2 C3 1.748(2) . ?
Cl3 C5 1.750(2) . ?
C2 C1 1.394(3) . ?
C2 C7 1.509(3) . ?
C2 C3 1.399(3) . ?
C4 C5 1.390(3) . ?
C4 C8 1.514(3) . ?
C4 C3 1.393(3) . ?
C5 C6 1.397(3) . ?
C6 C1 1.397(3) . ?
C6 C9 1.506(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 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C1 C2 C7 122.21(19) . . ?
C1 C2 C3 116.00(19) . . ?
C3 C2 C7 121.8(2) . . ?
C5 C4 C8 121.98(19) . . ?
C5 C4 C3 115.92(19) . . ?
C3 C4 C8 122.09(19) . . ?
C4 C5 Cl3 117.63(16) . . ?
C4 C5 C6 124.50(19) . . ?
C6 C5 Cl3 117.88(16) . . ?
C5 C6 C9 122.30(19) . . ?
C1 C6 C5 115.53(19) . . ?
C1 C6 C9 122.17(19) . . ?
C2 C1 Cl1 118.33(16) . . ?
C2 C1 C6 124.11(19) . . ?
C6 C1 Cl1 117.56(16) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C3 Cl2 117.55(16) . . ?
C4 C3 Cl2 118.52(16) . . ?
C4 C3 C2 123.9(2) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
####################################################################### 
# 
# 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_tcm-190K
_database_code_depnum_ccdc_archive 'CCDC 1058001'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-27
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
trichloromesitylene  
;
_chemical_formula_moiety         'C9 H9 Cl3'
_chemical_formula_sum            'C9 H9 Cl3'
_chemical_formula_weight         223.51
_chemical_melting_point          ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.6799(5)
_cell_length_b                   8.7893(7)
_cell_length_c                   8.8083(7)
_cell_angle_alpha                119.651(8)
_cell_angle_beta                 107.294(7)
_cell_angle_gamma                96.335(6)
_cell_volume                     469.02(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1786
_cell_measurement_temperature    189.95(10)
_cell_measurement_theta_max      29.2838
_cell_measurement_theta_min      4.6297
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4530
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.35
_diffrn_reflns_theta_min         4.64
_diffrn_ambient_temperature      189.95(10)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9937
_diffrn_measured_fraction_theta_max 0.9372
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00   -3.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega  -90.00    3.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000  -60.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00   35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000  120.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega    4.00   40.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -57.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  178.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega   29.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -99.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega  -90.00  -10.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -19.0000   60.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0449883000
_diffrn_orient_matrix_UB_12      0.0355606000
_diffrn_orient_matrix_UB_13      0.0988385000
_diffrn_orient_matrix_UB_21      0.0142398000
_diffrn_orient_matrix_UB_22      -0.0858797000
_diffrn_orient_matrix_UB_23      -0.0228936000
_diffrn_orient_matrix_UB_31      0.0901462000
_diffrn_orient_matrix_UB_32      0.0300211000
_diffrn_orient_matrix_UB_33      0.0009411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1753
_reflns_number_total             2164
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0481P)²+0.1559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1066
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H7A,H7B,H7C} of C7, {H8A,H8B,H8C} of C8, {H9A,H9B,H9C} of C9
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.73955(9) 0.09647(7) 0.74399(9) 0.03613(18) Uani 1 1 d . . .
Cl2 Cl 0.77703(9) 0.65735(8) 1.41284(8) 0.03484(18) Uani 1 1 d . . .
Cl3 Cl 0.73612(11) 0.75273(8) 0.84587(9) 0.0417(2) Uani 1 1 d . . .
C2 C 0.7578(3) 0.3880(3) 1.0726(3) 0.0258(4) Uani 1 1 d . . .
C4 C 0.7545(3) 0.6871(3) 1.1174(3) 0.0249(4) Uani 1 1 d . . .
C5 C 0.7426(3) 0.6111(3) 0.9319(3) 0.0262(5) Uani 1 1 d . . .
C6 C 0.7362(3) 0.4296(3) 0.8111(3) 0.0245(4) Uani 1 1 d . . .
C1 C 0.7447(3) 0.3241(3) 0.8879(3) 0.0249(4) Uani 1 1 d . . .
C7 C 0.7666(4) 0.2680(4) 1.1485(4) 0.0386(6) Uani 1 1 d . . .
H7A H 0.6451 0.2314 1.1503 0.058 Uiso 1 1 calc R . .
H7B H 0.8650 0.3352 1.2760 0.058 Uiso 1 1 calc R . .
H7C H 0.7954 0.1605 1.0677 0.058 Uiso 1 1 calc R . .
C8 C 0.7615(4) 0.8856(3) 1.2416(4) 0.0342(5) Uani 1 1 d . . .
H8A H 0.8845 0.9660 1.2822 0.051 Uiso 1 1 calc R . .
H8B H 0.7417 0.9051 1.3517 0.051 Uiso 1 1 calc R . .
H8C H 0.6627 0.9112 1.1696 0.051 Uiso 1 1 calc R . .
C3 C 0.7614(3) 0.5708(3) 1.1812(3) 0.0248(4) Uani 1 1 d . . .
C9 C 0.7199(4) 0.3536(3) 0.6100(3) 0.0344(5) Uani 1 1 d . . .
H9A H 0.6628 0.2222 0.5334 0.052 Uiso 1 1 calc R . .
H9B H 0.8453 0.3832 0.6126 0.052 Uiso 1 1 calc R . .
H9C H 0.6412 0.4069 0.5561 0.052 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
Cl1 0.0504(4) 0.0235(3) 0.0305(3) 0.0107(2) 0.0186(3) 0.0142(2)
Cl2 0.0465(4) 0.0363(3) 0.0217(3) 0.0144(3) 0.0166(3) 0.0141(3)
Cl3 0.0672(5) 0.0352(3) 0.0364(4) 0.0256(3) 0.0255(3) 0.0214(3)
C2 0.0266(11) 0.0279(10) 0.0237(11) 0.0148(9) 0.0100(9) 0.0094(9)
C4 0.0233(11) 0.0232(10) 0.0229(11) 0.0103(9) 0.0080(9) 0.0058(8)
C5 0.0295(11) 0.0254(10) 0.0248(11) 0.0151(9) 0.0106(9) 0.0086(9)
C6 0.0233(11) 0.0265(10) 0.0207(10) 0.0111(9) 0.0093(9) 0.0068(8)
C1 0.0242(11) 0.0221(10) 0.0225(11) 0.0087(9) 0.0089(9) 0.0073(8)
C7 0.0576(17) 0.0349(12) 0.0334(13) 0.0237(11) 0.0208(13) 0.0179(12)
C8 0.0456(15) 0.0244(10) 0.0284(12) 0.0111(10) 0.0155(11) 0.0138(10)
C3 0.0231(11) 0.0286(11) 0.0191(10) 0.0115(9) 0.0081(9) 0.0069(9)
C9 0.0449(15) 0.0341(12) 0.0228(12) 0.0135(10) 0.0164(11) 0.0122(11)

_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
Cl1 C1 1.747(2) . ?
Cl2 C3 1.748(2) . ?
Cl3 C5 1.747(2) . ?
C2 C1 1.399(3) . ?
C2 C7 1.501(3) . ?
C2 C3 1.397(3) . ?
C4 C5 1.393(3) . ?
C4 C8 1.516(3) . ?
C4 C3 1.388(3) . ?
C5 C6 1.397(3) . ?
C6 C1 1.390(3) . ?
C6 C9 1.509(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C7 122.2(2) . . ?
C3 C2 C1 115.5(2) . . ?
C3 C2 C7 122.3(2) . . ?
C5 C4 C8 121.7(2) . . ?
C3 C4 C5 115.93(19) . . ?
C3 C4 C8 122.4(2) . . ?
C4 C5 Cl3 117.69(16) . . ?
C4 C5 C6 124.3(2) . . ?
C6 C5 Cl3 118.06(17) . . ?
C5 C6 C9 122.0(2) . . ?
C1 C6 C5 115.6(2) . . ?
C1 C6 C9 122.44(19) . . ?
C2 C1 Cl1 117.97(17) . . ?
C6 C1 Cl1 117.60(16) . . ?
C6 C1 C2 124.42(19) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C3 Cl2 117.36(17) . . ?
C4 C3 Cl2 118.35(16) . . ?
C4 C3 C2 124.3(2) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
####################################################################### 
# 
# 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_tcm-226K
_database_code_depnum_ccdc_archive 'CCDC 1058002'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-27
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
trichloromesitylene  
;
_chemical_formula_moiety         'C9 H9 Cl3'
_chemical_formula_sum            'C9 H9 Cl3'
_chemical_formula_weight         223.51
_chemical_melting_point          ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.7076(10)
_cell_length_b                   8.8010(8)
_cell_length_c                   8.8248(8)
_cell_angle_alpha                119.644(10)
_cell_angle_beta                 107.231(10)
_cell_angle_gamma                96.278(9)
_cell_volume                     472.73(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1649
_cell_measurement_temperature    226(2)
_cell_measurement_theta_max      29.2379
_cell_measurement_theta_min      4.1818
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4591
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.30
_diffrn_reflns_theta_min         4.19
_diffrn_ambient_temperature      226(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9953
_diffrn_measured_fraction_theta_max 0.9531
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -81.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega   11.00   37.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -71.00  -35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega  -37.00  -11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -73.00  -35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega  -87.00    8.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega   -3.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585   77.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega    7.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585 -101.0000   15.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   -2.00   48.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585   57.0000    0.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0457459000
_diffrn_orient_matrix_UB_12      0.0353102000
_diffrn_orient_matrix_UB_13      0.0984435000
_diffrn_orient_matrix_UB_21      0.0134420000
_diffrn_orient_matrix_UB_22      -0.0861259000
_diffrn_orient_matrix_UB_23      -0.0233320000
_diffrn_orient_matrix_UB_31      0.0893565000
_diffrn_orient_matrix_UB_32      0.0289356000
_diffrn_orient_matrix_UB_33      -0.0003874000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1748
_reflns_number_total             2196
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.1535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1096
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H8A,H8B,H8C} of C8, {H7A,H7B,H7C} of C7, {H9A,H9B,H9C} of C9
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.74043(10) 0.09720(8) 0.74494(9) 0.04332(19) Uani 1 1 d . . .
Cl2 Cl 0.77809(9) 0.65743(8) 1.41241(8) 0.04184(19) Uani 1 1 d . . .
Cl3 Cl 0.73410(11) 0.75128(9) 0.84519(9) 0.0496(2) Uani 1 1 d . . .
C2 C 0.7584(3) 0.3884(3) 1.0723(3) 0.0308(5) Uani 1 1 d . . .
C4 C 0.7547(3) 0.6869(3) 1.1175(3) 0.0306(5) Uani 1 1 d . . .
C5 C 0.7419(3) 0.6103(3) 0.9315(3) 0.0307(5) Uani 1 1 d . . .
C6 C 0.7359(3) 0.4297(3) 0.8115(3) 0.0295(5) Uani 1 1 d . . .
C1 C 0.7454(3) 0.3241(3) 0.8883(3) 0.0300(5) Uani 1 1 d . . .
C7 C 0.7680(4) 0.2676(4) 1.1489(4) 0.0459(6) Uani 1 1 d . . .
H7A H 0.7950 0.1583 1.0662 0.069 Uiso 1 1 calc R . .
H7B H 0.6466 0.2323 1.1531 0.069 Uiso 1 1 calc R . .
H7C H 0.8684 0.3347 1.2764 0.069 Uiso 1 1 calc R . .
C8 C 0.7605(4) 0.8841(3) 1.2408(4) 0.0409(6) Uani 1 1 d . . .
H8A H 0.8817 0.9657 1.2769 0.061 Uiso 1 1 calc R . .
H8B H 0.7463 0.9050 1.3546 0.061 Uiso 1 1 calc R . .
H8C H 0.6572 0.9081 1.1701 0.061 Uiso 1 1 calc R . .
C3 C 0.7621(3) 0.5701(3) 1.1807(3) 0.0294(5) Uani 1 1 d . . .
C9 C 0.7194(4) 0.3533(3) 0.6105(3) 0.0404(6) Uani 1 1 d . . .
H9A H 0.6209 0.3875 0.5475 0.061 Uiso 1 1 calc R . .
H9B H 0.6862 0.2205 0.5407 0.061 Uiso 1 1 calc R . .
H9C H 0.8405 0.4031 0.6144 0.061 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
Cl1 0.0619(4) 0.0272(3) 0.0358(3) 0.0119(3) 0.0230(3) 0.0163(3)
Cl2 0.0581(4) 0.0436(4) 0.0242(3) 0.0166(3) 0.0205(3) 0.0172(3)
Cl3 0.0810(5) 0.0419(4) 0.0421(4) 0.0299(3) 0.0306(3) 0.0252(3)
C2 0.0350(12) 0.0311(11) 0.0272(11) 0.0165(9) 0.0130(9) 0.0110(9)
C4 0.0321(12) 0.0277(10) 0.0255(11) 0.0109(9) 0.0112(9) 0.0078(9)
C5 0.0345(12) 0.0305(11) 0.0283(11) 0.0171(10) 0.0128(9) 0.0099(9)
C6 0.0308(11) 0.0299(11) 0.0228(10) 0.0115(9) 0.0114(9) 0.0072(9)
C1 0.0329(12) 0.0264(10) 0.0252(11) 0.0106(9) 0.0118(9) 0.0092(9)
C7 0.0680(18) 0.0413(14) 0.0401(14) 0.0280(12) 0.0250(13) 0.0199(13)
C8 0.0540(16) 0.0289(11) 0.0327(13) 0.0116(10) 0.0181(11) 0.0146(11)
C3 0.0322(12) 0.0329(11) 0.0209(10) 0.0128(9) 0.0119(9) 0.0101(9)
C9 0.0531(15) 0.0401(13) 0.0242(12) 0.0141(11) 0.0182(11) 0.0135(11)

_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
Cl1 C1 1.745(2) . ?
Cl2 C3 1.750(2) . ?
Cl3 C5 1.746(2) . ?
C2 C1 1.396(3) . ?
C2 C7 1.513(3) . ?
C2 C3 1.391(3) . ?
C4 C5 1.397(3) . ?
C4 C8 1.511(3) . ?
C4 C3 1.389(3) . ?
C5 C6 1.393(3) . ?
C6 C1 1.392(3) . ?
C6 C9 1.511(3) . ?
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 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 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
C1 C2 C7 121.9(2) . . ?
C3 C2 C1 115.9(2) . . ?
C3 C2 C7 122.2(2) . . ?
C5 C4 C8 121.8(2) . . ?
C3 C4 C5 115.6(2) . . ?
C3 C4 C8 122.6(2) . . ?
C4 C5 Cl3 117.61(17) . . ?
C6 C5 Cl3 118.10(17) . . ?
C6 C5 C4 124.3(2) . . ?
C5 C6 C9 122.0(2) . . ?
C1 C6 C5 115.8(2) . . ?
C1 C6 C9 122.2(2) . . ?
C2 C1 Cl1 118.21(17) . . ?
C6 C1 Cl1 117.74(16) . . ?
C6 C1 C2 124.0(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C3 Cl2 117.66(17) . . ?
C4 C3 Cl2 117.95(17) . . ?
C4 C3 C2 124.4(2) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
####################################################################### 
# 
# 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_tcm-262K
_database_code_depnum_ccdc_archive 'CCDC 1058003'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-27
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
trichloromesitylene  
;
_chemical_formula_moiety         'C9 H9 Cl3'
_chemical_formula_sum            'C9 H9 Cl3'
_chemical_formula_weight         223.51
_chemical_melting_point          ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.7324(5)
_cell_length_b                   8.8179(7)
_cell_length_c                   8.8415(6)
_cell_angle_alpha                119.640(8)
_cell_angle_beta                 107.114(6)
_cell_angle_gamma                96.298(6)
_cell_volume                     476.54(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1830
_cell_measurement_temperature    262.00(14)
_cell_measurement_theta_max      29.0946
_cell_measurement_theta_min      4.1656
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5280
_diffrn_reflns_theta_full        29.16
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         4.17
_diffrn_ambient_temperature      262.00(14)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9536
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00    4.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   36.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   61.0000   77.4790 68

#__ type_ start__ end____ width___ exp.time_
  3 omega  -92.00  -45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega  -40.00   22.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000 -120.0000 62

#__ type_ start__ end____ width___ exp.time_
  6 omega  -80.00    1.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000 -120.0000 81

#__ type_ start__ end____ width___ exp.time_
  7 omega  -90.00   21.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397    0.0000 -120.0000 111

#__ type_ start__ end____ width___ exp.time_
  8 omega  -39.00  -14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   -7.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585   37.0000 -180.0000 99
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0421606000
_diffrn_orient_matrix_UB_12      0.0363617000
_diffrn_orient_matrix_UB_13      0.0986645000
_diffrn_orient_matrix_UB_21      0.0196846000
_diffrn_orient_matrix_UB_22      -0.0831964000
_diffrn_orient_matrix_UB_23      -0.0206322000
_diffrn_orient_matrix_UB_31      0.0894855000
_diffrn_orient_matrix_UB_32      0.0348504000
_diffrn_orient_matrix_UB_33      0.0039221000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1749
_reflns_number_total             2236
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.1252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1157
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H9A,H9B,H9C} of C9, {H8A,H8B,H8C} of C8, {H7A,H7B,H7C} of C7
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.74073(10) 0.09785(8) 0.74587(9) 0.0486(2) Uani 1 1 d . . .
Cl2 Cl 0.77926(10) 0.65747(9) 1.41177(8) 0.0471(2) Uani 1 1 d . . .
Cl3 Cl 0.73277(12) 0.74995(9) 0.84469(10) 0.0561(2) Uani 1 1 d . . .
C2 C 0.7589(3) 0.3885(3) 1.0727(3) 0.0326(5) Uani 1 1 d . . .
C4 C 0.7540(3) 0.6859(3) 1.1164(3) 0.0319(5) Uani 1 1 d . . .
C5 C 0.7417(3) 0.6099(3) 0.9316(3) 0.0336(5) Uani 1 1 d . . .
C6 C 0.7359(3) 0.4297(3) 0.8118(3) 0.0321(5) Uani 1 1 d . . .
C1 C 0.7464(3) 0.3246(3) 0.8890(3) 0.0323(5) Uani 1 1 d . . .
C7 C 0.7698(5) 0.2690(4) 1.1492(4) 0.0515(7) Uani 1 1 d . . .
H7A H 0.8002 0.1628 1.0695 0.077 Uiso 1 1 calc R . .
H7B H 0.6495 0.2312 1.1509 0.077 Uiso 1 1 calc R . .
H7C H 0.8668 0.3367 1.2762 0.077 Uiso 1 1 calc R . .
C8 C 0.7607(4) 0.8834(3) 1.2403(4) 0.0447(6) Uani 1 1 d . . .
H8A H 0.8844 0.9632 1.2850 0.067 Uiso 1 1 calc R . .
H8B H 0.7352 0.9013 1.3469 0.067 Uiso 1 1 calc R . .
H8C H 0.6665 0.9110 1.1673 0.067 Uiso 1 1 calc R . .
C3 C 0.7629(3) 0.5707(3) 1.1806(3) 0.0315(5) Uani 1 1 d . . .
C9 C 0.7198(4) 0.3533(4) 0.6115(3) 0.0447(6) Uani 1 1 d . . .
H9A H 0.6245 0.3890 0.5500 0.067 Uiso 1 1 calc R . .
H9B H 0.6847 0.2220 0.5420 0.067 Uiso 1 1 calc R . .
H9C H 0.8400 0.4004 0.6150 0.067 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
Cl1 0.0691(5) 0.0305(3) 0.0406(4) 0.0137(3) 0.0251(3) 0.0189(3)
Cl2 0.0649(5) 0.0496(4) 0.0268(3) 0.0188(3) 0.0224(3) 0.0192(3)
Cl3 0.0919(6) 0.0482(4) 0.0487(4) 0.0357(3) 0.0343(4) 0.0296(4)
C2 0.0360(12) 0.0349(12) 0.0298(11) 0.0195(10) 0.0134(9) 0.0123(9)
C4 0.0318(12) 0.0298(11) 0.0290(11) 0.0131(9) 0.0120(9) 0.0090(9)
C5 0.0365(12) 0.0344(12) 0.0315(11) 0.0196(10) 0.0132(9) 0.0108(10)
C6 0.0340(12) 0.0340(12) 0.0234(10) 0.0132(9) 0.0115(9) 0.0076(9)
C1 0.0342(12) 0.0283(11) 0.0284(11) 0.0115(9) 0.0128(9) 0.0103(9)
C7 0.079(2) 0.0436(14) 0.0444(15) 0.0302(13) 0.0281(14) 0.0236(14)
C8 0.0590(17) 0.0322(12) 0.0352(13) 0.0125(11) 0.0200(12) 0.0165(11)
C3 0.0328(12) 0.0350(12) 0.0228(10) 0.0137(9) 0.0113(9) 0.0091(9)
C9 0.0575(17) 0.0456(14) 0.0263(12) 0.0161(11) 0.0186(11) 0.0146(12)

_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
Cl1 C1 1.746(2) . ?
Cl2 C3 1.749(2) . ?
Cl3 C5 1.746(2) . ?
C2 C1 1.398(3) . ?
C2 C7 1.506(3) . ?
C2 C3 1.396(3) . ?
C4 C5 1.392(3) . ?
C4 C8 1.515(3) . ?
C4 C3 1.386(3) . ?
C5 C6 1.393(3) . ?
C6 C1 1.393(3) . ?
C6 C9 1.510(3) . ?

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
C1 C2 C7 122.1(2) . . ?
C3 C2 C1 115.6(2) . . ?
C3 C2 C7 122.4(2) . . ?
C5 C4 C8 121.9(2) . . ?
C3 C4 C5 115.9(2) . . ?
C3 C4 C8 122.2(2) . . ?
C4 C5 Cl3 117.74(18) . . ?
C4 C5 C6 124.3(2) . . ?
C6 C5 Cl3 117.94(17) . . ?
C5 C6 C9 122.2(2) . . ?
C1 C6 C5 115.66(19) . . ?
C1 C6 C9 122.1(2) . . ?
C2 C1 Cl1 118.04(18) . . ?
C6 C1 Cl1 117.77(16) . . ?
C6 C1 C2 124.2(2) . . ?
C2 C3 Cl2 117.31(17) . . ?
C4 C3 Cl2 118.32(16) . . ?
C4 C3 C2 124.37(19) . . ?
####################################################################### 
# 
# 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_tim-118K
_database_code_depnum_ccdc_archive 'CCDC 1058004'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-08-18
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
triiodomesitylene  
;
_chemical_formula_moiety         'C9 H9 I3'
_chemical_formula_sum            'C9 H9 I3'
_chemical_formula_weight         497.86
_chemical_melting_point          ?

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.9189(5)
_cell_length_b                   9.5531(6)
_cell_length_c                   9.5594(6)
_cell_angle_alpha                60.255(6)
_cell_angle_beta                 66.670(6)
_cell_angle_gamma                85.526(5)
_cell_volume                     570.14(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2720
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      29.1839
_cell_measurement_theta_min      4.4913
_exptl_absorpt_coefficient_mu    8.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.900
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5431
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.25
_diffrn_reflns_theta_min         4.50
_diffrn_ambient_temperature      118(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9935
_diffrn_measured_fraction_theta_max 0.9394
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   11.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   21.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega   -7.00   65.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   77.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
  4 omega   -6.00   89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   37.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega  -50.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366  -37.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   73.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   77.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega  -94.00  -32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  178.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega   32.00   77.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366 -178.0000   60.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0539826000
_diffrn_orient_matrix_UB_12      0.0782334000
_diffrn_orient_matrix_UB_13      -0.0628329000
_diffrn_orient_matrix_UB_21      0.0401823000
_diffrn_orient_matrix_UB_22      -0.0250426000
_diffrn_orient_matrix_UB_23      -0.0632303000
_diffrn_orient_matrix_UB_31      -0.0721214000
_diffrn_orient_matrix_UB_32      0.0270276000
_diffrn_orient_matrix_UB_33      -0.0292828000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2361
_reflns_number_total             2614
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         1.031
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0260P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0642
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H9A,H9B,H9C} of C9, {H7A,H7B,H7C} of C7, {H8A,H8B,H8C} of C8
2.a Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
I2 I 0.25948(5) 0.85296(4) 0.22956(4) 0.01648(10) Uani 1 1 d . . .
I1 I 0.20495(5) 0.30044(4) 0.94047(4) 0.01730(10) Uani 1 1 d . . .
I3 I 0.28422(5) 0.16362(4) 0.36583(5) 0.01945(10) Uani 1 1 d . . .
C6 C 0.2510(6) 0.2709(6) 0.6250(7) 0.0134(10) Uani 1 1 d . . .
C8 C 0.2787(7) 0.5575(7) 0.1544(7) 0.0181(11) Uani 1 1 d . . .
H8A H 0.1841 0.6282 0.1343 0.027 Uiso 1 1 calc R . .
H8B H 0.2574 0.4640 0.1440 0.027 Uiso 1 1 calc R . .
H8C H 0.4024 0.6190 0.0662 0.027 Uiso 1 1 calc R . .
C2 C 0.2398(7) 0.5533(6) 0.5702(7) 0.0147(10) Uani 1 1 d . . .
C3 C 0.2536(6) 0.6023(6) 0.4011(6) 0.0125(10) Uani 1 1 d . . .
C9 C 0.2492(8) 0.0945(6) 0.7439(7) 0.0212(12) Uani 1 1 d . . .
H9A H 0.2859 0.0816 0.8359 0.032 Uiso 1 1 calc R . .
H9B H 0.3369 0.0506 0.6748 0.032 Uiso 1 1 calc R . .
H9C H 0.1238 0.0354 0.7993 0.032 Uiso 1 1 calc R . .
C7 C 0.2255(8) 0.6710(7) 0.6337(7) 0.0202(12) Uani 1 1 d . . .
H7A H 0.3503 0.7247 0.5918 0.030 Uiso 1 1 calc R . .
H7B H 0.1670 0.6120 0.7633 0.030 Uiso 1 1 calc R . .
H7C H 0.1501 0.7532 0.5876 0.030 Uiso 1 1 calc R . .
C4 C 0.2666(6) 0.4979(6) 0.3365(6) 0.0131(10) Uani 1 1 d . . .
C1 C 0.2357(6) 0.3856(6) 0.6783(6) 0.0137(10) Uani 1 1 d . . .
C5 C 0.2666(6) 0.3324(6) 0.4519(6) 0.0127(10) Uani 1 1 d . . .

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
I2 0.02573(18) 0.00836(16) 0.01293(18) -0.00318(14) -0.00874(14) 0.00253(14)
I1 0.02788(18) 0.01578(18) 0.01051(18) -0.00667(15) -0.01043(14) 0.00566(15)
I3 0.0345(2) 0.01362(18) 0.0181(2) -0.01119(16) -0.01450(16) 0.00695(16)
C6 0.016(2) 0.011(3) 0.013(3) -0.006(2) -0.006(2) 0.003(2)
C8 0.025(3) 0.019(3) 0.010(3) -0.007(2) -0.009(2) 0.003(2)
C2 0.018(2) 0.012(3) 0.013(3) -0.006(2) -0.005(2) 0.002(2)
C3 0.014(2) 0.009(2) 0.009(2) -0.001(2) -0.0044(19) 0.002(2)
C9 0.037(3) 0.010(3) 0.020(3) -0.006(2) -0.017(3) 0.005(3)
C7 0.037(3) 0.017(3) 0.016(3) -0.011(2) -0.016(3) 0.009(3)
C4 0.017(2) 0.014(3) 0.009(3) -0.006(2) -0.006(2) 0.000(2)
C1 0.015(2) 0.017(3) 0.007(3) -0.004(2) -0.005(2) 0.002(2)
C5 0.015(2) 0.012(2) 0.012(3) -0.007(2) -0.005(2) 0.003(2)

_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
I2 C3 2.118(5) . ?
I1 C1 2.128(5) . ?
I3 C5 2.118(5) . ?
C6 C9 1.490(7) . ?
C6 C1 1.400(7) . ?
C6 C5 1.408(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C4 1.502(7) . ?
C2 C3 1.400(7) . ?
C2 C7 1.500(7) . ?
C2 C1 1.406(7) . ?
C3 C4 1.389(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 C5 1.410(7) . ?

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
C1 C6 C9 122.3(4) . . ?
C1 C6 C5 115.7(4) . . ?
C5 C6 C9 122.0(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C3 C2 C7 122.4(4) . . ?
C3 C2 C1 115.5(4) . . ?
C1 C2 C7 122.1(4) . . ?
C2 C3 I2 118.1(3) . . ?
C4 C3 I2 117.4(3) . . ?
C4 C3 C2 124.5(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C8 122.0(5) . . ?
C3 C4 C5 116.3(4) . . ?
C5 C4 C8 121.7(4) . . ?
C6 C1 I1 117.8(4) . . ?
C6 C1 C2 124.4(4) . . ?
C2 C1 I1 117.7(3) . . ?
C6 C5 I3 117.4(4) . . ?
C6 C5 C4 123.5(4) . . ?
C4 C5 I3 119.0(3) . . ?
####################################################################### 
# 
# 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_tim-154K
_database_code_depnum_ccdc_archive 'CCDC 1058005'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-08-18
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
triiodomesitylene   
;
_chemical_formula_moiety         'C9 H9 I3'
_chemical_formula_sum            'C9 H9 I3'
_chemical_formula_weight         497.86
_chemical_melting_point          ?

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.9431(4)
_cell_length_b                   9.5681(6)
_cell_length_c                   9.5753(5)
_cell_angle_alpha                60.225(6)
_cell_angle_beta                 66.662(5)
_cell_angle_gamma                85.520(4)
_cell_volume                     573.52(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2905
_cell_measurement_temperature    154(2)
_cell_measurement_theta_max      29.1005
_cell_measurement_theta_min      4.2677
_exptl_absorpt_coefficient_mu    8.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.883
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6137
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         4.28
_diffrn_ambient_temperature      154(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9944
_diffrn_measured_fraction_theta_max 0.9440
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00   -7.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   20.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   17.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -93.00  -35.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   21.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  6 omega  -88.00  -58.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega  -90.00   24.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -19.0000 -150.0000 114

#__ type_ start__ end____ width___ exp.time_
  8 omega  -39.00   21.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega  -53.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -37.0000 -180.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0538363000
_diffrn_orient_matrix_UB_12      0.0781486000
_diffrn_orient_matrix_UB_13      -0.0627063000
_diffrn_orient_matrix_UB_21      0.0401776000
_diffrn_orient_matrix_UB_22      -0.0249522000
_diffrn_orient_matrix_UB_23      -0.0631533000
_diffrn_orient_matrix_UB_31      -0.0718335000
_diffrn_orient_matrix_UB_32      0.0270135000
_diffrn_orient_matrix_UB_33      -0.0293346000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2391
_reflns_number_total             2655
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.816
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.202
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0299P)²+0.6802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0693
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H7A,H7B,H7C} of C7, {H9A,H9B,H9C} of C9, {H8A,H8B,H8C} of C8
2.a Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
I2 I 0.25975(5) 0.85287(4) 0.22983(4) 0.02163(10) Uani 1 1 d . . .
I1 I 0.20485(5) 0.30096(4) 0.94009(4) 0.02258(10) Uani 1 1 d . . .
I3 I 0.28418(5) 0.16428(4) 0.36604(4) 0.02511(10) Uani 1 1 d . . .
C6 C 0.2503(6) 0.2717(6) 0.6249(6) 0.0154(9) Uani 1 1 d . . .
C8 C 0.2783(8) 0.5573(7) 0.1551(7) 0.0253(11) Uani 1 1 d . . .
H8A H 0.1560 0.5789 0.1540 0.038 Uiso 1 1 calc R . .
H8B H 0.3197 0.4749 0.1215 0.038 Uiso 1 1 calc R . .
H8C H 0.3671 0.6580 0.0709 0.038 Uiso 1 1 calc R . .
C2 C 0.2393(6) 0.5526(6) 0.5714(6) 0.0167(9) Uani 1 1 d . . .
C3 C 0.2533(6) 0.6019(6) 0.4021(6) 0.0157(9) Uani 1 1 d . . .
C9 C 0.2481(8) 0.0939(6) 0.7448(7) 0.0252(11) Uani 1 1 d . . .
H9A H 0.2975 0.0816 0.8286 0.038 Uiso 1 1 calc R . .
H9B H 0.3249 0.0472 0.6741 0.038 Uiso 1 1 calc R . .
H9C H 0.1205 0.0371 0.8097 0.038 Uiso 1 1 calc R . .
C7 C 0.2272(8) 0.6720(7) 0.6321(7) 0.0245(11) Uani 1 1 d . . .
H7A H 0.3475 0.7410 0.5697 0.037 Uiso 1 1 calc R . .
H7B H 0.1935 0.6129 0.7595 0.037 Uiso 1 1 calc R . .
H7C H 0.1326 0.7402 0.6065 0.037 Uiso 1 1 calc R . .
C4 C 0.2659(6) 0.4957(6) 0.3386(6) 0.0177(10) Uani 1 1 d . . .
C1 C 0.2358(6) 0.3859(6) 0.6785(6) 0.0170(10) Uani 1 1 d . . .
C5 C 0.2652(6) 0.3331(6) 0.4530(6) 0.0165(9) Uani 1 1 d . . .

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
I2 0.03202(18) 0.01129(17) 0.01764(17) -0.00437(14) -0.01050(13) 0.00237(13)
I1 0.03500(18) 0.02064(19) 0.01435(16) -0.00878(15) -0.01279(13) 0.00625(14)
I3 0.0425(2) 0.01817(19) 0.02429(19) -0.01495(16) -0.01758(15) 0.00774(15)
C6 0.020(2) 0.011(2) 0.014(2) -0.0048(19) -0.0084(18) 0.0025(18)
C8 0.036(3) 0.026(3) 0.019(3) -0.013(2) -0.014(2) 0.005(2)
C2 0.019(2) 0.014(3) 0.018(2) -0.010(2) -0.0073(18) 0.0034(18)
C3 0.018(2) 0.011(2) 0.016(2) -0.006(2) -0.0057(18) 0.0013(17)
C9 0.043(3) 0.009(3) 0.019(3) -0.003(2) -0.015(2) 0.005(2)
C7 0.044(3) 0.013(3) 0.021(3) -0.011(2) -0.016(2) 0.005(2)
C4 0.020(2) 0.017(3) 0.014(2) -0.007(2) -0.0054(18) -0.0007(19)
C1 0.019(2) 0.019(3) 0.011(2) -0.007(2) -0.0052(18) 0.0019(19)
C5 0.020(2) 0.015(3) 0.018(2) -0.011(2) -0.0068(18) 0.0016(18)

_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
I2 C3 2.123(5) . ?
I1 C1 2.125(4) . ?
I3 C5 2.127(4) . ?
C6 C9 1.504(7) . ?
C6 C1 1.400(7) . ?
C6 C5 1.402(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C4 1.513(7) . ?
C2 C3 1.403(6) . ?
C2 C7 1.500(7) . ?
C2 C1 1.399(7) . ?
C3 C4 1.401(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 C5 1.387(7) . ?

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
C1 C6 C9 122.2(4) . . ?
C1 C6 C5 115.8(4) . . ?
C5 C6 C9 122.0(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C3 C2 C7 121.6(4) . . ?
C1 C2 C3 115.5(4) . . ?
C1 C2 C7 122.9(4) . . ?
C2 C3 I2 118.2(3) . . ?
C4 C3 I2 117.8(3) . . ?
C4 C3 C2 124.0(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C8 121.0(5) . . ?
C5 C4 C8 122.6(4) . . ?
C5 C4 C3 116.4(4) . . ?
C6 C1 I1 118.0(4) . . ?
C2 C1 I1 117.6(3) . . ?
C2 C1 C6 124.3(4) . . ?
C6 C5 I3 117.4(3) . . ?
C4 C5 I3 118.6(3) . . ?
C4 C5 C6 124.0(4) . . ?
####################################################################### 
# 
# 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_tim-190K
_database_code_depnum_ccdc_archive 'CCDC 1058006'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-09-29
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
triiodomesitylene   
;
_chemical_formula_moiety         'C9 H9 I3'
_chemical_formula_sum            'C9 H9 I3'
_chemical_formula_weight         497.86
_chemical_melting_point          ?

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.9700(5)
_cell_length_b                   9.5781(6)
_cell_length_c                   9.5874(6)
_cell_angle_alpha                60.223(6)
_cell_angle_beta                 66.693(6)
_cell_angle_gamma                85.452(5)
_cell_volume                     577.07(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      29.0990
_cell_measurement_theta_min      4.4385
_exptl_absorpt_coefficient_mu    8.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.865
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5479
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         4.45
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9932
_diffrn_measured_fraction_theta_max 0.9356
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   22.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
  2 omega  -65.00  -38.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00   16.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   99.0000   35.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   37.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega  -48.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366  -37.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
  7 omega  -94.00  -32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  178.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   37.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000   60.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0535762000
_diffrn_orient_matrix_UB_12      0.0780175000
_diffrn_orient_matrix_UB_13      -0.0624398000
_diffrn_orient_matrix_UB_21      0.0402145000
_diffrn_orient_matrix_UB_22      -0.0248951000
_diffrn_orient_matrix_UB_23      -0.0630835000
_diffrn_orient_matrix_UB_31      -0.0714845000
_diffrn_orient_matrix_UB_32      0.0270879000
_diffrn_orient_matrix_UB_33      -0.0295033000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2339
_reflns_number_total             2653
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.783
_refine_diff_density_min         -1.274
_refine_diff_density_rms         0.184
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0294P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0698
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H8A,H8B,H8C} of C8, {H9A,H9B,H9C} of C9, {H7A,H7B,H7C} of C7
2.a Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
I2 I 0.26006(5) 0.85273(4) 0.22991(4) 0.02792(10) Uani 1 1 d . . .
I1 I 0.20463(5) 0.30141(4) 0.93963(4) 0.02914(11) Uani 1 1 d . . .
I3 I 0.28425(5) 0.16488(4) 0.36631(5) 0.03228(11) Uani 1 1 d . . .
C6 C 0.2503(6) 0.2720(6) 0.6249(6) 0.0213(10) Uani 1 1 d . . .
C8 C 0.2775(8) 0.5569(7) 0.1563(7) 0.0281(11) Uani 1 1 d . . .
H8A H 0.1647 0.6013 0.1474 0.042 Uiso 1 1 calc R . .
H8B H 0.2911 0.4662 0.1343 0.042 Uiso 1 1 calc R . .
H8C H 0.3846 0.6420 0.0686 0.042 Uiso 1 1 calc R . .
C2 C 0.2390(6) 0.5520(6) 0.5715(6) 0.0220(10) Uani 1 1 d . . .
C3 C 0.2531(6) 0.6018(6) 0.4025(6) 0.0196(10) Uani 1 1 d . . .
C9 C 0.2480(8) 0.0949(6) 0.7455(7) 0.0301(12) Uani 1 1 d . . .
H9A H 0.3346 0.0834 0.7987 0.045 Uiso 1 1 calc R . .
H9B H 0.2846 0.0392 0.6779 0.045 Uiso 1 1 calc R . .
H9C H 0.1232 0.0467 0.8386 0.045 Uiso 1 1 calc R . .
C7 C 0.2270(8) 0.6710(7) 0.6327(8) 0.0331(12) Uani 1 1 d . . .
H7A H 0.3514 0.7108 0.6068 0.050 Uiso 1 1 calc R . .
H7B H 0.1519 0.6170 0.7601 0.050 Uiso 1 1 calc R . .
H7C H 0.1700 0.7627 0.5713 0.050 Uiso 1 1 calc R . .
C4 C 0.2655(6) 0.4975(6) 0.3382(6) 0.0211(10) Uani 1 1 d . . .
C1 C 0.2368(6) 0.3863(6) 0.6779(6) 0.0198(10) Uani 1 1 d . . .
C5 C 0.2646(6) 0.3328(6) 0.4534(6) 0.0204(10) Uani 1 1 d . . .

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
I2 0.0412(2) 0.01460(17) 0.02278(19) -0.00533(14) -0.01385(15) 0.00337(14)
I1 0.0448(2) 0.0264(2) 0.01842(18) -0.01076(15) -0.01639(15) 0.00826(16)
I3 0.0545(2) 0.02325(19) 0.0307(2) -0.01837(16) -0.02274(17) 0.01049(17)
C6 0.026(2) 0.016(2) 0.022(3) -0.008(2) -0.011(2) 0.005(2)
C8 0.043(3) 0.024(3) 0.019(3) -0.011(2) -0.015(2) 0.008(2)
C2 0.024(2) 0.018(2) 0.023(3) -0.011(2) -0.008(2) 0.003(2)
C3 0.024(2) 0.014(2) 0.016(2) -0.0046(19) -0.0075(18) 0.0021(19)
C9 0.046(3) 0.014(2) 0.031(3) -0.009(2) -0.019(3) 0.003(2)
C7 0.051(3) 0.026(3) 0.029(3) -0.018(3) -0.018(3) 0.010(3)
C4 0.022(2) 0.023(3) 0.016(2) -0.008(2) -0.0078(19) 0.001(2)
C1 0.024(2) 0.021(2) 0.012(2) -0.007(2) -0.0073(19) 0.001(2)
C5 0.025(2) 0.018(2) 0.023(3) -0.013(2) -0.010(2) 0.002(2)

_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
I2 C3 2.125(5) . ?
I1 C1 2.126(4) . ?
I3 C5 2.122(5) . ?
C6 C9 1.501(7) . ?
C6 C1 1.400(7) . ?
C6 C5 1.402(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C4 1.506(7) . ?
C2 C3 1.400(6) . ?
C2 C7 1.502(7) . ?
C2 C1 1.394(7) . ?
C3 C4 1.391(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 C5 1.405(7) . ?

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
C1 C6 C9 121.8(4) . . ?
C1 C6 C5 115.9(4) . . ?
C5 C6 C9 122.3(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C3 C2 C7 121.6(4) . . ?
C1 C2 C3 115.9(4) . . ?
C1 C2 C7 122.5(4) . . ?
C2 C3 I2 118.6(3) . . ?
C4 C3 I2 117.3(3) . . ?
C4 C3 C2 124.2(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C8 122.1(4) . . ?
C3 C4 C5 116.2(4) . . ?
C5 C4 C8 121.7(4) . . ?
C6 C1 I1 118.0(3) . . ?
C2 C1 I1 117.7(3) . . ?
C2 C1 C6 124.3(4) . . ?
C6 C5 I3 117.6(3) . . ?
C6 C5 C4 123.6(4) . . ?
C4 C5 I3 118.8(3) . . ?
####################################################################### 
# 
# 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_tim-226K
_database_code_depnum_ccdc_archive 'CCDC 1058007'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-08-18
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
triiodomesitylene   
;
_chemical_formula_moiety         'C9 H9 I3'
_chemical_formula_sum            'C9 H9 I3'
_chemical_formula_weight         497.86
_chemical_melting_point          ?

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.9901(4)
_cell_length_b                   9.5851(6)
_cell_length_c                   9.5953(6)
_cell_angle_alpha                60.221(6)
_cell_angle_beta                 66.709(6)
_cell_angle_gamma                85.445(5)
_cell_volume                     579.51(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2339
_cell_measurement_temperature    226(2)
_cell_measurement_theta_max      29.2025
_cell_measurement_theta_min      4.4341
_exptl_absorpt_coefficient_mu    8.041
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.853
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5466
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.27
_diffrn_reflns_theta_min         4.44
_diffrn_ambient_temperature      226(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9928
_diffrn_measured_fraction_theta_max 0.9359
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   22.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
  2 omega  -65.00  -38.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00   16.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   99.0000   35.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   37.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega  -48.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366  -37.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
  7 omega  -94.00  -32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  178.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   35.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000   60.0000 37
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0534387000
_diffrn_orient_matrix_UB_12      0.0779425000
_diffrn_orient_matrix_UB_13      -0.0623875000
_diffrn_orient_matrix_UB_21      0.0401184000
_diffrn_orient_matrix_UB_22      -0.0249187000
_diffrn_orient_matrix_UB_23      -0.0629878000
_diffrn_orient_matrix_UB_31      -0.0712818000
_diffrn_orient_matrix_UB_32      0.0270746000
_diffrn_orient_matrix_UB_33      -0.0295271000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2336
_reflns_number_total             2665
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.863
_refine_diff_density_min         -1.241
_refine_diff_density_rms         0.184
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0374P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0788
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H8A,H8B,H8C} of C8, {H7A,H7B,H7C} of C7, {H9A,H9B,H9C} of C9
2.a Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
I2 I 0.26021(5) 0.85240(4) 0.23017(5) 0.03225(12) Uani 1 1 d . . .
I1 I 0.20446(5) 0.30178(5) 0.93936(5) 0.03354(12) Uani 1 1 d . . .
I3 I 0.28429(6) 0.16529(5) 0.36654(5) 0.03722(12) Uani 1 1 d . . .
C6 C 0.2503(6) 0.2724(6) 0.6251(7) 0.0233(10) Uani 1 1 d . . .
C8 C 0.2778(8) 0.5576(7) 0.1567(7) 0.0326(12) Uani 1 1 d . . .
H8A H 0.1817 0.6237 0.1383 0.049 Uiso 1 1 calc R . .
H8B H 0.2626 0.4654 0.1444 0.049 Uiso 1 1 calc R . .
H8C H 0.3973 0.6222 0.0700 0.049 Uiso 1 1 calc R . .
C2 C 0.2395(6) 0.5528(6) 0.5717(7) 0.0243(10) Uani 1 1 d . . .
C3 C 0.2539(6) 0.6017(6) 0.4026(6) 0.0214(10) Uani 1 1 d . . .
C9 C 0.2483(9) 0.0946(7) 0.7459(8) 0.0353(13) Uani 1 1 d . . .
H9A H 0.3349 0.0832 0.7975 0.053 Uiso 1 1 calc R . .
H9B H 0.2833 0.0394 0.6791 0.053 Uiso 1 1 calc R . .
H9C H 0.1255 0.0469 0.8388 0.053 Uiso 1 1 calc R . .
C7 C 0.2278(9) 0.6719(7) 0.6320(8) 0.0366(13) Uani 1 1 d . . .
H7A H 0.3494 0.7307 0.5815 0.055 Uiso 1 1 calc R . .
H7B H 0.1804 0.6142 0.7595 0.055 Uiso 1 1 calc R . .
H7C H 0.1459 0.7480 0.5940 0.055 Uiso 1 1 calc R . .
C4 C 0.2651(6) 0.4979(6) 0.3385(7) 0.0238(10) Uani 1 1 d . . .
C1 C 0.2367(6) 0.3870(6) 0.6779(6) 0.0215(10) Uani 1 1 d . . .
C5 C 0.2647(6) 0.3327(6) 0.4540(7) 0.0240(10) Uani 1 1 d . . .

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
I2 0.0467(2) 0.01713(18) 0.0266(2) -0.00634(15) -0.01558(16) 0.00395(15)
I1 0.0506(2) 0.0309(2) 0.02137(19) -0.01265(16) -0.01833(16) 0.00923(17)
I3 0.0619(3) 0.0269(2) 0.0361(2) -0.02150(18) -0.02593(19) 0.01189(18)
C6 0.029(2) 0.018(2) 0.023(3) -0.009(2) -0.013(2) 0.004(2)
C8 0.047(3) 0.030(3) 0.021(3) -0.012(2) -0.015(2) 0.005(3)
C2 0.025(2) 0.021(3) 0.025(3) -0.012(2) -0.009(2) 0.004(2)
C3 0.026(2) 0.017(2) 0.015(2) -0.0048(19) -0.0058(18) 0.0000(19)
C9 0.059(3) 0.018(3) 0.029(3) -0.009(2) -0.022(3) 0.007(3)
C7 0.060(4) 0.025(3) 0.033(3) -0.020(3) -0.021(3) 0.014(3)
C4 0.024(2) 0.023(3) 0.020(3) -0.009(2) -0.0076(19) 0.002(2)
C1 0.028(2) 0.020(2) 0.013(2) -0.007(2) -0.0072(19) 0.003(2)
C5 0.030(2) 0.019(2) 0.025(3) -0.013(2) -0.011(2) 0.003(2)

_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
I2 C3 2.125(5) . ?
I1 C1 2.124(5) . ?
I3 C5 2.120(5) . ?
C6 C9 1.509(7) . ?
C6 C1 1.401(7) . ?
C6 C5 1.401(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C8 C4 1.503(7) . ?
C2 C3 1.404(7) . ?
C2 C7 1.498(7) . ?
C2 C1 1.394(7) . ?
C3 C4 1.389(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C4 C5 1.411(7) . ?

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
C1 C6 C9 121.9(4) . . ?
C5 C6 C9 122.0(5) . . ?
C5 C6 C1 116.1(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C3 C2 C7 121.7(5) . . ?
C1 C2 C3 115.4(4) . . ?
C1 C2 C7 122.9(5) . . ?
C2 C3 I2 118.3(3) . . ?
C4 C3 I2 117.1(3) . . ?
C4 C3 C2 124.7(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C8 122.2(5) . . ?
C3 C4 C5 116.0(4) . . ?
C5 C4 C8 121.8(5) . . ?
C6 C1 I1 117.8(3) . . ?
C2 C1 I1 117.7(4) . . ?
C2 C1 C6 124.5(4) . . ?
C6 C5 I3 117.9(4) . . ?
C6 C5 C4 123.4(5) . . ?
C4 C5 I3 118.7(4) . . ?
####################################################################### 
# 
# 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_tim-262K
_database_code_depnum_ccdc_archive 'CCDC 1058008'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_audit_creation_date             2013-08-18
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
triiodomesitylene   
;
_chemical_formula_moiety         'C9 H9 I3'
_chemical_formula_sum            'C9 H9 I3'
_chemical_formula_weight         497.86
_chemical_melting_point          ?

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.0247(5)
_cell_length_b                   9.6025(5)
_cell_length_c                   9.6148(5)
_cell_angle_alpha                60.183(6)
_cell_angle_beta                 66.729(6)
_cell_angle_gamma                85.377(5)
_cell_volume                     584.24(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2271
_cell_measurement_temperature    262(2)
_cell_measurement_theta_max      28.9904
_cell_measurement_theta_min      4.2929
_exptl_absorpt_coefficient_mu    7.976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.830
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5409
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.05
_diffrn_reflns_theta_min         4.30
_diffrn_ambient_temperature      262(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9932
_diffrn_measured_fraction_theta_max 0.9364
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -88.00    5.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -77.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00   22.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -77.00  -32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  178.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega   42.00   88.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366  178.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00   40.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.1366  -57.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
  7 omega  -88.00   13.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -77.0000    0.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0531388000
_diffrn_orient_matrix_UB_12      0.0777952000
_diffrn_orient_matrix_UB_13      -0.0621976000
_diffrn_orient_matrix_UB_21      0.0400881000
_diffrn_orient_matrix_UB_22      -0.0248798000
_diffrn_orient_matrix_UB_23      -0.0628331000
_diffrn_orient_matrix_UB_31      -0.0708999000
_diffrn_orient_matrix_UB_32      0.0270844000
_diffrn_orient_matrix_UB_33      -0.0296384000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2237
_reflns_number_total             2649
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.707
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0288P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0681
_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. 

1. Fixed Uiso
 At 1.5 times of:
  {H9A,H9B,H9C} of C9, {H7A,H7B,H7C} of C7, {H8A,H8B,H8C} of C8
2.a Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
I2 I 0.26062(5) 0.85219(4) 0.23039(4) 0.03802(11) Uani 1 1 d . . .
I1 I 0.20407(5) 0.30216(4) 0.93897(4) 0.03966(11) Uani 1 1 d . . .
I3 I 0.28442(5) 0.16573(4) 0.36684(5) 0.04393(12) Uani 1 1 d . . .
C6 C 0.2493(6) 0.2735(5) 0.6250(6) 0.0264(10) Uani 1 1 d . . .
C8 C 0.2777(7) 0.5569(6) 0.1572(7) 0.0373(12) Uani 1 1 d . . .
H8A H 0.1880 0.6278 0.1363 0.056 Uiso 1 1 calc R . .
H8B H 0.2552 0.4662 0.1472 0.056 Uiso 1 1 calc R . .
H8C H 0.3980 0.6149 0.0721 0.056 Uiso 1 1 calc R . .
C2 C 0.2391(6) 0.5531(5) 0.5710(6) 0.0254(9) Uani 1 1 d . . .
C3 C 0.2535(6) 0.6023(5) 0.4018(6) 0.0246(9) Uani 1 1 d . . .
C9 C 0.2484(8) 0.0975(6) 0.7446(7) 0.0416(13) Uani 1 1 d . . .
H9A H 0.3402 0.0863 0.7887 0.062 Uiso 1 1 calc R . .
H9B H 0.2745 0.0414 0.6807 0.062 Uiso 1 1 calc R . .
H9C H 0.1301 0.0519 0.8412 0.062 Uiso 1 1 calc R . .
C7 C 0.2267(7) 0.6714(6) 0.6332(7) 0.0394(12) Uani 1 1 d . . .
H7A H 0.2843 0.7774 0.5339 0.059 Uiso 1 1 calc R . .
H7B H 0.2876 0.6373 0.7108 0.059 Uiso 1 1 calc R . .
H7C H 0.1002 0.6751 0.6947 0.059 Uiso 1 1 calc R . .
C4 C 0.2648(6) 0.4970(5) 0.3386(6) 0.0270(10) Uani 1 1 d . . .
C1 C 0.2353(6) 0.3863(6) 0.6780(6) 0.0269(10) Uani 1 1 d . . .
C5 C 0.2635(6) 0.3339(5) 0.4539(6) 0.0272(10) Uani 1 1 d . . .

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
I2 0.0555(2) 0.01992(17) 0.03105(18) -0.00685(13) -0.01887(15) 0.00483(13)
I1 0.0604(2) 0.0362(2) 0.02481(17) -0.01443(14) -0.02201(16) 0.01126(15)
I3 0.0738(3) 0.0313(2) 0.0423(2) -0.02486(17) -0.03096(19) 0.01406(16)
C6 0.034(3) 0.019(2) 0.026(2) -0.0090(18) -0.015(2) 0.0054(17)
C8 0.053(3) 0.029(3) 0.031(3) -0.015(2) -0.018(2) 0.009(2)
C2 0.031(2) 0.020(2) 0.022(2) -0.0108(18) -0.0072(18) 0.0033(17)
C3 0.031(2) 0.013(2) 0.026(2) -0.0079(17) -0.0116(19) 0.0034(16)
C9 0.065(4) 0.022(3) 0.040(3) -0.012(2) -0.029(3) 0.010(2)
C7 0.062(3) 0.030(3) 0.032(3) -0.019(2) -0.022(3) 0.011(2)
C4 0.028(2) 0.021(2) 0.024(2) -0.0072(18) -0.0103(19) 0.0018(17)
C1 0.032(2) 0.030(3) 0.019(2) -0.0103(19) -0.0130(19) 0.0045(18)
C5 0.033(2) 0.022(2) 0.028(2) -0.0128(19) -0.012(2) 0.0002(18)

_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
I2 C3 2.120(4) . ?
I1 C1 2.128(4) . ?
I3 C5 2.128(4) . ?
C6 C9 1.497(6) . ?
C6 C1 1.389(6) . ?
C6 C5 1.403(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C4 1.501(7) . ?
C2 C3 1.406(6) . ?
C2 C7 1.507(6) . ?
C2 C1 1.404(6) . ?
C3 C4 1.397(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C4 C5 1.396(6) . ?

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
C1 C6 C9 121.6(4) . . ?
C1 C6 C5 116.2(4) . . ?
C5 C6 C9 122.2(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
C3 C2 C7 122.2(4) . . ?
C1 C2 C3 115.4(4) . . ?
C1 C2 C7 122.4(4) . . ?
C2 C3 I2 118.1(3) . . ?
C4 C3 I2 117.7(3) . . ?
C4 C3 C2 124.2(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C8 121.6(4) . . ?
C5 C4 C8 122.3(4) . . ?
C5 C4 C3 116.0(4) . . ?
C6 C1 I1 118.3(3) . . ?
C6 C1 C2 124.3(4) . . ?
C2 C1 I1 117.4(3) . . ?
C6 C5 I3 117.6(3) . . ?
C4 C5 I3 118.5(3) . . ?
C4 C5 C6 123.8(4) . . ?

