# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_delta

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22'
_chemical_formula_weight         358.45

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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.835(7)
_cell_length_b                   10.222(7)
_cell_length_c                   16.06(1)
_cell_angle_alpha                83.79(1)
_cell_angle_beta                 76.41(1)
_cell_angle_gamma                87.92(1)
_cell_volume                     1560.1(18)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4095
_cell_measurement_theta_min      5
_cell_measurement_theta_max      23

_exptl_crystal_description       'irregular prism'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             570
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.065

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS procedure'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  diffractometer
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 8.2
_diffrn_reflns_number            14226
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.311
_diffrn_reflns_theta_max         23.421
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.800
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.800
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.800
_reflns_number_total             4516
_reflns_number_gt                3290
_reflns_threshold_expression     'I > 2σ(I)'


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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR2004 (Altomare et al. 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1140P)²+0.1021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4516
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1822
_refine_ls_wR_factor_gt          0.1615
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1893(2) 0.7896(2) 0.17884(15) 0.0490(6) Uani 1 1 d . . . . .
C2 C 0.2288(2) 0.8518(2) 0.09507(16) 0.0571(6) Uani 1 1 d . . . . .
H2 H 0.1983 0.8191 0.0509 0.069 Uiso 1 1 calc R U . . .
C3 C 0.3128(3) 0.9614(2) 0.0774(2) 0.0706(8) Uani 1 1 d . . . . .
H3 H 0.3384 1.0017 0.0213 0.085 Uiso 1 1 calc R U . . .
C4 C 0.3587(3) 1.0115(3) 0.1411(2) 0.0798(9) Uani 1 1 d . . . . .
H4 H 0.4136 1.0864 0.1287 0.096 Uiso 1 1 calc R U . . .
C5 C 0.3234(3) 0.9505(3) 0.2239(2) 0.0868(9) Uani 1 1 d . . . . .
H5 H 0.3569 0.9824 0.2673 0.104 Uiso 1 1 calc R U . . .
C6 C 0.2382(3) 0.8417(3) 0.24227(18) 0.0722(8) Uani 1 1 d . . . . .
H6 H 0.2131 0.8024 0.2986 0.087 Uiso 1 1 calc R U . . .
C7 C 0.1008(2) 0.6714(2) 0.19965(14) 0.0482(6) Uani 1 1 d . . . . .
C8 C -0.0071(2) 0.6630(2) 0.28266(14) 0.0504(6) Uani 1 1 d . . . . .
C9 C -0.0987(3) 0.7675(3) 0.30301(17) 0.0697(7) Uani 1 1 d . . . . .
H9 H -0.0904 0.8437 0.2650 0.084 Uiso 1 1 calc R U . . .
C10 C -0.2010(3) 0.7611(3) 0.3776(2) 0.0880(9) Uani 1 1 d . . . . .
H10 H -0.2631 0.8312 0.3892 0.106 Uiso 1 1 calc R U . . .
C11 C -0.2115(3) 0.6502(4) 0.4356(2) 0.0913(10) Uani 1 1 d . . . . .
H11 H -0.2804 0.6455 0.4866 0.110 Uiso 1 1 calc R U . . .
C12 C -0.1211(3) 0.5475(3) 0.41819(18) 0.0830(9) Uani 1 1 d . . . . .
H12 H -0.1281 0.4731 0.4577 0.100 Uiso 1 1 calc R U . . .
C13 C -0.0191(3) 0.5526(2) 0.34241(16) 0.0652(7) Uani 1 1 d . . . . .
H13 H 0.0419 0.4816 0.3313 0.078 Uiso 1 1 calc R U . . .
C14 C 0.1175(2) 0.5774(2) 0.14443(15) 0.0515(6) Uani 1 1 d . . . . .
H14 H 0.1933 0.5864 0.0971 0.062 Uiso 1 1 calc R U . . .
C15 C 0.0295(2) 0.4651(2) 0.15177(15) 0.0534(6) Uani 1 1 d . . . . .
H15 H -0.0503 0.4605 0.1965 0.064 Uiso 1 1 calc R U . . .
C16 C 0.0501(2) 0.3653(2) 0.10078(14) 0.0478(6) Uani 1 1 d . . . . .
C17 C 0.1803(2) 0.34624(19) 0.03453(14) 0.0468(6) Uani 1 1 d . . . . .
C18 C 0.3116(2) 0.3566(2) 0.05048(16) 0.0575(6) Uani 1 1 d . . . . .
H18 H 0.3193 0.3770 0.1042 0.069 Uiso 1 1 calc R U . . .
C19 C 0.4307(3) 0.3372(2) -0.01177(19) 0.0678(7) Uani 1 1 d . . . . .
H19 H 0.5177 0.3452 0.0004 0.081 Uiso 1 1 calc R U . . .
C20 C 0.4233(3) 0.3059(3) -0.09192(19) 0.0717(8) Uani 1 1 d . . . . .
H20 H 0.5046 0.2924 -0.1335 0.086 Uiso 1 1 calc R U . . .
C21 C 0.2941(3) 0.2948(2) -0.10958(17) 0.0680(7) Uani 1 1 d . . . . .
H21 H 0.2876 0.2745 -0.1636 0.082 Uiso 1 1 calc R U . . .
C22 C 0.1743(3) 0.3139(2) -0.04717(15) 0.0548(6) Uani 1 1 d . . . . .
H22 H 0.0876 0.3050 -0.0595 0.066 Uiso 1 1 calc R U . . .
C23 C -0.0629(2) 0.2680(2) 0.11129(14) 0.0482(6) Uani 1 1 d . . . . .
C24 C -0.2032(2) 0.3048(2) 0.13106(15) 0.0566(6) Uani 1 1 d . . . . .
H24 H -0.2276 0.3930 0.1350 0.068 Uiso 1 1 calc R U . . .
C25 C -0.3068(3) 0.2121(3) 0.14497(16) 0.0651(7) Uani 1 1 d . . . . .
H25 H -0.4003 0.2383 0.1583 0.078 Uiso 1 1 calc R U . . .
C26 C -0.2722(3) 0.0803(3) 0.13913(17) 0.0669(7) Uani 1 1 d . . . . .
H26 H -0.3423 0.0178 0.1496 0.080 Uiso 1 1 calc R U . . .
C27 C -0.1348(3) 0.0425(2) 0.11787(16) 0.0629(7) Uani 1 1 d . . . . .
H27 H -0.1115 -0.0458 0.1127 0.075 Uiso 1 1 calc R U . . .
C28 C -0.0302(3) 0.1343(2) 0.10399(15) 0.0549(6) Uani 1 1 d . . . . .
H28 H 0.0629 0.1073 0.0897 0.066 Uiso 1 1 calc R U . . .
C29 C -0.2844(2) 0.1575(2) 0.43029(14) 0.0505(6) Uani 1 1 d . . . . .
C30 C -0.1825(3) 0.1501(3) 0.35510(16) 0.0659(7) Uani 1 1 d . . . . .
H30 H -0.2087 0.1421 0.3039 0.079 Uiso 1 1 calc R U . . .
C31 C -0.0424(3) 0.1544(3) 0.3551(2) 0.0815(9) Uani 1 1 d . . . . .
H31 H 0.0249 0.1489 0.3040 0.098 Uiso 1 1 calc R U . . .
C32 C -0.0020(3) 0.1668(3) 0.4297(2) 0.0814(9) Uani 1 1 d . . . . .
H32 H 0.0925 0.1697 0.4295 0.098 Uiso 1 1 calc R U . . .
C33 C -0.1009(3) 0.1747(3) 0.50442(19) 0.0824(9) Uani 1 1 d . . . . .
H33 H -0.0735 0.1836 0.5551 0.099 Uiso 1 1 calc R U . . .
C34 C -0.2409(3) 0.1698(3) 0.50538(17) 0.0690(7) Uani 1 1 d . . . . .
H34 H -0.3072 0.1747 0.5569 0.083 Uiso 1 1 calc R U . . .
C35 C -0.4350(2) 0.1542(2) 0.42979(14) 0.0497(6) Uani 1 1 d . . . . .
C36 C -0.4909(2) 0.2635(2) 0.37834(15) 0.0534(6) Uani 1 1 d . . . . .
C37 C -0.4340(3) 0.3882(3) 0.3663(2) 0.0790(9) Uani 1 1 d . . . . .
H37 H -0.3573 0.4029 0.3885 0.095 Uiso 1 1 calc R U . . .
C38 C -0.4915(4) 0.4917(3) 0.3210(3) 0.1059(12) Uani 1 1 d . . . . .
H38 H -0.4526 0.5750 0.3133 0.127 Uiso 1 1 calc R U . . .
C39 C -0.6030(3) 0.4725(3) 0.2882(2) 0.0996(11) Uani 1 1 d . . . . .
H39 H -0.6413 0.5425 0.2590 0.120 Uiso 1 1 calc R U . . .
C40 C -0.6593(3) 0.3503(3) 0.29794(18) 0.0777(8) Uani 1 1 d . . . . .
H40 H -0.7350 0.3366 0.2746 0.093 Uiso 1 1 calc R U . . .
C41 C -0.6037(3) 0.2470(3) 0.34245(15) 0.0612(7) Uani 1 1 d . . . . .
H41 H -0.6429 0.1640 0.3486 0.073 Uiso 1 1 calc R U . . .
C42 C -0.5206(2) 0.0567(2) 0.47510(15) 0.0536(6) Uani 1 1 d . . . . .
H42 H -0.6146 0.0641 0.4737 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.385(3) . ?
C1 C2 1.397(3) . ?
C1 C7 1.478(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.364(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.381(4) . ?
C7 C14 1.357(3) . ?
C7 C8 1.492(3) . ?
C8 C9 1.388(3) . ?
C8 C13 1.389(3) . ?
C9 C10 1.369(4) . ?
C10 C11 1.377(5) . ?
C11 C12 1.360(4) . ?
C12 C13 1.381(4) . ?
C14 C15 1.441(3) . ?
C15 C16 1.356(3) . ?
C16 C17 1.482(3) . ?
C16 C23 1.486(3) . ?
C17 C18 1.384(3) . ?
C17 C22 1.402(3) . ?
C18 C19 1.373(4) . ?
C19 C20 1.378(4) . ?
C20 C21 1.377(4) . ?
C21 C22 1.378(3) . ?
C23 C24 1.389(3) . ?
C23 C28 1.404(3) . ?
C24 C25 1.379(3) . ?
C25 C26 1.385(4) . ?
C26 C27 1.366(4) . ?
C27 C28 1.381(3) . ?
C29 C30 1.383(3) . ?
C29 C34 1.390(3) . ?
C29 C35 1.485(3) . ?
C30 C31 1.380(4) . ?
C31 C32 1.368(4) . ?
C32 C33 1.363(4) . ?
C33 C34 1.376(4) . ?
C35 C42 1.359(3) . ?
C35 C36 1.484(3) . ?
C36 C37 1.387(3) . ?
C36 C41 1.388(3) . ?
C37 C38 1.397(4) . ?
C38 C39 1.353(5) . ?
C39 C40 1.363(4) . ?
C40 C41 1.380(4) . ?
C42 C42 1.437(4) 2_456 ?

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 C1 C2 117.5(2) . . ?
C6 C1 C7 120.7(2) . . ?
C2 C1 C7 121.8(2) . . ?
C3 C2 C1 120.6(2) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 119.7(3) . . ?
C4 C5 C6 119.8(3) . . ?
C5 C6 C1 121.6(3) . . ?
C14 C7 C1 120.6(2) . . ?
C14 C7 C8 122.8(2) . . ?
C1 C7 C8 116.62(18) . . ?
C9 C8 C13 117.6(2) . . ?
C9 C8 C7 120.4(2) . . ?
C13 C8 C7 122.0(2) . . ?
C10 C9 C8 121.6(3) . . ?
C9 C10 C11 119.6(3) . . ?
C12 C11 C10 120.0(3) . . ?
C11 C12 C13 120.7(3) . . ?
C12 C13 C8 120.5(3) . . ?
C7 C14 C15 126.5(2) . . ?
C16 C15 C14 127.3(2) . . ?
C15 C16 C17 123.8(2) . . ?
C15 C16 C23 119.0(2) . . ?
C17 C16 C23 117.21(19) . . ?
C18 C17 C22 117.2(2) . . ?
C18 C17 C16 122.2(2) . . ?
C22 C17 C16 120.6(2) . . ?
C19 C18 C17 121.1(2) . . ?
C18 C19 C20 121.1(3) . . ?
C21 C20 C19 119.1(2) . . ?
C20 C21 C22 119.9(3) . . ?
C21 C22 C17 121.6(2) . . ?
C24 C23 C28 117.9(2) . . ?
C24 C23 C16 121.6(2) . . ?
C28 C23 C16 120.5(2) . . ?
C25 C24 C23 120.9(2) . . ?
C24 C25 C26 120.3(2) . . ?
C27 C26 C25 119.7(2) . . ?
C26 C27 C28 120.5(2) . . ?
C27 C28 C23 120.8(2) . . ?
C30 C29 C34 117.8(2) . . ?
C30 C29 C35 120.6(2) . . ?
C34 C29 C35 121.6(2) . . ?
C31 C30 C29 120.9(2) . . ?
C32 C31 C30 120.3(3) . . ?
C33 C32 C31 119.7(3) . . ?
C32 C33 C34 120.5(3) . . ?
C33 C34 C29 120.8(3) . . ?
C42 C35 C36 120.4(2) . . ?
C42 C35 C29 122.2(2) . . ?
C36 C35 C29 117.41(18) . . ?
C37 C36 C41 117.2(2) . . ?
C37 C36 C35 120.7(2) . . ?
C41 C36 C35 122.0(2) . . ?
C36 C37 C38 120.2(3) . . ?
C39 C38 C37 120.9(3) . . ?
C38 C39 C40 119.9(3) . . ?
C39 C40 C41 119.9(3) . . ?
C40 C41 C36 121.8(2) . . ?
C35 C42 C42 126.1(3) . 2_456 ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 990581'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tpb-c-hex

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H34'
_chemical_formula_weight         442.61

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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.846(3)
_cell_length_b                   8.839(3)
_cell_length_c                   10.016(3)
_cell_angle_alpha                74.927(6)
_cell_angle_beta                 64.092(5)
_cell_angle_gamma                68.128(6)
_cell_volume                     649.3(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3900
_cell_measurement_theta_min      5
_cell_measurement_theta_max      20

_exptl_crystal_description       'irregular prism'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_F_000             238
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.7
_exptl_absorpt_coefficient_mu    0.063

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS procedure'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  diffractometer
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 8.2
_diffrn_reflns_number            5164
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         26.341
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             2622
_reflns_number_gt                1350
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000


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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR2004 (Altomare et al. 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1293P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2622
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.2321
_refine_ls_wR_factor_gt          0.1950
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6722(3) -0.0755(3) 0.6799(3) 0.0471(7) Uani 1 1 d . . . . .
C2 C 0.8338(4) -0.1666(4) 0.5873(3) 0.0612(9) Uani 1 1 d . . . . .
C3 C 0.9334(4) -0.3071(4) 0.6450(4) 0.0732(10) Uani 1 1 d . . . . .
C4 C 0.8754(4) -0.3570(4) 0.7944(4) 0.0690(9) Uani 1 1 d . . . . .
C5 C 0.7155(4) -0.2686(4) 0.8886(4) 0.0660(9) Uani 1 1 d . . . . .
C6 C 0.6155(4) -0.1276(3) 0.8312(3) 0.0557(8) Uani 1 1 d . . . . .
C7 C 0.5633(3) 0.0772(3) 0.6185(3) 0.0475(7) Uani 1 1 d . . . . .
C8 C 0.5377(3) 0.2335(3) 0.6656(3) 0.0486(7) Uani 1 1 d . . . . .
C9 C 0.6608(4) 0.2504(4) 0.7072(3) 0.0597(8) Uani 1 1 d . . . . .
C10 C 0.6411(4) 0.3976(4) 0.7470(4) 0.0701(9) Uani 1 1 d . . . . .
C11 C 0.4974(5) 0.5310(3) 0.7474(3) 0.0667(9) Uani 1 1 d . . . . .
C12 C 0.3725(4) 0.5159(3) 0.7080(3) 0.0637(9) Uani 1 1 d . . . . .
C13 C 0.3917(4) 0.3712(3) 0.6682(3) 0.0558(8) Uani 1 1 d . . . . .
C14 C 0.4944(3) 0.0739(3) 0.5231(3) 0.0504(7) Uani 1 1 d . . . . .
C100 C 1.0515(5) 0.1177(4) 0.8722(4) 0.0924(12) Uani 1 1 d . . . . .
H10A H 1.1607 0.1255 0.8665 0.111 Uiso 1 1 calc R U . . .
H10B H 1.0232 0.1916 0.7903 0.111 Uiso 1 1 calc R U . . .
C101 C 1.0787(6) -0.0529(4) 0.8531(4) 0.0992(14) Uani 1 1 d . . . . .
H10C H 1.1875 -0.0879 0.7686 0.119 Uiso 1 1 calc R U . . .
H10D H 0.9832 -0.0545 0.8307 0.119 Uiso 1 1 calc R U . . .
C102 C 1.0869(7) -0.1712(5) 0.9881(4) 0.1218(18) Uani 1 1 d . . . . .
H10E H 1.0819 -0.2743 0.9760 0.146 Uiso 1 1 calc R U . . .
H10F H 1.1996 -0.1917 0.9940 0.146 Uiso 1 1 calc R U . . .
H2 H 0.876(4) -0.129(3) 0.485(3) 0.064(8) Uiso 1 1 d . . . . .
H3 H 1.036(4) -0.380(4) 0.579(3) 0.091(10) Uiso 1 1 d . . . . .
H4 H 0.951(4) -0.452(3) 0.831(3) 0.069(8) Uiso 1 1 d . . . . .
H5 H 0.668(4) -0.303(4) 0.994(4) 0.087(10) Uiso 1 1 d . . . . .
H6 H 0.506(4) -0.057(3) 0.895(3) 0.061(7) Uiso 1 1 d . . . . .
H9 H 0.757(4) 0.149(3) 0.710(3) 0.061(8) Uiso 1 1 d . . . . .
H10 H 0.737(4) 0.408(3) 0.773(3) 0.077(9) Uiso 1 1 d . . . . .
H11 H 0.485(3) 0.631(3) 0.774(3) 0.064(8) Uiso 1 1 d . . . . .
H12 H 0.279(4) 0.618(3) 0.705(3) 0.077(9) Uiso 1 1 d . . . . .
H13 H 0.302(4) 0.363(3) 0.647(3) 0.076(9) Uiso 1 1 d . . . . .
H14 H 0.428(3) 0.182(3) 0.487(2) 0.047(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.380(4) . ?
C1 C2 1.387(4) . ?
C1 C7 1.498(3) . ?
C2 C3 1.382(4) . ?
C3 C4 1.360(4) . ?
C4 C5 1.377(5) . ?
C5 C6 1.385(4) . ?
C7 C14 1.350(3) . ?
C7 C8 1.482(3) . ?
C8 C9 1.389(4) . ?
C8 C13 1.402(4) . ?
C9 C10 1.386(4) . ?
C10 C11 1.374(4) . ?
C11 C12 1.383(4) . ?
C12 C13 1.367(4) . ?
C14 C14 1.452(5) 2_656 ?
C100 C102 1.447(5) 2_757 ?
C100 C101 1.486(5) . ?
C101 C102 1.491(5) . ?
C102 C100 1.447(5) 2_757 ?

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 C1 C2 118.1(2) . . ?
C6 C1 C7 120.7(2) . . ?
C2 C1 C7 121.2(2) . . ?
C3 C2 C1 120.7(3) . . ?
C4 C3 C2 120.4(3) . . ?
C3 C4 C5 120.0(3) . . ?
C4 C5 C6 119.8(3) . . ?
C1 C6 C5 121.0(3) . . ?
C14 C7 C8 121.4(2) . . ?
C14 C7 C1 122.1(2) . . ?
C8 C7 C1 116.47(19) . . ?
C9 C8 C13 116.9(2) . . ?
C9 C8 C7 120.8(2) . . ?
C13 C8 C7 122.2(2) . . ?
C10 C9 C8 121.4(3) . . ?
C11 C10 C9 120.5(3) . . ?
C10 C11 C12 119.0(3) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 C8 121.5(3) . . ?
C7 C14 C14 125.0(3) . 2_656 ?
C102 C100 C101 113.8(4) 2_757 . ?
C100 C101 C102 112.8(3) . . ?
C100 C102 C101 114.8(3) 2_757 . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 990582'
