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

#######################################################################
#
#                 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_global
#=============================================================================
# cif data for "siu01" (suppl. information)
#=============================================================================


data_siu1
#TrackingRef 'siu01.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16'
_chemical_formula_weight         196.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   7.5687(3)
_cell_length_b                   16.9200(5)
_cell_length_c                   9.6449(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.885(4)
_cell_angle_gamma                90.00
_cell_volume                     1161.50(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11393
_cell_measurement_theta_min      4.8719
_cell_measurement_theta_max      75.6996

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3543
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19029
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0093
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.23
_diffrn_reflns_theta_max         75.89
_reflns_number_total             2410
_reflns_number_gt                2226
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.2634P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2410
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.47436(12) 0.73329(6) 0.22025(9) 0.0224(2) Uani 1 1 d . . .
C2 C 0.47755(12) 0.66210(6) 0.21539(9) 0.0224(2) Uani 1 1 d . . .
C3 C 0.47737(12) 0.58072(6) 0.20886(10) 0.0231(2) Uani 1 1 d . . .
C4 C 0.47157(12) 0.50961(6) 0.19997(10) 0.0230(2) Uani 1 1 d . . .
C5 C 0.46252(12) 0.42334(5) 0.19163(10) 0.0231(2) Uani 1 1 d . . .
H5A H 0.5022 0.4055 0.1089 0.028 Uiso 1 1 calc R . .
H5B H 0.3308 0.4063 0.1705 0.028 Uiso 1 1 calc R . .
C6 C 0.58736(12) 0.38363(5) 0.33432(10) 0.0211(2) Uani 1 1 d . . .
H6A H 0.7192 0.4004 0.3551 0.025 Uiso 1 1 calc R . .
H6B H 0.5482 0.4017 0.4172 0.025 Uiso 1 1 calc R . .
C7 C 0.57673(13) 0.29364(5) 0.32567(10) 0.0233(2) Uani 1 1 d . . .
H7A H 0.4454 0.2767 0.3068 0.028 Uiso 1 1 calc R . .
H7B H 0.6143 0.2755 0.2422 0.028 Uiso 1 1 calc R . .
C8 C 0.70403(14) 0.25537(5) 0.46773(10) 0.0261(2) Uani 1 1 d . . .
H8A H 0.8345 0.2713 0.4858 0.039 Uiso 1 1 calc R . .
H8B H 0.6937 0.1977 0.4583 0.039 Uiso 1 1 calc R . .
H8C H 0.6657 0.2725 0.5503 0.039 Uiso 1 1 calc R . .
C9 C 0.47146(12) 0.81802(5) 0.22447(9) 0.0205(2) Uani 1 1 d . . .
C10 C 0.57491(12) 0.85893(6) 0.35318(10) 0.0228(2) Uani 1 1 d . . .
H10 H 0.6451 0.8304 0.4391 0.027 Uiso 1 1 calc R . .
C11 C 0.57477(12) 0.94085(6) 0.35508(10) 0.0228(2) Uani 1 1 d . . .
H11 H 0.6456 0.9678 0.4428 0.027 Uiso 1 1 calc R . .
C12 C 0.47279(12) 0.98472(6) 0.23082(10) 0.0221(2) Uani 1 1 d . . .
C13 C 0.36852(12) 0.94358(5) 0.10368(10) 0.0227(2) Uani 1 1 d . . .
H13 H 0.2971 0.9723 0.0183 0.027 Uiso 1 1 calc R . .
C14 C 0.36737(12) 0.86148(5) 0.09986(10) 0.0223(2) Uani 1 1 d . . .
H14 H 0.2956 0.8347 0.0122 0.027 Uiso 1 1 calc R . .
C15 C 0.47747(14) 1.07372(6) 0.23455(11) 0.0278(2) Uani 1 1 d . . .
H15A H 0.4497 1.0924 0.3211 0.042 Uiso 1 1 calc R . .
H15B H 0.3832 1.0945 0.1449 0.042 Uiso 1 1 calc R . .
H15C H 0.6025 1.0921 0.2401 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
C1 0.0220(4) 0.0233(5) 0.0219(4) 0.0011(3) 0.0077(4) 0.0001(3)
C2 0.0222(4) 0.0223(5) 0.0216(4) 0.0017(3) 0.0063(3) 0.0002(3)
C3 0.0228(4) 0.0222(5) 0.0227(4) 0.0017(3) 0.0056(3) 0.0006(3)
C4 0.0216(4) 0.0233(5) 0.0219(4) 0.0003(3) 0.0045(3) 0.0005(3)
C5 0.0233(4) 0.0188(5) 0.0248(4) -0.0015(3) 0.0051(3) -0.0005(3)
C6 0.0215(4) 0.0183(4) 0.0226(4) -0.0015(3) 0.0065(4) -0.0009(3)
C7 0.0246(4) 0.0185(4) 0.0258(5) -0.0012(3) 0.0073(4) -0.0014(3)
C8 0.0325(5) 0.0202(4) 0.0260(5) 0.0013(3) 0.0102(4) -0.0004(4)
C9 0.0210(4) 0.0185(4) 0.0233(5) 0.0014(3) 0.0091(4) -0.0002(3)
C10 0.0224(4) 0.0242(5) 0.0208(4) 0.0026(3) 0.0061(3) 0.0013(3)
C11 0.0225(4) 0.0235(5) 0.0211(4) -0.0022(3) 0.0056(3) -0.0016(3)
C12 0.0220(4) 0.0203(5) 0.0253(4) 0.0005(3) 0.0099(4) 0.0002(3)
C13 0.0233(4) 0.0222(5) 0.0212(4) 0.0034(3) 0.0057(4) 0.0021(3)
C14 0.0221(4) 0.0226(5) 0.0207(4) -0.0008(3) 0.0053(3) -0.0016(3)
C15 0.0321(5) 0.0199(5) 0.0307(5) 0.0001(4) 0.0101(4) -0.0001(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.2061(13) . ?
C1 C9 1.4345(12) . ?
C2 C3 1.3783(12) . ?
C3 C4 1.2060(13) . ?
C4 C5 1.4622(12) . ?
C5 C6 1.5342(12) . ?
C6 C7 1.5255(11) . ?
C7 C8 1.5254(13) . ?
C9 C14 1.4007(12) . ?
C9 C10 1.4043(13) . ?
C10 C11 1.3863(12) . ?
C11 C12 1.3977(13) . ?
C12 C13 1.3973(12) . ?
C12 C15 1.5066(12) . ?
C13 C14 1.3897(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 179.26(9) . . ?
C1 C2 C3 178.87(9) . . ?
C4 C3 C2 177.94(9) . . ?
C3 C4 C5 178.75(9) . . ?
C4 C5 C6 112.63(7) . . ?
C7 C6 C5 112.53(7) . . ?
C8 C7 C6 111.66(7) . . ?
C14 C9 C10 118.78(9) . . ?
C14 C9 C1 120.65(8) . . ?
C10 C9 C1 120.56(8) . . ?
C11 C10 C9 120.13(8) . . ?
C10 C11 C12 121.48(8) . . ?
C13 C12 C11 118.06(9) . . ?
C13 C12 C15 121.37(8) . . ?
C11 C12 C15 120.57(8) . . ?
C14 C13 C12 121.18(8) . . ?
C13 C14 C9 120.36(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 -111(8) . . . . ?
C1 C2 C3 C4 23(6) . . . . ?
C2 C3 C4 C5 -85(5) . . . . ?
C3 C4 C5 C6 -67(4) . . . . ?
C4 C5 C6 C7 179.64(7) . . . . ?
C5 C6 C7 C8 179.15(8) . . . . ?
C2 C1 C9 C14 58(8) . . . . ?
C2 C1 C9 C10 -122(8) . . . . ?
C14 C9 C10 C11 -0.75(12) . . . . ?
C1 C9 C10 C11 178.47(8) . . . . ?
C9 C10 C11 C12 0.14(13) . . . . ?
C10 C11 C12 C13 0.57(13) . . . . ?
C10 C11 C12 C15 -178.90(8) . . . . ?
C11 C12 C13 C14 -0.67(13) . . . . ?
C15 C12 C13 C14 178.79(8) . . . . ?
C12 C13 C14 C9 0.06(13) . . . . ?
C10 C9 C14 C13 0.66(12) . . . . ?
C1 C9 C14 C13 -178.56(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.033
_iucr_refine_instructions_details 
;
TITL siu1 in P2(1)/n
CELL 1.54184 7.568705 16.919972 9.644913 90.0000 109.8854 90.0000
ZERR 4.00 0.000300 0.000500 0.000400 0.0000 0.0040 0.0000
LATT 1
SYMM -x+1/2, y+1/2,-z+1/2
SFAC C H
UNIT 60.00 64.00

TEMP -173
SIZE 0.3 0.15 0.1
ACTA 150
CONF

OMIT 1 5 4

MERG 2
FMAP 2
PLAN 10
L.S. 4

WGHT 0.055100 0.263400
FVAR 6.91730
C1 1 0.474357 0.733290 0.220251 11.00000 0.02203 0.02335 =
0.02192 0.00114 0.00773 0.00013
C2 1 0.477548 0.662095 0.215386 11.00000 0.02221 0.02232 =
0.02164 0.00175 0.00628 0.00017
C3 1 0.477372 0.580718 0.208861 11.00000 0.02284 0.02220 =
0.02266 0.00169 0.00564 0.00058
C4 1 0.471571 0.509607 0.199974 11.00000 0.02162 0.02327 =
0.02193 0.00027 0.00455 0.00054
C5 1 0.462523 0.423341 0.191626 11.00000 0.02325 0.01882 =
0.02480 -0.00150 0.00507 -0.00048
AFIX 23
H5A 2 0.502173 0.405542 0.108909 11.00000 -1.20000
H5B 2 0.330816 0.406323 0.170548 11.00000 -1.20000
AFIX 0
C6 1 0.587355 0.383630 0.334319 11.00000 0.02151 0.01829 =
0.02263 -0.00150 0.00650 -0.00090
AFIX 23
H6A 2 0.719206 0.400351 0.355071 11.00000 -1.20000
H6B 2 0.548245 0.401665 0.417164 11.00000 -1.20000
AFIX 0
C7 1 0.576726 0.293644 0.325673 11.00000 0.02464 0.01854 =
0.02584 -0.00124 0.00732 -0.00136
AFIX 23
H7A 2 0.445408 0.276687 0.306756 11.00000 -1.20000
H7B 2 0.614299 0.275457 0.242165 11.00000 -1.20000
AFIX 0
C8 1 0.704025 0.255373 0.467726 11.00000 0.03246 0.02024 =
0.02596 0.00130 0.01024 -0.00037
AFIX 137
H8A 2 0.834462 0.271268 0.485762 11.00000 -1.50000
H8B 2 0.693700 0.197740 0.458347 11.00000 -1.50000
H8C 2 0.665698 0.272524 0.550334 11.00000 -1.50000
AFIX 0
C9 1 0.471463 0.818016 0.224475 11.00000 0.02098 0.01850 =
0.02325 0.00140 0.00906 -0.00022
C10 1 0.574905 0.858930 0.353178 11.00000 0.02241 0.02417 =
0.02082 0.00257 0.00610 0.00126
AFIX 43
H10 2 0.645115 0.830412 0.439109 11.00000 -1.20000
AFIX 0
C11 1 0.574768 0.940854 0.355082 11.00000 0.02248 0.02345 =
0.02112 -0.00218 0.00562 -0.00162
AFIX 43
H11 2 0.645575 0.967790 0.442820 11.00000 -1.20000
AFIX 0
C12 1 0.472794 0.984715 0.230818 11.00000 0.02203 0.02025 =
0.02530 0.00053 0.00990 0.00016
C13 1 0.368520 0.943582 0.103679 11.00000 0.02332 0.02220 =
0.02115 0.00341 0.00566 0.00208
AFIX 43
H13 2 0.297134 0.972261 0.018326 11.00000 -1.20000
AFIX 0
C14 1 0.367370 0.861477 0.099856 11.00000 0.02215 0.02264 =
0.02070 -0.00083 0.00529 -0.00157
AFIX 43
H14 2 0.295591 0.834678 0.012242 11.00000 -1.20000
AFIX 0
C15 1 0.477465 1.073722 0.234553 11.00000 0.03214 0.01989 =
0.03075 0.00014 0.01005 -0.00010
AFIX 137
H15A 2 0.449739 1.092440 0.321106 11.00000 -1.50000
H15B 2 0.383242 1.094497 0.144894 11.00000 -1.50000
H15C 2 0.602454 1.092128 0.240087 11.00000 -1.50000
HKLF 4

;

#=============================================================================
# end of cif data for "siu01" (suppl. information)
#=============================================================================



_database_code_depnum_ccdc_archive 'CCDC 935939'