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

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

data_cd212120
_database_code_depnum_ccdc_archive 'CCDC 873625'
_audit_update_record             
;
2012-03-28 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;
#TrackingRef 'cd212120.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12'
_chemical_formula_weight         180.24

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   18.222(9)
_cell_length_b                   5.648(3)
_cell_length_c                   20.014(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.925(11)
_cell_angle_gamma                90.00
_cell_volume                     2040.1(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    858
_cell_measurement_theta_min      4.407
_cell_measurement_theta_max      44.360

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0453
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10710
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_sigmaI/netI    0.1039
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.13
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3787
_reflns_number_gt                1866
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1388P)²+0.9994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1948
_refine_ls_R_factor_gt           0.1149
_refine_ls_wR_factor_ref         0.3205
_refine_ls_wR_factor_gt          0.2699
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_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 0.4033(2) 0.3285(8) 0.3832(2) 0.0491(11) Uani 1 1 d . . .
C2 C 0.4601(3) 0.1255(8) 0.3971(2) 0.0552(13) Uani 1 1 d . . .
H2A H 0.4413 -0.0129 0.4179 0.066 Uiso 1 1 calc R . .
H2B H 0.5077 0.1744 0.4208 0.066 Uiso 1 1 calc R . .
C3 C 0.4579(3) 0.1050(9) 0.3185(2) 0.0667(15) Uani 1 1 d . . .
H3A H 0.5044 0.1437 0.3026 0.080 Uiso 1 1 calc R . .
H3B H 0.4378 -0.0433 0.2996 0.080 Uiso 1 1 calc R . .
C4 C 0.4016(3) 0.3106(8) 0.3134(2) 0.0514(12) Uani 1 1 d . . .
C5 C 0.3565(3) 0.4493(10) 0.2683(2) 0.0631(14) Uani 1 1 d . . .
H5 H 0.3544 0.4327 0.2218 0.076 Uiso 1 1 calc R . .
C6 C 0.3137(3) 0.6180(9) 0.2976(3) 0.0645(14) Uani 1 1 d . . .
H6 H 0.2830 0.7190 0.2697 0.077 Uiso 1 1 calc R . .
C7 C 0.3161(3) 0.6380(8) 0.3669(2) 0.0544(13) Uani 1 1 d . . .
H7 H 0.2866 0.7526 0.3835 0.065 Uiso 1 1 calc R . .
C8 C 0.3610(2) 0.4930(7) 0.4141(2) 0.0456(11) Uani 1 1 d . . .
C9 C 0.3621(2) 0.5142(7) 0.4889(2) 0.0450(11) Uani 1 1 d . . .
C10 C 0.3220(3) 0.6888(9) 0.5179(2) 0.0602(14) Uani 1 1 d . . .
H10 H 0.2943 0.7977 0.4901 0.072 Uiso 1 1 calc R . .
C11 C 0.3225(3) 0.7028(10) 0.5866(2) 0.0654(15) Uani 1 1 d . . .
H11 H 0.2951 0.8209 0.6042 0.078 Uiso 1 1 calc R . .
C12 C 0.3627(3) 0.5456(9) 0.6301(2) 0.0621(14) Uani 1 1 d . . .
H12 H 0.3620 0.5538 0.6764 0.075 Uiso 1 1 calc R . .
C13 C 0.4042(4) 0.3744(10) 0.6021(3) 0.0784(18) Uani 1 1 d . . .
H13 H 0.4329 0.2688 0.6303 0.094 Uiso 1 1 calc R . .
C14 C 0.4034(3) 0.3594(9) 0.5334(2) 0.0673(16) Uani 1 1 d . . .
H14 H 0.4313 0.2421 0.5161 0.081 Uiso 1 1 calc R . .
C15 C 0.0953(2) 0.8378(8) 0.4077(2) 0.0449(11) Uani 1 1 d . . .
C16 C 0.0382(3) 0.6365(8) 0.4081(2) 0.0555(13) Uani 1 1 d . . .
H16A H -0.0090 0.6862 0.4208 0.067 Uiso 1 1 calc R . .
H16B H 0.0570 0.4968 0.4329 0.067 Uiso 1 1 calc R . .
C17 C 0.0393(3) 0.6201(9) 0.3291(2) 0.0648(15) Uani 1 1 d . . .
H17A H 0.0589 0.4725 0.3142 0.078 Uiso 1 1 calc R . .
H17B H -0.0073 0.6612 0.3020 0.078 Uiso 1 1 calc R . .
C18 C 0.0961(2) 0.8244(8) 0.3388(2) 0.0470(11) Uani 1 1 d . . .
C19 C 0.1392(3) 0.9692(9) 0.3043(2) 0.0577(13) Uani 1 1 d . . .
H19 H 0.1392 0.9582 0.2579 0.069 Uiso 1 1 calc R . .
C20 C 0.1830(3) 1.1336(9) 0.3443(2) 0.0597(13) Uani 1 1 d . . .
H20 H 0.2136 1.2343 0.3239 0.072 Uiso 1 1 calc R . .
C21 C 0.1823(3) 1.1515(8) 0.4137(2) 0.0545(13) Uani 1 1 d . . .
H21 H 0.2121 1.2650 0.4377 0.065 Uiso 1 1 calc R . .
C22 C 0.1377(2) 1.0029(7) 0.4495(2) 0.0471(11) Uani 1 1 d . . .
C23 C 0.1383(2) 1.0187(7) 0.5238(2) 0.0436(11) Uani 1 1 d . . .
C24 C 0.1784(3) 1.1928(9) 0.5637(2) 0.0603(13) Uani 1 1 d . . .
H24 H 0.2050 1.3047 0.5428 0.072 Uiso 1 1 calc R . .
C25 C 0.1798(3) 1.2032(10) 0.6325(3) 0.0673(15) Uani 1 1 d . . .
H25 H 0.2071 1.3207 0.6571 0.081 Uiso 1 1 calc R . .
C26 C 0.1407(3) 1.0404(10) 0.6654(3) 0.0684(15) Uani 1 1 d . . .
H26 H 0.1419 1.0466 0.7120 0.082 Uiso 1 1 calc R . .
C27 C 0.0997(4) 0.8675(10) 0.6275(3) 0.0787(18) Uani 1 1 d . . .
H27 H 0.0727 0.7572 0.6486 0.094 Uiso 1 1 calc R . .
C28 C 0.0993(3) 0.8603(9) 0.5584(2) 0.0679(16) Uani 1 1 d . . .
H28 H 0.0715 0.7434 0.5339 0.081 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.398(6) . ?
C1 C8 1.404(6) . ?
C1 C2 1.544(6) . ?
C2 C3 1.571(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.544(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.378(6) . ?
C5 C6 1.410(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.421(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.498(6) . ?
C9 C14 1.392(6) . ?
C9 C10 1.401(6) . ?
C10 C11 1.376(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C18 1.383(5) . ?
C15 C22 1.410(6) . ?
C15 C16 1.542(6) . ?
C16 C17 1.588(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.545(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.383(6) . ?
C19 C20 1.402(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.394(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.428(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.488(6) . ?
C23 C28 1.385(6) . ?
C23 C24 1.406(6) . ?
C24 C25 1.375(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.389(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(6) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
C4 C1 C8 123.4(4) . . ?
C4 C1 C2 92.7(4) . . ?
C8 C1 C2 143.9(4) . . ?
C1 C2 C3 87.2(3) . . ?
C1 C2 H2A 114.1 . . ?
C3 C2 H2A 114.1 . . ?
C1 C2 H2B 114.1 . . ?
C3 C2 H2B 114.1 . . ?
H2A C2 H2B 111.3 . . ?
C4 C3 C2 86.3(3) . . ?
C4 C3 H3A 114.3 . . ?
C2 C3 H3A 114.3 . . ?
C4 C3 H3B 114.3 . . ?
C2 C3 H3B 114.3 . . ?
H3A C3 H3B 111.4 . . ?
C5 C4 C1 122.9(4) . . ?
C5 C4 C3 143.4(4) . . ?
C1 C4 C3 93.7(4) . . ?
C4 C5 C6 115.2(4) . . ?
C4 C5 H5 122.4 . . ?
C6 C5 H5 122.4 . . ?
C7 C6 C5 121.9(5) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 123.6(5) . . ?
C6 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C1 C8 C7 112.9(4) . . ?
C1 C8 C9 124.1(4) . . ?
C7 C8 C9 123.0(4) . . ?
C14 C9 C10 116.3(4) . . ?
C14 C9 C8 121.4(4) . . ?
C10 C9 C8 122.3(4) . . ?
C11 C10 C9 121.5(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 121.5(5) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 117.7(5) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C14 C13 C12 120.8(5) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 122.1(5) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
C18 C15 C22 123.1(4) . . ?
C18 C15 C16 93.7(4) . . ?
C22 C15 C16 143.1(4) . . ?
C15 C16 C17 86.4(3) . . ?
C15 C16 H16A 114.3 . . ?
C17 C16 H16A 114.3 . . ?
C15 C16 H16B 114.3 . . ?
C17 C16 H16B 114.3 . . ?
H16A C16 H16B 111.4 . . ?
C18 C17 C16 86.0(3) . . ?
C18 C17 H17A 114.3 . . ?
C16 C17 H17A 114.3 . . ?
C18 C17 H17B 114.3 . . ?
C16 C17 H17B 114.3 . . ?
H17A C17 H17B 111.5 . . ?
C19 C18 C15 123.4(4) . . ?
C19 C18 C17 142.7(4) . . ?
C15 C18 C17 93.9(4) . . ?
C18 C19 C20 115.1(4) . . ?
C18 C19 H19 122.4 . . ?
C20 C19 H19 122.4 . . ?
C21 C20 C19 122.3(5) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C20 C21 C22 122.8(4) . . ?
C20 C21 H21 118.6 . . ?
C22 C21 H21 118.6 . . ?
C15 C22 C21 113.2(4) . . ?
C15 C22 C23 124.0(4) . . ?
C21 C22 C23 122.7(4) . . ?
C28 C23 C24 115.5(4) . . ?
C28 C23 C22 121.8(4) . . ?
C24 C23 C22 122.7(4) . . ?
C25 C24 C23 122.3(5) . . ?
C25 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C24 C25 C26 120.6(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C27 118.8(5) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C28 C27 C26 119.6(5) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C23 123.3(5) . . ?
C27 C28 H28 118.4 . . ?
C23 C28 H28 118.4 . . ?

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
C4 C1 C2 C3 -0.2(4) . . . . ?
C8 C1 C2 C3 179.6(7) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C8 C1 C4 C5 -1.8(7) . . . . ?
C2 C1 C4 C5 178.0(5) . . . . ?
C8 C1 C4 C3 -179.6(4) . . . . ?
C2 C1 C4 C3 0.2(4) . . . . ?
C2 C3 C4 C5 -177.2(7) . . . . ?
C2 C3 C4 C1 -0.2(4) . . . . ?
C1 C4 C5 C6 2.2(7) . . . . ?
C3 C4 C5 C6 178.6(6) . . . . ?
C4 C5 C6 C7 -1.3(7) . . . . ?
C5 C6 C7 C8 0.0(8) . . . . ?
C4 C1 C8 C7 0.3(6) . . . . ?
C2 C1 C8 C7 -179.4(6) . . . . ?
C4 C1 C8 C9 179.9(4) . . . . ?
C2 C1 C8 C9 0.3(9) . . . . ?
C6 C7 C8 C1 0.5(7) . . . . ?
C6 C7 C8 C9 -179.1(4) . . . . ?
C1 C8 C9 C14 -3.6(7) . . . . ?
C7 C8 C9 C14 176.0(5) . . . . ?
C1 C8 C9 C10 176.7(4) . . . . ?
C7 C8 C9 C10 -3.7(7) . . . . ?
C14 C9 C10 C11 -1.1(7) . . . . ?
C8 C9 C10 C11 178.7(4) . . . . ?
C9 C10 C11 C12 0.0(8) . . . . ?
C10 C11 C12 C13 1.4(8) . . . . ?
C11 C12 C13 C14 -1.7(9) . . . . ?
C12 C13 C14 C9 0.7(9) . . . . ?
C10 C9 C14 C13 0.7(8) . . . . ?
C8 C9 C14 C13 -179.0(5) . . . . ?
C18 C15 C16 C17 0.2(4) . . . . ?
C22 C15 C16 C17 178.8(6) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C22 C15 C18 C19 0.9(7) . . . . ?
C16 C15 C18 C19 179.8(4) . . . . ?
C22 C15 C18 C17 -179.2(4) . . . . ?
C16 C15 C18 C17 -0.2(4) . . . . ?
C16 C17 C18 C19 -179.9(6) . . . . ?
C16 C17 C18 C15 0.2(4) . . . . ?
C15 C18 C19 C20 0.0(7) . . . . ?
C17 C18 C19 C20 -179.8(6) . . . . ?
C18 C19 C20 C21 -0.8(7) . . . . ?
C19 C20 C21 C22 0.7(7) . . . . ?
C18 C15 C22 C21 -1.0(6) . . . . ?
C16 C15 C22 C21 -179.2(6) . . . . ?
C18 C15 C22 C23 -179.3(4) . . . . ?
C16 C15 C22 C23 2.4(9) . . . . ?
C20 C21 C22 C15 0.2(6) . . . . ?
C20 C21 C22 C23 178.6(4) . . . . ?
C15 C22 C23 C28 3.6(7) . . . . ?
C21 C22 C23 C28 -174.6(5) . . . . ?
C15 C22 C23 C24 -176.9(4) . . . . ?
C21 C22 C23 C24 4.9(7) . . . . ?
C28 C23 C24 C25 0.8(7) . . . . ?
C22 C23 C24 C25 -178.7(4) . . . . ?
C23 C24 C25 C26 -0.2(8) . . . . ?
C24 C25 C26 C27 -0.5(8) . . . . ?
C25 C26 C27 C28 0.6(9) . . . . ?
C26 C27 C28 C23 0.0(9) . . . . ?
C24 C23 C28 C27 -0.7(8) . . . . ?
C22 C23 C28 C27 178.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.077


