# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 Cl2 O2'
_chemical_formula_sum            'C24 H20 Cl2 O2'
_chemical_formula_weight         411.30

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   9.6685(19)
_cell_length_b                   22.865(5)
_cell_length_c                   9.6903(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.41(3)
_cell_angle_gamma                90.00
_cell_volume                     1980.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5718
_cell_measurement_theta_min      1.7813
_cell_measurement_theta_max      25.3291

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6406
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13825
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         0.89
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3618
_reflns_number_gt                3396
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0485P)²+6.7338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3618
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0900
_refine_ls_wR_factor_ref         0.2003
_refine_ls_wR_factor_gt          0.1972
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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
Cl1 Cl 0.51889(16) 0.10141(5) 0.61135(15) 0.0464(4) Uani 1 1 d . . .
Cl2 Cl 0.01261(16) 0.92464(6) 0.41225(16) 0.0509(4) Uani 1 1 d . . .
O1 O 0.3093(4) 0.58092(14) 0.2951(4) 0.0412(8) Uani 1 1 d . . .
O2 O 0.1786(4) 0.44305(14) 0.6979(4) 0.0401(8) Uani 1 1 d . . .
C1 C 0.4774(5) 0.17476(19) 0.5650(5) 0.0329(10) Uani 1 1 d . . .
C2 C 0.4171(5) 0.1916(2) 0.4159(5) 0.0373(11) Uani 1 1 d . . .
H2A H 0.3987 0.1634 0.3388 0.045 Uiso 1 1 calc R . .
C3 C 0.3844(5) 0.2499(2) 0.3819(5) 0.0365(10) Uani 1 1 d . . .
H3A H 0.3454 0.2619 0.2804 0.044 Uiso 1 1 calc R . .
C4 C 0.4078(5) 0.29168(19) 0.4943(5) 0.0328(10) Uani 1 1 d . . .
C5 C 0.4724(5) 0.2737(2) 0.6409(5) 0.0377(11) Uani 1 1 d . . .
H5A H 0.4930 0.3019 0.7183 0.045 Uiso 1 1 calc R . .
C6 C 0.5078(5) 0.2158(2) 0.6779(5) 0.0367(10) Uani 1 1 d . . .
H6A H 0.5524 0.2042 0.7796 0.044 Uiso 1 1 calc R . .
C7 C 0.3616(5) 0.35288(19) 0.4531(5) 0.0357(10) Uani 1 1 d . . .
H7A H 0.3618 0.3674 0.3613 0.043 Uiso 1 1 calc R . .
C8 C 0.3197(5) 0.38859(19) 0.5382(5) 0.0365(10) Uani 1 1 d . . .
H8A H 0.3163 0.3721 0.6268 0.044 Uiso 1 1 calc R . .
C9 C 0.2781(5) 0.45054(19) 0.5116(5) 0.0321(10) Uani 1 1 d . . .
C10 C 0.3116(5) 0.4849(2) 0.4080(5) 0.0356(10) Uani 1 1 d . . .
H10A H 0.3541 0.4670 0.3449 0.043 Uiso 1 1 calc R . .
C11 C 0.2836(5) 0.5447(2) 0.3961(5) 0.0365(10) Uani 1 1 d . . .
C12 C 0.2219(5) 0.57244(19) 0.4893(5) 0.0332(10) Uani 1 1 d . . .
C13 C 0.1846(5) 0.53851(19) 0.5890(5) 0.0330(10) Uani 1 1 d . . .
H13A H 0.1400 0.5564 0.6504 0.040 Uiso 1 1 calc R . .
C14 C 0.2116(5) 0.4788(2) 0.5998(5) 0.0332(10) Uani 1 1 d . . .
C15 C 0.3561(6) 0.5549(2) 0.1869(6) 0.0464(12) Uani 1 1 d . . .
H15A H 0.3703 0.5854 0.1225 0.070 Uiso 1 1 calc R . .
H15B H 0.2797 0.5273 0.1262 0.070 Uiso 1 1 calc R . .
H15C H 0.4507 0.5341 0.2374 0.070 Uiso 1 1 calc R . .
C16 C 0.1154(6) 0.4705(2) 0.7922(6) 0.0435(12) Uani 1 1 d . . .
H16A H 0.0959 0.4410 0.8559 0.065 Uiso 1 1 calc R . .
H16B H 0.0213 0.4896 0.7308 0.065 Uiso 1 1 calc R . .
H16C H 0.1854 0.4997 0.8548 0.065 Uiso 1 1 calc R . .
C17 C 0.2012(5) 0.63633(19) 0.4799(5) 0.0353(10) Uani 1 1 d . . .
H17A H 0.2749 0.6590 0.4617 0.042 Uiso 1 1 calc R . .
C18 C 0.0885(6) 0.66468(19) 0.4947(5) 0.0354(10) Uani 1 1 d . . .
H18A H 0.0143 0.6425 0.5131 0.043 Uiso 1 1 calc R . .
C19 C 0.0712(5) 0.72888(19) 0.4841(5) 0.0336(10) Uani 1 1 d . . .
C20 C 0.1935(5) 0.7664(2) 0.5280(5) 0.0357(10) Uani 1 1 d . . .
H20A H 0.2914 0.7506 0.5726 0.043 Uiso 1 1 calc R . .
C21 C 0.1756(5) 0.8263(2) 0.5081(6) 0.0379(11) Uani 1 1 d . . .
H21A H 0.2604 0.8513 0.5388 0.046 Uiso 1 1 calc R . .
C22 C 0.0341(5) 0.84916(19) 0.4437(5) 0.0347(10) Uani 1 1 d . . .
C23 C -0.0929(6) 0.8141(2) 0.4027(6) 0.0417(11) Uani 1 1 d . . .
H23A H -0.1903 0.8305 0.3602 0.050 Uiso 1 1 calc R . .
C24 C -0.0724(5) 0.7545(2) 0.4257(5) 0.0381(11) Uani 1 1 d . . .
H24A H -0.1578 0.7300 0.4015 0.046 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
Cl1 C1 1.743(5) . ?
Cl2 C22 1.751(4) . ?
O1 C11 1.374(6) . ?
O1 C15 1.422(6) . ?
O2 C14 1.381(5) . ?
O2 C16 1.424(6) . ?
C1 C6 1.385(6) . ?
C1 C2 1.390(7) . ?
C2 C3 1.382(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.401(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.378(7) . ?
C4 C7 1.477(6) . ?
C5 C6 1.382(6) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.329(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.468(6) . ?
C8 H8A 0.9500 . ?
C9 C14 1.407(6) . ?
C9 C10 1.407(6) . ?
C10 C11 1.390(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.409(6) . ?
C12 C13 1.389(6) . ?
C12 C17 1.473(6) . ?
C13 C14 1.386(6) . ?
C13 H13A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.322(6) . ?
C17 H17A 0.9500 . ?
C18 C19 1.477(6) . ?
C18 H18A 0.9500 . ?
C19 C20 1.390(6) . ?
C19 C24 1.411(7) . ?
C20 C21 1.384(6) . ?
C20 H20A 0.9500 . ?
C21 C22 1.373(7) . ?
C21 H21A 0.9500 . ?
C22 C23 1.392(7) . ?
C23 C24 1.382(6) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?

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
C11 O1 C15 117.9(4) . . ?
C14 O2 C16 116.7(4) . . ?
C6 C1 C2 120.9(4) . . ?
C6 C1 Cl1 119.3(4) . . ?
C2 C1 Cl1 119.8(3) . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 121.2(4) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 C7 122.2(4) . . ?
C3 C4 C7 119.5(4) . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 H6A 120.4 . . ?
C1 C6 H6A 120.4 . . ?
C8 C7 C4 123.1(4) . . ?
C8 C7 H7A 118.4 . . ?
C4 C7 H7A 118.4 . . ?
C7 C8 C9 127.7(4) . . ?
C7 C8 H8A 116.1 . . ?
C9 C8 H8A 116.1 . . ?
C14 C9 C10 117.3(4) . . ?
C14 C9 C8 119.7(4) . . ?
C10 C9 C8 122.8(4) . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10A 119.4 . . ?
C9 C10 H10A 119.4 . . ?
O1 C11 C10 124.7(4) . . ?
O1 C11 C12 114.9(4) . . ?
C10 C11 C12 120.4(4) . . ?
C13 C12 C11 118.7(4) . . ?
C13 C12 C17 122.1(4) . . ?
C11 C12 C17 119.1(4) . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
O2 C14 C13 123.3(4) . . ?
O2 C14 C9 115.2(4) . . ?
C13 C14 C9 121.5(4) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C12 125.3(4) . . ?
C18 C17 H17A 117.4 . . ?
C12 C17 H17A 117.4 . . ?
C17 C18 C19 123.8(4) . . ?
C17 C18 H18A 118.1 . . ?
C19 C18 H18A 118.1 . . ?
C20 C19 C24 117.3(4) . . ?
C20 C19 C18 122.1(4) . . ?
C24 C19 C18 120.6(4) . . ?
C21 C20 C19 121.4(5) . . ?
C21 C20 H20A 119.3 . . ?
C19 C20 H20A 119.3 . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21A 120.3 . . ?
C20 C21 H21A 120.3 . . ?
C21 C22 C23 121.9(4) . . ?
C21 C22 Cl2 119.1(4) . . ?
C23 C22 Cl2 119.0(4) . . ?
C24 C23 C22 117.7(5) . . ?
C24 C23 H23A 121.1 . . ?
C22 C23 H23A 121.1 . . ?
C23 C24 C19 122.2(4) . . ?
C23 C24 H24A 118.9 . . ?
C19 C24 H24A 118.9 . . ?

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
C6 C1 C2 C3 -1.5(7) . . . . ?
Cl1 C1 C2 C3 179.7(4) . . . . ?
C1 C2 C3 C4 -1.5(7) . . . . ?
C2 C3 C4 C5 3.6(7) . . . . ?
C2 C3 C4 C7 -175.7(4) . . . . ?
C3 C4 C5 C6 -2.8(7) . . . . ?
C7 C4 C5 C6 176.5(4) . . . . ?
C4 C5 C6 C1 -0.1(7) . . . . ?
C2 C1 C6 C5 2.3(7) . . . . ?
Cl1 C1 C6 C5 -178.9(4) . . . . ?
C5 C4 C7 C8 -28.6(7) . . . . ?
C3 C4 C7 C8 150.7(5) . . . . ?
C4 C7 C8 C9 177.1(4) . . . . ?
C7 C8 C9 C14 168.9(5) . . . . ?
C7 C8 C9 C10 -16.0(8) . . . . ?
C14 C9 C10 C11 1.6(7) . . . . ?
C8 C9 C10 C11 -173.6(4) . . . . ?
C15 O1 C11 C10 5.5(7) . . . . ?
C15 O1 C11 C12 -173.3(4) . . . . ?
C9 C10 C11 O1 -178.1(4) . . . . ?
C9 C10 C11 C12 0.6(7) . . . . ?
O1 C11 C12 C13 176.4(4) . . . . ?
C10 C11 C12 C13 -2.4(7) . . . . ?
O1 C11 C12 C17 -4.5(6) . . . . ?
C10 C11 C12 C17 176.6(4) . . . . ?
C11 C12 C13 C14 2.0(7) . . . . ?
C17 C12 C13 C14 -177.1(4) . . . . ?
C16 O2 C14 C13 -0.8(6) . . . . ?
C16 O2 C14 C9 178.2(4) . . . . ?
C12 C13 C14 O2 179.2(4) . . . . ?
C12 C13 C14 C9 0.3(7) . . . . ?
C10 C9 C14 O2 178.9(4) . . . . ?
C8 C9 C14 O2 -5.7(6) . . . . ?
C10 C9 C14 C13 -2.1(7) . . . . ?
C8 C9 C14 C13 173.3(4) . . . . ?
C13 C12 C17 C18 -37.0(7) . . . . ?
C11 C12 C17 C18 144.0(5) . . . . ?
C12 C17 C18 C19 -179.8(4) . . . . ?
C17 C18 C19 C20 -31.4(7) . . . . ?
C17 C18 C19 C24 147.4(5) . . . . ?
C24 C19 C20 C21 -3.3(7) . . . . ?
C18 C19 C20 C21 175.6(4) . . . . ?
C19 C20 C21 C22 0.0(7) . . . . ?
C20 C21 C22 C23 2.5(7) . . . . ?
C20 C21 C22 Cl2 -177.5(4) . . . . ?
C21 C22 C23 C24 -1.4(7) . . . . ?
Cl2 C22 C23 C24 178.6(4) . . . . ?
C22 C23 C24 C19 -2.1(7) . . . . ?
C20 C19 C24 C23 4.4(7) . . . . ?
C18 C19 C24 C23 -174.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 941301'
