# 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_dye_1
_audit_block_doi                 10.5517/ccnx1bx
_database_code_depnum_ccdc_archive 'CCDC 622769'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jp073147m 2007
_audit_update_record             
;
2006-10-02 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 O2'
_chemical_formula_weight         392.47

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.6751(12)
_cell_length_b                   10.2214(12)
_cell_length_c                   10.6522(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.993(2)
_cell_angle_gamma                90.00
_cell_volume                     1045.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3287
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9063
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         29.08
_reflns_number_total             2622
_reflns_number_gt                2264
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0474P)²+0.1474P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(15)
_refine_ls_number_reflns         2622
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.011
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.02197(15) 0.33197(15) 0.37061(16) 0.0271(4) Uani 1 1 d . . .
O2 O 1.02288(16) 0.90601(16) 0.15107(18) 0.0325(4) Uani 1 1 d . . .
C1 C 0.4314(2) 0.6160(2) 0.2166(2) 0.0203(4) Uani 1 1 d . . .
C2 C 0.5558(2) 0.6294(2) 0.2876(2) 0.0220(5) Uani 1 1 d . . .
C11 C 0.3158(2) 0.5372(2) 0.2622(2) 0.0205(4) Uani 1 1 d . . .
C12 C 0.1872(2) 0.5951(2) 0.2682(2) 0.0216(4) Uani 1 1 d . . .
H12A H 0.1747 0.6848 0.2460 0.026 Uiso 1 1 calc R . .
C13 C 0.0772(2) 0.5258(2) 0.3055(2) 0.0210(4) Uani 1 1 d . . .
H13A H -0.0092 0.5682 0.3114 0.025 Uiso 1 1 calc R . .
C14 C 0.0931(2) 0.3929(2) 0.3346(2) 0.0202(4) Uani 1 1 d . . .
C15 C 0.2198(2) 0.3318(2) 0.3263(2) 0.0203(4) Uani 1 1 d . . .
H15A H 0.2308 0.2411 0.3441 0.024 Uiso 1 1 calc R . .
C16 C 0.3306(2) 0.4047(2) 0.2916(2) 0.0217(4) Uani 1 1 d . . .
H16A H 0.4179 0.3633 0.2879 0.026 Uiso 1 1 calc R . .
C17 C -0.0135(2) 0.1946(2) 0.3920(2) 0.0275(5) Uani 1 1 d . . .
H17A H -0.1027 0.1626 0.4147 0.041 Uiso 1 1 calc R . .
H17B H 0.0603 0.1761 0.4612 0.041 Uiso 1 1 calc R . .
H17C H 0.0078 0.1505 0.3150 0.041 Uiso 1 1 calc R . .
C21 C 0.6783(2) 0.6985(2) 0.2442(2) 0.0203(4) Uani 1 1 d . . .
C22 C 0.7534(2) 0.7858(2) 0.3275(2) 0.0228(5) Uani 1 1 d . . .
H22A H 0.7251 0.7997 0.4087 0.027 Uiso 1 1 calc R . .
C23 C 0.8675(2) 0.8522(2) 0.2945(2) 0.0240(5) Uani 1 1 d . . .
H23A H 0.9171 0.9107 0.3530 0.029 Uiso 1 1 calc R . .
C24 C 0.9101(2) 0.8341(2) 0.1763(2) 0.0233(5) Uani 1 1 d . . .
C25 C 0.8392(2) 0.7467(2) 0.0920(2) 0.0242(5) Uani 1 1 d . . .
H25A H 0.8682 0.7330 0.0110 0.029 Uiso 1 1 calc R . .
C26 C 0.7250(2) 0.6794(2) 0.1274(2) 0.0233(5) Uani 1 1 d . . .
H26A H 0.6777 0.6187 0.0699 0.028 Uiso 1 1 calc R . .
C27 C 1.0628(3) 0.8973(3) 0.0266(3) 0.0389(7) Uani 1 1 d . . .
H27A H 1.1412 0.9564 0.0194 0.058 Uiso 1 1 calc R . .
H27B H 0.9840 0.9222 -0.0354 0.058 Uiso 1 1 calc R . .
H27C H 1.0906 0.8072 0.0104 0.058 Uiso 1 1 calc R . .
C31 C 0.3973(2) 0.6715(2) 0.0873(2) 0.0202(5) Uani 1 1 d . . .
C32 C 0.4370(2) 0.7964(2) 0.0523(2) 0.0222(5) Uani 1 1 d . . .
H32A H 0.4871 0.8518 0.1134 0.027 Uiso 1 1 calc R . .
C33 C 0.4041(2) 0.8401(2) -0.0702(2) 0.0262(5) Uani 1 1 d . . .
H33A H 0.4335 0.9246 -0.0928 0.031 Uiso 1 1 calc R . .
C34 C 0.3289(3) 0.7628(2) -0.1606(2) 0.0291(5) Uani 1 1 d . . .
H34A H 0.3063 0.7938 -0.2447 0.035 Uiso 1 1 calc R . .
C35 C 0.2868(2) 0.6389(2) -0.1267(2) 0.0279(5) Uani 1 1 d . . .
H35A H 0.2350 0.5847 -0.1878 0.034 Uiso 1 1 calc R . .
C36 C 0.3203(2) 0.5944(2) -0.0042(2) 0.0226(5) Uani 1 1 d . . .
H36A H 0.2903 0.5099 0.0181 0.027 Uiso 1 1 calc R . .
C41 C 0.5835(2) 0.5737(2) 0.4185(2) 0.0202(4) Uani 1 1 d . . .
C42 C 0.7009(2) 0.4943(2) 0.4467(2) 0.0217(5) Uani 1 1 d . . .
H42A H 0.7600 0.4775 0.3836 0.026 Uiso 1 1 calc R . .
C43 C 0.7315(2) 0.4400(2) 0.5660(2) 0.0282(5) Uani 1 1 d . . .
H43A H 0.8108 0.3852 0.5839 0.034 Uiso 1 1 calc R . .
C44 C 0.6475(3) 0.4653(3) 0.6592(3) 0.0330(6) Uani 1 1 d . . .
H44A H 0.6684 0.4277 0.7409 0.040 Uiso 1 1 calc R . .
C45 C 0.5324(3) 0.5460(3) 0.6325(2) 0.0327(6) Uani 1 1 d . . .
H45A H 0.4752 0.5647 0.6966 0.039 Uiso 1 1 calc R . .
C46 C 0.5003(2) 0.5992(2) 0.5136(2) 0.0251(5) Uani 1 1 d . . .
H46A H 0.4207 0.6537 0.4964 0.030 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
O1 C14 1.371(2) . ?
O1 C17 1.423(3) . ?
O2 C24 1.369(3) . ?
O2 C27 1.428(3) . ?
C1 C2 1.348(3) . ?
C1 C31 1.489(3) . ?
C1 C11 1.505(3) . ?
C2 C21 1.500(3) . ?
C2 C41 1.500(3) . ?
C11 C12 1.386(3) . ?
C11 C16 1.394(3) . ?
C12 C13 1.377(3) . ?
C13 C14 1.398(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.392(3) . ?
C21 C26 1.389(3) . ?
C21 C22 1.398(3) . ?
C22 C23 1.377(3) . ?
C23 C24 1.384(3) . ?
C24 C25 1.387(3) . ?
C25 C26 1.391(3) . ?
C31 C36 1.396(3) . ?
C31 C32 1.397(3) . ?
C32 C33 1.379(3) . ?
C33 C34 1.383(3) . ?
C34 C35 1.391(4) . ?
C35 C36 1.382(3) . ?
C41 C46 1.394(3) . ?
C41 C42 1.398(3) . ?
C42 C43 1.385(3) . ?
C43 C44 1.382(4) . ?
C44 C45 1.388(4) . ?
C45 C46 1.378(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
C14 O1 C17 117.38(18) . . ?
C24 O2 C27 117.4(2) . . ?
C2 C1 C31 124.19(19) . . ?
C2 C1 C11 121.42(19) . . ?
C31 C1 C11 114.35(18) . . ?
C1 C2 C21 124.1(2) . . ?
C1 C2 C41 121.93(19) . . ?
C21 C2 C41 113.97(18) . . ?
C12 C11 C16 118.22(19) . . ?
C12 C11 C1 119.53(18) . . ?
C16 C11 C1 122.14(19) . . ?
C13 C12 C11 121.57(19) . . ?
C12 C13 C14 119.7(2) . . ?
O1 C14 C15 124.58(18) . . ?
O1 C14 C13 115.58(19) . . ?
C15 C14 C13 119.8(2) . . ?
C14 C15 C16 119.41(19) . . ?
C15 C16 C11 121.23(19) . . ?
C26 C21 C22 117.2(2) . . ?
C26 C21 C2 124.4(2) . . ?
C22 C21 C2 118.3(2) . . ?
C23 C22 C21 121.6(2) . . ?
C22 C23 C24 120.1(2) . . ?
O2 C24 C23 116.0(2) . . ?
O2 C24 C25 124.2(2) . . ?
C23 C24 C25 119.8(2) . . ?
C24 C25 C26 119.3(2) . . ?
C21 C26 C25 122.0(2) . . ?
C36 C31 C32 118.0(2) . . ?
C36 C31 C1 118.05(19) . . ?
C32 C31 C1 123.9(2) . . ?
C33 C32 C31 120.6(2) . . ?
C32 C33 C34 121.0(2) . . ?
C33 C34 C35 119.0(2) . . ?
C36 C35 C34 120.2(2) . . ?
C35 C36 C31 121.1(2) . . ?
C46 C41 C42 118.6(2) . . ?
C46 C41 C2 123.4(2) . . ?
C42 C41 C2 117.98(19) . . ?
C43 C42 C41 120.5(2) . . ?
C44 C43 C42 120.3(2) . . ?
C43 C44 C45 119.4(2) . . ?
C46 C45 C44 120.6(2) . . ?
C45 C46 C41 120.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040


