# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 884177'
_audit_update_record             
;
2012-05-28 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
#TrackingRef 'ad-205 cif.txt'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 O'
_chemical_formula_sum            'C25 H24 O'
_chemical_formula_weight         340.44

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   19.703(2)
_cell_length_b                   8.2643(5)
_cell_length_c                   23.1696(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3772.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      25.00

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13457
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3315
_reflns_number_gt                2564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0884P)²+5.5316P] 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         3315
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0969
_refine_ls_wR_factor_ref         0.2465
_refine_ls_wR_factor_gt          0.2312
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

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
C24 C 0.2575(2) 0.1493(5) 0.3476(2) 0.0700(13) Uani 1 1 d . . .
H24A H 0.3054 0.1762 0.3416 0.105 Uiso 1 1 calc R . .
H24B H 0.2496 0.0359 0.3372 0.105 Uiso 1 1 calc R . .
H24C H 0.2457 0.1659 0.3883 0.105 Uiso 1 1 calc R . .
O1 O 0.21627(15) 0.2510(4) 0.31246(13) 0.0648(9) Uani 1 1 d . . .
C1 C 0.1140(3) -0.6936(5) 0.49241(19) 0.0726(15) Uani 1 1 d . . .
H1A H 0.1218 -0.7121 0.4512 0.109 Uiso 1 1 calc R . .
H1B H 0.0654 -0.7010 0.5007 0.109 Uiso 1 1 calc R . .
H1C H 0.1385 -0.7756 0.5148 0.109 Uiso 1 1 calc R . .
C2 C 0.1260(4) -0.5055(6) 0.5725(2) 0.118(3) Uani 1 1 d . . .
H2A H 0.1423 -0.3986 0.5844 0.178 Uiso 1 1 calc R . .
H2B H 0.1499 -0.5893 0.5945 0.178 Uiso 1 1 calc R . .
H2C H 0.0772 -0.5135 0.5800 0.178 Uiso 1 1 calc R . .
C3 C 0.2152(3) -0.5267(8) 0.4977(4) 0.140(4) Uani 1 1 d . . .
H3A H 0.2240 -0.5408 0.4564 0.210 Uiso 1 1 calc R . .
H3B H 0.2368 -0.6148 0.5193 0.210 Uiso 1 1 calc R . .
H3C H 0.2340 -0.4228 0.5105 0.210 Uiso 1 1 calc R . .
C4 C 0.1393(2) -0.5292(4) 0.50851(16) 0.0465(10) Uani 1 1 d . . .
C5 C 0.10581(19) -0.3954(4) 0.47282(15) 0.0408(9) Uani 1 1 d . . .
C6 C 0.1005(3) -0.2418(5) 0.4922(2) 0.0797(17) Uani 1 1 d . . .
H6 H 0.1178 -0.2167 0.5294 0.096 Uiso 1 1 calc R . .
C7 C 0.0708(3) -0.1196(5) 0.4601(2) 0.0853(19) Uani 1 1 d . . .
H7 H 0.0694 -0.0133 0.4757 0.102 Uiso 1 1 calc R . .
C8 C 0.04381(18) -0.1469(4) 0.40726(15) 0.0391(9) Uani 1 1 d . . .
C9 C 0.0483(3) -0.3016(5) 0.38685(17) 0.0687(14) Uani 1 1 d . . .
H9 H 0.0302 -0.3261 0.3499 0.082 Uiso 1 1 calc R . .
C10 C 0.0786(3) -0.4232(5) 0.41849(18) 0.0722(15) Uani 1 1 d . . .
H10 H 0.0809 -0.5291 0.4026 0.087 Uiso 1 1 calc R . .
C11 C 0.00694(19) -0.0190(4) 0.37478(14) 0.0386(9) Uani 1 1 d . . .
C12 C -0.0617(2) -0.0206(5) 0.37338(16) 0.0476(10) Uani 1 1 d . . .
H12 H -0.0848 -0.1051 0.3931 0.057 Uiso 1 1 calc R . .
C13 C -0.10110(19) 0.0978(4) 0.34387(15) 0.0415(9) Uani 1 1 d . . .
C14 C -0.1723(2) 0.0926(5) 0.34474(17) 0.0520(10) Uani 1 1 d . . .
H14 H -0.1947 0.0091 0.3655 0.062 Uiso 1 1 calc R . .
C15 C -0.2098(2) 0.2063(5) 0.31608(17) 0.0555(11) Uani 1 1 d . . .
H15 H -0.2580 0.2019 0.3170 0.067 Uiso 1 1 calc R . .
C015 C -0.1772(2) 0.3282(5) 0.28563(17) 0.0556(11) Uani 1 1 d . . .
H015 H -0.2032 0.4074 0.2658 0.067 Uiso 1 1 calc R . .
C16 C -0.1081(2) 0.3351(5) 0.28399(15) 0.0483(10) Uani 1 1 d . . .
H16 H -0.0867 0.4195 0.2629 0.058 Uiso 1 1 calc R . .
C17 C -0.06777(19) 0.2204(4) 0.31271(14) 0.0398(9) Uani 1 1 d . . .
C18 C 0.00590(19) 0.2237(4) 0.31231(13) 0.0377(9) Uani 1 1 d . . .
C19 C 0.0431(2) 0.3414(4) 0.28131(14) 0.0445(10) Uani 1 1 d . . .
H19 H 0.0191 0.4199 0.2593 0.053 Uiso 1 1 calc R . .
C20 C 0.1115(2) 0.3456(5) 0.28202(17) 0.0510(10) Uani 1 1 d . . .
H20 H 0.1350 0.4261 0.2606 0.061 Uiso 1 1 calc R . .
C21 C 0.1477(2) 0.2320(4) 0.31410(16) 0.0451(9) Uani 1 1 d . . .
C22 C 0.1143(2) 0.1134(4) 0.34366(14) 0.0403(9) Uani 1 1 d . . .
H22 H 0.1394 0.0342 0.3643 0.048 Uiso 1 1 calc R . .
C23 C 0.04294(18) 0.1075(4) 0.34372(13) 0.0355(8) Uani 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
C24 O1 1.424(5) . ?
O1 C21 1.361(5) . ?
C1 C4 1.494(5) . ?
C2 C4 1.518(6) . ?
C3 C4 1.518(7) . ?
C4 C5 1.530(5) . ?
C5 C6 1.350(6) . ?
C5 C10 1.387(5) . ?
C6 C7 1.383(6) . ?
C7 C8 1.355(5) . ?
C8 C9 1.367(5) . ?
C8 C11 1.487(5) . ?
C9 C10 1.379(6) . ?
C11 C12 1.354(5) . ?
C11 C23 1.454(5) . ?
C12 C13 1.423(5) . ?
C13 C17 1.407(5) . ?
C13 C14 1.403(5) . ?
C14 C15 1.368(6) . ?
C15 C015 1.388(6) . ?
C015 C16 1.363(6) . ?
C16 C17 1.405(5) . ?
C17 C18 1.452(5) . ?
C18 C23 1.409(5) . ?
C18 C19 1.414(5) . ?
C19 C20 1.348(6) . ?
C20 C21 1.394(5) . ?
C21 C22 1.365(5) . ?
C22 C23 1.406(5) . ?

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
C21 O1 C24 118.8(3) . . ?
C1 C4 C2 107.7(4) . . ?
C1 C4 C5 112.3(3) . . ?
C2 C4 C5 111.1(4) . . ?
C1 C4 C3 107.4(4) . . ?
C2 C4 C3 109.2(5) . . ?
C5 C4 C3 109.0(3) . . ?
C6 C5 C10 115.3(4) . . ?
C6 C5 C4 122.2(3) . . ?
C10 C5 C4 122.5(3) . . ?
C5 C6 C7 122.7(4) . . ?
C8 C7 C6 122.0(4) . . ?
C7 C8 C9 116.3(4) . . ?
C7 C8 C11 122.1(3) . . ?
C9 C8 C11 121.5(3) . . ?
C8 C9 C10 121.8(4) . . ?
C5 C10 C9 121.9(4) . . ?
C12 C11 C23 118.9(3) . . ?
C12 C11 C8 119.6(3) . . ?
C23 C11 C8 121.5(3) . . ?
C11 C12 C13 123.3(3) . . ?
C17 C13 C14 119.7(3) . . ?
C17 C13 C12 119.2(3) . . ?
C14 C13 C12 121.1(4) . . ?
C15 C14 C13 120.9(4) . . ?
C14 C15 C015 119.6(4) . . ?
C16 C015 C15 120.5(4) . . ?
C015 C16 C17 121.5(4) . . ?
C16 C17 C13 117.7(4) . . ?
C16 C17 C18 123.3(3) . . ?
C13 C17 C18 118.9(3) . . ?
C23 C18 C19 117.6(3) . . ?
C23 C18 C17 120.1(3) . . ?
C19 C18 C17 122.3(3) . . ?
C20 C19 C18 122.0(4) . . ?
C19 C20 C21 120.0(4) . . ?
C22 C21 O1 125.1(4) . . ?
C22 C21 C20 120.3(4) . . ?
O1 C21 C20 114.6(3) . . ?
C21 C22 C23 120.5(3) . . ?
C18 C23 C22 119.6(3) . . ?
C18 C23 C11 119.5(3) . . ?
C22 C23 C11 120.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047


