# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20150611_m146_0ma
_database_code_depnum_ccdc_archive 'CCDC 1520693'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 O4'
_chemical_formula_weight         384.41

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)/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                   11.9761(3)
_cell_length_b                   15.4866(4)
_cell_length_c                   11.0055(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.1670(10)
_cell_angle_gamma                90.00
_cell_volume                     1960.46(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4136
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      20.97

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6978
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25539
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         28.24
_reflns_number_total             4789
_reflns_number_gt                2845
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0683P)²+0.0222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4789
_refine_ls_number_parameters     263
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.046
_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
C25 C 0.6385(2) 0.13482(16) -0.1893(2) 0.1210(9) Uani 1 1 d U . .
H25A H 0.6664 0.0873 -0.1329 0.181 Uiso 1 1 calc R . .
H25B H 0.6997 0.1552 -0.2227 0.181 Uiso 1 1 calc R . .
H25C H 0.5740 0.1161 -0.2574 0.181 Uiso 1 1 calc R . .
O4 O 0.60222(10) 0.20259(9) -0.12228(12) 0.0926(4) Uani 1 1 d U . .
C21 C 0.49611(13) 0.24977(11) 0.01264(14) 0.0658(4) Uani 1 1 d U . .
H21 H 0.5379 0.3011 0.0216 0.079 Uiso 1 1 calc R . .
C20 C 0.41296(12) 0.23844(9) 0.07609(13) 0.0567(4) Uani 1 1 d U . .
H20 H 0.3998 0.2823 0.1281 0.068 Uiso 1 1 calc R . .
C24 C 0.37041(13) 0.09931(10) -0.01544(14) 0.0611(4) Uani 1 1 d U . .
H24 H 0.3276 0.0484 -0.0268 0.073 Uiso 1 1 calc R . .
C23 C 0.45484(14) 0.11017(11) -0.07824(15) 0.0688(4) Uani 1 1 d U . .
H23 H 0.4689 0.0664 -0.1300 0.083 Uiso 1 1 calc R . .
O2 O 0.10764(8) 0.08795(5) 0.19059(8) 0.0513(3) Uani 1 1 d U . .
O3 O 0.16202(9) 0.01922(6) 0.03896(10) 0.0661(3) Uani 1 1 d U . .
O1 O 0.33150(11) 0.05890(8) 0.39805(12) 0.0887(4) Uani 1 1 d U . .
C14 C 0.04589(14) 0.30284(10) 0.30542(15) 0.0656(4) Uani 1 1 d U . .
H14 H 0.1058 0.3090 0.3797 0.079 Uiso 1 1 calc R . .
C15 C -0.03879(16) 0.36590(11) 0.27247(18) 0.0777(5) Uani 1 1 d U . .
H15 H -0.0366 0.4132 0.3251 0.093 Uiso 1 1 calc R . .
C16 C -0.12522(16) 0.35849(12) 0.16291(19) 0.0803(5) Uani 1 1 d U . .
H16 H -0.1824 0.4008 0.1402 0.096 Uiso 1 1 calc R . .
C17 C -0.12796(16) 0.28894(14) 0.08630(18) 0.0900(6) Uani 1 1 d U . .
H17 H -0.1864 0.2847 0.0105 0.108 Uiso 1 1 calc R . .
C18 C -0.04446(14) 0.22413(12) 0.11990(15) 0.0725(5) Uani 1 1 d U . .
H18 H -0.0481 0.1763 0.0678 0.087 Uiso 1 1 calc R . .
C22 C 0.51754(12) 0.18498(11) -0.06435(14) 0.0644(4) Uani 1 1 d U . .
C19 C 0.34805(11) 0.16247(9) 0.06395(12) 0.0461(3) Uani 1 1 d U . .
C11 C 0.26154(11) 0.15082(8) 0.13403(12) 0.0446(3) Uani 1 1 d U . .
C10 C 0.24356(10) 0.19724(8) 0.22900(12) 0.0458(3) Uani 1 1 d U . .
H10 H 0.2889 0.2440 0.2663 0.055 Uiso 1 1 calc R . .
C9 C 0.14127(11) 0.16448(8) 0.26783(12) 0.0462(3) Uani 1 1 d U . .
C8 C 0.16218(12) 0.13572(9) 0.40513(12) 0.0522(3) Uani 1 1 d U . .
H8A H 0.1804 0.1864 0.4588 0.063 Uiso 1 1 calc R . .
H8B H 0.0904 0.1117 0.4148 0.063 Uiso 1 1 calc R . .
C7 C 0.25798(12) 0.06996(9) 0.45253(13) 0.0534(4) Uani 1 1 d U . .
C6 C 0.26037(13) 0.01873(8) 0.56750(12) 0.0522(4) Uani 1 1 d U . .
C5 C 0.35345(14) -0.03759(10) 0.61356(15) 0.0660(4) Uani 1 1 d U . .
H5 H 0.4140 -0.0395 0.5760 0.079 Uiso 1 1 calc R . .
C4 C 0.35538(18) -0.09041(11) 0.71496(17) 0.0833(6) Uani 1 1 d U . .
H4 H 0.4172 -0.1283 0.7451 0.100 Uiso 1 1 calc R . .
C3 C 0.2669(2) -0.08763(13) 0.77190(17) 0.0889(6) Uani 1 1 d U . .
H3 H 0.2688 -0.1240 0.8397 0.107 Uiso 1 1 calc R . .
C12 C 0.17634(12) 0.07870(9) 0.11150(13) 0.0487(3) Uani 1 1 d U . .
C2 C 0.17623(18) -0.03179(12) 0.72954(16) 0.0818(5) Uani 1 1 d U . .
H2 H 0.1168 -0.0297 0.7688 0.098 Uiso 1 1 calc R . .
C1 C 0.17315(15) 0.02175(10) 0.62768(14) 0.0662(4) Uani 1 1 d U . .
H1 H 0.1117 0.0602 0.5994 0.079 Uiso 1 1 calc R . .
C13 C 0.04359(11) 0.23126(9) 0.23089(12) 0.0478(3) Uani 1 1 d U . .


_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
C25 O4 1.418(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
O4 C22 1.3672(17) . ?
C21 C20 1.377(2) . ?
C21 C22 1.383(2) . ?
C21 H21 0.9300 . ?
C20 C19 1.3958(19) . ?
C20 H20 0.9300 . ?
C24 C23 1.385(2) . ?
C24 C19 1.3864(19) . ?
C24 H24 0.9300 . ?
C23 C22 1.366(2) . ?
C23 H23 0.9300 . ?
O2 C12 1.3617(16) . ?
O2 C9 1.4488(15) . ?
O3 C12 1.1996(15) . ?
O1 C7 1.2075(16) . ?
C14 C13 1.375(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.358(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(2) . ?
C17 H17 0.9300 . ?
C18 C13 1.378(2) . ?
C18 H18 0.9300 . ?
C19 C11 1.4649(17) . ?
C11 C10 1.3344(17) . ?
C11 C12 1.4862(18) . ?
C10 C9 1.4941(18) . ?
C10 H10 0.9300 . ?
C9 C8 1.5276(18) . ?
C9 C13 1.5292(18) . ?
C8 C7 1.5141(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 C6 1.4870(19) . ?
C6 C1 1.385(2) . ?
C6 C5 1.395(2) . ?
C5 C4 1.379(2) . ?
C5 H5 0.9300 . ?
C4 C3 1.374(3) . ?
C4 H4 0.9300 . ?
C3 C2 1.365(3) . ?
C3 H3 0.9300 . ?
C2 C1 1.387(2) . ?
C2 H2 0.9300 . ?
C1 H1 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
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 O4 C25 117.97(16) . . ?
C20 C21 C22 120.14(15) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C20 C19 121.39(14) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C23 C24 C19 121.66(15) . . ?
C23 C24 H24 119.2 . . ?
C19 C24 H24 119.2 . . ?
C22 C23 C24 120.15(15) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C12 O2 C9 110.02(10) . . ?
C13 C14 C15 121.47(15) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 119.72(17) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 119.83(15) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.92(17) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C13 C18 C17 119.56(17) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C23 C22 O4 124.97(16) . . ?
C23 C22 C21 119.60(14) . . ?
O4 C22 C21 115.43(15) . . ?
C24 C19 C20 117.05(13) . . ?
C24 C19 C11 122.27(12) . . ?
C20 C19 C11 120.67(12) . . ?
C10 C11 C19 129.64(12) . . ?
C10 C11 C12 106.41(11) . . ?
C19 C11 C12 123.92(11) . . ?
C11 C10 C9 111.41(11) . . ?
C11 C10 H10 124.3 . . ?
C9 C10 H10 124.3 . . ?
O2 C9 C10 103.06(10) . . ?
O2 C9 C8 106.50(10) . . ?
C10 C9 C8 117.40(11) . . ?
O2 C9 C13 109.28(10) . . ?
C10 C9 C13 108.77(10) . . ?
C8 C9 C13 111.27(10) . . ?
C7 C8 C9 115.90(11) . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C9 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
O1 C7 C6 120.20(12) . . ?
O1 C7 C8 120.78(13) . . ?
C6 C7 C8 119.03(13) . . ?
C1 C6 C5 118.71(14) . . ?
C1 C6 C7 123.41(13) . . ?
C5 C6 C7 117.83(14) . . ?
C4 C5 C6 119.79(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C3 C4 C5 120.63(17) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C2 C3 C4 120.36(17) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O3 C12 O2 120.41(12) . . ?
O3 C12 C11 130.73(13) . . ?
O2 C12 C11 108.86(11) . . ?
C3 C2 C1 119.64(18) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C6 C1 C2 120.84(15) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C14 C13 C18 118.48(13) . . ?
C14 C13 C9 119.99(12) . . ?
C18 C13 C9 121.43(13) . . ?

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
C22 C21 C20 C19 -0.5(2) . . . . ?
C19 C24 C23 C22 -0.9(2) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C16 C17 C18 C13 -1.4(3) . . . . ?
C24 C23 C22 O4 -179.64(13) . . . . ?
C24 C23 C22 C21 -0.1(2) . . . . ?
C25 O4 C22 C23 -8.3(2) . . . . ?
C25 O4 C22 C21 172.08(16) . . . . ?
C20 C21 C22 C23 0.8(2) . . . . ?
C20 C21 C22 O4 -179.61(13) . . . . ?
C23 C24 C19 C20 1.2(2) . . . . ?
C23 C24 C19 C11 -178.07(13) . . . . ?
C21 C20 C19 C24 -0.5(2) . . . . ?
C21 C20 C19 C11 178.80(12) . . . . ?
C24 C19 C11 C10 167.07(14) . . . . ?
C20 C19 C11 C10 -12.1(2) . . . . ?
C24 C19 C11 C12 -10.8(2) . . . . ?
C20 C19 C11 C12 169.96(12) . . . . ?
C19 C11 C10 C9 177.10(12) . . . . ?
C12 C11 C10 C9 -4.73(14) . . . . ?
C12 O2 C9 C10 -2.87(12) . . . . ?
C12 O2 C9 C8 -127.03(11) . . . . ?
C12 O2 C9 C13 112.67(11) . . . . ?
C11 C10 C9 O2 4.83(13) . . . . ?
C11 C10 C9 C8 121.49(12) . . . . ?
C11 C10 C9 C13 -111.07(12) . . . . ?
O2 C9 C8 C7 61.47(14) . . . . ?
C10 C9 C8 C7 -53.31(16) . . . . ?
C13 C9 C8 C7 -179.53(11) . . . . ?
C9 C8 C7 O1 18.7(2) . . . . ?
C9 C8 C7 C6 -161.14(12) . . . . ?
O1 C7 C6 C1 -173.52(15) . . . . ?
C8 C7 C6 C1 6.4(2) . . . . ?
O1 C7 C6 C5 3.9(2) . . . . ?
C8 C7 C6 C5 -176.18(13) . . . . ?
C1 C6 C5 C4 1.8(2) . . . . ?
C7 C6 C5 C4 -175.82(14) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C9 O2 C12 O3 -179.62(12) . . . . ?
C9 O2 C12 C11 0.25(13) . . . . ?
C10 C11 C12 O3 -177.31(14) . . . . ?
C19 C11 C12 O3 1.0(2) . . . . ?
C10 C11 C12 O2 2.84(14) . . . . ?
C19 C11 C12 O2 -178.86(10) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C5 C6 C1 C2 -1.8(2) . . . . ?
C7 C6 C1 C2 175.62(14) . . . . ?
C3 C2 C1 C6 0.6(3) . . . . ?
C15 C14 C13 C18 1.3(2) . . . . ?
C15 C14 C13 C9 177.71(14) . . . . ?
C17 C18 C13 C14 0.1(2) . . . . ?
C17 C18 C13 C9 -176.29(14) . . . . ?
O2 C9 C13 C14 168.41(12) . . . . ?
C10 C9 C13 C14 -79.76(15) . . . . ?
C8 C9 C13 C14 51.08(16) . . . . ?
O2 C9 C13 C18 -15.30(18) . . . . ?
C10 C9 C13 C18 96.53(15) . . . . ?
C8 C9 C13 C18 -132.63(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.031
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
