# 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_160612c
_database_code_depnum_ccdc_archive 'CCDC 1497561'
_audit_update_record             
;
2016-10-08 deposited with the CCDC.
2016-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 Cl O4'
_chemical_formula_weight         430.86

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8081(4)
_cell_length_b                   9.9881(5)
_cell_length_c                   12.6194(6)
_cell_angle_alpha                79.9048(16)
_cell_angle_beta                 82.4837(16)
_cell_angle_gamma                80.2931(16)
_cell_volume                     1071.49(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6244
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   0.7103
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14454
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3790
_reflns_number_gt                2661
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+0.3525P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3790
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7028(3) 0.3655(3) 0.08078(18) 0.0581(6) Uani 1 1 d . . . . .
H1 H 0.6001 0.4064 0.0912 0.070 Uiso 1 1 calc R U . . .
C2 C 0.7490(4) 0.2888(3) -0.0018(2) 0.0720(8) Uani 1 1 d . . . . .
H2 H 0.6776 0.2768 -0.0462 0.086 Uiso 1 1 calc R U . . .
C3 C 0.9006(4) 0.2303(3) -0.01780(19) 0.0697(7) Uani 1 1 d . . . . .
C4 C 1.0067(3) 0.2459(3) 0.0475(2) 0.0749(8) Uani 1 1 d . . . . .
H4 H 1.1095 0.2058 0.0361 0.090 Uiso 1 1 calc R U . . .
C5 C 0.9592(3) 0.3216(3) 0.1301(2) 0.0617(6) Uani 1 1 d . . . . .
H5 H 1.0310 0.3322 0.1748 0.074 Uiso 1 1 calc R U . . .
C6 C 0.8073(2) 0.3824(2) 0.14825(16) 0.0445(5) Uani 1 1 d . . . . .
C7 C 0.7622(2) 0.4574(2) 0.24109(16) 0.0420(5) Uani 1 1 d . . . . .
C8 C 0.7992(2) 0.4044(2) 0.34936(16) 0.0416(5) Uani 1 1 d . . . . .
C9 C 0.7449(2) 0.5055(2) 0.41108(16) 0.0416(5) Uani 1 1 d . . . . .
C10 C 0.6859(2) 0.5872(2) 0.24430(16) 0.0440(5) Uani 1 1 d . . . . .
C11 C 0.6199(3) 0.6973(2) 0.16265(17) 0.0488(5) Uani 1 1 d . . . . .
C12 C 0.5151(3) 0.8176(2) 0.19872(16) 0.0463(5) Uani 1 1 d . . . . .
C13 C 0.4049(3) 0.8031(2) 0.28702(18) 0.0532(6) Uani 1 1 d . . . . .
H13 H 0.3991 0.7170 0.3282 0.064 Uiso 1 1 calc R U . . .
C14 C 0.3039(3) 0.9157(3) 0.3140(2) 0.0652(7) Uani 1 1 d . . . . .
H14 H 0.2285 0.9048 0.3725 0.078 Uiso 1 1 calc R U . . .
C15 C 0.3134(3) 1.0440(3) 0.2555(2) 0.0718(7) Uani 1 1 d . . . . .
H15 H 0.2464 1.1201 0.2752 0.086 Uiso 1 1 calc R U . . .
C16 C 0.4220(4) 1.0593(2) 0.1678(2) 0.0724(8) Uani 1 1 d . . . . .
H16 H 0.4282 1.1461 0.1278 0.087 Uiso 1 1 calc R U . . .
C17 C 0.5220(3) 0.9473(2) 0.13857(19) 0.0599(6) Uani 1 1 d . . . . .
H17 H 0.5945 0.9585 0.0783 0.072 Uiso 1 1 calc R U . . .
C18 C 0.7373(2) 0.5201(2) 0.52528(16) 0.0422(5) Uani 1 1 d . . . . .
C19 C 0.8469(3) 0.4459(2) 0.59110(17) 0.0508(5) Uani 1 1 d . . . . .
H19 H 0.9273 0.3844 0.5634 0.061 Uiso 1 1 calc R U . . .
C20 C 0.8357(3) 0.4640(3) 0.69890(19) 0.0622(7) Uani 1 1 d . . . . .
H20 H 0.9089 0.4142 0.7432 0.075 Uiso 1 1 calc R U . . .
C21 C 0.7173(3) 0.5548(3) 0.7403(2) 0.0653(7) Uani 1 1 d . . . . .
H21 H 0.7105 0.5659 0.8125 0.078 Uiso 1 1 calc R U . . .
C22 C 0.6094(3) 0.6290(3) 0.67551(19) 0.0617(6) Uani 1 1 d . . . . .
H22 H 0.5293 0.6905 0.7036 0.074 Uiso 1 1 calc R U . . .
C23 C 0.6195(3) 0.6125(2) 0.56843(18) 0.0516(6) Uani 1 1 d . . . . .
H23 H 0.5465 0.6638 0.5246 0.062 Uiso 1 1 calc R U . . .
C24 C 0.8661(3) 0.2604(2) 0.38723(17) 0.0490(5) Uani 1 1 d . . . . .
C25 C 0.8476(4) 0.0287(3) 0.3780(3) 0.0845(9) Uani 1 1 d . . . . .
H25A H 0.9138 0.0015 0.3153 0.101 Uiso 1 1 calc R U . . .
H25B H 0.9080 0.0088 0.4394 0.101 Uiso 1 1 calc R U . . .
C26A C 0.7156(10) -0.0462(7) 0.4005(6) 0.098(2) Uani 0.7 1 d . . P . .
H26A H 0.6558 -0.0245 0.4662 0.148 Uiso 0.7 1 calc R U P . .
H26B H 0.7520 -0.1432 0.4084 0.148 Uiso 0.7 1 calc R U P . .
H26C H 0.6522 -0.0202 0.3417 0.148 Uiso 0.7 1 calc R U P . .
Cl1 Cl 0.95960(15) 0.13318(9) -0.12103(7) 0.1242(4) Uani 1 1 d . . . . .
O1 O 0.67480(16) 0.61745(13) 0.34771(10) 0.0446(4) Uani 1 1 d . . . . .
O2 O 0.6495(2) 0.68773(17) 0.06650(13) 0.0705(5) Uani 1 1 d . . . . .
O3 O 0.9763(2) 0.22451(18) 0.43723(17) 0.0893(7) Uani 1 1 d . . . . .
O4 O 0.78756(19) 0.17538(15) 0.35739(14) 0.0656(5) Uani 1 1 d . . . . .
C26B C 0.762(3) -0.046(2) 0.3380(16) 0.114(7) Uani 0.3 1 d . . P . .


_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 C2 1.380(4) . ?
C1 C6 1.381(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 Cl1 1.733(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.475(3) . ?
C7 C10 1.361(3) . ?
C7 C8 1.435(3) . ?
C8 C9 1.368(3) . ?
C8 C24 1.480(3) . ?
C9 O1 1.361(2) . ?
C9 C18 1.465(3) . ?
C10 O1 1.378(2) . ?
C10 C11 1.468(3) . ?
C11 O2 1.224(3) . ?
C11 C12 1.487(3) . ?
C12 C13 1.383(3) . ?
C12 C17 1.388(3) . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.387(3) . ?
C18 C23 1.389(3) . ?
C19 C20 1.392(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O3 1.197(3) . ?
C24 O4 1.311(3) . ?
C25 C26A 1.457(8) . ?
C25 O4 1.461(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?

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
C2 C1 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 Cl1 119.2(2) . . ?
C2 C3 Cl1 119.8(2) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 118.82(19) . . ?
C1 C6 C7 122.9(2) . . ?
C10 C7 C8 105.78(18) . . ?
C10 C7 C6 129.62(18) . . ?
C8 C7 C6 124.55(18) . . ?
C9 C8 C7 107.45(17) . . ?
C9 C8 C24 127.33(18) . . ?
C7 C8 C24 124.80(19) . . ?
O1 C9 C8 108.95(17) . . ?
O1 C9 C18 114.38(17) . . ?
C8 C9 C18 136.59(18) . . ?
C7 C10 O1 109.91(16) . . ?
C7 C10 C11 133.91(19) . . ?
O1 C10 C11 116.15(18) . . ?
O2 C11 C10 119.7(2) . . ?
O2 C11 C12 121.15(18) . . ?
C10 C11 C12 119.11(19) . . ?
C13 C12 C17 118.9(2) . . ?
C13 C12 C11 121.87(19) . . ?
C17 C12 C11 119.1(2) . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C19 C18 C23 119.0(2) . . ?
C19 C18 C9 121.6(2) . . ?
C23 C18 C9 119.40(18) . . ?
C18 C19 C20 119.6(2) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.9(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 120.9(2) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
O3 C24 O4 124.0(2) . . ?
O3 C24 C8 125.8(2) . . ?
O4 C24 C8 110.16(18) . . ?
C26A C25 O4 107.7(4) . . ?
C26A C25 H25A 110.2 . . ?
O4 C25 H25A 110.2 . . ?
C26A C25 H25B 110.2 . . ?
O4 C25 H25B 110.2 . . ?
H25A C25 H25B 108.5 . . ?
C25 C26A H26A 109.5 . . ?
C25 C26A H26B 109.5 . . ?
H26A C26A H26B 109.5 . . ?
C25 C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C9 O1 C10 107.90(15) . . ?
C24 O4 C25 117.5(2) . . ?

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 -0.9(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 Cl1 179.8(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
Cl1 C3 C4 C5 -179.2(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 177.4(2) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -176.8(2) . . . . ?
C5 C6 C7 C10 128.3(3) . . . . ?
C1 C6 C7 C10 -54.3(3) . . . . ?
C5 C6 C7 C8 -48.9(3) . . . . ?
C1 C6 C7 C8 128.5(2) . . . . ?
C10 C7 C8 C9 -0.7(2) . . . . ?
C6 C7 C8 C9 177.04(19) . . . . ?
C10 C7 C8 C24 172.3(2) . . . . ?
C6 C7 C8 C24 -10.0(3) . . . . ?
C7 C8 C9 O1 0.7(2) . . . . ?
C24 C8 C9 O1 -172.07(19) . . . . ?
C7 C8 C9 C18 177.1(2) . . . . ?
C24 C8 C9 C18 4.4(4) . . . . ?
C8 C7 C10 O1 0.4(2) . . . . ?
C6 C7 C10 O1 -177.14(19) . . . . ?
C8 C7 C10 C11 178.5(2) . . . . ?
C6 C7 C10 C11 1.0(4) . . . . ?
C7 C10 C11 O2 -11.2(4) . . . . ?
O1 C10 C11 O2 166.8(2) . . . . ?
C7 C10 C11 C12 167.5(2) . . . . ?
O1 C10 C11 C12 -14.5(3) . . . . ?
O2 C11 C12 C13 138.0(2) . . . . ?
C10 C11 C12 C13 -40.6(3) . . . . ?
O2 C11 C12 C17 -38.2(3) . . . . ?
C10 C11 C12 C17 143.1(2) . . . . ?
C17 C12 C13 C14 0.2(3) . . . . ?
C11 C12 C13 C14 -176.1(2) . . . . ?
C12 C13 C14 C15 -1.5(4) . . . . ?
C13 C14 C15 C16 1.6(4) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C12 -0.9(4) . . . . ?
C13 C12 C17 C16 1.0(3) . . . . ?
C11 C12 C17 C16 177.4(2) . . . . ?
O1 C9 C18 C19 -154.56(18) . . . . ?
C8 C9 C18 C19 29.1(4) . . . . ?
O1 C9 C18 C23 24.1(3) . . . . ?
C8 C9 C18 C23 -152.2(2) . . . . ?
C23 C18 C19 C20 0.8(3) . . . . ?
C9 C18 C19 C20 179.45(19) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C18 0.7(3) . . . . ?
C19 C18 C23 C22 -1.1(3) . . . . ?
C9 C18 C23 C22 -179.76(19) . . . . ?
C9 C8 C24 O3 -57.8(4) . . . . ?
C7 C8 C24 O3 130.7(3) . . . . ?
C9 C8 C24 O4 122.7(2) . . . . ?
C7 C8 C24 O4 -48.9(3) . . . . ?
C8 C9 O1 C10 -0.4(2) . . . . ?
C18 C9 O1 C10 -177.75(16) . . . . ?
C7 C10 O1 C9 0.0(2) . . . . ?
C11 C10 O1 C9 -178.50(17) . . . . ?
O3 C24 O4 C25 -5.9(4) . . . . ?
C8 C24 O4 C25 173.6(2) . . . . ?
C26A C25 O4 C24 147.1(4) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_150916b-14_a
_database_code_depnum_ccdc_archive 'CCDC 1497563'
_audit_update_record             
;
2016-10-08 deposited with the CCDC.
2016-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 O4'
_chemical_formula_weight         398.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   8.5852(6)
_cell_length_b                   15.9050(12)
_cell_length_c                   15.6721(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.176(2)
_cell_angle_gamma                90
_cell_volume                     2131.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    6336
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   0.6929
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15870
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.875
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3759
_reflns_number_gt                2729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.6546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3759
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22660(17) 0.43383(11) 0.17192(9) 0.0731(5) Uani 1 1 d . . . . .
O2 O 0.1601(2) 0.30252(10) 0.31018(12) 0.0828(5) Uani 1 1 d . . . . .
O3 O 0.51891(17) 0.55110(9) 0.40692(9) 0.0609(4) Uani 1 1 d . . . . .
O4 O 0.46834(16) 0.59081(8) 0.26980(8) 0.0562(4) Uani 1 1 d . . . . .
C1 C 0.3396(2) 0.47250(11) 0.31074(11) 0.0410(4) Uani 1 1 d . . . . .
C2 C 0.2982(2) 0.41329(11) 0.38275(12) 0.0454(4) Uani 1 1 d . . . . .
H2 H 0.3490 0.4251 0.4400 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1811(2) 0.47659(12) 0.34710(12) 0.0454(5) Uani 1 1 d . . . . .
H3 H 0.0963 0.4519 0.3091 0.055 Uiso 1 1 calc R U . . .
C4 C 0.3448(2) 0.44053(12) 0.22008(12) 0.0468(5) Uani 1 1 d . . . . .
C5 C 0.5012(2) 0.41987(11) 0.19146(11) 0.0458(4) Uani 1 1 d . . . . .
C6 C 0.5205(3) 0.42223(14) 0.10424(13) 0.0633(6) Uani 1 1 d . . . . .
H6 H 0.4355 0.4340 0.0650 0.076 Uiso 1 1 calc R U . . .
C7 C 0.6650(3) 0.40722(16) 0.07618(16) 0.0802(7) Uani 1 1 d . . . . .
H7 H 0.6778 0.4097 0.0179 0.096 Uiso 1 1 calc R U . . .
C8 C 0.7907(3) 0.38856(16) 0.13369(19) 0.0807(8) Uani 1 1 d . . . . .
H8 H 0.8883 0.3789 0.1143 0.097 Uiso 1 1 calc R U . . .
C9 C 0.7726(3) 0.38415(15) 0.21924(16) 0.0680(6) Uani 1 1 d . . . . .
H9 H 0.8573 0.3701 0.2579 0.082 Uiso 1 1 calc R U . . .
C10 C 0.6281(2) 0.40053(12) 0.24853(13) 0.0539(5) Uani 1 1 d . . . . .
H10 H 0.6166 0.3985 0.3069 0.065 Uiso 1 1 calc R U . . .
C11 C 0.2697(2) 0.32213(12) 0.36101(13) 0.0521(5) Uani 1 1 d . . . . .
C12 C 0.3781(2) 0.25710(12) 0.40068(11) 0.0453(4) Uani 1 1 d . . . . .
C13 C 0.4962(2) 0.27433(13) 0.46482(13) 0.0573(5) Uani 1 1 d . . . . .
H13 H 0.5116 0.3292 0.4843 0.069 Uiso 1 1 calc R U . . .
C14 C 0.5909(3) 0.21064(15) 0.49986(15) 0.0664(6) Uani 1 1 d . . . . .
H14 H 0.6688 0.2227 0.5433 0.080 Uiso 1 1 calc R U . . .
C15 C 0.5707(3) 0.12984(15) 0.47101(14) 0.0633(6) Uani 1 1 d . . . . .
H15 H 0.6351 0.0872 0.4946 0.076 Uiso 1 1 calc R U . . .
C16 C 0.4552(3) 0.11171(13) 0.40726(14) 0.0627(6) Uani 1 1 d . . . . .
H16 H 0.4424 0.0568 0.3874 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3584(2) 0.17407(12) 0.37249(13) 0.0547(5) Uani 1 1 d . . . . .
H17 H 0.2794 0.1610 0.3300 0.066 Uiso 1 1 calc R U . . .
C18 C 0.1310(2) 0.55110(12) 0.39554(12) 0.0457(4) Uani 1 1 d . . . . .
C19 C 0.1600(3) 0.55942(14) 0.48296(13) 0.0607(6) Uani 1 1 d . . . . .
H19 H 0.2173 0.5185 0.5145 0.073 Uiso 1 1 calc R U . . .
C20 C 0.1036(3) 0.62902(15) 0.52406(14) 0.0693(6) Uani 1 1 d . . . . .
H20 H 0.1238 0.6341 0.5831 0.083 Uiso 1 1 calc R U . . .
C21 C 0.0193(3) 0.68990(14) 0.47963(15) 0.0666(6) Uani 1 1 d . . . . .
H21 H -0.0181 0.7359 0.5081 0.080 Uiso 1 1 calc R U . . .
C22 C -0.0096(3) 0.68269(15) 0.39296(16) 0.0739(7) Uani 1 1 d . . . . .
H22 H -0.0658 0.7243 0.3619 0.089 Uiso 1 1 calc R U . . .
C23 C 0.0452(3) 0.61300(14) 0.35114(14) 0.0646(6) Uani 1 1 d . . . . .
H23 H 0.0236 0.6080 0.2921 0.077 Uiso 1 1 calc R U . . .
C24 C 0.4526(2) 0.54116(11) 0.33680(12) 0.0413(4) Uani 1 1 d . . . . .
C25 C 0.5864(3) 0.65698(15) 0.27850(15) 0.0708(6) Uani 1 1 d . . . . .
H25A H 0.6647 0.6440 0.3252 0.085 Uiso 1 1 calc R U . . .
H25B H 0.5383 0.7103 0.2907 0.085 Uiso 1 1 calc R U . . .
C26 C 0.6593(4) 0.66206(19) 0.19730(19) 0.0974(9) Uani 1 1 d . . . . .
H26A H 0.7124 0.6102 0.1877 0.146 Uiso 1 1 calc R U . . .
H26B H 0.7332 0.7075 0.2001 0.146 Uiso 1 1 calc R U . . .
H26C H 0.5801 0.6717 0.1511 0.146 Uiso 1 1 calc R 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
O1 C4 1.214(2) . ?
O2 C11 1.217(2) . ?
O3 C24 1.201(2) . ?
O4 C24 1.330(2) . ?
O4 C25 1.459(2) . ?
C1 C24 1.493(2) . ?
C1 C4 1.514(2) . ?
C1 C3 1.524(2) . ?
C1 C2 1.536(2) . ?
C2 C3 1.495(3) . ?
C2 C11 1.504(3) . ?
C2 H2 0.9800 . ?
C3 C18 1.491(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.490(3) . ?
C5 C10 1.381(3) . ?
C5 C6 1.392(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.365(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.489(3) . ?
C12 C13 1.389(3) . ?
C12 C17 1.398(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 C23 1.380(3) . ?
C19 C20 1.390(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.362(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.363(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 C26 1.470(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C24 O4 C25 118.26(15) . . ?
C24 C1 C4 115.41(15) . . ?
C24 C1 C3 116.54(15) . . ?
C4 C1 C3 117.94(15) . . ?
C24 C1 C2 115.80(14) . . ?
C4 C1 C2 120.80(15) . . ?
C3 C1 C2 58.50(12) . . ?
C3 C2 C11 118.32(16) . . ?
C3 C2 C1 60.33(12) . . ?
C11 C2 C1 117.92(15) . . ?
C3 C2 H2 116.2 . . ?
C11 C2 H2 116.2 . . ?
C1 C2 H2 116.2 . . ?
C18 C3 C2 124.06(16) . . ?
C18 C3 C1 122.18(15) . . ?
C2 C3 C1 61.17(12) . . ?
C18 C3 H3 113.3 . . ?
C2 C3 H3 113.3 . . ?
C1 C3 H3 113.3 . . ?
O1 C4 C5 121.28(17) . . ?
O1 C4 C1 121.30(17) . . ?
C5 C4 C1 117.41(15) . . ?
C10 C5 C6 119.05(19) . . ?
C10 C5 C4 122.28(17) . . ?
C6 C5 C4 118.65(17) . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 120.3(2) . . ?
C5 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
O2 C11 C12 120.82(18) . . ?
O2 C11 C2 119.69(18) . . ?
C12 C11 C2 119.48(17) . . ?
C13 C12 C17 118.35(18) . . ?
C13 C12 C11 123.57(18) . . ?
C17 C12 C11 118.08(17) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.30(19) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C19 C18 C23 118.28(19) . . ?
C19 C18 C3 123.25(18) . . ?
C23 C18 C3 118.40(18) . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 121.4(2) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 119.4(2) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C23 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 121.3(2) . . ?
C18 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
O3 C24 O4 124.78(17) . . ?
O3 C24 C1 126.08(17) . . ?
O4 C24 C1 109.14(15) . . ?
O4 C25 C26 107.8(2) . . ?
O4 C25 H25A 110.2 . . ?
C26 C25 H25A 110.2 . . ?
O4 C25 H25B 110.2 . . ?
C26 C25 H25B 110.2 . . ?
H25A C25 H25B 108.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
C24 C1 C2 C3 106.60(17) . . . . ?
C4 C1 C2 C3 -105.92(18) . . . . ?
C24 C1 C2 C11 -144.97(17) . . . . ?
C4 C1 C2 C11 2.5(2) . . . . ?
C3 C1 C2 C11 108.42(19) . . . . ?
C11 C2 C3 C18 141.02(18) . . . . ?
C1 C2 C3 C18 -111.21(19) . . . . ?
C11 C2 C3 C1 -107.77(18) . . . . ?
C24 C1 C3 C18 8.8(2) . . . . ?
C4 C1 C3 C18 -135.08(18) . . . . ?
C2 C1 C3 C18 114.1(2) . . . . ?
C24 C1 C3 C2 -105.34(17) . . . . ?
C4 C1 C3 C2 110.79(18) . . . . ?
C24 C1 C4 O1 -130.2(2) . . . . ?
C3 C1 C4 O1 14.1(3) . . . . ?
C2 C1 C4 O1 82.2(2) . . . . ?
C24 C1 C4 C5 48.2(2) . . . . ?
C3 C1 C4 C5 -167.56(16) . . . . ?
C2 C1 C4 C5 -99.4(2) . . . . ?
O1 C4 C5 C10 -158.6(2) . . . . ?
C1 C4 C5 C10 23.0(3) . . . . ?
O1 C4 C5 C6 23.0(3) . . . . ?
C1 C4 C5 C6 -155.37(18) . . . . ?
C10 C5 C6 C7 -1.4(3) . . . . ?
C4 C5 C6 C7 177.1(2) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C6 C7 C8 C9 0.5(4) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C6 C5 C10 C9 0.3(3) . . . . ?
C4 C5 C10 C9 -178.08(19) . . . . ?
C8 C9 C10 C5 1.2(3) . . . . ?
C3 C2 C11 O2 5.7(3) . . . . ?
C1 C2 C11 O2 -63.8(3) . . . . ?
C3 C2 C11 C12 -175.57(16) . . . . ?
C1 C2 C11 C12 114.96(19) . . . . ?
O2 C11 C12 C13 -173.8(2) . . . . ?
C2 C11 C12 C13 7.5(3) . . . . ?
O2 C11 C12 C17 5.3(3) . . . . ?
C2 C11 C12 C17 -173.40(17) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C11 C12 C13 C14 178.9(2) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C12 1.1(3) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
C11 C12 C17 C16 -179.84(19) . . . . ?
C2 C3 C18 C19 -15.0(3) . . . . ?
C1 C3 C18 C19 -89.7(2) . . . . ?
C2 C3 C18 C23 168.07(18) . . . . ?
C1 C3 C18 C23 93.3(2) . . . . ?
C23 C18 C19 C20 -0.2(3) . . . . ?
C3 C18 C19 C20 -177.15(19) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C22 -0.4(4) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C19 C18 C23 C22 0.7(3) . . . . ?
C3 C18 C23 C22 177.8(2) . . . . ?
C21 C22 C23 C18 -1.0(4) . . . . ?
C25 O4 C24 O3 6.9(3) . . . . ?
C25 O4 C24 C1 -173.49(17) . . . . ?
C4 C1 C24 O3 -145.07(19) . . . . ?
C3 C1 C24 O3 70.2(2) . . . . ?
C2 C1 C24 O3 4.2(3) . . . . ?
C4 C1 C24 O4 35.4(2) . . . . ?
C3 C1 C24 O4 -109.42(17) . . . . ?
C2 C1 C24 O4 -175.39(14) . . . . ?
C24 O4 C25 C26 141.1(2) . . . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.038



