# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_cd16779
_database_code_depnum_ccdc_archive 'CCDC 1855380'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 O3'
_chemical_formula_weight         292.32

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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6093(12)
_cell_length_b                   14.413(2)
_cell_length_c                   14.072(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.861(3)
_cell_angle_gamma                90
_cell_volume                     1539.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2149
_cell_measurement_theta_min      5.366
_cell_measurement_theta_max      45.050

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8730
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2866
_reflns_number_gt                2052
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0600P)²+0.1964P] 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         2866
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.005

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 0.77318(16) 0.07452(8) 1.00463(8) 0.0625(4) Uani 1 1 d . . . . .
O2 O 0.8632(2) 0.05512(10) 0.70517(10) 0.0865(5) Uani 1 1 d . . . . .
O3 O 0.63433(17) -0.03813(10) 0.71489(8) 0.0702(4) Uani 1 1 d . . . . .
C1 C 0.7794(2) 0.09965(13) 0.91108(12) 0.0562(4) Uani 1 1 d . . . . .
C2 C 0.7556(2) 0.02266(12) 0.85617(12) 0.0529(4) Uani 1 1 d . . . . .
C3 C 0.7312(2) -0.05437(12) 0.91872(12) 0.0542(4) Uani 1 1 d . . . . .
C4 C 0.7445(2) -0.01909(13) 1.00763(12) 0.0581(4) Uani 1 1 d . . . . .
C5 C 0.7384(3) -0.05988(15) 1.10435(13) 0.0743(6) Uani 1 1 d . . . . .
H5A H 0.6328 -0.0402 1.1321 0.111 Uiso 1 1 calc R U . . .
H5B H 0.8391 -0.0395 1.1436 0.111 Uiso 1 1 calc R U . . .
H5C H 0.7395 -0.1263 1.0998 0.111 Uiso 1 1 calc R U . . .
C6 C 0.7089(2) -0.15317(12) 0.89266(11) 0.0551(4) Uani 1 1 d . . . . .
C7 C 0.8222(3) -0.19608(14) 0.83333(13) 0.0673(5) Uani 1 1 d . . . . .
H7 H 0.9110 -0.1616 0.8078 0.081 Uiso 1 1 calc R U . . .
C8 C 0.8054(3) -0.28842(16) 0.81166(15) 0.0822(6) Uani 1 1 d . . . . .
H8 H 0.8833 -0.3163 0.7722 0.099 Uiso 1 1 calc R U . . .
C9 C 0.6741(3) -0.33984(15) 0.84795(16) 0.0834(7) Uani 1 1 d . . . . .
H9 H 0.6628 -0.4026 0.8333 0.100 Uiso 1 1 calc R U . . .
C10 C 0.5600(3) -0.29854(15) 0.90567(15) 0.0785(6) Uani 1 1 d . . . . .
H10 H 0.4699 -0.3331 0.9299 0.094 Uiso 1 1 calc R U . . .
C11 C 0.5776(3) -0.20634(13) 0.92801(13) 0.0675(5) Uani 1 1 d . . . . .
H11 H 0.4994 -0.1791 0.9678 0.081 Uiso 1 1 calc R U . . .
C12 C 0.7598(2) 0.01730(12) 0.75174(13) 0.0562(4) Uani 1 1 d . . . . .
C13 C 0.6395(3) -0.06175(18) 0.61598(13) 0.0875(7) Uani 1 1 d . . . . .
H13A H 0.6433 -0.0060 0.5788 0.131 Uiso 1 1 calc R U . . .
H13B H 0.5361 -0.0967 0.5960 0.131 Uiso 1 1 calc R U . . .
H13C H 0.7424 -0.0984 0.6070 0.131 Uiso 1 1 calc R U . . .
C14 C 0.8007(2) 0.19883(13) 0.89428(13) 0.0584(5) Uani 1 1 d . . . . .
C15 C 0.8779(3) 0.25451(16) 0.96514(16) 0.0808(6) Uani 1 1 d . . . . .
H15 H 0.9167 0.2284 1.0233 0.097 Uiso 1 1 calc R U . . .
C16 C 0.8983(3) 0.34790(17) 0.9509(2) 0.0967(8) Uani 1 1 d . . . . .
H16 H 0.9513 0.3844 0.9992 0.116 Uiso 1 1 calc R U . . .
C17 C 0.8414(3) 0.38739(17) 0.8668(2) 0.0937(8) Uani 1 1 d . . . . .
H17 H 0.8566 0.4507 0.8572 0.112 Uiso 1 1 calc R U . . .
C18 C 0.7619(3) 0.33384(16) 0.79613(18) 0.0900(7) Uani 1 1 d . . . . .
H18 H 0.7215 0.3609 0.7388 0.108 Uiso 1 1 calc R U . . .
C19 C 0.7413(3) 0.24012(15) 0.80957(15) 0.0752(6) Uani 1 1 d . . . . .
H19 H 0.6869 0.2042 0.7612 0.090 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 1.368(2) . ?
O1 C1 1.369(2) . ?
O2 C12 1.190(2) . ?
O3 C12 1.324(2) . ?
O3 C13 1.436(2) . ?
C1 C2 1.357(2) . ?
C1 C14 1.460(3) . ?
C2 C3 1.437(2) . ?
C2 C12 1.474(2) . ?
C3 C4 1.348(2) . ?
C3 C6 1.477(2) . ?
C4 C5 1.486(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C11 1.379(3) . ?
C6 C7 1.386(2) . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.380(3) . ?
C14 C19 1.381(3) . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.358(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 H19 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
C4 O1 C1 107.85(13) . . ?
C12 O3 C13 117.18(15) . . ?
C2 C1 O1 108.61(15) . . ?
C2 C1 C14 136.08(16) . . ?
O1 C1 C14 115.23(15) . . ?
C1 C2 C3 107.50(15) . . ?
C1 C2 C12 126.82(16) . . ?
C3 C2 C12 125.64(16) . . ?
C4 C3 C2 105.81(16) . . ?
C4 C3 C6 126.45(16) . . ?
C2 C3 C6 127.61(15) . . ?
C3 C4 O1 110.22(15) . . ?
C3 C4 C5 134.09(18) . . ?
O1 C4 C5 115.68(16) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 117.71(17) . . ?
C11 C6 C3 121.33(15) . . ?
C7 C6 C3 120.95(16) . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 121.22(18) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
O2 C12 O3 123.17(17) . . ?
O2 C12 C2 125.79(18) . . ?
O3 C12 C2 111.02(15) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.15(19) . . ?
C15 C14 C1 119.92(18) . . ?
C19 C14 C1 121.91(18) . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.8(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?

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
C4 O1 C1 C2 -0.21(18) . . . . ?
C4 O1 C1 C14 177.10(14) . . . . ?
O1 C1 C2 C3 0.67(19) . . . . ?
C14 C1 C2 C3 -175.81(19) . . . . ?
O1 C1 C2 C12 -177.35(16) . . . . ?
C14 C1 C2 C12 6.2(3) . . . . ?
C1 C2 C3 C4 -0.89(19) . . . . ?
C12 C2 C3 C4 177.17(17) . . . . ?
C1 C2 C3 C6 -176.86(16) . . . . ?
C12 C2 C3 C6 1.2(3) . . . . ?
C2 C3 C4 O1 0.77(19) . . . . ?
C6 C3 C4 O1 176.81(15) . . . . ?
C2 C3 C4 C5 -177.7(2) . . . . ?
C6 C3 C4 C5 -1.7(3) . . . . ?
C1 O1 C4 C3 -0.38(19) . . . . ?
C1 O1 C4 C5 178.41(15) . . . . ?
C4 C3 C6 C11 52.0(3) . . . . ?
C2 C3 C6 C11 -132.83(19) . . . . ?
C4 C3 C6 C7 -126.6(2) . . . . ?
C2 C3 C6 C7 48.6(3) . . . . ?
C11 C6 C7 C8 -0.8(3) . . . . ?
C3 C6 C7 C8 177.79(18) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C6 0.4(3) . . . . ?
C7 C6 C11 C10 0.3(3) . . . . ?
C3 C6 C11 C10 -178.33(18) . . . . ?
C13 O3 C12 O2 7.9(3) . . . . ?
C13 O3 C12 C2 -170.39(17) . . . . ?
C1 C2 C12 O2 42.4(3) . . . . ?
C3 C2 C12 O2 -135.3(2) . . . . ?
C1 C2 C12 O3 -139.32(18) . . . . ?
C3 C2 C12 O3 43.0(2) . . . . ?
C2 C1 C14 C15 -159.1(2) . . . . ?
O1 C1 C14 C15 24.6(2) . . . . ?
C2 C1 C14 C19 22.7(3) . . . . ?
O1 C1 C14 C19 -153.65(17) . . . . ?
C19 C14 C15 C16 -1.3(3) . . . . ?
C1 C14 C15 C16 -179.7(2) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
C1 C14 C19 C18 179.44(18) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-4



