# 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_dbr15_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 1561066'
_audit_update_record             
;
2017-07-09 deposited with the CCDC.
2017-11-07 downloaded from the CCDC.
;
_audit_creation_date             2017-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2012-9
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H16 O2'
_chemical_formula_sum            'C20 H16 O2'
_chemical_formula_weight         288.33
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.732(5)
_cell_length_b                   9.388(5)
_cell_length_c                   14.303(5)
_cell_angle_alpha                92.462(5)
_cell_angle_beta                 94.667(5)
_cell_angle_gamma                104.905(5)
_cell_volume                     739.7(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2610
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2478
_diffrn_reflns_av_unetI/netI     0.1527
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15956
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.586
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1836
_reflns_number_total             3399
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.116(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0752
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.2168
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.1973(4) 1.1561(2) 0.42800(14) 0.0615(6) Uani 1 1 d . . . . .
O2 O 0.5953(4) 0.6577(2) 0.36444(15) 0.0695(7) Uani 1 1 d . . . . .
C1 C 0.7832(4) 1.2888(3) 0.25022(16) 0.0359(6) Uani 1 1 d . . . . .
C2 C 0.8185(5) 1.4348(3) 0.2271(2) 0.0514(7) Uani 1 1 d . . . . .
H2 H 0.7193 1.4904 0.2493 0.062 Uiso 1 1 calc R . . . .
C3 C 0.9979(6) 1.4983(3) 0.1718(2) 0.0617(9) Uani 1 1 d . . . . .
H3 H 1.0183 1.5959 0.1568 0.074 Uiso 1 1 calc R . . . .
C4 C 1.1458(5) 1.4187(3) 0.1389(2) 0.0551(8) Uani 1 1 d . . . . .
H4 H 1.2674 1.4621 0.1019 0.066 Uiso 1 1 calc R . . . .
C5 C 1.1149(5) 1.2737(3) 0.16064(19) 0.0476(7) Uani 1 1 d . . . . .
H5 H 1.2150 1.2191 0.1380 0.057 Uiso 1 1 calc R . . . .
C6 C 0.9354(4) 1.2099(3) 0.21606(18) 0.0418(7) Uani 1 1 d . . . . .
H6 H 0.9161 1.1122 0.2307 0.050 Uiso 1 1 calc R . . . .
C7 C 0.5900(4) 1.2294(3) 0.31004(16) 0.0390(6) Uani 1 1 d . . . . .
H7 H 0.5161 1.2993 0.3330 0.047 Uiso 1 1 calc R . . . .
C8 C 0.5000(4) 1.0935(3) 0.33790(16) 0.0362(6) Uani 1 1 d . . . . .
C9 C 0.2981(5) 1.0654(3) 0.39876(17) 0.0419(7) Uani 1 1 d . . . . .
C10 C 0.2453(5) 0.9093(3) 0.41883(18) 0.0469(7) Uani 1 1 d . . . . .
H10 H 0.1244 0.8623 0.4551 0.056 Uiso 1 1 calc R . . . .
C11 C 0.3950(4) 0.8441(3) 0.37780(16) 0.0387(7) Uani 1 1 d . . . . .
C12 C 0.5612(4) 0.9480(3) 0.31777(15) 0.0343(6) Uani 1 1 d . . . . .
H12 H 0.7310 0.9571 0.3401 0.041 Uiso 1 1 calc R . . . .
C13 C 0.5136(4) 0.8905(3) 0.21429(16) 0.0335(6) Uani 1 1 d . . . . .
C14 C 0.3236(4) 0.9166(3) 0.15792(17) 0.0415(7) Uani 1 1 d . . . . .
H14 H 0.2248 0.9700 0.1831 0.050 Uiso 1 1 calc R . . . .
C15 C 0.2784(5) 0.8645(3) 0.06466(18) 0.0492(8) Uani 1 1 d . . . . .
H15 H 0.1501 0.8833 0.0275 0.059 Uiso 1 1 calc R . . . .
C16 C 0.4215(5) 0.7856(3) 0.02681(19) 0.0543(8) Uani 1 1 d . . . . .
H16 H 0.3903 0.7505 -0.0360 0.065 Uiso 1 1 calc R . . . .
C17 C 0.6096(5) 0.7582(3) 0.0808(2) 0.0524(8) Uani 1 1 d . . . . .
H17 H 0.7067 0.7044 0.0550 0.063 Uiso 1 1 calc R . . . .
C18 C 0.6570(5) 0.8110(3) 0.17505(18) 0.0448(7) Uani 1 1 d . . . . .
H18 H 0.7862 0.7924 0.2116 0.054 Uiso 1 1 calc R . . . .
C19 C 0.4198(6) 0.6922(3) 0.39020(18) 0.0495(7) Uani 1 1 d . . . . .
C20 C 0.2282(6) 0.5871(4) 0.4373(2) 0.0716(10) Uani 1 1 d . . . . .
H20A H 0.2453 0.4886 0.4279 0.107 Uiso 1 1 calc GR . . . .
H20B H 0.0707 0.5909 0.4108 0.107 Uiso 1 1 calc GR . . . .
H20C H 0.2459 0.6148 0.5034 0.107 Uiso 1 1 calc GR . . . .


_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 C9 1.223(3) . ?
O2 C19 1.212(3) . ?
C1 C2 1.392(4) . ?
C1 C6 1.385(4) . ?
C1 C7 1.465(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.363(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.380(3) . ?
C7 C8 1.338(4) . ?
C8 C9 1.481(3) . ?
C8 C12 1.517(4) . ?
C9 C10 1.464(4) . ?
C10 C11 1.333(4) . ?
C11 C12 1.524(3) . ?
C11 C19 1.486(4) . ?
C12 C13 1.532(3) . ?
C13 C14 1.381(3) . ?
C13 C18 1.379(4) . ?
C14 C15 1.381(4) . ?
C15 C16 1.366(4) . ?
C16 C17 1.359(4) . ?
C17 C18 1.396(4) . ?
C19 C20 1.501(4) . ?

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 C7 117.9(2) . . ?
C6 C1 C2 117.7(2) . . ?
C6 C1 C7 124.4(2) . . ?
C3 C2 C1 121.1(3) . . ?
C4 C3 C2 120.3(3) . . ?
C3 C4 C5 119.9(3) . . ?
C4 C5 C6 119.9(3) . . ?
C5 C6 C1 121.1(2) . . ?
C8 C7 C1 132.1(2) . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 C12 132.2(2) . . ?
C9 C8 C12 107.7(2) . . ?
O1 C9 C8 126.4(3) . . ?
O1 C9 C10 126.5(2) . . ?
C10 C9 C8 107.1(2) . . ?
C11 C10 C9 110.4(2) . . ?
C10 C11 C12 112.2(2) . . ?
C10 C11 C19 127.0(2) . . ?
C19 C11 C12 120.7(2) . . ?
C8 C12 C11 102.36(19) . . ?
C8 C12 C13 114.50(19) . . ?
C11 C12 C13 110.61(19) . . ?
C14 C13 C12 120.4(2) . . ?
C18 C13 C12 121.3(2) . . ?
C18 C13 C14 118.3(2) . . ?
C15 C14 C13 120.9(3) . . ?
C16 C15 C14 120.2(3) . . ?
C17 C16 C15 120.1(3) . . ?
C16 C17 C18 120.1(3) . . ?
C13 C18 C17 120.5(3) . . ?
O2 C19 C11 119.6(2) . . ?
O2 C19 C20 122.0(3) . . ?
C11 C19 C20 118.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
