# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_5hc7
_database_code_depnum_ccdc_archive 'CCDC 1456377'
_audit_update_record             
;
2016-02-27 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-(2-methoxyphenyl)benzo[de]chromene-2,6-dione
_chemical_name_common            
3-(2-methoxyphenyl)benzo[de]chromene-2,6-dione
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 O4'
_chemical_formula_weight         304.29

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      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                   8.4472(4)
_cell_length_b                   12.7834(5)
_cell_length_c                   15.0002(6)
_cell_angle_alpha                100.217(2)
_cell_angle_beta                 105.699(2)
_cell_angle_gamma                108.9389(19)
_cell_volume                     1411.00(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4755
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.33

_exptl_crystal_description       Square
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            20230
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.474
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4954
_reflns_number_gt                3545
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0367P)²+1.4698P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0039(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4954
_refine_ls_number_parameters     418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 -0.0945(4) 0.4818(2) 0.1400(2) 0.0419(7) Uani 1 1 d . . . . .
H1 H -0.2040 0.4703 0.1475 0.050 Uiso 1 1 calc R U . . .
C2 C -0.0321(4) 0.3943(2) 0.1349(2) 0.0455(7) Uani 1 1 d . . . . .
H2 H -0.1008 0.3228 0.1385 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1319(4) 0.4121(2) 0.1245(2) 0.0452(7) Uani 1 1 d . . . . .
H3 H 0.1731 0.3529 0.1220 0.054 Uiso 1 1 calc R U . . .
C4 C 0.2347(4) 0.5174(2) 0.11785(18) 0.0353(6) Uani 1 1 d . . . . .
C5 C 0.4100(4) 0.5381(2) 0.1073(2) 0.0434(7) Uani 1 1 d . . . . .
C6 C 0.5013(4) 0.6490(2) 0.0935(2) 0.0462(7) Uani 1 1 d . . . . .
H6 H 0.6078 0.6623 0.0818 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4382(4) 0.7321(2) 0.09688(19) 0.0393(6) Uani 1 1 d . . . . .
H7 H 0.5031 0.8016 0.0886 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2720(3) 0.7177(2) 0.11298(17) 0.0315(6) Uani 1 1 d . . . . .
C9 C 0.2067(3) 0.8014(2) 0.11894(18) 0.0323(6) Uani 1 1 d . . . . .
C10 C 0.0368(4) 0.7799(2) 0.13519(19) 0.0372(6) Uani 1 1 d . . . . .
C11 C 0.0093(3) 0.5866(2) 0.13358(18) 0.0335(6) Uani 1 1 d . . . . .
C12 C 0.1724(3) 0.6070(2) 0.12181(17) 0.0308(6) Uani 1 1 d . . . . .
C13 C 0.2998(4) 0.9192(2) 0.11285(19) 0.0355(6) Uani 1 1 d . . . . .
C14 C 0.4561(4) 0.9971(2) 0.1858(2) 0.0449(7) Uani 1 1 d . . . . .
H14 H 0.5072 0.9741 0.2380 0.054 Uiso 1 1 calc R U . . .
C15 C 0.5375(4) 1.1083(3) 0.1825(2) 0.0561(8) Uani 1 1 d . . . . .
H15 H 0.6424 1.1600 0.2322 0.067 Uiso 1 1 calc R U . . .
C16 C 0.4622(5) 1.1421(3) 0.1052(3) 0.0602(9) Uani 1 1 d . . . . .
H16 H 0.5154 1.2176 0.1037 0.072 Uiso 1 1 calc R U . . .
C17 C 0.3096(4) 1.0661(3) 0.0304(2) 0.0548(8) Uani 1 1 d . . . . .
H17 H 0.2609 1.0895 -0.0221 0.066 Uiso 1 1 calc R U . . .
C18 C 0.2283(4) 0.9541(2) 0.0336(2) 0.0397(7) Uani 1 1 d . . . . .
C19 C 0.0155(5) 0.8930(3) -0.1268(2) 0.0583(9) Uani 1 1 d . . . . .
H19A H -0.0115 0.9606 -0.1171 0.088 Uiso 1 1 calc R U . . .
H19B H -0.0902 0.8277 -0.1696 0.088 Uiso 1 1 calc R U . . .
H19C H 0.1072 0.9050 -0.1547 0.088 Uiso 1 1 calc R U . . .
C20 C 0.3761(3) 0.5043(2) 0.37057(18) 0.0336(6) Uani 1 1 d . . . . .
C21 C 0.2655(4) 0.3989(2) 0.3731(2) 0.0407(7) Uani 1 1 d . . . . .
H21 H 0.1503 0.3863 0.3724 0.049 Uiso 1 1 calc R U . . .
C22 C 0.3297(4) 0.3127(2) 0.3766(2) 0.0470(7) Uani 1 1 d . . . . .
H22 H 0.2572 0.2415 0.3788 0.056 Uiso 1 1 calc R U . . .
C23 C 0.5003(4) 0.3307(2) 0.3769(2) 0.0459(7) Uani 1 1 d . . . . .
H23 H 0.5414 0.2716 0.3789 0.055 Uiso 1 1 calc R U . . .
C24 C 0.6096(4) 0.4360(2) 0.37410(19) 0.0381(6) Uani 1 1 d . . . . .
C25 C 0.7937(4) 0.4575(3) 0.3764(2) 0.0516(8) Uani 1 1 d . . . . .
C26 C 0.9038(4) 0.5756(3) 0.3811(2) 0.0541(8) Uani 1 1 d . . . . .
H26 H 1.0213 0.5924 0.3845 0.065 Uiso 1 1 calc R U . . .
C27 C 0.8430(4) 0.6593(2) 0.3809(2) 0.0442(7) Uani 1 1 d . . . . .
H27 H 0.9198 0.7325 0.3847 0.053 Uiso 1 1 calc R U . . .
C28 C 0.6608(3) 0.6405(2) 0.37481(18) 0.0325(6) Uani 1 1 d . . . . .
C29 C 0.5946(3) 0.7246(2) 0.37535(18) 0.0328(6) Uani 1 1 d . . . . .
C30 C 0.4066(3) 0.6963(2) 0.36520(19) 0.0355(6) Uani 1 1 d . . . . .
C31 C 0.5478(3) 0.5258(2) 0.37139(17) 0.0317(6) Uani 1 1 d . . . . .
C32 C 0.6997(3) 0.8469(2) 0.38449(18) 0.0335(6) Uani 1 1 d . . . . .
C33 C 0.7159(3) 0.9348(2) 0.46154(19) 0.0356(6) Uani 1 1 d . . . . .
C34 C 0.7984(4) 1.0497(2) 0.4670(2) 0.0450(7) Uani 1 1 d . . . . .
H34 H 0.8028 1.1076 0.5161 0.054 Uiso 1 1 calc R U . . .
C35 C 0.8744(4) 1.0782(3) 0.3992(2) 0.0533(8) Uani 1 1 d . . . . .
H35 H 0.9297 1.1555 0.4027 0.064 Uiso 1 1 calc R U . . .
C36 C 0.8688(4) 0.9933(3) 0.3266(2) 0.0513(8) Uani 1 1 d . . . . .
H36 H 0.9246 1.0131 0.2829 0.062 Uiso 1 1 calc R U . . .
C37 C 0.7801(4) 0.8782(2) 0.3187(2) 0.0432(7) Uani 1 1 d . . . . .
H37 H 0.7743 0.8210 0.2686 0.052 Uiso 1 1 calc R U . . .
C38 C 0.6729(5) 0.9823(3) 0.6119(2) 0.0555(8) Uani 1 1 d . . . . .
H38A H 0.7982 1.0293 0.6440 0.083 Uiso 1 1 calc R U . . .
H38B H 0.6276 0.9443 0.6549 0.083 Uiso 1 1 calc R U . . .
H38C H 0.6102 1.0302 0.5937 0.083 Uiso 1 1 calc R U . . .
O1 O -0.0566(2) 0.67191(15) 0.13930(14) 0.0407(5) Uani 1 1 d . . . . .
O2 O -0.0285(3) 0.84991(17) 0.14636(16) 0.0534(6) Uani 1 1 d . . . . .
O3 O 0.0761(3) 0.87169(16) -0.03611(14) 0.0517(6) Uani 1 1 d . . . . .
O4 O 0.4764(3) 0.46579(19) 0.11076(18) 0.0667(7) Uani 1 1 d . . . . .
O5 O 0.3080(2) 0.58812(15) 0.36736(14) 0.0406(5) Uani 1 1 d . . . . .
O6 O 0.3277(3) 0.75898(16) 0.35327(16) 0.0507(5) Uani 1 1 d . . . . .
O7 O 0.6475(3) 0.89809(15) 0.52775(14) 0.0453(5) Uani 1 1 d . . . . .
O8 O 0.8525(3) 0.3817(2) 0.3749(2) 0.0796(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
C1 C11 1.379(4) . ?
C1 C2 1.382(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C12 1.405(3) . ?
C4 C5 1.475(4) . ?
C5 O4 1.229(3) . ?
C5 C6 1.459(4) . ?
C6 C7 1.334(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.447(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.354(3) . ?
C8 C12 1.442(3) . ?
C9 C10 1.467(4) . ?
C9 C13 1.488(3) . ?
C10 O2 1.204(3) . ?
C10 O1 1.371(3) . ?
C11 O1 1.376(3) . ?
C11 C12 1.383(4) . ?
C13 C14 1.382(4) . ?
C13 C18 1.397(4) . ?
C14 C15 1.381(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C18 O3 1.363(3) . ?
C19 O3 1.425(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O5 1.373(3) . ?
C20 C31 1.382(3) . ?
C20 C21 1.382(4) . ?
C21 C22 1.380(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(4) . ?
C23 H23 0.9300 . ?
C24 C31 1.410(3) . ?
C24 C25 1.478(4) . ?
C25 O8 1.223(3) . ?
C25 C26 1.471(4) . ?
C26 C27 1.329(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.454(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.362(3) . ?
C28 C31 1.450(3) . ?
C29 C30 1.468(4) . ?
C29 C32 1.487(3) . ?
C30 O6 1.205(3) . ?
C30 O5 1.374(3) . ?
C32 C37 1.385(4) . ?
C32 C33 1.404(4) . ?
C33 O7 1.357(3) . ?
C33 C34 1.382(4) . ?
C34 C35 1.383(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.373(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.384(4) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 O7 1.421(3) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 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
C11 C1 C2 118.5(3) . . ?
C11 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C12 119.7(2) . . ?
C3 C4 C5 121.2(2) . . ?
C12 C4 C5 119.1(2) . . ?
O4 C5 C6 121.7(3) . . ?
O4 C5 C4 121.6(3) . . ?
C6 C5 C4 116.7(2) . . ?
C7 C6 C5 122.6(3) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C8 122.2(3) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C12 119.5(2) . . ?
C9 C8 C7 123.4(2) . . ?
C12 C8 C7 117.0(2) . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 C13 124.0(2) . . ?
C10 C9 C13 115.8(2) . . ?
O2 C10 O1 116.3(2) . . ?
O2 C10 C9 125.4(2) . . ?
O1 C10 C9 118.2(2) . . ?
O1 C11 C1 116.9(2) . . ?
O1 C11 C12 120.5(2) . . ?
C1 C11 C12 122.5(2) . . ?
C11 C12 C4 118.2(2) . . ?
C11 C12 C8 119.7(2) . . ?
C4 C12 C8 122.2(2) . . ?
C14 C13 C18 118.6(2) . . ?
C14 C13 C9 121.0(2) . . ?
C18 C13 C9 120.3(2) . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.5(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
O3 C18 C17 124.6(3) . . ?
O3 C18 C13 115.0(2) . . ?
C17 C18 C13 120.4(3) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 C31 120.8(2) . . ?
O5 C20 C21 117.0(2) . . ?
C31 C20 C21 122.2(2) . . ?
C22 C21 C20 118.6(3) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C31 120.0(3) . . ?
C23 C24 C25 120.9(3) . . ?
C31 C24 C25 119.1(2) . . ?
O8 C25 C26 121.5(3) . . ?
O8 C25 C24 122.1(3) . . ?
C26 C25 C24 116.4(2) . . ?
C27 C26 C25 123.0(3) . . ?
C27 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
C26 C27 C28 122.3(3) . . ?
C26 C27 H27 118.9 . . ?
C28 C27 H27 118.9 . . ?
C29 C28 C31 119.4(2) . . ?
C29 C28 C27 123.8(2) . . ?
C31 C28 C27 116.7(2) . . ?
C28 C29 C30 119.9(2) . . ?
C28 C29 C32 124.6(2) . . ?
C30 C29 C32 115.5(2) . . ?
O6 C30 O5 116.0(2) . . ?
O6 C30 C29 125.9(2) . . ?
O5 C30 C29 118.2(2) . . ?
C20 C31 C24 118.1(2) . . ?
C20 C31 C28 119.4(2) . . ?
C24 C31 C28 122.4(2) . . ?
C37 C32 C33 118.4(2) . . ?
C37 C32 C29 122.6(2) . . ?
C33 C32 C29 119.0(2) . . ?
O7 C33 C34 124.3(2) . . ?
O7 C33 C32 115.3(2) . . ?
C34 C33 C32 120.4(3) . . ?
C33 C34 C35 119.7(3) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 120.5(3) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 119.8(3) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C36 C37 C32 121.0(3) . . ?
C36 C37 H37 119.5 . . ?
C32 C37 H37 119.5 . . ?
O7 C38 H38A 109.5 . . ?
O7 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O7 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C10 O1 C11 121.8(2) . . ?
C18 O3 C19 118.0(2) . . ?
C20 O5 C30 121.9(2) . . ?
C33 O7 C38 118.3(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
C11 C1 C2 C3 0.6(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C12 0.1(4) . . . . ?
C2 C3 C4 C5 179.7(3) . . . . ?
C3 C4 C5 O4 -5.1(4) . . . . ?
C12 C4 C5 O4 174.5(3) . . . . ?
C3 C4 C5 C6 175.5(3) . . . . ?
C12 C4 C5 C6 -5.0(4) . . . . ?
O4 C5 C6 C7 -174.7(3) . . . . ?
C4 C5 C6 C7 4.7(4) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C9 178.5(3) . . . . ?
C6 C7 C8 C12 -2.2(4) . . . . ?
C12 C8 C9 C10 0.6(4) . . . . ?
C7 C8 C9 C10 179.9(2) . . . . ?
C12 C8 C9 C13 178.7(2) . . . . ?
C7 C8 C9 C13 -2.0(4) . . . . ?
C8 C9 C10 O2 176.1(3) . . . . ?
C13 C9 C10 O2 -2.2(4) . . . . ?
C8 C9 C10 O1 -3.1(4) . . . . ?
C13 C9 C10 O1 178.6(2) . . . . ?
C2 C1 C11 O1 -179.7(2) . . . . ?
C2 C1 C11 C12 0.4(4) . . . . ?
O1 C11 C12 C4 179.1(2) . . . . ?
C1 C11 C12 C4 -1.0(4) . . . . ?
O1 C11 C12 C8 -1.6(4) . . . . ?
C1 C11 C12 C8 178.3(2) . . . . ?
C3 C4 C12 C11 0.8(4) . . . . ?
C5 C4 C12 C11 -178.8(2) . . . . ?
C3 C4 C12 C8 -178.5(2) . . . . ?
C5 C4 C12 C8 1.9(4) . . . . ?
C9 C8 C12 C11 1.8(4) . . . . ?
C7 C8 C12 C11 -177.6(2) . . . . ?
C9 C8 C12 C4 -178.9(2) . . . . ?
C7 C8 C12 C4 1.7(4) . . . . ?
C8 C9 C13 C14 -68.9(3) . . . . ?
C10 C9 C13 C14 109.3(3) . . . . ?
C8 C9 C13 C18 112.4(3) . . . . ?
C10 C9 C13 C18 -69.4(3) . . . . ?
C18 C13 C14 C15 2.1(4) . . . . ?
C9 C13 C14 C15 -176.7(3) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C17 -1.5(5) . . . . ?
C15 C16 C17 C18 1.1(5) . . . . ?
C16 C17 C18 O3 179.5(3) . . . . ?
C16 C17 C18 C13 0.8(5) . . . . ?
C14 C13 C18 O3 178.8(2) . . . . ?
C9 C13 C18 O3 -2.5(4) . . . . ?
C14 C13 C18 C17 -2.4(4) . . . . ?
C9 C13 C18 C17 176.4(3) . . . . ?
O5 C20 C21 C22 -179.8(2) . . . . ?
C31 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C23 C24 C31 0.3(4) . . . . ?
C22 C23 C24 C25 178.7(3) . . . . ?
C23 C24 C25 O8 4.6(5) . . . . ?
C31 C24 C25 O8 -177.0(3) . . . . ?
C23 C24 C25 C26 -175.2(3) . . . . ?
C31 C24 C25 C26 3.2(4) . . . . ?
O8 C25 C26 C27 178.5(3) . . . . ?
C24 C25 C26 C27 -1.7(5) . . . . ?
C25 C26 C27 C28 -0.7(5) . . . . ?
C26 C27 C28 C29 179.3(3) . . . . ?
C26 C27 C28 C31 1.5(4) . . . . ?
C31 C28 C29 C30 -4.5(4) . . . . ?
C27 C28 C29 C30 177.7(2) . . . . ?
C31 C28 C29 C32 176.3(2) . . . . ?
C27 C28 C29 C32 -1.5(4) . . . . ?
C28 C29 C30 O6 -170.7(3) . . . . ?
C32 C29 C30 O6 8.5(4) . . . . ?
C28 C29 C30 O5 7.9(4) . . . . ?
C32 C29 C30 O5 -172.8(2) . . . . ?
O5 C20 C31 C24 -179.6(2) . . . . ?
C21 C20 C31 C24 0.5(4) . . . . ?
O5 C20 C31 C28 3.8(4) . . . . ?
C21 C20 C31 C28 -176.1(2) . . . . ?
C23 C24 C31 C20 -0.7(4) . . . . ?
C25 C24 C31 C20 -179.1(2) . . . . ?
C23 C24 C31 C28 175.9(3) . . . . ?
C25 C24 C31 C28 -2.6(4) . . . . ?
C29 C28 C31 C20 -1.2(4) . . . . ?
C27 C28 C31 C20 176.7(2) . . . . ?
C29 C28 C31 C24 -177.7(2) . . . . ?
C27 C28 C31 C24 0.2(4) . . . . ?
C28 C29 C32 C37 59.6(4) . . . . ?
C30 C29 C32 C37 -119.6(3) . . . . ?
C28 C29 C32 C33 -121.7(3) . . . . ?
C30 C29 C32 C33 59.1(3) . . . . ?
C37 C32 C33 O7 -174.6(2) . . . . ?
C29 C32 C33 O7 6.7(4) . . . . ?
C37 C32 C33 C34 4.8(4) . . . . ?
C29 C32 C33 C34 -174.0(2) . . . . ?
O7 C33 C34 C35 175.7(3) . . . . ?
C32 C33 C34 C35 -3.6(4) . . . . ?
C33 C34 C35 C36 -0.2(5) . . . . ?
C34 C35 C36 C37 2.7(5) . . . . ?
C35 C36 C37 C32 -1.5(4) . . . . ?
C33 C32 C37 C36 -2.2(4) . . . . ?
C29 C32 C37 C36 176.5(3) . . . . ?
O2 C10 O1 C11 -175.9(2) . . . . ?
C9 C10 O1 C11 3.4(4) . . . . ?
C1 C11 O1 C10 179.0(2) . . . . ?
C12 C11 O1 C10 -1.1(4) . . . . ?
C17 C18 O3 C19 13.2(4) . . . . ?
C13 C18 O3 C19 -168.0(2) . . . . ?
C31 C20 O5 C30 -0.2(4) . . . . ?
C21 C20 O5 C30 179.7(2) . . . . ?
O6 C30 O5 C20 173.3(2) . . . . ?
C29 C30 O5 C20 -5.5(3) . . . . ?
C34 C33 O7 C38 -4.7(4) . . . . ?
C32 C33 O7 C38 174.6(2) . . . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Acetonitrile
####################################################################### 
# 
# 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 1465059'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1-phenylnaphtho[2,1-b]furan-2,5-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18.25 H10.50 O3'
_chemical_formula_weight         277.77

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   P21/n

loop_
_symmetry_equiv_pos_as_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                   9.0810(4)
_cell_length_b                   15.7891(7)
_cell_length_c                   9.2543(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.431(2)
_cell_angle_gamma                90.00
_cell_volume                     1315.74(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6434
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.10

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9019
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23545
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         28.70
_reflns_number_total             3406
_reflns_number_gt                2339
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'

_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)+(0.0497P)²+0.2321P] 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     SHELXL
_refine_ls_extinction_coef       0.0073(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3406
_refine_ls_number_parameters     321
_refine_ls_number_restraints     268
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.84816(14) 0.33888(9) 0.30407(13) 0.0430(3) Uani 1 1 d D . .
C13 C 0.69264(14) 0.33419(8) 0.23754(13) 0.0425(3) Uani 1 1 d . . .
C14 C 0.65044(18) 0.36717(10) 0.10000(15) 0.0592(4) Uani 1 1 d . . .
H14 H 0.7206 0.3931 0.0499 0.071 Uiso 1 1 calc R A .
C15 C 0.5048(2) 0.36171(12) 0.03699(18) 0.0713(5) Uani 1 1 d . . .
H15 H 0.4765 0.3850 -0.0547 0.086 Uiso 1 1 calc R . .
C16 C 0.40116(18) 0.32200(11) 0.1090(2) 0.0676(5) Uani 1 1 d . . .
H16 H 0.3029 0.3187 0.0662 0.081 Uiso 1 1 calc R A .
C17 C 0.44225(16) 0.28737(10) 0.24337(19) 0.0599(4) Uani 1 1 d . . .
H17 H 0.3722 0.2597 0.2912 0.072 Uiso 1 1 calc R . .
C18 C 0.58717(14) 0.29331(9) 0.30826(15) 0.0481(3) Uani 1 1 d . . .
H18 H 0.6145 0.2698 0.4000 0.058 Uiso 1 1 calc R A .
O1 O 1.0987(5) 0.3108(4) 0.3071(5) 0.0586(9) Uani 0.75 1 d PDU A 1
O2 O 1.2321(5) 0.4268(6) 0.7744(6) 0.0897(13) Uani 0.75 1 d PDU A 1
O3 O 0.9602(8) 0.2723(4) 0.1038(6) 0.0786(11) Uani 0.75 1 d PDU A 1
C1 C 0.9130(4) 0.3672(6) 0.4349(5) 0.0387(10) Uani 0.75 1 d PDU A 1
C2 C 0.8683(6) 0.4102(5) 0.5620(7) 0.0412(9) Uani 0.75 1 d PDU A 1
C3 C 0.7213(6) 0.4334(6) 0.5695(8) 0.0522(12) Uani 0.75 1 d PDU A 1
H3 H 0.6482 0.4219 0.4920 0.063 Uiso 0.75 1 calc PR A 1
C4 C 0.6851(4) 0.4735(4) 0.6922(5) 0.0606(10) Uani 0.75 1 d PDU A 1
H4 H 0.5868 0.4879 0.6984 0.073 Uiso 0.75 1 calc PR A 1
C5 C 0.7937(4) 0.4923(3) 0.8060(4) 0.0626(10) Uani 0.75 1 d PDU A 1
H5 H 0.7689 0.5195 0.8887 0.075 Uiso 0.75 1 calc PR A 1
C6 C 0.9396(4) 0.4707(4) 0.7963(5) 0.0613(9) Uani 0.75 1 d PDU A 1
H6 H 1.0126 0.4842 0.8728 0.074 Uiso 0.75 1 calc PR A 1
C7 C 0.9792(4) 0.4291(4) 0.6750(5) 0.0468(7) Uani 0.75 1 d PDU A 1
C8 C 1.1389(4) 0.4077(4) 0.6714(5) 0.0537(8) Uani 0.75 1 d PDU A 1
C9 C 1.1778(3) 0.3666(4) 0.5425(4) 0.0514(7) Uani 0.75 1 d PDU A 1
H9 H 1.2760 0.3526 0.5351 0.062 Uiso 0.75 1 calc PR A 1
C10 C 1.0709(3) 0.3490(4) 0.4341(4) 0.0420(7) Uani 0.75 1 d PDU A 1
C11 C 0.9632(3) 0.3033(5) 0.2209(6) 0.0549(9) Uani 0.75 1 d PDU A 1
O1' O 1.1074(19) 0.3231(13) 0.3353(17) 0.062(3) Uani 0.25 1 d PDU A 2
O2' O 1.1886(16) 0.4314(17) 0.8079(17) 0.098(4) Uani 0.25 1 d PDU A 2
O3' O 0.971(3) 0.3003(12) 0.1076(19) 0.094(5) Uani 0.25 1 d PDU A 2
C1' C 0.9212(15) 0.365(2) 0.4346(16) 0.052(4) Uani 0.25 1 d PDU A 2
C2' C 0.849(2) 0.4036(18) 0.551(2) 0.054(3) Uani 0.25 1 d PDU A 2
C3' C 0.700(2) 0.4220(19) 0.557(3) 0.060(3) Uani 0.25 1 d PDU A 2
H3' H 0.6330 0.4043 0.4778 0.072 Uiso 0.25 1 calc PR A 2
C4' C 0.6398(17) 0.4630(12) 0.6664(18) 0.071(3) Uani 0.25 1 d PDU A 2
H4' H 0.5388 0.4751 0.6580 0.086 Uiso 0.25 1 calc PR A 2
C5' C 0.7336(13) 0.4858(10) 0.7883(18) 0.071(3) Uani 0.25 1 d PDU A 2
H5' H 0.6944 0.5133 0.8636 0.086 Uiso 0.25 1 calc PR A 2
C6' C 0.8830(13) 0.4694(11) 0.8034(16) 0.065(3) Uani 0.25 1 d PDU A 2
H6' H 0.9447 0.4834 0.8882 0.078 Uiso 0.25 1 calc PR A 2
C7' C 0.9388(14) 0.4308(15) 0.6865(19) 0.060(3) Uani 0.25 1 d PDU A 2
C8' C 1.0998(13) 0.4154(12) 0.6986(16) 0.063(3) Uani 0.25 1 d PDU A 2
C9' C 1.1711(10) 0.3766(12) 0.5847(13) 0.064(3) Uani 0.25 1 d PDU A 2
C10' C 1.0820(14) 0.3559(15) 0.4668(16) 0.063(3) Uani 0.25 1 d PDU A 2
C11' C 0.9818(13) 0.3162(17) 0.235(2) 0.0549(9) Uani 0.25 1 d PDU A 2
C19' C 1.3405(5) 0.3720(4) 0.6103(6) 0.0489(13) Uani 0.25 1 d PD A 2
H19A H 1.3715 0.3143 0.6016 0.073 Uiso 0.25 1 calc PR A 2
H19B H 1.3755 0.3926 0.7062 0.073 Uiso 0.25 1 calc PR A 2
H19C H 1.3809 0.4061 0.5391 0.073 Uiso 0.25 1 calc PR A 2


_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
C12 C1 1.352(3) . ?
C12 C1' 1.363(8) . ?
C12 C13 1.4677(17) . ?
C12 C11 1.486(3) . ?
C12 C11' 1.489(8) . ?
C13 C14 1.3827(19) . ?
C13 C18 1.3872(18) . ?
C14 C15 1.378(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
O1 C10 1.374(3) . ?
O1 C11 1.382(3) . ?
O2 C8 1.228(3) . ?
O3 C11 1.186(3) . ?
C1 C2 1.461(3) . ?
C1 C10 1.463(3) . ?
C2 C7 1.387(7) . ?
C2 C3 1.394(3) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.494(4) . ?
C8 C9 1.442(4) . ?
C9 C10 1.332(3) . ?
C9 H9 0.9300 . ?
O1' C10' 1.369(8) . ?
O1' C11' 1.381(8) . ?
O2' C8' 1.235(8) . ?
O3' C11' 1.192(8) . ?
C1' C10' 1.459(8) . ?
C1' C2' 1.463(8) . ?
C2' C3' 1.397(8) . ?
C2' C7' 1.47(2) . ?
C3' C4' 1.373(8) . ?
C3' H3' 0.9300 . ?
C4' C5' 1.371(8) . ?
C4' H4' 0.9300 . ?
C5' C6' 1.371(9) . ?
C5' H5' 0.9300 . ?
C6' C7' 1.393(9) . ?
C6' H6' 0.9300 . ?
C7' C8' 1.472(9) . ?
C8' C9' 1.443(9) . ?
C9' C10' 1.313(8) . ?
C9' C19' 1.528(9) . ?
C19' H19A 0.9600 . ?
C19' H19B 0.9600 . ?
C19' H19C 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
C1 C12 C1' 3.6(9) . . ?
C1 C12 C13 132.57(18) . . ?
C1' C12 C13 135.9(6) . . ?
C1 C12 C11 109.6(2) . . ?
C1' C12 C11 106.1(6) . . ?
C13 C12 C11 117.81(18) . . ?
C1 C12 C11' 100.5(6) . . ?
C1' C12 C11' 97.2(9) . . ?
C13 C12 C11' 126.9(6) . . ?
C11 C12 C11' 10.9(9) . . ?
C14 C13 C18 118.91(13) . . ?
C14 C13 C12 120.28(12) . . ?
C18 C13 C12 120.74(11) . . ?
C15 C14 C13 120.18(15) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.27(15) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.08(14) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.20(15) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.33(14) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C10 O1 C11 106.4(4) . . ?
C12 C1 C2 137.8(4) . . ?
C12 C1 C10 104.1(3) . . ?
C2 C1 C10 118.0(3) . . ?
C7 C2 C3 120.8(4) . . ?
C7 C2 C1 117.2(4) . . ?
C3 C2 C1 122.0(5) . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C6 118.2(3) . . ?
C2 C7 C8 123.2(3) . . ?
C6 C7 C8 118.6(3) . . ?
O2 C8 C9 122.3(3) . . ?
O2 C8 C7 120.1(4) . . ?
C9 C8 C7 117.6(3) . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 O1 122.6(3) . . ?
C9 C10 C1 125.1(3) . . ?
O1 C10 C1 112.3(3) . . ?
O3 C11 O1 118.4(4) . . ?
O3 C11 C12 134.0(5) . . ?
O1 C11 C12 107.6(3) . . ?
C10' O1' C11' 114.3(13) . . ?
C12 C1' C10' 120.8(9) . . ?
C12 C1' C2' 124.3(13) . . ?
C10' C1' C2' 114.8(12) . . ?
C3' C2' C1' 130.3(17) . . ?
C3' C2' C7' 109.7(13) . . ?
C1' C2' C7' 120.0(15) . . ?
C4' C3' C2' 127.5(17) . . ?
C4' C3' H3' 116.3 . . ?
C2' C3' H3' 116.3 . . ?
C5' C4' C3' 117.9(16) . . ?
C5' C4' H4' 121.1 . . ?
C3' C4' H4' 121.1 . . ?
C4' C5' C6' 122.4(13) . . ?
C4' C5' H5' 118.8 . . ?
C6' C5' H5' 118.8 . . ?
C5' C6' C7' 117.3(11) . . ?
C5' C6' H6' 121.4 . . ?
C7' C6' H6' 121.4 . . ?
C6' C7' C2' 125.1(11) . . ?
C6' C7' C8' 118.0(11) . . ?
C2' C7' C8' 116.8(12) . . ?
O2' C8' C9' 112.2(11) . . ?
O2' C8' C7' 124.4(12) . . ?
C9' C8' C7' 123.4(10) . . ?
C10' C9' C8' 115.2(11) . . ?
C10' C9' C19' 128.1(9) . . ?
C8' C9' C19' 116.5(7) . . ?
C9' C10' O1' 132.6(12) . . ?
C9' C10' C1' 129.7(11) . . ?
O1' C10' C1' 97.7(10) . . ?
O3' C11' O1' 129.6(15) . . ?
O3' C11' C12 120.5(16) . . ?
O1' C11' C12 109.7(12) . . ?
C9' C19' H19A 109.5 . . ?
C9' C19' H19B 109.5 . . ?
H19A C19' H19B 109.5 . . ?
C9' C19' H19C 109.5 . . ?
H19A C19' H19C 109.5 . . ?
H19B C19' H19C 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
C1 C12 C13 C14 128.4(6) . . . . ?
C1' C12 C13 C14 130(2) . . . . ?
C11 C12 C13 C14 -54.8(4) . . . . ?
C11' C12 C13 C14 -47.6(14) . . . . ?
C1 C12 C13 C18 -54.6(6) . . . . ?
C1' C12 C13 C18 -53(2) . . . . ?
C11 C12 C13 C18 122.2(4) . . . . ?
C11' C12 C13 C18 129.4(14) . . . . ?
C18 C13 C14 C15 2.1(2) . . . . ?
C12 C13 C14 C15 179.15(14) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 1.0(2) . . . . ?
C16 C17 C18 C13 -0.2(2) . . . . ?
C14 C13 C18 C17 -1.3(2) . . . . ?
C12 C13 C18 C17 -178.36(13) . . . . ?
C1' C12 C1 C2 -167(31) . . . . ?
C13 C12 C1 C2 -5.8(16) . . . . ?
C11 C12 C1 C2 177.3(12) . . . . ?
C11' C12 C1 C2 171.0(16) . . . . ?
C1' C12 C1 C10 16(29) . . . . ?
C13 C12 C1 C10 176.8(3) . . . . ?
C11 C12 C1 C10 -0.2(8) . . . . ?
C11' C12 C1 C10 -6.4(13) . . . . ?
C12 C1 C2 C7 -178.5(10) . . . . ?
C10 C1 C2 C7 -1.3(13) . . . . ?
C12 C1 C2 C3 0.0(18) . . . . ?
C10 C1 C2 C3 177.1(8) . . . . ?
C7 C2 C3 C4 -1.9(11) . . . . ?
C1 C2 C3 C4 179.7(9) . . . . ?
C2 C3 C4 C5 1.5(10) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C5 C6 C7 -0.8(7) . . . . ?
C3 C2 C7 C6 0.9(11) . . . . ?
C1 C2 C7 C6 179.4(7) . . . . ?
C3 C2 C7 C8 -178.5(7) . . . . ?
C1 C2 C7 C8 0.0(11) . . . . ?
C5 C6 C7 C2 0.4(8) . . . . ?
C5 C6 C7 C8 179.9(5) . . . . ?
C2 C7 C8 O2 179.4(8) . . . . ?
C6 C7 C8 O2 0.0(9) . . . . ?
C2 C7 C8 C9 1.0(9) . . . . ?
C6 C7 C8 C9 -178.4(5) . . . . ?
O2 C8 C9 C10 -178.9(7) . . . . ?
C7 C8 C9 C10 -0.6(8) . . . . ?
C8 C9 C10 O1 179.3(6) . . . . ?
C8 C9 C10 C1 -0.8(10) . . . . ?
C11 O1 C10 C9 -179.5(6) . . . . ?
C11 O1 C10 C1 0.5(8) . . . . ?
C12 C1 C10 C9 179.8(6) . . . . ?
C2 C1 C10 C9 1.8(13) . . . . ?
C12 C1 C10 O1 -0.2(9) . . . . ?
C2 C1 C10 O1 -178.3(8) . . . . ?
C10 O1 C11 O3 179.4(7) . . . . ?
C10 O1 C11 C12 -0.6(7) . . . . ?
C1 C12 C11 O3 -179.5(9) . . . . ?
C1' C12 C11 O3 179.5(17) . . . . ?
C13 C12 C11 O3 3.1(10) . . . . ?
C11' C12 C11 O3 -145(8) . . . . ?
C1 C12 C11 O1 0.5(8) . . . . ?
C1' C12 C11 O1 -0.5(16) . . . . ?
C13 C12 C11 O1 -177.0(4) . . . . ?
C11' C12 C11 O1 35(7) . . . . ?
C1 C12 C1' C10' -163(32) . . . . ?
C13 C12 C1' C10' 176.7(15) . . . . ?
C11 C12 C1' C10' 1(3) . . . . ?
C11' C12 C1' C10' -5(3) . . . . ?
C1 C12 C1' C2' 16(27) . . . . ?
C13 C12 C1' C2' -4(4) . . . . ?
C11 C12 C1' C2' -180(3) . . . . ?
C11' C12 C1' C2' 174(3) . . . . ?
C12 C1' C2' C3' 1(5) . . . . ?
C10' C1' C2' C3' 180(3) . . . . ?
C12 C1' C2' C7' -179(2) . . . . ?
C10' C1' C2' C7' 0(4) . . . . ?
C1' C2' C3' C4' -176(3) . . . . ?
C7' C2' C3' C4' 3(4) . . . . ?
C2' C3' C4' C5' -4(4) . . . . ?
C3' C4' C5' C6' 0(3) . . . . ?
C4' C5' C6' C7' 2(3) . . . . ?
C5' C6' C7' C2' -2(3) . . . . ?
C5' C6' C7' C8' 177.9(17) . . . . ?
C3' C2' C7' C6' 0(3) . . . . ?
C1' C2' C7' C6' 179(3) . . . . ?
C3' C2' C7' C8' 180(2) . . . . ?
C1' C2' C7' C8' -1(4) . . . . ?
C6' C7' C8' O2' 3(3) . . . . ?
C2' C7' C8' O2' -177(3) . . . . ?
C6' C7' C8' C9' -179.5(19) . . . . ?
C2' C7' C8' C9' 1(3) . . . . ?
O2' C8' C9' C10' 178(2) . . . . ?
C7' C8' C9' C10' 0(3) . . . . ?
O2' C8' C9' C19' -7(3) . . . . ?
C7' C8' C9' C19' 175.2(17) . . . . ?
C8' C9' C10' O1' 176(2) . . . . ?
C19' C9' C10' O1' 2(4) . . . . ?
C8' C9' C10' C1' -1(4) . . . . ?
C19' C9' C10' C1' -175(2) . . . . ?
C11' O1' C10' C9' -175(3) . . . . ?
C11' O1' C10' C1' 2(3) . . . . ?
C12 C1' C10' C9' -180(2) . . . . ?
C2' C1' C10' C9' 1(5) . . . . ?
C12 C1' C10' O1' 2(3) . . . . ?
C2' C1' C10' O1' -177(3) . . . . ?
C10' O1' C11' O3' 170(3) . . . . ?
C10' O1' C11' C12 -6(3) . . . . ?
C1 C12 C11' O3' -169(2) . . . . ?
C1' C12 C11' O3' -170(3) . . . . ?
C13 C12 C11' O3' 9(3) . . . . ?
C11 C12 C11' O3' 44(6) . . . . ?
C1 C12 C11' O1' 7(2) . . . . ?
C1' C12 C11' O1' 6(2) . . . . ?
C13 C12 C11' O1' -175.6(12) . . . . ?
C11 C12 C11' O1' -140(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032
