# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_qiuyf_69b
_database_code_depnum_ccdc_archive 'CCDC 1058971'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;
_audit_creation_date             2015-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H18 O2'
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34
_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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   15.2594(7)
_cell_length_b                   10.4298(5)
_cell_length_c                   19.4355(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3093.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1844
_cell_measurement_temperature    293.51(10)
_cell_measurement_theta_max      23.9870
_cell_measurement_theta_min      3.9310
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8066
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.39
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.51(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416   19.0000 -120.0000 107

#__ type_ start__ end____ width___ exp.time_
  2 omega  -12.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000 -120.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0345108000
_diffrn_orient_matrix_UB_12      -0.0456064000
_diffrn_orient_matrix_UB_13      0.0012926000
_diffrn_orient_matrix_UB_21      -0.0284996000
_diffrn_orient_matrix_UB_22      0.0473149000
_diffrn_orient_matrix_UB_23      0.0135082000
_diffrn_orient_matrix_UB_31      -0.0126385000
_diffrn_orient_matrix_UB_32      0.0172673000
_diffrn_orient_matrix_UB_33      -0.0338924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2077
_reflns_number_total             3032
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0521P)²+0.4024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1393
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C7(H7), C8(H8), C20(H20), C18(H18), C5(H5), C17(H17), C6(H6),
 C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O2 O 0.68260(12) 0.29627(17) 0.44149(8) 0.0796(5) Uani 1 d . . .
O1 O 0.74893(9) 0.56009(14) 0.33834(7) 0.0562(4) Uani 1 d . . .
C19 C 0.37039(15) 0.3349(2) 0.44992(10) 0.0552(6) Uani 1 d . . .
H19 H 0.3763 0.2685 0.4815 0.066 Uiso 1 calc . . R
C7 C 0.44496(15) 0.9232(2) 0.43091(11) 0.0550(6) Uani 1 d . . .
H7 H 0.4155 0.9587 0.4682 0.066 Uiso 1 calc . . R
C3 C 0.57587(14) 0.7600(2) 0.25591(10) 0.0502(5) Uani 1 d . . .
H3A H 0.5813 0.8263 0.2212 0.060 Uiso 1 calc . . R
H3B H 0.5385 0.6932 0.2373 0.060 Uiso 1 calc . . R
C2 C 0.66636(14) 0.7035(2) 0.26971(10) 0.0545(6) Uani 1 d . . .
H2A H 0.6817 0.6451 0.2328 0.065 Uiso 1 calc . . R
H2B H 0.7094 0.7719 0.2704 0.065 Uiso 1 calc . . R
C8 C 0.45348(14) 0.79127(19) 0.42534(9) 0.0447(5) Uani 1 d . . .
H8 H 0.4288 0.7388 0.4588 0.054 Uiso 1 calc . . R
C20 C 0.44155(14) 0.41254(18) 0.43470(9) 0.0454(5) Uani 1 d . . .
H20 H 0.4947 0.3982 0.4567 0.055 Uiso 1 calc . . R
C18 C 0.29108(16) 0.3558(2) 0.41832(11) 0.0613(6) Uani 1 d . . .
H18 H 0.2435 0.3031 0.4280 0.074 Uiso 1 calc . . R
C5 C 0.52251(16) 0.9486(2) 0.32529(11) 0.0559(6) Uani 1 d . . .
H5 H 0.5452 1.0022 0.2914 0.067 Uiso 1 calc . . R
C17 C 0.28244(15) 0.4554(2) 0.37215(11) 0.0618(6) Uani 1 d . . .
H17 H 0.2287 0.4702 0.3511 0.074 Uiso 1 calc . . R
C6 C 0.48051(16) 1.0019(2) 0.38072(11) 0.0604(6) Uani 1 d . . .
H6 H 0.4759 1.0906 0.3846 0.072 Uiso 1 calc . . R
C4 C 0.53213(13) 0.81636(17) 0.31834(9) 0.0422(5) Uani 1 d . . .
C16 C 0.35304(14) 0.5333(2) 0.35690(10) 0.0489(5) Uani 1 d . . .
H16 H 0.3459 0.6010 0.3262 0.059 Uiso 1 calc . . R
C12 C 0.61467(14) 0.40484(18) 0.34623(10) 0.0496(5) Uani 1 d . . .
H12A H 0.5639 0.3516 0.3554 0.060 Uiso 1 calc . . R
H12B H 0.6369 0.3840 0.3008 0.060 Uiso 1 calc . . R
C13 C 0.68409(15) 0.3827(2) 0.39965(11) 0.0548(6) Uani 1 d . . .
C1 C 0.66905(13) 0.63217(19) 0.33781(9) 0.0444(5) Uani 1 d . . .
H1 H 0.6716 0.6955 0.3750 0.053 Uiso 1 calc . . R
C15 C 0.43476(13) 0.51201(17) 0.38682(9) 0.0389(5) Uani 1 d . . .
C14 C 0.75542(15) 0.4825(2) 0.39812(11) 0.0602(6) Uani 1 d . . .
H14A H 0.7510 0.5362 0.4387 0.072 Uiso 1 calc . . R
H14B H 0.8121 0.4405 0.3989 0.072 Uiso 1 calc . . R
C9 C 0.49838(12) 0.73590(17) 0.37031(8) 0.0377(5) Uani 1 d . . .
C11 C 0.59024(13) 0.54571(17) 0.35017(9) 0.0397(5) Uani 1 d . . .
C10 C 0.51162(13) 0.59360(17) 0.36796(8) 0.0380(5) Uani 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
O2 C13 1.214(2) . ?
O1 C1 1.432(2) . ?
O1 C14 1.419(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(3) . ?
C19 C18 1.375(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C7 C6 1.386(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.525(3) . ?
C3 C4 1.505(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.519(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.395(3) . ?
C20 H20 0.9300 . ?
C20 C15 1.397(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(3) . ?
C5 C4 1.394(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.382(3) . ?
C6 H6 0.9300 . ?
C4 C9 1.411(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.394(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.501(3) . ?
C12 C11 1.518(3) . ?
C13 C14 1.506(3) . ?
C1 H1 0.9800 . ?
C1 C11 1.522(3) . ?
C15 C10 1.495(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C9 C10 1.499(3) . ?
C11 C10 1.345(3) . ?

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
C14 O1 C1 111.38(15) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.10(19) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.78(19) . . ?
H3A C3 H3B 107.6 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C4 C3 C2 114.25(16) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 C3 111.54(16) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.12(19) . . ?
C9 C8 H8 119.4 . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C15 121.18(19) . . ?
C15 C20 H20 119.4 . . ?
C19 C18 H18 120.2 . . ?
C19 C18 C17 119.6(2) . . ?
C17 C18 H18 120.2 . . ?
C6 C5 H5 119.1 . . ?
C6 C5 C4 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C18 C17 H17 119.7 . . ?
C18 C17 C16 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C7 C6 H6 120.2 . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C5 C4 C3 120.77(17) . . ?
C5 C4 C9 118.75(18) . . ?
C9 C4 C3 120.47(16) . . ?
C17 C16 H16 119.5 . . ?
C17 C16 C15 120.95(19) . . ?
C15 C16 H16 119.5 . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C13 C12 C11 106.70(16) . . ?
C11 C12 H12A 110.4 . . ?
C11 C12 H12B 110.4 . . ?
O2 C13 C12 124.3(2) . . ?
O2 C13 C14 122.7(2) . . ?
C12 C13 C14 112.95(18) . . ?
O1 C1 C2 106.64(15) . . ?
O1 C1 H1 108.3 . . ?
O1 C1 C11 111.12(15) . . ?
C2 C1 H1 108.3 . . ?
C2 C1 C11 113.96(16) . . ?
C11 C1 H1 108.3 . . ?
C20 C15 C10 121.86(18) . . ?
C16 C15 C20 117.55(19) . . ?
C16 C15 C10 120.59(16) . . ?
O1 C14 C13 111.08(18) . . ?
O1 C14 H14A 109.4 . . ?
O1 C14 H14B 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C8 C9 C4 118.81(17) . . ?
C8 C9 C10 119.97(16) . . ?
C4 C9 C10 121.21(16) . . ?
C12 C11 C1 111.80(17) . . ?
C10 C11 C12 126.28(18) . . ?
C10 C11 C1 121.69(16) . . ?
C15 C10 C9 116.78(16) . . ?
C11 C10 C15 123.48(17) . . ?
C11 C10 C9 119.73(18) . . ?

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
O2 C13 C14 O1 171.09(19) . . . . ?
O1 C1 C11 C12 -10.8(2) . . . . ?
O1 C1 C11 C10 164.04(16) . . . . ?
C19 C20 C15 C16 2.4(3) . . . . ?
C19 C20 C15 C10 -177.77(17) . . . . ?
C19 C18 C17 C16 0.7(3) . . . . ?
C7 C8 C9 C4 -2.7(3) . . . . ?
C7 C8 C9 C10 176.03(19) . . . . ?
C3 C2 C1 O1 167.34(17) . . . . ?
C3 C2 C1 C11 44.4(2) . . . . ?
C3 C4 C9 C8 -176.07(17) . . . . ?
C3 C4 C9 C10 5.2(3) . . . . ?
C2 C3 C4 C5 108.7(2) . . . . ?
C2 C3 C4 C9 -72.7(2) . . . . ?
C2 C1 C11 C12 109.69(18) . . . . ?
C2 C1 C11 C10 -75.5(2) . . . . ?
C8 C7 C6 C5 1.1(3) . . . . ?
C8 C9 C10 C15 43.3(2) . . . . ?
C8 C9 C10 C11 -136.01(19) . . . . ?
C20 C19 C18 C17 -0.8(3) . . . . ?
C20 C15 C10 C9 -129.97(18) . . . . ?
C20 C15 C10 C11 49.3(3) . . . . ?
C18 C19 C20 C15 -0.7(3) . . . . ?
C18 C17 C16 C15 1.1(3) . . . . ?
C5 C4 C9 C8 2.6(3) . . . . ?
C5 C4 C9 C10 -176.12(19) . . . . ?
C17 C16 C15 C20 -2.5(3) . . . . ?
C17 C16 C15 C10 177.61(18) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C6 C5 C4 C3 178.0(2) . . . . ?
C6 C5 C4 C9 -0.7(3) . . . . ?
C4 C3 C2 C1 39.9(2) . . . . ?
C4 C5 C6 C7 -1.2(4) . . . . ?
C4 C9 C10 C15 -137.99(18) . . . . ?
C4 C9 C10 C11 42.7(3) . . . . ?
C16 C15 C10 C9 49.9(2) . . . . ?
C16 C15 C10 C11 -130.8(2) . . . . ?
C12 C13 C14 O1 -11.0(2) . . . . ?
C12 C11 C10 C15 -0.1(3) . . . . ?
C12 C11 C10 C9 179.14(16) . . . . ?
C13 C12 C11 C1 58.5(2) . . . . ?
C13 C12 C11 C10 -116.0(2) . . . . ?
C1 O1 C14 C13 63.8(2) . . . . ?
C1 C11 C10 C15 -174.21(15) . . . . ?
C1 C11 C10 C9 5.1(3) . . . . ?
C14 O1 C1 C2 -176.05(16) . . . . ?
C14 O1 C1 C11 -51.3(2) . . . . ?
C11 C12 C13 O2 130.9(2) . . . . ?
C11 C12 C13 C14 -46.9(2) . . . . ?

_olex2_date_sample_data_collection 2015-04-02
_olex2_submission_special_instructions 'No special instructions were received'
