# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_SSR1
_database_code_depnum_ccdc_archive 'CCDC 1817591'
_audit_update_record             
;
2018-01-17 deposited with the CCDC.
2018-11-21 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         'C20 H18'
_chemical_formula_sum            'C20 H18'
_chemical_formula_weight         258.34

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   15.853(3)
_cell_length_b                   12.375(2)
_cell_length_c                   7.3639(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1444.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    903
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      17.69

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.992
_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            7027
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.088
_diffrn_reflns_theta_max         23.658
_diffrn_reflns_theta_full        23.658
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.842
_reflns_number_total             1836
_reflns_number_gt                1290
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.560
_reflns_Friedel_fraction_max     0.663
_reflns_Friedel_fraction_full    0.664

_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)+(0.0423P)²] 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       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 392 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -5.9(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1836
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.8929(3) 0.3057(3) 0.8639(6) 0.0427(11) Uani 1 1 d . . . . .
C2 C 0.8365(3) 0.3633(3) 0.7713(8) 0.0569(13) Uani 1 1 d . . . . .
H2 H 0.7796 0.3550 0.7988 0.068 Uiso 1 1 calc R U . . .
C3 C 0.8612(3) 0.4408(4) 0.6249(7) 0.0676(15) Uani 1 1 d . . . . .
H3A H 0.8687 0.5122 0.6768 0.081 Uiso 1 1 calc R U . . .
H3B H 0.8164 0.4449 0.5354 0.081 Uiso 1 1 calc R U . . .
C4 C 0.9421(3) 0.4059(4) 0.5331(7) 0.0620(14) Uani 1 1 d . . . . .
H4A H 0.9304 0.3455 0.4531 0.074 Uiso 1 1 calc R U . . .
H4B H 0.9634 0.4650 0.4595 0.074 Uiso 1 1 calc R U . . .
C5 C 1.0080(3) 0.3735(3) 0.6676(7) 0.0467(12) Uani 1 1 d . . . . .
C6 C 1.0935(3) 0.3919(4) 0.6375(8) 0.0632(14) Uani 1 1 d . . . . .
H6 H 1.1103 0.4276 0.5325 0.076 Uiso 1 1 calc R U . . .
C7 C 1.1536(3) 0.3585(4) 0.7600(10) 0.0677(15) Uani 1 1 d . . . . .
H7 H 1.2104 0.3720 0.7382 0.081 Uiso 1 1 calc R U . . .
C8 C 1.1293(3) 0.3053(4) 0.9140(7) 0.0623(15) Uani 1 1 d . . . . .
H8 H 1.1698 0.2811 0.9959 0.075 Uiso 1 1 calc R U . . .
C9 C 1.0448(3) 0.2872(3) 0.9485(7) 0.0530(13) Uani 1 1 d . . . . .
H9 H 1.0288 0.2523 1.0549 0.064 Uiso 1 1 calc R U . . .
C10 C 0.9834(2) 0.3207(3) 0.8259(6) 0.0417(11) Uani 1 1 d . . . . .
C11 C 0.8665(3) 0.2291(3) 1.0069(6) 0.0442(11) Uani 1 1 d . . . . .
C12 C 0.8799(2) 0.1123(4) 0.9764(6) 0.0445(11) Uani 1 1 d . . . . .
C13 C 0.8986(2) 0.0720(4) 0.8065(7) 0.0529(12) Uani 1 1 d . . . . .
H13 H 0.9045 0.1198 0.7100 0.063 Uiso 1 1 calc R U . . .
C14 C 0.9089(3) -0.0382(4) 0.7750(9) 0.0683(15) Uani 1 1 d . . . . .
H14 H 0.9212 -0.0637 0.6592 0.082 Uiso 1 1 calc R U . . .
C15 C 0.9006(3) -0.1078(4) 0.9166(9) 0.0747(17) Uani 1 1 d . . . . .
H15 H 0.9071 -0.1816 0.8973 0.090 Uiso 1 1 calc R U . . .
C16 C 0.8826(3) -0.0706(4) 1.0872(9) 0.0701(17) Uani 1 1 d . . . . .
H16 H 0.8779 -0.1194 1.1826 0.084 Uiso 1 1 calc R U . . .
C17 C 0.8714(3) 0.0395(4) 1.1203(7) 0.0550(13) Uani 1 1 d . . . . .
C18 C 0.8552(3) 0.0844(4) 1.3051(8) 0.0730(16) Uani 1 1 d . . . . .
H18A H 0.9087 0.1034 1.3607 0.088 Uiso 1 1 calc R U . . .
H18B H 0.8291 0.0290 1.3795 0.088 Uiso 1 1 calc R U . . .
C19 C 0.7991(3) 0.1828(4) 1.3025(7) 0.0698(15) Uani 1 1 d . . . . .
H19A H 0.8010 0.2181 1.4200 0.084 Uiso 1 1 calc R U . . .
H19B H 0.7413 0.1610 1.2793 0.084 Uiso 1 1 calc R U . . .
C20 C 0.8276(3) 0.2607(4) 1.1571(7) 0.0569(12) Uani 1 1 d . . . . .
H20 H 0.8175 0.3340 1.1738 0.068 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
C1 C2 1.331(6) . ?
C1 C10 1.474(5) . ?
C1 C11 1.477(6) . ?
C2 C3 1.495(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.513(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.495(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.391(6) . ?
C5 C10 1.392(5) . ?
C6 C7 1.376(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(6) . ?
C9 H9 0.9300 . ?
C11 C20 1.325(6) . ?
C11 C12 1.478(6) . ?
C12 C13 1.379(6) . ?
C12 C17 1.397(6) . ?
C13 C14 1.393(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.358(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.491(7) . ?
C18 C19 1.508(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.510(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20 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
C2 C1 C10 119.3(4) . . ?
C2 C1 C11 121.2(4) . . ?
C10 C1 C11 119.5(4) . . ?
C1 C2 C3 122.5(4) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 111.2(4) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 111.9(4) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C10 118.9(4) . . ?
C6 C5 C4 122.1(5) . . ?
C10 C5 C4 119.0(4) . . ?
C7 C6 C5 121.4(5) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 119.6(5) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.3(5) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 120.7(5) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 119.2(4) . . ?
C9 C10 C1 121.4(4) . . ?
C5 C10 C1 119.4(4) . . ?
C20 C11 C1 122.5(4) . . ?
C20 C11 C12 118.8(4) . . ?
C1 C11 C12 118.6(4) . . ?
C13 C12 C17 118.4(4) . . ?
C13 C12 C11 121.5(4) . . ?
C17 C12 C11 120.1(4) . . ?
C12 C13 C14 122.0(5) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 118.8(6) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 121.0(5) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 119.0(5) . . ?
C16 C17 C18 123.0(5) . . ?
C12 C17 C18 117.9(4) . . ?
C17 C18 C19 113.0(4) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 110.3(4) . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C11 C20 C19 122.9(4) . . ?
C11 C20 H20 118.6 . . ?
C19 C20 H20 118.6 . . ?

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
C10 C1 C2 C3 2.0(7) . . . . ?
C11 C1 C2 C3 -179.5(4) . . . . ?
C1 C2 C3 C4 29.1(7) . . . . ?
C2 C3 C4 C5 -45.9(6) . . . . ?
C3 C4 C5 C6 -146.0(4) . . . . ?
C3 C4 C5 C10 35.7(6) . . . . ?
C10 C5 C6 C7 0.4(6) . . . . ?
C4 C5 C6 C7 -177.9(4) . . . . ?
C5 C6 C7 C8 0.5(7) . . . . ?
C6 C7 C8 C9 -1.4(7) . . . . ?
C7 C8 C9 C10 1.4(7) . . . . ?
C8 C9 C10 C5 -0.4(6) . . . . ?
C8 C9 C10 C1 -177.7(4) . . . . ?
C6 C5 C10 C9 -0.5(6) . . . . ?
C4 C5 C10 C9 177.9(4) . . . . ?
C6 C5 C10 C1 176.8(4) . . . . ?
C4 C5 C10 C1 -4.8(6) . . . . ?
C2 C1 C10 C9 161.8(4) . . . . ?
C11 C1 C10 C9 -16.8(6) . . . . ?
C2 C1 C10 C5 -15.5(6) . . . . ?
C11 C1 C10 C5 166.0(4) . . . . ?
C2 C1 C11 C20 -63.6(6) . . . . ?
C10 C1 C11 C20 114.9(5) . . . . ?
C2 C1 C11 C12 113.1(5) . . . . ?
C10 C1 C11 C12 -68.4(5) . . . . ?
C20 C11 C12 C13 162.4(4) . . . . ?
C1 C11 C12 C13 -14.5(6) . . . . ?
C20 C11 C12 C17 -15.7(6) . . . . ?
C1 C11 C12 C17 167.5(4) . . . . ?
C17 C12 C13 C14 0.1(6) . . . . ?
C11 C12 C13 C14 -178.0(4) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C13 C14 C15 C16 -0.2(8) . . . . ?
C14 C15 C16 C17 0.8(8) . . . . ?
C15 C16 C17 C12 -1.0(7) . . . . ?
C15 C16 C17 C18 -177.4(5) . . . . ?
C13 C12 C17 C16 0.5(6) . . . . ?
C11 C12 C17 C16 178.7(4) . . . . ?
C13 C12 C17 C18 177.2(4) . . . . ?
C11 C12 C17 C18 -4.7(6) . . . . ?
C16 C17 C18 C19 -147.2(4) . . . . ?
C12 C17 C18 C19 36.3(6) . . . . ?
C17 C18 C19 C20 -46.3(6) . . . . ?
C1 C11 C20 C19 179.0(4) . . . . ?
C12 C11 C20 C19 2.2(7) . . . . ?
C18 C19 C20 C11 28.8(7) . . . . ?

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.033



####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 851692'
_audit_update_record             
;
2011-10-31 deposited with the CCDC.
2018-11-21 downloaded from the CCDC.
;
#TrackingRef 'biformyl bichromene new.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 O4'
_chemical_formula_weight         318.31

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   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0844(4)
_cell_length_b                   19.8817(10)
_cell_length_c                   10.2123(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.061(2)
_cell_angle_gamma                90.00
_cell_volume                     1551.44(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3727
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.93

_exptl_crystal_description       Square
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11587
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         28.43
_reflns_number_total             3892
_reflns_number_gt                2722
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0434P)²+0.5358P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3892
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
C1 C -0.0633(2) 0.60119(9) 0.59492(16) 0.0484(4) Uani 1 1 d . . .
H1 H -0.0168 0.6433 0.5876 0.058 Uiso 1 1 calc R . .
C2 C -0.1990(2) 0.57619(11) 0.48544(18) 0.0624(5) Uani 1 1 d . . .
H2 H -0.2412 0.6007 0.4037 0.075 Uiso 1 1 calc R . .
C3 C -0.2721(2) 0.51481(11) 0.4974(2) 0.0665(5) Uani 1 1 d . . .
H3 H -0.3658 0.4987 0.4242 0.080 Uiso 1 1 calc R . .
C4 C -0.2084(2) 0.47720(9) 0.6157(2) 0.0611(5) Uani 1 1 d . . .
H4 H -0.2593 0.4361 0.6232 0.073 Uiso 1 1 calc R . .
C5 C -0.0681(2) 0.50085(8) 0.72383(17) 0.0457(4) Uani 1 1 d . . .
C6 C 0.1701(2) 0.47207(8) 0.9203(2) 0.0563(4) Uani 1 1 d . . .
H6A H 0.2416 0.4496 0.8736 0.068 Uiso 1 1 calc R . .
H6B H 0.1937 0.4513 1.0105 0.068 Uiso 1 1 calc R . .
C7 C 0.2206(2) 0.54489(8) 0.93939(16) 0.0449(3) Uani 1 1 d . . .
C8 C 0.14219(18) 0.58881(7) 0.83841(15) 0.0378(3) Uani 1 1 d . . .
C9 C 0.00487(18) 0.56420(7) 0.71615(15) 0.0388(3) Uani 1 1 d . . .
C10 C 0.3604(2) 0.56460(10) 1.06271(19) 0.0611(5) Uani 1 1 d . . .
H10 H 0.3895 0.6100 1.0733 0.073 Uiso 1 1 calc R . .
C11 C 0.5076(2) 0.76693(10) 0.7348(2) 0.0657(5) Uani 1 1 d . . .
H11 H 0.5348 0.8122 0.7321 0.079 Uiso 1 1 calc R . .
C12 C 0.6006(3) 0.71926(12) 0.6907(2) 0.0741(6) Uani 1 1 d . . .
H12 H 0.6885 0.7324 0.6559 0.089 Uiso 1 1 calc R . .
C13 C 0.5638(3) 0.65212(12) 0.6979(2) 0.0757(6) Uani 1 1 d . . .
H13 H 0.6274 0.6199 0.6687 0.091 Uiso 1 1 calc R . .
C14 C 0.4332(2) 0.63269(9) 0.7484(2) 0.0601(5) Uani 1 1 d . . .
H14 H 0.4109 0.5871 0.7547 0.072 Uiso 1 1 calc R . .
C15 C 0.33370(19) 0.67985(7) 0.79016(15) 0.0421(3) Uani 1 1 d . . .
C16 C 0.19350(18) 0.66155(7) 0.84363(14) 0.0385(3) Uani 1 1 d . . .
C17 C 0.1153(2) 0.71000(7) 0.89407(16) 0.0447(3) Uani 1 1 d . . .
C18 C 0.1657(3) 0.78248(8) 0.8910(2) 0.0590(5) Uani 1 1 d . . .
H18A H 0.0598 0.8085 0.8506 0.071 Uiso 1 1 calc R . .
H18B H 0.2188 0.7977 0.9857 0.071 Uiso 1 1 calc R . .
C19 C 0.3735(2) 0.74767(8) 0.78324(17) 0.0492(4) Uani 1 1 d . . .
C20 C -0.0147(2) 0.69529(9) 0.96028(19) 0.0586(4) Uani 1 1 d . . .
H20 H -0.0531 0.6511 0.9584 0.070 Uiso 1 1 calc R . .
O1 O -0.00962(15) 0.46297(6) 0.84193(14) 0.0591(3) Uani 1 1 d . . .
O2 O 0.44217(18) 0.52695(8) 1.15274(14) 0.0792(4) Uani 1 1 d . . .
O3 O 0.2803(2) 0.79683(6) 0.81831(18) 0.0805(5) Uani 1 1 d . . .
O4 O -0.0760(2) 0.73660(7) 1.01733(17) 0.0833(5) 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 C2 1.378(2) . ?
C1 C9 1.390(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 O1 1.368(2) . ?
C5 C9 1.404(2) . ?
C6 O1 1.423(2) . ?
C6 C7 1.499(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.342(2) . ?
C7 C10 1.445(2) . ?
C8 C9 1.458(2) . ?
C8 C16 1.5007(19) . ?
C10 O2 1.202(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(3) . ?
C11 C19 1.385(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9300 . ?
C15 C19 1.393(2) . ?
C15 C16 1.456(2) . ?
C16 C17 1.344(2) . ?
C17 C20 1.453(2) . ?
C17 C18 1.501(2) . ?
C18 O3 1.392(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O3 1.352(2) . ?
C20 O4 1.203(2) . ?
C20 H20 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
C2 C1 C9 120.71(16) . . ?
C2 C1 H1 119.6 . . ?
C9 C1 H1 119.6 . . ?
C3 C2 C1 119.89(18) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.83(17) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.54(17) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
O1 C5 C4 118.32(15) . . ?
O1 C5 C9 120.82(14) . . ?
C4 C5 C9 120.72(16) . . ?
O1 C6 C7 112.36(13) . . ?
O1 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
O1 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C10 122.14(15) . . ?
C8 C7 C6 119.22(14) . . ?
C10 C7 C6 118.52(14) . . ?
C7 C8 C9 118.43(13) . . ?
C7 C8 C16 122.97(13) . . ?
C9 C8 C16 118.57(12) . . ?
C1 C9 C5 118.23(14) . . ?
C1 C9 C8 123.69(13) . . ?
C5 C9 C8 118.01(13) . . ?
O2 C10 C7 125.15(18) . . ?
O2 C10 H10 117.4 . . ?
C7 C10 H10 117.4 . . ?
C12 C11 C19 120.16(17) . . ?
C12 C11 H11 119.9 . . ?
C19 C11 H11 119.9 . . ?
C13 C12 C11 120.09(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.97(19) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.24(18) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C19 C15 C14 118.08(15) . . ?
C19 C15 C16 118.80(14) . . ?
C14 C15 C16 123.10(14) . . ?
C17 C16 C15 119.07(13) . . ?
C17 C16 C8 123.05(13) . . ?
C15 C16 C8 117.88(12) . . ?
C16 C17 C20 122.44(14) . . ?
C16 C17 C18 121.02(15) . . ?
C20 C17 C18 116.47(14) . . ?
O3 C18 C17 116.14(14) . . ?
O3 C18 H18A 108.3 . . ?
C17 C18 H18A 108.3 . . ?
O3 C18 H18B 108.3 . . ?
C17 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
O3 C19 C11 117.63(15) . . ?
O3 C19 C15 121.90(15) . . ?
C11 C19 C15 120.42(16) . . ?
O4 C20 C17 124.24(17) . . ?
O4 C20 H20 117.9 . . ?
C17 C20 H20 117.9 . . ?
C5 O1 C6 114.91(12) . . ?
C19 O3 C18 121.21(13) . . ?

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
C9 C1 C2 C3 2.0(3) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 O1 178.60(15) . . . . ?
C3 C4 C5 C9 2.8(2) . . . . ?
O1 C6 C7 C8 -33.3(2) . . . . ?
O1 C6 C7 C10 150.56(16) . . . . ?
C10 C7 C8 C9 178.63(14) . . . . ?
C6 C7 C8 C9 2.7(2) . . . . ?
C10 C7 C8 C16 0.7(2) . . . . ?
C6 C7 C8 C16 -175.29(14) . . . . ?
C2 C1 C9 C5 0.1(2) . . . . ?
C2 C1 C9 C8 -176.83(14) . . . . ?
O1 C5 C9 C1 -178.18(13) . . . . ?
C4 C5 C9 C1 -2.5(2) . . . . ?
O1 C5 C9 C8 -1.1(2) . . . . ?
C4 C5 C9 C8 174.57(14) . . . . ?
C7 C8 C9 C1 -167.79(14) . . . . ?
C16 C8 C9 C1 10.3(2) . . . . ?
C7 C8 C9 C5 15.31(19) . . . . ?
C16 C8 C9 C5 -166.64(12) . . . . ?
C8 C7 C10 O2 -175.52(18) . . . . ?
C6 C7 C10 O2 0.5(3) . . . . ?
C19 C11 C12 C13 -1.7(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C19 -1.8(3) . . . . ?
C13 C14 C15 C16 179.71(17) . . . . ?
C19 C15 C16 C17 -4.8(2) . . . . ?
C14 C15 C16 C17 173.64(16) . . . . ?
C19 C15 C16 C8 174.67(14) . . . . ?
C14 C15 C16 C8 -6.9(2) . . . . ?
C7 C8 C16 C17 -93.12(19) . . . . ?
C9 C8 C16 C17 88.93(18) . . . . ?
C7 C8 C16 C15 87.40(18) . . . . ?
C9 C8 C16 C15 -90.55(16) . . . . ?
C15 C16 C17 C20 -174.48(15) . . . . ?
C8 C16 C17 C20 6.0(2) . . . . ?
C15 C16 C17 C18 2.3(2) . . . . ?
C8 C16 C17 C18 -177.12(15) . . . . ?
C16 C17 C18 O3 7.7(3) . . . . ?
C20 C17 C18 O3 -175.31(16) . . . . ?
C12 C11 C19 O3 -176.53(18) . . . . ?
C12 C11 C19 C15 1.2(3) . . . . ?
C14 C15 C19 O3 178.18(16) . . . . ?
C16 C15 C19 O3 -3.3(2) . . . . ?
C14 C15 C19 C11 0.5(2) . . . . ?
C16 C15 C19 C11 179.09(15) . . . . ?
C16 C17 C20 O4 173.15(18) . . . . ?
C18 C17 C20 O4 -3.8(3) . . . . ?
C4 C5 O1 C6 153.41(15) . . . . ?
C9 C5 O1 C6 -30.8(2) . . . . ?
C7 C6 O1 C5 46.6(2) . . . . ?
C11 C19 O3 C18 -168.12(17) . . . . ?
C15 C19 O3 C18 14.2(3) . . . . ?
C17 C18 O3 C19 -15.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042

