# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mo_200908a_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc26hrzg
_database_code_depnum_ccdc_archive 'CCDC 2040946'
loop_
_audit_author_name
_audit_author_address
'Mu Yu'
;Inner Mongolia University
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(R,E)-4-(4-methoxybenzylidene)-3-phenyltetrahydrofuran-3-ol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 O3'
_chemical_formula_weight         282.32
_chemical_absolute_configuration s

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)

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

_cell_length_a                   5.6560(3)
_cell_length_b                   8.2020(4)
_cell_length_c                   16.2422(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.949(2)
_cell_angle_gamma                90.00
_cell_volume                     752.49(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7195
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15629
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         28.29
_reflns_number_total             3702
_reflns_number_gt                2699
_reflns_threshold_expression     >2sigma(I)

_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 (Sheldrick 2014)'
_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)+(0.0574P)²+0.2958P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(17)
_refine_ls_number_reflns         3702
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1487
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.003

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
O3 O 0.1814(4) 0.6968(3) 0.66207(12) 0.0673(6) Uani 1 1 d . . .
O1 O 0.7353(4) 0.8205(4) 0.20838(14) 0.0884(9) Uani 1 1 d . . .
O2 O 0.2231(3) 0.7783(2) 0.14284(12) 0.0514(5) Uani 1 1 d . . .
H2 H 0.1148 0.7875 0.1742 0.077 Uiso 1 1 calc R . .
C18 C -0.0242(6) 0.6411(6) 0.70029(19) 0.0760(10) Uani 1 1 d . . .
H18A H -0.1616 0.6934 0.6752 0.114 Uiso 1 1 calc R . .
H18B H -0.0116 0.6670 0.7580 0.114 Uiso 1 1 calc R . .
H18C H -0.0383 0.5251 0.6935 0.114 Uiso 1 1 calc R . .
C15 C 0.1988(5) 0.6712(3) 0.57976(15) 0.0470(6) Uani 1 1 d . . .
C14 C 0.3842(5) 0.7464(4) 0.54357(17) 0.0512(7) Uani 1 1 d . . .
H14 H 0.4909 0.8084 0.5758 0.061 Uiso 1 1 calc R . .
C13 C 0.4147(4) 0.7316(4) 0.46039(17) 0.0484(6) Uani 1 1 d . . .
H13 H 0.5410 0.7843 0.4373 0.058 Uiso 1 1 calc R . .
C12 C 0.2590(4) 0.6387(3) 0.40998(15) 0.0389(5) Uani 1 1 d . . .
C11 C 0.2736(4) 0.6200(3) 0.32094(16) 0.0424(6) Uani 1 1 d . . .
H11 H 0.1590 0.5515 0.2967 0.051 Uiso 1 1 calc R . .
C10 C 0.4214(4) 0.6833(3) 0.26814(15) 0.0393(5) Uani 1 1 d . . .
C7 C 0.3915(4) 0.6620(3) 0.17569(15) 0.0408(5) Uani 1 1 d . . .
C6 C 0.3356(4) 0.4910(3) 0.14614(15) 0.0406(5) Uani 1 1 d . . .
C5 C 0.4737(6) 0.3604(4) 0.1745(2) 0.0609(8) Uani 1 1 d . . .
H5 H 0.5965 0.3780 0.2138 0.073 Uiso 1 1 calc R . .
C4 C 0.4300(7) 0.2049(4) 0.1449(2) 0.0733(10) Uani 1 1 d . . .
H4 H 0.5257 0.1189 0.1635 0.088 Uiso 1 1 calc R . .
C3 C 0.2470(7) 0.1764(4) 0.08843(19) 0.0679(9) Uani 1 1 d . . .
H3 H 0.2185 0.0714 0.0687 0.082 Uiso 1 1 calc R . .
C17 C 0.0752(5) 0.5635(3) 0.44798(17) 0.0480(6) Uani 1 1 d . . .
H17 H -0.0319 0.5015 0.4159 0.058 Uiso 1 1 calc R . .
C16 C 0.0433(5) 0.5761(4) 0.53147(17) 0.0512(6) Uani 1 1 d . . .
H16 H -0.0807 0.5217 0.5550 0.061 Uiso 1 1 calc R . .
C9 C 0.6332(5) 0.7922(4) 0.28482(18) 0.0600(8) Uani 1 1 d . . .
H9A H 0.5848 0.8944 0.3088 0.072 Uiso 1 1 calc R . .
H9B H 0.7468 0.7398 0.3230 0.072 Uiso 1 1 calc R . .
C8 C 0.6323(5) 0.7185(4) 0.14805(19) 0.0603(8) Uani 1 1 d . . .
H8A H 0.7336 0.6250 0.1400 0.072 Uiso 1 1 calc R . .
H8B H 0.6126 0.7767 0.0962 0.072 Uiso 1 1 calc R . .
C1 C 0.1529(5) 0.4597(3) 0.08890(16) 0.0487(6) Uani 1 1 d . . .
H1 H 0.0591 0.5452 0.0685 0.058 Uiso 1 1 calc R . .
C2 C 0.1071(6) 0.3014(4) 0.06117(19) 0.0653(8) Uani 1 1 d . . .
H2A H -0.0199 0.2815 0.0238 0.078 Uiso 1 1 calc R . .


_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
O3 C15 1.362(3) . ?
O3 C18 1.422(4) . ?
O1 C8 1.393(4) . ?
O1 C9 1.415(4) . ?
O2 C7 1.432(3) . ?
O2 H2 0.8200 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C15 C14 1.375(4) . ?
C15 C16 1.387(4) . ?
C14 C13 1.376(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.397(3) . ?
C13 H13 0.9300 . ?
C12 C17 1.381(3) . ?
C12 C11 1.461(3) . ?
C11 C10 1.333(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.507(4) . ?
C10 C7 1.513(3) . ?
C7 C6 1.511(4) . ?
C7 C8 1.528(4) . ?
C6 C1 1.378(4) . ?
C6 C5 1.390(4) . ?
C5 C4 1.381(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.368(5) . ?
C4 H4 0.9300 . ?
C3 C2 1.356(5) . ?
C3 H3 0.9300 . ?
C17 C16 1.381(4) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.394(4) . ?
C1 H1 0.9300 . ?
C2 H2A 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
C15 O3 C18 118.8(3) . . ?
C8 O1 C9 110.1(2) . . ?
C7 O2 H2 109.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C15 C14 116.5(3) . . ?
O3 C15 C16 124.5(3) . . ?
C14 C15 C16 119.1(2) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C17 C12 C13 116.6(2) . . ?
C17 C12 C11 118.5(2) . . ?
C13 C12 C11 124.8(2) . . ?
C10 C11 C12 131.7(2) . . ?
C10 C11 H11 114.2 . . ?
C12 C11 H11 114.2 . . ?
C11 C10 C9 129.3(2) . . ?
C11 C10 C7 123.5(2) . . ?
C9 C10 C7 107.1(2) . . ?
O2 C7 C10 109.3(2) . . ?
O2 C7 C6 112.1(2) . . ?
C10 C7 C6 115.7(2) . . ?
O2 C7 C8 105.9(2) . . ?
C10 C7 C8 101.6(2) . . ?
C6 C7 C8 111.3(2) . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 C7 121.7(2) . . ?
C5 C6 C7 120.3(2) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C16 C17 C12 123.0(2) . . ?
C16 C17 H17 118.5 . . ?
C12 C17 H17 118.5 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
O1 C9 C10 107.2(2) . . ?
O1 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O1 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
O1 C8 C7 108.8(2) . . ?
O1 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
O1 C8 H8B 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C6 C1 C2 120.8(3) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?

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
C18 O3 C15 C14 171.3(3) . . . . ?
C18 O3 C15 C16 -8.4(4) . . . . ?
O3 C15 C14 C13 -178.4(3) . . . . ?
C16 C15 C14 C13 1.3(4) . . . . ?
C15 C14 C13 C12 -0.4(4) . . . . ?
C14 C13 C12 C17 0.0(4) . . . . ?
C14 C13 C12 C11 178.1(2) . . . . ?
C17 C12 C11 C10 176.5(3) . . . . ?
C13 C12 C11 C10 -1.7(4) . . . . ?
C12 C11 C10 C9 2.9(5) . . . . ?
C12 C11 C10 C7 -173.5(2) . . . . ?
C11 C10 C7 O2 81.9(3) . . . . ?
C9 C10 C7 O2 -95.2(2) . . . . ?
C11 C10 C7 C6 -45.7(3) . . . . ?
C9 C10 C7 C6 137.1(2) . . . . ?
C11 C10 C7 C8 -166.5(3) . . . . ?
C9 C10 C7 C8 16.4(3) . . . . ?
O2 C7 C6 C1 4.9(3) . . . . ?
C10 C7 C6 C1 131.2(2) . . . . ?
C8 C7 C6 C1 -113.5(3) . . . . ?
O2 C7 C6 C5 -177.1(2) . . . . ?
C10 C7 C6 C5 -50.8(3) . . . . ?
C8 C7 C6 C5 64.5(3) . . . . ?
C1 C6 C5 C4 1.0(5) . . . . ?
C7 C6 C5 C4 -177.0(3) . . . . ?
C6 C5 C4 C3 -1.4(5) . . . . ?
C5 C4 C3 C2 0.0(6) . . . . ?
C13 C12 C17 C16 -0.5(4) . . . . ?
C11 C12 C17 C16 -178.8(3) . . . . ?
C12 C17 C16 C15 1.4(4) . . . . ?
O3 C15 C16 C17 178.0(3) . . . . ?
C14 C15 C16 C17 -1.8(4) . . . . ?
C8 O1 C9 C10 -9.9(4) . . . . ?
C11 C10 C9 O1 177.9(3) . . . . ?
C7 C10 C9 O1 -5.2(3) . . . . ?
C9 O1 C8 C7 21.2(4) . . . . ?
O2 C7 C8 O1 91.3(3) . . . . ?
C10 C7 C8 O1 -22.9(3) . . . . ?
C6 C7 C8 O1 -146.7(2) . . . . ?
C5 C6 C1 C2 0.7(4) . . . . ?
C7 C6 C1 C2 178.7(3) . . . . ?
C4 C3 C2 C1 1.7(5) . . . . ?
C6 C1 C2 C3 -2.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_mo_200909a_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc26hs0j
_database_code_depnum_ccdc_archive 'CCDC 2040947'
loop_
_audit_author_name
_audit_author_address
'Mu Yu'
;Inner Mongolia University
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(R,E)-3-benzyl-4-benzylidenetetrahydrofuran-3-ol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 O2'
_chemical_formula_weight         266.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.5109(8)
_cell_length_b                   8.5749(12)
_cell_length_c                   26.234(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1464.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.10

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30162
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         27.22
_reflns_number_total             3243
_reflns_number_gt                2536
_reflns_threshold_expression     >2sigma(I)

_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 (Sheldrick 2014)'
_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)+(0.0492P)²+0.4730P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         3243
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.007
_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
O2 O 0.2919(5) 0.72665(19) 0.02660(10) 0.1085(9) Uani 1 1 d . . .
H2 H 0.4052 0.7640 0.0205 0.163 Uiso 1 1 calc R . .
O1 O -0.0232(3) 0.4934(4) 0.01183(9) 0.1294(11) Uani 1 1 d . . .
C1 C 0.5190(5) 0.3050(4) -0.20143(11) 0.0889(9) Uani 1 1 d . . .
H1 H 0.5331 0.2672 -0.2345 0.107 Uiso 1 1 calc R . .
C6 C 0.6444(5) 0.4210(4) -0.18429(12) 0.0926(9) Uani 1 1 d . . .
H6 H 0.7428 0.4631 -0.2060 0.111 Uiso 1 1 calc R . .
C5 C 0.6270(4) 0.4765(4) -0.13527(10) 0.0748(7) Uani 1 1 d . . .
H5 H 0.7159 0.5540 -0.1239 0.090 Uiso 1 1 calc R . .
C4 C 0.4779(3) 0.4179(3) -0.10248(8) 0.0552(5) Uani 1 1 d . . .
C7 C 0.4656(3) 0.4822(3) -0.05061(8) 0.0544(5) Uani 1 1 d . . .
H7 H 0.5858 0.5274 -0.0384 0.065 Uiso 1 1 calc R . .
C8 C 0.3085(3) 0.4847(2) -0.01891(8) 0.0474(5) Uani 1 1 d . . .
C11 C 0.3102(3) 0.5630(2) 0.03292(9) 0.0508(5) Uani 1 1 d . . .
C12 C 0.4930(3) 0.5221(3) 0.06550(8) 0.0585(6) Uani 1 1 d . . .
H12A H 0.4963 0.4098 0.0698 0.070 Uiso 1 1 calc R . .
H12B H 0.6166 0.5518 0.0473 0.070 Uiso 1 1 calc R . .
C13 C 0.4981(3) 0.5968(3) 0.11744(8) 0.0549(5) Uani 1 1 d . . .
C14 C 0.6155(4) 0.7272(3) 0.12658(9) 0.0679(6) Uani 1 1 d . . .
H14 H 0.6927 0.7700 0.1002 0.082 Uiso 1 1 calc R . .
C15 C 0.6205(5) 0.7955(4) 0.17400(10) 0.0839(8) Uani 1 1 d . . .
H15 H 0.7008 0.8837 0.1794 0.101 Uiso 1 1 calc R . .
C16 C 0.5089(5) 0.7351(4) 0.21301(10) 0.0848(8) Uani 1 1 d . . .
H16 H 0.5116 0.7820 0.2450 0.102 Uiso 1 1 calc R . .
C2 C 0.3730(5) 0.2448(4) -0.16990(10) 0.0811(8) Uani 1 1 d . . .
H2A H 0.2864 0.1661 -0.1814 0.097 Uiso 1 1 calc R . .
C3 C 0.3537(4) 0.3005(3) -0.12095(9) 0.0673(7) Uani 1 1 d . . .
H3 H 0.2542 0.2577 -0.0997 0.081 Uiso 1 1 calc R . .
C18 C 0.3874(4) 0.5352(3) 0.15758(9) 0.0724(7) Uani 1 1 d . . .
H18 H 0.3085 0.4461 0.1527 0.087 Uiso 1 1 calc R . .
C17 C 0.3930(5) 0.6054(4) 0.20501(10) 0.0834(9) Uani 1 1 d . . .
H17 H 0.3169 0.5636 0.2317 0.100 Uiso 1 1 calc R . .
C10 C 0.1079(4) 0.5095(5) 0.05436(12) 0.0996(11) Uani 1 1 d . . .
H10A H 0.1233 0.4107 0.0719 0.120 Uiso 1 1 calc R . .
H10B H 0.0536 0.5858 0.0781 0.120 Uiso 1 1 calc R . .
C9 C 0.0958(3) 0.4224(3) -0.02634(11) 0.0734(7) Uani 1 1 d . . .
H9A H 0.0443 0.4492 -0.0599 0.088 Uiso 1 1 calc R . .
H9B H 0.0940 0.3099 -0.0227 0.088 Uiso 1 1 calc R . .


_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 C11 1.418(2) . ?
O2 H2 0.8200 . ?
O1 C9 1.405(3) . ?
O1 C10 1.411(3) . ?
C1 C2 1.362(4) . ?
C1 C6 1.363(4) . ?
C1 H1 0.9300 . ?
C6 C5 1.376(4) . ?
C6 H6 0.9300 . ?
C5 C4 1.391(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.379(3) . ?
C4 C7 1.470(3) . ?
C7 C8 1.318(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.497(3) . ?
C8 C11 1.516(3) . ?
C11 C10 1.504(3) . ?
C11 C12 1.507(3) . ?
C12 C13 1.506(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.376(3) . ?
C13 C18 1.381(3) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.358(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(5) . ?
C16 H16 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2A 0.9300 . ?
C3 H3 0.9300 . ?
C18 C17 1.383(4) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 O2 H2 109.5 . . ?
C9 O1 C10 105.8(2) . . ?
C2 C1 C6 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C3 C4 C5 117.1(2) . . ?
C3 C4 C7 124.6(2) . . ?
C5 C4 C7 118.3(2) . . ?
C8 C7 C4 129.19(19) . . ?
C8 C7 H7 115.4 . . ?
C4 C7 H7 115.4 . . ?
C7 C8 C9 129.0(2) . . ?
C7 C8 C11 124.56(18) . . ?
C9 C8 C11 106.34(18) . . ?
O2 C11 C10 105.8(3) . . ?
O2 C11 C12 111.3(2) . . ?
C10 C11 C12 114.1(2) . . ?
O2 C11 C8 109.43(19) . . ?
C10 C11 C8 101.19(18) . . ?
C12 C11 C8 114.28(16) . . ?
C13 C12 C11 115.59(17) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C18 117.9(2) . . ?
C14 C13 C12 121.0(2) . . ?
C18 C13 C12 121.1(2) . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C13 C18 C17 120.4(3) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
O1 C10 C11 105.3(2) . . ?
O1 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
O1 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
O1 C9 C8 105.23(19) . . ?
O1 C9 H9A 110.7 . . ?
C8 C9 H9A 110.7 . . ?
O1 C9 H9B 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.22
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.030
