# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_z
_database_code_depnum_ccdc_archive 'CCDC 1437982'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 O2 Si'
_chemical_formula_weight         328.51

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'
Si Si 0.0817 0.0704 '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)/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                   7.5687(5)
_cell_length_b                   30.831(2)
_cell_length_c                   8.0907(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.916(2)
_cell_angle_gamma                90.00
_cell_volume                     1887.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21646
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3312
_reflns_number_gt                2576
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0488P)²+1.7996P] 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_number_reflns         3312
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
Si1 Si 0.96470(10) 0.16712(2) 0.02438(9) 0.0314(2) Uani 1 1 d . . .
O1 O 0.1989(2) -0.01322(7) 0.2977(2) 0.0406(5) Uani 1 1 d . . .
O2 O 0.8979(3) 0.12042(6) -0.0523(2) 0.0363(5) Uani 1 1 d . . .
C1 C 0.4040(4) -0.09129(9) 0.4498(4) 0.0373(7) Uani 1 1 d . . .
H1A H 0.3018 -0.1033 0.3870 0.045 Uiso 1 1 calc R . .
H1B H 0.3643 -0.0839 0.5624 0.045 Uiso 1 1 calc R . .
C2 C 0.5511(4) -0.12500(10) 0.4602(4) 0.0478(8) Uani 1 1 d . . .
H2A H 0.5179 -0.1477 0.5403 0.057 Uiso 1 1 calc R . .
H2B H 0.5632 -0.1390 0.3508 0.057 Uiso 1 1 calc R . .
C3 C 0.7279(4) -0.10570(10) 0.5126(4) 0.0460(8) Uani 1 1 d . . .
H3A H 0.8172 -0.1291 0.5196 0.055 Uiso 1 1 calc R . .
H3B H 0.7172 -0.0928 0.6240 0.055 Uiso 1 1 calc R . .
C4 C 0.7908(4) -0.07110(9) 0.3930(4) 0.0359(7) Uani 1 1 d . . .
H4A H 0.8835 -0.0532 0.4474 0.043 Uiso 1 1 calc R . .
H4B H 0.8429 -0.0852 0.2952 0.043 Uiso 1 1 calc R . .
C5 C 0.6404(3) -0.04260(8) 0.3389(3) 0.0281(6) Uani 1 1 d . . .
C6 C 0.4696(3) -0.05160(9) 0.3663(3) 0.0300(6) Uani 1 1 d . . .
C7 C 0.3590(3) -0.01653(9) 0.2927(3) 0.0299(6) Uani 1 1 d . . .
C8 C 0.4854(3) 0.01404(8) 0.2120(3) 0.0266(6) Uani 1 1 d . . .
C9 C 0.6557(3) -0.00173(8) 0.2443(3) 0.0270(6) Uani 1 1 d . . .
C10 C 0.8006(3) 0.02010(8) 0.1858(3) 0.0289(6) Uani 1 1 d . . .
H10A H 0.9167 0.0097 0.2082 0.035 Uiso 1 1 calc R . .
C11 C 0.7736(3) 0.05805(8) 0.0922(3) 0.0286(6) Uani 1 1 d . . .
C12 C 0.6046(3) 0.07309(9) 0.0599(3) 0.0298(6) Uani 1 1 d . . .
H12A H 0.5878 0.0987 -0.0037 0.036 Uiso 1 1 calc R . .
C13 C 0.4580(3) 0.05074(9) 0.1204(3) 0.0299(6) Uani 1 1 d . . .
H13A H 0.3415 0.0609 0.0981 0.036 Uiso 1 1 calc R . .
C14 C 0.9351(4) 0.08003(9) 0.0257(4) 0.0377(7) Uani 1 1 d . . .
H14A H 1.0206 0.0849 0.1178 0.045 Uiso 1 1 calc R . .
H14B H 0.9916 0.0605 -0.0550 0.045 Uiso 1 1 calc R . .
C15 C 0.8735(5) 0.17467(12) 0.2343(4) 0.0554(9) Uani 1 1 d . . .
H15A H 0.9222 0.1525 0.3088 0.083 Uiso 1 1 calc R . .
H15B H 0.7445 0.1720 0.2289 0.083 Uiso 1 1 calc R . .
H15C H 0.9057 0.2035 0.2758 0.083 Uiso 1 1 calc R . .
C16 C 1.2106(4) 0.16806(11) 0.0361(5) 0.0540(9) Uani 1 1 d . . .
H16A H 1.2522 0.1462 0.1155 0.081 Uiso 1 1 calc R . .
H16B H 1.2506 0.1968 0.0720 0.081 Uiso 1 1 calc R . .
H16C H 1.2583 0.1617 -0.0731 0.081 Uiso 1 1 calc R . .
C17 C 0.8770(4) 0.20878(9) -0.1242(4) 0.0407(7) Uani 1 1 d . . .
C18 C 0.9324(5) 0.25439(10) -0.0701(5) 0.0644(11) Uani 1 1 d . . .
H18A H 0.8862 0.2757 -0.1498 0.097 Uiso 1 1 calc R . .
H18B H 1.0616 0.2562 -0.0652 0.097 Uiso 1 1 calc R . .
H18C H 0.8848 0.2605 0.0394 0.097 Uiso 1 1 calc R . .
C19 C 0.6753(5) 0.20664(12) -0.1302(5) 0.0632(10) Uani 1 1 d . . .
H19A H 0.6296 0.2282 -0.2089 0.095 Uiso 1 1 calc R . .
H19B H 0.6291 0.2127 -0.0201 0.095 Uiso 1 1 calc R . .
H19C H 0.6377 0.1776 -0.1654 0.095 Uiso 1 1 calc R . .
C20 C 0.9462(6) 0.19979(12) -0.2975(4) 0.0681(11) Uani 1 1 d . . .
H20A H 0.8997 0.2217 -0.3746 0.102 Uiso 1 1 calc R . .
H20B H 0.9078 0.1709 -0.3336 0.102 Uiso 1 1 calc R . .
H20C H 1.0756 0.2010 -0.2953 0.102 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
Si1 O2 1.644(2) . ?
Si1 C15 1.858(3) . ?
Si1 C16 1.862(3) . ?
Si1 C17 1.874(3) . ?
O1 C7 1.218(3) . ?
O2 C14 1.422(3) . ?
C1 C6 1.487(4) . ?
C1 C2 1.524(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.519(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.522(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.498(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.344(4) . ?
C5 C9 1.480(4) . ?
C6 C7 1.486(4) . ?
C7 C8 1.500(4) . ?
C8 C13 1.367(4) . ?
C8 C9 1.398(3) . ?
C9 C10 1.377(4) . ?
C10 C11 1.407(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(4) . ?
C11 C14 1.505(4) . ?
C12 C13 1.401(4) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C19 1.528(4) . ?
C17 C18 1.530(4) . ?
C17 C20 1.530(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O2 Si1 C15 109.75(14) . . ?
O2 Si1 C16 109.51(13) . . ?
C15 Si1 C16 109.70(17) . . ?
O2 Si1 C17 104.75(12) . . ?
C15 Si1 C17 111.56(15) . . ?
C16 Si1 C17 111.45(15) . . ?
C14 O2 Si1 122.81(18) . . ?
C6 C1 C2 109.7(2) . . ?
C6 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
C6 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 C1 112.8(3) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 112.4(3) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 110.7(2) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C9 110.2(2) . . ?
C6 C5 C4 124.0(2) . . ?
C9 C5 C4 125.8(2) . . ?
C5 C6 C7 108.7(2) . . ?
C5 C6 C1 125.0(2) . . ?
C7 C6 C1 126.2(2) . . ?
O1 C7 C6 127.0(3) . . ?
O1 C7 C8 127.2(2) . . ?
C6 C7 C8 105.8(2) . . ?
C13 C8 C9 121.4(2) . . ?
C13 C8 C7 131.6(2) . . ?
C9 C8 C7 107.0(2) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 C5 131.6(2) . . ?
C8 C9 C5 108.2(2) . . ?
C9 C10 C11 118.8(2) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 C14 122.4(2) . . ?
C10 C11 C14 117.1(2) . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C8 C13 C12 118.8(2) . . ?
C8 C13 H13A 120.6 . . ?
C12 C13 H13A 120.6 . . ?
O2 C14 C11 113.4(2) . . ?
O2 C14 H14A 108.9 . . ?
C11 C14 H14A 108.9 . . ?
O2 C14 H14B 108.9 . . ?
C11 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C17 C18 108.5(3) . . ?
C19 C17 C20 108.7(3) . . ?
C18 C17 C20 109.4(3) . . ?
C19 C17 Si1 109.5(2) . . ?
C18 C17 Si1 110.7(2) . . ?
C20 C17 Si1 109.9(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C15 Si1 O2 C14 -59.2(2) . . . . ?
C16 Si1 O2 C14 61.3(2) . . . . ?
C17 Si1 O2 C14 -179.1(2) . . . . ?
C6 C1 C2 C3 43.9(3) . . . . ?
C1 C2 C3 C4 -60.1(4) . . . . ?
C2 C3 C4 C5 41.5(3) . . . . ?
C3 C4 C5 C6 -12.1(4) . . . . ?
C3 C4 C5 C9 170.0(3) . . . . ?
C9 C5 C6 C7 -0.8(3) . . . . ?
C4 C5 C6 C7 -179.0(2) . . . . ?
C9 C5 C6 C1 176.6(2) . . . . ?
C4 C5 C6 C1 -1.6(4) . . . . ?
C2 C1 C6 C5 -14.3(4) . . . . ?
C2 C1 C6 C7 162.7(3) . . . . ?
C5 C6 C7 O1 -177.7(3) . . . . ?
C1 C6 C7 O1 4.9(4) . . . . ?
C5 C6 C7 C8 2.0(3) . . . . ?
C1 C6 C7 C8 -175.4(2) . . . . ?
O1 C7 C8 C13 -3.4(5) . . . . ?
C6 C7 C8 C13 176.9(3) . . . . ?
O1 C7 C8 C9 177.3(3) . . . . ?
C6 C7 C8 C9 -2.4(3) . . . . ?
C13 C8 C9 C10 1.0(4) . . . . ?
C7 C8 C9 C10 -179.6(2) . . . . ?
C13 C8 C9 C5 -177.4(2) . . . . ?
C7 C8 C9 C5 2.0(3) . . . . ?
C6 C5 C9 C10 -179.0(3) . . . . ?
C4 C5 C9 C10 -0.8(4) . . . . ?
C6 C5 C9 C8 -0.8(3) . . . . ?
C4 C5 C9 C8 177.4(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C5 C9 C10 C11 177.4(3) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C9 C10 C11 C14 -177.9(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C14 C11 C12 C13 178.0(2) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
C7 C8 C13 C12 180.0(3) . . . . ?
C11 C12 C13 C8 0.2(4) . . . . ?
Si1 O2 C14 C11 112.2(2) . . . . ?
C12 C11 C14 O2 8.3(4) . . . . ?
C10 C11 C14 O2 -173.8(2) . . . . ?
O2 Si1 C17 C19 61.4(2) . . . . ?
C15 Si1 C17 C19 -57.3(3) . . . . ?
C16 Si1 C17 C19 179.7(2) . . . . ?
O2 Si1 C17 C18 -178.9(2) . . . . ?
C15 Si1 C17 C18 62.4(3) . . . . ?
C16 Si1 C17 C18 -60.6(3) . . . . ?
O2 Si1 C17 C20 -57.9(3) . . . . ?
C15 Si1 C17 C20 -176.6(2) . . . . ?
C16 Si1 C17 C20 60.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1437983'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 F3 O'
_chemical_formula_weight         252.23

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'
F F 0.0171 0.0103 '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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3733(6)
_cell_length_b                   11.2959(9)
_cell_length_c                   14.9182(10)
_cell_angle_alpha                109.524(3)
_cell_angle_beta                 92.663(3)
_cell_angle_gamma                101.436(3)
_cell_volume                     1139.24(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13465
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_sigmaI/netI    0.0925
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3998
_reflns_number_gt                2300
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0670P)²+1.0695P] 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_number_reflns         3998
_refine_ls_number_parameters     352
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1873
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.039
_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
F4 F 0.1039(4) 0.3343(3) 0.5407(2) 0.0813(10) Uani 1 1 d . . .
F5 F 0.2109(5) 0.4677(3) 0.4753(2) 0.0792(10) Uani 1 1 d . . .
F6 F 0.3939(4) 0.4102(3) 0.55630(19) 0.0743(9) Uani 1 1 d . . .
O2 O 0.3020(4) -0.0959(3) 0.08983(18) 0.0487(8) Uani 1 1 d . . .
C15 C 0.2860(5) -0.0957(4) 0.3222(3) 0.0318(9) Uani 1 1 d . . .
C16 C 0.2826(6) -0.1541(4) 0.3985(3) 0.0400(10) Uani 1 1 d . . .
H16A H 0.1836 -0.1320 0.4370 0.048 Uiso 1 1 calc R . .
H16B H 0.3999 -0.1194 0.4401 0.048 Uiso 1 1 calc R . .
C17 C 0.2510(6) -0.3008(4) 0.3542(3) 0.0474(11) Uani 1 1 d . . .
H17A H 0.2836 -0.3343 0.4032 0.057 Uiso 1 1 calc R . .
H17B H 0.1199 -0.3374 0.3308 0.057 Uiso 1 1 calc R . .
C18 C 0.3650(6) -0.3421(4) 0.2726(3) 0.0477(11) Uani 1 1 d . . .
H18A H 0.3442 -0.4354 0.2486 0.057 Uiso 1 1 calc R . .
H18B H 0.4963 -0.3069 0.2962 0.057 Uiso 1 1 calc R . .
C19 C 0.3153(6) -0.2969(4) 0.1908(3) 0.0398(10) Uani 1 1 d . . .
H19A H 0.4110 -0.3047 0.1481 0.048 Uiso 1 1 calc R . .
H19B H 0.1980 -0.3509 0.1543 0.048 Uiso 1 1 calc R . .
C20 C 0.2991(5) -0.1603(4) 0.2297(3) 0.0330(9) Uani 1 1 d . . .
C21 C 0.2948(5) -0.0715(4) 0.1750(3) 0.0327(9) Uani 1 1 d . . .
C22 C 0.2831(5) 0.0556(4) 0.2470(2) 0.0316(9) Uani 1 1 d . . .
C23 C 0.2768(5) 0.0384(4) 0.3365(2) 0.0296(9) Uani 1 1 d . . .
C24 C 0.2632(5) 0.1388(4) 0.4169(3) 0.0325(9) Uani 1 1 d . . .
H24A H 0.2580 0.1287 0.4762 0.039 Uiso 1 1 calc R . .
C25 C 0.2573(5) 0.2577(4) 0.4069(3) 0.0320(9) Uani 1 1 d . . .
C26 C 0.2649(5) 0.2734(4) 0.3191(3) 0.0376(10) Uani 1 1 d . . .
H26A H 0.2621 0.3530 0.3143 0.045 Uiso 1 1 calc R . .
C27 C 0.2766(5) 0.1708(4) 0.2382(3) 0.0364(10) Uani 1 1 d . . .
H27A H 0.2800 0.1806 0.1788 0.044 Uiso 1 1 calc R . .
C28 C 0.2406(6) 0.3660(4) 0.4938(3) 0.0408(10) Uani 1 1 d . . .
O1 O 0.8050(4) -0.1033(3) 0.35891(18) 0.0452(8) Uani 1 1 d . . .
C1 C 0.7813(5) -0.1032(4) 0.1254(3) 0.0320(9) Uani 1 1 d . . .
C2 C 0.7731(6) -0.1617(4) 0.0196(3) 0.0423(11) Uani 1 1 d . . .
H2A H 0.8837 -0.1208 -0.0010 0.051 Uiso 1 1 calc R . .
H2B H 0.6653 -0.1463 -0.0108 0.051 Uiso 1 1 calc R . .
C3 C 0.7608(12) -0.3037(5) -0.0116(4) 0.101(2) Uani 1 1 d D . .
H3A H 0.6304 -0.3466 -0.0320 0.121 Uiso 1 1 calc R . .
H3B H 0.8255 -0.3270 -0.0678 0.121 Uiso 1 1 calc R . .
C4 C 0.8287(12) -0.3564(5) 0.0522(4) 0.112(3) Uani 1 1 d D . .
H4A H 0.9611 -0.3488 0.0479 0.135 Uiso 1 1 calc R . .
H4B H 0.7708 -0.4478 0.0285 0.135 Uiso 1 1 calc R . .
C5 C 0.8061(6) -0.3059(4) 0.1549(3) 0.0383(10) Uani 1 1 d . . .
H5A H 0.9110 -0.3139 0.1925 0.046 Uiso 1 1 calc R . .
H5B H 0.6935 -0.3566 0.1667 0.046 Uiso 1 1 calc R . .
C6 C 0.7947(5) -0.1680(4) 0.1857(3) 0.0320(9) Uani 1 1 d . . .
C7 C 0.7937(5) -0.0794(4) 0.2848(3) 0.0335(9) Uani 1 1 d . . .
C8 C 0.7805(5) 0.0474(4) 0.2769(2) 0.0309(9) Uani 1 1 d . . .
C9 C 0.7752(5) 0.0317(3) 0.1799(2) 0.0297(9) Uani 1 1 d . . .
C10 C 0.7668(5) 0.1335(4) 0.1497(3) 0.0326(9) Uani 1 1 d . . .
H10A H 0.7635 0.1238 0.0852 0.039 Uiso 1 1 calc R . .
C11 C 0.7635(5) 0.2521(4) 0.2194(3) 0.0342(9) Uani 1 1 d . A .
C12 C 0.7677(6) 0.2666(4) 0.3156(3) 0.0390(10) Uani 1 1 d . . .
H12A H 0.7643 0.3460 0.3607 0.047 Uiso 1 1 calc R . .
C13 C 0.7770(5) 0.1632(4) 0.3450(3) 0.0355(10) Uani 1 1 d . . .
H13A H 0.7806 0.1725 0.4095 0.043 Uiso 1 1 calc R . .
C14 C 0.7619(6) 0.3652(4) 0.1906(3) 0.0444(11) Uani 1 1 d D . .
F1 F 0.9240(12) 0.4452(11) 0.2103(9) 0.093(5) Uani 0.50 1 d PDU A 1
F2 F 0.6387(16) 0.4290(11) 0.2287(9) 0.089(4) Uani 0.50 1 d PDU A 1
F3 F 0.7207(16) 0.3352(11) 0.0976(5) 0.067(3) Uani 0.50 1 d PDU A 1
F1' F 0.751(2) 0.4709(8) 0.2607(6) 0.082(4) Uani 0.50 1 d PDU A 2
F2' F 0.625(2) 0.3466(11) 0.1262(10) 0.123(5) Uani 0.50 1 d PDU A 2
F3' F 0.9137(15) 0.4038(14) 0.1566(11) 0.113(6) Uani 0.50 1 d PDU 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
F4 C28 1.313(5) . ?
F5 C28 1.323(5) . ?
F6 C28 1.328(5) . ?
O2 C21 1.212(4) . ?
C15 C20 1.347(5) . ?
C15 C23 1.473(5) . ?
C15 C16 1.493(5) . ?
C16 C17 1.528(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.508(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.528(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.487(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.494(5) . ?
C21 C22 1.500(5) . ?
C22 C27 1.361(5) . ?
C22 C23 1.414(5) . ?
C23 C24 1.372(5) . ?
C24 C25 1.408(5) . ?
C24 H24A 0.9300 . ?
C25 C26 1.382(5) . ?
C25 C28 1.485(5) . ?
C26 C27 1.386(5) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
O1 C7 1.225(4) . ?
C1 C6 1.348(5) . ?
C1 C9 1.480(5) . ?
C1 C2 1.487(5) . ?
C2 C3 1.496(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.401(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.476(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.490(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.484(5) . ?
C7 C8 1.498(5) . ?
C8 C13 1.368(5) . ?
C8 C9 1.397(5) . ?
C9 C10 1.378(5) . ?
C10 C11 1.401(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.387(5) . ?
C11 C14 1.480(5) . ?
C12 C13 1.390(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 F2' 1.295(8) . ?
C14 F1 1.301(7) . ?
C14 F2 1.305(7) . ?
C14 F3' 1.306(8) . ?
C14 F1' 1.318(7) . ?
C14 F3 1.318(7) . ?

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
C20 C15 C23 110.7(3) . . ?
C20 C15 C16 123.7(4) . . ?
C23 C15 C16 125.6(3) . . ?
C15 C16 C17 110.6(3) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 112.2(3) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C19 112.0(4) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C18 110.1(3) . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?
C15 C20 C19 124.8(3) . . ?
C15 C20 C21 108.3(3) . . ?
C19 C20 C21 126.9(3) . . ?
O2 C21 C20 127.3(4) . . ?
O2 C21 C22 126.6(4) . . ?
C20 C21 C22 106.1(3) . . ?
C27 C22 C23 121.4(3) . . ?
C27 C22 C21 132.0(3) . . ?
C23 C22 C21 106.7(3) . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 C15 131.7(3) . . ?
C22 C23 C15 108.2(3) . . ?
C23 C24 C25 118.0(3) . . ?
C23 C24 H24A 121.0 . . ?
C25 C24 H24A 121.0 . . ?
C26 C25 C24 121.4(4) . . ?
C26 C25 C28 120.7(4) . . ?
C24 C25 C28 117.9(3) . . ?
C25 C26 C27 120.1(4) . . ?
C25 C26 H26A 119.9 . . ?
C27 C26 H26A 119.9 . . ?
C22 C27 C26 119.1(3) . . ?
C22 C27 H27A 120.5 . . ?
C26 C27 H27A 120.5 . . ?
F4 C28 F5 105.9(4) . . ?
F4 C28 F6 106.1(3) . . ?
F5 C28 F6 105.0(4) . . ?
F4 C28 C25 113.0(3) . . ?
F5 C28 C25 113.5(3) . . ?
F6 C28 C25 112.6(3) . . ?
C6 C1 C9 110.1(3) . . ?
C6 C1 C2 123.9(4) . . ?
C9 C1 C2 126.0(3) . . ?
C1 C2 C3 111.3(3) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3A 107.3 . . ?
C2 C3 H3A 107.3 . . ?
C4 C3 H3B 107.3 . . ?
C2 C3 H3B 107.3 . . ?
H3A C3 H3B 106.9 . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 H4A 107.2 . . ?
C5 C4 H4A 107.2 . . ?
C3 C4 H4B 107.2 . . ?
C5 C4 H4B 107.2 . . ?
H4A C4 H4B 106.8 . . ?
C4 C5 C6 111.1(3) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C1 C6 C7 108.4(3) . . ?
C1 C6 C5 124.3(3) . . ?
C7 C6 C5 127.3(3) . . ?
O1 C7 C6 127.4(4) . . ?
O1 C7 C8 126.4(3) . . ?
C6 C7 C8 106.2(3) . . ?
C13 C8 C9 121.5(3) . . ?
C13 C8 C7 131.6(3) . . ?
C9 C8 C7 106.9(3) . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 C1 131.0(3) . . ?
C8 C9 C1 108.3(3) . . ?
C9 C10 C11 117.8(3) . . ?
C9 C10 H10A 121.1 . . ?
C11 C10 H10A 121.1 . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 C14 119.3(3) . . ?
C10 C11 C14 119.5(3) . . ?
C11 C12 C13 120.4(4) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C8 C13 C12 118.4(3) . . ?
C8 C13 H13A 120.8 . . ?
C12 C13 H13A 120.8 . . ?
F2' C14 F1 129.5(9) . . ?
F2' C14 F2 69.8(7) . . ?
F1 C14 F2 108.5(7) . . ?
F2' C14 F3' 106.1(8) . . ?
F1 C14 F3' 34.4(6) . . ?
F2 C14 F3' 129.5(8) . . ?
F2' C14 F1' 104.8(7) . . ?
F1 C14 F1' 71.9(7) . . ?
F2 C14 F1' 39.7(5) . . ?
F3' C14 F1' 102.2(7) . . ?
F2' C14 F3 38.0(7) . . ?
F1 C14 F3 103.8(7) . . ?
F2 C14 F3 104.4(7) . . ?
F3' C14 F3 72.2(7) . . ?
F1' C14 F3 128.5(7) . . ?
F2' C14 C11 113.7(6) . . ?
F1 C14 C11 112.6(7) . . ?
F2 C14 C11 113.2(6) . . ?
F3' C14 C11 113.8(7) . . ?
F1' C14 C11 115.0(5) . . ?
F3 C14 C11 113.6(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
C20 C15 C16 C17 -12.9(6) . . . . ?
C23 C15 C16 C17 167.4(4) . . . . ?
C15 C16 C17 C18 43.0(5) . . . . ?
C16 C17 C18 C19 -61.1(5) . . . . ?
C17 C18 C19 C20 44.4(5) . . . . ?
C23 C15 C20 C19 178.5(3) . . . . ?
C16 C15 C20 C19 -1.2(6) . . . . ?
C23 C15 C20 C21 -1.3(4) . . . . ?
C16 C15 C20 C21 179.0(3) . . . . ?
C18 C19 C20 C15 -14.5(5) . . . . ?
C18 C19 C20 C21 165.3(4) . . . . ?
C15 C20 C21 O2 -179.3(4) . . . . ?
C19 C20 C21 O2 0.8(6) . . . . ?
C15 C20 C21 C22 1.6(4) . . . . ?
C19 C20 C21 C22 -178.3(3) . . . . ?
O2 C21 C22 C27 0.4(7) . . . . ?
C20 C21 C22 C27 179.5(4) . . . . ?
O2 C21 C22 C23 179.7(4) . . . . ?
C20 C21 C22 C23 -1.2(4) . . . . ?
C27 C22 C23 C24 0.2(6) . . . . ?
C21 C22 C23 C24 -179.1(3) . . . . ?
C27 C22 C23 C15 179.9(3) . . . . ?
C21 C22 C23 C15 0.5(4) . . . . ?
C20 C15 C23 C24 -179.9(4) . . . . ?
C16 C15 C23 C24 -0.2(6) . . . . ?
C20 C15 C23 C22 0.5(4) . . . . ?
C16 C15 C23 C22 -179.8(4) . . . . ?
C22 C23 C24 C25 -0.5(5) . . . . ?
C15 C23 C24 C25 180.0(4) . . . . ?
C23 C24 C25 C26 0.0(5) . . . . ?
C23 C24 C25 C28 179.4(3) . . . . ?
C24 C25 C26 C27 0.7(6) . . . . ?
C28 C25 C26 C27 -178.7(4) . . . . ?
C23 C22 C27 C26 0.5(6) . . . . ?
C21 C22 C27 C26 179.7(4) . . . . ?
C25 C26 C27 C22 -0.9(6) . . . . ?
C26 C25 C28 F4 128.6(4) . . . . ?
C24 C25 C28 F4 -50.7(5) . . . . ?
C26 C25 C28 F5 8.0(5) . . . . ?
C24 C25 C28 F5 -171.4(4) . . . . ?
C26 C25 C28 F6 -111.2(4) . . . . ?
C24 C25 C28 F6 69.5(4) . . . . ?
C6 C1 C2 C3 6.2(6) . . . . ?
C9 C1 C2 C3 -173.5(5) . . . . ?
C1 C2 C3 C4 -24.8(9) . . . . ?
C2 C3 C4 C5 37.5(11) . . . . ?
C3 C4 C5 C6 -27.2(9) . . . . ?
C9 C1 C6 C7 1.3(4) . . . . ?
C2 C1 C6 C7 -178.4(3) . . . . ?
C9 C1 C6 C5 -179.3(3) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
C4 C5 C6 C1 8.4(6) . . . . ?
C4 C5 C6 C7 -172.4(5) . . . . ?
C1 C6 C7 O1 -179.4(4) . . . . ?
C5 C6 C7 O1 1.3(6) . . . . ?
C1 C6 C7 C8 -0.7(4) . . . . ?
C5 C6 C7 C8 179.9(4) . . . . ?
O1 C7 C8 C13 -0.3(7) . . . . ?
C6 C7 C8 C13 -179.0(4) . . . . ?
O1 C7 C8 C9 178.5(4) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C13 C8 C9 C10 0.3(6) . . . . ?
C7 C8 C9 C10 -178.7(3) . . . . ?
C13 C8 C9 C1 179.9(3) . . . . ?
C7 C8 C9 C1 1.0(4) . . . . ?
C6 C1 C9 C10 178.1(4) . . . . ?
C2 C1 C9 C10 -2.2(7) . . . . ?
C6 C1 C9 C8 -1.5(4) . . . . ?
C2 C1 C9 C8 178.2(4) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C1 C9 C10 C11 -179.7(4) . . . . ?
C9 C10 C11 C12 -0.3(6) . . . . ?
C9 C10 C11 C14 177.7(4) . . . . ?
C10 C11 C12 C13 0.6(6) . . . . ?
C14 C11 C12 C13 -177.4(4) . . . . ?
C9 C8 C13 C12 0.0(6) . . . . ?
C7 C8 C13 C12 178.6(4) . . . . ?
C11 C12 C13 C8 -0.4(6) . . . . ?
C12 C11 C14 F2' -125.6(10) . . . . ?
C10 C11 C14 F2' 56.5(10) . . . . ?
C12 C11 C14 F1 75.1(8) . . . . ?
C10 C11 C14 F1 -102.9(8) . . . . ?
C12 C11 C14 F2 -48.4(8) . . . . ?
C10 C11 C14 F2 133.6(8) . . . . ?
C12 C11 C14 F3' 112.7(9) . . . . ?
C10 C11 C14 F3' -65.3(9) . . . . ?
C12 C11 C14 F1' -4.7(9) . . . . ?
C10 C11 C14 F1' 177.3(8) . . . . ?
C12 C11 C14 F3 -167.2(6) . . . . ?
C10 C11 C14 F3 14.8(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1437984'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 O3'
_chemical_formula_weight         228.24

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/c

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

_cell_length_a                   15.9874(7)
_cell_length_b                   10.2887(4)
_cell_length_c                   13.7969(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.2800(10)
_cell_angle_gamma                90.00
_cell_volume                     2154.92(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_T_max  0.9738
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24671
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3797
_reflns_number_gt                2831
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0468P)²+2.0114P] 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_number_reflns         3797
_refine_ls_number_parameters     307
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.024
_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
O1 O 0.35699(10) 1.38971(15) 0.29278(13) 0.0417(4) Uani 1 1 d . . .
O2 O 0.44246(11) 0.77557(15) 0.33371(14) 0.0446(4) Uani 1 1 d . . .
O3 O 0.30299(10) 0.85306(15) 0.25219(13) 0.0421(4) Uani 1 1 d . . .
O4 O 0.12441(10) 0.11305(15) 0.15844(13) 0.0405(4) Uani 1 1 d . . .
O5 O 0.16274(11) 0.65199(16) 0.18341(16) 0.0512(5) Uani 1 1 d . . .
O6 O 0.01769(12) 0.71860(16) 0.13439(16) 0.0519(5) Uani 1 1 d . . .
C1 C 0.55217(17) 1.4768(2) 0.3983(2) 0.0471(6) Uani 1 1 d U . .
H1A H 0.5141 1.5351 0.4231 0.057 Uiso 1 1 calc R . .
H1B H 0.5585 1.5142 0.3348 0.057 Uiso 1 1 calc R . .
C2 C 0.6427(2) 1.4640(4) 0.4792(4) 0.1085(16) Uani 1 1 d U . .
H2A H 0.6775 1.5417 0.4738 0.130 Uiso 1 1 calc R . .
H2B H 0.6336 1.4677 0.5469 0.130 Uiso 1 1 calc R . .
C3 C 0.6945(2) 1.3550(3) 0.4785(3) 0.0878(12) Uani 1 1 d U . .
H3A H 0.7436 1.3540 0.5436 0.105 Uiso 1 1 calc R . .
H3B H 0.7209 1.3667 0.4231 0.105 Uiso 1 1 calc R . .
C4 C 0.65194(15) 1.2251(3) 0.46535(19) 0.0446(6) Uani 1 1 d . . .
H4A H 0.6589 1.1868 0.5333 0.053 Uiso 1 1 calc R . .
H4B H 0.6816 1.1671 0.4292 0.053 Uiso 1 1 calc R . .
C5 C 0.55616(14) 1.2333(2) 0.40628(17) 0.0331(5) Uani 1 1 d . . .
C6 C 0.51198(14) 1.3445(2) 0.37769(17) 0.0341(5) Uani 1 1 d . . .
C7 C 0.41750(14) 1.3127(2) 0.32519(17) 0.0323(5) Uani 1 1 d . . .
C8 C 0.41181(13) 1.1679(2) 0.32235(16) 0.0292(5) Uani 1 1 d . . .
C9 C 0.49645(13) 1.1203(2) 0.37245(16) 0.0304(5) Uani 1 1 d . . .
C10 C 0.51402(15) 0.9884(2) 0.38235(17) 0.0348(5) Uani 1 1 d . . .
H10A H 0.5708 0.9551 0.4180 0.042 Uiso 1 1 calc R . .
C11 C 0.44324(15) 0.9087(2) 0.33675(17) 0.0338(5) Uani 1 1 d . . .
C12 C 0.35991(14) 0.9563(2) 0.28709(17) 0.0320(5) Uani 1 1 d . . .
C13 C 0.34053(14) 1.0871(2) 0.27888(17) 0.0312(5) Uani 1 1 d . . .
H13A H 0.2829 1.1194 0.2460 0.037 Uiso 1 1 calc R . .
C14 C 0.36035(18) 0.7444(2) 0.2577(2) 0.0481(7) Uani 1 1 d . . .
H14A H 0.3694 0.7296 0.1908 0.058 Uiso 1 1 calc R . .
H14B H 0.3347 0.6647 0.2771 0.058 Uiso 1 1 calc R . .
C15 C -0.06781(15) 0.0098(2) 0.1001(2) 0.0392(6) Uani 1 1 d . . .
H15A H -0.0329 -0.0431 0.1588 0.047 Uiso 1 1 calc R . .
H15B H -0.0617 -0.0291 0.0370 0.047 Uiso 1 1 calc R . .
C16 C -0.16475(17) 0.0088(3) 0.0952(2) 0.0516(7) Uani 1 1 d . . .
H16A H -0.1909 -0.0765 0.0694 0.062 Uiso 1 1 calc R . .
H16B H -0.1687 0.0203 0.1649 0.062 Uiso 1 1 calc R . .
C17 C -0.21671(16) 0.1150(3) 0.0269(2) 0.0499(7) Uani 1 1 d . . .
H17A H -0.2789 0.1097 0.0256 0.060 Uiso 1 1 calc R . .
H17B H -0.2153 0.1003 -0.0435 0.060 Uiso 1 1 calc R . .
C18 C -0.18176(15) 0.2511(2) 0.0611(2) 0.0417(6) Uani 1 1 d . . .
H18A H -0.2046 0.3127 0.0038 0.050 Uiso 1 1 calc R . .
H18B H -0.2029 0.2796 0.1179 0.050 Uiso 1 1 calc R . .
C19 C -0.08343(14) 0.2526(2) 0.09523(17) 0.0317(5) Uani 1 1 d . . .
C20 C -0.03365(14) 0.1457(2) 0.11137(17) 0.0322(5) Uani 1 1 d . . .
C21 C 0.06087(14) 0.1854(2) 0.14162(17) 0.0308(5) Uani 1 1 d . . .
C22 C 0.06146(13) 0.3299(2) 0.14481(16) 0.0293(5) Uani 1 1 d . . .
C23 C -0.02655(13) 0.3703(2) 0.11527(17) 0.0308(5) Uani 1 1 d . . .
C24 C -0.04913(15) 0.5008(2) 0.10896(18) 0.0364(5) Uani 1 1 d . . .
H24A H -0.1086 0.5297 0.0884 0.044 Uiso 1 1 calc R . .
C25 C 0.02128(15) 0.5856(2) 0.13490(19) 0.0366(6) Uani 1 1 d . . .
C26 C 0.10790(15) 0.5450(2) 0.16473(19) 0.0363(5) Uani 1 1 d . . .
C27 C 0.13157(14) 0.4161(2) 0.17062(18) 0.0325(5) Uani 1 1 d . . .
H27A H 0.1912 0.3883 0.1908 0.039 Uiso 1 1 calc R . .
C28 C 0.10614(18) 0.7593(2) 0.1851(3) 0.0543(8) Uani 1 1 d . . .
H28A H 0.1129 0.7845 0.2564 0.065 Uiso 1 1 calc R . .
H28B H 0.1212 0.8351 0.1497 0.065 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
O1 C7 1.222(3) . ?
O2 C11 1.370(3) . ?
O2 C14 1.436(3) . ?
O3 C12 1.383(3) . ?
O3 C14 1.433(3) . ?
O4 C21 1.222(3) . ?
O5 C26 1.381(3) . ?
O5 C28 1.432(3) . ?
O6 C25 1.370(3) . ?
O6 C28 1.430(3) . ?
C1 C6 1.494(3) . ?
C1 C2 1.532(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.396(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.485(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.494(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.337(3) . ?
C5 C9 1.484(3) . ?
C6 C7 1.492(3) . ?
C7 C8 1.492(3) . ?
C8 C13 1.386(3) . ?
C8 C9 1.401(3) . ?
C9 C10 1.384(3) . ?
C10 C11 1.379(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.382(3) . ?
C12 C13 1.378(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C20 1.492(3) . ?
C15 C16 1.530(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.510(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.526(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.493(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.334(3) . ?
C19 C23 1.487(3) . ?
C20 C21 1.493(3) . ?
C21 C22 1.487(3) . ?
C22 C27 1.385(3) . ?
C22 C23 1.400(3) . ?
C23 C24 1.386(3) . ?
C24 C25 1.379(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.380(3) . ?
C26 C27 1.374(3) . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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 C14 104.07(18) . . ?
C12 O3 C14 103.91(17) . . ?
C26 O5 C28 104.51(18) . . ?
C25 O6 C28 104.88(19) . . ?
C6 C1 C2 108.2(2) . . ?
C6 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
C6 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2A 107.5 . . ?
C1 C2 H2A 107.5 . . ?
C3 C2 H2B 107.5 . . ?
C1 C2 H2B 107.5 . . ?
H2A C2 H2B 107.0 . . ?
C2 C3 C4 118.3(3) . . ?
C2 C3 H3A 107.7 . . ?
C4 C3 H3A 107.7 . . ?
C2 C3 H3B 107.7 . . ?
C4 C3 H3B 107.7 . . ?
H3A C3 H3B 107.1 . . ?
C3 C4 C5 111.6(2) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C9 110.44(19) . . ?
C6 C5 C4 124.4(2) . . ?
C9 C5 C4 125.1(2) . . ?
C5 C6 C7 108.5(2) . . ?
C5 C6 C1 124.6(2) . . ?
C7 C6 C1 127.0(2) . . ?
O1 C7 C8 127.1(2) . . ?
O1 C7 C6 126.9(2) . . ?
C8 C7 C6 105.99(18) . . ?
C13 C8 C9 122.6(2) . . ?
C13 C8 C7 130.2(2) . . ?
C9 C8 C7 107.15(19) . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 C5 130.3(2) . . ?
C8 C9 C5 107.92(19) . . ?
C11 C10 C9 115.2(2) . . ?
C11 C10 H10A 122.4 . . ?
C9 C10 H10A 122.4 . . ?
O2 C11 C10 127.3(2) . . ?
O2 C11 C12 109.9(2) . . ?
C10 C11 C12 122.8(2) . . ?
C13 C12 C11 122.9(2) . . ?
C13 C12 O3 128.0(2) . . ?
C11 C12 O3 109.11(19) . . ?
C12 C13 C8 114.7(2) . . ?
C12 C13 H13A 122.7 . . ?
C8 C13 H13A 122.7 . . ?
O3 C14 O2 106.73(18) . . ?
O3 C14 H14A 110.4 . . ?
O2 C14 H14A 110.4 . . ?
O3 C14 H14B 110.4 . . ?
O2 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C20 C15 C16 110.1(2) . . ?
C20 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C20 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 112.0(2) . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 113.2(2) . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 110.8(2) . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 C23 110.01(19) . . ?
C20 C19 C18 123.9(2) . . ?
C23 C19 C18 126.1(2) . . ?
C19 C20 C15 125.1(2) . . ?
C19 C20 C21 108.64(19) . . ?
C15 C20 C21 126.22(19) . . ?
O4 C21 C22 127.3(2) . . ?
O4 C21 C20 126.5(2) . . ?
C22 C21 C20 106.15(18) . . ?
C27 C22 C23 122.9(2) . . ?
C27 C22 C21 130.13(19) . . ?
C23 C22 C21 106.97(18) . . ?
C24 C23 C22 121.6(2) . . ?
C24 C23 C19 130.2(2) . . ?
C22 C23 C19 108.20(18) . . ?
C25 C24 C23 114.9(2) . . ?
C25 C24 H24A 122.6 . . ?
C23 C24 H24A 122.6 . . ?
O6 C25 C24 126.9(2) . . ?
O6 C25 C26 109.9(2) . . ?
C24 C25 C26 123.2(2) . . ?
C27 C26 C25 122.8(2) . . ?
C27 C26 O5 127.7(2) . . ?
C25 C26 O5 109.5(2) . . ?
C26 C27 C22 114.6(2) . . ?
C26 C27 H27A 122.7 . . ?
C22 C27 H27A 122.7 . . ?
O6 C28 O5 107.40(19) . . ?
O6 C28 H28A 110.2 . . ?
O5 C28 H28A 110.2 . . ?
O6 C28 H28B 110.2 . . ?
O5 C28 H28B 110.2 . . ?
H28A C28 H28B 108.5 . . ?

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
C6 C1 C2 C3 36.4(5) . . . . ?
C1 C2 C3 C4 -45.6(6) . . . . ?
C2 C3 C4 C5 27.8(5) . . . . ?
C3 C4 C5 C6 -6.4(4) . . . . ?
C3 C4 C5 C9 174.6(3) . . . . ?
C9 C5 C6 C7 2.0(3) . . . . ?
C4 C5 C6 C7 -177.1(2) . . . . ?
C9 C5 C6 C1 -179.3(2) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C2 C1 C6 C5 -14.7(4) . . . . ?
C2 C1 C6 C7 163.7(3) . . . . ?
C5 C6 C7 O1 176.6(2) . . . . ?
C1 C6 C7 O1 -2.1(4) . . . . ?
C5 C6 C7 C8 -2.3(3) . . . . ?
C1 C6 C7 C8 179.0(2) . . . . ?
O1 C7 C8 C13 4.1(4) . . . . ?
C6 C7 C8 C13 -177.1(2) . . . . ?
O1 C7 C8 C9 -177.2(2) . . . . ?
C6 C7 C8 C9 1.7(2) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 -179.4(2) . . . . ?
C13 C8 C9 C5 178.3(2) . . . . ?
C7 C8 C9 C5 -0.6(2) . . . . ?
C6 C5 C9 C10 177.8(2) . . . . ?
C4 C5 C9 C10 -3.1(4) . . . . ?
C6 C5 C9 C8 -0.9(3) . . . . ?
C4 C5 C9 C8 178.2(2) . . . . ?
C8 C9 C10 C11 2.0(3) . . . . ?
C5 C9 C10 C11 -176.5(2) . . . . ?
C14 O2 C11 C10 -166.5(2) . . . . ?
C14 O2 C11 C12 14.3(3) . . . . ?
C9 C10 C11 O2 179.1(2) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
O2 C11 C12 C13 179.3(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
O2 C11 C12 O3 1.0(3) . . . . ?
C10 C11 C12 O3 -178.3(2) . . . . ?
C14 O3 C12 C13 165.9(2) . . . . ?
C14 O3 C12 C11 -15.8(2) . . . . ?
C11 C12 C13 C8 1.5(3) . . . . ?
O3 C12 C13 C8 179.5(2) . . . . ?
C9 C8 C13 C12 -1.2(3) . . . . ?
C7 C8 C13 C12 177.3(2) . . . . ?
C12 O3 C14 O2 24.5(2) . . . . ?
C11 O2 C14 O3 -24.0(3) . . . . ?
C20 C15 C16 C17 43.7(3) . . . . ?
C15 C16 C17 C18 -59.3(3) . . . . ?
C16 C17 C18 C19 41.1(3) . . . . ?
C17 C18 C19 C20 -11.5(3) . . . . ?
C17 C18 C19 C23 167.9(2) . . . . ?
C23 C19 C20 C15 179.2(2) . . . . ?
C18 C19 C20 C15 -1.3(4) . . . . ?
C23 C19 C20 C21 -1.1(3) . . . . ?
C18 C19 C20 C21 178.3(2) . . . . ?
C16 C15 C20 C19 -14.8(3) . . . . ?
C16 C15 C20 C21 165.5(2) . . . . ?
C19 C20 C21 O4 -177.0(2) . . . . ?
C15 C20 C21 O4 2.6(4) . . . . ?
C19 C20 C21 C22 1.8(3) . . . . ?
C15 C20 C21 C22 -178.5(2) . . . . ?
O4 C21 C22 C27 -2.8(4) . . . . ?
C20 C21 C22 C27 178.4(2) . . . . ?
O4 C21 C22 C23 177.1(2) . . . . ?
C20 C21 C22 C23 -1.8(2) . . . . ?
C27 C22 C23 C24 0.7(4) . . . . ?
C21 C22 C23 C24 -179.2(2) . . . . ?
C27 C22 C23 C19 -179.0(2) . . . . ?
C21 C22 C23 C19 1.1(2) . . . . ?
C20 C19 C23 C24 -179.6(2) . . . . ?
C18 C19 C23 C24 0.9(4) . . . . ?
C20 C19 C23 C22 0.0(3) . . . . ?
C18 C19 C23 C22 -179.5(2) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C19 C23 C24 C25 178.9(2) . . . . ?
C28 O6 C25 C24 169.3(3) . . . . ?
C28 O6 C25 C26 -11.4(3) . . . . ?
C23 C24 C25 O6 179.3(2) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
O6 C25 C26 C27 -178.9(2) . . . . ?
C24 C25 C26 C27 0.4(4) . . . . ?
O6 C25 C26 O5 -0.6(3) . . . . ?
C24 C25 C26 O5 178.7(2) . . . . ?
C28 O5 C26 C27 -169.5(3) . . . . ?
C28 O5 C26 C25 12.2(3) . . . . ?
C25 C26 C27 C22 -0.4(4) . . . . ?
O5 C26 C27 C22 -178.4(2) . . . . ?
C23 C22 C27 C26 -0.1(3) . . . . ?
C21 C22 C27 C26 179.7(2) . . . . ?
C25 O6 C28 O5 18.9(3) . . . . ?
C26 O5 C28 O6 -19.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1437985'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3-fluoro-6,7,8,9-tetrahydrobenzo[a]azulen-10(5H)-one
_chemical_name_common            no
_chemical_melting_point          'no information'
_chemical_formula_moiety         'C14 H13 F O'
_chemical_formula_sum            'C14 H13 F O'
_chemical_formula_weight         216.24

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'
F F 0.0171 0.0103 '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   Pbca

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'
'-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                   34.01(5)
_cell_length_b                   9.158(13)
_cell_length_c                   7.196(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2241(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14218
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.20
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1975
_reflns_number_gt                1157
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          'no information'

_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)+(0.0583P)²+0.5176P] 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     SHELXL
_refine_ls_extinction_coef       0.0019(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1975
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
F1 F -0.01267(4) 0.2430(2) 0.1346(3) 0.0981(7) Uani 1 1 d . . .
O1 O 0.17015(5) 0.04410(19) 0.1844(2) 0.0604(5) Uani 1 1 d . . .
C1 C 0.12803(7) 0.3921(3) 0.1482(3) 0.0461(6) Uani 1 1 d . . .
C2 C 0.12488(8) 0.5553(3) 0.1300(4) 0.0617(7) Uani 1 1 d . . .
H2A H 0.0988 0.5843 0.1694 0.074 Uiso 1 1 calc R . .
H2B H 0.1274 0.5802 -0.0005 0.074 Uiso 1 1 calc R . .
C3 C 0.15468(7) 0.6451(3) 0.2384(4) 0.0601(8) Uani 1 1 d . . .
H3A H 0.1522 0.6205 0.3690 0.072 Uiso 1 1 calc R . .
H3B H 0.1479 0.7475 0.2253 0.072 Uiso 1 1 calc R . .
C4 C 0.19763(8) 0.6260(3) 0.1820(4) 0.0700(8) Uani 1 1 d . . .
H4A H 0.1993 0.6334 0.0478 0.084 Uiso 1 1 calc R . .
H4B H 0.2126 0.7064 0.2339 0.084 Uiso 1 1 calc R . .
C5 C 0.21707(8) 0.4835(3) 0.2415(4) 0.0653(8) Uani 1 1 d . . .
H5A H 0.2452 0.4931 0.2247 0.078 Uiso 1 1 calc R . .
H5B H 0.2123 0.4692 0.3731 0.078 Uiso 1 1 calc R . .
C6 C 0.20345(7) 0.3487(3) 0.1388(4) 0.0577(7) Uani 1 1 d . . .
H6A H 0.2094 0.3619 0.0081 0.069 Uiso 1 1 calc R . .
H6B H 0.2190 0.2667 0.1824 0.069 Uiso 1 1 calc R . .
C7 C 0.16080(7) 0.3077(2) 0.1547(3) 0.0467(6) Uani 1 1 d . . .
C8 C 0.14845(7) 0.1506(3) 0.1693(3) 0.0455(6) Uani 1 1 d . . .
C9 C 0.10464(7) 0.1490(2) 0.1635(3) 0.0446(6) Uani 1 1 d . . .
C10 C 0.09237(6) 0.2951(2) 0.1523(3) 0.0446(6) Uani 1 1 d . . .
C11 C 0.05289(7) 0.3292(3) 0.1421(3) 0.0556(7) Uani 1 1 d . . .
H11A H 0.0441 0.4252 0.1335 0.067 Uiso 1 1 calc R . .
C12 C 0.02669(7) 0.2107(3) 0.1454(4) 0.0618(8) Uani 1 1 d . . .
C13 C 0.03797(8) 0.0679(3) 0.1563(4) 0.0640(8) Uani 1 1 d . . .
H13A H 0.0193 -0.0062 0.1574 0.077 Uiso 1 1 calc R . .
C14 C 0.07796(8) 0.0348(3) 0.1658(3) 0.0566(7) Uani 1 1 d . . .
H14A H 0.0865 -0.0615 0.1735 0.068 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
F1 C12 1.373(3) . ?
O1 C8 1.228(3) . ?
C1 C7 1.357(3) . ?
C1 C2 1.503(4) . ?
C1 C10 1.504(3) . ?
C2 C3 1.521(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.526(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.524(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.511(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.503(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.502(4) . ?
C8 C9 1.491(4) . ?
C9 C14 1.385(3) . ?
C9 C10 1.404(4) . ?
C10 C11 1.381(4) . ?
C11 C12 1.404(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.365(4) . ?
C13 C14 1.395(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 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
C7 C1 C2 128.9(2) . . ?
C7 C1 C10 109.0(2) . . ?
C2 C1 C10 122.1(2) . . ?
C1 C2 C3 116.4(2) . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
C3 C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?
C2 C3 C4 116.0(2) . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C5 C4 C3 116.0(2) . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
C3 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C6 C5 C4 115.4(2) . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C7 C6 C5 117.6(2) . . ?
C7 C6 H6A 107.9 . . ?
C5 C6 H6A 107.9 . . ?
C7 C6 H6B 107.9 . . ?
C5 C6 H6B 107.9 . . ?
H6A C6 H6B 107.2 . . ?
C1 C7 C8 108.6(2) . . ?
C1 C7 C6 130.3(2) . . ?
C8 C7 C6 121.0(2) . . ?
O1 C8 C9 126.6(2) . . ?
O1 C8 C7 126.8(2) . . ?
C9 C8 C7 106.7(2) . . ?
C14 C9 C10 121.7(2) . . ?
C14 C9 C8 131.5(2) . . ?
C10 C9 C8 106.83(19) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 C1 130.5(2) . . ?
C9 C10 C1 108.9(2) . . ?
C10 C11 C12 116.2(3) . . ?
C10 C11 H11A 121.9 . . ?
C12 C11 H11A 121.9 . . ?
C13 C12 F1 118.9(2) . . ?
C13 C12 C11 124.3(3) . . ?
F1 C12 C11 116.8(3) . . ?
C12 C13 C14 119.0(2) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C9 C14 C13 118.3(3) . . ?
C9 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?

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
C7 C1 C2 C3 -39.8(4) . . . . ?
C10 C1 C2 C3 143.6(2) . . . . ?
C1 C2 C3 C4 63.9(3) . . . . ?
C2 C3 C4 C5 -74.0(3) . . . . ?
C3 C4 C5 C6 71.5(3) . . . . ?
C4 C5 C6 C7 -61.5(3) . . . . ?
C2 C1 C7 C8 -178.7(2) . . . . ?
C10 C1 C7 C8 -1.7(3) . . . . ?
C2 C1 C7 C6 -2.5(4) . . . . ?
C10 C1 C7 C6 174.5(2) . . . . ?
C5 C6 C7 C1 42.6(4) . . . . ?
C5 C6 C7 C8 -141.6(2) . . . . ?
C1 C7 C8 O1 -177.4(2) . . . . ?
C6 C7 C8 O1 6.0(4) . . . . ?
C1 C7 C8 C9 2.2(3) . . . . ?
C6 C7 C8 C9 -174.4(2) . . . . ?
O1 C8 C9 C14 -2.8(4) . . . . ?
C7 C8 C9 C14 177.7(2) . . . . ?
O1 C8 C9 C10 177.8(2) . . . . ?
C7 C8 C9 C10 -1.7(2) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C8 C9 C10 C11 179.1(2) . . . . ?
C14 C9 C10 C1 -178.7(2) . . . . ?
C8 C9 C10 C1 0.7(2) . . . . ?
C7 C1 C10 C11 -177.5(2) . . . . ?
C2 C1 C10 C11 -0.2(4) . . . . ?
C7 C1 C10 C9 0.6(3) . . . . ?
C2 C1 C10 C9 177.9(2) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C1 C10 C11 C12 178.5(2) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C10 C11 C12 F1 -179.8(2) . . . . ?
F1 C12 C13 C14 179.5(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C8 C9 C14 C13 -179.2(2) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.033
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane-ethyl acetate'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       'no information'
