# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_130703a
_database_code_depnum_ccdc_archive 'CCDC 1061550'
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2016-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
7a-methyl-2-phenyl-2-(trifluoromethyl)-3a,4-dihydrobenzo[d][1,3]dioxol-5(7aH)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 F3 O3'
_chemical_formula_weight         298.25

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   28.78(3)
_cell_length_b                   6.621(7)
_cell_length_c                   15.245(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.775(15)
_cell_angle_gamma                90.00
_cell_volume                     2782(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2415
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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  'Rigaku Mercury375R'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11489
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2448
_reflns_number_gt                1663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_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)+(0.0712P)²+0.5709P] 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       0.0005(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2448
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1499
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.20423(10) 0.2269(5) 0.8616(2) 0.0652(8) Uani 1 1 d . . .
C2 C 0.15774(9) 0.2492(3) 0.78205(16) 0.0479(6) Uani 1 1 d . . .
C3 C 0.11374(9) 0.1870(3) 0.80988(15) 0.0479(6) Uani 1 1 d . . .
C4 C 0.10135(10) -0.0139(4) 0.81279(19) 0.0630(7) Uani 1 1 d . . .
H4 H 0.1201 -0.1138 0.7968 0.076 Uiso 1 1 calc R . .
C5 C 0.06091(12) -0.0660(5) 0.8397(2) 0.0744(8) Uani 1 1 d . . .
H5 H 0.0527 -0.2015 0.8416 0.089 Uiso 1 1 calc R . .
C6 C 0.03296(11) 0.0777(5) 0.8632(2) 0.0726(8) Uani 1 1 d . . .
H6 H 0.0059 0.0409 0.8813 0.087 Uiso 1 1 calc R . .
C7 C 0.04491(11) 0.2758(5) 0.8601(2) 0.0719(8) Uani 1 1 d . . .
H7 H 0.0257 0.3746 0.8756 0.086 Uiso 1 1 calc R . .
C8 C 0.08505(10) 0.3316(4) 0.83447(18) 0.0622(7) Uani 1 1 d . . .
H8 H 0.0930 0.4675 0.8336 0.075 Uiso 1 1 calc R . .
C9 C 0.16502(9) 0.4654(4) 0.66827(17) 0.0526(6) Uani 1 1 d . . .
H9 H 0.1997 0.4925 0.6786 0.063 Uiso 1 1 calc R . .
C10 C 0.13512(10) 0.6342(4) 0.61373(19) 0.0593(7) Uani 1 1 d . . .
H10A H 0.1415 0.7575 0.6496 0.071 Uiso 1 1 calc R . .
H10B H 0.1448 0.6562 0.5586 0.071 Uiso 1 1 calc R . .
C11 C 0.08156(10) 0.5891(4) 0.58763(17) 0.0581(7) Uani 1 1 d . . .
C12 C 0.06777(10) 0.3796(4) 0.56361(18) 0.0576(7) Uani 1 1 d . . .
H12 H 0.0354 0.3503 0.5343 0.069 Uiso 1 1 calc R . .
C13 C 0.09943(10) 0.2305(4) 0.58195(17) 0.0536(6) Uani 1 1 d . . .
H13 H 0.0880 0.1007 0.5649 0.064 Uiso 1 1 calc R . .
C14 C 0.15248(9) 0.2555(3) 0.62826(16) 0.0474(6) Uani 1 1 d . . .
C15 C 0.18275(12) 0.1870(4) 0.5678(2) 0.0719(8) Uani 1 1 d . . .
H15A H 0.2165 0.1918 0.6017 0.108 Uiso 1 1 calc R . .
H15B H 0.1770 0.2744 0.5155 0.108 Uiso 1 1 calc R . .
H15C H 0.1740 0.0511 0.5477 0.108 Uiso 1 1 calc R . .
F1 F 0.24295(6) 0.2921(3) 0.83960(13) 0.0866(6) Uani 1 1 d . . .
F2 F 0.21320(6) 0.0356(3) 0.88775(12) 0.0889(6) Uani 1 1 d . . .
F3 F 0.20131(7) 0.3313(3) 0.93380(11) 0.0954(7) Uani 1 1 d . . .
O1 O 0.16527(6) 0.1312(2) 0.71011(11) 0.0532(5) Uani 1 1 d . . .
O2 O 0.15409(6) 0.4519(2) 0.75416(11) 0.0541(5) Uani 1 1 d . . .
O3 O 0.05199(8) 0.7210(3) 0.58533(16) 0.0847(7) 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 F3 1.323(3) . ?
C1 F1 1.325(3) . ?
C1 F2 1.331(4) . ?
C1 C2 1.532(4) . ?
C2 O2 1.402(3) . ?
C2 O1 1.413(3) . ?
C2 C3 1.505(4) . ?
C3 C4 1.381(4) . ?
C3 C8 1.384(4) . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.361(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 O2 1.435(3) . ?
C9 C10 1.506(4) . ?
C9 C14 1.518(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.507(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.213(3) . ?
C11 C12 1.460(4) . ?
C12 C13 1.317(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.495(4) . ?
C13 H13 0.9300 . ?
C14 O1 1.451(3) . ?
C14 C15 1.510(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F3 C1 F1 107.5(2) . . ?
F3 C1 F2 107.6(3) . . ?
F1 C1 F2 106.3(2) . . ?
F3 C1 C2 111.0(2) . . ?
F1 C1 C2 112.0(2) . . ?
F2 C1 C2 112.3(2) . . ?
O2 C2 O1 107.99(19) . . ?
O2 C2 C3 110.61(18) . . ?
O1 C2 C3 113.4(2) . . ?
O2 C2 C1 107.7(2) . . ?
O1 C2 C1 105.4(2) . . ?
C3 C2 C1 111.4(2) . . ?
C4 C3 C8 118.5(3) . . ?
C4 C3 C2 121.3(2) . . ?
C8 C3 C2 120.2(2) . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C3 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
O2 C9 C10 108.0(2) . . ?
O2 C9 C14 102.73(18) . . ?
C10 C9 C14 115.2(2) . . ?
O2 C9 H9 110.2 . . ?
C10 C9 H9 110.2 . . ?
C14 C9 H9 110.2 . . ?
C11 C10 C9 112.1(2) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 C12 122.6(3) . . ?
O3 C11 C10 121.4(3) . . ?
C12 C11 C10 116.0(2) . . ?
C13 C12 C11 122.5(3) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C12 C13 C14 124.5(2) . . ?
C12 C13 H13 117.7 . . ?
C14 C13 H13 117.7 . . ?
O1 C14 C13 108.32(18) . . ?
O1 C14 C15 107.9(2) . . ?
C13 C14 C15 111.6(2) . . ?
O1 C14 C9 101.65(19) . . ?
C13 C14 C9 112.5(2) . . ?
C15 C14 C9 114.1(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 O1 C14 107.19(18) . . ?
C2 O2 C9 108.61(16) . . ?

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
F3 C1 C2 O2 65.1(3) . . . . ?
F1 C1 C2 O2 -54.9(3) . . . . ?
F2 C1 C2 O2 -174.47(19) . . . . ?
F3 C1 C2 O1 -179.7(2) . . . . ?
F1 C1 C2 O1 60.2(3) . . . . ?
F2 C1 C2 O1 -59.3(3) . . . . ?
F3 C1 C2 C3 -56.3(3) . . . . ?
F1 C1 C2 C3 -176.4(2) . . . . ?
F2 C1 C2 C3 64.1(3) . . . . ?
O2 C2 C3 C4 159.9(2) . . . . ?
O1 C2 C3 C4 38.4(3) . . . . ?
C1 C2 C3 C4 -80.4(3) . . . . ?
O2 C2 C3 C8 -21.0(3) . . . . ?
O1 C2 C3 C8 -142.5(2) . . . . ?
C1 C2 C3 C8 98.7(3) . . . . ?
C8 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 C5 179.3(2) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C3 1.0(4) . . . . ?
C4 C3 C8 C7 -0.7(4) . . . . ?
C2 C3 C8 C7 -179.9(2) . . . . ?
O2 C9 C10 C11 -65.5(3) . . . . ?
C14 C9 C10 C11 48.6(3) . . . . ?
C9 C10 C11 O3 143.8(3) . . . . ?
C9 C10 C11 C12 -37.5(3) . . . . ?
O3 C11 C12 C13 -167.1(3) . . . . ?
C10 C11 C12 C13 14.2(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 O1 122.3(3) . . . . ?
C12 C13 C14 C15 -119.1(3) . . . . ?
C12 C13 C14 C9 10.7(3) . . . . ?
O2 C9 C14 O1 -33.5(2) . . . . ?
C10 C9 C14 O1 -150.7(2) . . . . ?
O2 C9 C14 C13 82.1(2) . . . . ?
C10 C9 C14 C13 -35.0(3) . . . . ?
O2 C9 C14 C15 -149.3(2) . . . . ?
C10 C9 C14 C15 93.5(3) . . . . ?
O2 C2 O1 C14 -16.0(2) . . . . ?
C3 C2 O1 C14 106.9(2) . . . . ?
C1 C2 O1 C14 -131.0(2) . . . . ?
C13 C14 O1 C2 -88.1(2) . . . . ?
C15 C14 O1 C2 150.9(2) . . . . ?
C9 C14 O1 C2 30.6(2) . . . . ?
O1 C2 O2 C9 -6.7(2) . . . . ?
C3 C2 O2 C9 -131.35(19) . . . . ?
C1 C2 O2 C9 106.7(2) . . . . ?
C10 C9 O2 C2 147.5(2) . . . . ?
C14 C9 O2 C2 25.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.041

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Petroleum ethe'
