# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1470631'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Cl F O3'
_chemical_formula_weight         330.73
_chemical_absolute_configuration ad

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic'
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.958(3)
_cell_length_b                   9.449(3)
_cell_length_c                   19.866(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1493.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1236
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      19.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9285
_exptl_absorpt_correction_T_max  0.9412
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8451
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2638
_reflns_number_gt                1741
_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-97 (Sheldrick, 2008)'
_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)+(0.0331P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_number_reflns         2638
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.001
_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 0.0453(3) 0.2010(3) 0.87780(14) 0.0466(7) Uani 1 1 d . . .
C2 C -0.0563(4) 0.1265(3) 0.92310(15) 0.0563(8) Uani 1 1 d . . .
H2 H -0.0112 0.0519 0.9477 0.068 Uiso 1 1 calc R . .
C3 C -0.2225(4) 0.1630(3) 0.93148(15) 0.0584(9) Uani 1 1 d . . .
C4 C -0.2946(4) 0.2725(4) 0.89539(16) 0.0645(9) Uani 1 1 d . . .
H4 H -0.4070 0.2960 0.9015 0.077 Uiso 1 1 calc R . .
C5 C -0.1969(4) 0.3459(3) 0.85033(15) 0.0574(8) Uani 1 1 d . . .
H5 H -0.2440 0.4193 0.8254 0.069 Uiso 1 1 calc R . .
C6 C -0.0273(3) 0.3116(3) 0.84146(13) 0.0447(7) Uani 1 1 d . . .
C7 C 0.0732(3) 0.3949(3) 0.79356(14) 0.0499(7) Uani 1 1 d . . .
C8 C 0.2604(3) 0.3569(3) 0.78464(14) 0.0452(7) Uani 1 1 d . . .
C9 C 0.2953(3) 0.2040(3) 0.80106(13) 0.0493(7) Uani 1 1 d . . .
H9A H 0.4156 0.1877 0.7997 0.059 Uiso 1 1 calc R . .
H9B H 0.2436 0.1444 0.7672 0.059 Uiso 1 1 calc R . .
C10 C 0.2284(3) 0.1626(3) 0.87041(14) 0.0569(8) Uani 1 1 d . . .
H10A H 0.2420 0.0615 0.8768 0.068 Uiso 1 1 calc R . .
H10B H 0.2931 0.2106 0.9049 0.068 Uiso 1 1 calc R . .
C11 C 0.3218(3) 0.4040(3) 0.71596(13) 0.0498(7) Uani 1 1 d . . .
H11 H 0.2887 0.5026 0.7082 0.060 Uiso 1 1 calc R . .
C12 C 0.2629(3) 0.3140(3) 0.65806(13) 0.0437(7) Uani 1 1 d . . .
C13 C 0.1031(3) 0.2824(3) 0.63555(14) 0.0508(7) Uani 1 1 d . . .
H13 H 0.0083 0.3181 0.6570 0.061 Uiso 1 1 calc R . .
C14 C 0.0897(4) 0.1955(4) 0.57966(16) 0.0650(9) Uani 1 1 d . . .
H14 H -0.0164 0.1731 0.5632 0.078 Uiso 1 1 calc R . .
C15 C 0.2295(5) 0.1411(4) 0.54779(16) 0.0732(10) Uani 1 1 d . . .
H15 H 0.2160 0.0835 0.5102 0.088 Uiso 1 1 calc R . .
C16 C 0.3887(5) 0.1709(3) 0.57091(16) 0.0653(9) Uani 1 1 d . . .
H16 H 0.4836 0.1341 0.5499 0.078 Uiso 1 1 calc R . .
C17 C 0.4017(3) 0.2574(3) 0.62624(15) 0.0499(7) Uani 1 1 d . . .
C18 C 0.5533(4) 0.3083(3) 0.66027(18) 0.0646(9) Uani 1 1 d . . .
Cl1 Cl -0.34442(13) 0.06678(10) 0.98743(5) 0.0915(4) Uani 1 1 d . . .
F1 F 0.3435(2) 0.44174(17) 0.83305(8) 0.0699(5) Uani 1 1 d . . .
O1 O 0.0157(3) 0.4934(2) 0.76142(11) 0.0726(7) Uani 1 1 d . . .
O2 O 0.5047(2) 0.3925(2) 0.71363(11) 0.0650(6) Uani 1 1 d . . .
O3 O 0.7001(3) 0.2912(3) 0.64777(14) 0.0962(9) 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 C6 1.396(3) . ?
C1 C2 1.399(4) . ?
C1 C10 1.509(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 Cl1 1.733(3) . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.471(4) . ?
C7 O1 1.219(3) . ?
C7 C8 1.542(4) . ?
C8 F1 1.416(3) . ?
C8 C9 1.507(3) . ?
C8 C11 1.516(4) . ?
C9 C10 1.528(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.461(3) . ?
C11 C12 1.505(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.381(3) . ?
C12 C17 1.380(4) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.465(4) . ?
C18 O3 1.205(3) . ?
C18 O2 1.381(4) . ?

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
C6 C1 C2 118.0(3) . . ?
C6 C1 C10 122.0(3) . . ?
C2 C1 C10 120.0(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 Cl1 119.0(3) . . ?
C4 C3 Cl1 119.5(3) . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 C7 120.7(3) . . ?
C5 C6 C7 118.8(3) . . ?
O1 C7 C6 122.9(3) . . ?
O1 C7 C8 118.7(3) . . ?
C6 C7 C8 118.4(2) . . ?
F1 C8 C9 108.0(2) . . ?
F1 C8 C11 107.1(2) . . ?
C9 C8 C11 114.6(2) . . ?
F1 C8 C7 104.0(2) . . ?
C9 C8 C7 112.1(2) . . ?
C11 C8 C7 110.3(2) . . ?
C8 C9 C10 112.1(2) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C1 C10 C9 111.3(2) . . ?
C1 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C1 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O2 C11 C12 104.1(2) . . ?
O2 C11 C8 109.1(2) . . ?
C12 C11 C8 114.9(2) . . ?
O2 C11 H11 109.5 . . ?
C12 C11 H11 109.5 . . ?
C8 C11 H11 109.5 . . ?
C13 C12 C17 120.3(3) . . ?
C13 C12 C11 131.0(3) . . ?
C17 C12 C11 108.7(2) . . ?
C12 C13 C14 117.3(3) . . ?
C12 C13 H13 121.4 . . ?
C14 C13 H13 121.4 . . ?
C15 C14 C13 121.8(3) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 117.2(3) . . ?
C17 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
C16 C17 C12 122.5(3) . . ?
C16 C17 C18 128.8(3) . . ?
C12 C17 C18 108.7(3) . . ?
O3 C18 O2 120.5(3) . . ?
O3 C18 C17 131.3(3) . . ?
O2 C18 C17 108.2(3) . . ?
C18 O2 C11 110.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032
