# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

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

data_exp_5652
_database_code_depnum_ccdc_archive 'CCDC 1451285'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;
_audit_creation_date             2015-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H11 F O3'
_chemical_formula_sum            'C17 H11 F O3'
_chemical_formula_weight         282.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H17 O3 F1'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_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                   14.778(3)
_cell_length_b                   5.9149(9)
_cell_length_c                   29.159(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2548.8(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    613
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      22.1260
_cell_measurement_theta_min      4.2330
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1222
_diffrn_reflns_av_unetI/netI     0.1853
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            7133
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.011
_diffrn_reflns_theta_min         3.091
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -19.0000    0.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -99.0000 -180.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0463646000
_diffrn_orient_matrix_UB_12      -0.0120294000
_diffrn_orient_matrix_UB_13      0.0058724000
_diffrn_orient_matrix_UB_21      -0.0108612000
_diffrn_orient_matrix_UB_22      -0.0166136000
_diffrn_orient_matrix_UB_23      -0.0234595000
_diffrn_orient_matrix_UB_31      0.0061983000
_diffrn_orient_matrix_UB_32      -0.1180387000
_diffrn_orient_matrix_UB_33      0.0027145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1032
_reflns_number_total             2496
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2018
_refine_ls_R_factor_gt           0.0801
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.2043
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3438(3) 0.6886(7) 0.40524(16) 0.0258(12) Uani 1 1 d . . . . .
C2 C 0.3869(3) 0.5007(7) 0.37727(16) 0.0241(12) Uani 1 1 d . . . . .
C3 C 0.4196(3) 0.3474(7) 0.40684(16) 0.0243(12) Uani 1 1 d . . . . .
C4 C 0.3978(3) 0.4130(7) 0.45462(17) 0.0269(12) Uani 1 1 d . . . . .
C5 C 0.4152(3) 0.3080(8) 0.49643(18) 0.0341(13) Uani 1 1 d . . . . .
H5 H 0.4450 0.1658 0.4976 0.041 Uiso 1 1 calc R . . . .
C6 C 0.3877(4) 0.4177(8) 0.5368(2) 0.0367(14) Uani 1 1 d . . . . .
H6 H 0.3988 0.3502 0.5659 0.044 Uiso 1 1 calc R . . . .
C7 C 0.3449(4) 0.6216(8) 0.53414(17) 0.0302(13) Uani 1 1 d . . . . .
C8 C 0.3279(3) 0.7312(7) 0.49352(18) 0.0295(13) Uani 1 1 d . . . . .
H8 H 0.2991 0.8748 0.4928 0.035 Uiso 1 1 calc R . . . .
C9 C 0.3545(3) 0.6234(7) 0.45368(17) 0.0257(12) Uani 1 1 d . . . . .
C10 C 0.4749(4) 0.1513(7) 0.39368(19) 0.0327(13) Uani 1 1 d . . . . .
H10 H 0.4892 0.1325 0.3621 0.039 Uiso 1 1 calc R . . . .
C11 C 0.3845(3) 0.4958(7) 0.32710(17) 0.0246(12) Uani 1 1 d . . . . .
C12 C 0.4147(3) 0.6794(7) 0.30129(17) 0.0285(13) Uani 1 1 d . . . . .
H12 H 0.4379 0.8092 0.3165 0.034 Uiso 1 1 calc R . . . .
C13 C 0.4112(3) 0.6750(7) 0.25436(17) 0.0299(12) Uani 1 1 d . . . . .
H13 H 0.4342 0.7992 0.2373 0.036 Uiso 1 1 calc R . . . .
C14 C 0.3748(4) 0.4920(8) 0.23153(17) 0.0295(12) Uani 1 1 d . . . . .
C15 C 0.3439(3) 0.3078(7) 0.25635(18) 0.0310(13) Uani 1 1 d . . . . .
H15 H 0.3193 0.1803 0.2409 0.037 Uiso 1 1 calc R . . . .
C16 C 0.3490(4) 0.3104(7) 0.30343(16) 0.0272(12) Uani 1 1 d . . . . .
H16 H 0.3281 0.1832 0.3202 0.033 Uiso 1 1 calc R . . . .
C17 C 0.3306(4) 0.3263(8) 0.15951(19) 0.0536(18) Uani 1 1 d . . . . .
H17A H 0.3676 0.1895 0.1622 0.080 Uiso 1 1 calc GR . . . .
H17B H 0.3257 0.3693 0.1271 0.080 Uiso 1 1 calc GR . . . .
H17C H 0.2701 0.2968 0.1719 0.080 Uiso 1 1 calc GR . . . .
F1 F 0.3189(2) 0.7205(4) 0.57377(11) 0.0501(10) Uani 1 1 d . . . . .
O1 O 0.3094(2) 0.8584(5) 0.38978(11) 0.0335(9) Uani 1 1 d . . . . .
O2 O 0.3722(3) 0.5074(5) 0.18491(12) 0.0395(10) Uani 1 1 d . . . . .
O3 O 0.5035(2) 0.0116(5) 0.42065(13) 0.0397(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.518(6) . ?
C1 C9 1.473(6) . ?
C1 O1 1.213(5) . ?
C2 C3 1.342(6) . ?
C2 C11 1.463(6) . ?
C3 C4 1.482(7) . ?
C3 C10 1.470(6) . ?
C4 C5 1.392(7) . ?
C4 C9 1.399(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.364(6) . ?
C7 C8 1.373(7) . ?
C7 F1 1.351(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(6) . ?
C10 H10 0.9500 . ?
C10 O3 1.217(5) . ?
C11 C12 1.395(6) . ?
C11 C16 1.398(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.370(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(6) . ?
C14 C15 1.385(6) . ?
C14 O2 1.363(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.375(6) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 O2 1.440(6) . ?

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
C9 C1 C2 106.2(4) . . ?
O1 C1 C2 125.6(4) . . ?
O1 C1 C9 128.2(4) . . ?
C3 C2 C1 107.5(4) . . ?
C3 C2 C11 129.6(4) . . ?
C11 C2 C1 122.8(4) . . ?
C2 C3 C4 110.4(4) . . ?
C2 C3 C10 124.5(5) . . ?
C10 C3 C4 125.0(4) . . ?
C5 C4 C3 131.8(4) . . ?
C5 C4 C9 119.9(5) . . ?
C9 C4 C3 108.3(4) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.3(5) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(5) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 123.5(5) . . ?
F1 C7 C6 117.7(5) . . ?
F1 C7 C8 118.8(4) . . ?
C7 C8 H8 121.5 . . ?
C7 C8 C9 117.0(4) . . ?
C9 C8 H8 121.5 . . ?
C4 C9 C1 107.5(4) . . ?
C8 C9 C1 130.9(4) . . ?
C8 C9 C4 121.6(5) . . ?
C3 C10 H10 118.0 . . ?
O3 C10 C3 124.1(5) . . ?
O3 C10 H10 118.0 . . ?
C12 C11 C2 121.0(4) . . ?
C12 C11 C16 117.7(4) . . ?
C16 C11 C2 121.2(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(5) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 119.6(5) . . ?
O2 C14 C13 116.1(4) . . ?
O2 C14 C15 124.4(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.5(4) . . ?
C15 C16 H16 119.2 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
C14 O2 C17 118.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
