#=============================================================================
 
data_is_ea722

_audit_author_name                'Villinger, A.' 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C22 H17 F O2'
_chemical_formula_sum
 'C22 H17 F O2' 
_chemical_formula_weight          332.35

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'
 
#==============================================================================

# CRYSTAL DATA

_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'
 
_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.
;
 
loop_
 _space_group_symop_operation_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'
 '-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                    18.9528(12)
_cell_length_b                    8.6413(4)
_cell_length_c                    20.2208(12)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      3311.7(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used      9946
_cell_measurement_theta_min        2.28
_cell_measurement_theta_max       28.73

_exptl_crystal_description       'needle'
_exptl_crystal_colour            'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.333          
_exptl_crystal_F_000              1392
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.330
_exptl_crystal_size_mid           0.070
_exptl_crystal_size_min           0.050
_exptl_absorpt_coefficient_mu     0.092
_shelx_estimated_absorpt_T_min    0.970
_shelx_estimated_absorpt_T_max    0.995
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6538  
_exptl_absorpt_correction_T_max   0.7458 
_exptl_absorpt_process_details    '(SADABS; Sheldrick, 2014)'

#==============================================================================

# EXPERIMENTAL DATA
 
 
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'microfocus sealed tube'
_diffrn_measurement_device_type   'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             86813
_diffrn_reflns_av_unetI/netI      0.0411
_diffrn_reflns_av_R_equivalents   0.1505
_diffrn_reflns_limit_h_min        -25
_diffrn_reflns_limit_h_max        25
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -26
_diffrn_reflns_limit_l_max        26
_diffrn_reflns_theta_min          2.283
_diffrn_reflns_theta_max          27.999
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              3995
_reflns_number_gt                 2762
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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.
;
 
_computing_data_collection        'Bruker Apex V7.51A'
_computing_cell_refinement        'Bruker Apex V7.51A'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'Bruker SHELXTL'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'ORTEP-3v2.01 (Farrugia, 1997)' 
_computing_publication_material   'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 
 
_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 > 2σ(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
'w=1/[σ²(Fo²)+(0.0440P)²+2.1797P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3995
_refine_ls_number_parameters      228
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0874
_refine_ls_R_factor_gt            0.0480
_refine_ls_wR_factor_ref          0.1190
_refine_ls_wR_factor_gt           0.0998
_refine_ls_goodness_of_fit_ref    1.067
_refine_ls_restrained_S_all       1.067
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
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
F1 F 0.30728(6) -0.04869(13) 0.57983(5) 0.0300(3) Uani 1 1 d . . . . .
O1 O 0.28849(6) 0.39273(13) 0.33002(6) 0.0200(3) Uani 1 1 d . . . . .
O2 O 0.31991(7) 0.23550(14) 0.24835(6) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.33739(9) 0.49624(19) 0.35803(9) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.36408(9) 0.46839(19) 0.42126(8) 0.0178(4) Uani 1 1 d . . . . .
C3 C 0.34440(8) 0.3302(2) 0.46060(8) 0.0172(4) Uani 1 1 d . . . . .
C4 C 0.33475(8) 0.1824(2) 0.43203(9) 0.0178(4) Uani 1 1 d . . . . .
C5 C 0.33955(9) 0.15273(19) 0.36092(8) 0.0179(4) Uani 1 1 d . . . . .
H5 H 0.3585 0.0565 0.3467 0.021 Uiso 1 1 calc R U . . .
C6 C 0.31886(9) 0.2531(2) 0.31548(8) 0.0180(4) Uani 1 1 d . . . . .
C7 C 0.35479(9) 0.6260(2) 0.32170(9) 0.0219(4) Uani 1 1 d . . . . .
H7 H 0.3350 0.6418 0.2791 0.026 Uiso 1 1 calc R U . . .
C8 C 0.40132(9) 0.7328(2) 0.34812(9) 0.0231(4) Uani 1 1 d . . . . .
H8 H 0.4135 0.8222 0.3233 0.028 Uiso 1 1 calc R U . . .
C9 C 0.43049(9) 0.7109(2) 0.41077(10) 0.0234(4) Uani 1 1 d . . . . .
C10 C 0.41108(9) 0.5793(2) 0.44605(9) 0.0213(4) Uani 1 1 d . . . . .
H10 H 0.4306 0.5639 0.4888 0.026 Uiso 1 1 calc R U . . .
C11 C 0.48231(10) 0.8257(2) 0.43870(11) 0.0317(5) Uani 1 1 d . . . . .
H11A H 0.5176 0.8515 0.4050 0.048 Uiso 1 1 calc R U . . .
H11B H 0.5059 0.7805 0.4773 0.048 Uiso 1 1 calc R U . . .
H11C H 0.4572 0.9199 0.4520 0.048 Uiso 1 1 calc R U . . .
C12 C 0.33806(9) 0.3450(2) 0.52940(9) 0.0215(4) Uani 1 1 d . . . . .
H12 H 0.3430 0.4445 0.5489 0.026 Uiso 1 1 calc R U . . .
C13 C 0.32481(9) 0.2194(2) 0.56967(9) 0.0233(4) Uani 1 1 d . . . . .
H13 H 0.3203 0.2313 0.6162 0.028 Uiso 1 1 calc R U . . .
C14 C 0.31831(9) 0.0772(2) 0.54044(9) 0.0212(4) Uani 1 1 d . . . . .
C15 C 0.32257(9) 0.0548(2) 0.47339(9) 0.0196(4) Uani 1 1 d . . . . .
H15 H 0.3173 -0.0458 0.4552 0.023 Uiso 1 1 calc R U . . .
C16 C 0.35415(9) 0.1028(2) 0.22370(8) 0.0183(4) Uani 1 1 d . . . . .
C17 C 0.42684(9) 0.1029(2) 0.21724(9) 0.0220(4) Uani 1 1 d . . . . .
H17 H 0.4539 0.1886 0.2321 0.026 Uiso 1 1 calc R U . . .
C18 C 0.45956(9) -0.0248(2) 0.18864(9) 0.0237(4) Uani 1 1 d . . . . .
H18 H 0.5095 -0.0262 0.1844 0.028 Uiso 1 1 calc R U . . .
C19 C 0.42042(9) -0.1502(2) 0.16616(9) 0.0216(4) Uani 1 1 d . . . . .
C20 C 0.34720(9) -0.1451(2) 0.17286(9) 0.0207(4) Uani 1 1 d . . . . .
H20 H 0.3196 -0.2294 0.1573 0.025 Uiso 1 1 calc R U . . .
C21 C 0.31388(9) -0.0193(2) 0.20186(8) 0.0196(4) Uani 1 1 d . . . . .
H21 H 0.2640 -0.0175 0.2066 0.024 Uiso 1 1 calc R U . . .
C22 C 0.45590(11) -0.2883(2) 0.13523(11) 0.0333(5) Uani 1 1 d . . . . .
H22A H 0.4324 -0.3139 0.0935 0.050 Uiso 1 1 calc R U . . .
H22B H 0.4528 -0.3768 0.1654 0.050 Uiso 1 1 calc R U . . .
H22C H 0.5056 -0.2641 0.1267 0.050 Uiso 1 1 calc R U . . .
 
 
#==============================================================================

# MOLECULAR GEOMETRY

_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 C14 1.364(2) . ?
O1 C6 1.369(2) . ?
O1 C1 1.407(2) . ?
O2 C6 1.366(2) . ?
O2 C16 1.408(2) . ?
C1 C7 1.381(2) . ?
C1 C2 1.396(2) . ?
C2 C10 1.401(2) . ?
C2 C3 1.483(2) . ?
C3 C12 1.402(2) . ?
C3 C4 1.413(2) . ?
C4 C15 1.403(2) . ?
C4 C5 1.463(2) . ?
C5 C6 1.323(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(3) . ?
C9 C11 1.506(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(2) . ?
C15 H15 0.9500 . ?
C16 C21 1.375(2) . ?
C16 C17 1.384(2) . ?
C17 C18 1.392(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.395(2) . ?
C19 C22 1.506(3) . ?
C20 C21 1.387(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C6 O1 C1 111.71(12) . . ?
C6 O2 C16 116.68(13) . . ?
C7 C1 C2 122.74(16) . . ?
C7 C1 O1 117.35(15) . . ?
C2 C1 O1 119.85(15) . . ?
C1 C2 C10 116.12(16) . . ?
C1 C2 C3 122.63(15) . . ?
C10 C2 C3 121.25(16) . . ?
C12 C3 C4 118.49(16) . . ?
C12 C3 C2 118.71(15) . . ?
C4 C3 C2 122.74(15) . . ?
C15 C4 C3 119.18(16) . . ?
C15 C4 C5 117.26(15) . . ?
C3 C4 C5 123.51(16) . . ?
C6 C5 C4 123.30(16) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 O2 127.79(16) . . ?
C5 C6 O1 123.59(16) . . ?
O2 C6 O1 108.53(14) . . ?
C1 C7 C8 119.25(17) . . ?
C1 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C9 120.83(17) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 118.13(17) . . ?
C10 C9 C11 121.23(17) . . ?
C8 C9 C11 120.64(17) . . ?
C9 C10 C2 122.92(17) . . ?
C9 C10 H10 118.5 . . ?
C2 C10 H10 118.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C3 121.95(17) . . ?
C13 C12 H12 119.0 . . ?
C3 C12 H12 119.0 . . ?
C14 C13 C12 117.88(17) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
F1 C14 C13 118.51(16) . . ?
F1 C14 C15 118.29(16) . . ?
C13 C14 C15 123.20(17) . . ?
C14 C15 C4 119.22(17) . . ?
C14 C15 H15 120.4 . . ?
C4 C15 H15 120.4 . . ?
C21 C16 C17 121.50(16) . . ?
C21 C16 O2 118.85(15) . . ?
C17 C16 O2 119.46(16) . . ?
C16 C17 C18 118.85(16) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C19 C18 C17 121.10(17) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 118.33(17) . . ?
C18 C19 C22 121.03(17) . . ?
C20 C19 C22 120.64(17) . . ?
C21 C20 C19 121.24(16) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C16 C21 C20 118.98(16) . . ?
C16 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C6 O1 C1 C7 113.66(17) . . . . ?
C6 O1 C1 C2 -68.77(19) . . . . ?
C7 C1 C2 C10 -1.0(2) . . . . ?
O1 C1 C2 C10 -178.42(14) . . . . ?
C7 C1 C2 C3 178.98(16) . . . . ?
O1 C1 C2 C3 1.6(2) . . . . ?
C1 C2 C3 C12 -144.71(17) . . . . ?
C10 C2 C3 C12 35.3(2) . . . . ?
C1 C2 C3 C4 38.1(2) . . . . ?
C10 C2 C3 C4 -141.88(17) . . . . ?
C12 C3 C4 C15 -3.0(2) . . . . ?
C2 C3 C4 C15 174.16(15) . . . . ?
C12 C3 C4 C5 179.56(16) . . . . ?
C2 C3 C4 C5 -3.3(3) . . . . ?
C15 C4 C5 C6 147.84(17) . . . . ?
C3 C4 C5 C6 -34.7(3) . . . . ?
C4 C5 C6 O2 -178.71(16) . . . . ?
C4 C5 C6 O1 -2.5(3) . . . . ?
C16 O2 C6 C5 -7.8(3) . . . . ?
C16 O2 C6 O1 175.46(13) . . . . ?
C1 O1 C6 C5 70.2(2) . . . . ?
C1 O1 C6 O2 -112.96(15) . . . . ?
C2 C1 C7 C8 0.9(3) . . . . ?
O1 C1 C7 C8 178.38(15) . . . . ?
C1 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 C11 178.67(17) . . . . ?
C8 C9 C10 C2 0.3(3) . . . . ?
C11 C9 C10 C2 -178.79(17) . . . . ?
C1 C2 C10 C9 0.4(2) . . . . ?
C3 C2 C10 C9 -179.61(16) . . . . ?
C4 C3 C12 C13 1.9(3) . . . . ?
C2 C3 C12 C13 -175.37(16) . . . . ?
C3 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 F1 178.10(15) . . . . ?
C12 C13 C14 C15 -1.7(3) . . . . ?
F1 C14 C15 C4 -179.23(15) . . . . ?
C13 C14 C15 C4 0.6(3) . . . . ?
C3 C4 C15 C14 1.8(2) . . . . ?
C5 C4 C15 C14 179.43(15) . . . . ?
C6 O2 C16 C21 103.29(18) . . . . ?
C6 O2 C16 C17 -81.7(2) . . . . ?
C21 C16 C17 C18 -0.8(3) . . . . ?
O2 C16 C17 C18 -175.66(15) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C17 C18 C19 C22 -179.99(18) . . . . ?
C18 C19 C20 C21 -0.7(3) . . . . ?
C22 C19 C20 C21 179.35(17) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
O2 C16 C21 C20 175.07(15) . . . . ?
C19 C20 C21 C16 0.6(3) . . . . ?
 
_refine_diff_density_max    0.287
_refine_diff_density_min   -0.298
_refine_diff_density_rms    0.060



