# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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#######################################################################

data_2aK_17srv045
_database_code_depnum_ccdc_archive 'CCDC 1857922'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_audit_creation_date             2018-07-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        
;
2-fluoro-1,3-diphenyl-1,3-propanedione
;
_chemical_formula_moiety         'C15 H11 F O2'
_chemical_formula_sum            'C15 H11 F O2'
_chemical_formula_weight         242.24
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.2572(6)
_cell_length_b                   5.1221(2)
_cell_length_c                   16.7741(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.5575(19)
_cell_angle_gamma                90
_cell_volume                     1129.15(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7150
_cell_measurement_temperature    120
_cell_measurement_theta_max      34.39
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) 
 was 0.1131 before and 0.0496 after correction. The Ratio of minimum to maximum 
 transmission is 0.9406. The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 -1.00 0.0580
-1.00 0.00 1.00 0.0220
-1.00 1.00 -1.00 0.1250
1.00 -1.00 1.00 0.1250
1.00 0.00 1.00 0.0880
-1.00 -1.00 0.00 0.1150
1.00 1.00 0.00 0.1390
0.00 0.00 1.00 0.0670
0.00 0.00 -1.00 0.0520

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.119
_exptl_special_details           
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 3 runs of 340 and 1 run of 288 narrow-
frame ω-scans (scan width 0.5°, 10s exposure), every run at a different 
φ angle. Two runs of 358 φ-scans (scan width 1°, 1.5s exposure) were 
used for scaling overflowing intensities. Crystal to detector distance 
3.49 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10000
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.450
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1191
_reflns_number_total             1359
_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       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1359
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+0.3454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0884
_refine_special_details          
;
 The whole molecule is disordered between two near-overlapping positions 
 related by the crystallographic twofold axis.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C1)
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: F(0.5) O1(0.5) O2(0.5) C1(0.5) C2(0.5) H2(0.5) C3(0.5) H3(0.5)
 C4(0.5) H4(0.5) C5(0.5) H5(0.5) C6(0.5) H6(0.5) C7(0.5) C8(0.5) H8(0.5)
 C9(0.5) C10(0.5) C11(0.5) H11(0.5) C12(0.5) H12(0.5) C13(0.5) H13(0.5)
 C14(0.5) H14(0.5) C15(0.5) H15(0.5)
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
F F 0.82541(8) 0.7481(2) 0.49983(6) 0.0257(3) Uani 0.5 1 d . U P A -1
O1 O 0.8304(3) 0.4371(8) 0.38114(14) 0.0281(6) Uani 0.5 1 d . U P A -1
O2 O 0.6523(3) 0.4464(8) 0.59147(14) 0.0295(6) Uani 0.5 1 d . U P A -1
C1 C 0.6708(3) 0.2300(7) 0.3827(3) 0.0185(7) Uani 0.5 1 d . U P A -1
C2 C 0.6915(8) 0.0426(17) 0.3268(6) 0.0192(12) Uani 0.5 1 d . U P A -1
H2 H 0.755931 0.041091 0.307708 0.023 Uiso 0.5 1 calc R . P A -1
C3 C 0.6198(7) -0.1386(14) 0.2992(6) 0.0204(10) Uani 0.5 1 d . U P A -1
H3 H 0.634103 -0.267232 0.261477 0.025 Uiso 0.5 1 calc R . P A -1
C4 C 0.5224(5) -0.1328(14) 0.3279(4) 0.0185(9) Uani 0.5 1 d . U P A -1
H4 H 0.471981 -0.259041 0.310024 0.022 Uiso 0.5 1 calc R . P A -1
C5 C 0.5029(9) 0.060(2) 0.3821(7) 0.0219(11) Uani 0.5 1 d . U P A -1
H5 H 0.438345 0.065604 0.400833 0.026 Uiso 0.5 1 calc R . P A -1
C6 C 0.5756(6) 0.2420(18) 0.4092(3) 0.0224(11) Uani 0.5 1 d . U P A -1
H6 H 0.561033 0.374694 0.445531 0.027 Uiso 0.5 1 calc R . P A -1
C7 C 0.7532(4) 0.4133(10) 0.4124(2) 0.0192(7) Uani 0.5 1 d . U P A -1
C8 C 0.7418(4) 0.5845(3) 0.48597(16) 0.0201(7) Uani 0.5 1 d . U P A -1
H8 H 0.679585 0.694881 0.473044 0.024 Uiso 0.5 1 calc R . P A -1
C9 C 0.7320(4) 0.4314(10) 0.5629(2) 0.0190(7) Uani 0.5 1 d . U P A -1
C10 C 0.8149(3) 0.2563(7) 0.5984(3) 0.0185(7) Uani 0.5 1 d . U P A -1
C11 C 0.7979(8) 0.0934(18) 0.6613(6) 0.0217(12) Uani 0.5 1 d . U P A -1
H11 H 0.734243 0.100132 0.681457 0.026 Uiso 0.5 1 calc R . P A -1
C12 C 0.8714(8) -0.0780(14) 0.6950(6) 0.0283(15) Uani 0.5 1 d . U P A -1
H12 H 0.858594 -0.184638 0.738927 0.034 Uiso 0.5 1 calc R . P A -1
C13 C 0.9611(6) -0.0958(17) 0.6664(5) 0.0339(16) Uani 0.5 1 d . U P A -1
H13 H 1.010471 -0.217876 0.689460 0.041 Uiso 0.5 1 calc R . P A -1
C14 C 0.9825(9) 0.062(3) 0.6036(7) 0.0303(17) Uani 0.5 1 d . U P A -1
H14 H 1.046360 0.048905 0.583958 0.036 Uiso 0.5 1 calc R . P A -1
C15 C 0.9110(6) 0.2370(18) 0.5700(3) 0.0231(10) Uani 0.5 1 d . U P A -1
H15 H 0.925799 0.346321 0.527262 0.028 Uiso 0.5 1 calc R . P A -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F 0.0290(6) 0.0208(5) 0.0274(5) -0.0004(4) 0.0047(4) -0.0087(4)
O1 0.0230(12) 0.0356(10) 0.0280(14) -0.0021(13) 0.0124(11) -0.0070(9)
O2 0.0247(13) 0.0366(10) 0.0294(15) 0.0012(13) 0.0114(11) 0.0050(9)
C1 0.0194(11) 0.0170(7) 0.019(2) 0.0007(6) 0.0035(13) -0.0041(7)
C2 0.024(3) 0.020(3) 0.016(2) -0.0022(15) 0.0075(17) 0.004(2)
C3 0.0249(18) 0.017(3) 0.0189(17) -0.0038(18) 0.0024(11) 0.0041(19)
C4 0.0120(17) 0.0232(19) 0.0208(14) -0.0021(12) 0.0043(14) -0.0018(15)
C5 0.014(2) 0.0250(16) 0.027(3) 0.0028(19) 0.0050(19) 0.0007(16)
C6 0.024(2) 0.0229(13) 0.022(3) 0.002(2) 0.0089(19) 0.0075(13)
C7 0.0230(16) 0.0169(12) 0.0183(17) -0.0021(14) 0.0052(13) 0.0017(10)
C8 0.0197(15) 0.0171(7) 0.024(2) 0.0021(7) 0.0038(15) -0.0057(9)
C9 0.0203(14) 0.0168(12) 0.0207(19) 0.0001(15) 0.0052(14) 0.0038(9)
C10 0.0194(11) 0.0170(7) 0.019(2) 0.0007(6) 0.0035(13) -0.0041(7)
C11 0.0225(18) 0.021(3) 0.022(3) -0.0012(16) 0.0062(18) -0.0014(18)
C12 0.037(2) 0.024(3) 0.0243(18) 0.007(2) 0.0079(16) -0.004(2)
C13 0.026(3) 0.034(3) 0.038(2) -0.0043(16) -0.0078(16) 0.0113(16)
C14 0.022(4) 0.038(2) 0.032(4) -0.005(2) 0.009(2) -0.005(2)
C15 0.023(2) 0.0237(13) 0.024(3) -0.002(2) 0.009(2) -0.0024(13)

_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
F C8 1.384(4) . ?
O1 C7 1.216(6) . ?
O2 C9 1.219(6) . ?
C1 C2 1.396(7) . ?
C1 C6 1.393(9) . ?
C1 C7 1.476(5) . ?
C2 C3 1.366(7) . ?
C3 C4 1.436(11) . ?
C4 C5 1.389(13) . ?
C5 C6 1.375(12) . ?
C7 C8 1.538(4) . ?
C8 C9 1.530(4) . ?
C9 C10 1.482(4) . ?
C10 C11 1.386(7) . ?
C10 C15 1.421(9) . ?
C11 C12 1.377(8) . ?
C12 C13 1.342(13) . ?
C13 C14 1.387(15) . ?
C14 C15 1.371(13) . ?

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
C2 C1 C7 117.5(5) . . ?
C6 C1 C2 120.8(6) . . ?
C6 C1 C7 121.8(4) . . ?
C3 C2 C1 120.3(8) . . ?
C2 C3 C4 119.3(7) . . ?
C5 C4 C3 119.2(7) . . ?
C6 C5 C4 121.0(11) . . ?
C5 C6 C1 119.4(8) . . ?
O1 C7 C1 123.1(4) . . ?
O1 C7 C8 117.8(4) . . ?
C1 C7 C8 119.1(4) . . ?
F C8 C7 108.6(4) . . ?
F C8 C9 108.9(3) . . ?
C9 C8 C7 114.38(14) . . ?
O2 C9 C8 118.3(4) . . ?
O2 C9 C10 121.0(4) . . ?
C10 C9 C8 120.6(4) . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 C15 117.1(6) . . ?
C15 C10 C9 123.9(4) . . ?
C12 C11 C10 121.3(9) . . ?
C13 C12 C11 120.6(8) . . ?
C12 C13 C14 120.8(8) . . ?
C15 C14 C13 119.6(11) . . ?
C14 C15 C10 120.6(9) . . ?

_shelx_res_file                  
;
TITL 17srv045 in I2/a #15
    17srv045.res
    created by SHELXL-2018/3 at 13:58:13 on 09-Jul-2018
REM reset to I2/a #15
CELL 0.71073 13.2572 5.1221 16.7741 90 97.5575 90
ZERR 4 0.0006 0.0002 0.0008 0 0.0019 0
LATT 2
SYMM 0.5-X,+Y,-Z
SFAC C H F O
UNIT 60 44 4 8
RIGU
EADP C10 C1

L.S. 7
PLAN  5
SIZE 0.119 0.192 0.3
TEMP -153.15
BOND
fmap 2
acta
OMIT -3 56
REM <olex2.extras>
REM <HklSrc "%.\\17srv045.hkl">
REM </olex2.extras>

WGHT    0.040700    0.345400
EXTI    0.015711
FVAR       0.35240
PART -1
F     3    0.825410    0.748065    0.499832    10.50000    0.02904    0.02077 =
         0.02742   -0.00038    0.00473   -0.00867
O1    4    0.830370    0.437059    0.381140    10.50000    0.02302    0.03557 =
         0.02800   -0.00209    0.01237   -0.00700
O2    4    0.652270    0.446425    0.591469    10.50000    0.02465    0.03656 =
         0.02943    0.00124    0.01135    0.00497
C1    1    0.670758    0.230045    0.382737    10.50000    0.01942    0.01703 =
         0.01932    0.00073    0.00347   -0.00413
C2    1    0.691543    0.042611    0.326755    10.50000    0.02365    0.01977 =
         0.01560   -0.00217    0.00751    0.00411
AFIX  43
H2    2    0.755931    0.041091    0.307708    10.50000   -1.20000
AFIX   0
C3    1    0.619770   -0.138628    0.299220    10.50000    0.02492    0.01730 =
         0.01893   -0.00379    0.00238    0.00407
AFIX  43
H3    2    0.634103   -0.267232    0.261477    10.50000   -1.20000
AFIX   0
C4    1    0.522415   -0.132786    0.327911    10.50000    0.01203    0.02320 =
         0.02084   -0.00215    0.00431   -0.00177
AFIX  43
H4    2    0.471981   -0.259041    0.310024    10.50000   -1.20000
AFIX   0
C5    1    0.502906    0.059720    0.382132    10.50000    0.01411    0.02499 =
         0.02732    0.00279    0.00503    0.00070
AFIX  43
H5    2    0.438345    0.065604    0.400833    10.50000   -1.20000
AFIX   0
C6    1    0.575593    0.241954    0.409171    10.50000    0.02419    0.02287 =
         0.02181    0.00156    0.00890    0.00751
AFIX  43
H6    2    0.561033    0.374694    0.445531    10.50000   -1.20000
AFIX   0
C7    1    0.753178    0.413256    0.412403    10.50000    0.02301    0.01689 =
         0.01830   -0.00212    0.00516    0.00174
C8    1    0.741804    0.584505    0.485973    10.50000    0.01970    0.01710 =
         0.02373    0.00213    0.00385   -0.00565
AFIX  13
H8    2    0.679585    0.694881    0.473044    10.50000   -1.20000
AFIX   0
C9    1    0.732021    0.431448    0.562900    10.50000    0.02029    0.01681 =
         0.02068    0.00013    0.00518    0.00381
C10   1    0.814906    0.256308    0.598415    10.50000    0.01942    0.01703 =
         0.01932    0.00073    0.00347   -0.00413
C11   1    0.797870    0.093407    0.661270    10.50000    0.02245    0.02094 =
         0.02246   -0.00122    0.00625   -0.00140
AFIX  43
H11   2    0.734243    0.100132    0.681457    10.50000   -1.20000
AFIX   0
C12   1    0.871431   -0.078039    0.695020    10.50000    0.03714    0.02434 =
         0.02433    0.00655    0.00793   -0.00388
AFIX  43
H12   2    0.858594   -0.184638    0.738927    10.50000   -1.20000
AFIX   0
C13   1    0.961101   -0.095782    0.666402    10.50000    0.02627    0.03405 =
         0.03810   -0.00425   -0.00783    0.01135
AFIX  43
H13   2    1.010471   -0.217876    0.689460    10.50000   -1.20000
AFIX   0
C14   1    0.982519    0.061982    0.603585    10.50000    0.02229    0.03781 =
         0.03227   -0.00480    0.00877   -0.00548
AFIX  43
H14   2    1.046360    0.048905    0.583958    10.50000   -1.20000
AFIX   0
C15   1    0.910993    0.236965    0.569971    10.50000    0.02349    0.02370 =
         0.02365   -0.00236    0.00883   -0.00245
AFIX  43
H15   2    0.925799    0.346321    0.527262    10.50000   -1.20000
AFIX   0
HKLF 4




REM  17srv045 in I2/a #15
REM wR2 = 0.0884, GooF = S = 1.153, Restrained GooF = 1.113 for all data
REM R1 = 0.0342 for 1191 Fo > 4sig(Fo) and 0.0412 for all 1359 data
REM 158 parameters refined using 132 restraints

END

WGHT      0.0402      0.3516

REM Highest difference peak  0.203,  deepest hole -0.215,  1-sigma level  0.028
Q1    1   0.8584  0.2214  0.5825  11.00000  0.05    0.20
Q2    1   0.9592 -0.0690  0.6199  11.00000  0.05    0.13
Q3    1   0.6740 -0.0815  0.3399  11.00000  0.05    0.12
Q4    1   0.7787  0.2881  0.5725  11.00000  0.05    0.12
Q5    1   0.7500  0.4512  0.5000  10.50000  0.05    0.10
;
_shelx_res_checksum              87352
####################################################################### 
# 
# 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_2cE_17srv145
_database_code_depnum_ccdc_archive 'CCDC 1857925'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_audit_creation_date             2017-05-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7

_chemical_name_common            ?
_chemical_name_systematic        
;
2-fluoro-1,3-bis(4-methylphenyl)-1,3-propandione
;
_chemical_formula_moiety         'C17 H15 F O2'
_chemical_formula_sum            'C17 H15 F O2'
_chemical_formula_weight         270.29
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   11.1604(8)
_cell_length_b                   11.7655(8)
_cell_length_c                   10.8190(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.3180(17)
_cell_angle_gamma                90
_cell_volume                     1294.57(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2799
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.24
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.0677 before and 0.0518 after correction. 
The Ratio of minimum to maximum transmission is 0.7702. 
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
The data collection nominally covered a full sphere of 
reciprocal space by a combination of 3 sets of ω scans 
each set at different φ and/or 2θ angles and each scan 
(7 s exposure) covering -0.300° degrees in ω. 
The crystal to detector distance was 4.85 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7788
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.500
_diffrn_reflns_theta_min         2.647
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Bruker Monocap'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1358
_reflns_number_total             1646
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1646
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0721
_refine_ls_restrained_S_all      1.105
_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)+(0.1500P)²+0.7700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2243
_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. Others
 Fixed Uiso: H1(0.05)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
F1 F 0.5000 0.39159(14) 0.2500 0.0495(6) Uani 1 2 d S T P . .
O1 O 0.58007(11) 0.67509(10) 0.36775(11) 0.0255(4) Uani 1 1 d . . . . .
C1 C 0.5000 0.50728(19) 0.2500 0.0217(5) Uani 1 2 d S T P . .
C2 C 0.57967(14) 0.56506(15) 0.36990(14) 0.0197(4) Uani 1 1 d . . . . .
C3 C 0.66422(13) 0.51018(14) 0.49905(14) 0.0204(4) Uani 1 1 d . . . . .
C4 C 0.66516(16) 0.39344(14) 0.52485(17) 0.0247(4) Uani 1 1 d . . . . .
H4 H 0.6086 0.3441 0.4561 0.030 Uiso 1 1 calc R . . . .
C5 C 0.74786(16) 0.34922(14) 0.64973(16) 0.0256(4) Uani 1 1 d . . . . .
H5 H 0.7464 0.2698 0.6651 0.031 Uiso 1 1 calc R . . . .
C6 C 0.83293(15) 0.41806(14) 0.75316(16) 0.0229(4) Uani 1 1 d . . . . .
C7 C 0.83153(15) 0.53489(14) 0.72793(16) 0.0249(4) Uani 1 1 d . . . . .
H7 H 0.8880 0.5839 0.7972 0.030 Uiso 1 1 calc R . . . .
C8 C 0.74909(16) 0.58009(14) 0.60360(16) 0.0236(4) Uani 1 1 d . . . . .
H8 H 0.7500 0.6596 0.5889 0.028 Uiso 1 1 calc R . . . .
C9 C 0.92479(17) 0.36909(17) 0.88719(18) 0.0300(5) Uani 1 1 d . . . . .
H9A H 1.0151 0.3924 0.9068 0.045 Uiso 1 1 calc GR . . . .
H9B H 0.9189 0.2860 0.8832 0.045 Uiso 1 1 calc GR . . . .
H9C H 0.9002 0.3970 0.9589 0.045 Uiso 1 1 calc GR . . . .
H1 H 0.5000 0.698(3) 0.2500 0.050 Uiso 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0707(13) 0.0252(9) 0.0364(10) 0.000 0.0057(9) 0.000
O1 0.0308(7) 0.0190(7) 0.0221(6) -0.0005(4) 0.0064(5) -0.0020(4)
C1 0.0248(10) 0.0176(10) 0.0210(10) 0.000 0.0076(8) 0.000
C2 0.0200(7) 0.0208(8) 0.0184(8) 0.0001(5) 0.0081(6) -0.0004(5)
C3 0.0198(8) 0.0216(8) 0.0197(8) -0.0001(6) 0.0081(6) -0.0013(6)
C4 0.0266(8) 0.0208(8) 0.0239(8) -0.0018(6) 0.0075(6) -0.0032(6)
C5 0.0289(9) 0.0208(8) 0.0272(9) 0.0030(6) 0.0118(7) 0.0006(6)
C6 0.0215(8) 0.0276(9) 0.0214(8) 0.0025(6) 0.0108(6) 0.0043(6)
C7 0.0249(8) 0.0260(9) 0.0207(8) -0.0025(6) 0.0063(6) -0.0007(6)
C8 0.0277(8) 0.0192(8) 0.0224(8) -0.0021(6) 0.0088(6) -0.0019(6)
C9 0.0282(9) 0.0359(10) 0.0250(9) 0.0078(7) 0.0100(7) 0.0063(7)

_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 C1 1.361(3) . ?
O1 C2 1.2948(19) . ?
O1 H1 1.248(8) . ?
C1 C2 1.4091(18) 2_655 ?
C1 C2 1.4091(18) . ?
C2 C3 1.474(2) . ?
C3 C4 1.401(2) . ?
C3 C8 1.404(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C6 C7 1.400(2) . ?
C6 C9 1.504(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(2) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C2 O1 H1 103.4(16) . . ?
F1 C1 C2 118.85(10) . . ?
F1 C1 C2 118.85(10) . 2_655 ?
C2 C1 C2 122.3(2) . 2_655 ?
O1 C2 C1 118.12(14) . . ?
O1 C2 C3 116.70(13) . . ?
C1 C2 C3 125.18(16) . . ?
C4 C3 C2 124.58(14) . . ?
C4 C3 C8 117.82(14) . . ?
C8 C3 C2 117.59(15) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.64(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.71(15) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C7 117.75(14) . . ?
C5 C6 C9 121.41(16) . . ?
C7 C6 C9 120.83(15) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.05(14) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 H8 119.5 . . ?
C7 C8 C3 121.02(15) . . ?
C7 C8 H8 119.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O1 C2 C1 F1 179.02(9) . . . . ?
C1 C2 C3 C4 -7.9(2) . . . . ?
C1 C2 C3 C8 172.49(12) . . . . ?
C2 C1 C2 O1 0(82) . . . . ?
C2 C1 C2 C3 0(59) . . . . ?
C3 C2 C1 F1 -0.65(15) . . . . ?
C4 C3 C2 O1 172.44(15) . . . . ?
C8 C3 C2 O1 -7.18(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details 
;
TITL 17srv145 in C2/c #15
REM reset to C2/c #15
CELL 0.71073 11.1604 11.7655 10.819 90 114.318 90
ZERR 4 0.0008 0.0008 0.0008 0 0.0017 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H F O
UNIT 68 60 4 8

L.S. 9
PLAN  5
SIZE 0.2 0.26 0.38
TEMP -153.15
CONF O1 C2 C1 F1
CONF C2 C1 C2 O1
CONF C3 C2 C1 F1
CONF C2 C1 C2 C3
CONF C4 C3 C2 O1
CONF C1 C2 C3 C4
CONF C8 C3 C2 O1
CONF C1 C2 C3 C8
BOND $h
fmap 2
acta 
OMIT -2 57
WGHT 0.15 0.77
FVAR 0.09874
REM <olex2.extras>
REM <HklSrc "%.\\17srv145.hkl">
REM </olex2.extras>

F1    3     0.50000  0.39159  0.25000  10.50000  0.07068  0.02522  0.03643 =
 0.00000  0.00567  0.00000 
O1    4     0.58007  0.67509  0.36775  11.00000  0.03083  0.01897  0.02213 =
 -0.00048  0.00639 -0.00199 
C1    1     0.50000  0.50728  0.25000  10.50000  0.02482  0.01760  0.02096 =
 0.00000  0.00764  0.00000 
C2    1     0.57967  0.56506  0.36990  11.00000  0.01998  0.02083  0.01837 =
 0.00013  0.00806 -0.00042 
C3    1     0.66422  0.51018  0.49905  11.00000  0.01979  0.02156  0.01972 =
 -0.00009  0.00809 -0.00131 
C4    1     0.66516  0.39344  0.52485  11.00000  0.02656  0.02076  0.02391 =
 -0.00184  0.00748 -0.00321 
AFIX 43
H4    2     0.60857  0.34410  0.45608  11.00000 -1.20000 
AFIX 0
C5    1     0.74786  0.34922  0.64973  11.00000  0.02893  0.02081  0.02720 =
 0.00296  0.01182  0.00061 
AFIX 43
H5    2     0.74640  0.26983  0.66508  11.00000 -1.20000 
AFIX 0
C6    1     0.83293  0.41806  0.75316  11.00000  0.02149  0.02764  0.02143 =
 0.00251  0.01078  0.00427 
C7    1     0.83153  0.53489  0.72794  11.00000  0.02488  0.02603  0.02071 =
 -0.00245  0.00628 -0.00073 
AFIX 43
H7    2     0.88800  0.58393  0.79717  11.00000 -1.20000 
AFIX 0
C8    1     0.74909  0.58009  0.60360  11.00000  0.02766  0.01917  0.02243 =
 -0.00207  0.00883 -0.00192 
AFIX 43
H8    2     0.75001  0.65963  0.58887  11.00000 -1.20000 
AFIX 0
C9    1     0.92480  0.36909  0.88719  11.00000  0.02817  0.03586  0.02504 =
 0.00777  0.00997  0.00631 
AFIX 137
H9a   2     1.01512  0.39242  0.90677  11.00000 -1.50000 
H9b   2     0.91891  0.28596  0.88322  11.00000 -1.50000 
H9c   2     0.90023  0.39698  0.95892  11.00000 -1.50000 
AFIX 0
H1    2     0.50000  0.69832  0.25000  10.50000  10.05000 
HKLF 4

END
;
####################################################################### 
# 
# 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_2cK_17srv144
_database_code_depnum_ccdc_archive 'CCDC 1857926'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_audit_creation_date             2017-05-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7

_chemical_name_common            ?
_chemical_name_systematic        
;
2-fluoro-1,3-bis(4-methylphenyl)-1,3-propandione
;
_chemical_formula_moiety         'C17 H15 F O2'
_chemical_formula_sum            'C17 H15 F O2'
_chemical_formula_weight         270.29
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5592(5)
_cell_length_b                   12.9739(8)
_cell_length_c                   12.3376(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.4067(17)
_cell_angle_gamma                90
_cell_volume                     1338.05(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6831
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.28
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.0788 before and 0.0687 after correction. 
The Ratio of minimum to maximum transmission is 0.8465. 
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
The data collection nominally covered a full sphere of reciprocal space by a 
combination of 4 sets of ω scans each set at different φ and/or 2θ angles 
and each scan (10 s exposure) covering -0.300° degrees in ω. 
The crystal to detector distance was 4.85 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22309
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_min         2.307
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ω-scan
_diffrn_radiation_collimation    'Bruker Monocap'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_type              ?
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2882
_reflns_number_total             3569
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.086
_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)+(0.1100P)²+0.2100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1749
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
F1 F 0.18465(12) 0.63983(6) 0.22345(8) 0.0346(3) Uani 1 1 d . . . . .
O1 O -0.01022(12) 0.42458(9) 0.12253(8) 0.0330(3) Uani 1 1 d . . . . .
O2 O 0.46823(12) 0.55954(8) 0.25314(8) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.08542(15) 0.46745(11) 0.19617(11) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.19371(17) 0.55104(10) 0.16211(11) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.37076(16) 0.51849(10) 0.18010(10) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.41327(15) 0.43759(10) 0.10748(10) 0.0219(3) Uani 1 1 d . . . . .
C5 C 0.57059(16) 0.40018(11) 0.13074(11) 0.0254(3) Uani 1 1 d . . . . .
C6 C 0.61587(17) 0.32457(11) 0.06438(12) 0.0281(3) Uani 1 1 d . . . . .
C7 C 0.50784(16) 0.28444(10) -0.02675(11) 0.0253(3) Uani 1 1 d . . . . .
C8 C 0.35113(16) 0.32228(11) -0.04974(11) 0.0260(3) Uani 1 1 d . . . . .
C9 C 0.30442(15) 0.39752(11) 0.01618(11) 0.0255(3) Uani 1 1 d . . . . .
C10 C 0.5567(2) 0.20435(12) -0.10070(14) 0.0347(4) Uani 1 1 d . . . . .
C11 C 0.10220(15) 0.43970(10) 0.31492(11) 0.0224(3) Uani 1 1 d . . . . .
C12 C 0.00160(16) 0.36272(10) 0.34097(11) 0.0247(3) Uani 1 1 d . . . . .
C13 C 0.01790(17) 0.32931(11) 0.44935(12) 0.0263(3) Uani 1 1 d . . . . .
C14 C 0.13377(17) 0.37133(10) 0.53460(11) 0.0246(3) Uani 1 1 d . . . . .
C15 C 0.23266(17) 0.44875(11) 0.50876(11) 0.0263(3) Uani 1 1 d . . . . .
C16 C 0.21713(17) 0.48320(10) 0.40013(11) 0.0257(3) Uani 1 1 d . . . . .
C17 C 0.1565(2) 0.33270(13) 0.65201(12) 0.0315(3) Uani 1 1 d . . . . .
H2 H 0.1490(16) 0.5852(10) 0.0837(11) 0.005(3) Uiso 1 1 d . . . . .
H5 H 0.648(2) 0.4273(15) 0.1967(16) 0.037(5) Uiso 1 1 d . . . . .
H6 H 0.723(2) 0.2975(15) 0.0808(15) 0.033(5) Uiso 1 1 d . . . . .
H8 H 0.273(2) 0.2952(14) -0.1086(16) 0.031(4) Uiso 1 1 d . . . . .
H9 H 0.193(2) 0.4238(14) -0.0040(15) 0.031(4) Uiso 1 1 d . . . . .
H10A H 0.486(4) 0.145(3) -0.112(2) 0.087(9) Uiso 1 1 d . . . . .
H10B H 0.568(3) 0.236(2) -0.176(2) 0.064(7) Uiso 1 1 d . . . . .
H10C H 0.665(3) 0.177(2) -0.073(2) 0.064(7) Uiso 1 1 d . . . . .
H12 H -0.080(2) 0.3329(14) 0.2816(15) 0.027(4) Uiso 1 1 d . . . . .
H13 H -0.048(2) 0.2787(15) 0.4705(16) 0.033(5) Uiso 1 1 d . . . . .
H15 H 0.315(2) 0.4791(15) 0.5651(14) 0.028(4) Uiso 1 1 d . . . . .
H16 H 0.287(2) 0.5371(15) 0.3838(15) 0.032(4) Uiso 1 1 d . . . . .
H17A H 0.239(3) 0.282(2) 0.671(2) 0.076(8) Uiso 1 1 d . . . . .
H17B H 0.186(4) 0.388(3) 0.701(3) 0.088(9) Uiso 1 1 d . . . . .
H17C H 0.062(3) 0.308(2) 0.670(2) 0.069(7) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0439(5) 0.0253(4) 0.0375(5) 0.0022(3) 0.0152(4) 0.0049(3)
O1 0.0252(5) 0.0473(6) 0.0247(5) 0.0023(4) 0.0012(4) -0.0025(4)
O2 0.0308(5) 0.0357(6) 0.0288(5) -0.0041(4) 0.0062(4) -0.0059(4)
C1 0.0211(6) 0.0280(6) 0.0248(6) 0.0033(5) 0.0046(5) 0.0064(5)
C2 0.0286(7) 0.0252(6) 0.0258(6) 0.0049(5) 0.0073(5) 0.0039(5)
C3 0.0247(6) 0.0246(6) 0.0227(6) 0.0047(5) 0.0062(5) -0.0011(5)
C4 0.0214(6) 0.0240(6) 0.0201(6) 0.0042(4) 0.0040(5) -0.0012(4)
C5 0.0213(6) 0.0292(7) 0.0243(6) 0.0014(5) 0.0013(5) -0.0015(5)
C6 0.0234(6) 0.0278(7) 0.0322(7) 0.0010(5) 0.0042(5) 0.0013(5)
C7 0.0266(6) 0.0229(6) 0.0278(7) 0.0022(5) 0.0087(5) -0.0030(5)
C8 0.0235(6) 0.0323(7) 0.0216(6) 0.0007(5) 0.0032(5) -0.0051(5)
C9 0.0204(6) 0.0330(7) 0.0225(6) 0.0022(5) 0.0033(5) -0.0004(5)
C10 0.0346(8) 0.0283(7) 0.0433(9) -0.0070(6) 0.0132(7) -0.0032(6)
C11 0.0223(6) 0.0221(6) 0.0233(6) 0.0010(4) 0.0057(5) 0.0041(5)
C12 0.0208(6) 0.0262(6) 0.0271(7) -0.0013(5) 0.0049(5) 0.0007(5)
C13 0.0252(6) 0.0256(6) 0.0294(7) 0.0012(5) 0.0088(5) -0.0009(5)
C14 0.0279(6) 0.0233(6) 0.0242(6) 0.0003(5) 0.0090(5) 0.0037(5)
C15 0.0274(6) 0.0273(7) 0.0238(6) -0.0021(5) 0.0044(5) -0.0016(5)
C16 0.0276(6) 0.0235(6) 0.0268(6) 0.0001(5) 0.0078(5) -0.0016(5)
C17 0.0384(8) 0.0341(8) 0.0226(7) 0.0033(5) 0.0077(6) -0.0021(6)

_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 C2 1.3896(16) . ?
O1 C1 1.2188(17) . ?
O2 C3 1.2118(16) . ?
C1 C2 1.5424(19) . ?
C1 C11 1.4854(18) . ?
C2 C3 1.5426(19) . ?
C2 H2 1.058(13) . ?
C3 C4 1.4755(18) . ?
C4 C5 1.4017(18) . ?
C4 C9 1.3986(18) . ?
C5 C6 1.385(2) . ?
C5 H5 1.00(2) . ?
C6 C7 1.394(2) . ?
C6 H6 0.958(19) . ?
C7 C8 1.3990(19) . ?
C7 C10 1.500(2) . ?
C8 C9 1.383(2) . ?
C8 H8 0.941(19) . ?
C9 H9 0.997(17) . ?
C10 H10A 0.97(3) . ?
C10 H10B 1.04(3) . ?
C10 H10C 0.98(3) . ?
C11 C12 1.4004(18) . ?
C11 C16 1.3953(19) . ?
C12 C13 1.3839(19) . ?
C12 H12 0.976(18) . ?
C13 C14 1.392(2) . ?
C13 H13 0.94(2) . ?
C14 C15 1.3939(19) . ?
C14 C17 1.5054(19) . ?
C15 C16 1.3918(19) . ?
C15 H15 0.960(17) . ?
C16 H16 0.972(19) . ?
C17 H17A 0.96(3) . ?
C17 H17B 0.93(3) . ?
C17 H17C 0.94(3) . ?

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
O1 C1 C2 117.68(12) . . ?
O1 C1 C11 122.12(13) . . ?
C11 C1 C2 120.18(12) . . ?
F1 C2 C1 109.11(11) . . ?
F1 C2 C3 108.46(11) . . ?
F1 C2 H2 95.7(7) . . ?
C1 C2 C3 113.43(10) . . ?
C1 C2 H2 115.0(7) . . ?
C3 C2 H2 113.4(7) . . ?
O2 C3 C2 118.99(12) . . ?
O2 C3 C4 122.96(12) . . ?
C4 C3 C2 118.05(11) . . ?
C5 C4 C3 118.25(12) . . ?
C9 C4 C3 123.02(11) . . ?
C9 C4 C5 118.72(12) . . ?
C4 C5 H5 118.9(11) . . ?
C6 C5 C4 120.17(13) . . ?
C6 C5 H5 120.9(11) . . ?
C5 C6 C7 121.31(13) . . ?
C5 C6 H6 120.6(11) . . ?
C7 C6 H6 118.1(11) . . ?
C6 C7 C8 118.25(13) . . ?
C6 C7 C10 121.74(13) . . ?
C8 C7 C10 119.99(13) . . ?
C7 C8 H8 120.9(11) . . ?
C9 C8 C7 120.93(12) . . ?
C9 C8 H8 118.1(11) . . ?
C4 C9 H9 120.8(10) . . ?
C8 C9 C4 120.60(12) . . ?
C8 C9 H9 118.6(10) . . ?
C7 C10 H10A 113.1(18) . . ?
C7 C10 H10B 111.4(15) . . ?
C7 C10 H10C 114.0(16) . . ?
H10A C10 H10B 111(2) . . ?
H10A C10 H10C 106(3) . . ?
H10B C10 H10C 101(2) . . ?
C12 C11 C1 117.73(12) . . ?
C16 C11 C1 123.24(12) . . ?
C16 C11 C12 118.97(12) . . ?
C11 C12 H12 119.0(10) . . ?
C13 C12 C11 120.38(12) . . ?
C13 C12 H12 120.6(10) . . ?
C12 C13 C14 120.99(13) . . ?
C12 C13 H13 123.2(12) . . ?
C14 C13 H13 115.8(11) . . ?
C13 C14 C15 118.57(12) . . ?
C13 C14 C17 121.36(13) . . ?
C15 C14 C17 120.04(13) . . ?
C14 C15 H15 121.1(11) . . ?
C16 C15 C14 120.97(13) . . ?
C16 C15 H15 118.0(11) . . ?
C11 C16 H16 120.2(10) . . ?
C15 C16 C11 120.11(12) . . ?
C15 C16 H16 119.7(10) . . ?
C14 C17 H17A 114.0(17) . . ?
C14 C17 H17B 108.9(19) . . ?
C14 C17 H17C 113.4(17) . . ?
H17A C17 H17B 107(3) . . ?
H17A C17 H17C 109(2) . . ?
H17B C17 H17C 104(2) . . ?

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
O1 C1 C2 F1 128.87(13) . . . . ?
O2 C3 C2 F1 11.60(16) . . . . ?
C1 C2 C3 O2 -109.78(14) . . . . ?
C1 C2 C3 C4 69.72(15) . . . . ?
C2 C1 C11 C12 -179.52(11) . . . . ?
C2 C1 C11 C16 -2.40(19) . . . . ?
C2 C3 C4 C5 -173.50(11) . . . . ?
C2 C3 C4 C9 7.17(18) . . . . ?
C3 C2 C1 O1 -110.11(14) . . . . ?
C3 C2 C1 C11 68.40(15) . . . . ?
C4 C3 C2 F1 -168.90(10) . . . . ?
C5 C4 C3 O2 5.98(19) . . . . ?
C9 C4 C3 O2 -173.34(12) . . . . ?
C11 C1 C2 F1 -52.62(15) . . . . ?
C12 C11 C1 O1 -1.07(19) . . . . ?
C16 C11 C1 O1 176.05(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details 
;
TITL 17srv144 in P21/c #14
REM reset to P21/c #14
CELL 0.71073 8.5592 12.9739 12.3376 90 102.4067 90
ZERR 4 0.0005 0.0008 0.0008 0 0.0017 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F O
UNIT 68 60 4 8

L.S. 9
PLAN  5
SIZE 0.26 0.34 0.36
TEMP -153.15
CONF C12 C11 C1 O1
CONF C2 C1 C11 C12
CONF C16 C11 C1 O1
CONF C2 C1 C11 C16
CONF O1 C1 C2 F1
CONF C11 C1 C2 F1
CONF C3 C2 C1 O1
CONF C3 C2 C1 C11
CONF O2 C3 C2 F1
CONF C1 C2 C3 O2
CONF C4 C3 C2 F1
CONF C1 C2 C3 C4
CONF C5 C4 C3 O2
CONF C2 C3 C4 C5
CONF C9 C4 C3 O2
CONF C2 C3 C4 C9
BOND $h
fmap 2
acta 
OMIT -2 58
WGHT 0.11 0.21
FVAR 0.22502
REM <olex2.extras>
REM <HklSrc "%.\\17srv144.hkl">
REM </olex2.extras>

F1    3     0.18465  0.63983  0.22345  11.00000  0.04387  0.02532  0.03754 =
 0.00216  0.01524  0.00486 
O1    4    -0.01023  0.42458  0.12253  11.00000  0.02520  0.04726  0.02468 =
 0.00233  0.00116 -0.00246 
O2    4     0.46823  0.55954  0.25314  11.00000  0.03082  0.03569  0.02884 =
 -0.00412  0.00625 -0.00587 
C1    1     0.08542  0.46745  0.19617  11.00000  0.02115  0.02796  0.02480 =
 0.00333  0.00462  0.00640 
C2    1     0.19371  0.55104  0.16211  11.00000  0.02864  0.02519  0.02580 =
 0.00494  0.00727  0.00391 
C3    1     0.37076  0.51849  0.18010  11.00000  0.02472  0.02457  0.02269 =
 0.00470  0.00624 -0.00113 
C4    1     0.41327  0.43759  0.10748  11.00000  0.02142  0.02399  0.02009 =
 0.00417  0.00404 -0.00118 
C5    1     0.57059  0.40018  0.13074  11.00000  0.02128  0.02915  0.02427 =
 0.00142  0.00131 -0.00152 
C6    1     0.61587  0.32456  0.06438  11.00000  0.02342  0.02778  0.03223 =
 0.00104  0.00417  0.00129 
C7    1     0.50784  0.28444 -0.02675  11.00000  0.02663  0.02288  0.02779 =
 0.00222  0.00868 -0.00301 
C8    1     0.35113  0.32228 -0.04974  11.00000  0.02345  0.03231  0.02160 =
 0.00069  0.00323 -0.00508 
C9    1     0.30442  0.39752  0.01618  11.00000  0.02043  0.03303  0.02253 =
 0.00223  0.00335 -0.00036 
C10   1     0.55665  0.20435 -0.10070  11.00000  0.03460  0.02827  0.04333 =
 -0.00699  0.01323 -0.00315 
C11   1     0.10220  0.43970  0.31492  11.00000  0.02229  0.02209  0.02332 =
 0.00097  0.00566  0.00406 
C12   1     0.00160  0.36272  0.34097  11.00000  0.02079  0.02617  0.02706 =
 -0.00129  0.00485  0.00067 
C13   1     0.01790  0.32931  0.44935  11.00000  0.02520  0.02563  0.02936 =
 0.00120  0.00881 -0.00095 
C14   1     0.13377  0.37133  0.53461  11.00000  0.02787  0.02331  0.02421 =
 0.00032  0.00898  0.00368 
C15   1     0.23266  0.44875  0.50876  11.00000  0.02737  0.02726  0.02383 =
 -0.00213  0.00438 -0.00160 
C16   1     0.21713  0.48320  0.40013  11.00000  0.02758  0.02352  0.02677 =
 0.00012  0.00776 -0.00162 
C17   1     0.15654  0.33270  0.65202  11.00000  0.03845  0.03405  0.02261 =
 0.00328  0.00768 -0.00212 
H2    2     0.14901  0.58523  0.08370  11.00000  0.00498 
H5    2     0.64765  0.42733  0.19666  11.00000  0.03720 
H6    2     0.72257  0.29753  0.08085  11.00000  0.03273 
H8    2     0.27341  0.29521 -0.10859  11.00000  0.03077 
H9    2     0.19253  0.42384 -0.00398  11.00000  0.03066 
H10a  2     0.48635  0.14504 -0.11204  11.00000  0.08690 
H10b  2     0.56792  0.23570 -0.17589  11.00000  0.06390 
H10c  2     0.66466  0.17656 -0.07307  11.00000  0.06443 
H12   2    -0.07973  0.33291  0.28159  11.00000  0.02666 
H13   2    -0.04761  0.27868  0.47053  11.00000  0.03274 
H15   2     0.31476  0.47911  0.56508  11.00000  0.02806 
H16   2     0.28739  0.53714  0.38381  11.00000  0.03163 
H17a  2     0.23864  0.28153  0.67137  11.00000  0.07612 
H17b  2     0.18558  0.38781  0.70051  11.00000  0.08797 
H17c  2     0.06218  0.30816  0.66965  11.00000  0.06931 
HKLF 4

END
;
####################################################################### 
# 
# 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_2bK_17srv155
_database_code_depnum_ccdc_archive 'CCDC 1857924'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_audit_creation_date             2017-06-02
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7

_chemical_name_common            ?
_chemical_name_systematic        
;
2-fluoro-1,3-bis(4'-fluorophenyl)-1,3-propanedione
;
_chemical_formula_moiety         'C15 H9 F3 O2'
_chemical_formula_sum            'C15 H9 F3 O2'
_chemical_formula_weight         278.22
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.3647(4)
_cell_length_b                   11.5018(10)
_cell_length_c                   12.3118(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.065(3)
_cell_angle_gamma                90
_cell_volume                     616.52(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8838
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.04
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.0950 before and 0.0487 after correction. 
The Ratio of minimum to maximum transmission is 0.9479. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13411
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_min         2.426
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3048
_reflns_number_total             3582
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1238 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.044
_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)+(0.0500P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0981
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
F1 F 0.8454(3) 0.50674(13) 0.17025(12) 0.0308(4) Uani 1 1 d . . . . .
F2 F 0.1944(6) 0.5944(2) 0.60479(15) 0.0626(6) Uani 1 1 d . . . . .
F3 F -0.3433(4) 0.36187(15) -0.30295(12) 0.0372(4) Uani 1 1 d . . . . .
O1 O 0.2996(6) 0.29209(17) 0.18721(16) 0.0412(5) Uani 1 1 d . . . . .
O2 O 0.4256(4) 0.62804(14) 0.06813(14) 0.0264(4) Uani 1 1 d . . . . .
C1 C 0.6036(5) 0.4415(2) 0.1230(2) 0.0227(5) Uani 1 1 d . . . . .
C2 C 0.4180(5) 0.3847(2) 0.2096(2) 0.0252(5) Uani 1 1 d . . . . .
C3 C 0.3788(6) 0.4433(2) 0.31561(19) 0.0236(5) Uani 1 1 d . . . . .
C4 C 0.4428(6) 0.5606(2) 0.3341(2) 0.0268(5) Uani 1 1 d . . . . .
C5 C 0.3803(7) 0.6117(2) 0.4321(2) 0.0336(6) Uani 1 1 d . . . . .
C6 C 0.2550(8) 0.5442(3) 0.5089(2) 0.0398(7) Uani 1 1 d . . . . .
C7 C 0.1864(8) 0.4281(3) 0.4939(2) 0.0428(7) Uani 1 1 d . . . . .
C8 C 0.2488(6) 0.3779(3) 0.3962(2) 0.0332(6) Uani 1 1 d . . . . .
C9 C 0.4066(5) 0.5249(2) 0.04911(18) 0.0195(4) Uani 1 1 d . . . . .
C10 C 0.2060(5) 0.47699(19) -0.04208(17) 0.0182(4) Uani 1 1 d . . . . .
C11 C 0.2014(5) 0.35913(19) -0.06942(18) 0.0207(4) Uani 1 1 d . . . . .
C12 C 0.0169(6) 0.3200(2) -0.1576(2) 0.0241(5) Uani 1 1 d . . . . .
C13 C -0.1618(6) 0.3994(2) -0.21625(19) 0.0255(5) Uani 1 1 d . . . . .
C14 C -0.1659(6) 0.5170(2) -0.19158(19) 0.0254(5) Uani 1 1 d . . . . .
C15 C 0.0206(6) 0.55506(19) -0.10377(19) 0.0217(5) Uani 1 1 d . . . . .
H1 H 0.710(6) 0.373(2) 0.0859(19) 0.014(6) Uiso 1 1 d . . . . .
H4 H 0.521(8) 0.605(3) 0.279(3) 0.040(9) Uiso 1 1 d . . . . .
H5 H 0.427(8) 0.697(3) 0.445(3) 0.041(9) Uiso 1 1 d . . . . .
H7 H 0.098(9) 0.383(4) 0.549(3) 0.064(11) Uiso 1 1 d . . . . .
H8 H 0.207(8) 0.301(3) 0.380(3) 0.044(10) Uiso 1 1 d . . . . .
H11 H 0.314(7) 0.307(3) -0.029(2) 0.024(7) Uiso 1 1 d . . . . .
H12 H 0.000(8) 0.240(3) -0.178(3) 0.036(8) Uiso 1 1 d . . . . .
H14 H -0.297(8) 0.567(3) -0.231(2) 0.033(8) Uiso 1 1 d . . . . .
H15 H 0.024(6) 0.636(3) -0.083(2) 0.020(6) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0177(6) 0.0375(9) 0.0369(8) -0.0070(7) -0.0013(6) -0.0025(6)
F2 0.0929(17) 0.0673(15) 0.0298(9) -0.0005(9) 0.0208(10) 0.0065(13)
F3 0.0428(9) 0.0402(9) 0.0275(7) -0.0066(7) -0.0054(6) -0.0031(7)
O1 0.0656(14) 0.0233(9) 0.0343(10) 0.0006(8) -0.0001(9) -0.0152(9)
O2 0.0309(9) 0.0155(8) 0.0335(9) -0.0035(7) 0.0067(7) -0.0054(7)
C1 0.0182(10) 0.0199(11) 0.0297(12) -0.0034(9) -0.0002(9) 0.0025(8)
C2 0.0263(11) 0.0188(11) 0.0292(11) 0.0035(9) -0.0064(9) 0.0005(9)
C3 0.0220(11) 0.0241(11) 0.0236(10) 0.0055(9) -0.0066(9) 0.0003(8)
C4 0.0286(12) 0.0254(12) 0.0263(11) 0.0020(9) 0.0004(9) -0.0025(10)
C5 0.0426(16) 0.0302(14) 0.0276(13) -0.0009(10) 0.0004(11) 0.0009(12)
C6 0.0462(17) 0.0487(18) 0.0244(12) 0.0021(11) 0.0033(11) 0.0059(14)
C7 0.0507(19) 0.0484(18) 0.0295(14) 0.0159(12) 0.0048(13) -0.0050(14)
C8 0.0368(14) 0.0309(14) 0.0310(13) 0.0110(11) -0.0045(10) -0.0054(12)
C9 0.0175(10) 0.0174(10) 0.0245(11) 0.0000(8) 0.0079(8) -0.0013(8)
C10 0.0184(10) 0.0160(10) 0.0212(10) 0.0002(8) 0.0079(8) -0.0005(8)
C11 0.0237(11) 0.0134(10) 0.0257(10) 0.0014(8) 0.0066(9) 0.0019(8)
C12 0.0302(13) 0.0166(11) 0.0261(11) -0.0027(8) 0.0075(9) -0.0016(9)
C13 0.0280(12) 0.0274(13) 0.0216(11) -0.0027(9) 0.0055(9) -0.0033(10)
C14 0.0292(12) 0.0233(11) 0.0241(11) 0.0037(10) 0.0037(9) 0.0039(10)
C15 0.0278(12) 0.0142(10) 0.0240(11) 0.0013(8) 0.0089(9) 0.0017(8)

_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 C1 1.389(3) . ?
F2 C6 1.357(3) . ?
F3 C13 1.354(3) . ?
O1 C2 1.207(3) . ?
O2 C9 1.211(3) . ?
C1 C2 1.531(4) . ?
C1 C9 1.542(3) . ?
C1 H1 1.04(3) . ?
C2 C3 1.489(4) . ?
C3 C4 1.393(3) . ?
C3 C8 1.397(4) . ?
C4 C5 1.386(4) . ?
C4 H4 0.94(4) . ?
C5 C6 1.368(4) . ?
C5 H5 1.01(4) . ?
C6 C7 1.377(5) . ?
C7 C8 1.379(4) . ?
C7 H7 0.95(4) . ?
C8 H8 0.92(4) . ?
C9 C10 1.480(3) . ?
C10 C11 1.397(3) . ?
C10 C15 1.397(3) . ?
C11 C12 1.381(4) . ?
C11 H11 0.90(3) . ?
C12 C13 1.373(4) . ?
C12 H12 0.95(3) . ?
C13 C14 1.386(4) . ?
C14 C15 1.378(3) . ?
C14 H14 0.92(3) . ?
C15 H15 0.96(3) . ?

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
F1 C1 C2 111.29(19) . . ?
F1 C1 C9 106.63(18) . . ?
F1 C1 H1 104.2(14) . . ?
C2 C1 C9 112.12(18) . . ?
C2 C1 H1 104.9(14) . . ?
C9 C1 H1 117.5(13) . . ?
O1 C2 C1 117.2(2) . . ?
O1 C2 C3 121.7(2) . . ?
C3 C2 C1 121.1(2) . . ?
C4 C3 C2 123.2(2) . . ?
C4 C3 C8 119.5(2) . . ?
C8 C3 C2 117.1(2) . . ?
C3 C4 H4 119(2) . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 120(2) . . ?
C4 C5 H5 119.7(18) . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 122.0(18) . . ?
F2 C6 C5 118.2(3) . . ?
F2 C6 C7 118.3(3) . . ?
C5 C6 C7 123.5(3) . . ?
C6 C7 C8 117.9(3) . . ?
C6 C7 H7 122(3) . . ?
C8 C7 H7 120(3) . . ?
C3 C8 H8 117(2) . . ?
C7 C8 C3 120.6(3) . . ?
C7 C8 H8 123(2) . . ?
O2 C9 C1 117.9(2) . . ?
O2 C9 C10 122.7(2) . . ?
C10 C9 C1 119.39(19) . . ?
C11 C10 C9 122.8(2) . . ?
C11 C10 C15 119.7(2) . . ?
C15 C10 C9 117.5(2) . . ?
C10 C11 H11 121.1(18) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 118.7(18) . . ?
C11 C12 H12 123(2) . . ?
C13 C12 C11 118.3(2) . . ?
C13 C12 H12 118(2) . . ?
F3 C13 C12 118.7(2) . . ?
F3 C13 C14 117.9(2) . . ?
C12 C13 C14 123.3(2) . . ?
C13 C14 H14 121(2) . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 H14 121(2) . . ?
C10 C15 H15 118.4(16) . . ?
C14 C15 C10 120.6(2) . . ?
C14 C15 H15 120.9(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
O1 C2 C1 F1 -148.6(2) . . . . ?
O2 C9 C1 F1 -22.2(3) . . . . ?
C1 C2 C3 C4 15.0(3) . . . . ?
C1 C2 C3 C8 -170.1(2) . . . . ?
C1 C9 C10 C11 -4.5(3) . . . . ?
C1 C9 C10 C15 177.0(2) . . . . ?
C2 C1 C9 O2 99.8(2) . . . . ?
C2 C1 C9 C10 -80.8(2) . . . . ?
C3 C2 C1 F1 33.2(3) . . . . ?
C3 C2 C1 C9 -86.2(3) . . . . ?
C4 C3 C2 O1 -163.2(3) . . . . ?
C8 C3 C2 O1 11.7(4) . . . . ?
C9 C1 C2 O1 92.1(3) . . . . ?
C10 C9 C1 F1 157.16(18) . . . . ?
C11 C10 C9 O2 174.9(2) . . . . ?
C15 C10 C9 O2 -3.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details 
;
TITL 17srv155 in P21 #4
REM reset to P21 #4
CELL 0.71073 4.3647 11.5018 12.3118 90 94.0648 90
ZERR 2 0.0004 0.001 0.0011 0 0.0034 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H F O
UNIT 30 18 6 4

L.S. 9
PLAN  5
SIZE 0.04 0.18 0.27
TEMP -153.15
CONF C1 C2 C3 C8
CONF C8 C3 C2 O1
CONF C1 C2 C3 C4
CONF C4 C3 C2 O1
CONF C3 C2 C1 C9
CONF C3 C2 C1 F1
CONF C9 C1 C2 O1
CONF O1 C2 C1 F1
CONF C10 C9 C1 F1
CONF C2 C1 C9 C10
CONF O2 C9 C1 F1
CONF C2 C1 C9 O2
CONF C15 C10 C9 O2
CONF C11 C10 C9 O2
CONF C1 C9 C10 C15
CONF C1 C9 C10 C11
BOND $h
fmap 2
acta 
OMIT -2 60
WGHT 0.05 0.1
FVAR 0.44766
REM <olex2.extras>
REM <HklSrc "%.\\17srv155.hkl">
REM </olex2.extras>

F1    3     0.84543  0.50674  0.17025  11.00000  0.01765  0.03747  0.03691 =
 -0.00699 -0.00130 -0.00254 
F2    3     0.19440  0.59436  0.60479  11.00000  0.09291  0.06735  0.02981 =
 -0.00045  0.02076  0.00650 
F3    3    -0.34332  0.36187 -0.30295  11.00000  0.04279  0.04025  0.02747 =
 -0.00660 -0.00539 -0.00315 
O1    4     0.29957  0.29209  0.18721  11.00000  0.06556  0.02333  0.03429 =
 0.00058 -0.00014 -0.01525 
O2    4     0.42564  0.62804  0.06813  11.00000  0.03088  0.01552  0.03354 =
 -0.00353  0.00673 -0.00536 
C1    1     0.60358  0.44149  0.12303  11.00000  0.01819  0.01989  0.02975 =
 -0.00344 -0.00021  0.00248 
C2    1     0.41803  0.38466  0.20965  11.00000  0.02626  0.01882  0.02919 =
 0.00351 -0.00644  0.00048 
C3    1     0.37883  0.44328  0.31561  11.00000  0.02200  0.02406  0.02360 =
 0.00555 -0.00660  0.00026 
C4    1     0.44279  0.56059  0.33410  11.00000  0.02861  0.02539  0.02626 =
 0.00200  0.00039 -0.00246 
C5    1     0.38027  0.61174  0.43206  11.00000  0.04255  0.03017  0.02763 =
 -0.00091  0.00037  0.00093 
C6    1     0.25499  0.54419  0.50888  11.00000  0.04623  0.04874  0.02440 =
 0.00212  0.00327  0.00594 
C7    1     0.18643  0.42815  0.49392  11.00000  0.05067  0.04835  0.02953 =
 0.01592  0.00478 -0.00503 
C8    1     0.24880  0.37788  0.39622  11.00000  0.03678  0.03093  0.03099 =
 0.01101 -0.00445 -0.00537 
C9    1     0.40658  0.52493  0.04911  11.00000  0.01752  0.01740  0.02450 =
 0.00003  0.00788 -0.00128 
C10   1     0.20603  0.47699 -0.04208  11.00000  0.01845  0.01598  0.02120 =
 0.00016  0.00788 -0.00047 
C11   1     0.20143  0.35913 -0.06942  11.00000  0.02369  0.01336  0.02568 =
 0.00140  0.00659  0.00187 
C12   1     0.01685  0.32000 -0.15763  11.00000  0.03024  0.01656  0.02613 =
 -0.00267  0.00750 -0.00158 
C13   1    -0.16184  0.39944 -0.21625  11.00000  0.02798  0.02742  0.02163 =
 -0.00270  0.00545 -0.00325 
C14   1    -0.16586  0.51701 -0.19158  11.00000  0.02920  0.02325  0.02406 =
 0.00374  0.00374  0.00393 
C15   1     0.02063  0.55506 -0.10377  11.00000  0.02777  0.01419  0.02401 =
 0.00129  0.00887  0.00171 
H1    2     0.70988  0.37298  0.08591  11.00000  0.01397 
H4    2     0.52084  0.60513  0.27864  11.00000  0.03976 
H5    2     0.42685  0.69696  0.44472  11.00000  0.04078 
H7    2     0.09832  0.38350  0.54867  11.00000  0.06442 
H8    2     0.20706  0.30146  0.38006  11.00000  0.04403 
H11   2     0.31447  0.30675 -0.02910  11.00000  0.02379 
H12   2     0.00006  0.24015 -0.17818  11.00000  0.03612 
H14   2    -0.29655  0.56732 -0.23067  11.00000  0.03251 
H15   2     0.02351  0.63582 -0.08260  11.00000  0.01957 
HKLF 4

END
;
####################################################################### 
# 
# 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_17srv156
_database_code_depnum_ccdc_archive 'CCDC 1857928'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_audit_creation_date             2017-06-02
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7

_chemical_name_common            ?
_chemical_name_systematic        
;
2-fluoro-1,3-bis(4-chlorophenyl)-1,3-propanedione
;
_chemical_formula_moiety         'C15 H9 Cl2 F O2'
_chemical_formula_sum            'C15 H9 Cl2 F O2'
_chemical_formula_weight         311.12
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   6.0944(8)
_cell_length_b                   30.676(4)
_cell_length_c                   6.8810(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1286.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.08
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.1246 before and 0.0643 after correction. 
The Ratio of minimum to maximum transmission is 0.9011. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20698
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         2.656
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1529
_reflns_number_total             1750
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1750
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.213
_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)+(0.0250P)²+1.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0971
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.21891(9) 0.53272(2) 0.46128(8) 0.02688(15) Uani 1 1 d . . . . .
F1 F 0.2913(2) 0.7500 0.5406(3) 0.0199(3) Uani 1 2 d S T P . .
O1 O 0.8360(2) 0.70956(4) 0.5317(2) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.5146(4) 0.7500 0.5292(4) 0.0126(5) Uani 1 2 d S T P . .
C2 C 0.6239(3) 0.70978(6) 0.5275(3) 0.0134(3) Uani 1 1 d . . . . .
C3 C 0.5140(3) 0.66687(5) 0.5161(2) 0.0124(3) Uani 1 1 d . . . . .
C4 C 0.3041(3) 0.66130(6) 0.4382(3) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.2144(3) 0.61991(6) 0.4201(3) 0.0155(4) Uani 1 1 d . . . . .
C6 C 0.3345(3) 0.58415(6) 0.4820(3) 0.0160(4) Uani 1 1 d . . . . .
C7 C 0.5434(3) 0.58867(6) 0.5615(3) 0.0163(4) Uani 1 1 d . . . . .
C8 C 0.6325(3) 0.63015(6) 0.5768(3) 0.0144(3) Uani 1 1 d . . . . .
H1 H 0.879(13) 0.7500 0.524(10) 0.15(3) Uiso 1 2 d S T P . .
H4 H 0.224(4) 0.6854(7) 0.391(3) 0.021(6) Uiso 1 1 d . . . . .
H5 H 0.074(3) 0.6160(6) 0.364(3) 0.008(5) Uiso 1 1 d . . . . .
H7 H 0.620(4) 0.5638(8) 0.607(4) 0.027(6) Uiso 1 1 d . . . . .
H8 H 0.769(4) 0.6336(7) 0.635(3) 0.018(5) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0275(3) 0.0149(2) 0.0382(3) -0.00181(19) -0.0001(2) -0.00676(18)
F1 0.0068(6) 0.0147(7) 0.0381(10) 0.000 0.0027(7) 0.000
O1 0.0075(6) 0.0161(6) 0.0318(8) -0.0012(6) -0.0008(5) 0.0012(4)
C1 0.0078(10) 0.0144(11) 0.0157(12) 0.000 0.0013(9) 0.000
C2 0.0103(8) 0.0165(8) 0.0134(8) -0.0001(7) 0.0014(6) -0.0011(6)
C3 0.0119(7) 0.0132(8) 0.0122(8) -0.0006(6) 0.0021(6) -0.0001(6)
C4 0.0121(8) 0.0152(8) 0.0146(8) -0.0005(6) 0.0000(7) 0.0028(6)
C5 0.0122(8) 0.0187(8) 0.0157(8) -0.0016(6) -0.0003(7) -0.0012(7)
C6 0.0183(9) 0.0131(8) 0.0166(9) -0.0014(7) 0.0032(7) -0.0030(6)
C7 0.0177(9) 0.0145(8) 0.0168(9) 0.0011(7) 0.0000(7) 0.0020(7)
C8 0.0126(8) 0.0161(8) 0.0144(9) -0.0004(6) -0.0005(7) 0.0027(7)

_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
Cl1 C6 1.7337(18) . ?
F1 C1 1.363(3) . ?
O1 C2 1.293(2) . ?
O1 H1 1.269(17) . ?
C1 C2 1.402(2) . ?
C1 C2 1.402(2) 8_575 ?
C2 C3 1.479(2) . ?
C3 C4 1.398(2) . ?
C3 C8 1.401(2) . ?
C4 C5 1.388(2) . ?
C4 H4 0.94(2) . ?
C5 C6 1.386(3) . ?
C5 H5 0.95(2) . ?
C6 C7 1.392(3) . ?
C7 C8 1.388(2) . ?
C7 H7 0.95(2) . ?
C8 H8 0.93(2) . ?

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
C2 O1 H1 102(4) . . ?
F1 C1 C2 118.35(11) . 8_575 ?
F1 C1 C2 118.35(11) . . ?
C2 C1 C2 123.3(2) . 8_575 ?
O1 C2 C1 118.65(17) . . ?
O1 C2 C3 116.68(16) . . ?
C1 C2 C3 124.65(17) . . ?
C4 C3 C2 122.91(16) . . ?
C4 C3 C8 119.18(16) . . ?
C8 C3 C2 117.81(16) . . ?
C3 C4 H4 120.6(14) . . ?
C5 C4 C3 120.46(16) . . ?
C5 C4 H4 118.8(14) . . ?
C4 C5 H5 120.7(12) . . ?
C6 C5 C4 119.23(17) . . ?
C6 C5 H5 120.1(12) . . ?
C5 C6 Cl1 118.71(14) . . ?
C5 C6 C7 121.65(16) . . ?
C7 C6 Cl1 119.63(14) . . ?
C6 C7 H7 120.2(15) . . ?
C8 C7 C6 118.63(16) . . ?
C8 C7 H7 121.2(15) . . ?
C3 C8 H8 119.8(13) . . ?
C7 C8 C3 120.85(17) . . ?
C7 C8 H8 119.2(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 1.269(17) 1.269(17) 2.481(3) 156(7) 8_575

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
O1 C7 C6 F1 -19.52(9) . . . . ?
C3 C7 C6 F1 -10.46(6) . . . . ?
C7 C6 C7 O1 -14.17(7) 8_575 . . . ?
C7 C6 C7 C3 -5.11(5) 8_575 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details 
;
TITL 17srv156 in Pnma #62
REM reset to Pnma #62
CELL 0.71073 6.0944 30.6758 6.881 90 90 90
ZERR 4 0.0008 0.0038 0.0009 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM -X,0.5+Y,-Z
SFAC C H Cl F O
UNIT 60 36 8 4 8
EQIV $1 +X,1.5-Y,+Z

L.S. 9
PLAN  5
SIZE 0.03 0.24 0.3
TEMP -153.15
CONF O1 C7 C6 F1
CONF C7_$1 C6 C7 O1
CONF C3 C7 C6 F1
CONF C7_$1 C6 C7 C3
CONF C4 C3 C7 O1
CONF C6 C7 C3 C4
CONF C8 C3 C7 O1
CONF C6 C7 C3 C8
HTAB O1 O1_$1
BOND $h
fmap 2 53
acta 
OMIT -2 58
WGHT 0.025 1.6
FVAR 0.2108
REM <olex2.extras>
REM <HklSrc "%.\\17srv156.hkl">
REM </olex2.extras>

Cl1   3     0.21891  0.53272  0.46128  11.00000  0.02754  0.01489  0.03823 =
 -0.00181 -0.00013 -0.00676 
F1    4     0.29126  0.75000  0.54064  10.50000  0.00685  0.01472  0.03810 =
 0.00000  0.00273  0.00000 
O1    5     0.83601  0.70956  0.53168  11.00000  0.00751  0.01612  0.03175 =
 -0.00118 -0.00076  0.00117 
C1    1     0.51456  0.75000  0.52925  10.50000  0.00782  0.01436  0.01573 =
 0.00000  0.00133  0.00000 
C2    1     0.62387  0.70978  0.52745  11.00000  0.01034  0.01651  0.01336 =
 -0.00014  0.00137 -0.00108 
C3    1     0.51404  0.66687  0.51614  11.00000  0.01193  0.01316  0.01221 =
 -0.00056  0.00211 -0.00008 
C4    1     0.30414  0.66130  0.43820  11.00000  0.01210  0.01523  0.01464 =
 -0.00055 -0.00002  0.00283 
C5    1     0.21438  0.61991  0.42011  11.00000  0.01222  0.01868  0.01569 =
 -0.00159 -0.00027 -0.00120 
C6    1     0.33451  0.58415  0.48201  11.00000  0.01833  0.01305  0.01664 =
 -0.00135  0.00319 -0.00297 
C7    1     0.54337  0.58867  0.56149  11.00000  0.01766  0.01449  0.01679 =
 0.00114 -0.00002  0.00202 
C8    1     0.63248  0.63016  0.57684  11.00000  0.01258  0.01609  0.01442 =
 -0.00044 -0.00049  0.00269 
H1    2     0.87929  0.75000  0.52426  10.50000  0.14637 
H4    2     0.22409  0.68535  0.39149  11.00000  0.02055 
H5    2     0.07430  0.61596  0.36378  11.00000  0.00827 
H7    2     0.62024  0.56384  0.60732  11.00000  0.02687 
H8    2     0.76863  0.63363  0.63535  11.00000  0.01793 
HKLF 4

END
;
#==END

# start Validation Reply Form
_vrf_PLAT355_2cE_17srv145        
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H1       .       1.25 Ang.  
RESPONSE: This is a part of strong symmetrical O-H...O intamolecular
hydrogen bond typical for the disordered enoles.
;
_vrf_PLAT355_17srv156            
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H1       .       1.27 Ang.  
RESPONSE: This is a part of strong symmetrical O-H...O intamolecular
hydrogen bond typical for the disordered enoles.
;
####################################################################### 
# 
# 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_2dE_17srv344
_database_code_depnum_ccdc_archive 'CCDC 1857927'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_audit_creation_date             2017-11-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1

_chemical_name_common            ?
_chemical_name_systematic        
;
2-fluoro-1,3-bis(4-methoxyphenyl)-1,3-propanedione
;
_chemical_formula_moiety         'C17 H15 F O4'
_chemical_formula_sum            'C17 H15 F O4'
_chemical_formula_weight         302.29
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   31.944(2)
_cell_length_b                   7.0229(5)
_cell_length_c                   6.1827(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1387.02(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7326
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.49
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1094 before and 0.0558 after correction. 
The Ratio of minimum to maximum transmission is 0.7836. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.993
_diffrn_reflns_theta_min         2.550
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1661
_reflns_number_total             1880
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 688 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.3700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
F1 F 0.500000 0.7349(3) 0.7129(3) 0.0276(5) Uani 1 2 d S T P . .
O1 O 0.53862(4) 0.7201(2) 0.1754(3) 0.0204(4) Uani 1 1 d . . . . .
H1 H 0.509032 0.713124 0.162060 0.024 Uiso 0.5 1 d R . . A -1
O2 O 0.70077(5) 0.7427(2) 0.7390(3) 0.0186(4) Uani 1 1 d . . . . .
C1 C 0.500000 0.7373(4) 0.4932(5) 0.0158(6) Uani 1 2 d S T P . .
C2 C 0.53852(6) 0.7323(3) 0.3841(3) 0.0143(4) Uani 1 1 d . . . . .
C3 C 0.57973(6) 0.7374(3) 0.4917(4) 0.0134(4) Uani 1 1 d . . . . .
C4 C 0.61396(6) 0.6610(3) 0.3776(4) 0.0151(4) Uani 1 1 d . . . . .
C5 C 0.65358(6) 0.6635(3) 0.4655(4) 0.0156(4) Uani 1 1 d . . . . .
C6 C 0.66025(6) 0.7479(3) 0.6667(4) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.62707(6) 0.8279(3) 0.7811(4) 0.0148(4) Uani 1 1 d . . . . .
C8 C 0.58691(6) 0.8196(3) 0.6934(4) 0.0153(4) Uani 1 1 d . . . . .
C9 C 0.71002(7) 0.8369(4) 0.9374(4) 0.0269(6) Uani 1 1 d . . . . .
H4 H 0.6101(7) 0.603(3) 0.235(4) 0.013(6) Uiso 1 1 d . . . . .
H5 H 0.6769(7) 0.605(4) 0.396(5) 0.018(6) Uiso 1 1 d . . . . .
H7 H 0.6315(6) 0.892(3) 0.918(4) 0.012(6) Uiso 1 1 d . . . . .
H8 H 0.5658(8) 0.879(4) 0.769(5) 0.025(7) Uiso 1 1 d . . . . .
H9A H 0.7386(9) 0.822(4) 0.957(5) 0.029(8) Uiso 1 1 d . . . . .
H9B H 0.7038(7) 0.968(5) 0.932(5) 0.031(8) Uiso 1 1 d . . . . .
H9C H 0.6956(11) 0.780(4) 1.057(6) 0.031(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0160(8) 0.0511(13) 0.0156(10) 0.0014(9) 0.000 0.000
O1 0.0137(7) 0.0335(8) 0.0141(8) -0.0021(8) 0.0005(6) 0.0002(6)
O2 0.0104(6) 0.0255(8) 0.0200(8) -0.0016(5) -0.0007(6) 0.0013(5)
C1 0.0123(12) 0.0208(15) 0.0142(15) 0.0016(11) 0.000 0.000
C2 0.0139(9) 0.0143(10) 0.0148(11) 0.0004(8) -0.0005(8) -0.0002(7)
C3 0.0111(9) 0.0128(9) 0.0164(11) 0.0012(8) 0.0009(7) -0.0004(7)
C4 0.0155(8) 0.0158(10) 0.0140(9) -0.0015(8) 0.0025(8) -0.0004(7)
C5 0.0132(8) 0.0162(9) 0.0175(10) -0.0010(8) 0.0036(8) 0.0010(7)
C6 0.0119(8) 0.0133(9) 0.0185(11) 0.0036(8) 0.0007(8) 0.0000(7)
C7 0.0126(8) 0.0177(9) 0.0140(9) -0.0010(8) 0.0016(8) 0.0002(6)
C8 0.0122(8) 0.0174(9) 0.0162(9) -0.0009(8) 0.0040(8) 0.0013(7)
C9 0.0137(10) 0.0423(16) 0.0246(12) -0.0067(11) -0.0037(9) 0.0012(10)

_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 C1 1.358(4) . ?
O1 H1 0.9501 . ?
O1 C2 1.293(3) . ?
O2 C6 1.370(2) . ?
O2 C9 1.425(3) . ?
C1 C2 1.404(2) 3_655 ?
C1 C2 1.404(2) . ?
C2 C3 1.475(3) . ?
C3 C4 1.408(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.98(3) . ?
C5 C6 1.394(3) . ?
C5 H5 0.95(2) . ?
C6 C7 1.393(3) . ?
C7 C8 1.394(3) . ?
C7 H7 0.97(3) . ?
C8 H8 0.92(3) . ?
C9 H9A 0.93(3) . ?
C9 H9B 0.94(3) . ?
C9 H9C 0.96(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
C2 O1 H1 95.0 . . ?
C6 O2 C9 117.69(17) . . ?
F1 C1 C2 118.71(13) . 3_655 ?
F1 C1 C2 118.71(13) . . ?
C2 C1 C2 122.4(3) 3_655 . ?
O1 C2 C1 118.91(19) . . ?
O1 C2 C3 116.72(18) . . ?
C1 C2 C3 124.36(19) . . ?
C4 C3 C2 117.24(19) . . ?
C8 C3 C2 124.11(18) . . ?
C8 C3 C4 118.59(18) . . ?
C3 C4 H4 120.8(14) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 118.5(14) . . ?
C4 C5 C6 119.85(19) . . ?
C4 C5 H5 122.4(16) . . ?
C6 C5 H5 117.7(16) . . ?
O2 C6 C5 115.10(18) . . ?
O2 C6 C7 124.3(2) . . ?
C7 C6 C5 120.56(18) . . ?
C6 C7 C8 119.07(19) . . ?
C6 C7 H7 121.3(12) . . ?
C8 C7 H7 119.6(12) . . ?
C3 C8 C7 121.14(18) . . ?
C3 C8 H8 121.5(19) . . ?
C7 C8 H8 117.2(19) . . ?
O2 C9 H9A 105(2) . . ?
O2 C9 H9B 112.2(19) . . ?
O2 C9 H9C 112(2) . . ?
H9A C9 H9B 109(2) . . ?
H9A C9 H9C 109(3) . . ?
H9B C9 H9C 110(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O1 0.95 1.53 2.467(3) 170.6 3_655 yes

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
O1 C2 C1 F1 174.8(2) . . . . ?
C1 C2 C3 C4 156.5(2) . . . . ?
C1 C2 C3 C8 -26.3(3) . . . . ?
C2 C1 C2 O1 -0.9(5) 3_655 . . . ?
C2 C1 C2 C3 179.96(16) 3_655 . . . ?
C3 C2 C1 F1 -4.3(4) . . . . ?
C4 C3 C2 O1 -22.6(3) . . . . ?
C5 C6 O2 C9 176.3(2) . . . . ?
C7 C6 O2 C9 -4.5(3) . . . . ?
C8 C3 C2 O1 154.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details 
;
TITL 17srv344 in Cmc21 #36
REM reset to Cmc21 #36
CELL 0.71073 31.9439 7.0229 6.1827 90 90 90
ZERR 4 0.0024 0.0005 0.0005 0 0 0
LATT -7
SYMM -X,-Y,0.5+Z
SYMM -X,+Y,+Z
SYMM +X,-Y,0.5+Z
SFAC C H F O
UNIT 68 60 4 16
EQIV $1 1-X,+Y,+Z

L.S. 9 0 0
PLAN  5
SIZE 0.18 0.27 0.41
TEMP -153.15
HTAB O1 O1_$1
CONF O1 C2 C1 F1
CONF C2_$1 C1 C2 O1
CONF C3 C2 C1 F1
CONF C2_$1 C1 C2 C3
CONF C4 C3 C2 O1
CONF C1 C2 C3 C4
CONF C8 C3 C2 O1
CONF C1 C2 C3 C8
CONF C5 C6 O2 C9
CONF C7 C6 O2 C9
BOND $h
fmap 2 53
acta 
OMIT -2 58
WGHT 0.063 0.37
FVAR 0.2116
REM <olex2.extras>
REM <HklSrc "%.\\17srv344.hkl">
REM </olex2.extras>

F1    3     0.50000  0.73492  0.71293  10.50000  0.01594  0.05112  0.01560 =
 0.00142  0.00000  0.00000 
O1    4     0.53862  0.72008  0.17543  11.00000  0.01372  0.03344  0.01404 =
 -0.00210  0.00050  0.00017 
PART -1
AFIX 3 0.95
H1    2     0.50903  0.71313  0.16206  10.50000 -1.20000 
AFIX 0
PART 0
O2    4     0.70076  0.74275  0.73897  11.00000  0.01043  0.02545  0.01996 =
 -0.00162 -0.00075  0.00134 
C1    1     0.50000  0.73735  0.49323  10.50000  0.01227  0.02078  0.01421 =
 0.00155  0.00000 -0.00000 
C2    1     0.53853  0.73229  0.38406  11.00000  0.01391  0.01433  0.01474 =
 0.00037 -0.00050 -0.00023 
C3    1     0.57973  0.73739  0.49172  11.00000  0.01109  0.01284  0.01638 =
 0.00124  0.00091 -0.00041 
C4    1     0.61396  0.66102  0.37760  11.00000  0.01553  0.01579  0.01402 =
 -0.00155  0.00256 -0.00037 
C5    1     0.65358  0.66351  0.46552  11.00000  0.01315  0.01621  0.01750 =
 -0.00103  0.00357  0.00099 
C6    1     0.66025  0.74794  0.66667  11.00000  0.01193  0.01331  0.01854 =
 0.00360  0.00069  0.00001 
C7    1     0.62707  0.82788  0.78113  11.00000  0.01255  0.01767  0.01401 =
 -0.00104  0.00162  0.00017 
C8    1     0.58691  0.81960  0.69341  11.00000  0.01219  0.01743  0.01622 =
 -0.00090  0.00399  0.00132 
C9    1     0.71002  0.83691  0.93739  11.00000  0.01369  0.04229  0.02456 =
 -0.00666 -0.00370  0.00122 
H4    2     0.61009  0.60299  0.23530  11.00000  0.01344 
H5    2     0.67692  0.60461  0.39627  11.00000  0.01847 
H7    2     0.63151  0.89232  0.91834  11.00000  0.01240 
H8    2     0.56580  0.87883  0.76945  11.00000  0.02513 
H9a   2     0.73864  0.82218  0.95664  11.00000  0.02881 
H9b   2     0.70379  0.96815  0.93162  11.00000  0.03107 
H9c   2     0.69556  0.77981  1.05740  11.00000  0.03089 
HKLF 4

END
;
####################################################################### 
# 
# 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_2bE_17srv148
_database_code_depnum_ccdc_archive 'CCDC 1857923'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_audit_creation_date             2017-05-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7

_chemical_name_common            ?
_chemical_name_systematic        
;
2-fluoro-1,3-bis(4'-fluorophenyl)-1,3-propanedione
;
_chemical_formula_moiety         'C15 H9 F3 O2'
_chemical_formula_sum            'C15 H9 F3 O2'
_chemical_formula_weight         278.22
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   28.403(2)
_cell_length_b                   6.1029(4)
_cell_length_c                   6.9953(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.753(3)
_cell_angle_gamma                90
_cell_volume                     1182.67(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8961
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.51
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.0912 before and 0.0542 after correction. 
The Ratio of minimum to maximum transmission is 0.9068. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12032
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_min         2.941
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1450
_reflns_number_total             1724
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1724
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+0.9400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H1(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
F1 F 0.5000 0.60836(17) 0.7500 0.0284(3) Uani 1 2 d S T P . .
F2 F 0.72449(3) 0.57477(16) 0.77084(13) 0.0305(2) Uani 1 1 d . . . . .
O1 O 0.54377(3) 1.15294(15) 0.75769(14) 0.0192(2) Uani 1 1 d . . . . .
C1 C 0.5000 0.8309(3) 0.7500 0.0149(3) Uani 1 2 d S T P . .
C2 C 0.54361(4) 0.94124(19) 0.75475(17) 0.0133(2) Uani 1 1 d . . . . .
C3 C 0.59048(4) 0.83311(18) 0.76082(16) 0.0129(2) Uani 1 1 d . . . . .
C4 C 0.59483(4) 0.62394(19) 0.68482(17) 0.0149(2) Uani 1 1 d . . . . .
C5 C 0.64018(4) 0.5371(2) 0.68757(18) 0.0173(3) Uani 1 1 d . . . . .
C6 C 0.68035(4) 0.6605(2) 0.76785(18) 0.0190(3) Uani 1 1 d . . . . .
C7 C 0.67775(4) 0.8676(2) 0.84508(18) 0.0187(3) Uani 1 1 d . . . . .
C8 C 0.63234(4) 0.95382(19) 0.84025(17) 0.0152(2) Uani 1 1 d . . . . .
H1 H 0.5152(10) 1.190(6) 0.756(6) 0.024(9) Uiso 0.5 1 d . . . . .
H4 H 0.5672(5) 0.538(3) 0.628(2) 0.022(4) Uiso 1 1 d . . . . .
H5 H 0.6439(6) 0.394(3) 0.633(3) 0.033(5) Uiso 1 1 d . . . . .
H7 H 0.7060(6) 0.949(3) 0.903(3) 0.033(5) Uiso 1 1 d . . . . .
H8 H 0.6289(5) 1.095(3) 0.893(2) 0.021(4) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0218(5) 0.0065(5) 0.0609(9) 0.000 0.0179(5) 0.000
F2 0.0163(4) 0.0383(5) 0.0379(5) -0.0036(4) 0.0081(3) 0.0078(3)
O1 0.0182(4) 0.0089(4) 0.0295(5) -0.0004(3) 0.0026(4) -0.0009(3)
C1 0.0171(7) 0.0064(6) 0.0212(8) 0.000 0.0047(6) 0.000
C2 0.0157(5) 0.0106(5) 0.0128(5) 0.0004(4) 0.0018(4) 0.0001(4)
C3 0.0147(5) 0.0115(5) 0.0130(5) 0.0011(4) 0.0040(4) -0.0008(4)
C4 0.0167(5) 0.0130(5) 0.0153(5) -0.0001(4) 0.0044(4) -0.0006(4)
C5 0.0206(6) 0.0155(5) 0.0175(6) 0.0002(4) 0.0075(4) 0.0026(4)
C6 0.0156(5) 0.0244(6) 0.0183(6) 0.0029(5) 0.0068(4) 0.0043(4)
C7 0.0150(5) 0.0234(6) 0.0179(6) 0.0002(5) 0.0035(4) -0.0030(4)
C8 0.0176(5) 0.0139(5) 0.0144(5) 0.0001(4) 0.0043(4) -0.0029(4)

_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 C1 1.3581(18) . ?
F2 C6 1.3546(13) . ?
O1 C2 1.2922(14) . ?
O1 H1 0.84(3) . ?
C1 C2 1.4039(13) . ?
C1 C2 1.4039(13) 2_656 ?
C2 C3 1.4781(15) . ?
C3 C4 1.3988(16) . ?
C3 C8 1.4047(15) . ?
C4 C5 1.3891(16) . ?
C4 H4 0.957(16) . ?
C5 C6 1.3789(18) . ?
C5 H5 0.97(2) . ?
C6 C7 1.3831(18) . ?
C7 C8 1.3864(16) . ?
C7 H7 0.957(18) . ?
C8 H8 0.953(18) . ?

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
C2 O1 H1 105(2) . . ?
F1 C1 C2 118.66(7) . 2_656 ?
F1 C1 C2 118.66(7) . . ?
C2 C1 C2 122.67(14) . 2_656 ?
O1 C2 C1 118.69(11) . . ?
O1 C2 C3 116.48(10) . . ?
C1 C2 C3 124.82(11) . . ?
C4 C3 C2 123.44(10) . . ?
C4 C3 C8 119.41(10) . . ?
C8 C3 C2 117.10(10) . . ?
C3 C4 H4 121.8(10) . . ?
C5 C4 C3 120.16(11) . . ?
C5 C4 H4 118.0(10) . . ?
C4 C5 H5 121.3(10) . . ?
C6 C5 C4 118.59(11) . . ?
C6 C5 H5 120.1(10) . . ?
F2 C6 C5 118.37(12) . . ?
F2 C6 C7 118.42(11) . . ?
C5 C6 C7 123.20(11) . . ?
C6 C7 C8 117.83(11) . . ?
C6 C7 H7 122.0(11) . . ?
C8 C7 H7 120.2(11) . . ?
C3 C8 H8 118.6(9) . . ?
C7 C8 C3 120.81(11) . . ?
C7 C8 H8 120.6(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.84(3) 1.67(3) 2.4652(18) 157(3) 2_656

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
O1 C2 C1 F1 -178.98(8) . . . . ?
C1 C2 C3 C4 27.08(17) . . . . ?
C1 C2 C3 C8 -155.71(10) . . . . ?
C2 C1 C2 O1 1.02(8) 2_656 . . . ?
C2 C1 C2 C3 179.69(12) 2_656 . . . ?
C3 C2 C1 F1 -0.31(12) . . . . ?
C4 C3 C2 O1 -154.22(12) . . . . ?
C8 C3 C2 O1 22.99(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_insrtructions_details 
;
TITL 17srv148 in C2/c #15
REM reset to C2/c #15
CELL 0.71073 28.4034 6.1029 6.9953 90 102.7534 90
ZERR 4 0.0021 0.0004 0.0005 0 0.0029 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H F O
UNIT 60 36 12 8
EQIV $1 1-X,+Y,1.5-Z

L.S. 9
PLAN  5
SIZE 0.09 0.22 0.28
TEMP -153.15
HTAB O1 O1_$1
CONF O1 C2 C1 F1
CONF C2_$1 C1 C2 O1
CONF C3 C2 C1 F1
CONF C2_$1 C1 C2 C3
CONF C4 C3 C2 O1
CONF C1 C2 C3 C4
CONF C8 C3 C2 O1
CONF C1 C2 C3 C8
BOND $h
fmap 2
acta 
OMIT -2 60
WGHT 0.07 0.94
FVAR 0.23304
REM <olex2.extras>
REM <HklSrc "%.\\17srv148.hkl">
REM </olex2.extras>

F1    3     0.50000  0.60836  0.75000  10.50000  0.02180  0.00654  0.06092 =
 -0.00000  0.01794 -0.00000 
F2    3     0.72449  0.57477  0.77084  11.00000  0.01626  0.03834  0.03788 =
 -0.00361  0.00812  0.00783 
O1    4     0.54378  1.15294  0.75769  11.00000  0.01817  0.00887  0.02946 =
 -0.00042  0.00261 -0.00088 
C1    1     0.50000  0.83089  0.75000  10.50000  0.01711  0.00642  0.02122 =
 -0.00000  0.00466 -0.00000 
C2    1     0.54361  0.94124  0.75475  11.00000  0.01572  0.01063  0.01278 =
 0.00036  0.00179  0.00014 
C3    1     0.59049  0.83312  0.76082  11.00000  0.01472  0.01151  0.01304 =
 0.00112  0.00400 -0.00079 
C4    1     0.59483  0.62394  0.68482  11.00000  0.01670  0.01295  0.01532 =
 -0.00014  0.00438 -0.00056 
C5    1     0.64018  0.53708  0.68757  11.00000  0.02060  0.01548  0.01748 =
 0.00019  0.00748  0.00259 
C6    1     0.68035  0.66049  0.76785  11.00000  0.01557  0.02445  0.01827 =
 0.00294  0.00678  0.00432 
C7    1     0.67775  0.86763  0.84508  11.00000  0.01498  0.02338  0.01785 =
 0.00021  0.00353 -0.00303 
C8    1     0.63234  0.95382  0.84025  11.00000  0.01765  0.01386  0.01440 =
 0.00006  0.00425 -0.00289 
H1    2     0.51524  1.18952  0.75564  10.50000  0.02384 
H4    2     0.56717  0.53761  0.62785  11.00000  0.02172 
H5    2     0.64386  0.39412  0.63336  11.00000  0.03263 
H7    2     0.70604  0.94949  0.90276  11.00000  0.03267 
H8    2     0.62890  1.09545  0.89285  11.00000  0.02102 
HKLF 4

END
;
