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

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

data_yjs-sdn-1826
_audit_block_doi                 10.5517/cc1kgjg0
_database_code_depnum_ccdc_archive 'CCDC 1443932'
_audit_update_record             
;
2015-12-23 deposited with the CCDC.
2016-01-28 downloaded from the CCDC.
;
_audit_creation_date             2015-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.27
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   13.8731(10)
_cell_length_b                   8.1105(5)
_cell_length_c                   23.2586(18)
_cell_angle_alpha                90
_cell_angle_beta                 111.782(9)
_cell_angle_gamma                90
_cell_volume                     2430.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2529
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      72.4240
_cell_measurement_theta_min      5.4840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5563
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         6.369
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   91.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   91.00  176.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00  109.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   98.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00  109.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   98.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 15 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   90.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0845757000
_diffrn_orient_matrix_UB_12      0.0239814000
_diffrn_orient_matrix_UB_13      0.0647018000
_diffrn_orient_matrix_UB_21      0.0836501000
_diffrn_orient_matrix_UB_22      0.0035877000
_diffrn_orient_matrix_UB_23      -0.0288640000
_diffrn_orient_matrix_UB_31      -0.0123982000
_diffrn_orient_matrix_UB_32      0.1884418000
_diffrn_orient_matrix_UB_33      -0.0077253000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1941
_reflns_number_total             2176
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.052
_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)+(0.1122P)²+1.3254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1649
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G)
2.b Idealised Me refined as rotating group:
 C00E(H00A,H00B,H00E), C00H(H00H,H00I,H00J), C00I(H00K,H00L,H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O001 O 0.38162(10) 0.47606(17) 0.26661(6) 0.0344(4) Uani 1 1 d . . . . .
O002 O 0.51104(10) 0.28676(16) 0.37514(6) 0.0350(4) Uani 1 1 d . . . . .
C003 C 0.35516(12) 0.3992(2) 0.45930(8) 0.0244(4) Uani 1 1 d . . . . .
C004 C 0.44122(13) 0.3155(2) 0.45581(8) 0.0256(4) Uani 1 1 d . . . . .
C005 C 0.44533(13) 0.3408(2) 0.39330(8) 0.0263(4) Uani 1 1 d . . . . .
C006 C 0.34060(13) 0.4042(2) 0.51536(8) 0.0267(4) Uani 1 1 d . . . . .
C007 C 0.29727(13) 0.4735(2) 0.39748(8) 0.0254(4) Uani 1 1 d . . . . .
C008 C 0.41082(14) 0.3151(2) 0.56472(8) 0.0285(4) Uani 1 1 d . . . . .
H008 H 0.4009 0.3148 0.6030 0.034 Uiso 1 1 calc R . . . .
C009 C 0.35248(13) 0.4420(2) 0.35877(8) 0.0261(4) Uani 1 1 d . . . . .
C00A C 0.31897(14) 0.5035(2) 0.29871(8) 0.0285(4) Uani 1 1 d . . . . .
C00B C 0.49426(13) 0.2269(2) 0.56094(8) 0.0291(4) Uani 1 1 d . . . . .
C00C C 0.50981(13) 0.2299(2) 0.50513(8) 0.0282(4) Uani 1 1 d . . . . .
H00C H 0.5670 0.1735 0.5012 0.034 Uiso 1 1 calc R . . . .
C00D C 0.20415(14) 0.5599(2) 0.37493(9) 0.0304(4) Uani 1 1 d . . . . .
H00D H 0.1655 0.5809 0.4004 0.036 Uiso 1 1 calc R . . . .
C00E C 0.25618(15) 0.5024(2) 0.52519(9) 0.0316(4) Uani 1 1 d . . . . .
H00A H 0.2639 0.6191 0.5168 0.047 Uiso 1 1 calc GR . . . .
H00B H 0.2612 0.4895 0.5681 0.047 Uiso 1 1 calc GR . . . .
H00E H 0.1884 0.4627 0.4970 0.047 Uiso 1 1 calc GR . . . .
C00F C 0.22467(15) 0.5893(2) 0.27573(9) 0.0335(5) Uani 1 1 d . . . . .
H00F H 0.1989 0.6296 0.2344 0.040 Uiso 1 1 calc R . . . .
C00G C 0.16929(14) 0.6146(2) 0.31378(9) 0.0342(5) Uani 1 1 d . . . . .
H00G H 0.1050 0.6717 0.2975 0.041 Uiso 1 1 calc R . . . .
C00H C 0.56584(15) 0.1323(2) 0.61574(9) 0.0363(5) Uani 1 1 d . . . . .
H00H H 0.6359 0.1787 0.6287 0.054 Uiso 1 1 calc GR . . . .
H00I H 0.5673 0.0164 0.6043 0.054 Uiso 1 1 calc GR . . . .
H00J H 0.5409 0.1403 0.6499 0.054 Uiso 1 1 calc GR . . . .
C00I C 0.35374(18) 0.5486(3) 0.20676(9) 0.0430(5) Uani 1 1 d . . . . .
H00K H 0.2852 0.5085 0.1799 0.064 Uiso 1 1 calc GR . . . .
H00L H 0.4051 0.5182 0.1889 0.064 Uiso 1 1 calc GR . . . .
H00M H 0.3518 0.6688 0.2103 0.064 Uiso 1 1 calc GR . . . .


_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
O001 C00A 1.358(2) . ?
O001 C00I 1.426(2) . ?
O002 C005 1.220(2) . ?
C003 C004 1.402(2) . ?
C003 C006 1.392(2) . ?
C003 C007 1.489(2) . ?
C004 C005 1.490(2) . ?
C004 C00C 1.376(2) . ?
C005 C009 1.486(2) . ?
C006 C008 1.400(3) . ?
C006 C00E 1.502(2) . ?
C007 C009 1.405(2) . ?
C007 C00D 1.390(2) . ?
C008 H008 0.9500 . ?
C008 C00B 1.391(3) . ?
C009 C00A 1.391(3) . ?
C00A C00F 1.401(3) . ?
C00B C00C 1.393(3) . ?
C00B C00H 1.503(3) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9500 . ?
C00D C00G 1.394(3) . ?
C00E H00A 0.9800 . ?
C00E H00B 0.9800 . ?
C00E H00E 0.9800 . ?
C00F H00F 0.9500 . ?
C00F C00G 1.386(3) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9800 . ?
C00H H00I 0.9800 . ?
C00H H00J 0.9800 . ?
C00I H00K 0.9800 . ?
C00I H00L 0.9800 . ?
C00I H00M 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
C00A O001 C00I 118.16(16) . . ?
C004 C003 C007 107.80(14) . . ?
C006 C003 C004 119.41(16) . . ?
C006 C003 C007 132.74(16) . . ?
C003 C004 C005 109.37(15) . . ?
C00C C004 C003 122.45(16) . . ?
C00C C004 C005 128.15(16) . . ?
O002 C005 C004 126.33(17) . . ?
O002 C005 C009 128.36(17) . . ?
C009 C005 C004 105.30(14) . . ?
C003 C006 C008 117.03(16) . . ?
C003 C006 C00E 123.37(16) . . ?
C008 C006 C00E 119.58(16) . . ?
C009 C007 C003 108.55(14) . . ?
C00D C007 C003 131.37(16) . . ?
C00D C007 C009 120.08(16) . . ?
C006 C008 H008 118.1 . . ?
C00B C008 C006 123.78(16) . . ?
C00B C008 H008 118.1 . . ?
C007 C009 C005 108.87(15) . . ?
C00A C009 C005 129.81(16) . . ?
C00A C009 C007 121.32(16) . . ?
O001 C00A C009 116.74(16) . . ?
O001 C00A C00F 124.71(17) . . ?
C009 C00A C00F 118.55(17) . . ?
C008 C00B C00C 118.05(16) . . ?
C008 C00B C00H 120.81(17) . . ?
C00C C00B C00H 121.14(17) . . ?
C004 C00C C00B 119.16(16) . . ?
C004 C00C H00C 120.4 . . ?
C00B C00C H00C 120.4 . . ?
C007 C00D H00D 121.1 . . ?
C007 C00D C00G 117.88(17) . . ?
C00G C00D H00D 121.1 . . ?
C006 C00E H00A 109.5 . . ?
C006 C00E H00B 109.5 . . ?
C006 C00E H00E 109.5 . . ?
H00A C00E H00B 109.5 . . ?
H00A C00E H00E 109.5 . . ?
H00B C00E H00E 109.5 . . ?
C00A C00F H00F 120.3 . . ?
C00G C00F C00A 119.40(17) . . ?
C00G C00F H00F 120.3 . . ?
C00D C00G H00G 118.7 . . ?
C00F C00G C00D 122.65(17) . . ?
C00F C00G H00G 118.7 . . ?
C00B C00H H00H 109.5 . . ?
C00B C00H H00I 109.5 . . ?
C00B C00H H00J 109.5 . . ?
H00H C00H H00I 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 109.5 . . ?
O001 C00I H00K 109.5 . . ?
O001 C00I H00L 109.5 . . ?
O001 C00I H00M 109.5 . . ?
H00K C00I H00L 109.5 . . ?
H00K C00I H00M 109.5 . . ?
H00L C00I H00M 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
O001 C00A C00F C00G -177.64(17) . . . . ?
O002 C005 C009 C007 178.75(17) . . . . ?
O002 C005 C009 C00A -2.0(3) . . . . ?
C003 C004 C005 O002 179.03(17) . . . . ?
C003 C004 C005 C009 -1.89(18) . . . . ?
C003 C004 C00C C00B -0.6(3) . . . . ?
C003 C006 C008 C00B 1.6(3) . . . . ?
C003 C007 C009 C005 2.26(19) . . . . ?
C003 C007 C009 C00A -177.08(15) . . . . ?
C003 C007 C00D C00G -179.91(17) . . . . ?
C004 C003 C006 C008 -3.8(2) . . . . ?
C004 C003 C006 C00E 174.64(15) . . . . ?
C004 C003 C007 C009 -3.46(18) . . . . ?
C004 C003 C007 C00D 175.70(18) . . . . ?
C004 C005 C009 C007 -0.31(19) . . . . ?
C004 C005 C009 C00A 178.96(17) . . . . ?
C005 C004 C00C C00B 177.21(16) . . . . ?
C005 C009 C00A O001 -3.7(3) . . . . ?
C005 C009 C00A C00F 176.66(17) . . . . ?
C006 C003 C004 C005 -174.71(15) . . . . ?
C006 C003 C004 C00C 3.5(2) . . . . ?
C006 C003 C007 C009 174.12(17) . . . . ?
C006 C003 C007 C00D -6.7(3) . . . . ?
C006 C008 C00B C00C 1.2(3) . . . . ?
C006 C008 C00B C00H -179.29(16) . . . . ?
C007 C003 C004 C005 3.25(18) . . . . ?
C007 C003 C004 C00C -178.55(16) . . . . ?
C007 C003 C006 C008 178.82(16) . . . . ?
C007 C003 C006 C00E -2.7(3) . . . . ?
C007 C009 C00A O001 175.45(15) . . . . ?
C007 C009 C00A C00F -4.2(3) . . . . ?
C007 C00D C00G C00F -1.4(3) . . . . ?
C008 C00B C00C C004 -1.7(3) . . . . ?
C009 C007 C00D C00G -0.8(3) . . . . ?
C009 C00A C00F C00G 1.9(3) . . . . ?
C00A C00F C00G C00D 0.8(3) . . . . ?
C00C C004 C005 O002 1.0(3) . . . . ?
C00C C004 C005 C009 -179.95(17) . . . . ?
C00D C007 C009 C005 -177.02(16) . . . . ?
C00D C007 C009 C00A 3.6(3) . . . . ?
C00E C006 C008 C00B -176.92(16) . . . . ?
C00H C00B C00C C004 178.80(16) . . . . ?
C00I O001 C00A C009 -175.13(16) . . . . ?
C00I O001 C00A C00F 4.5(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-11
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_yjs-sdn
_audit_block_doi                 10.5517/cc1kglsd
_database_code_depnum_ccdc_archive 'CCDC 1444004'
_audit_update_record             
;
2015-12-23 deposited with the CCDC.
2016-01-28 downloaded from the CCDC.
;
_audit_creation_date             2015-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 F2 O2'
_chemical_formula_sum            'C14 H8 F2 O2'
_chemical_formula_weight         246.20
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2744(3)
_cell_length_b                   11.9968(5)
_cell_length_c                   12.4989(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.099(4)
_cell_angle_gamma                90
_cell_volume                     1077.04(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3041
_cell_measurement_temperature    285.16(10)
_cell_measurement_theta_max      26.7620
_cell_measurement_theta_min      3.7060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12874
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         3.396
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      285.16(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -53.00   42.00   1.0000   11.3550
omega____ theta____ kappa____ phi______ frames
    -       14.9013  -77.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   82.00   1.0000   11.3550
omega____ theta____ kappa____ phi______ frames
    -       14.9013   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   -2.00   82.00   1.0000   11.3550
omega____ theta____ kappa____ phi______ frames
    -       14.9013   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   82.00   1.0000   11.3550
omega____ theta____ kappa____ phi______ frames
    -       14.9013   57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   82.00   1.0000   11.3550
omega____ theta____ kappa____ phi______ frames
    -       14.9013   57.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega  -83.00    1.00   1.0000   11.3550
omega____ theta____ kappa____ phi______ frames
    -      -15.9950  -57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega  -52.00   24.00   1.0000   11.3550
omega____ theta____ kappa____ phi______ frames
    -       14.9013  -57.0000  150.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0091425000
_diffrn_orient_matrix_UB_12      0.0534084000
_diffrn_orient_matrix_UB_13      -0.0245983000
_diffrn_orient_matrix_UB_21      -0.0197049000
_diffrn_orient_matrix_UB_22      -0.0253424000
_diffrn_orient_matrix_UB_23      -0.0518305000
_diffrn_orient_matrix_UB_31      -0.0963090000
_diffrn_orient_matrix_UB_32      0.0001087000
_diffrn_orient_matrix_UB_33      0.0036517000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1719
_reflns_number_total             2195
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.066
_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)+(0.0816P)²+0.3884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1597
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00I(H00A,H00G,H00H)
;
_atom_sites_solution_hydrogens   geom
_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
O001 O 0.2317(2) 0.78703(12) 0.59376(12) 0.0541(4) Uani 1 1 d . . . . .
F002 F 0.3241(3) 0.12559(11) 0.43241(14) 0.0785(5) Uani 1 1 d . . . . .
O003 O 0.3791(2) 0.58015(14) 0.71158(12) 0.0603(5) Uani 1 1 d . . . . .
F004 F 0.4730(2) 0.14054(13) 0.63915(14) 0.0828(5) Uani 1 1 d . . . . .
C005 C 0.2345(3) 0.60575(16) 0.52331(15) 0.0377(5) Uani 1 1 d . . . . .
C006 C 0.1957(3) 0.53079(17) 0.43658(16) 0.0387(5) Uani 1 1 d . . . . .
C007 C 0.2605(3) 0.41875(16) 0.47557(16) 0.0391(5) Uani 1 1 d . . . . .
C008 C 0.3379(3) 0.42655(16) 0.58480(16) 0.0404(5) Uani 1 1 d . . . . .
C009 C 0.3256(3) 0.54490(17) 0.62097(16) 0.0409(5) Uani 1 1 d . . . . .
C00A C 0.1893(3) 0.71843(17) 0.50823(16) 0.0411(5) Uani 1 1 d . . . . .
C00B C 0.1124(3) 0.56480(18) 0.33566(17) 0.0466(5) Uani 1 1 d . . . . .
H00B H 0.0879 0.5146 0.2785 0.056 Uiso 1 1 calc R . . . .
C00C C 0.1034(3) 0.75278(18) 0.40504(17) 0.0460(5) Uani 1 1 d . . . . .
H00C H 0.0715 0.8273 0.3928 0.055 Uiso 1 1 calc R . . . .
C00D C 0.4116(3) 0.33405(19) 0.64335(18) 0.0493(5) Uani 1 1 d . . . . .
H00D H 0.4633 0.3395 0.7161 0.059 Uiso 1 1 calc R . . . .
C00E C 0.2541(3) 0.31778(18) 0.42226(19) 0.0494(5) Uani 1 1 d . . . . .
H00E H 0.2025 0.3115 0.3495 0.059 Uiso 1 1 calc R . . . .
C00F C 0.0658(3) 0.6769(2) 0.32181(18) 0.0504(6) Uani 1 1 d . . . . .
H00F H 0.0076 0.7013 0.2543 0.060 Uiso 1 1 calc R . . . .
C00G C 0.4046(3) 0.23453(18) 0.5893(2) 0.0526(6) Uani 1 1 d . . . . .
C00H C 0.3273(3) 0.22648(18) 0.4813(2) 0.0540(6) Uani 1 1 d . . . . .
C00I C 0.1987(4) 0.90336(19) 0.5779(2) 0.0668(7) Uani 1 1 d . . . . .
H00A H 0.2651 0.9299 0.5224 0.100 Uiso 1 1 calc GR . . . .
H00G H 0.2411 0.9424 0.6443 0.100 Uiso 1 1 calc GR . . . .
H00H H 0.0679 0.9162 0.5563 0.100 Uiso 1 1 calc GR . . . .


_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
O001 C00A 1.346(2) . ?
O001 C00I 1.425(3) . ?
F002 C00H 1.354(3) . ?
O003 C009 1.214(2) . ?
F004 C00G 1.345(2) . ?
C005 C006 1.402(3) . ?
C005 C009 1.486(3) . ?
C005 C00A 1.397(3) . ?
C006 C007 1.481(3) . ?
C006 C00B 1.372(3) . ?
C007 C008 1.395(3) . ?
C007 C00E 1.380(3) . ?
C008 C009 1.497(3) . ?
C008 C00D 1.389(3) . ?
C00A C00C 1.403(3) . ?
C00B H00B 0.9300 . ?
C00B C00F 1.391(3) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.377(3) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.369(3) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.379(3) . ?
C00F H00F 0.9300 . ?
C00G C00H 1.382(4) . ?
C00I H00A 0.9600 . ?
C00I H00G 0.9600 . ?
C00I H00H 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A O001 C00I 118.43(18) . . ?
C006 C005 C009 109.22(18) . . ?
C00A C005 C006 120.14(18) . . ?
C00A C005 C009 130.64(18) . . ?
C005 C006 C007 108.25(17) . . ?
C00B C006 C005 121.70(19) . . ?
C00B C006 C007 130.06(19) . . ?
C008 C007 C006 108.61(17) . . ?
C00E C007 C006 130.78(19) . . ?
C00E C007 C008 120.60(19) . . ?
C007 C008 C009 108.97(17) . . ?
C00D C008 C007 121.61(19) . . ?
C00D C008 C009 129.4(2) . . ?
O003 C009 C005 129.12(19) . . ?
O003 C009 C008 125.92(18) . . ?
C005 C009 C008 104.95(16) . . ?
O001 C00A C005 117.73(18) . . ?
O001 C00A C00C 124.29(19) . . ?
C005 C00A C00C 117.99(19) . . ?
C006 C00B H00B 121.1 . . ?
C006 C00B C00F 117.7(2) . . ?
C00F C00B H00B 121.1 . . ?
C00A C00C H00C 119.8 . . ?
C00F C00C C00A 120.4(2) . . ?
C00F C00C H00C 119.8 . . ?
C008 C00D H00D 121.4 . . ?
C00G C00D C008 117.1(2) . . ?
C00G C00D H00D 121.4 . . ?
C007 C00E H00E 121.4 . . ?
C00H C00E C007 117.3(2) . . ?
C00H C00E H00E 121.4 . . ?
C00B C00F H00F 119.0 . . ?
C00C C00F C00B 122.0(2) . . ?
C00C C00F H00F 119.0 . . ?
F004 C00G C00D 121.4(2) . . ?
F004 C00G C00H 117.2(2) . . ?
C00D C00G C00H 121.4(2) . . ?
F002 C00H C00E 119.4(2) . . ?
F002 C00H C00G 118.6(2) . . ?
C00E C00H C00G 122.0(2) . . ?
O001 C00I H00A 109.5 . . ?
O001 C00I H00G 109.5 . . ?
O001 C00I H00H 109.5 . . ?
H00A C00I H00G 109.5 . . ?
H00A C00I H00H 109.5 . . ?
H00G C00I H00H 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-29
_olex2_submission_special_instructions 'No special instructions were received'
