# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2014

####################################################################### 
# 
# 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_wa1460
_database_code_depnum_ccdc_archive 'CCDC 1002047'
_audit_update_record             
;
2014-05-08 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 O4, C12 F4 N4'
_chemical_formula_sum            'C32 H18 F4 N4 O4'
_chemical_formula_weight         598.50

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8078(13)
_cell_length_b                   10.6592(18)
_cell_length_c                   10.840(2)
_cell_angle_alpha                61.373(13)
_cell_angle_beta                 71.958(14)
_cell_angle_gamma                84.063(14)
_cell_volume                     655.6(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3415
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.9

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             306
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9520
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5551
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_sigmaI/netI    0.0934
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2305
_reflns_number_gt                1500
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0693P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2305
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1544(4) 0.3357(2) 0.9238(2) 0.0400(6) Uani 1 1 d . . .
O2 O 0.2199(3) 0.3668(2) 0.2083(2) 0.0334(5) Uani 1 1 d . . .
C1 C -0.0489(4) 0.3445(3) 0.6902(3) 0.0233(6) Uani 1 1 d . . .
C2 C 0.0091(4) 0.4249(3) 0.5340(3) 0.0218(6) Uani 1 1 d . . .
C3 C 0.0854(4) 0.3540(3) 0.4477(3) 0.0250(6) Uani 1 1 d . . .
C4 C 0.1010(5) 0.2053(3) 0.5178(3) 0.0295(7) Uani 1 1 d . . .
H4 H 0.1549 0.1571 0.4609 0.035 Uiso 1 1 calc R . .
C5 C 0.0384(5) 0.1290(3) 0.6690(3) 0.0315(7) Uani 1 1 d . . .
H5 H 0.0466 0.0280 0.7154 0.038 Uiso 1 1 calc R . .
C6 C -0.0365(5) 0.1965(3) 0.7551(3) 0.0282(7) Uani 1 1 d . . .
H6 H -0.0798 0.1412 0.8594 0.034 Uiso 1 1 calc R . .
C7 C -0.1216(4) 0.4189(3) 0.7766(3) 0.0259(6) Uani 1 1 d . . .
C8 C -0.3498(5) 0.3357(4) 1.0227(4) 0.0465(9) Uani 1 1 d . . .
H8A H -0.3519 0.4183 1.0396 0.070 Uiso 1 1 calc R . .
H8B H -0.3718 0.2473 1.1164 0.070 Uiso 1 1 calc R . .
H8C H -0.4600 0.3414 0.9799 0.070 Uiso 1 1 calc R . .
C9 C 0.1410(4) 0.4375(3) 0.2901(3) 0.0266(6) Uani 1 1 d . . .
C10 C 0.0673(6) 0.3168(4) 0.1744(4) 0.0466(9) Uani 1 1 d . . .
H10A H -0.0276 0.2455 0.2657 0.070 Uiso 1 1 calc R . .
H10B H 0.1352 0.2732 0.1114 0.070 Uiso 1 1 calc R . .
H10C H -0.0104 0.3974 0.1227 0.070 Uiso 1 1 calc R . .
C11 C 0.4247(4) 0.4621(3) 0.6469(3) 0.0242(6) Uani 1 1 d . . .
F11 F 0.3539(3) 0.42573(17) 0.78983(17) 0.0307(4) Uani 1 1 d . . .
C12 C 0.4410(4) 0.5999(3) 0.5492(3) 0.0225(6) Uani 1 1 d . . .
F12 F 0.3862(3) 0.69612(17) 0.59718(17) 0.0327(4) Uani 1 1 d . . .
C13 C 0.5168(4) 0.6510(3) 0.3922(3) 0.0232(6) Uani 1 1 d . . .
C14 C 0.5294(4) 0.7929(3) 0.2913(3) 0.0257(6) Uani 1 1 d . . .
C15 C 0.6153(5) 0.8446(3) 0.1355(3) 0.0334(7) Uani 1 1 d . . .
N15 N 0.6844(5) 0.8917(3) 0.0113(3) 0.0471(8) Uani 1 1 d . . .
C16 C 0.4653(5) 0.9065(3) 0.3291(3) 0.0317(7) Uani 1 1 d . . .
N16 N 0.4176(5) 1.0020(3) 0.3505(3) 0.0495(8) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.359(3) . ?
O1 C8 1.427(4) . ?
O2 C9 1.380(3) . ?
O2 C10 1.427(4) . ?
C1 C6 1.392(4) . ?
C1 C2 1.422(4) . ?
C1 C7 1.447(3) . ?
C2 C2 1.416(5) 2_566 ?
C2 C3 1.418(3) . ?
C3 C4 1.401(4) . ?
C3 C9 1.437(4) . ?
C4 C5 1.375(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.356(4) 2_566 ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C7 1.356(4) 2_566 ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.328(4) . ?
C11 F11 1.336(3) . ?
C11 C13 1.441(4) 2_666 ?
C12 F12 1.332(3) . ?
C12 C13 1.443(4) . ?
C13 C14 1.369(4) . ?
C13 C11 1.441(4) 2_666 ?
C14 C15 1.436(4) . ?
C14 C16 1.442(4) . ?
C15 N15 1.138(4) . ?
C16 N16 1.144(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
C7 O1 C8 119.1(2) . . ?
C9 O2 C10 114.1(2) . . ?
C6 C1 C2 118.9(2) . . ?
C6 C1 C7 122.1(3) . . ?
C2 C1 C7 119.0(2) . . ?
C2 C2 C3 120.6(3) 2_566 . ?
C2 C2 C1 119.7(3) 2_566 . ?
C3 C2 C1 119.7(2) . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 C9 122.0(2) . . ?
C2 C3 C9 118.6(2) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C9 C7 O1 124.4(2) 2_566 . ?
C9 C7 C1 120.6(2) 2_566 . ?
O1 C7 C1 114.9(2) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 O2 120.9(2) 2_566 . ?
C7 C9 C3 121.5(2) 2_566 . ?
O2 C9 C3 117.6(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 F11 118.4(2) . . ?
C12 C11 C13 123.7(2) . 2_666 ?
F11 C11 C13 117.9(2) . 2_666 ?
C11 C12 F12 118.9(2) . . ?
C11 C12 C13 123.0(2) . . ?
F12 C12 C13 118.1(2) . . ?
C14 C13 C11 123.7(2) . 2_666 ?
C14 C13 C12 123.0(2) . . ?
C11 C13 C12 113.3(2) 2_666 . ?
C13 C14 C15 123.1(2) . . ?
C13 C14 C16 124.1(2) . . ?
C15 C14 C16 112.8(2) . . ?
N15 C15 C14 176.8(3) . . ?
N16 C16 C14 176.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C2 177.8(3) . . . 2_566 ?
C7 C1 C2 C2 -1.3(5) . . . 2_566 ?
C6 C1 C2 C3 -2.4(4) . . . . ?
C7 C1 C2 C3 178.5(3) . . . . ?
C2 C2 C3 C4 -179.7(3) 2_566 . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C2 C3 C9 -0.8(5) 2_566 . . . ?
C1 C2 C3 C9 179.4(3) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C9 C3 C4 C5 -177.4(3) . . . . ?
C3 C4 C5 C6 -1.5(5) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C2 C1 C6 C5 2.4(4) . . . . ?
C7 C1 C6 C5 -178.5(3) . . . . ?
C8 O1 C7 C9 57.0(4) . . . 2_566 ?
C8 O1 C7 C1 -127.1(3) . . . . ?
C6 C1 C7 C9 -176.9(3) . . . 2_566 ?
C2 C1 C7 C9 2.2(4) . . . 2_566 ?
C6 C1 C7 O1 7.0(4) . . . . ?
C2 C1 C7 O1 -173.9(3) . . . . ?
C10 O2 C9 C7 -90.1(4) . . . 2_566 ?
C10 O2 C9 C3 91.5(3) . . . . ?
C4 C3 C9 C7 178.8(3) . . . 2_566 ?
C2 C3 C9 C7 -0.1(4) . . . 2_566 ?
C4 C3 C9 O2 -2.8(4) . . . . ?
C2 C3 C9 O2 178.3(2) . . . . ?
F11 C11 C12 F12 -0.1(4) . . . . ?
C13 C11 C12 F12 -178.7(3) 2_666 . . . ?
F11 C11 C12 C13 179.6(3) . . . . ?
C13 C11 C12 C13 1.0(5) 2_666 . . . ?
C11 C12 C13 C14 178.5(3) . . . . ?
F12 C12 C13 C14 -1.8(4) . . . . ?
C11 C12 C13 C11 -0.9(4) . . . 2_666 ?
F12 C12 C13 C11 178.8(3) . . . 2_666 ?
C11 C13 C14 C15 -4.2(5) 2_666 . . . ?
C12 C13 C14 C15 176.5(3) . . . . ?
C11 C13 C14 C16 178.0(3) 2_666 . . . ?
C12 C13 C14 C16 -1.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.061
