# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl
#TrackingRef 'int-173.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 Cl F2 N O2'
_chemical_formula_sum            'C25 H20 Cl F2 N O2'
_chemical_formula_weight         439.87

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'
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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   8.5989(6)
_cell_length_b                   16.1254(13)
_cell_length_c                   15.4619(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.125(6)
_cell_angle_gamma                90.00
_cell_volume                     2135.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    3575
_cell_measurement_theta_min      3.0865
_cell_measurement_theta_max      29.0873

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   CrysAlisPro
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       multi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13278
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         29.15
_reflns_number_total             5761
_reflns_number_gt                3824
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0415P)²+0.7874P] 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         5761
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Cl1 Cl 0.29939(6) -0.06822(4) 0.35579(4) 0.05806(17) Uani 1 1 d . . .
F1 F 0.39133(17) 0.40159(9) 0.39664(10) 0.0787(4) Uani 1 1 d . . .
O2 O 0.76745(18) -0.18854(9) 0.00329(9) 0.0570(4) Uani 1 1 d . . .
F2 F 0.83349(18) -0.09632(11) 0.51092(9) 0.0841(5) Uani 1 1 d . . .
O1 O 0.01770(19) 0.16372(13) 0.31198(11) 0.0798(6) Uani 1 1 d . . .
N2 N 0.45376(16) 0.06115(8) 0.25401(9) 0.0332(3) Uani 1 1 d . . .
C6' C 0.7072(2) 0.04350(12) 0.33738(12) 0.0415(4) Uani 1 1 d . . .
H6' H 0.7484 0.0848 0.3042 0.050 Uiso 1 1 calc R . .
C2' C 0.4922(2) -0.03773(11) 0.37406(11) 0.0382(4) Uani 1 1 d . . .
C1 C 0.33521(19) 0.12070(11) 0.27883(11) 0.0348(4) Uani 1 1 d . . .
H1 H 0.3053 0.1063 0.3366 0.042 Uiso 1 1 calc R . .
C10 C 0.4960(2) 0.22822(11) 0.21550(12) 0.0378(4) Uani 1 1 d . . .
C2" C 0.5292(2) -0.06771(11) 0.14281(11) 0.0395(4) Uani 1 1 d . . .
H2" H 0.4511 -0.0753 0.1800 0.047 Uiso 1 1 calc R . .
C9 C 0.40115(19) 0.20760(11) 0.28128(11) 0.0358(4) Uani 1 1 d . . .
C3 C 0.52729(19) 0.08280(11) 0.17852(11) 0.0338(4) Uani 1 1 d . . .
C1' C 0.55044(19) 0.02335(10) 0.32224(10) 0.0324(4) Uani 1 1 d . . .
C5" C 0.7552(2) -0.04628(12) 0.03037(12) 0.0464(5) Uani 1 1 d . . .
H5" H 0.8300 -0.0387 -0.0088 0.056 Uiso 1 1 calc R . .
C4" C 0.7009(2) -0.12523(12) 0.04570(11) 0.0409(4) Uani 1 1 d . . .
C5 C 0.5530(2) 0.30912(12) 0.21251(14) 0.0493(5) Uani 1 1 d . . .
H5 H 0.6144 0.3241 0.1685 0.059 Uiso 1 1 calc R . .
C1" C 0.5854(2) 0.01174(11) 0.13063(10) 0.0346(4) Uani 1 1 d . . .
C4 C 0.5378(2) 0.16312(11) 0.15667(11) 0.0387(4) Uani 1 1 d . . .
H4 H 0.5721 0.1773 0.1033 0.046 Uiso 1 1 calc R . .
C3' C 0.5867(3) -0.07739(13) 0.43850(12) 0.0494(5) Uani 1 1 d . . .
H3' H 0.5465 -0.1175 0.4735 0.059 Uiso 1 1 calc R . .
C3" C 0.5857(2) -0.13589(12) 0.10144(12) 0.0424(4) Uani 1 1 d . . .
H3" H 0.5464 -0.1885 0.1110 0.051 Uiso 1 1 calc R . .
C8 C 0.3675(2) 0.26593(12) 0.34299(13) 0.0444(4) Uani 1 1 d . . .
H8 H 0.3057 0.2521 0.3872 0.053 Uiso 1 1 calc R . .
C6" C 0.6996(2) 0.02068(12) 0.07252(11) 0.0420(4) Uani 1 1 d . . .
H6" H 0.7387 0.0732 0.0622 0.050 Uiso 1 1 calc R . .
C6 C 0.5197(2) 0.36733(12) 0.27379(16) 0.0559(6) Uani 1 1 d . . .
H6 H 0.5592 0.4209 0.2720 0.067 Uiso 1 1 calc R . .
C5' C 0.8039(2) 0.00390(14) 0.40048(13) 0.0518(5) Uani 1 1 d . . .
H5' H 0.9092 0.0175 0.4096 0.062 Uiso 1 1 calc R . .
C2A C 0.0573(2) 0.16551(12) 0.23970(14) 0.0453(5) Uani 1 1 d . . .
C1A C 0.1913(2) 0.11433(12) 0.21315(12) 0.0427(4) Uani 1 1 d . . .
H1A1 H 0.2185 0.1329 0.1568 0.051 Uiso 1 1 calc R . .
H1A2 H 0.1590 0.0568 0.2077 0.051 Uiso 1 1 calc R . .
C7 C 0.4274(2) 0.34414(13) 0.33723(15) 0.0529(5) Uani 1 1 d . . .
C4' C 0.7407(3) -0.05582(14) 0.44910(13) 0.0536(5) Uani 1 1 d . . .
C3A C -0.0241(4) 0.2191(2) 0.1732(2) 0.1000(11) Uani 1 1 d . . .
H3A1 H -0.1064 0.2485 0.1980 0.150 Uiso 1 1 calc R . .
H3A2 H -0.0674 0.1856 0.1256 0.150 Uiso 1 1 calc R . .
H3A3 H 0.0485 0.2581 0.1526 0.150 Uiso 1 1 calc R . .
C11 C 0.7278(3) -0.27044(14) 0.02603(18) 0.0755(8) Uani 1 1 d . . .
H11A H 0.7814 -0.3092 -0.0079 0.113 Uiso 1 1 calc R . .
H11B H 0.6171 -0.2782 0.0148 0.113 Uiso 1 1 calc R . .
H11C H 0.7579 -0.2795 0.0866 0.113 Uiso 1 1 calc R . .


_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 C2' 1.7282(19) . ?
F1 C7 1.360(2) . ?
O2 C4" 1.366(2) . ?
O2 C11 1.416(3) . ?
F2 C4' 1.357(2) . ?
O1 C2A 1.197(2) . ?
N2 C3 1.420(2) . ?
N2 C1' 1.421(2) . ?
N2 C1 1.476(2) . ?
C6' C5' 1.380(3) . ?
C6' C1' 1.386(2) . ?
C2' C3' 1.385(3) . ?
C2' C1' 1.391(2) . ?
C1 C9 1.511(2) . ?
C1 C1A 1.533(2) . ?
C10 C5 1.396(3) . ?
C10 C9 1.400(2) . ?
C10 C4 1.455(2) . ?
C2" C3" 1.382(2) . ?
C2" C1" 1.388(2) . ?
C9 C8 1.388(2) . ?
C3 C4 1.344(2) . ?
C3 C1" 1.476(2) . ?
C5" C6" 1.369(3) . ?
C5" C4" 1.384(3) . ?
C4" C3" 1.381(3) . ?
C5 C6 1.382(3) . ?
C1" C6" 1.396(2) . ?
C3' C4' 1.364(3) . ?
C8 C7 1.368(3) . ?
C6 C7 1.368(3) . ?
C5' C4' 1.365(3) . ?
C2A C3A 1.471(3) . ?
C2A C1A 1.503(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
C4" O2 C11 117.21(16) . . ?
C3 N2 C1' 116.22(13) . . ?
C3 N2 C1 114.99(13) . . ?
C1' N2 C1 117.25(13) . . ?
C5' C6' C1' 121.76(18) . . ?
C3' C2' C1' 121.55(17) . . ?
C3' C2' Cl1 118.62(15) . . ?
C1' C2' Cl1 119.79(14) . . ?
N2 C1 C9 110.10(13) . . ?
N2 C1 C1A 108.65(14) . . ?
C9 C1 C1A 110.97(15) . . ?
C5 C10 C9 118.37(17) . . ?
C5 C10 C4 123.16(17) . . ?
C9 C10 C4 118.38(16) . . ?
C3" C2" C1" 122.04(16) . . ?
C8 C9 C10 120.61(17) . . ?
C8 C9 C1 123.01(16) . . ?
C10 C9 C1 116.35(15) . . ?
C4 C3 N2 119.24(15) . . ?
C4 C3 C1" 126.09(15) . . ?
N2 C3 C1" 114.67(14) . . ?
C6' C1' C2' 117.61(16) . . ?
C6' C1' N2 121.37(15) . . ?
C2' C1' N2 120.97(15) . . ?
C6" C5" C4" 120.42(17) . . ?
O2 C4" C3" 124.13(18) . . ?
O2 C4" C5" 116.31(16) . . ?
C3" C4" C5" 119.57(17) . . ?
C6 C5 C10 121.17(19) . . ?
C2" C1" C6" 117.13(16) . . ?
C2" C1" C3 120.72(15) . . ?
C6" C1" C3 122.14(16) . . ?
C3 C4 C10 120.84(16) . . ?
C4' C3' C2' 118.00(18) . . ?
C4" C3" C2" 119.43(17) . . ?
C7 C8 C9 118.50(19) . . ?
C5" C6" C1" 121.36(18) . . ?
C7 C6 C5 118.35(19) . . ?
C4' C5' C6' 118.11(19) . . ?
O1 C2A C3A 120.6(2) . . ?
O1 C2A C1A 122.04(19) . . ?
C3A C2A C1A 117.37(19) . . ?
C2A C1A C1 112.04(15) . . ?
F1 C7 C8 118.3(2) . . ?
F1 C7 C6 118.7(2) . . ?
C8 C7 C6 122.99(19) . . ?
F2 C4' C5' 119.3(2) . . ?
F2 C4' C3' 117.7(2) . . ?
C5' C4' C3' 122.96(19) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.00
_refine_diff_density_min         -0.269
_refine_diff_density_rms         1.00


_database_code_depnum_ccdc_archive 'CCDC 868792'
