# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_wangd1215
_database_code_depnum_ccdc_archive 'CCDC 918717'
_audit_update_record             
;
2013-01-09 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_DongWang_1357721530.wangd1215.cif'

_audit_creation_date             2012-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled Dec 5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Cl F3 N2 O2'
_chemical_formula_sum            'C20 H16 Cl F3 N2 O2'
_chemical_formula_weight         408.80
_chemical_absolute_configuration ad
_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'
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'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   10.4449(8)
_cell_length_b                   7.9864(6)
_cell_length_c                   11.2224(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.069(7)
_cell_angle_gamma                90.00
_cell_volume                     934.80(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1381
_cell_measurement_temperature    292.88(10)
_cell_measurement_theta_max      28.5674
_cell_measurement_theta_min      3.1259
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
?
;
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3944
_diffrn_reflns_theta_full        28.63
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         3.13
_diffrn_ambient_temperature      292.88(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9756
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -18.00 16.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -19.1930 19.0000 -60.0000 34

#__ type_ start__ end____ width___ exp.time_
2 omega -10.00 94.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 77.0000 90.0000 104

#__ type_ start__ end____ width___ exp.time_
3 omega -45.00 46.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -57.0000 -60.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0150587000
_diffrn_orient_matrix_UB_12      -0.0529196000
_diffrn_orient_matrix_UB_13      0.0481085000
_diffrn_orient_matrix_UB_21      0.0257610000
_diffrn_orient_matrix_UB_22      -0.0694663000
_diffrn_orient_matrix_UB_23      -0.0299236000
_diffrn_orient_matrix_UB_31      0.0610645000
_diffrn_orient_matrix_UB_32      0.0163205000
_diffrn_orient_matrix_UB_33      0.0282652000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2524
_reflns_number_total             3043
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(10)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0395P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1090
_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.
;
_olex2_refinement_description    
;
1. Fixed Uiso
At 1.2 times of:
H20 of C20, H19 of C19, H18 of C18, H17 of C17, H10 of C10, H5 of C5, H4 of
C4, H2A of C2, H16 of C16, H14 of C14, H12 of C12, H11 of C11
At 1.5 times of:
{H9A,H9B,H9C} of C9
2.a Ternary CH refined with riding coordinates:
C10(H10), C11(H11), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
C2(H2A), C4(H4), C5(H5), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
C20(H20)
2.c Idealised Me refined as rotating group:
C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.91912(11) -0.92266(16) -0.28369(10) 0.0736(4) Uani 1 1 d . . .
F1 F -0.11198(19) -0.5269(3) -0.2633(2) 0.0656(7) Uani 1 1 d . . .
F2 F -0.1244(2) -0.4301(4) -0.43951(18) 0.0654(6) Uani 1 1 d . . .
F3 F -0.0623(2) -0.2729(3) -0.2936(3) 0.0788(8) Uani 1 1 d . . .
O1 O -0.5404(2) -0.1718(3) -0.4268(2) 0.0559(7) Uani 1 1 d . . .
O2 O -0.4352(3) -0.4979(5) -0.0076(2) 0.0791(10) Uani 1 1 d . . .
N2 N -0.3716(2) -0.4687(4) -0.3479(3) 0.0398(7) Uani 1 1 d . . .
N1 N -0.6921(2) -0.3790(4) -0.4139(3) 0.0450(7) Uani 1 1 d . . .
C1 C -0.7008(3) -0.5343(4) -0.3565(3) 0.0374(7) Uani 1 1 d . . .
C2 C -0.8040(3) -0.6412(5) -0.3578(3) 0.0460(8) Uani 1 1 d . . .
H2A H -0.8809 -0.6151 -0.3992 0.055 Uiso 1 1 calc R . .
C3 C -0.7883(3) -0.7898(5) -0.2945(3) 0.0473(9) Uani 1 1 d . . .
C4 C -0.6744(3) -0.8317(5) -0.2357(3) 0.0504(9) Uani 1 1 d . . .
H4 H -0.6659 -0.9338 -0.1963 0.060 Uiso 1 1 calc R . .
C5 C -0.5724(4) -0.7218(5) -0.2351(3) 0.0482(9) Uani 1 1 d . . .
H5 H -0.4950 -0.7496 -0.1953 0.058 Uiso 1 1 calc R . .
C6 C -0.5857(3) -0.5706(4) -0.2937(3) 0.0367(7) Uani 1 1 d . . .
C7 C -0.4961(3) -0.4249(5) -0.3036(3) 0.0352(7) Uani 1 1 d . . .
C8 C -0.5750(3) -0.3073(5) -0.3893(3) 0.0411(8) Uani 1 1 d . . .
C9 C -0.7914(3) -0.3085(6) -0.4947(4) 0.0676(13) Uani 1 1 d . . .
H9A H -0.8341 -0.3971 -0.5390 0.101 Uiso 1 1 calc R . .
H9B H -0.7534 -0.2327 -0.5489 0.101 Uiso 1 1 calc R . .
H9C H -0.8525 -0.2493 -0.4495 0.101 Uiso 1 1 calc R . .
C10 C -0.4583(3) -0.3269(5) -0.1844(3) 0.0419(8) Uani 1 1 d . . .
H10 H -0.4980 -0.2157 -0.1880 0.050 Uiso 1 1 calc R . .
C11 C -0.3117(3) -0.3074(4) -0.1817(3) 0.0348(7) Uani 1 1 d . . .
H11 H -0.2743 -0.4006 -0.1350 0.042 Uiso 1 1 calc R . .
C12 C -0.2814(3) -0.3361(4) -0.3131(3) 0.0358(7) Uani 1 1 d . . .
H12 H -0.2998 -0.2349 -0.3603 0.043 Uiso 1 1 calc R . .
C13 C -0.1464(3) -0.3913(5) -0.3261(3) 0.0457(9) Uani 1 1 d . . .
C14 C -0.5030(4) -0.4197(7) -0.0756(3) 0.0627(11) Uani 1 1 d . . .
H14 H -0.5898 -0.4149 -0.0613 0.075 Uiso 1 1 calc R . .
C15 C -0.2601(3) -0.1467(4) -0.1266(3) 0.0386(7) Uani 1 1 d . . .
C16 C -0.2867(3) 0.0062(5) -0.1781(3) 0.0498(9) Uani 1 1 d . . .
H16 H -0.3391 0.0117 -0.2477 0.060 Uiso 1 1 calc R . .
C17 C -0.2368(4) 0.1519(6) -0.1282(5) 0.0685(13) Uani 1 1 d . . .
H17 H -0.2559 0.2545 -0.1641 0.082 Uiso 1 1 calc R . .
C18 C -0.1591(4) 0.1460(7) -0.0257(5) 0.0801(16) Uani 1 1 d . . .
H18 H -0.1249 0.2439 0.0077 0.096 Uiso 1 1 calc R . .
C19 C -0.1327(4) -0.0053(8) 0.0268(4) 0.0800(16) Uani 1 1 d . . .
H19 H -0.0808 -0.0100 0.0967 0.096 Uiso 1 1 calc R . .
C20 C -0.1826(3) -0.1527(6) -0.0231(3) 0.0548(10) Uani 1 1 d . . .
H20 H -0.1637 -0.2550 0.0133 0.066 Uiso 1 1 calc R . .
H2 H -0.381(3) -0.481(4) -0.420(3) 0.035(9) Uiso 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
Cl1 C3 1.739(4) . ?
F1 C13 1.331(4) . ?
F2 C13 1.342(4) . ?
F3 C13 1.329(4) . ?
O1 C8 1.223(4) . ?
O2 C14 1.190(5) . ?
N2 C7 1.459(4) . ?
N2 C12 1.457(4) . ?
N2 H2 0.81(3) . ?
N1 C1 1.403(4) . ?
N1 C8 1.365(4) . ?
N1 C9 1.455(4) . ?
C1 C2 1.374(4) . ?
C1 C6 1.391(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.388(5) . ?
C3 C4 1.371(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(5) . ?
C6 C7 1.501(5) . ?
C7 C8 1.550(5) . ?
C7 C10 1.581(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.537(4) . ?
C10 C14 1.523(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.541(4) . ?
C11 C15 1.512(4) . ?
C12 H12 0.9800 . ?
C12 C13 1.492(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(5) . ?
C15 C20 1.381(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(6) . ?
C20 H20 0.9300 . ?

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 N2 H2 108(2) . . ?
C12 N2 C7 108.0(3) . . ?
C12 N2 H2 113(2) . . ?
C1 N1 C9 124.5(3) . . ?
C8 N1 C1 111.0(3) . . ?
C8 N1 C9 124.4(3) . . ?
C2 C1 N1 127.9(3) . . ?
C2 C1 C6 122.1(3) . . ?
C6 C1 N1 109.9(3) . . ?
C1 C2 H2A 121.5 . . ?
C1 C2 C3 117.0(3) . . ?
C3 C2 H2A 121.5 . . ?
C2 C3 Cl1 119.1(3) . . ?
C4 C3 Cl1 118.8(3) . . ?
C4 C3 C2 122.0(3) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 109.1(3) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 131.8(3) . . ?
N2 C7 C6 114.2(3) . . ?
N2 C7 C8 112.8(3) . . ?
N2 C7 C10 102.7(2) . . ?
C6 C7 C8 101.7(2) . . ?
C6 C7 C10 116.7(2) . . ?
C8 C7 C10 109.0(3) . . ?
O1 C8 N1 125.4(3) . . ?
O1 C8 C7 126.4(3) . . ?
N1 C8 C7 108.2(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10 109.1 . . ?
C11 C10 C7 105.7(2) . . ?
C11 C10 H10 109.1 . . ?
C14 C10 C7 111.3(3) . . ?
C14 C10 H10 109.1 . . ?
C14 C10 C11 112.4(3) . . ?
C10 C11 H11 107.6 . . ?
C10 C11 C12 102.8(2) . . ?
C12 C11 H11 107.6 . . ?
C15 C11 C10 115.3(3) . . ?
C15 C11 H11 107.6 . . ?
C15 C11 C12 115.5(3) . . ?
N2 C12 C11 101.6(3) . . ?
N2 C12 H12 110.5 . . ?
N2 C12 C13 111.1(3) . . ?
C11 C12 H12 110.5 . . ?
C13 C12 C11 112.4(3) . . ?
C13 C12 H12 110.5 . . ?
F1 C13 F2 105.0(3) . . ?
F1 C13 C12 114.7(3) . . ?
F2 C13 C12 111.9(3) . . ?
F3 C13 F1 106.1(3) . . ?
F3 C13 F2 106.3(3) . . ?
F3 C13 C12 112.2(3) . . ?
O2 C14 C10 124.9(4) . . ?
O2 C14 H14 117.5 . . ?
C10 C14 H14 117.5 . . ?
C16 C15 C11 121.5(3) . . ?
C16 C15 C20 118.8(4) . . ?
C20 C15 C11 119.7(3) . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(4) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(5) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.3(4) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 119.9(4) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?

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
Cl1 C3 C4 C5 -174.8(3) . . . . ?
N2 C7 C8 O1 -55.6(5) . . . . ?
N2 C7 C8 N1 126.0(3) . . . . ?
N2 C7 C10 C11 6.7(4) . . . . ?
N2 C7 C10 C14 -115.7(3) . . . . ?
N2 C12 C13 F1 -58.1(4) . . . . ?
N2 C12 C13 F2 61.3(4) . . . . ?
N2 C12 C13 F3 -179.3(3) . . . . ?
N1 C1 C2 C3 179.3(3) . . . . ?
N1 C1 C6 C5 -177.2(3) . . . . ?
N1 C1 C6 C7 3.6(4) . . . . ?
C1 N1 C8 O1 -179.8(3) . . . . ?
C1 N1 C8 C7 -1.3(4) . . . . ?
C1 C2 C3 Cl1 175.2(3) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C1 C6 C7 N2 -125.9(3) . . . . ?
C1 C6 C7 C8 -4.1(3) . . . . ?
C1 C6 C7 C10 114.4(3) . . . . ?
C2 C1 C6 C5 2.9(5) . . . . ?
C2 C1 C6 C7 -176.3(3) . . . . ?
C2 C3 C4 C5 2.2(6) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 -2.4(5) . . . . ?
C4 C5 C6 C7 176.6(3) . . . . ?
C5 C6 C7 N2 55.1(5) . . . . ?
C5 C6 C7 C8 176.8(4) . . . . ?
C5 C6 C7 C10 -64.7(5) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
C6 C7 C8 O1 -178.3(3) . . . . ?
C6 C7 C8 N1 3.3(3) . . . . ?
C6 C7 C10 C11 132.4(3) . . . . ?
C6 C7 C10 C14 10.1(4) . . . . ?
C7 N2 C12 C11 45.2(3) . . . . ?
C7 N2 C12 C13 165.0(3) . . . . ?
C7 C10 C11 C12 19.0(4) . . . . ?
C7 C10 C11 C15 145.6(3) . . . . ?
C7 C10 C14 O2 104.2(5) . . . . ?
C8 N1 C1 C2 178.5(3) . . . . ?
C8 N1 C1 C6 -1.4(4) . . . . ?
C8 C7 C10 C11 -113.2(3) . . . . ?
C8 C7 C10 C14 124.5(3) . . . . ?
C9 N1 C1 C2 -5.1(5) . . . . ?
C9 N1 C1 C6 175.0(3) . . . . ?
C9 N1 C8 O1 3.8(6) . . . . ?
C9 N1 C8 C7 -177.8(3) . . . . ?
C10 C7 C8 O1 57.9(4) . . . . ?
C10 C7 C8 N1 -120.6(3) . . . . ?
C10 C11 C12 N2 -38.0(3) . . . . ?
C10 C11 C12 C13 -156.9(3) . . . . ?
C10 C11 C15 C16 -65.4(4) . . . . ?
C10 C11 C15 C20 115.6(3) . . . . ?
C11 C10 C14 O2 -14.1(6) . . . . ?
C11 C12 C13 F1 55.0(4) . . . . ?
C11 C12 C13 F2 174.5(3) . . . . ?
C11 C12 C13 F3 -66.2(4) . . . . ?
C11 C15 C16 C17 -178.7(3) . . . . ?
C11 C15 C20 C19 178.8(3) . . . . ?
C12 N2 C7 C6 -159.7(3) . . . . ?
C12 N2 C7 C8 84.8(3) . . . . ?
C12 N2 C7 C10 -32.4(3) . . . . ?
C12 C11 C15 C16 54.4(4) . . . . ?
C12 C11 C15 C20 -124.6(3) . . . . ?
C14 C10 C11 C12 140.7(3) . . . . ?
C14 C10 C11 C15 -92.7(4) . . . . ?
C15 C11 C12 N2 -164.4(3) . . . . ?
C15 C11 C12 C13 76.7(4) . . . . ?
C15 C16 C17 C18 0.1(6) . . . . ?
C16 C15 C20 C19 -0.2(5) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C17 C18 C19 C20 0.6(7) . . . . ?
C18 C19 C20 C15 -0.2(7) . . . . ?
C20 C15 C16 C17 0.3(5) . . . . ?



####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/cc144g0r
_database_code_depnum_ccdc_archive 'CCDC 1046963'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Br F3 N2 O'
_chemical_formula_weight         321.10

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   6.8291(12)
_cell_length_b                   12.139(2)
_cell_length_c                   14.882(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.467(3)
_cell_angle_gamma                90.00
_cell_volume                     1209.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yelllow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    3.427
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4263
_exptl_absorpt_correction_T_max  0.4471
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5971
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2127
_reflns_number_gt                1710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0430P)²+0.3819P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0075(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2127
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
Br1 Br 0.38502(5) -0.20095(2) 0.01715(2) 0.05924(17) Uani 1 1 d . . .
O1 O -0.1259(3) 0.26955(18) 0.22984(15) 0.0633(6) Uani 1 1 d . . .
N1 N -0.1372(3) 0.0815(2) 0.20754(16) 0.0476(6) Uani 1 1 d . . .
N2 N 0.1979(4) 0.25023(19) 0.11387(17) 0.0476(6) Uani 1 1 d . . .
C1 C 0.2139(4) -0.1171(2) 0.07743(19) 0.0443(6) Uani 1 1 d . . .
C2 C 0.2389(4) -0.0029(2) 0.08255(18) 0.0425(7) Uani 1 1 d . . .
H2 H 0.3355 0.0320 0.0566 0.051 Uiso 1 1 calc R . .
C3 C 0.1153(4) 0.0563(2) 0.12752(18) 0.0395(6) Uani 1 1 d . . .
C4 C -0.0330(4) 0.0029(2) 0.16562(18) 0.0424(6) Uani 1 1 d . . .
C5 C -0.0598(5) -0.1097(2) 0.1586(2) 0.0512(7) Uani 1 1 d . . .
H5 H -0.1588 -0.1449 0.1827 0.061 Uiso 1 1 calc R . .
C6 C 0.0681(5) -0.1685(2) 0.1139(2) 0.0521(8) Uani 1 1 d . . .
H6 H 0.0544 -0.2446 0.1085 0.063 Uiso 1 1 calc R . .
C7 C 0.0981(4) 0.1744(2) 0.14369(19) 0.0416(6) Uani 1 1 d . . .
C8 C -0.0672(4) 0.1854(2) 0.1989(2) 0.0466(7) Uani 1 1 d . . .
C9 C -0.3034(5) 0.0587(3) 0.2533(2) 0.0676(10) Uani 1 1 d . . .
H9A H -0.2597 0.0678 0.3183 0.101 Uiso 1 1 calc R . .
H9B H -0.3487 -0.0155 0.2404 0.101 Uiso 1 1 calc R . .
H9C H -0.4109 0.1089 0.2314 0.101 Uiso 1 1 calc R . .
C10 C 0.1565(5) 0.3650(2) 0.1324(2) 0.0548(8) Uani 1 1 d . . .
H10A H 0.1933 0.3794 0.1977 0.066 Uiso 1 1 calc R . .
H10B H 0.0149 0.3799 0.1127 0.066 Uiso 1 1 calc R . .
C11 C 0.2728(6) 0.4373(3) 0.0823(3) 0.0655(9) Uani 1 1 d . . .
F1 F 0.4684(3) 0.41770(17) 0.10307(17) 0.0869(7) Uani 1 1 d . . .
F2 F 0.2184(4) 0.4278(2) -0.00819(15) 0.0987(8) Uani 1 1 d . . .
F3 F 0.2479(4) 0.54358(16) 0.10300(19) 0.1028(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
Br1 C1 1.904(3) . ?
O1 C8 1.220(3) . ?
N1 C8 1.364(4) . ?
N1 C4 1.408(3) . ?
N1 C9 1.461(3) . ?
N2 C7 1.276(4) . ?
N2 C10 1.459(4) . ?
C1 C6 1.374(4) . ?
C1 C2 1.397(4) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.412(4) . ?
C3 C7 1.463(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.395(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.529(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.480(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 F2 1.329(4) . ?
C11 F1 1.332(4) . ?
C11 F3 1.345(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
C8 N1 C4 111.5(2) . . ?
C8 N1 C9 122.5(3) . . ?
C4 N1 C9 125.9(3) . . ?
C7 N2 C10 119.1(2) . . ?
C6 C1 C2 121.3(3) . . ?
C6 C1 Br1 120.2(2) . . ?
C2 C1 Br1 118.5(2) . . ?
C3 C2 C1 117.6(2) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 C7 131.9(2) . . ?
C4 C3 C7 107.2(2) . . ?
C5 C4 N1 129.3(3) . . ?
C5 C4 C3 121.3(3) . . ?
N1 C4 C3 109.5(2) . . ?
C4 C5 C6 117.1(3) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C1 C6 C5 121.8(3) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
N2 C7 C3 125.7(3) . . ?
N2 C7 C8 128.8(3) . . ?
C3 C7 C8 105.4(2) . . ?
O1 C8 N1 126.3(3) . . ?
O1 C8 C7 127.5(3) . . ?
N1 C8 C7 106.3(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 109.1(3) . . ?
N2 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
N2 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
F2 C11 F1 106.5(3) . . ?
F2 C11 F3 107.0(3) . . ?
F1 C11 F3 106.6(3) . . ?
F2 C11 C10 112.9(3) . . ?
F1 C11 C10 113.0(3) . . ?
F3 C11 C10 110.4(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 C3 1.6(4) . . . . ?
Br1 C1 C2 C3 -179.2(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C2 C3 C7 -178.6(3) . . . . ?
C8 N1 C4 C5 -179.3(3) . . . . ?
C9 N1 C4 C5 -0.7(5) . . . . ?
C8 N1 C4 C3 0.4(3) . . . . ?
C9 N1 C4 C3 179.1(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C7 C3 C4 C5 177.7(3) . . . . ?
C2 C3 C4 N1 179.8(2) . . . . ?
C7 C3 C4 N1 -2.0(3) . . . . ?
N1 C4 C5 C6 -179.2(3) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
Br1 C1 C6 C5 179.9(2) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C10 N2 C7 C3 177.1(3) . . . . ?
C10 N2 C7 C8 0.0(5) . . . . ?
C2 C3 C7 N2 2.8(5) . . . . ?
C4 C3 C7 N2 -175.0(3) . . . . ?
C2 C3 C7 C8 -179.5(3) . . . . ?
C4 C3 C7 C8 2.7(3) . . . . ?
C4 N1 C8 O1 -178.5(3) . . . . ?
C9 N1 C8 O1 2.8(5) . . . . ?
C4 N1 C8 C7 1.3(3) . . . . ?
C9 N1 C8 C7 -177.4(3) . . . . ?
N2 C7 C8 O1 -5.1(5) . . . . ?
C3 C7 C8 O1 177.3(3) . . . . ?
N2 C7 C8 N1 175.2(3) . . . . ?
C3 C7 C8 N1 -2.4(3) . . . . ?
C7 N2 C10 C11 -173.5(3) . . . . ?
N2 C10 C11 F2 64.4(4) . . . . ?
N2 C10 C11 F1 -56.6(4) . . . . ?
N2 C10 C11 F3 -175.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.055
