# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_xabs2
#TrackingRef 'ml031_01_xabs2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 Br F3 N3 O2'
_chemical_formula_sum            'C16 H17 Br F3 N3 O2'
_chemical_formula_weight         420.24

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   P21/c
_symmetry_space_group_name_Hall  -P2ybc

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.8394(10)
_cell_length_b                   14.6957(9)
_cell_length_c                   15.2413(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.1560(10)
_cell_angle_gamma                90.00
_cell_volume                     3672.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7773
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.44

_exptl_crystal_description       column
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    2.281
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_correction_T_min  0.6037
_exptl_absorpt_correction_T_max  0.7260
_exptl_absorpt_process_details   'XABS2 as implemented in WinGX'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      180(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  'APEX2 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8021
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.24
_diffrn_reflns_theta_max         27.00
_reflns_number_total             8021
_reflns_number_gt                5434
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0567P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.00125(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8021
_refine_ls_number_parameters     464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.002
_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 1.08679(2) -0.00731(2) 0.65094(3) 0.05350(12) Uani 1 1 d . . .
F1 F 0.53352(11) 0.42039(13) 0.44188(14) 0.0586(5) Uani 1 1 d . . .
F2 F 0.47015(11) 0.36162(14) 0.53554(12) 0.0560(5) Uani 1 1 d . . .
F3 F 0.43878(10) 0.32279(15) 0.39701(12) 0.0553(5) Uani 1 1 d . . .
O1 O 0.85127(11) 0.11111(13) 0.57254(14) 0.0382(5) Uani 1 1 d . . .
O2 O 1.11103(11) 0.26351(13) 0.63138(14) 0.0392(5) Uani 1 1 d . . .
N1 N 0.38889(18) 0.1326(2) 0.4874(3) 0.0762(10) Uani 1 1 d . . .
N2 N 0.78699(13) 0.24591(16) 0.53162(16) 0.0362(6) Uani 1 1 d . . .
H2N H 0.7959 0.3028 0.5188 0.037(8) Uiso 1 1 calc R . .
N3 N 0.99843(12) 0.17382(15) 0.60009(15) 0.0293(5) Uani 1 1 d . . .
H3N H 0.9817 0.1169 0.5958 0.028(7) Uiso 1 1 calc R . .
C1 C 0.70488(15) 0.2191(2) 0.51895(18) 0.0323(6) Uani 1 1 d . . .
C2 C 0.64630(16) 0.2879(2) 0.49458(18) 0.0350(6) Uani 1 1 d . . .
H2 H 0.6630 0.3480 0.4846 0.042 Uiso 1 1 calc R . .
C3 C 0.56336(16) 0.2683(2) 0.48494(17) 0.0344(6) Uani 1 1 d . . .
C4 C 0.53949(17) 0.1792(2) 0.4985(2) 0.0397(7) Uani 1 1 d . . .
C5 C 0.59733(17) 0.1119(2) 0.5191(2) 0.0440(7) Uani 1 1 d . . .
H5 H 0.5806 0.0511 0.5259 0.053 Uiso 1 1 calc R . .
C6 C 0.68004(17) 0.1309(2) 0.5301(2) 0.0380(7) Uani 1 1 d . . .
H6 H 0.7192 0.0836 0.5452 0.046 Uiso 1 1 calc R . .
C7 C 0.50237(18) 0.3429(2) 0.4643(2) 0.0419(7) Uani 1 1 d . . .
C8 C 0.4544(2) 0.1541(2) 0.4918(2) 0.0524(9) Uani 1 1 d . . .
C9 C 0.85420(16) 0.19265(19) 0.56177(19) 0.0320(6) Uani 1 1 d . . .
C10 C 0.93567(16) 0.24530(18) 0.5866(2) 0.0346(7) Uani 1 1 d . . .
C11 C 0.94629(18) 0.3090(2) 0.5114(3) 0.0590(10) Uani 1 1 d . . .
H11A H 0.9068 0.3588 0.5056 0.088 Uiso 1 1 calc R . .
H11B H 0.9372 0.2752 0.4545 0.088 Uiso 1 1 calc R . .
H11C H 1.0017 0.3339 0.5255 0.088 Uiso 1 1 calc R . .
C12 C 0.93872(19) 0.2954(2) 0.6761(2) 0.0542(9) Uani 1 1 d . . .
H12A H 0.9215 0.2540 0.7187 0.081 Uiso 1 1 calc R . .
H12B H 0.9020 0.3480 0.6651 0.081 Uiso 1 1 calc R . .
H12C H 0.9945 0.3162 0.7015 0.081 Uiso 1 1 calc R . .
C13 C 1.07878(15) 0.18851(18) 0.61826(17) 0.0268(5) Uani 1 1 d . . .
C14 C 1.13426(16) 0.10615(18) 0.61316(19) 0.0329(6) Uani 1 1 d . . .
C15 C 1.21749(18) 0.1199(2) 0.6765(2) 0.0550(9) Uani 1 1 d . . .
H15A H 1.2519 0.0668 0.6734 0.083 Uiso 1 1 calc R . .
H15B H 1.2108 0.1272 0.7383 0.083 Uiso 1 1 calc R . .
H15C H 1.2433 0.1744 0.6585 0.083 Uiso 1 1 calc R . .
C16 C 1.1398(2) 0.0932(2) 0.5161(2) 0.0503(8) Uani 1 1 d . . .
H16A H 1.1612 0.1488 0.4944 0.075 Uiso 1 1 calc R . .
H16B H 1.0854 0.0803 0.4788 0.075 Uiso 1 1 calc R . .
H16C H 1.1763 0.0421 0.5122 0.075 Uiso 1 1 calc R . .
Br2 Br 0.118753(19) 1.09619(3) -0.09657(2) 0.06644(15) Uani 1 1 d . . .
F4 F 0.29981(11) 0.59142(13) 0.2244(2) 0.0938(9) Uani 1 1 d . . .
F5 F 0.40886(14) 0.55704(13) 0.31985(14) 0.0670(6) Uani 1 1 d . . .
F6 F 0.40844(13) 0.55826(12) 0.18119(13) 0.0603(5) Uani 1 1 d . . .
O3 O 0.19108(11) 0.84610(13) 0.23385(15) 0.0414(5) Uani 1 1 d . . .
O4 O 0.21790(11) 0.93416(13) 0.04861(13) 0.0381(5) Uani 1 1 d . . .
N4 N 0.60124(14) 0.60818(18) 0.27334(19) 0.0457(6) Uani 1 1 d . . .
N5 N 0.30706(12) 0.92840(14) 0.23931(15) 0.0295(5) Uani 1 1 d . . .
H5N H 0.3258 0.9845 0.2421 0.037(8) Uiso 1 1 calc R . .
N6 N 0.19957(11) 1.05757(15) 0.13060(14) 0.0248(5) Uani 1 1 d . . .
H6N H 0.2053 1.1169 0.1362 0.050(10) Uiso 1 1 calc R . .
C17 C 0.36466(14) 0.85859(17) 0.24976(17) 0.0254(5) Uani 1 1 d . . .
C18 C 0.34380(15) 0.76647(17) 0.24293(17) 0.0274(6) Uani 1 1 d . . .
H18 H 0.2882 0.7488 0.2332 0.033 Uiso 1 1 calc R . .
C19 C 0.40375(15) 0.70119(17) 0.25028(17) 0.0268(6) Uani 1 1 d . . .
C20 C 0.48639(14) 0.72617(18) 0.26549(17) 0.0260(5) Uani 1 1 d . . .
C21 C 0.50679(15) 0.81784(19) 0.27536(18) 0.0310(6) Uani 1 1 d . . .
H21 H 0.5625 0.8355 0.2878 0.037 Uiso 1 1 calc R . .
C22 C 0.44736(15) 0.88321(18) 0.26732(19) 0.0313(6) Uani 1 1 d . . .
H22 H 0.4623 0.9456 0.2737 0.038 Uiso 1 1 calc R . .
C23 C 0.37875(17) 0.6023(2) 0.2435(2) 0.0397(7) Uani 1 1 d . . .
C24 C 0.55031(15) 0.65940(19) 0.27035(18) 0.0314(6) Uani 1 1 d . . .
C25 C 0.22335(15) 0.91826(18) 0.22501(18) 0.0293(6) Uani 1 1 d . . .
C26 C 0.17429(14) 1.00639(17) 0.20321(17) 0.0261(5) Uani 1 1 d . . .
C27 C 0.19147(17) 1.06739(18) 0.28721(18) 0.0340(6) Uani 1 1 d . . .
H27A H 0.2495 1.0831 0.3033 0.051 Uiso 1 1 calc R . .
H27B H 0.1769 1.0349 0.3374 0.051 Uiso 1 1 calc R . .
H27C H 0.1590 1.1232 0.2745 0.051 Uiso 1 1 calc R . .
C28 C 0.08348(15) 0.9844(2) 0.1748(2) 0.0361(7) Uani 1 1 d . . .
H28A H 0.0523 1.0410 0.1617 0.054 Uiso 1 1 calc R . .
H28B H 0.0665 0.9519 0.2237 0.054 Uiso 1 1 calc R . .
H28C H 0.0733 0.9461 0.1207 0.054 Uiso 1 1 calc R . .
C29 C 0.21421(14) 1.01756(19) 0.05639(17) 0.0286(6) Uani 1 1 d . . .
C30 C 0.22899(14) 1.0809(2) -0.01784(18) 0.0317(6) Uani 1 1 d . . .
C31 C 0.28172(18) 1.0338(2) -0.0734(2) 0.0461(8) Uani 1 1 d . . .
H31A H 0.2875 1.0734 -0.1232 0.069 Uiso 1 1 calc R . .
H31B H 0.2558 0.9765 -0.0976 0.069 Uiso 1 1 calc R . .
H31C H 0.3357 1.0210 -0.0350 0.069 Uiso 1 1 calc R . .
C32 C 0.26177(18) 1.1754(2) 0.01218(19) 0.0402(7) Uani 1 1 d . . .
H32A H 0.3153 1.1697 0.0538 0.060 Uiso 1 1 calc R . .
H32B H 0.2240 1.2062 0.0427 0.060 Uiso 1 1 calc R . .
H32C H 0.2671 1.2109 -0.0406 0.060 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
Br1 C14 1.990(3) . ?
F1 C7 1.330(4) . ?
F2 C7 1.348(3) . ?
F3 C7 1.336(3) . ?
O1 C9 1.212(3) . ?
O2 C13 1.225(3) . ?
N1 C8 1.135(4) . ?
N2 C9 1.367(3) . ?
N2 C1 1.408(3) . ?
N2 H2N 0.8800 . ?
N3 C13 1.336(3) . ?
N3 C10 1.471(3) . ?
N3 H3N 0.8800 . ?
C1 C6 1.383(4) . ?
C1 C2 1.402(4) . ?
C2 C3 1.400(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(4) . ?
C3 C7 1.486(4) . ?
C4 C5 1.373(4) . ?
C4 C8 1.460(4) . ?
C5 C6 1.393(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C9 C10 1.545(4) . ?
C10 C11 1.522(4) . ?
C10 C12 1.541(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.542(4) . ?
C14 C16 1.516(4) . ?
C14 C15 1.523(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Br2 C30 1.981(3) . ?
F4 C23 1.304(3) . ?
F5 C23 1.336(4) . ?
F6 C23 1.336(4) . ?
O3 C25 1.213(3) . ?
O4 C29 1.234(3) . ?
N4 C24 1.134(3) . ?
N5 C25 1.385(3) . ?
N5 C17 1.396(3) . ?
N5 H5N 0.8800 . ?
N6 C29 1.346(3) . ?
N6 C26 1.478(3) . ?
N6 H6N 0.8800 . ?
C17 C18 1.397(3) . ?
C17 C22 1.404(3) . ?
C18 C19 1.379(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.406(3) . ?
C19 C23 1.510(4) . ?
C20 C21 1.390(4) . ?
C20 C24 1.446(4) . ?
C21 C22 1.372(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C25 C26 1.531(3) . ?
C26 C28 1.526(3) . ?
C26 C27 1.535(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.529(4) . ?
C30 C32 1.525(4) . ?
C30 C31 1.526(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
C9 N2 C1 126.7(2) . . ?
C9 N2 H2N 116.6 . . ?
C1 N2 H2N 116.6 . . ?
C13 N3 C10 125.1(2) . . ?
C13 N3 H3N 117.4 . . ?
C10 N3 H3N 117.4 . . ?
C6 C1 C2 119.6(2) . . ?
C6 C1 N2 124.1(2) . . ?
C2 C1 N2 116.4(3) . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 C7 120.9(2) . . ?
C2 C3 C7 119.7(3) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 C8 117.9(3) . . ?
C3 C4 C8 122.4(3) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
F1 C7 F3 106.6(3) . . ?
F1 C7 F2 106.7(3) . . ?
F3 C7 F2 105.3(2) . . ?
F1 C7 C3 113.1(2) . . ?
F3 C7 C3 113.2(3) . . ?
F2 C7 C3 111.4(2) . . ?
N1 C8 C4 178.3(4) . . ?
O1 C9 N2 123.7(3) . . ?
O1 C9 C10 121.5(2) . . ?
N2 C9 C10 114.6(2) . . ?
N3 C10 C11 109.9(2) . . ?
N3 C10 C12 109.9(2) . . ?
C11 C10 C12 112.8(3) . . ?
N3 C10 C9 104.3(2) . . ?
C11 C10 C9 111.9(2) . . ?
C12 C10 C9 107.8(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 N3 124.7(2) . . ?
O2 C13 C14 117.6(2) . . ?
N3 C13 C14 117.4(2) . . ?
C16 C14 C15 112.5(3) . . ?
C16 C14 C13 108.7(2) . . ?
C15 C14 C13 110.2(2) . . ?
C16 C14 Br1 107.2(2) . . ?
C15 C14 Br1 107.44(19) . . ?
C13 C14 Br1 110.81(17) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 N5 C17 126.5(2) . . ?
C25 N5 H5N 116.7 . . ?
C17 N5 H5N 116.7 . . ?
C29 N6 C26 123.1(2) . . ?
C29 N6 H6N 118.5 . . ?
C26 N6 H6N 118.5 . . ?
N5 C17 C18 123.2(2) . . ?
N5 C17 C22 117.8(2) . . ?
C18 C17 C22 119.1(2) . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 C23 118.5(2) . . ?
C20 C19 C23 120.8(2) . . ?
C21 C20 C19 118.8(2) . . ?
C21 C20 C24 119.3(2) . . ?
C19 C20 C24 121.9(2) . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C17 120.5(2) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
F4 C23 F5 107.4(3) . . ?
F4 C23 F6 108.0(3) . . ?
F5 C23 F6 104.4(2) . . ?
F4 C23 C19 112.8(2) . . ?
F5 C23 C19 112.0(2) . . ?
F6 C23 C19 111.8(2) . . ?
N4 C24 C20 178.7(3) . . ?
O3 C25 N5 122.8(2) . . ?
O3 C25 C26 122.0(2) . . ?
N5 C25 C26 115.0(2) . . ?
N6 C26 C28 109.6(2) . . ?
N6 C26 C25 111.08(19) . . ?
C28 C26 C25 109.8(2) . . ?
N6 C26 C27 107.2(2) . . ?
C28 C26 C27 110.3(2) . . ?
C25 C26 C27 108.8(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O4 C29 N6 122.5(2) . . ?
O4 C29 C30 120.9(2) . . ?
N6 C29 C30 116.6(2) . . ?
C32 C30 C31 111.3(2) . . ?
C32 C30 C29 116.2(2) . . ?
C31 C30 C29 110.3(2) . . ?
C32 C30 Br2 107.70(19) . . ?
C31 C30 Br2 107.38(19) . . ?
C29 C30 Br2 103.26(16) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C9 N2 C1 C6 -4.4(4) . . . . ?
C9 N2 C1 C2 174.8(3) . . . . ?
C6 C1 C2 C3 2.4(4) . . . . ?
N2 C1 C2 C3 -176.8(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C2 C3 C7 176.5(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C7 C3 C4 C5 -178.9(3) . . . . ?
C2 C3 C4 C8 178.5(3) . . . . ?
C7 C3 C4 C8 1.1(4) . . . . ?
C3 C4 C5 C6 2.5(5) . . . . ?
C8 C4 C5 C6 -177.5(3) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
N2 C1 C6 C5 177.7(3) . . . . ?
C4 C5 C6 C1 -1.0(5) . . . . ?
C4 C3 C7 F1 -171.8(3) . . . . ?
C2 C3 C7 F1 10.8(4) . . . . ?
C4 C3 C7 F3 -50.4(4) . . . . ?
C2 C3 C7 F3 132.2(3) . . . . ?
C4 C3 C7 F2 68.1(4) . . . . ?
C2 C3 C7 F2 -109.3(3) . . . . ?
C1 N2 C9 O1 8.4(5) . . . . ?
C1 N2 C9 C10 -168.4(2) . . . . ?
C13 N3 C10 C11 56.4(4) . . . . ?
C13 N3 C10 C12 -68.3(3) . . . . ?
C13 N3 C10 C9 176.4(2) . . . . ?
O1 C9 C10 N3 13.4(3) . . . . ?
N2 C9 C10 N3 -169.7(2) . . . . ?
O1 C9 C10 C11 132.1(3) . . . . ?
N2 C9 C10 C11 -51.0(3) . . . . ?
O1 C9 C10 C12 -103.4(3) . . . . ?
N2 C9 C10 C12 73.5(3) . . . . ?
C10 N3 C13 O2 4.5(4) . . . . ?
C10 N3 C13 C14 -169.2(2) . . . . ?
O2 C13 C14 C16 -90.0(3) . . . . ?
N3 C13 C14 C16 84.2(3) . . . . ?
O2 C13 C14 C15 33.7(3) . . . . ?
N3 C13 C14 C15 -152.1(2) . . . . ?
O2 C13 C14 Br1 152.5(2) . . . . ?
N3 C13 C14 Br1 -33.3(3) . . . . ?
C25 N5 C17 C18 3.0(4) . . . . ?
C25 N5 C17 C22 -177.5(3) . . . . ?
N5 C17 C18 C19 177.3(2) . . . . ?
C22 C17 C18 C19 -2.2(4) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C17 C18 C19 C23 179.4(3) . . . . ?
C18 C19 C20 C21 1.7(4) . . . . ?
C23 C19 C20 C21 -177.1(3) . . . . ?
C18 C19 C20 C24 -177.8(2) . . . . ?
C23 C19 C20 C24 3.4(4) . . . . ?
C19 C20 C21 C22 -2.2(4) . . . . ?
C24 C20 C21 C22 177.2(2) . . . . ?
C20 C21 C22 C17 0.6(4) . . . . ?
N5 C17 C22 C21 -177.9(2) . . . . ?
C18 C17 C22 C21 1.7(4) . . . . ?
C18 C19 C23 F4 4.8(4) . . . . ?
C20 C19 C23 F4 -176.5(3) . . . . ?
C18 C19 C23 F5 -116.5(3) . . . . ?
C20 C19 C23 F5 62.2(3) . . . . ?
C18 C19 C23 F6 126.7(3) . . . . ?
C20 C19 C23 F6 -54.5(3) . . . . ?
C17 N5 C25 O3 11.9(4) . . . . ?
C17 N5 C25 C26 -172.0(2) . . . . ?
C29 N6 C26 C28 -79.0(3) . . . . ?
C29 N6 C26 C25 42.5(3) . . . . ?
C29 N6 C26 C27 161.3(2) . . . . ?
O3 C25 C26 N6 -134.0(3) . . . . ?
N5 C25 C26 N6 49.9(3) . . . . ?
O3 C25 C26 C28 -12.6(4) . . . . ?
N5 C25 C26 C28 171.3(2) . . . . ?
O3 C25 C26 C27 108.2(3) . . . . ?
N5 C25 C26 C27 -67.9(3) . . . . ?
C26 N6 C29 O4 -9.6(4) . . . . ?
C26 N6 C29 C30 172.3(2) . . . . ?
O4 C29 C30 C32 -152.5(2) . . . . ?
N6 C29 C30 C32 25.6(3) . . . . ?
O4 C29 C30 C31 -24.7(3) . . . . ?
N6 C29 C30 C31 153.4(2) . . . . ?
O4 C29 C30 Br2 89.8(2) . . . . ?
N6 C29 C30 Br2 -92.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.582
_refine_diff_density_min         -1.116
_refine_diff_density_rms         0.069


_database_code_depnum_ccdc_archive 'CCDC 892388'
#######################################################################
#
#                 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_ml029_01
#TrackingRef 'ML029_01.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 F3 N3 O'
_chemical_formula_sum            'C12 H12 F3 N3 O'
_chemical_formula_weight         271.25

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   9.408(2)
_cell_length_b                   12.144(3)
_cell_length_c                   12.488(3)
_cell_angle_alpha                74.568(6)
_cell_angle_beta                 85.875(5)
_cell_angle_gamma                69.212(5)
_cell_volume                     1285.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      35.08

_exptl_crystal_description       piece
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'APEX2 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23402
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         30.00
_reflns_number_total             7383
_reflns_number_gt                6189
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0515P)²+0.2959P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7383
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_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
F1 F 0.75295(9) 0.19328(8) -0.12020(6) 0.0439(2) Uani 1 1 d . . .
F2 F 0.65173(10) 0.35898(8) -0.24684(6) 0.03771(19) Uani 1 1 d . . .
F3 F 0.55769(10) 0.21685(8) -0.21521(7) 0.03836(19) Uani 1 1 d . . .
O1 O 0.29746(9) 0.37274(7) 0.30439(6) 0.02347(16) Uani 1 1 d . . .
N1 N 0.26033(13) 0.48993(11) -0.31654(9) 0.0343(2) Uani 1 1 d . . .
N2 N 0.52194(11) 0.31653(8) 0.21382(7) 0.01901(17) Uani 1 1 d . . .
H2A H 0.6129(18) 0.2751(14) 0.2278(13) 0.028(4) Uiso 1 1 d . . .
N3 N 0.69226(11) 0.22706(10) 0.39305(8) 0.02419(19) Uani 1 1 d . . .
H3A H 0.7279(19) 0.2854(16) 0.3959(14) 0.039(4) Uiso 1 1 d . . .
H3B H 0.744(2) 0.1591(16) 0.4448(15) 0.042(4) Uiso 1 1 d . . .
C1 C 0.46825(12) 0.35287(9) 0.10395(8) 0.01762(18) Uani 1 1 d . . .
C2 C 0.56393(12) 0.29852(9) 0.02676(8) 0.01883(19) Uani 1 1 d . . .
H2 H 0.6618 0.2398 0.0498 0.023 Uiso 1 1 calc R . .
C3 C 0.51603(12) 0.33033(9) -0.08261(8) 0.01911(19) Uani 1 1 d . . .
C4 C 0.37092(12) 0.41715(9) -0.11669(8) 0.0199(2) Uani 1 1 d . . .
C5 C 0.27764(13) 0.47195(10) -0.03991(9) 0.0223(2) Uani 1 1 d . . .
H5 H 0.1798 0.5309 -0.0629 0.027 Uiso 1 1 calc R . .
C6 C 0.32586(12) 0.44150(9) 0.06944(8) 0.0210(2) Uani 1 1 d . . .
H6 H 0.2624 0.4807 0.1210 0.025 Uiso 1 1 calc R . .
C7 C 0.61992(14) 0.27378(11) -0.16552(9) 0.0253(2) Uani 1 1 d . . .
C8 C 0.31326(13) 0.45447(10) -0.22895(9) 0.0248(2) Uani 1 1 d . . .
C9 C 0.43636(12) 0.32570(9) 0.30639(8) 0.01758(19) Uani 1 1 d . . .
C10 C 0.52901(12) 0.26596(9) 0.41595(8) 0.01925(19) Uani 1 1 d . . .
C11 C 0.48800(14) 0.15296(11) 0.47108(10) 0.0292(2) Uani 1 1 d . . .
H11A H 0.5216 0.0951 0.4248 0.044 Uiso 1 1 calc R . .
H11B H 0.3776 0.1769 0.4794 0.044 Uiso 1 1 calc R . .
H11C H 0.5385 0.1144 0.5444 0.044 Uiso 1 1 calc R . .
C12 C 0.48113(19) 0.35754(13) 0.48635(11) 0.0405(3) Uani 1 1 d . . .
H12A H 0.5367 0.3209 0.5579 0.061 Uiso 1 1 calc R . .
H12B H 0.3716 0.3802 0.4989 0.061 Uiso 1 1 calc R . .
H12C H 0.5043 0.4305 0.4475 0.061 Uiso 1 1 calc R . .
F4 F 0.69445(9) 1.03049(6) 0.21705(6) 0.03484(18) Uani 1 1 d . . .
F5 F 0.85979(9) 0.96214(7) 0.10093(6) 0.03366(17) Uani 1 1 d . . .
F6 F 0.67608(9) 0.89422(7) 0.14406(7) 0.03675(19) Uani 1 1 d . . .
O2 O 0.82268(10) 0.97040(7) 0.55890(7) 0.02912(19) Uani 1 1 d . . .
N4 N 0.97612(13) 0.66915(10) 0.06935(9) 0.0332(2) Uani 1 1 d . . .
N5 N 0.94912(10) 0.76614(8) 0.58071(7) 0.01818(17) Uani 1 1 d . . .
H5A H 0.9884(17) 0.6985(14) 0.6303(13) 0.029(4) Uiso 1 1 d . . .
N6 N 0.93302(11) 0.71039(9) 0.79767(8) 0.02337(19) Uani 1 1 d . . .
H6A H 0.8600(18) 0.6787(14) 0.7902(12) 0.028(4) Uiso 1 1 d . . .
H6B H 0.9479(18) 0.6969(15) 0.8692(14) 0.037(4) Uiso 1 1 d . . .
C13 C 0.95230(11) 0.75520(9) 0.47182(8) 0.01653(18) Uani 1 1 d . . .
C14 C 0.86822(11) 0.84994(9) 0.38336(8) 0.01793(19) Uani 1 1 d . . .
H14 H 0.8104 0.9277 0.3947 0.022 Uiso 1 1 calc R . .
C15 C 0.87045(11) 0.82891(9) 0.27948(8) 0.01761(19) Uani 1 1 d . . .
C16 C 0.95761(12) 0.71519(10) 0.26125(8) 0.01922(19) Uani 1 1 d . . .
C17 C 1.04254(12) 0.62186(10) 0.34937(9) 0.0212(2) Uani 1 1 d . . .
H17 H 1.1025 0.5448 0.3376 0.025 Uiso 1 1 calc R . .
C18 C 1.03934(12) 0.64161(9) 0.45345(8) 0.0196(2) Uani 1 1 d . . .
H18 H 1.0966 0.5777 0.5132 0.024 Uiso 1 1 calc R . .
C19 C 0.77513(13) 0.92894(10) 0.18572(9) 0.0234(2) Uani 1 1 d . . .
C20 C 0.96551(13) 0.69118(10) 0.15379(9) 0.0241(2) Uani 1 1 d . . .
C21 C 0.87843(12) 0.86750(10) 0.61919(8) 0.01943(19) Uani 1 1 d . . .
C22 C 0.87436(12) 0.84289(10) 0.74635(8) 0.0201(2) Uani 1 1 d . . .
C23 C 0.71011(13) 0.90420(11) 0.77822(10) 0.0268(2) Uani 1 1 d . . .
H23A H 0.6444 0.8667 0.7558 0.040 Uiso 1 1 calc R . .
H23B H 0.6753 0.9914 0.7404 0.040 Uiso 1 1 calc R . .
H23C H 0.7057 0.8937 0.8588 0.040 Uiso 1 1 calc R . .
C24 C 0.97820(15) 0.90048(13) 0.78124(10) 0.0308(3) Uani 1 1 d . . .
H24A H 0.9766 0.8877 0.8621 0.046 Uiso 1 1 calc R . .
H24B H 0.9422 0.9881 0.7453 0.046 Uiso 1 1 calc R . .
H24C H 1.0823 0.8625 0.7587 0.046 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
F1 C7 1.3346(14) . ?
F2 C7 1.3448(14) . ?
F3 C7 1.3316(14) . ?
O1 C9 1.2254(13) . ?
N1 C8 1.1424(15) . ?
N2 C9 1.3668(13) . ?
N2 C1 1.3970(13) . ?
N2 H2A 0.828(16) . ?
N3 C10 1.4688(15) . ?
N3 H3A 0.894(17) . ?
N3 H3B 0.902(18) . ?
C1 C6 1.3969(15) . ?
C1 C2 1.4024(14) . ?
C2 C3 1.3791(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.4069(15) . ?
C3 C7 1.5017(15) . ?
C4 C5 1.3915(15) . ?
C4 C8 1.4358(14) . ?
C5 C6 1.3816(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C9 C10 1.5337(14) . ?
C10 C12 1.5233(16) . ?
C10 C11 1.5299(15) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
F4 C19 1.3415(14) . ?
F5 C19 1.3407(13) . ?
F6 C19 1.3348(13) . ?
O2 C21 1.2225(13) . ?
N4 C20 1.1444(15) . ?
N5 C21 1.3696(13) . ?
N5 C13 1.3983(13) . ?
N5 H5A 0.861(16) . ?
N6 C22 1.4752(15) . ?
N6 H6A 0.919(16) . ?
N6 H6B 0.876(17) . ?
C13 C18 1.4020(14) . ?
C13 C14 1.4046(13) . ?
C14 C15 1.3846(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.4029(15) . ?
C15 C19 1.5072(14) . ?
C16 C17 1.3977(14) . ?
C16 C20 1.4386(15) . ?
C17 C18 1.3794(14) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C21 C22 1.5359(15) . ?
C22 C24 1.5303(16) . ?
C22 C23 1.5339(15) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C9 N2 C1 126.80(9) . . ?
C9 N2 H2A 113.6(10) . . ?
C1 N2 H2A 118.8(11) . . ?
C10 N3 H3A 109.5(11) . . ?
C10 N3 H3B 110.8(11) . . ?
H3A N3 H3B 107.4(15) . . ?
C6 C1 N2 122.35(9) . . ?
C6 C1 C2 119.97(9) . . ?
N2 C1 C2 117.67(9) . . ?
C3 C2 C1 120.05(10) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.96(9) . . ?
C2 C3 C7 119.92(10) . . ?
C4 C3 C7 120.11(9) . . ?
C5 C4 C3 119.60(9) . . ?
C5 C4 C8 117.33(10) . . ?
C3 C4 C8 123.06(10) . . ?
C6 C5 C4 120.65(10) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.73(10) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
F3 C7 F1 107.49(10) . . ?
F3 C7 F2 106.32(9) . . ?
F1 C7 F2 106.68(10) . . ?
F3 C7 C3 112.08(10) . . ?
F1 C7 C3 112.81(9) . . ?
F2 C7 C3 111.08(10) . . ?
N1 C8 C4 175.78(13) . . ?
O1 C9 N2 124.13(9) . . ?
O1 C9 C10 121.85(9) . . ?
N2 C9 C10 113.96(9) . . ?
N3 C10 C12 113.03(10) . . ?
N3 C10 C11 108.76(9) . . ?
C12 C10 C11 111.23(10) . . ?
N3 C10 C9 109.85(8) . . ?
C12 C10 C9 107.67(9) . . ?
C11 C10 C9 106.05(9) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C21 N5 C13 128.37(9) . . ?
C21 N5 H5A 116.3(10) . . ?
C13 N5 H5A 115.0(10) . . ?
C22 N6 H6A 108.8(9) . . ?
C22 N6 H6B 109.6(11) . . ?
H6A N6 H6B 106.4(14) . . ?
N5 C13 C18 117.10(9) . . ?
N5 C13 C14 123.11(9) . . ?
C18 C13 C14 119.73(9) . . ?
C15 C14 C13 119.34(9) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.84(9) . . ?
C14 C15 C19 119.34(9) . . ?
C16 C15 C19 119.80(9) . . ?
C17 C16 C15 119.46(9) . . ?
C17 C16 C20 118.24(10) . . ?
C15 C16 C20 122.29(10) . . ?
C18 C17 C16 120.04(10) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.58(9) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
F6 C19 F5 106.55(9) . . ?
F6 C19 F4 106.98(9) . . ?
F5 C19 F4 106.37(9) . . ?
F6 C19 C15 111.59(9) . . ?
F5 C19 C15 112.21(9) . . ?
F4 C19 C15 112.74(9) . . ?
N4 C20 C16 177.82(13) . . ?
O2 C21 N5 123.83(10) . . ?
O2 C21 C22 121.47(9) . . ?
N5 C21 C22 114.70(9) . . ?
N6 C22 C24 108.94(9) . . ?
N6 C22 C23 112.51(9) . . ?
C24 C22 C23 109.95(9) . . ?
N6 C22 C21 109.89(8) . . ?
C24 C22 C21 107.42(9) . . ?
C23 C22 C21 108.00(9) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C9 N2 C1 C6 23.55(16) . . . . ?
C9 N2 C1 C2 -157.52(10) . . . . ?
C6 C1 C2 C3 -1.60(15) . . . . ?
N2 C1 C2 C3 179.45(9) . . . . ?
C1 C2 C3 C4 -0.15(15) . . . . ?
C1 C2 C3 C7 178.81(10) . . . . ?
C2 C3 C4 C5 1.11(15) . . . . ?
C7 C3 C4 C5 -177.85(10) . . . . ?
C2 C3 C4 C8 -179.82(10) . . . . ?
C7 C3 C4 C8 1.22(16) . . . . ?
C3 C4 C5 C6 -0.31(16) . . . . ?
C8 C4 C5 C6 -179.43(10) . . . . ?
C4 C5 C6 C1 -1.44(16) . . . . ?
N2 C1 C6 C5 -178.71(10) . . . . ?
C2 C1 C6 C5 2.39(16) . . . . ?
C2 C3 C7 F3 122.63(11) . . . . ?
C4 C3 C7 F3 -58.41(13) . . . . ?
C2 C3 C7 F1 1.13(15) . . . . ?
C4 C3 C7 F1 -179.91(10) . . . . ?
C2 C3 C7 F2 -118.59(11) . . . . ?
C4 C3 C7 F2 60.37(13) . . . . ?
C1 N2 C9 O1 -3.02(16) . . . . ?
C1 N2 C9 C10 174.26(9) . . . . ?
O1 C9 C10 N3 -175.09(9) . . . . ?
N2 C9 C10 N3 7.57(12) . . . . ?
O1 C9 C10 C12 -51.61(14) . . . . ?
N2 C9 C10 C12 131.05(11) . . . . ?
O1 C9 C10 C11 67.55(12) . . . . ?
N2 C9 C10 C11 -109.80(10) . . . . ?
C21 N5 C13 C18 177.18(10) . . . . ?
C21 N5 C13 C14 -5.63(17) . . . . ?
N5 C13 C14 C15 -175.96(9) . . . . ?
C18 C13 C14 C15 1.17(15) . . . . ?
C13 C14 C15 C16 -1.18(15) . . . . ?
C13 C14 C15 C19 177.49(9) . . . . ?
C14 C15 C16 C17 0.35(16) . . . . ?
C19 C15 C16 C17 -178.31(10) . . . . ?
C14 C15 C16 C20 -178.41(10) . . . . ?
C19 C15 C16 C20 2.93(16) . . . . ?
C15 C16 C17 C18 0.51(16) . . . . ?
C20 C16 C17 C18 179.32(10) . . . . ?
C16 C17 C18 C13 -0.51(16) . . . . ?
N5 C13 C18 C17 176.97(10) . . . . ?
C14 C13 C18 C17 -0.33(16) . . . . ?
C14 C15 C19 F6 -121.29(11) . . . . ?
C16 C15 C19 F6 57.39(13) . . . . ?
C14 C15 C19 F5 119.21(11) . . . . ?
C16 C15 C19 F5 -62.11(13) . . . . ?
C14 C15 C19 F4 -0.87(14) . . . . ?
C16 C15 C19 F4 177.81(9) . . . . ?
C13 N5 C21 O2 -10.44(18) . . . . ?
C13 N5 C21 C22 169.86(10) . . . . ?
O2 C21 C22 N6 173.38(10) . . . . ?
N5 C21 C22 N6 -6.92(13) . . . . ?
O2 C21 C22 C24 -68.24(14) . . . . ?
N5 C21 C22 C24 111.47(11) . . . . ?
O2 C21 C22 C23 50.31(14) . . . . ?
N5 C21 C22 C23 -129.98(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.052


_database_code_depnum_ccdc_archive 'CCDC 893326'
#######################################################################
#
#                 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_ml014_01
#TrackingRef 'ML014_01.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Br F3 N2 O'
_chemical_formula_sum            'C12 H10 Br F3 N2 O'
_chemical_formula_weight         335.13

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   P21/c
_symmetry_space_group_name_Hall  -P2ybc


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.6717(3)
_cell_length_b                   22.0719(12)
_cell_length_c                   10.2761(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.2800(10)
_cell_angle_gamma                90.00
_cell_volume                     1252.02(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6039
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      34.99

_exptl_crystal_description       piece
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    3.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5877
_exptl_absorpt_correction_T_max  0.6363
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'APEX2 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21258
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         35.00
_reflns_number_total             5508
_reflns_number_gt                4336
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0321P)²+0.6178P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5508
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_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 1.20980(3) 0.693781(7) 0.562394(17) 0.03196(6) Uani 1 1 d . . .
F1 F 0.6865(3) 0.95079(5) 0.12838(14) 0.0582(4) Uani 1 1 d . . .
F2 F 0.3034(3) 0.96698(5) 0.10070(12) 0.0546(4) Uani 1 1 d . . .
F3 F 0.55789(19) 1.02280(4) 0.23234(11) 0.0300(2) Uani 1 1 d . . .
O1 O 0.7776(2) 0.75689(5) 0.22879(10) 0.0226(2) Uani 1 1 d . . .
N1 N 0.0967(3) 1.03373(6) 0.37211(17) 0.0332(3) Uani 1 1 d . . .
N2 N 0.7724(2) 0.77685(5) 0.44463(11) 0.0170(2) Uani 1 1 d . . .
H2N H 0.800(4) 0.7640(9) 0.522(2) 0.024(5) Uiso 1 1 d . . .
C1 C 0.6298(2) 0.83005(6) 0.42203(13) 0.0153(2) Uani 1 1 d . . .
C2 C 0.6454(2) 0.87099(6) 0.32067(13) 0.0168(2) Uani 1 1 d . . .
H2 H 0.7520 0.8632 0.2636 0.020 Uiso 1 1 calc R . .
C3 C 0.5046(3) 0.92300(6) 0.30383(13) 0.0179(2) Uani 1 1 d . . .
C4 C 0.3495(2) 0.93513(6) 0.38886(14) 0.0184(2) Uani 1 1 d . . .
C5 C 0.3360(3) 0.89449(6) 0.49064(15) 0.0207(3) Uani 1 1 d . . .
H5 H 0.2316 0.9025 0.5488 0.025 Uiso 1 1 calc R . .
C6 C 0.4760(3) 0.84213(6) 0.50678(14) 0.0197(2) Uani 1 1 d . . .
H6 H 0.4666 0.8144 0.5761 0.024 Uiso 1 1 calc R . .
C7 C 0.5143(3) 0.96569(6) 0.19126(16) 0.0276(3) Uani 1 1 d . . .
C8 C 0.2066(3) 0.98984(6) 0.37703(16) 0.0235(3) Uani 1 1 d . . .
C9 C 0.8377(2) 0.74368(5) 0.34734(13) 0.0146(2) Uani 1 1 d . . .
C10 C 0.9772(2) 0.68439(5) 0.38858(13) 0.0153(2) Uani 1 1 d . . .
C11 C 1.1246(3) 0.66729(7) 0.28818(17) 0.0270(3) Uani 1 1 d . . .
H11A H 1.0160 0.6619 0.1998 0.041 Uiso 1 1 calc R . .
H11B H 1.2115 0.6294 0.3160 0.041 Uiso 1 1 calc R . .
H11C H 1.2413 0.6995 0.2839 0.041 Uiso 1 1 calc R . .
C12 C 0.7997(3) 0.63473(7) 0.4022(2) 0.0309(4) Uani 1 1 d . . .
H12A H 0.7136 0.6461 0.4711 0.046 Uiso 1 1 calc R . .
H12B H 0.8880 0.5968 0.4278 0.046 Uiso 1 1 calc R . .
H12C H 0.6828 0.6292 0.3166 0.046 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
Br1 C10 1.9725(13) . ?
F1 C7 1.331(2) . ?
F2 C7 1.336(2) . ?
F3 C7 1.3343(17) . ?
O1 C9 1.2224(16) . ?
N1 C8 1.1471(19) . ?
N2 C9 1.3576(17) . ?
N2 C1 1.4143(16) . ?
N2 H2N 0.83(2) . ?
C1 C6 1.3928(19) . ?
C1 C2 1.3971(18) . ?
C2 C3 1.3863(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(2) . ?
C3 C7 1.503(2) . ?
C4 C5 1.393(2) . ?
C4 C8 1.4437(19) . ?
C5 C6 1.3902(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C9 C10 1.5375(17) . ?
C10 C12 1.5166(19) . ?
C10 C11 1.517(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C9 N2 C1 124.70(11) . . ?
C9 N2 H2N 120.1(14) . . ?
C1 N2 H2N 114.8(14) . . ?
C6 C1 C2 119.90(11) . . ?
C6 C1 N2 118.23(12) . . ?
C2 C1 N2 121.84(12) . . ?
C3 C2 C1 119.69(13) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.44(12) . . ?
C2 C3 C7 119.58(13) . . ?
C4 C3 C7 119.96(12) . . ?
C5 C4 C3 119.73(12) . . ?
C5 C4 C8 118.36(13) . . ?
C3 C4 C8 121.89(13) . . ?
C6 C5 C4 119.77(13) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.47(13) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
F1 C7 F3 106.47(15) . . ?
F1 C7 F2 107.86(15) . . ?
F3 C7 F2 105.75(13) . . ?
F1 C7 C3 112.30(13) . . ?
F3 C7 C3 112.68(13) . . ?
F2 C7 C3 111.38(15) . . ?
N1 C8 C4 177.66(18) . . ?
O1 C9 N2 122.99(11) . . ?
O1 C9 C10 119.06(11) . . ?
N2 C9 C10 117.79(11) . . ?
C12 C10 C11 111.36(12) . . ?
C12 C10 C9 109.27(11) . . ?
C11 C10 C9 110.69(11) . . ?
C12 C10 Br1 108.19(10) . . ?
C11 C10 Br1 106.48(9) . . ?
C9 C10 Br1 110.79(8) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C9 N2 C1 C6 147.44(14) . . . . ?
C9 N2 C1 C2 -34.5(2) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
N2 C1 C2 C3 -178.97(12) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C1 C2 C3 C7 -177.52(13) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C7 C3 C4 C5 178.11(14) . . . . ?
C2 C3 C4 C8 177.85(13) . . . . ?
C7 C3 C4 C8 -3.8(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C8 C4 C5 C6 -178.40(14) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
N2 C1 C6 C5 178.56(13) . . . . ?
C2 C3 C7 F1 -7.6(2) . . . . ?
C4 C3 C7 F1 173.95(14) . . . . ?
C2 C3 C7 F3 -127.89(15) . . . . ?
C4 C3 C7 F3 53.7(2) . . . . ?
C2 C3 C7 F2 113.46(16) . . . . ?
C4 C3 C7 F2 -64.95(18) . . . . ?
C1 N2 C9 O1 -0.2(2) . . . . ?
C1 N2 C9 C10 -175.48(12) . . . . ?
O1 C9 C10 C12 -94.55(16) . . . . ?
N2 C9 C10 C12 80.95(15) . . . . ?
O1 C9 C10 C11 28.45(17) . . . . ?
N2 C9 C10 C11 -156.06(13) . . . . ?
O1 C9 C10 Br1 146.34(11) . . . . ?
N2 C9 C10 Br1 -38.17(14) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        35.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.796
_refine_diff_density_min         -1.148
_refine_diff_density_rms         0.074


_database_code_depnum_ccdc_archive 'CCDC 894556'
#######################################################################
#
#                 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_ml018_new
#TrackingRef 'ML018_01.cif'


_refine_special_details          
;
alert arises from failure of hirshfeld test. This is caused by cyano group on the aromatic ring which does not obey the rigid bond model
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F3 N3 O3, C3 H7 N O'
_chemical_formula_sum            'C15 H17 F3 N4 O4'
_chemical_formula_weight         374.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.373(4)
_cell_length_b                   11.959(4)
_cell_length_c                   11.210(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.965(5)
_cell_angle_gamma                90.00
_cell_volume                     1714.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1824
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.38

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  .
_exptl_absorpt_correction_T_max  .
_exptl_absorpt_process_details   .

_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  'apex2 ccd'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9117
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3366
_reflns_number_gt                2588
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0310P)²+0.3988P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   
'H2N from delta-F; other H atoms placed geometrically'
_refine_ls_hydrogen_treatment    'freely refined; riding model'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3366
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
F1 F 0.10569(9) 0.53329(10) 0.41725(9) 0.0338(3) Uani 1 1 d . . .
F2 F 0.16143(9) 0.70136(10) 0.43904(9) 0.0302(3) Uani 1 1 d . . .
F3 F 0.03439(8) 0.65369(11) 0.50706(10) 0.0335(3) Uani 1 1 d . . .
O1 O 0.46088(10) 0.34636(12) 0.95795(11) 0.0267(3) Uani 1 1 d . . .
O2 O 0.59556(10) 0.14479(12) 0.97077(13) 0.0311(4) Uani 1 1 d . . .
O3 O 0.48408(11) 0.11372(13) 1.07239(11) 0.0316(4) Uani 1 1 d . . .
N1 N 0.19374(13) 0.88092(15) 0.66610(15) 0.0290(4) Uani 1 1 d . . .
N2 N 0.32790(12) 0.33794(14) 0.77714(13) 0.0178(3) Uani 1 1 d . . .
H2N H 0.2945(15) 0.2931(18) 0.7167(18) 0.022(5) Uiso 1 1 d . . .
N3 N 0.50620(12) 0.13803(13) 0.97790(14) 0.0218(4) Uani 1 1 d . . .
C1 C 0.30051(13) 0.45059(16) 0.76102(15) 0.0166(4) Uani 1 1 d . . .
C2 C 0.23046(13) 0.48032(16) 0.64546(15) 0.0167(4) Uani 1 1 d . . .
H2 H 0.2036 0.4254 0.5860 0.020 Uiso 1 1 calc R . .
C3 C 0.20138(13) 0.58960(16) 0.61977(15) 0.0175(4) Uani 1 1 d . . .
C4 C 0.23976(13) 0.67262(16) 0.70907(15) 0.0168(4) Uani 1 1 d . . .
C5 C 0.30663(13) 0.64211(16) 0.82491(15) 0.0183(4) Uani 1 1 d . . .
H5 H 0.3312 0.6966 0.8855 0.022 Uiso 1 1 calc R . .
C6 C 0.33697(13) 0.53263(16) 0.85114(15) 0.0179(4) Uani 1 1 d . . .
H6 H 0.3817 0.5136 0.9289 0.022 Uiso 1 1 calc R . .
C7 C 0.12642(14) 0.61900(16) 0.49576(16) 0.0202(4) Uani 1 1 d . . .
C8 C 0.21422(14) 0.78847(18) 0.68457(15) 0.0207(4) Uani 1 1 d . . .
C9 C 0.40537(13) 0.29333(16) 0.87179(15) 0.0171(4) Uani 1 1 d . . .
C10 C 0.41665(13) 0.16629(16) 0.86073(15) 0.0173(4) Uani 1 1 d . . .
C11 C 0.45010(15) 0.13509(17) 0.74713(16) 0.0252(4) Uani 1 1 d . . .
H11A H 0.4673 0.0570 0.7505 0.038 Uiso 1 1 calc R . .
H11B H 0.5102 0.1784 0.7459 0.038 Uiso 1 1 calc R . .
H11C H 0.3940 0.1500 0.6730 0.038 Uiso 1 1 calc R . .
C12 C 0.31950(14) 0.10465(17) 0.86702(16) 0.0220(4) Uani 1 1 d . . .
H12A H 0.2635 0.1193 0.7927 0.033 Uiso 1 1 calc R . .
H12B H 0.2999 0.1298 0.9384 0.033 Uiso 1 1 calc R . .
H12C H 0.3334 0.0258 0.8740 0.033 Uiso 1 1 calc R . .
O4 O 0.20600(10) 0.27225(12) 1.05612(11) 0.0265(3) Uani 1 1 d . . .
N4 N 0.10379(11) 0.38202(14) 0.90301(13) 0.0204(4) Uani 1 1 d . . .
C13 C 0.16869(14) 0.36406(17) 1.01608(16) 0.0222(4) Uani 1 1 d . . .
H13 H 0.1875 0.4252 1.0691 0.027 Uiso 1 1 calc R . .
C14 C 0.06296(15) 0.49305(17) 0.86528(16) 0.0251(4) Uani 1 1 d . . .
H14A H 0.0903 0.5446 0.9326 0.038 Uiso 1 1 calc R . .
H14B H -0.0119 0.4917 0.8444 0.038 Uiso 1 1 calc R . .
H14C H 0.0835 0.5163 0.7939 0.038 Uiso 1 1 calc R . .
C15 C 0.07137(14) 0.29250(17) 0.81308(16) 0.0239(4) Uani 1 1 d . . .
H15A H 0.1006 0.2231 0.8505 0.036 Uiso 1 1 calc R . .
H15B H 0.0955 0.3077 0.7420 0.036 Uiso 1 1 calc R . .
H15C H -0.0035 0.2873 0.7870 0.036 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
F1 C7 1.327(2) . ?
F2 C7 1.329(2) . ?
F3 C7 1.339(2) . ?
O1 C9 1.211(2) . ?
O2 N3 1.223(2) . ?
O3 N3 1.215(2) . ?
N1 C8 1.143(3) . ?
N2 C9 1.357(2) . ?
N2 C1 1.394(2) . ?
N2 H2N 0.88(2) . ?
N3 C10 1.535(2) . ?
C1 C6 1.391(2) . ?
C1 C2 1.405(2) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 C7 1.499(2) . ?
C4 C5 1.393(2) . ?
C4 C8 1.434(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C9 C10 1.535(3) . ?
C10 C12 1.513(3) . ?
C10 C11 1.514(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O4 C13 1.235(2) . ?
N4 C13 1.328(2) . ?
N4 C15 1.448(2) . ?
N4 C14 1.451(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C9 N2 C1 126.37(16) . . ?
C9 N2 H2N 117.7(13) . . ?
C1 N2 H2N 115.8(13) . . ?
O3 N3 O2 124.31(15) . . ?
O3 N3 C10 118.09(15) . . ?
O2 N3 C10 117.56(15) . . ?
C6 C1 N2 124.38(15) . . ?
C6 C1 C2 119.30(17) . . ?
N2 C1 C2 116.32(16) . . ?
C3 C2 C1 120.48(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.33(15) . . ?
C2 C3 C7 119.38(16) . . ?
C4 C3 C7 120.28(17) . . ?
C5 C4 C3 118.91(17) . . ?
C5 C4 C8 118.92(16) . . ?
C3 C4 C8 122.16(15) . . ?
C6 C5 C4 121.13(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.79(15) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
F1 C7 F2 106.84(14) . . ?
F1 C7 F3 106.39(15) . . ?
F2 C7 F3 106.10(15) . . ?
F1 C7 C3 112.81(16) . . ?
F2 C7 C3 112.57(15) . . ?
F3 C7 C3 111.67(14) . . ?
N1 C8 C4 179.4(2) . . ?
O1 C9 N2 124.59(18) . . ?
O1 C9 C10 122.05(15) . . ?
N2 C9 C10 113.35(15) . . ?
C12 C10 C11 112.79(15) . . ?
C12 C10 N3 108.60(14) . . ?
C11 C10 N3 108.49(14) . . ?
C12 C10 C9 111.86(15) . . ?
C11 C10 C9 111.83(15) . . ?
N3 C10 C9 102.67(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 N4 C15 121.63(17) . . ?
C13 N4 C14 120.78(16) . . ?
C15 N4 C14 117.59(14) . . ?
O4 C13 N4 124.95(18) . . ?
O4 C13 H13 117.5 . . ?
N4 C13 H13 117.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051

#=== END of CIF


_database_code_depnum_ccdc_archive 'CCDC 904089'
