# Electronic Supplementary Material (ESI) for Chemical Science.
# 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 Br N2 O3'
_chemical_formula_weight         477.35

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

_cell_length_a                   9.7989(16)
_cell_length_b                   9.7523(16)
_cell_length_c                   22.829(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.326(2)
_cell_angle_gamma                90.00
_cell_volume                     2181.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    3488
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      24.67
_exptl_crystal_description       'stick '
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    1.914
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_T_max  0.8317
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            12323
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         27.55
_reflns_number_total             8658
_reflns_number_gt                6637
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0232P)²+2.6527P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.039(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8658
_refine_ls_number_parameters     561
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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 0.32075(9) -0.30077(7) 0.22014(3) 0.0537(2) Uani 1 1 d . . .
Br2 Br 0.31807(8) 1.36855(6) 0.28032(3) 0.0454(2) Uani 1 1 d . . .
C1 C 0.7428(7) 0.6695(6) 0.0183(3) 0.0352(15) Uani 1 1 d . . .
H1 H 0.7195 0.6153 -0.0149 0.042 Uiso 1 1 calc R . .
C2 C 0.7552(7) 0.6199(6) 0.0744(2) 0.0300(14) Uani 1 1 d . . .
C3 C 0.7920(7) 0.7353(6) 0.1096(3) 0.0318(15) Uani 1 1 d . . .
C4 C 0.8193(7) 0.7543(7) 0.1695(3) 0.0386(16) Uani 1 1 d . . .
H4 H 0.8142 0.6794 0.1960 0.046 Uiso 1 1 calc R . .
C5 C 0.8540(7) 0.8844(7) 0.1894(3) 0.0411(16) Uani 1 1 d . . .
H5 H 0.8727 0.8984 0.2298 0.049 Uiso 1 1 calc R . .
C6 C 0.8616(8) 0.9953(8) 0.1505(3) 0.0477(19) Uani 1 1 d . . .
H6 H 0.8890 1.0827 0.1647 0.057 Uiso 1 1 calc R . .
C7 C 0.8300(8) 0.9796(7) 0.0922(3) 0.049(2) Uani 1 1 d . . .
H7 H 0.8313 1.0559 0.0664 0.059 Uiso 1 1 calc R . .
C8 C 0.7959(6) 0.8491(7) 0.0719(2) 0.0314(14) Uani 1 1 d . . .
C9 C 0.8290(7) 0.4276(7) 0.1404(3) 0.0332(15) Uani 1 1 d . . .
C10 C 0.7280(6) 0.4743(6) 0.0938(2) 0.0292(13) Uani 1 1 d . . .
C11 C 0.5897(6) 0.4746(6) 0.1246(2) 0.0306(14) Uani 1 1 d . . .
H11A H 0.5961 0.5344 0.1595 0.037 Uiso 1 1 calc R . .
H11B H 0.5209 0.5151 0.0978 0.037 Uiso 1 1 calc R . .
C12 C 0.7318(6) 0.3750(7) 0.0403(2) 0.0326(14) Uani 1 1 d . . .
C13 C 0.8573(7) 0.3271(7) 0.0201(3) 0.0397(16) Uani 1 1 d . . .
H13 H 0.9390 0.3547 0.0393 0.048 Uiso 1 1 calc R . .
C14 C 0.8637(7) 0.2390(7) -0.0281(3) 0.0408(16) Uani 1 1 d . . .
H14 H 0.9490 0.2054 -0.0414 0.049 Uiso 1 1 calc R . .
C15 C 0.7438(7) 0.2016(8) -0.0560(2) 0.0416(16) Uani 1 1 d . . .
H15 H 0.7462 0.1402 -0.0883 0.050 Uiso 1 1 calc R . .
C16 C 0.6223(8) 0.2527(8) -0.0372(3) 0.049(2) Uani 1 1 d . . .
H16 H 0.5408 0.2292 -0.0576 0.058 Uiso 1 1 calc R . .
C17 C 0.6157(7) 0.3384(7) 0.0111(3) 0.0421(17) Uani 1 1 d . . .
H17 H 0.5299 0.3717 0.0239 0.051 Uiso 1 1 calc R . .
C18 C 0.4214(6) 0.2828(7) 0.1281(2) 0.0307(14) Uani 1 1 d . . .
C19 C 0.3956(6) 0.1373(6) 0.1491(2) 0.0293(14) Uani 1 1 d . . .
C20 C 0.5041(7) 0.0532(7) 0.1654(3) 0.0499(19) Uani 1 1 d . . .
H20 H 0.5949 0.0868 0.1629 0.060 Uiso 1 1 calc R . .
C21 C 0.4814(8) -0.0768(7) 0.1849(3) 0.0499(19) Uani 1 1 d . . .
H21 H 0.5557 -0.1348 0.1951 0.060 Uiso 1 1 calc R . .
C22 C 0.3482(7) -0.1231(7) 0.1895(2) 0.0385(15) Uani 1 1 d . . .
C23 C 0.2413(8) -0.0457(7) 0.1728(3) 0.0469(18) Uani 1 1 d . . .
H23 H 0.1506 -0.0799 0.1749 0.056 Uiso 1 1 calc R . .
C24 C 0.2683(7) 0.0898(7) 0.1517(3) 0.0409(16) Uani 1 1 d . . .
H24 H 0.1946 0.1465 0.1395 0.049 Uiso 1 1 calc R . .
C25 C 1.0614(7) 0.4315(8) 0.1711(3) 0.0461(18) Uani 1 1 d . . .
H25A H 1.1094 0.5126 0.1860 0.069 Uiso 1 1 calc R . .
H25B H 1.1270 0.3693 0.1527 0.069 Uiso 1 1 calc R . .
H25C H 1.0165 0.3843 0.2036 0.069 Uiso 1 1 calc R . .
C26 C 0.7437(5) 0.3986(5) 0.4816(2) 0.0205(12) Uani 1 1 d . . .
H26 H 0.7216 0.4530 0.5148 0.025 Uiso 1 1 calc R . .
C27 C 0.7550(5) 0.4467(5) 0.4261(2) 0.0173(11) Uani 1 1 d . . .
C28 C 0.7965(5) 0.2166(6) 0.4275(2) 0.0222(12) Uani 1 1 d . . .
C29 C 0.8312(6) 0.0866(6) 0.4075(3) 0.0307(14) Uani 1 1 d . . .
H29 H 0.8340 0.0105 0.4334 0.037 Uiso 1 1 calc R . .
C30 C 0.8616(6) 0.0710(6) 0.3487(3) 0.0323(15) Uani 1 1 d . . .
H30 H 0.8876 -0.0165 0.3342 0.039 Uiso 1 1 calc R . .
C31 C 0.8541(6) 0.1837(7) 0.3103(2) 0.0303(14) Uani 1 1 d . . .
H31 H 0.8727 0.1708 0.2699 0.036 Uiso 1 1 calc R . .
C32 C 0.8203(5) 0.3122(6) 0.3304(2) 0.0228(12) Uani 1 1 d . . .
H32 H 0.8159 0.3876 0.3042 0.027 Uiso 1 1 calc R . .
C33 C 0.7923(5) 0.3309(5) 0.3899(2) 0.0212(12) Uani 1 1 d . . .
C34 C 0.5842(6) 0.5922(6) 0.3763(2) 0.0231(12) Uani 1 1 d . . .
H34A H 0.5867 0.5308 0.3418 0.028 Uiso 1 1 calc R . .
H34B H 0.5167 0.5546 0.4041 0.028 Uiso 1 1 calc R . .
C35 C 0.7277(6) 0.5934(5) 0.4062(2) 0.0192(11) Uani 1 1 d . . .
C36 C 0.8300(6) 0.6393(6) 0.3601(2) 0.0218(12) Uani 1 1 d . . .
C37 C 1.0592(6) 0.6354(7) 0.3282(3) 0.0331(14) Uani 1 1 d . . .
H37A H 1.0491 0.5778 0.2932 0.050 Uiso 1 1 calc R . .
H37B H 1.1508 0.6233 0.3448 0.050 Uiso 1 1 calc R . .
H37C H 1.0459 0.7318 0.3174 0.050 Uiso 1 1 calc R . .
C38 C 0.4204(6) 0.7834(6) 0.3724(2) 0.0216(12) Uani 1 1 d . . .
C39 C 0.3959(6) 0.9275(6) 0.3517(2) 0.0204(12) Uani 1 1 d . . .
C40 C 0.2665(6) 0.9794(6) 0.3488(3) 0.0283(13) Uani 1 1 d . . .
H40 H 0.1923 0.9242 0.3614 0.034 Uiso 1 1 calc R . .
C41 C 0.2406(6) 1.1109(6) 0.3279(3) 0.0342(15) Uani 1 1 d . . .
H41 H 0.1500 1.1452 0.3256 0.041 Uiso 1 1 calc R . .
C42 C 0.3487(6) 1.1894(6) 0.3108(2) 0.0275(13) Uani 1 1 d . . .
C43 C 0.4788(6) 1.1420(6) 0.3144(3) 0.0362(15) Uani 1 1 d . . .
H43 H 0.5524 1.1990 0.3027 0.043 Uiso 1 1 calc R . .
C44 C 0.5042(7) 1.0132(7) 0.3347(3) 0.0370(15) Uani 1 1 d . . .
H44 H 0.5955 0.9811 0.3375 0.044 Uiso 1 1 calc R . .
C45 C 0.7334(5) 0.6915(6) 0.4592(2) 0.0200(11) Uani 1 1 d . . .
C46 C 0.6171(6) 0.7277(7) 0.4889(2) 0.0298(14) Uani 1 1 d . . .
H46 H 0.5311 0.6937 0.4761 0.036 Uiso 1 1 calc R . .
C47 C 0.6238(7) 0.8129(7) 0.5373(3) 0.0366(16) Uani 1 1 d . . .
H47 H 0.5424 0.8359 0.5574 0.044 Uiso 1 1 calc R . .
C48 C 0.7462(6) 0.8648(7) 0.5567(2) 0.0340(14) Uani 1 1 d . . .
H48 H 0.7493 0.9251 0.5894 0.041 Uiso 1 1 calc R . .
C49 C 0.8642(6) 0.8286(6) 0.5284(2) 0.0283(13) Uani 1 1 d . . .
H49 H 0.9493 0.8636 0.5417 0.034 Uiso 1 1 calc R . .
C50 C 0.8599(6) 0.7417(6) 0.4807(2) 0.0251(12) Uani 1 1 d . . .
H50 H 0.9423 0.7154 0.4621 0.030 Uiso 1 1 calc R . .
N1 N 0.7682(6) 0.8051(5) 0.0165(2) 0.0372(13) Uani 1 1 d . . .
H1A H 0.7671 0.8566 -0.0152 0.045 Uiso 1 1 calc R . .
N2 N 0.5420(5) 0.3391(5) 0.1430(2) 0.0316(12) Uani 1 1 d . . .
H2A H 0.5967 0.2905 0.1656 0.038 Uiso 1 1 calc R . .
N3 N 0.7686(5) 0.2606(5) 0.4831(2) 0.0255(11) Uani 1 1 d . . .
H3A H 0.7669 0.2087 0.5147 0.031 Uiso 1 1 calc R . .
N4 N 0.5404(4) 0.7276(5) 0.35773(18) 0.0240(11) Uani 1 1 d . . .
H4A H 0.5957 0.7758 0.3356 0.029 Uiso 1 1 calc R . .
O1 O 0.9605(5) 0.4730(5) 0.12856(18) 0.0401(11) Uani 1 1 d . . .
O2 O 0.8039(4) 0.3582(6) 0.18180(17) 0.0411(11) Uani 1 1 d . . .
O3 O 0.3299(4) 0.3448(5) 0.10000(17) 0.0387(11) Uani 1 1 d . . .
O4 O 0.9577(4) 0.5959(4) 0.37136(16) 0.0278(9) Uani 1 1 d . . .
O5 O 0.8019(4) 0.7079(5) 0.31783(16) 0.0346(10) Uani 1 1 d . . .
O6 O 0.3324(4) 0.7223(4) 0.40112(15) 0.0260(9) 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 C22 1.888(7) . ?
Br2 C42 1.904(6) . ?
C1 N1 1.346(8) . ?
C1 C2 1.374(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.429(8) . ?
C2 C10 1.512(8) . ?
C3 C4 1.404(8) . ?
C3 C8 1.406(8) . ?
C4 C5 1.389(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(9) . ?
C7 H7 0.9500 . ?
C8 N1 1.362(7) . ?
C9 O2 1.189(7) . ?
C9 O1 1.391(8) . ?
C9 C10 1.519(9) . ?
C10 C11 1.529(8) . ?
C10 C12 1.559(8) . ?
C11 N2 1.464(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.363(8) . ?
C12 C13 1.396(9) . ?
C13 C14 1.398(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.362(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O3 1.254(7) . ?
C18 N2 1.346(7) . ?
C18 C19 1.519(9) . ?
C19 C24 1.332(9) . ?
C19 C20 1.392(9) . ?
C20 C21 1.362(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(10) . ?
C21 H21 0.9500 . ?
C22 C23 1.345(10) . ?
C23 C24 1.432(10) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 O1 1.440(7) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.358(7) . ?
C26 N3 1.368(7) . ?
C26 H26 0.9500 . ?
C27 C33 1.448(7) . ?
C27 C35 1.523(7) . ?
C28 N3 1.370(7) . ?
C28 C29 1.391(8) . ?
C28 C33 1.407(7) . ?
C29 C30 1.383(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.409(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.376(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.398(8) . ?
C32 H32 0.9500 . ?
C34 N4 1.451(7) . ?
C34 C35 1.560(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.524(8) . ?
C35 C45 1.544(7) . ?
C36 O5 1.206(7) . ?
C36 O4 1.344(7) . ?
C37 O4 1.456(7) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 O6 1.239(7) . ?
C38 N4 1.340(7) . ?
C38 C39 1.502(8) . ?
C39 C40 1.367(8) . ?
C39 C44 1.406(8) . ?
C40 C41 1.391(8) . ?
C40 H40 0.9500 . ?
C41 C42 1.365(9) . ?
C41 H41 0.9500 . ?
C42 C43 1.358(8) . ?
C43 C44 1.361(9) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C46 1.375(7) . ?
C45 C50 1.417(8) . ?
C46 C47 1.383(8) . ?
C46 H46 0.9500 . ?
C47 C48 1.373(9) . ?
C47 H47 0.9500 . ?
C48 C49 1.374(8) . ?
C48 H48 0.9500 . ?
C49 C50 1.380(7) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
N4 H4A 0.8800 . ?

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
N1 C1 C2 111.0(5) . . ?
N1 C1 H1 124.5 . . ?
C2 C1 H1 124.5 . . ?
C1 C2 C3 105.6(5) . . ?
C1 C2 C10 126.1(5) . . ?
C3 C2 C10 128.2(5) . . ?
C4 C3 C8 119.2(6) . . ?
C4 C3 C2 134.3(6) . . ?
C8 C3 C2 106.5(5) . . ?
C5 C4 C3 118.9(6) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.8(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 121.0(7) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 118.5(7) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
N1 C8 C7 130.1(6) . . ?
N1 C8 C3 108.3(5) . . ?
C7 C8 C3 121.5(6) . . ?
O2 C9 O1 122.1(6) . . ?
O2 C9 C10 126.2(6) . . ?
O1 C9 C10 111.7(5) . . ?
C2 C10 C9 111.9(5) . . ?
C2 C10 C11 107.0(5) . . ?
C9 C10 C11 104.7(5) . . ?
C2 C10 C12 110.4(5) . . ?
C9 C10 C12 110.1(5) . . ?
C11 C10 C12 112.7(5) . . ?
N2 C11 C10 114.5(5) . . ?
N2 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
N2 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C17 C12 C13 119.0(6) . . ?
C17 C12 C10 121.5(6) . . ?
C13 C12 C10 119.5(5) . . ?
C12 C13 C14 120.6(6) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 118.9(6) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C16 C15 C14 120.1(6) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 121.0(6) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C12 C17 C16 120.4(7) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
O3 C18 N2 123.9(6) . . ?
O3 C18 C19 119.5(6) . . ?
N2 C18 C19 116.6(6) . . ?
C24 C19 C20 119.8(6) . . ?
C24 C19 C18 119.8(6) . . ?
C20 C19 C18 120.4(6) . . ?
C21 C20 C19 120.7(7) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 118.9(7) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 121.9(7) . . ?
C23 C22 Br1 120.5(6) . . ?
C21 C22 Br1 117.6(5) . . ?
C22 C23 C24 117.9(7) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C19 C24 C23 120.7(7) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 N3 110.4(5) . . ?
C27 C26 H26 124.8 . . ?
N3 C26 H26 124.8 . . ?
C26 C27 C33 106.6(5) . . ?
C26 C27 C35 126.0(5) . . ?
C33 C27 C35 127.4(4) . . ?
N3 C28 C29 129.9(5) . . ?
N3 C28 C33 108.2(5) . . ?
C29 C28 C33 121.9(5) . . ?
C30 C29 C28 118.3(6) . . ?
C30 C29 H29 120.9 . . ?
C28 C29 H29 120.9 . . ?
C29 C30 C31 120.5(6) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C32 C31 C30 120.9(5) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C33 119.5(5) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C32 C33 C28 118.9(5) . . ?
C32 C33 C27 135.0(5) . . ?
C28 C33 C27 106.1(5) . . ?
N4 C34 C35 112.7(4) . . ?
N4 C34 H34A 109.1 . . ?
C35 C34 H34A 109.1 . . ?
N4 C34 H34B 109.1 . . ?
C35 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
C27 C35 C36 111.5(4) . . ?
C27 C35 C45 110.1(4) . . ?
C36 C35 C45 109.8(4) . . ?
C27 C35 C34 106.2(4) . . ?
C36 C35 C34 107.1(4) . . ?
C45 C35 C34 112.1(4) . . ?
O5 C36 O4 122.3(5) . . ?
O5 C36 C35 124.6(5) . . ?
O4 C36 C35 113.0(5) . . ?
O4 C37 H37A 109.5 . . ?
O4 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O4 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O6 C38 N4 123.5(5) . . ?
O6 C38 C39 120.4(5) . . ?
N4 C38 C39 116.1(5) . . ?
C40 C39 C44 117.9(6) . . ?
C40 C39 C38 120.5(5) . . ?
C44 C39 C38 121.6(5) . . ?
C39 C40 C41 121.7(6) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C42 C41 C40 118.3(6) . . ?
C42 C41 H41 120.8 . . ?
C40 C41 H41 120.8 . . ?
C43 C42 C41 121.4(6) . . ?
C43 C42 Br2 118.7(5) . . ?
C41 C42 Br2 119.9(4) . . ?
C42 C43 C44 120.3(6) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C43 C44 C39 120.4(6) . . ?
C43 C44 H44 119.8 . . ?
C39 C44 H44 119.8 . . ?
C46 C45 C50 117.8(5) . . ?
C46 C45 C35 121.3(5) . . ?
C50 C45 C35 120.8(5) . . ?
C45 C46 C47 120.8(5) . . ?
C45 C46 H46 119.6 . . ?
C47 C46 H46 119.6 . . ?
C48 C47 C46 121.1(6) . . ?
C48 C47 H47 119.4 . . ?
C46 C47 H47 119.4 . . ?
C47 C48 C49 119.3(6) . . ?
C47 C48 H48 120.4 . . ?
C49 C48 H48 120.4 . . ?
C48 C49 C50 120.4(5) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C49 C50 C45 120.5(5) . . ?
C49 C50 H50 119.7 . . ?
C45 C50 H50 119.7 . . ?
C1 N1 C8 108.5(5) . . ?
C1 N1 H1A 125.7 . . ?
C8 N1 H1A 125.7 . . ?
C18 N2 C11 125.2(5) . . ?
C18 N2 H2A 117.4 . . ?
C11 N2 H2A 117.4 . . ?
C26 N3 C28 108.8(5) . . ?
C26 N3 H3A 125.6 . . ?
C28 N3 H3A 125.6 . . ?
C38 N4 C34 123.7(5) . . ?
C38 N4 H4A 118.1 . . ?
C34 N4 H4A 118.1 . . ?
C9 O1 C25 114.4(5) . . ?
C36 O4 C37 115.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         1.570
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 971879'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 F3 N O4'
_chemical_formula_weight         275.18

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   '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                   14.395(3)
_cell_length_b                   10.661(2)
_cell_length_c                   15.136(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.588(3)
_cell_angle_gamma                90.00
_cell_volume                     2311.8(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    123
_cell_measurement_reflns_used    2999
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.10
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            12766
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.51
_reflns_number_total             5240
_reflns_number_gt                3541
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0662P)²+2.3829P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5240
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.78562(16) 0.6538(2) 0.82348(16) 0.0215(5) Uani 1 1 d . . .
H1 H 0.8040 0.5682 0.8258 0.026 Uiso 1 1 calc R . .
C2 C 0.69699(17) 0.6834(2) 0.83083(15) 0.0201(5) Uani 1 1 d . . .
C3 C 0.62622(16) 0.5865(2) 0.84701(16) 0.0198(5) Uani 1 1 d . . .
C4 C 0.65364(17) 0.4710(2) 0.88466(17) 0.0256(6) Uani 1 1 d . . .
H4 H 0.7180 0.4539 0.8996 0.031 Uiso 1 1 calc R . .
C5 C 0.58787(18) 0.3818(2) 0.90021(18) 0.0276(6) Uani 1 1 d . . .
H5 H 0.6070 0.3033 0.9256 0.033 Uiso 1 1 calc R . .
C6 C 0.49379(18) 0.4064(2) 0.87877(17) 0.0245(5) Uani 1 1 d . . .
C7 C 0.46555(17) 0.5206(2) 0.84122(18) 0.0259(6) Uani 1 1 d . . .
H7 H 0.4011 0.5371 0.8261 0.031 Uiso 1 1 calc R . .
C8 C 0.53157(17) 0.6104(2) 0.82580(17) 0.0237(5) Uani 1 1 d . . .
H8 H 0.5122 0.6888 0.8006 0.028 Uiso 1 1 calc R . .
C9 C 0.42295(19) 0.3082(3) 0.89418(19) 0.0302(6) Uani 1 1 d . . .
C10 C 0.66036(16) 0.8153(2) 0.81703(16) 0.0194(5) Uani 1 1 d . . .
C11 C 0.5938(2) 0.9876(2) 0.8834(2) 0.0372(7) Uani 1 1 d . . .
H11A H 0.6381 1.0494 0.8641 0.056 Uiso 1 1 calc R . .
H11B H 0.5737 1.0133 0.9407 0.056 Uiso 1 1 calc R . .
H11C H 0.5394 0.9826 0.8393 0.056 Uiso 1 1 calc R . .
C12 C 1.07705(17) 0.8602(2) 0.09421(16) 0.0233(5) Uani 1 1 d . . .
H12 H 1.0954 0.9432 0.1107 0.028 Uiso 1 1 calc R . .
C13 C 0.98661(16) 0.8322(2) 0.08591(15) 0.0200(5) Uani 1 1 d . . .
C14 C 0.91320(17) 0.9262(2) 0.09854(16) 0.0216(5) Uani 1 1 d . . .
C15 C 0.81953(18) 0.8925(3) 0.0880(2) 0.0354(7) Uani 1 1 d . . .
H15 H 0.8026 0.8087 0.0723 0.043 Uiso 1 1 calc R . .
C16 C 0.75058(19) 0.9793(3) 0.1001(2) 0.0389(7) Uani 1 1 d . . .
H16 H 0.6868 0.9551 0.0931 0.047 Uiso 1 1 calc R . .
C17 C 0.77492(18) 1.1017(2) 0.12259(18) 0.0267(6) Uani 1 1 d . . .
C18 C 0.86754(18) 1.1371(2) 0.13316(17) 0.0260(6) Uani 1 1 d . . .
H18 H 0.8840 1.2212 0.1486 0.031 Uiso 1 1 calc R . .
C19 C 0.93603(17) 1.0503(2) 0.12128(17) 0.0252(5) Uani 1 1 d . . .
H19 H 0.9997 1.0750 0.1286 0.030 Uiso 1 1 calc R . .
C20 C 0.70059(19) 1.1959(3) 0.1372(2) 0.0342(7) Uani 1 1 d . . .
C21 C 0.95116(16) 0.7020(2) 0.06253(16) 0.0209(5) Uani 1 1 d . . .
C22 C 0.9128(2) 0.5078(2) 0.1232(2) 0.0386(7) Uani 1 1 d . . .
H22A H 0.8515 0.5098 0.0888 0.058 Uiso 1 1 calc R . .
H22B H 0.9071 0.4690 0.1810 0.058 Uiso 1 1 calc R . .
H22C H 0.9563 0.4589 0.0910 0.058 Uiso 1 1 calc R . .
F1 F 0.45293(16) 0.2267(2) 0.95645(16) 0.0802(8) Uani 1 1 d . . .
F2 F 0.34591(16) 0.3536(2) 0.9197(2) 0.0970(11) Uani 1 1 d . . .
F3 F 0.40013(18) 0.2379(2) 0.82450(14) 0.0775(8) Uani 1 1 d . . .
F4 F 0.68099(17) 1.1997(3) 0.21972(15) 0.0801(8) Uani 1 1 d . . .
F5 F 0.72316(15) 1.31084(18) 0.11487(19) 0.0777(8) Uani 1 1 d . . .
F6 F 0.62037(13) 1.1727(2) 0.08878(16) 0.0664(7) Uani 1 1 d . . .
N1 N 1.14848(14) 0.7699(2) 0.07923(14) 0.0238(5) Uani 1 1 d . . .
N2 N 0.85469(14) 0.74969(19) 0.81206(14) 0.0238(5) Uani 1 1 d . . .
O1 O 0.92810(12) 0.71526(18) 0.78483(13) 0.0313(4) Uani 1 1 d . . .
O2 O 0.83736(13) 0.85954(17) 0.83024(14) 0.0332(5) Uani 1 1 d . . .
O3 O 0.64649(13) 0.86264(16) 0.74503(12) 0.0286(4) Uani 1 1 d . . .
O4 O 0.63868(13) 0.86567(16) 0.89249(12) 0.0293(4) Uani 1 1 d . . .
O5 O 1.12640(12) 0.66504(17) 0.05136(12) 0.0285(4) Uani 1 1 d . . .
O6 O 1.22958(12) 0.80613(19) 0.09455(14) 0.0356(5) Uani 1 1 d . . .
O7 O 0.92352(13) 0.66995(18) -0.01154(12) 0.0315(4) Uani 1 1 d . . .
O8 O 0.94780(12) 0.63502(15) 0.13596(12) 0.0246(4) 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
C1 C2 1.329(3) . ?
C1 N2 1.448(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.487(3) . ?
C2 C10 1.510(3) . ?
C3 C8 1.392(3) . ?
C3 C4 1.397(3) . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(4) . ?
C6 C9 1.495(4) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 F2 1.303(3) . ?
C9 F3 1.310(3) . ?
C9 F1 1.323(3) . ?
C10 O3 1.200(3) . ?
C10 O4 1.326(3) . ?
C11 O4 1.452(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.329(3) . ?
C12 N1 1.442(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.482(3) . ?
C13 C21 1.510(3) . ?
C14 C15 1.389(4) . ?
C14 C19 1.398(3) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 C20 1.499(4) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 F4 1.307(4) . ?
C20 F5 1.321(3) . ?
C20 F6 1.329(4) . ?
C21 O7 1.202(3) . ?
C21 O8 1.326(3) . ?
C22 O8 1.453(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 O5 1.226(3) . ?
N1 O6 1.230(3) . ?
N2 O1 1.227(3) . ?
N2 O2 1.234(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N2 121.3(2) . . ?
C2 C1 H1 119.4 . . ?
N2 C1 H1 119.4 . . ?
C1 C2 C3 121.9(2) . . ?
C1 C2 C10 122.3(2) . . ?
C3 C2 C10 115.7(2) . . ?
C8 C3 C4 119.1(2) . . ?
C8 C3 C2 120.4(2) . . ?
C4 C3 C2 120.5(2) . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 C9 119.7(2) . . ?
C7 C6 C9 120.1(2) . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C3 120.5(2) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
F2 C9 F3 107.3(3) . . ?
F2 C9 F1 105.1(3) . . ?
F3 C9 F1 103.7(3) . . ?
F2 C9 C6 113.5(2) . . ?
F3 C9 C6 113.4(2) . . ?
F1 C9 C6 113.0(2) . . ?
O3 C10 O4 125.4(2) . . ?
O3 C10 C2 122.8(2) . . ?
O4 C10 C2 111.5(2) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 122.8(2) . . ?
C13 C12 H12 118.6 . . ?
N1 C12 H12 118.6 . . ?
C12 C13 C14 122.7(2) . . ?
C12 C13 C21 122.3(2) . . ?
C14 C13 C21 115.0(2) . . ?
C15 C14 C19 118.3(2) . . ?
C15 C14 C13 120.5(2) . . ?
C19 C14 C13 121.2(2) . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.7(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 C20 119.7(2) . . ?
C16 C17 C20 120.0(2) . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
F4 C20 F5 107.3(3) . . ?
F4 C20 F6 106.0(2) . . ?
F5 C20 F6 104.6(3) . . ?
F4 C20 C17 112.7(3) . . ?
F5 C20 C17 112.7(2) . . ?
F6 C20 C17 112.9(2) . . ?
O7 C21 O8 126.4(2) . . ?
O7 C21 C13 123.6(2) . . ?
O8 C21 C13 109.7(2) . . ?
O8 C22 H22A 109.5 . . ?
O8 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O8 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 N1 O6 124.1(2) . . ?
O5 N1 C12 119.8(2) . . ?
O6 N1 C12 116.1(2) . . ?
O1 N2 O2 123.9(2) . . ?
O1 N2 C1 116.9(2) . . ?
O2 N2 C1 119.2(2) . . ?
C10 O4 C11 114.9(2) . . ?
C21 O8 C22 115.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 971880'
#######################################################################
#
#                 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_shelxla

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 N2 O2'
_chemical_formula_weight         382.45

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'P-42(1)c '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   21.2628(15)
_cell_length_b                   21.2628(15)
_cell_length_c                   9.0321(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4083.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    123
_cell_measurement_reflns_used    4436
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.64
_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            22780
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         27.43
_reflns_number_total             4629
_reflns_number_gt                3719
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0428P)²+0.5337P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(13)
_refine_ls_number_reflns         4629
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
C1 C 0.46854(8) 0.35447(9) -0.0073(2) 0.0191(4) Uani 1 1 d . . .
H1 H 0.4841 0.3946 0.0372 0.023 Uiso 1 1 calc R . .
C2 C 0.54012(8) 0.27848(9) 0.1117(2) 0.0216(4) Uani 1 1 d . . .
H2A H 0.5499 0.3101 0.1888 0.026 Uiso 1 1 calc R . .
H2B H 0.5788 0.2536 0.0940 0.026 Uiso 1 1 calc R . .
C3 C 0.48841(8) 0.23405(8) 0.17116(19) 0.0176(4) Uani 1 1 d . . .
C4 C 0.42747(8) 0.27134(8) 0.1742(2) 0.0164(4) Uani 1 1 d . . .
C5 C 0.36913(8) 0.26154(8) 0.2523(2) 0.0165(4) Uani 1 1 d . . .
C6 C 0.34551(9) 0.21514(9) 0.3478(2) 0.0219(4) Uani 1 1 d . . .
H6 H 0.3701 0.1792 0.3718 0.026 Uiso 1 1 calc R . .
C7 C 0.28592(9) 0.22246(10) 0.4066(2) 0.0284(5) Uani 1 1 d . . .
H7 H 0.2699 0.1915 0.4723 0.034 Uiso 1 1 calc R . .
C8 C 0.24891(9) 0.27451(10) 0.3713(2) 0.0313(5) Uani 1 1 d . . .
H8 H 0.2081 0.2782 0.4133 0.038 Uiso 1 1 calc R . .
C9 C 0.27041(9) 0.32081(10) 0.2766(2) 0.0272(5) Uani 1 1 d . . .
H9 H 0.2450 0.3560 0.2517 0.033 Uiso 1 1 calc R . .
C10 C 0.33090(9) 0.31397(9) 0.2187(2) 0.0191(4) Uani 1 1 d . . .
C11 C 0.42140(8) 0.32625(8) 0.0973(2) 0.0176(4) Uani 1 1 d . . .
C12 C 0.48082(8) 0.17857(8) 0.0646(2) 0.0203(4) Uani 1 1 d . . .
C13 C 0.43177(11) 0.08090(10) 0.0227(3) 0.0448(6) Uani 1 1 d . . .
H13A H 0.4243 0.0933 -0.0803 0.067 Uiso 1 1 calc R . .
H13B H 0.3960 0.0562 0.0589 0.067 Uiso 1 1 calc R . .
H13C H 0.4701 0.0555 0.0284 0.067 Uiso 1 1 calc R . .
C14 C 0.44024(8) 0.36948(8) -0.1568(2) 0.0199(4) Uani 1 1 d . . .
C15 C 0.39827(9) 0.32877(10) -0.2259(2) 0.0265(5) Uani 1 1 d . . .
H15 H 0.3873 0.2903 -0.1790 0.032 Uiso 1 1 calc R . .
C16 C 0.37219(10) 0.34361(11) -0.3623(2) 0.0358(5) Uani 1 1 d . . .
H16 H 0.3440 0.3151 -0.4089 0.043 Uiso 1 1 calc R . .
C17 C 0.38726(11) 0.39999(11) -0.4304(2) 0.0384(6) Uani 1 1 d . . .
H17 H 0.3690 0.4106 -0.5230 0.046 Uiso 1 1 calc R . .
C18 C 0.42876(11) 0.44040(11) -0.3635(2) 0.0364(6) Uani 1 1 d . . .
H18 H 0.4391 0.4791 -0.4100 0.044 Uiso 1 1 calc R . .
C19 C 0.45563(10) 0.42503(9) -0.2284(2) 0.0283(5) Uani 1 1 d . . .
H19 H 0.4850 0.4530 -0.1843 0.034 Uiso 1 1 calc R . .
C20 C 0.51016(8) 0.21038(8) 0.3221(2) 0.0183(4) Uani 1 1 d . . .
C21 C 0.49344(9) 0.24073(9) 0.4520(2) 0.0232(4) Uani 1 1 d . . .
H21 H 0.4668 0.2765 0.4480 0.028 Uiso 1 1 calc R . .
C22 C 0.51523(10) 0.21946(10) 0.5882(2) 0.0289(5) Uani 1 1 d . . .
H22 H 0.5024 0.2400 0.6767 0.035 Uiso 1 1 calc R . .
C23 C 0.55555(9) 0.16837(9) 0.5952(2) 0.0260(4) Uani 1 1 d . . .
H23 H 0.5705 0.1538 0.6882 0.031 Uiso 1 1 calc R . .
C24 C 0.57378(9) 0.13900(10) 0.4668(2) 0.0294(5) Uani 1 1 d . . .
H24 H 0.6019 0.1043 0.4709 0.035 Uiso 1 1 calc R . .
C25 C 0.55130(9) 0.15965(9) 0.3309(2) 0.0272(5) Uani 1 1 d . . .
H25 H 0.5642 0.1389 0.2429 0.033 Uiso 1 1 calc R . .
H1A H 0.3513(11) 0.3893(11) 0.092(3) 0.036(6) Uiso 1 1 d . . .
N1 N 0.36356(7) 0.35276(8) 0.12378(18) 0.0202(4) Uani 1 1 d . . .
N2 N 0.52328(7) 0.31174(7) -0.02657(17) 0.0203(3) Uani 1 1 d . . .
O1 O 0.50892(7) 0.17281(6) -0.05032(15) 0.0305(3) Uani 1 1 d . . .
O2 O 0.43908(6) 0.13690(6) 0.11359(17) 0.0312(3) 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
C1 N2 1.487(2) . ?
C1 C11 1.502(2) . ?
C1 C14 1.513(3) . ?
C1 H1 1.0000 . ?
C2 N2 1.479(2) . ?
C2 C3 1.546(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.519(2) . ?
C3 C20 1.525(2) . ?
C3 C12 1.531(3) . ?
C4 C11 1.365(2) . ?
C4 C5 1.442(3) . ?
C5 C6 1.404(3) . ?
C5 C10 1.412(3) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(3) . ?
C9 H9 0.9500 . ?
C10 N1 1.377(2) . ?
C11 N1 1.374(2) . ?
C12 O1 1.204(2) . ?
C12 O2 1.330(2) . ?
C13 O2 1.454(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.386(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.385(2) . ?
C20 C25 1.391(3) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N1 H1A 0.87(2) . ?

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
N2 C1 C11 110.61(15) . . ?
N2 C1 C14 109.60(15) . . ?
C11 C1 C14 112.35(15) . . ?
N2 C1 H1 108.0 . . ?
C11 C1 H1 108.0 . . ?
C14 C1 H1 108.0 . . ?
N2 C2 C3 114.40(15) . . ?
N2 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
N2 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C20 114.49(14) . . ?
C4 C3 C12 108.88(14) . . ?
C20 C3 C12 109.85(14) . . ?
C4 C3 C2 107.10(14) . . ?
C20 C3 C2 107.24(14) . . ?
C12 C3 C2 109.13(15) . . ?
C11 C4 C5 106.93(16) . . ?
C11 C4 C3 121.18(16) . . ?
C5 C4 C3 131.86(16) . . ?
C6 C5 C10 118.73(16) . . ?
C6 C5 C4 135.22(17) . . ?
C10 C5 C4 106.03(15) . . ?
C7 C6 C5 119.00(17) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 121.23(18) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 121.34(18) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 117.53(18) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
N1 C10 C9 129.43(18) . . ?
N1 C10 C5 108.42(15) . . ?
C9 C10 C5 122.15(17) . . ?
C4 C11 N1 110.29(16) . . ?
C4 C11 C1 126.78(16) . . ?
N1 C11 C1 122.89(16) . . ?
O1 C12 O2 123.37(18) . . ?
O1 C12 C3 124.61(17) . . ?
O2 C12 C3 112.02(16) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.23(18) . . ?
C19 C14 C1 120.16(17) . . ?
C15 C14 C1 121.60(17) . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.9(2) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C25 118.29(17) . . ?
C21 C20 C3 121.71(16) . . ?
C25 C20 C3 119.86(17) . . ?
C20 C21 C22 120.83(17) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 120.11(19) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.52(18) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.37(17) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 120.84(18) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
C11 N1 C10 108.30(15) . . ?
C11 N1 H1A 125.3(15) . . ?
C10 N1 H1A 126.3(15) . . ?
C2 N2 C1 112.49(14) . . ?
C12 O2 C13 115.42(17) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 982411'
