# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 918257'
#TrackingRef '1.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2 O4'
_chemical_formula_weight         386.39
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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   7.313(2)
_cell_length_b                   24.203(7)
_cell_length_c                   10.898(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.903(4)
_cell_angle_gamma                90.00
_cell_volume                     1845.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      25.00
_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7763
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3251
_reflns_number_gt                2831
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0562P)^2^+0.3234P] where P=(Fo^2^+2Fc^2^)/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         3251
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
N1 N 0.21629(16) 0.07064(5) 0.93916(11) 0.0389(3) Uani 1 1 d . . .
N2 N 0.29498(17) -0.09322(5) 0.81901(10) 0.0402(3) Uani 1 1 d . . .
C1 C 0.22321(19) 0.05654(6) 0.81841(12) 0.0370(3) Uani 1 1 d . . .
C2 C 0.20116(19) 0.09825(6) 0.71899(14) 0.0400(3) Uani 1 1 d . . .
C3 C 0.1672(2) 0.08359(6) 0.59070(14) 0.0471(4) Uani 1 1 d . . .
H3A H 0.1608 0.0465 0.5679 0.056 Uiso 1 1 calc R . .
C4 C 0.1431(3) 0.12359(7) 0.49720(16) 0.0579(4) Uani 1 1 d . . .
H4A H 0.1210 0.1136 0.4117 0.069 Uiso 1 1 calc R . .
C5 C 0.1519(3) 0.17847(7) 0.53201(18) 0.0649(5) Uani 1 1 d . . .
H5A H 0.1339 0.2057 0.4693 0.078 Uiso 1 1 calc R . .
C6 C 0.1872(2) 0.19352(7) 0.65880(18) 0.0602(5) Uani 1 1 d . . .
H6A H 0.1944 0.2308 0.6806 0.072 Uiso 1 1 calc R . .
C7 C 0.2122(2) 0.15395(6) 0.75453(15) 0.0469(4) Uani 1 1 d . . .
C8 C 0.2547(2) 0.16804(6) 0.89427(16) 0.0539(4) Uani 1 1 d . . .
H8A H 0.2047 0.2046 0.9021 0.065 Uiso 1 1 calc R . .
H8B H 0.3921 0.1692 0.9324 0.065 Uiso 1 1 calc R . .
C9 C 0.1705(2) 0.12749(6) 0.96802(16) 0.0516(4) Uani 1 1 d . . .
H9A H 0.2219 0.1344 1.0593 0.062 Uiso 1 1 calc R . .
H9B H 0.0329 0.1322 0.9447 0.062 Uiso 1 1 calc R . .
C11 C 0.24944(18) -0.00013(5) 0.82024(12) 0.0357(3) Uani 1 1 d . . .
C12 C 0.25855(18) -0.01981(6) 0.94190(12) 0.0361(3) Uani 1 1 d . . .
C13 C 0.23600(18) 0.02420(6) 1.01638(13) 0.0379(3) Uani 1 1 d . . .
C14 C 0.28755(19) -0.08007(6) 0.94440(12) 0.0380(3) Uani 1 1 d . . .
C15 C 0.2707(2) -0.04580(6) 0.73843(13) 0.0388(3) Uani 1 1 d . . .
C17 C 0.2337(2) 0.02508(6) 1.15112(13) 0.0434(3) Uani 1 1 d . . .
C18 C 0.2851(3) -0.03397(8) 1.33333(14) 0.0564(4) Uani 1 1 d . . .
H18A H 0.1698 -0.0214 1.3516 0.068 Uiso 1 1 calc R . .
H18B H 0.3935 -0.0142 1.3885 0.068 Uiso 1 1 calc R . .
C19 C 0.3099(3) -0.09500(8) 1.35460(16) 0.0624(5) Uani 1 1 d . . .
H19A H 0.3197 -0.1034 1.4424 0.094 Uiso 1 1 calc R . .
H19B H 0.4241 -0.1068 1.3357 0.094 Uiso 1 1 calc R . .
H19C H 0.2017 -0.1139 1.2994 0.094 Uiso 1 1 calc R . .
C21 C 0.3102(2) -0.14821(6) 0.77494(13) 0.0408(3) Uani 1 1 d . . .
C22 C 0.4220(2) -0.15835(6) 0.69435(15) 0.0493(4) Uani 1 1 d . . .
H22A H 0.4917 -0.1299 0.6721 0.059 Uiso 1 1 calc R . .
C23 C 0.4291(3) -0.21109(7) 0.64727(18) 0.0624(5) Uani 1 1 d . . .
H23A H 0.5002 -0.2177 0.5905 0.075 Uiso 1 1 calc R . .
C24 C 0.3323(3) -0.25393(7) 0.68335(19) 0.0668(5) Uani 1 1 d . . .
H24A H 0.3388 -0.2894 0.6520 0.080 Uiso 1 1 calc R . .
C25 C 0.2262(3) -0.24379(7) 0.76606(19) 0.0632(5) Uani 1 1 d . . .
H25A H 0.1634 -0.2728 0.7925 0.076 Uiso 1 1 calc R . .
C26 C 0.2113(2) -0.19108(6) 0.81057(16) 0.0531(4) Uani 1 1 d . . .
H26A H 0.1353 -0.1844 0.8642 0.064 Uiso 1 1 calc R . .
O1 O 0.30395(17) -0.11351(4) 1.02866(10) 0.0519(3) Uani 1 1 d . . .
O2 O 0.26778(18) -0.04688(4) 0.62723(9) 0.0548(3) Uani 1 1 d . . .
O3 O 0.1992(2) 0.06470(5) 1.20752(11) 0.0702(4) Uani 1 1 d . . .
O4 O 0.27200(19) -0.02467(5) 1.19976(10) 0.0605(3) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0382(6) 0.0361(6) 0.0425(6) -0.0064(5) 0.0120(5) -0.0032(5)
N2 0.0504(7) 0.0341(6) 0.0368(6) 0.0005(5) 0.0138(5) 0.0016(5)
C1 0.0344(7) 0.0384(7) 0.0375(7) -0.0019(5) 0.0094(5) -0.0028(5)
C2 0.0334(7) 0.0377(8) 0.0481(8) 0.0033(6) 0.0105(6) -0.0005(6)
C3 0.0497(8) 0.0442(8) 0.0460(8) 0.0046(6) 0.0118(6) -0.0024(7)
C4 0.0605(10) 0.0592(10) 0.0512(9) 0.0140(8) 0.0120(7) -0.0044(8)
C5 0.0692(11) 0.0550(10) 0.0663(11) 0.0228(8) 0.0131(9) -0.0006(9)
C6 0.0578(10) 0.0384(9) 0.0816(12) 0.0106(8) 0.0160(9) 0.0006(7)
C7 0.0382(8) 0.0395(8) 0.0616(9) 0.0028(7) 0.0126(7) 0.0010(6)
C8 0.0577(10) 0.0337(8) 0.0689(10) -0.0058(7) 0.0159(8) 0.0013(7)
C9 0.0556(9) 0.0430(8) 0.0574(9) -0.0099(7) 0.0185(7) 0.0024(7)
C11 0.0365(7) 0.0361(7) 0.0340(7) -0.0004(5) 0.0093(5) -0.0020(5)
C12 0.0335(7) 0.0404(7) 0.0337(7) -0.0008(5) 0.0087(5) -0.0030(6)
C13 0.0343(7) 0.0424(8) 0.0368(7) -0.0037(5) 0.0101(6) -0.0044(6)
C14 0.0368(7) 0.0411(8) 0.0360(7) 0.0021(6) 0.0105(5) -0.0006(6)
C15 0.0424(7) 0.0373(7) 0.0362(7) 0.0002(5) 0.0106(6) -0.0013(6)
C17 0.0407(8) 0.0510(9) 0.0386(7) -0.0103(6) 0.0116(6) -0.0103(6)
C18 0.0603(10) 0.0785(12) 0.0309(7) -0.0041(7) 0.0142(7) -0.0082(8)
C19 0.0630(11) 0.0797(13) 0.0459(9) 0.0096(8) 0.0181(8) 0.0082(9)
C21 0.0447(8) 0.0353(7) 0.0395(7) -0.0010(6) 0.0078(6) 0.0032(6)
C22 0.0537(9) 0.0445(8) 0.0517(8) 0.0008(7) 0.0183(7) 0.0037(7)
C23 0.0713(11) 0.0519(10) 0.0698(11) -0.0078(8) 0.0296(9) 0.0126(9)
C24 0.0736(12) 0.0420(9) 0.0827(13) -0.0130(8) 0.0194(10) 0.0056(8)
C25 0.0685(11) 0.0396(9) 0.0831(12) -0.0019(8) 0.0245(10) -0.0066(8)
C26 0.0589(10) 0.0432(9) 0.0608(9) -0.0028(7) 0.0231(8) -0.0029(7)
O1 0.0692(7) 0.0467(6) 0.0417(5) 0.0090(5) 0.0191(5) 0.0052(5)
O2 0.0854(8) 0.0463(6) 0.0352(6) 0.0007(4) 0.0215(5) 0.0048(5)
O3 0.1059(11) 0.0598(8) 0.0526(7) -0.0176(6) 0.0352(7) -0.0089(7)
O4 0.0870(9) 0.0619(7) 0.0367(6) 0.0023(5) 0.0243(6) 0.0096(6)
_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
N1 C1 1.3746(18) . ?
N1 C13 1.3864(18) . ?
N1 C9 1.4715(19) . ?
N2 C14 1.4194(18) . ?
N2 C15 1.4245(18) . ?
N2 C21 1.4301(18) . ?
C1 C11 1.384(2) . ?
C1 C2 1.4550(19) . ?
C2 C3 1.393(2) . ?
C2 C7 1.399(2) . ?
C3 C4 1.379(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.389(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.502(2) . ?
C8 C9 1.509(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.3920(18) . ?
C11 C15 1.4565(19) . ?
C12 C13 1.3778(19) . ?
C12 C14 1.473(2) . ?
C13 C17 1.473(2) . ?
C14 O1 1.2035(17) . ?
C15 O2 1.2061(17) . ?
C17 O3 1.2045(18) . ?
C17 O4 1.3126(19) . ?
C18 O4 1.4483(18) . ?
C18 C19 1.498(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C26 1.383(2) . ?
C21 C22 1.385(2) . ?
C22 C23 1.382(2) . ?
C22 H22A 0.9300 . ?
C23 C24 1.376(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.372(3) . ?
C24 H24A 0.9300 . ?
C25 C26 1.380(2) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 110.70(11) . . ?
C1 N1 C9 120.72(12) . . ?
C13 N1 C9 128.19(12) . . ?
C14 N2 C15 112.33(11) . . ?
C14 N2 C21 124.09(11) . . ?
C15 N2 C21 123.42(11) . . ?
N1 C1 C11 106.00(11) . . ?
N1 C1 C2 120.91(12) . . ?
C11 C1 C2 133.08(12) . . ?
C3 C2 C7 120.17(13) . . ?
C3 C2 C1 121.30(13) . . ?
C7 C2 C1 118.52(13) . . ?
C4 C3 C2 120.67(15) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C5 C4 C3 119.18(16) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 120.72(15) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C7 121.07(16) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C6 C7 C2 118.19(15) . . ?
C6 C7 C8 123.25(14) . . ?
C2 C7 C8 118.55(13) . . ?
C7 C8 C9 113.33(13) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
N1 C9 C8 109.93(12) . . ?
N1 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C1 C11 C12 108.72(11) . . ?
C1 C11 C15 141.45(12) . . ?
C12 C11 C15 109.83(12) . . ?
C13 C12 C11 108.41(12) . . ?
C13 C12 C14 142.73(12) . . ?
C11 C12 C14 108.86(11) . . ?
C12 C13 N1 106.16(12) . . ?
C12 C13 C17 129.52(13) . . ?
N1 C13 C17 124.32(12) . . ?
O1 C14 N2 124.09(13) . . ?
O1 C14 C12 131.44(13) . . ?
N2 C14 C12 104.47(11) . . ?
O2 C15 N2 124.37(13) . . ?
O2 C15 C11 131.11(13) . . ?
N2 C15 C11 104.51(11) . . ?
O3 C17 O4 125.17(14) . . ?
O3 C17 C13 125.79(15) . . ?
O4 C17 C13 109.03(12) . . ?
O4 C18 C19 106.17(13) . . ?
O4 C18 H18A 110.5 . . ?
C19 C18 H18A 110.5 . . ?
O4 C18 H18B 110.5 . . ?
C19 C18 H18B 110.5 . . ?
H18A C18 H18B 108.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C21 C22 119.90(14) . . ?
C26 C21 N2 120.39(13) . . ?
C22 C21 N2 119.71(13) . . ?
C23 C22 C21 119.47(15) . . ?
C23 C22 H22A 120.3 . . ?
C21 C22 H22A 120.3 . . ?
C24 C23 C22 120.78(17) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C25 C24 C23 119.30(16) . . ?
C25 C24 H24A 120.4 . . ?
C23 C24 H24A 120.4 . . ?
C24 C25 C26 120.91(16) . . ?
C24 C25 H25A 119.5 . . ?
C26 C25 H25A 119.5 . . ?
C25 C26 C21 119.58(16) . . ?
C25 C26 H26A 120.2 . . ?
C21 C26 H26A 120.2 . . ?
C17 O4 C18 119.50(12) . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.064


data_zcs1
_database_code_depnum_ccdc_archive 'CCDC 918258'
#TrackingRef 'zcs1.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 Br N2 O4'
_chemical_formula_weight         463.28
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)/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                   7.854(3)
_cell_length_b                   20.136(8)
_cell_length_c                   12.952(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.591(7)
_cell_angle_gamma                90.00
_cell_volume                     1963.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3085
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      31.04
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_T_max  0.682
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13520
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         31.04
_reflns_number_total             6085
_reflns_number_gt                3731
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0718P)^2^+0.8018P] where P=(Fo^2^+2Fc^2^)/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         6085
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.003
_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 0.1773(4) 1.30796(13) -0.0592(2) 0.0460(6) Uani 1 1 d . . .
C2 C 0.2456(4) 1.28337(13) 0.0428(2) 0.0485(6) Uani 1 1 d . . .
H2A H 0.2753 1.3120 0.1017 0.058 Uiso 1 1 calc R . .
C3 C 0.2701(4) 1.21569(13) 0.0576(2) 0.0441(6) Uani 1 1 d . . .
H3A H 0.3180 1.1986 0.1265 0.053 Uiso 1 1 calc R . .
C4 C 0.2233(3) 1.17317(11) -0.0301(2) 0.0357(5) Uani 1 1 d . . .
C5 C 0.1555(3) 1.19905(12) -0.1327(2) 0.0398(5) Uani 1 1 d . . .
H5A H 0.1250 1.1707 -0.1919 0.048 Uiso 1 1 calc R . .
C6 C 0.1330(4) 1.26699(13) -0.1475(2) 0.0456(6) Uani 1 1 d . . .
H6A H 0.0883 1.2846 -0.2163 0.055 Uiso 1 1 calc R . .
C7 C 0.2889(3) 1.05918(11) -0.08804(19) 0.0336(5) Uani 1 1 d . . .
C8 C 0.2754(3) 0.99302(11) -0.04387(18) 0.0323(4) Uani 1 1 d . . .
C9 C 0.2287(3) 0.99938(11) 0.05135(18) 0.0324(4) Uani 1 1 d . . .
C10 C 0.1987(3) 1.06920(12) 0.07037(19) 0.0354(5) Uani 1 1 d . . .
C11 C 0.2282(3) 0.93648(11) 0.09563(18) 0.0323(4) Uani 1 1 d . . .
C12 C 0.2020(3) 0.91254(11) 0.19568(19) 0.0336(5) Uani 1 1 d . . .
C13 C 0.1158(3) 0.95134(12) 0.25487(19) 0.0383(5) Uani 1 1 d . . .
H13A H 0.0742 0.9935 0.2308 0.046 Uiso 1 1 calc R . .
C14 C 0.0931(4) 0.92682(15) 0.3486(2) 0.0487(6) Uani 1 1 d . . .
H14A H 0.0337 0.9521 0.3875 0.058 Uiso 1 1 calc R . .
C15 C 0.1577(4) 0.86479(15) 0.3858(2) 0.0516(7) Uani 1 1 d . . .
H15A H 0.1425 0.8488 0.4500 0.062 Uiso 1 1 calc R . .
C16 C 0.2443(4) 0.82667(14) 0.3288(2) 0.0482(6) Uani 1 1 d . . .
H16A H 0.2885 0.7852 0.3549 0.058 Uiso 1 1 calc R . .
C17 C 0.2663(3) 0.84967(12) 0.2320(2) 0.0388(5) Uani 1 1 d . . .
C18 C 0.3580(4) 0.80902(13) 0.1664(2) 0.0465(6) Uani 1 1 d . . .
H18 H 0.4513 0.7800 0.1958 0.056 Uiso 1 1 calc R . .
C19 C 0.2805(4) 0.82100(12) 0.0472(2) 0.0450(6) Uani 1 1 d . . .
H19 H 0.2444 0.7880 -0.0047 0.054 Uiso 1 1 calc R . .
C20 C 0.2980(3) 0.92623(11) -0.06144(18) 0.0325(4) Uani 1 1 d . . .
C21 C 0.3303(3) 0.89298(12) -0.1544(2) 0.0389(5) Uani 1 1 d . . .
C22 C 0.4063(5) 0.91266(18) -0.3150(2) 0.0621(8) Uani 1 1 d . . .
H22A H 0.3088 0.8841 -0.3525 0.075 Uiso 1 1 calc R . .
H22B H 0.5161 0.8876 -0.3008 0.075 Uiso 1 1 calc R . .
C23 C 0.4145(5) 0.9719(2) -0.3807(3) 0.0749(10) Uani 1 1 d . . .
H23A H 0.4329 0.9583 -0.4477 0.112 Uiso 1 1 calc R . .
H23B H 0.5110 0.9998 -0.3424 0.112 Uiso 1 1 calc R . .
H23C H 0.3049 0.9961 -0.3946 0.112 Uiso 1 1 calc R . .
N1 N 0.2415(3) 1.10337(9) -0.01505(16) 0.0359(4) Uani 1 1 d . . .
N2 N 0.2707(3) 0.89293(9) 0.02551(16) 0.0334(4) Uani 1 1 d . . .
O1 O 0.1464(3) 1.09551(9) 0.13877(15) 0.0469(4) Uani 1 1 d . . .
O2 O 0.3332(2) 1.07690(9) -0.16495(15) 0.0436(4) Uani 1 1 d . . .
O3 O 0.3800(3) 0.93614(10) -0.21553(15) 0.0564(5) Uani 1 1 d . . .
O4 O 0.3143(4) 0.83432(10) -0.17320(17) 0.0646(6) Uani 1 1 d . . .
Br1 Br 0.14133(6) 1.400515(14) -0.08008(3) 0.07081(16) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0580(16) 0.0286(12) 0.0546(16) 0.0035(11) 0.0212(13) 0.0002(11)
C2 0.0641(17) 0.0311(12) 0.0482(15) -0.0045(11) 0.0125(13) -0.0019(12)
C3 0.0543(15) 0.0354(13) 0.0374(13) 0.0002(10) 0.0046(11) 0.0016(11)
C4 0.0365(12) 0.0277(11) 0.0413(13) 0.0040(9) 0.0085(10) -0.0003(9)
C5 0.0476(14) 0.0320(11) 0.0378(12) 0.0007(10) 0.0091(10) -0.0026(10)
C6 0.0602(16) 0.0327(12) 0.0428(14) 0.0071(10) 0.0128(12) 0.0014(11)
C7 0.0327(11) 0.0308(11) 0.0345(11) -0.0004(9) 0.0050(9) -0.0006(9)
C8 0.0319(11) 0.0300(10) 0.0327(11) 0.0005(9) 0.0054(9) -0.0010(9)
C9 0.0325(11) 0.0294(10) 0.0337(11) 0.0011(9) 0.0068(9) 0.0000(9)
C10 0.0386(12) 0.0309(11) 0.0354(12) 0.0010(9) 0.0085(9) -0.0008(9)
C11 0.0325(11) 0.0281(10) 0.0338(11) -0.0004(9) 0.0052(9) -0.0001(8)
C12 0.0354(11) 0.0296(10) 0.0330(11) 0.0002(9) 0.0052(9) -0.0042(9)
C13 0.0457(13) 0.0318(11) 0.0360(12) -0.0032(9) 0.0091(10) -0.0040(10)
C14 0.0645(17) 0.0458(15) 0.0367(13) -0.0062(11) 0.0156(12) -0.0053(13)
C15 0.0770(19) 0.0451(15) 0.0325(13) 0.0019(11) 0.0152(13) -0.0076(14)
C16 0.0630(17) 0.0374(13) 0.0404(14) 0.0095(11) 0.0083(12) -0.0015(12)
C17 0.0437(13) 0.0318(11) 0.0381(12) 0.0034(9) 0.0072(10) -0.0022(10)
C18 0.0537(15) 0.0333(13) 0.0535(15) 0.0106(11) 0.0172(12) 0.0120(11)
C19 0.0638(16) 0.0256(11) 0.0467(14) -0.0012(10) 0.0173(12) -0.0014(11)
C20 0.0331(11) 0.0297(10) 0.0340(11) -0.0015(9) 0.0085(9) -0.0019(9)
C21 0.0435(13) 0.0338(12) 0.0377(12) -0.0026(10) 0.0088(10) 0.0005(10)
C22 0.082(2) 0.066(2) 0.0424(16) -0.0031(14) 0.0260(15) -0.0009(17)
C23 0.093(3) 0.086(3) 0.0500(18) 0.0061(17) 0.0268(18) -0.014(2)
N1 0.0445(11) 0.0258(9) 0.0369(10) 0.0030(8) 0.0107(9) 0.0007(8)
N2 0.0370(10) 0.0267(9) 0.0348(10) 0.0003(7) 0.0075(8) -0.0014(7)
O1 0.0661(12) 0.0339(9) 0.0462(10) -0.0019(7) 0.0249(9) 0.0030(8)
O2 0.0530(10) 0.0375(9) 0.0438(10) 0.0041(8) 0.0196(8) -0.0007(8)
O3 0.0879(15) 0.0454(11) 0.0434(10) -0.0076(9) 0.0309(10) -0.0129(10)
O4 0.1137(19) 0.0342(10) 0.0532(12) -0.0083(9) 0.0357(12) -0.0030(11)
Br1 0.1186(4) 0.02848(16) 0.0741(3) 0.00725(13) 0.0416(2) 0.00638(15)
_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 1.369(4) . ?
C1 C6 1.371(4) . ?
C1 Br1 1.893(3) . ?
C2 C3 1.382(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(3) . ?
C4 N1 1.421(3) . ?
C5 C6 1.386(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 O2 1.200(3) . ?
C7 N1 1.423(3) . ?
C7 C8 1.465(3) . ?
C8 C20 1.384(3) . ?
C8 C9 1.389(3) . ?
C9 C11 1.391(3) . ?
C9 C10 1.458(3) . ?
C10 O1 1.201(3) . ?
C10 N1 1.422(3) . ?
C11 N2 1.370(3) . ?
C11 C12 1.451(3) . ?
C12 C17 1.394(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.368(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.382(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.393(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.503(4) . ?
C18 C19 1.509(4) . ?
C18 H18 0.9300 . ?
C19 N2 1.473(3) . ?
C19 H19 0.9300 . ?
C20 N2 1.379(3) . ?
C20 C21 1.462(3) . ?
C21 O4 1.205(3) . ?
C21 O3 1.308(3) . ?
C22 O3 1.442(4) . ?
C22 C23 1.477(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C2 C1 C6 121.6(2) . . ?
C2 C1 Br1 119.7(2) . . ?
C6 C1 Br1 118.8(2) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 N1 120.0(2) . . ?
C3 C4 N1 120.4(2) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
O2 C7 N1 124.0(2) . . ?
O2 C7 C8 131.7(2) . . ?
N1 C7 C8 104.32(19) . . ?
C20 C8 C9 108.3(2) . . ?
C20 C8 C7 142.4(2) . . ?
C9 C8 C7 109.2(2) . . ?
C8 C9 C11 108.3(2) . . ?
C8 C9 C10 109.6(2) . . ?
C11 C9 C10 142.1(2) . . ?
O1 C10 N1 124.6(2) . . ?
O1 C10 C9 131.0(2) . . ?
N1 C10 C9 104.45(19) . . ?
N2 C11 C9 106.2(2) . . ?
N2 C11 C12 120.2(2) . . ?
C9 C11 C12 133.5(2) . . ?
C17 C12 C13 120.6(2) . . ?
C17 C12 C11 118.2(2) . . ?
C13 C12 C11 121.2(2) . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C16 C17 C12 118.6(2) . . ?
C16 C17 C18 122.0(2) . . ?
C12 C17 C18 119.4(2) . . ?
C17 C18 C19 111.9(2) . . ?
C17 C18 H18 124.1 . . ?
C19 C18 H18 124.1 . . ?
N2 C19 C18 109.6(2) . . ?
N2 C19 H19 125.2 . . ?
C18 C19 H19 125.2 . . ?
N2 C20 C8 106.34(19) . . ?
N2 C20 C21 123.6(2) . . ?
C8 C20 C21 129.9(2) . . ?
O4 C21 O3 124.1(2) . . ?
O4 C21 C20 125.7(2) . . ?
O3 C21 C20 110.3(2) . . ?
O3 C22 C23 106.9(3) . . ?
O3 C22 H22A 110.3 . . ?
C23 C22 H22A 110.3 . . ?
O3 C22 H22B 110.3 . . ?
C23 C22 H22B 110.3 . . ?
H22A C22 H22B 108.6 . . ?
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 . . ?
C4 N1 C10 123.3(2) . . ?
C4 N1 C7 124.2(2) . . ?
C10 N1 C7 112.28(18) . . ?
C11 N2 C20 110.74(19) . . ?
C11 N2 C19 120.8(2) . . ?
C20 N2 C19 128.5(2) . . ?
C21 O3 C22 117.8(2) . . ?
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        31.04
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.091