# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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# 
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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_2301
_database_code_depnum_ccdc_archive 'CCDC 895782'
#TrackingRef 'web_deposit_cif_file_0_xinfangxu_1344745384.2301.cif'


_audit_creation_method           'SHELXL-97 & ZCIF'
_chemical_name_systematic        
;
Xu XXU-NOH-Br
;
_chemical_name_common            'Xu XXU-NOH-Br'
_chemical_formula_moiety         'C18 H14 Br N O2'
_chemical_formula_sum            'C18 H14 Br N O2'
_chemical_formula_weight         356.21

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.0327(5)
_cell_length_b                   9.2545(7)
_cell_length_c                   12.4679(9)
_cell_angle_alpha                82.8208(11)
_cell_angle_beta                 77.3755(11)
_cell_angle_gamma                73.6561(12)
_cell_volume                     758.10(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7430
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      30.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    2.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.432
_exptl_absorpt_correction_T_max  0.762
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_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  'three-circle diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10646
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3467
_reflns_number_gt                3246
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_cell_refinement       Apex2
_computing_data_reduction        Apex2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  SHELXL-97

_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     
'w=1/[\s^2^(Fo^2^)+(0.01P)^2^+1.074P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refAll
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3467
_refine_ls_number_parameters     253
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.993
_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 0.32573(4) 0.32645(3) -0.142779(18) 0.04242(8) Uani 1 1 d . . .
C1 C 0.3264(3) 0.3519(2) 0.00581(16) 0.0289(4) Uani 1 1 d . . .
C2 C 0.2310(3) 0.4914(2) 0.04849(17) 0.0313(4) Uani 1 1 d D . .
H2 H 0.166(3) 0.5735(19) 0.0052(17) 0.035(6) Uiso 1 1 d D . .
C3 C 0.2297(3) 0.5082(2) 0.15807(16) 0.0282(4) Uani 1 1 d D . .
H3 H 0.165(3) 0.6021(17) 0.189(2) 0.043(7) Uiso 1 1 d D . .
C4 C 0.3235(3) 0.3873(2) 0.22342(15) 0.0234(4) Uani 1 1 d . . .
C5 C 0.4199(3) 0.2487(2) 0.17791(16) 0.0272(4) Uani 1 1 d D . .
H5 H 0.484(3) 0.1663(19) 0.2212(17) 0.035(6) Uiso 1 1 d D . .
C6 C 0.4211(3) 0.2309(2) 0.06899(17) 0.0294(4) Uani 1 1 d D . .
H6 H 0.483(3) 0.1358(16) 0.0403(19) 0.041(7) Uiso 1 1 d D . .
C7 C 0.3160(3) 0.4065(2) 0.33884(15) 0.0229(4) Uani 1 1 d . . .
N7 N 0.2410(2) 0.52839(17) 0.39157(13) 0.0233(3) Uani 1 1 d . . .
C8 C 0.2656(3) 0.4831(2) 0.50044(15) 0.0231(4) Uani 1 1 d . . .
C9 C 0.3581(3) 0.3335(2) 0.50525(15) 0.0246(4) Uani 1 1 d . . .
O10 O 0.4252(2) 0.23674(16) 0.58614(12) 0.0304(3) Uani 1 1 d . . .
C10 C 0.3166(5) 0.1246(3) 0.6241(2) 0.0487(7) Uani 1 1 d D . .
H10A H 0.177(3) 0.173(3) 0.643(3) 0.068(6) Uiso 1 1 d D . .
H10B H 0.364(5) 0.073(3) 0.6876(19) 0.068(6) Uiso 1 1 d D . .
H10C H 0.330(5) 0.063(3) 0.567(2) 0.068(6) Uiso 1 1 d D . .
O11 O 0.39291(19) 0.28031(14) 0.40258(11) 0.0245(3) Uani 1 1 d . . .
C11 C 0.2005(3) 0.5826(2) 0.58966(15) 0.0249(4) Uani 1 1 d D . .
H11 H 0.237(3) 0.536(2) 0.6569(12) 0.030(6) Uiso 1 1 d D . .
C12 C 0.0955(3) 0.7267(2) 0.58072(15) 0.0243(4) Uani 1 1 d D . .
H12 H 0.063(3) 0.765(2) 0.5111(11) 0.033(6) Uiso 1 1 d D . .
C13 C 0.0248(3) 0.8326(2) 0.66821(15) 0.0240(4) Uani 1 1 d . . .
C14 C -0.1124(3) 0.9717(2) 0.65123(16) 0.0268(4) Uani 1 1 d D . .
H14 H -0.157(3) 0.998(2) 0.5833(12) 0.028(6) Uiso 1 1 d D . .
C15 C -0.1837(3) 1.0762(2) 0.73128(17) 0.0311(4) Uani 1 1 d D . .
H15 H -0.272(3) 1.1707(16) 0.7156(19) 0.035(6) Uiso 1 1 d D . .
C16 C -0.1195(3) 1.0431(2) 0.83161(18) 0.0336(4) Uani 1 1 d D . .
H16 H -0.161(3) 1.1096(19) 0.8877(13) 0.021(5) Uiso 1 1 d D . .
C17 C 0.0167(3) 0.9049(3) 0.85005(17) 0.0343(5) Uani 1 1 d D . .
H17 H 0.061(4) 0.881(3) 0.9179(13) 0.042(7) Uiso 1 1 d D . .
C18 C 0.0887(3) 0.8006(2) 0.76999(17) 0.0296(4) Uani 1 1 d D . .
H18 H 0.181(3) 0.7077(16) 0.7837(19) 0.033(6) Uiso 1 1 d 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
Br1 0.04116(13) 0.05498(15) 0.02597(11) -0.01356(9) -0.00942(9) 0.00255(10)
C1 0.0261(9) 0.0387(11) 0.0221(9) -0.0073(8) -0.0036(7) -0.0073(8)
C2 0.0334(10) 0.0310(10) 0.0270(10) -0.0017(8) -0.0091(8) -0.0018(8)
C3 0.0311(10) 0.0246(9) 0.0273(10) -0.0039(7) -0.0060(8) -0.0037(8)
C4 0.0213(8) 0.0263(9) 0.0235(9) -0.0034(7) -0.0033(7) -0.0077(7)
C5 0.0266(9) 0.0255(9) 0.0276(10) -0.0021(7) -0.0051(7) -0.0037(7)
C6 0.0275(10) 0.0281(10) 0.0308(10) -0.0090(8) -0.0027(8) -0.0038(8)
C7 0.0211(8) 0.0225(9) 0.0253(9) 0.0006(7) -0.0052(7) -0.0063(7)
N7 0.0235(7) 0.0244(8) 0.0230(7) -0.0023(6) -0.0045(6) -0.0077(6)
C8 0.0223(8) 0.0266(9) 0.0221(9) -0.0006(7) -0.0049(7) -0.0093(7)
C9 0.0248(9) 0.0275(9) 0.0239(9) -0.0017(7) -0.0078(7) -0.0085(7)
O10 0.0352(7) 0.0283(7) 0.0308(7) 0.0052(6) -0.0153(6) -0.0097(6)
C10 0.0717(18) 0.0503(15) 0.0383(13) 0.0181(11) -0.0250(13) -0.0368(14)
O11 0.0262(6) 0.0232(6) 0.0246(6) -0.0017(5) -0.0073(5) -0.0053(5)
C11 0.0263(9) 0.0280(9) 0.0224(9) -0.0018(7) -0.0058(7) -0.0095(7)
C12 0.0235(9) 0.0300(10) 0.0213(9) -0.0028(7) -0.0049(7) -0.0089(7)
C13 0.0217(8) 0.0277(9) 0.0238(9) -0.0033(7) -0.0030(7) -0.0087(7)
C14 0.0264(9) 0.0291(10) 0.0248(9) -0.0009(7) -0.0043(7) -0.0080(8)
C15 0.0289(10) 0.0278(10) 0.0336(11) -0.0042(8) -0.0021(8) -0.0049(8)
C16 0.0346(11) 0.0335(11) 0.0320(11) -0.0095(9) -0.0008(8) -0.0086(9)
C17 0.0384(11) 0.0402(12) 0.0260(10) -0.0072(9) -0.0096(9) -0.0081(9)
C18 0.0287(10) 0.0317(10) 0.0277(10) -0.0042(8) -0.0088(8) -0.0033(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.8977(19) . ?
C1 C6 1.381(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.392(3) . ?
C2 H2 0.943(10) . ?
C3 C4 1.393(3) . ?
C3 H3 0.946(10) . ?
C4 C5 1.397(3) . ?
C4 C7 1.460(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.942(10) . ?
C6 H6 0.942(10) . ?
C7 N7 1.297(2) . ?
C7 O11 1.374(2) . ?
N7 C8 1.403(2) . ?
C8 C9 1.354(3) . ?
C8 C11 1.446(3) . ?
C9 O10 1.336(2) . ?
C9 O11 1.376(2) . ?
O10 C10 1.431(3) . ?
C10 H10A 0.947(17) . ?
C10 H10B 0.946(17) . ?
C10 H10C 0.946(17) . ?
C11 C12 1.335(3) . ?
C11 H11 0.945(10) . ?
C12 C13 1.468(3) . ?
C12 H12 0.945(10) . ?
C13 C14 1.398(3) . ?
C13 C18 1.407(3) . ?
C14 C15 1.390(3) . ?
C14 H14 0.947(10) . ?
C15 C16 1.391(3) . ?
C15 H15 0.946(10) . ?
C16 C17 1.393(3) . ?
C16 H16 0.933(10) . ?
C17 C18 1.389(3) . ?
C17 H17 0.944(10) . ?
C18 H18 0.944(10) . ?

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
C6 C1 C2 121.62(18) . . ?
C6 C1 Br1 119.14(15) . . ?
C2 C1 Br1 119.24(15) . . ?
C1 C2 C3 118.78(19) . . ?
C1 C2 H2 121.3(15) . . ?
C3 C2 H2 119.9(15) . . ?
C2 C3 C4 120.51(18) . . ?
C2 C3 H3 120.2(16) . . ?
C4 C3 H3 119.3(16) . . ?
C3 C4 C5 119.42(17) . . ?
C3 C4 C7 119.57(17) . . ?
C5 C4 C7 121.00(17) . . ?
C6 C5 C4 120.39(18) . . ?
C6 C5 H5 119.4(15) . . ?
C4 C5 H5 120.2(15) . . ?
C1 C6 C5 119.28(18) . . ?
C1 C6 H6 121.4(16) . . ?
C5 C6 H6 119.3(16) . . ?
N7 C7 O11 114.28(16) . . ?
N7 C7 C4 128.37(17) . . ?
O11 C7 C4 117.34(16) . . ?
C7 N7 C8 105.01(15) . . ?
C9 C8 N7 108.00(16) . . ?
C9 C8 C11 127.52(17) . . ?
N7 C8 C11 124.48(17) . . ?
O10 C9 C8 132.72(18) . . ?
O10 C9 O11 117.85(16) . . ?
C8 C9 O11 109.35(16) . . ?
C9 O10 C10 114.66(16) . . ?
O10 C10 H10A 109(2) . . ?
O10 C10 H10B 106.9(19) . . ?
H10A C10 H10B 110(3) . . ?
O10 C10 H10C 110(2) . . ?
H10A C10 H10C 106(3) . . ?
H10B C10 H10C 115(3) . . ?
C7 O11 C9 103.35(14) . . ?
C12 C11 C8 124.15(18) . . ?
C12 C11 H11 121.8(14) . . ?
C8 C11 H11 114.1(14) . . ?
C11 C12 C13 126.59(18) . . ?
C11 C12 H12 117.1(14) . . ?
C13 C12 H12 116.3(14) . . ?
C14 C13 C18 117.77(17) . . ?
C14 C13 C12 119.41(17) . . ?
C18 C13 C12 122.82(17) . . ?
C15 C14 C13 121.69(18) . . ?
C15 C14 H14 118.1(14) . . ?
C13 C14 H14 120.2(14) . . ?
C14 C15 C16 119.96(19) . . ?
C14 C15 H15 119.2(15) . . ?
C16 C15 H15 120.8(15) . . ?
C15 C16 C17 119.12(19) . . ?
C15 C16 H16 123.5(13) . . ?
C17 C16 H16 117.3(13) . . ?
C18 C17 C16 120.98(19) . . ?
C18 C17 H17 118.9(16) . . ?
C16 C17 H17 120.1(16) . . ?
C17 C18 C13 120.47(19) . . ?
C17 C18 H18 119.9(14) . . ?
C13 C18 H18 119.6(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(3) . . . . ?
Br1 C1 C2 C3 179.04(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C3 C4 C7 -178.48(18) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C7 C4 C5 C6 178.21(18) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
Br1 C1 C6 C5 -179.29(15) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C3 C4 C7 N7 -4.6(3) . . . . ?
C5 C4 C7 N7 176.62(19) . . . . ?
C3 C4 C7 O11 173.66(17) . . . . ?
C5 C4 C7 O11 -5.1(3) . . . . ?
O11 C7 N7 C8 -0.7(2) . . . . ?
C4 C7 N7 C8 177.64(18) . . . . ?
C7 N7 C8 C9 0.7(2) . . . . ?
C7 N7 C8 C11 -179.09(17) . . . . ?
N7 C8 C9 O10 176.17(19) . . . . ?
C11 C8 C9 O10 -4.1(3) . . . . ?
N7 C8 C9 O11 -0.4(2) . . . . ?
C11 C8 C9 O11 179.35(17) . . . . ?
C8 C9 O10 C10 112.5(3) . . . . ?
O11 C9 O10 C10 -71.2(2) . . . . ?
N7 C7 O11 C9 0.5(2) . . . . ?
C4 C7 O11 C9 -178.07(16) . . . . ?
O10 C9 O11 C7 -177.17(16) . . . . ?
C8 C9 O11 C7 -0.01(19) . . . . ?
C9 C8 C11 C12 -174.36(19) . . . . ?
N7 C8 C11 C12 5.4(3) . . . . ?
C8 C11 C12 C13 179.73(17) . . . . ?
C11 C12 C13 C14 -169.09(19) . . . . ?
C11 C12 C13 C18 10.8(3) . . . . ?
C18 C13 C14 C15 0.3(3) . . . . ?
C12 C13 C14 C15 -179.83(18) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C14 C13 C18 C17 -0.1(3) . . . . ?
C12 C13 C18 C17 -179.92(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.240
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.056

_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0893684
_diffrn_orient_matrix_UB_12      0.0663216
_diffrn_orient_matrix_UB_13      0.0019759
_diffrn_orient_matrix_UB_21      -0.0560618
_diffrn_orient_matrix_UB_22      0.0107225
_diffrn_orient_matrix_UB_23      0.0803906
_diffrn_orient_matrix_UB_31      0.1080460
_diffrn_orient_matrix_UB_32      -0.0906916
_diffrn_orient_matrix_UB_33      0.0178988
_symmetry_space_group_name_Hall  '-P 1'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker Smart Apex II'
_diffrn_standards_decay_%        0

#_______________________________________________________________________________
#


data_2280prelim1
_database_code_depnum_ccdc_archive 'CCDC 895783'
#TrackingRef 'web_deposit_cif_file_1_xinfangxu_1344745384.2280prelim1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cl N O4'
_chemical_formula_weight         269.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   16.029(5)
_cell_length_b                   5.2953(17)
_cell_length_c                   29.392(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.478(4)
_cell_angle_gamma                90.00
_cell_volume                     2492.4(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8495
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2138
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2138
_reflns_number_gt                1989
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of 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^)+(0.0400P)^2^+39.0000P] 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         2138
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0896
_refine_ls_wR_factor_ref         0.2234
_refine_ls_wR_factor_gt          0.2226
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.87731(11) 0.1843(3) 0.52390(5) 0.0438(5) Uani 1 1 d . . .
C1 C 0.8942(4) 0.3997(11) 0.56865(19) 0.0296(13) Uani 1 1 d . . .
C2 C 0.8434(4) 0.3926(11) 0.60548(19) 0.0312(13) Uani 1 1 d . . .
H2 H 0.8009 0.2684 0.6071 0.030(16) Uiso 1 1 calc R . .
C3 C 0.8553(3) 0.5692(11) 0.63998(19) 0.0278(12) Uani 1 1 d . . .
H3 H 0.8196 0.5693 0.6649 0.042(18) Uiso 1 1 calc R . .
C4 C 0.9196(3) 0.7472(10) 0.63830(18) 0.0232(11) Uani 1 1 d . . .
C5 C 0.9715(3) 0.7441(11) 0.60121(19) 0.0287(13) Uani 1 1 d . . .
H5 H 1.0157 0.8630 0.6000 0.024(14) Uiso 1 1 calc R . .
C6 C 0.9595(3) 0.5709(12) 0.56638(19) 0.0315(13) Uani 1 1 d . . .
H6 H 0.9951 0.5690 0.5414 0.046(19) Uiso 1 1 calc R . .
C7 C 0.9321(3) 0.9487(11) 0.67256(18) 0.0260(12) Uani 1 1 d . . .
H7 H 0.9781 1.0609 0.6708 0.05(2) Uiso 1 1 calc R . .
N8 N 0.8814(3) 0.9725(8) 0.70442(15) 0.0246(10) Uani 1 1 d . . .
O9 O 0.9049(2) 1.1922(7) 0.73068(12) 0.0277(9) Uani 1 1 d . . .
C10 C 0.8534(3) 1.2378(10) 0.76590(18) 0.0232(11) Uani 1 1 d . . .
O10 O 0.7975(2) 1.0990(8) 0.77609(13) 0.0302(9) Uani 1 1 d . . .
C11 C 0.8780(3) 1.4866(10) 0.78724(18) 0.0258(12) Uani 1 1 d . . .
H11A H 0.8675 1.6232 0.7647 0.018(13) Uiso 1 1 calc R . .
H11B H 0.9387 1.4844 0.7953 0.040(17) Uiso 1 1 calc R . .
C12 C 0.8308(3) 1.5434(11) 0.82961(18) 0.0261(12) Uani 1 1 d . . .
H12A H 0.8434 1.7187 0.8394 0.025(15) Uiso 1 1 calc R . .
H12B H 0.7701 1.5335 0.8218 0.033(16) Uiso 1 1 calc R . .
C13 C 0.8507(3) 1.3701(11) 0.86855(18) 0.0282(13) Uani 1 1 d . . .
O13 O 0.8966(3) 1.1877(8) 0.86771(14) 0.0367(10) Uani 1 1 d . . .
O14 O 0.8121(3) 1.4364(8) 0.90616(13) 0.0362(10) Uani 1 1 d . . .
C15 C 0.8245(4) 1.2762(14) 0.9452(2) 0.0421(16) Uani 1 1 d . . .
H15A H 0.7991 1.1109 0.9388 0.07(2) Uiso 1 1 calc R . .
H15B H 0.7984 1.3531 0.9714 0.044(19) Uiso 1 1 calc R . .
H15C H 0.8845 1.2551 0.9521 0.07(2) Uiso 1 1 calc R . .

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
Cl1 0.0552(10) 0.0335(9) 0.0427(9) -0.0107(7) 0.0020(7) -0.0089(8)
C1 0.033(3) 0.021(3) 0.036(3) -0.005(2) -0.002(2) 0.000(2)
C2 0.028(3) 0.023(3) 0.042(3) 0.001(2) 0.001(2) -0.005(3)
C3 0.019(3) 0.027(3) 0.037(3) 0.001(2) 0.006(2) -0.001(2)
C4 0.021(3) 0.013(3) 0.036(3) 0.000(2) -0.001(2) 0.001(2)
C5 0.017(3) 0.026(3) 0.044(3) -0.005(2) 0.005(2) -0.007(2)
C6 0.022(3) 0.034(3) 0.038(3) -0.005(3) 0.007(2) -0.004(3)
C7 0.021(3) 0.020(3) 0.037(3) -0.002(2) 0.003(2) -0.004(2)
N8 0.023(2) 0.012(2) 0.038(3) -0.0032(18) 0.0022(18) -0.0038(18)
O9 0.0212(19) 0.024(2) 0.038(2) -0.0082(17) 0.0067(15) -0.0078(16)
C10 0.021(3) 0.018(3) 0.031(3) 0.002(2) 0.000(2) 0.004(2)
O10 0.024(2) 0.021(2) 0.046(2) -0.0022(17) 0.0094(16) -0.0042(17)
C11 0.024(3) 0.018(3) 0.035(3) 0.001(2) 0.002(2) -0.002(2)
C12 0.022(3) 0.017(3) 0.039(3) -0.001(2) 0.000(2) 0.004(2)
C13 0.022(3) 0.030(3) 0.032(3) -0.001(2) -0.001(2) 0.000(3)
O13 0.033(2) 0.031(2) 0.046(2) 0.0043(19) 0.0031(17) 0.016(2)
O14 0.036(2) 0.037(3) 0.036(2) 0.0049(19) 0.0092(17) 0.012(2)
C15 0.043(4) 0.044(4) 0.040(4) 0.009(3) 0.006(3) -0.001(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.753(6) . ?
C1 C2 1.382(8) . ?
C1 C6 1.388(8) . ?
C2 C3 1.387(8) . ?
C3 C4 1.399(8) . ?
C4 C5 1.399(7) . ?
C4 C7 1.475(7) . ?
C5 C6 1.382(8) . ?
C7 N8 1.272(7) . ?
N8 O9 1.437(6) . ?
O9 C10 1.374(6) . ?
C10 O10 1.206(6) . ?
C10 C11 1.505(8) . ?
C11 C12 1.516(7) . ?
C12 C13 1.491(8) . ?
C13 O13 1.215(7) . ?
C13 O14 1.337(7) . ?
O14 C15 1.433(7) . ?

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 121.7(5) . . ?
C2 C1 Cl1 119.5(4) . . ?
C6 C1 Cl1 118.7(4) . . ?
C1 C2 C3 119.2(5) . . ?
C2 C3 C4 120.5(5) . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 C7 122.8(5) . . ?
C5 C4 C7 118.2(5) . . ?
C6 C5 C4 121.1(5) . . ?
C5 C6 C1 118.6(5) . . ?
N8 C7 C4 120.2(5) . . ?
C7 N8 O9 108.4(4) . . ?
C10 O9 N8 113.2(4) . . ?
O10 C10 O9 123.9(5) . . ?
O10 C10 C11 127.9(5) . . ?
O9 C10 C11 108.2(4) . . ?
C10 C11 C12 112.6(5) . . ?
C13 C12 C11 114.2(5) . . ?
O13 C13 O14 121.9(5) . . ?
O13 C13 C12 125.7(5) . . ?
O14 C13 C12 112.4(5) . . ?
C13 O14 C15 116.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         1.028
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.109