# Electronic Supplementary Material (ESI) for ChemComm.
# 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 
#  to carry out CIF format checking respectively.
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data_1_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Cl N O'
_chemical_formula_weight         78.48

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.9603(5)
_cell_length_b                   25.1844(15)
_cell_length_c                   12.0025(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.5390(10)
_cell_angle_gamma                90.00
_cell_volume                     2329.2(2)
_cell_formula_units_Z            30
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1170
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7960
_exptl_absorpt_correction_T_max  0.8699
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18529
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.50
_reflns_number_total             8636
_reflns_number_gt                7440
_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 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)+(0.0981P)²+5.9480P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0002(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8636
_refine_ls_number_parameters     792
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   0.591
_refine_ls_restrained_S_all      0.591
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9225(3) 0.65600(7) 0.71533(17) 0.0265(4) Uani 1 1 d . . .
C2 C 0.9828(3) 0.63333(8) 0.62782(19) 0.0287(4) Uani 1 1 d . . .
C3 C 0.9322(3) 0.65555(8) 0.51923(19) 0.0282(4) Uani 1 1 d . . .
C4 C 0.8227(2) 0.69911(7) 0.50051(16) 0.0231(4) Uani 1 1 d . . .
C5 C 0.7641(2) 0.72346(7) 0.58923(16) 0.0213(4) Uani 1 1 d . . .
C6 C 0.8178(3) 0.70078(7) 0.69801(17) 0.0241(4) Uani 1 1 d . . .
C7 C 0.6613(2) 0.77298(7) 0.57472(16) 0.0221(4) Uani 1 1 d . . .
C8 C 0.5335(2) 0.78181(7) 0.62420(17) 0.0230(4) Uani 1 1 d . . .
C9 C 0.4457(2) 0.83412(7) 0.61690(15) 0.0209(4) Uani 1 1 d . . .
C10 C 0.2685(2) 0.84312(7) 0.57102(16) 0.0231(4) Uani 1 1 d . . .
C11 C 0.1924(3) 0.89269(8) 0.56674(17) 0.0244(4) Uani 1 1 d . . .
C12 C 0.2979(2) 0.93564(7) 0.60644(16) 0.0242(4) Uani 1 1 d . . .
C13 C 0.4766(2) 0.93142(7) 0.65511(15) 0.0225(4) Uani 1 1 d . . .
C14 C 0.5415(2) 0.87976(7) 0.65906(15) 0.0212(4) Uani 1 1 d . . .
C15 C 0.5878(3) 0.97717(8) 0.70489(17) 0.0256(4) Uani 1 1 d . . .
C16 C 0.6758(3) 0.97860(8) 0.81354(18) 0.0267(4) Uani 1 1 d . . .
C17 C 0.7900(2) 1.02363(7) 0.86380(17) 0.0238(4) Uani 1 1 d . . .
C18 C 0.8190(2) 1.04158(7) 0.97752(16) 0.0239(4) Uani 1 1 d . . .
C19 C 0.9255(2) 1.08459(8) 1.01901(17) 0.0270(4) Uani 1 1 d . . .
C20 C 1.0048(3) 1.11196(8) 0.94693(18) 0.0284(4) Uani 1 1 d . . .
C21 C 0.9750(2) 1.09563(8) 0.83330(18) 0.0276(4) Uani 1 1 d . . .
C22 C 0.8729(2) 1.05188(8) 0.79283(18) 0.0266(4) Uani 1 1 d . . .
C23 C 0.5773(3) 0.15607(7) 0.78453(17) 0.0265(4) Uani 1 1 d . . .
C24 C 0.5173(3) 0.13328(8) 0.87214(19) 0.0290(4) Uani 1 1 d . . .
C25 C 0.5678(3) 0.15558(8) 0.98077(19) 0.0279(4) Uani 1 1 d . . .
C26 C 0.6774(2) 0.19905(7) 0.99928(16) 0.0229(4) Uani 1 1 d . . .
C27 C 0.7360(2) 0.22344(7) 0.91081(16) 0.0212(4) Uani 1 1 d . . .
C28 C 0.6824(2) 0.20078(7) 0.80196(17) 0.0237(4) Uani 1 1 d . . .
C29 C 0.8388(2) 0.27293(7) 0.92542(16) 0.0220(4) Uani 1 1 d . . .
C30 C 0.9664(2) 0.28176(7) 0.87577(17) 0.0232(4) Uani 1 1 d . . .
C31 C 1.0544(2) 0.33409(7) 0.88317(16) 0.0213(4) Uani 1 1 d . . .
C32 C 1.2317(2) 0.34303(7) 0.92887(16) 0.0229(4) Uani 1 1 d . . .
C33 C 1.3074(3) 0.39270(8) 0.93310(17) 0.0241(4) Uani 1 1 d . . .
C34 C 1.2020(2) 0.43569(7) 0.89360(16) 0.0241(4) Uani 1 1 d . . .
C35 C 1.0233(2) 0.43137(7) 0.84485(15) 0.0229(4) Uani 1 1 d . . .
C36 C 0.9584(2) 0.37969(7) 0.84075(15) 0.0209(4) Uani 1 1 d . . .
C37 C 0.9122(2) 0.47718(8) 0.79494(17) 0.0254(4) Uani 1 1 d . . .
C38 C 0.8242(3) 0.47865(8) 0.68649(18) 0.0268(4) Uani 1 1 d . . .
C39 C 0.7101(2) 0.52364(7) 0.63647(17) 0.0242(4) Uani 1 1 d . . .
C40 C 0.6270(2) 0.55184(8) 0.70722(18) 0.0269(4) Uani 1 1 d . . .
C41 C 0.5248(2) 0.59567(8) 0.66652(18) 0.0275(4) Uani 1 1 d . . .
C42 C 0.4955(3) 0.61200(8) 0.55336(19) 0.0290(4) Uani 1 1 d . . .
C43 C 0.5747(2) 0.58466(8) 0.48123(17) 0.0265(4) Uani 1 1 d . . .
C44 C 0.6808(2) 0.54155(7) 0.52246(16) 0.0243(4) Uani 1 1 d . . .
Cl1 Cl 1.06482(7) 1.13096(2) 0.73870(5) 0.04030(15) Uani 1 1 d . . .
Cl2 Cl 0.43531(7) 0.63104(2) 0.76136(5) 0.04055(15) Uani 1 1 d . . .
Cl3 Cl 0.98434(8) 0.62807(2) 0.85160(5) 0.03895(14) Uani 1 1 d . . .
Cl4 Cl 0.51561(8) 0.12810(2) 0.64836(5) 0.03875(14) Uani 1 1 d . . .
H1 H 1.073(3) 1.1390(10) 0.972(2) 0.036(6) Uiso 1 1 d . . .
H2 H 0.863(3) 1.0399(9) 0.721(2) 0.032(6) Uiso 1 1 d . . .
H3 H 0.940(3) 1.0962(10) 1.097(2) 0.038(6) Uiso 1 1 d . . .
O10 O 0.6788(2) 0.97201(6) 1.04564(14) 0.0411(4) Uani 1 1 d . . .
H5 H 0.788(3) 0.7168(9) 0.758(2) 0.029(6) Uiso 1 1 d . . .
H6 H 1.061(3) 0.6010(9) 0.6397(19) 0.027(6) Uiso 1 1 d . . .
H7 H 0.973(3) 0.6418(10) 0.455(2) 0.035(6) Uiso 1 1 d . . .
H8 H 0.077(3) 0.8982(9) 0.5359(19) 0.027(6) Uiso 1 1 d . . .
H9 H 0.427(3) 0.6400(10) 0.527(2) 0.035(6) Uiso 1 1 d . . .
H10 H 0.559(3) 0.5957(10) 0.402(2) 0.035(6) Uiso 1 1 d . . .
H11 H 0.637(3) 0.5397(9) 0.780(2) 0.031(6) Uiso 1 1 d . . .
H12 H 1.422(3) 0.3976(8) 0.9620(19) 0.023(5) Uiso 1 1 d . . .
H13 H 0.532(3) 0.1415(9) 1.045(2) 0.030(6) Uiso 1 1 d . . .
H14 H 0.442(3) 0.1015(9) 0.859(2) 0.031(6) Uiso 1 1 d . . .
H15 H 0.712(3) 0.2175(9) 0.740(2) 0.026(5) Uiso 1 1 d . . .
H16 H 0.806(3) 0.2982(9) 0.9708(18) 0.021(5) Uiso 1 1 d . . .
H17 H 1.006(3) 0.2567(10) 0.837(2) 0.034(6) Uiso 1 1 d . . .
H18 H 0.691(3) 0.7990(8) 0.5276(18) 0.020(5) Uiso 1 1 d . . .
H19 H 0.495(3) 0.7565(10) 0.664(2) 0.037(6) Uiso 1 1 d . . .
H20 H 0.910(3) 0.5067(10) 0.845(2) 0.040(7) Uiso 1 1 d . . .
H22 H 0.590(3) 1.0068(11) 0.655(2) 0.046(7) Uiso 1 1 d . . .
H23 H 0.832(3) 0.4511(10) 0.637(2) 0.032(6) Uiso 1 1 d . . .
N1 N 0.7630(2) 0.71781(7) 0.38196(15) 0.0315(4) Uani 1 1 d . . .
N2 N 0.1520(2) 0.79911(7) 0.52030(16) 0.0299(4) Uani 1 1 d . . .
N3 N 0.2111(2) 0.98792(7) 0.59785(16) 0.0333(4) Uani 1 1 d . . .
N4 N 0.7276(2) 0.87195(6) 0.71567(15) 0.0276(4) Uani 1 1 d . . .
N5 N 0.7314(2) 1.01779(7) 1.05992(14) 0.0280(4) Uani 1 1 d . . .
N6 N 0.7683(2) 0.51775(7) 0.44005(14) 0.0284(4) Uani 1 1 d . . .
N7 N 1.2888(2) 0.48777(7) 0.90213(16) 0.0339(4) Uani 1 1 d . . .
N8 N 0.7722(2) 0.37183(6) 0.78413(15) 0.0280(4) Uani 1 1 d . . .
N9 N 1.3479(2) 0.29908(7) 0.97963(16) 0.0302(4) Uani 1 1 d . . .
N10 N 0.7371(2) 0.21777(7) 1.11810(15) 0.0315(4) Uani 1 1 d . . .
O1 O 0.6341(3) 0.74500(8) 0.35564(15) 0.0586(5) Uani 1 1 d . . .
O2 O 0.8455(3) 0.70484(8) 0.31396(16) 0.0584(5) Uani 1 1 d . . .
O3 O 0.7615(2) 0.85084(6) 0.81021(14) 0.0403(4) Uani 1 1 d . . .
O4 O 0.8333(2) 0.88713(7) 0.66505(16) 0.0433(4) Uani 1 1 d . . .
O5 O 0.2829(2) 1.02520(6) 0.56298(19) 0.0569(5) Uani 1 1 d . . .
O6 O 0.0710(2) 0.98978(7) 0.62143(15) 0.0454(4) Uani 1 1 d . . .
O7 O -0.00291(19) 0.80708(6) 0.49924(15) 0.0392(4) Uani 1 1 d . . .
O8 O 0.2148(2) 0.75818(7) 0.4975(2) 0.0723(7) Uani 1 1 d . . .
O9 O 0.7147(2) 1.04546(7) 1.14017(14) 0.0469(4) Uani 1 1 d . . .
O11 O 0.8214(2) 0.47200(6) 0.45447(14) 0.0415(4) Uani 1 1 d . . .
O12 O 0.7854(2) 0.54542(7) 0.35977(14) 0.0474(4) Uani 1 1 d . . .
O13 O 0.6668(2) 0.38707(7) 0.83511(16) 0.0432(4) Uani 1 1 d . . .
O14 O 0.7385(2) 0.35078(6) 0.68982(14) 0.0405(4) Uani 1 1 d . . .
O15 O 1.2169(2) 0.52511(6) 0.93676(19) 0.0570(5) Uani 1 1 d . . .
O16 O 1.4290(2) 0.48969(7) 0.87852(15) 0.0455(4) Uani 1 1 d . . .
O17 O 1.2849(2) 0.25805(8) 1.0022(2) 0.0731(7) Uani 1 1 d . . .
O18 O 1.50291(19) 0.30698(6) 1.00070(15) 0.0392(4) Uani 1 1 d . . .
O19 O 0.6546(3) 0.20481(8) 1.18620(16) 0.0581(5) Uani 1 1 d . . .
O20 O 0.8660(3) 0.24495(8) 1.14439(15) 0.0577(5) Uani 1 1 d . . .
H1 H 0.670(3) 0.9501(10) 0.865(2) 0.033(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(3) . ?
C1 C6 1.386(3) . ?
C1 Cl3 1.734(2) . ?
C2 C3 1.382(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.406(3) . ?
C4 N1 1.460(3) . ?
C5 C6 1.391(3) . ?
C5 C7 1.478(3) . ?
C7 C8 1.320(3) . ?
C8 C9 1.484(3) . ?
C9 C10 1.398(3) . ?
C9 C14 1.402(3) . ?
C10 C11 1.383(3) . ?
C10 N2 1.475(2) . ?
C11 C12 1.379(3) . ?
C12 C13 1.400(3) . ?
C12 N3 1.478(2) . ?
C13 C14 1.396(3) . ?
C13 C15 1.484(3) . ?
C14 N4 1.480(2) . ?
C15 C16 1.317(3) . ?
C16 C17 1.483(3) . ?
C17 C22 1.396(3) . ?
C17 C18 1.401(3) . ?
C18 C19 1.389(3) . ?
C18 N5 1.473(3) . ?
C19 C20 1.377(3) . ?
C20 C21 1.387(3) . ?
C21 C22 1.383(3) . ?
C21 Cl1 1.732(2) . ?
C23 C24 1.384(3) . ?
C23 C28 1.387(3) . ?
C23 Cl4 1.734(2) . ?
C24 C25 1.383(3) . ?
C25 C26 1.383(3) . ?
C26 C27 1.404(3) . ?
C26 N10 1.463(3) . ?
C27 C28 1.391(3) . ?
C27 C29 1.477(3) . ?
C29 C30 1.319(3) . ?
C30 C31 1.485(3) . ?
C31 C32 1.398(3) . ?
C31 C36 1.402(3) . ?
C32 C33 1.384(3) . ?
C32 N9 1.473(2) . ?
C33 C34 1.379(3) . ?
C34 C35 1.400(3) . ?
C34 N7 1.474(2) . ?
C35 C36 1.397(3) . ?
C35 C37 1.485(3) . ?
C36 N8 1.481(2) . ?
C37 C38 1.315(3) . ?
C38 C39 1.482(3) . ?
C39 C40 1.395(3) . ?
C39 C44 1.404(3) . ?
C40 C41 1.385(3) . ?
C41 C42 1.382(3) . ?
C41 Cl2 1.733(2) . ?
C42 C43 1.377(3) . ?
C43 C44 1.388(3) . ?
C44 N6 1.472(3) . ?
O10 N5 1.224(2) . ?
N1 O1 1.208(2) . ?
N1 O2 1.214(2) . ?
N2 O8 1.207(2) . ?
N2 O7 1.212(2) . ?
N3 O6 1.218(3) . ?
N3 O5 1.226(3) . ?
N4 O4 1.216(2) . ?
N4 O3 1.220(2) . ?
N5 O9 1.223(2) . ?
N6 O12 1.224(2) . ?
N6 O11 1.224(2) . ?
N7 O16 1.220(3) . ?
N7 O15 1.226(3) . ?
N8 O14 1.217(2) . ?
N8 O13 1.218(2) . ?
N9 O17 1.209(2) . ?
N9 O18 1.212(2) . ?
N10 O20 1.208(3) . ?
N10 O19 1.214(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
C2 C1 C6 122.14(19) . . ?
C2 C1 Cl3 118.57(15) . . ?
C6 C1 Cl3 119.28(16) . . ?
C3 C2 C1 118.34(18) . . ?
C2 C3 C4 119.75(18) . . ?
C3 C4 C5 122.54(18) . . ?
C3 C4 N1 116.82(17) . . ?
C5 C4 N1 120.58(17) . . ?
C6 C5 C4 116.73(17) . . ?
C6 C5 C7 119.21(16) . . ?
C4 C5 C7 123.91(17) . . ?
C1 C6 C5 120.43(18) . . ?
C8 C7 C5 123.78(18) . . ?
C7 C8 C9 121.89(17) . . ?
C10 C9 C14 114.40(16) . . ?
C10 C9 C8 125.52(17) . . ?
C14 C9 C8 120.07(17) . . ?
C11 C10 C9 123.37(17) . . ?
C11 C10 N2 116.05(17) . . ?
C9 C10 N2 120.55(16) . . ?
C12 C11 C10 118.20(18) . . ?
C11 C12 C13 123.47(17) . . ?
C11 C12 N3 116.19(17) . . ?
C13 C12 N3 120.32(17) . . ?
C14 C13 C12 114.42(17) . . ?
C14 C13 C15 122.12(17) . . ?
C12 C13 C15 123.36(17) . . ?
C13 C14 C9 126.06(17) . . ?
C13 C14 N4 117.29(16) . . ?
C9 C14 N4 116.62(16) . . ?
C16 C15 C13 122.36(18) . . ?
C15 C16 C17 122.89(19) . . ?
C22 C17 C18 116.27(17) . . ?
C22 C17 C16 118.47(17) . . ?
C18 C17 C16 125.24(18) . . ?
C19 C18 C17 122.52(18) . . ?
C19 C18 N5 115.20(17) . . ?
C17 C18 N5 122.21(17) . . ?
C20 C19 C18 120.00(19) . . ?
C19 C20 C21 118.52(19) . . ?
C22 C21 C20 121.45(19) . . ?
C22 C21 Cl1 118.82(16) . . ?
C20 C21 Cl1 119.72(16) . . ?
C21 C22 C17 121.20(19) . . ?
C24 C23 C28 122.15(19) . . ?
C24 C23 Cl4 118.54(16) . . ?
C28 C23 Cl4 119.30(15) . . ?
C25 C24 C23 118.28(18) . . ?
C24 C25 C26 119.69(18) . . ?
C25 C26 C27 122.74(18) . . ?
C25 C26 N10 116.68(17) . . ?
C27 C26 N10 120.53(17) . . ?
C28 C27 C26 116.68(17) . . ?
C28 C27 C29 119.21(16) . . ?
C26 C27 C29 123.96(17) . . ?
C23 C28 C27 120.41(18) . . ?
C30 C29 C27 123.72(17) . . ?
C29 C30 C31 121.87(17) . . ?
C32 C31 C36 114.51(16) . . ?
C32 C31 C30 125.54(16) . . ?
C36 C31 C30 119.94(17) . . ?
C33 C32 C31 123.20(17) . . ?
C33 C32 N9 116.20(17) . . ?
C31 C32 N9 120.57(16) . . ?
C34 C33 C32 118.36(18) . . ?
C33 C34 C35 123.34(17) . . ?
C33 C34 N7 116.13(17) . . ?
C35 C34 N7 120.51(17) . . ?
C36 C35 C34 114.53(17) . . ?
C36 C35 C37 122.16(17) . . ?
C34 C35 C37 123.22(17) . . ?
C35 C36 C31 125.97(17) . . ?
C35 C36 N8 117.35(16) . . ?
C31 C36 N8 116.66(16) . . ?
C38 C37 C35 122.45(18) . . ?
C37 C38 C39 122.88(19) . . ?
C40 C39 C44 116.21(17) . . ?
C40 C39 C38 118.61(18) . . ?
C44 C39 C38 125.16(18) . . ?
C41 C40 C39 121.15(19) . . ?
C42 C41 C40 121.55(19) . . ?
C42 C41 Cl2 119.78(16) . . ?
C40 C41 Cl2 118.67(16) . . ?
C43 C42 C41 118.57(19) . . ?
C42 C43 C44 120.05(19) . . ?
C43 C44 C39 122.42(18) . . ?
C43 C44 N6 115.27(17) . . ?
C39 C44 N6 122.22(17) . . ?
O1 N1 O2 123.0(2) . . ?
O1 N1 C4 119.01(17) . . ?
O2 N1 C4 118.02(19) . . ?
O8 N2 O7 123.51(18) . . ?
O8 N2 C10 118.84(17) . . ?
O7 N2 C10 117.57(16) . . ?
O6 N3 O5 125.59(19) . . ?
O6 N3 C12 117.19(18) . . ?
O5 N3 C12 117.15(18) . . ?
O4 N4 O3 125.62(18) . . ?
O4 N4 C14 117.85(17) . . ?
O3 N4 C14 116.54(16) . . ?
O10 N5 O9 123.10(18) . . ?
O10 N5 C18 119.48(16) . . ?
O9 N5 C18 117.42(17) . . ?
O12 N6 O11 122.97(18) . . ?
O12 N6 C44 117.51(17) . . ?
O11 N6 C44 119.52(17) . . ?
O16 N7 O15 125.47(19) . . ?
O16 N7 C34 117.36(18) . . ?
O15 N7 C34 117.10(18) . . ?
O14 N8 O13 125.85(18) . . ?
O14 N8 C36 116.52(16) . . ?
O13 N8 C36 117.63(17) . . ?
O17 N9 O18 123.46(18) . . ?
O17 N9 C32 118.85(17) . . ?
O18 N9 C32 117.63(16) . . ?
O20 N10 O19 122.9(2) . . ?
O20 N10 C26 118.94(17) . . ?
O19 N10 C26 118.11(19) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 965295'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 N5 O10'
_chemical_formula_weight         535.43

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   '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                   24.48(2)
_cell_length_b                   8.379(6)
_cell_length_c                   11.878(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.275(14)
_cell_angle_gamma                90.00
_cell_volume                     2339(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_T_max  0.9904
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5631
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0667
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2042
_reflns_number_gt                1184
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0764P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2042
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
N1 N 0.32599(12) 0.1820(3) 1.0757(3) 0.0654(9) Uani 1 1 d . . .
N2 N 0.45249(12) 0.3660(3) 0.9027(3) 0.0481(7) Uani 1 1 d . . .
N3 N 0.5000 -0.1519(4) 0.7500 0.0442(9) Uani 1 2 d S . .
C1 C 0.28547(14) -0.3614(4) 1.1904(3) 0.0659(10) Uani 1 1 d . . .
H1A H 0.2636 -0.2976 1.2291 0.099 Uiso 1 1 calc R . .
H1B H 0.3136 -0.4206 1.2478 0.099 Uiso 1 1 calc R . .
H1C H 0.2607 -0.4341 1.1373 0.099 Uiso 1 1 calc R . .
C2 C 0.31458(13) -0.2543(4) 1.1229(3) 0.0497(8) Uani 1 1 d . . .
C3 C 0.30925(12) -0.0905(4) 1.1268(3) 0.0516(9) Uani 1 1 d . . .
H3 H 0.2881 -0.0461 1.1729 0.062 Uiso 1 1 calc R . .
C4 C 0.33487(12) 0.0091(3) 1.0631(3) 0.0459(8) Uani 1 1 d . . .
C5 C 0.36772(12) -0.0490(3) 0.9922(3) 0.0411(7) Uani 1 1 d . . .
C6 C 0.37227(14) -0.2159(3) 0.9900(3) 0.0527(9) Uani 1 1 d . . .
H6 H 0.3932 -0.2616 0.9440 0.063 Uiso 1 1 calc R . .
C7 C 0.34695(14) -0.3147(4) 1.0536(3) 0.0556(9) Uani 1 1 d . . .
H7 H 0.3517 -0.4246 1.0500 0.067 Uiso 1 1 calc R . .
C8 C 0.39586(13) 0.0518(3) 0.9220(3) 0.0453(8) Uani 1 1 d . . .
H8 H 0.3802 0.1512 0.8972 0.054 Uiso 1 1 calc R . .
C9 C 0.44218(12) 0.0078(3) 0.8927(2) 0.0397(7) Uani 1 1 d . . .
H9 H 0.4576 -0.0912 0.9194 0.048 Uiso 1 1 calc R . .
C10 C 0.47115(11) 0.1008(3) 0.8223(2) 0.0363(7) Uani 1 1 d . . .
C11 C 0.47488(12) 0.2686(3) 0.8211(2) 0.0386(7) Uani 1 1 d . . .
C12 C 0.5000 0.3521(5) 0.7500 0.0432(10) Uani 1 2 d S . .
H12 H 0.5000 0.4631 0.7500 0.052 Uiso 1 2 calc SR . .
C13 C 0.5000 0.0257(4) 0.7500 0.0351(9) Uani 1 2 d S . .
O1 O 0.32008(14) 0.2289(3) 1.1700(3) 0.1018(11) Uani 1 1 d . . .
O2 O 0.32503(16) 0.2703(3) 0.9966(3) 0.1152(13) Uani 1 1 d . . .
O3 O 0.47361(10) 0.3450(2) 1.0078(2) 0.0630(7) Uani 1 1 d . . .
O4 O 0.41646(10) 0.4656(3) 0.8601(2) 0.0710(8) Uani 1 1 d . . .
O5 O 0.54578(10) -0.2194(2) 0.7808(2) 0.0627(7) 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
N1 O2 1.191(4) . ?
N1 O1 1.233(4) . ?
N1 C4 1.478(4) . ?
N2 O4 1.217(3) . ?
N2 O3 1.223(3) . ?
N2 C11 1.485(4) . ?
N3 O5 1.216(3) 2_656 ?
N3 O5 1.216(3) . ?
N3 C13 1.489(5) . ?
C1 C2 1.509(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.380(4) . ?
C2 C7 1.388(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(4) . ?
C5 C6 1.403(4) . ?
C5 C8 1.485(4) . ?
C6 C7 1.380(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.328(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.464(4) . ?
C9 H9 0.9300 . ?
C10 C13 1.404(3) . ?
C10 C11 1.409(4) . ?
C11 C12 1.368(3) . ?
C12 C11 1.368(3) 2_656 ?
C12 H12 0.9300 . ?
C13 C10 1.404(3) 2_656 ?

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
O2 N1 O1 122.5(3) . . ?
O2 N1 C4 120.0(3) . . ?
O1 N1 C4 117.5(3) . . ?
O4 N2 O3 125.0(3) . . ?
O4 N2 C11 117.5(3) . . ?
O3 N2 C11 117.4(3) . . ?
O5 N3 O5 124.6(3) 2_656 . ?
O5 N3 C13 117.68(17) 2_656 . ?
O5 N3 C13 117.68(17) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.2(3) . . ?
C3 C2 C1 120.7(3) . . ?
C7 C2 C1 122.1(3) . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 122.7(3) . . ?
C3 C4 N1 115.6(3) . . ?
C5 C4 N1 121.7(3) . . ?
C6 C5 C4 114.7(3) . . ?
C6 C5 C8 120.3(3) . . ?
C4 C5 C8 124.9(3) . . ?
C7 C6 C5 122.6(3) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C2 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C9 C8 C5 123.6(3) . . ?
C9 C8 H8 118.2 . . ?
C5 C8 H8 118.2 . . ?
C8 C9 C10 126.0(3) . . ?
C8 C9 H9 117.0 . . ?
C10 C9 H9 117.0 . . ?
C13 C10 C11 113.3(3) . . ?
C13 C10 C9 121.3(2) . . ?
C11 C10 C9 125.4(2) . . ?
C12 C11 C10 123.9(3) . . ?
C12 C11 N2 115.7(3) . . ?
C10 C11 N2 120.3(2) . . ?
C11 C12 C11 118.4(4) . 2_656 ?
C11 C12 H12 120.8 . . ?
C11 C12 H12 120.8 2_656 . ?
C10 C13 C10 126.8(3) . 2_656 ?
C10 C13 N3 116.60(16) . . ?
C10 C13 N3 116.60(16) 2_656 . ?

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
C7 C2 C3 C4 0.5(5) . . . . ?
C1 C2 C3 C4 -178.7(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C2 C3 C4 N1 -179.7(3) . . . . ?
O2 N1 C4 C3 -149.8(4) . . . . ?
O1 N1 C4 C3 30.5(4) . . . . ?
O2 N1 C4 C5 30.9(5) . . . . ?
O1 N1 C4 C5 -148.7(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
N1 C4 C5 C6 179.7(3) . . . . ?
C3 C4 C5 C8 179.8(3) . . . . ?
N1 C4 C5 C8 -1.0(5) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C8 C5 C6 C7 180.0(3) . . . . ?
C5 C6 C7 C2 0.9(5) . . . . ?
C3 C2 C7 C6 -0.8(5) . . . . ?
C1 C2 C7 C6 178.4(3) . . . . ?
C6 C5 C8 C9 -27.3(5) . . . . ?
C4 C5 C8 C9 153.4(3) . . . . ?
C5 C8 C9 C10 178.9(2) . . . . ?
C8 C9 C10 C13 -148.9(3) . . . . ?
C8 C9 C10 C11 33.0(4) . . . . ?
C13 C10 C11 C12 5.0(4) . . . . ?
C9 C10 C11 C12 -176.8(2) . . . . ?
C13 C10 C11 N2 -173.0(2) . . . . ?
C9 C10 C11 N2 5.3(4) . . . . ?
O4 N2 C11 C12 59.2(3) . . . . ?
O3 N2 C11 C12 -117.5(3) . . . . ?
O4 N2 C11 C10 -122.7(3) . . . . ?
O3 N2 C11 C10 60.6(3) . . . . ?
C10 C11 C12 C11 -2.73(19) . . . 2_656 ?
N2 C11 C12 C11 175.3(3) . . . 2_656 ?
C11 C10 C13 C10 -2.31(16) . . . 2_656 ?
C9 C10 C13 C10 179.4(3) . . . 2_656 ?
C11 C10 C13 N3 177.69(16) . . . . ?
C9 C10 C13 N3 -0.6(3) . . . . ?
O5 N3 C13 C10 60.07(18) 2_656 . . . ?
O5 N3 C13 C10 -119.93(18) . . . . ?
O5 N3 C13 C10 -119.93(18) 2_656 . . 2_656 ?
O5 N3 C13 C10 60.07(18) . . . 2_656 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 999375'
