# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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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# 
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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_R2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H23 N O3'
_chemical_formula_sum            'C28 H23 N O3'
_chemical_formula_weight         421.47

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_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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                   18.491(2)
_cell_length_b                   5.2471(5)
_cell_length_c                   22.346(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.654(4)
_cell_angle_gamma                90.00
_cell_volume                     2168.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3741
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      20.37

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_T_max  0.9967
_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            20292
_diffrn_reflns_av_R_equivalents  0.1379
_diffrn_reflns_av_sigmaI/netI    0.1039
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3976
_reflns_number_gt                1780
_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)+(0.0647P)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         3976
_refine_ls_number_parameters     288
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1708
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL R2 in P2(1)/n
CELL 0.71073 18.4909 5.2471 22.3461 90.000 90.654 90.000
ZERR 4.00 0.0020 0.0005 0.0025 0.000 0.004 0.000
LATT 1
SYMM -x+1/2, y+1/2, -z+1/2
SFAC C H N O
UNIT 112 92 4 12
TEMP 23
ACTA
L.S. 12
OMIT 2 0 0
SIZE 0.36 0.08 0.04
DFIX 1.36 C23 C24A C24A C25A C25A C26A C26A C27A C27A C28A C28A C23
DFIX 1.36 C23 C24B C24B C25B C25B C26B C26B C27B C27B C28B C28B C23
DANG 2.37 C23 C25A C25A C27A C27A C23 C24A C26A C26A C28A C28A C24A
DANG 2.37 C23 C25B C25B C27B C27B C23 C24B C26B C26B C28B C28B C24B
FLAT C23 C24A C25A C26A C27A C28A
FLAT C23 C24B C25B C26B C27B C28B
EADP C24A C25A C26A C27A C28A
EADP C24B C25B C26B C27B C28B
FMAP 2
PLAN 5
HTAB
BOND $H
CONF
WGHT    0.064700
FVAR       0.16723   0.52666
O1    4    1.004142    0.548363    0.791991    11.00000    0.04619    0.06924 =
         0.05407   -0.01482    0.01220   -0.01389
O2    4    0.956287    0.684802    0.876849    11.00000    0.07536    0.05613 =
         0.05412   -0.01315    0.01643   -0.00776
O3    4    0.879345    0.645864    1.077748    11.00000    0.07469    0.06917 =
         0.04967   -0.00874    0.00902    0.00547
N1    3    0.770970   -0.022901    0.910570    11.00000    0.04054    0.04927 =
         0.06899    0.00332   -0.00187   -0.00491
C1    1    0.793040    0.135385    0.956551    11.00000    0.03815    0.04471 =
         0.05749    0.00769    0.00266    0.00932
C2    1    0.768261    0.143766    1.014606    11.00000    0.04557    0.06348 =
         0.07268    0.02042    0.01427    0.00511
AFIX  43
H2    2    0.731573    0.035526    1.027089    11.00000   -1.20000
AFIX   0
C3    1    0.799254    0.316281    1.053438    11.00000    0.05798    0.06879 =
         0.05016    0.01256    0.01539    0.01460
AFIX  43
H3    2    0.784144    0.321868    1.092969    11.00000   -1.20000
AFIX   0
C4    1    0.852917    0.482708    1.034451    11.00000    0.04848    0.05064 =
         0.04982    0.00100    0.00499    0.01449
 
C5    1    0.876747    0.478246    0.976063    11.00000    0.03834    0.04797 =
         0.04566    0.00123    0.00511    0.00750
AFIX  43
H5    2    0.912255    0.591260    0.963567    11.00000   -1.20000
AFIX   0
C6    1    0.846786    0.301658    0.936025    11.00000    0.03304    0.03671 =
         0.05105    0.00351    0.00205    0.00958
C7    1    0.857813    0.240820    0.873500    11.00000    0.03255    0.04211 =
         0.04806    0.00020   -0.00176    0.00632
C8    1    0.809315    0.036942    0.860125    11.00000    0.03734    0.04843 =
         0.06004   -0.00154   -0.00360    0.00778
C9    1    0.804731   -0.074909    0.804064    11.00000    0.04788    0.05514 =
         0.07708   -0.01147   -0.01243   -0.00284
AFIX  43
H9    2    0.772085   -0.205949    0.796296    11.00000   -1.20000
AFIX   0
C10   1    0.849871    0.013558    0.760262    11.00000    0.06077    0.07031 =
         0.06085   -0.02130   -0.00788    0.00075
AFIX  43
H10   2    0.847598   -0.058594    0.722274    11.00000   -1.20000
AFIX   0
C11   1    0.898403    0.207128    0.771622    11.00000    0.04735    0.06475 =
         0.05438   -0.00919    0.00224    0.00188
AFIX  43
H11   2    0.928962    0.260258    0.741299    11.00000   -1.20000
AFIX   0
C12   1    0.902903    0.324852    0.827062    11.00000    0.03874    0.04461 =
         0.04639   -0.00297   -0.00116    0.00776
C13   1    0.955473    0.536325    0.836102    11.00000    0.04580    0.04825 =
         0.04426    0.00290    0.00598    0.00870
C14   1    1.056408    0.752451    0.798262    11.00000    0.05218    0.06137 =
         0.05867   -0.01141    0.00285   -0.01211
AFIX  23
H14A  2    1.082929    0.734446    0.835725    11.00000   -1.20000
H14B  2    1.031846    0.915793    0.798425    11.00000   -1.20000
AFIX   0
C15   1    1.107147    0.739695    0.747079    11.00000    0.03909    0.04876 =
         0.05040   -0.00894    0.00423   -0.00416
C16   1    1.158322    0.552168    0.744471    11.00000    0.06519    0.05587 =
         0.07700   -0.00236    0.00594    0.00275
AFIX  43
H16   2    1.160331    0.429796    0.774550    11.00000   -1.20000
AFIX   0
C17   1    1.206963    0.540152    0.698367    11.00000    0.06089    0.06454 =
         0.11130   -0.02068    0.01783    0.00464
AFIX  43
H17   2    1.241158    0.410316    0.697241    11.00000   -1.20000
AFIX   0
C18   1    1.204611    0.719835    0.654437    11.00000    0.06431    0.07833 =
         0.08086   -0.02460    0.02637   -0.02446
AFIX  43
H18   2    1.238115    0.715275    0.623730    11.00000   -1.20000
AFIX   0
C19   1    1.153117    0.907188    0.655294    11.00000    0.07239    0.07830 =
         0.07038    0.00248    0.01171   -0.01667
AFIX  43
H19   2    1.150573    1.026723    0.624614    11.00000   -1.20000
AFIX   0
C20   1    1.104866    0.917528    0.702123    11.00000    0.05061    0.05708 =
         0.07034   -0.00324    0.00790    0.00067
AFIX  43
H20   2    1.070462    1.046699    0.703117    11.00000   -1.20000
AFIX   0
C21   1    0.935900    0.813838    1.060818    11.00000    0.06357    0.06860 =
         0.06212   -0.01322   -0.00353    0.00705
AFIX 137
H21A  2    0.976107    0.716446    1.046505    11.00000   -1.50000
H21B  2    0.950984    0.913052    1.094830    11.00000   -1.50000
H21C  2    0.918786    0.925402    1.029691    11.00000   -1.50000
AFIX   0
C22   1    0.720999   -0.234129    0.917034    11.00000    0.04335    0.04562 =
         0.09069    0.00860   -0.00466    0.00075
AFIX  23
H22A  2    0.729937   -0.314358    0.955520    11.00000   -1.20000
H22B  2    0.731200   -0.359291    0.886320    11.00000   -1.20000
AFIX   0
C23   1    0.642547   -0.164032    0.912804    11.00000    0.04004    0.04883 =
         0.07190    0.00403   -0.00551   -0.00022
 
PART -1
C24A  1    0.591067   -0.333983    0.926804    21.00000    0.04165    0.09038 =
         0.11995    0.03575   -0.00770   -0.00002
AFIX  43
H24A  2    0.604346   -0.490498    0.943075    21.00000   -1.20000
AFIX   0
C25A  1    0.518087   -0.279238    0.917308    21.00000    0.04165    0.09038 =
         0.11995    0.03575   -0.00770   -0.00002
AFIX  43
H25A  2    0.482709   -0.397364    0.927259    21.00000   -1.20000
AFIX   0
C26A  1    0.498556   -0.038237    0.891994    21.00000    0.04165    0.09038 =
         0.11995    0.03575   -0.00770   -0.00002
AFIX  43
H26A  2    0.450202    0.007146    0.887328    21.00000   -1.20000
AFIX   0
C27A  1    0.550920    0.120282    0.875195    21.00000    0.04165    0.09038 =
         0.11995    0.03575   -0.00770   -0.00002
AFIX  43
H27A  2    0.538868    0.274372    0.857095    21.00000   -1.20000
AFIX   0
C28A  1    0.622092    0.059202    0.884237    21.00000    0.04165    0.09038 =
         0.11995    0.03575   -0.00770   -0.00002
AFIX  43
H28A  2    0.657621    0.170279    0.870876    21.00000   -1.20000
AFIX   0
PART -2
C24B  1    0.595903   -0.249800    0.959603   -21.00000    0.05623    0.11597 =
         0.09272    0.01788   -0.00157   -0.00208
AFIX  43
H24B  2    0.614630   -0.343973    0.991450   -21.00000   -1.20000
AFIX   0
C25B  1    0.522969   -0.191687    0.957097   -21.00000    0.05623    0.11597 =
         0.09272    0.01788   -0.00157   -0.00208
AFIX  43
H25B  2    0.493430   -0.240002    0.988535   -21.00000   -1.20000
AFIX   0
C26B  1    0.494845   -0.070662    0.911588   -21.00000    0.05623    0.11597 =
         0.09272    0.01788   -0.00157   -0.00208
AFIX  43
H26B  2    0.444853   -0.057674    0.907687   -21.00000   -1.20000
AFIX   0
C27B  1    0.537736    0.036015    0.870060   -21.00000    0.05623    0.11597 =
         0.09272    0.01788   -0.00157   -0.00208
AFIX  43
H27B  2    0.518183    0.140917    0.840489   -21.00000   -1.20000
AFIX   0
C28B  1    0.612619   -0.013903    0.872163   -21.00000    0.05623    0.11597 =
         0.09272    0.01788   -0.00157   -0.00208
AFIX  43
H28B  2    0.642076    0.061957    0.843793   -21.00000   -1.20000
PART 0
 
HKLF 4
 
REM  R2 in P2(1)/n
REM R1 =  0.0550 for   1780 Fo > 4sig(Fo)  and  0.1708 for all   3976 data
REM    288 parameters refined using     30 restraints
 
END  
     
WGHT      0.0647      0.0000 
REM Highest difference peak  0.206,  deepest hole -0.184,  1-sigma level  0.038
Q1    1   0.5015 -0.1007  0.9455  11.00000  0.05    0.21
Q2    1   0.5156 -0.0413  0.9461  11.00000  0.05    0.18
Q3    1   1.1249  0.2836  0.7424  11.00000  0.05    0.17
Q4    1   0.5066  0.0308  0.8894  11.00000  0.05    0.15
Q5    1   0.7655 -0.3895  0.7538  11.00000  0.05    0.14
;

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
O1 O 1.00414(11) 0.5484(4) 0.79199(8) 0.0564(6) Uani 1 1 d . . .
O2 O 0.95629(12) 0.6848(4) 0.87685(9) 0.0618(7) Uani 1 1 d . . .
O3 O 0.87935(13) 0.6459(5) 1.07775(9) 0.0644(7) Uani 1 1 d . . .
N1 N 0.77097(13) -0.0229(5) 0.91057(12) 0.0530(7) Uani 1 1 d . . .
C1 C 0.79304(16) 0.1354(6) 0.95655(14) 0.0468(8) Uani 1 1 d . . .
C2 C 0.76826(17) 0.1438(7) 1.01461(16) 0.0605(9) Uani 1 1 d . . .
H2 H 0.7316 0.0355 1.0271 0.073 Uiso 1 1 calc R . .
C3 C 0.79925(18) 0.3163(7) 1.05344(15) 0.0589(10) Uani 1 1 d . . .
H3 H 0.7841 0.3219 1.0930 0.071 Uiso 1 1 calc R . .
C4 C 0.85292(17) 0.4827(6) 1.03445(14) 0.0496(8) Uani 1 1 d . . .
C5 C 0.87675(15) 0.4782(6) 0.97606(12) 0.0440(8) Uani 1 1 d . . .
H5 H 0.9123 0.5913 0.9636 0.053 Uiso 1 1 calc R . .
C6 C 0.84679(15) 0.3017(5) 0.93603(13) 0.0403(7) Uani 1 1 d . . .
C7 C 0.85781(15) 0.2408(5) 0.87350(13) 0.0409(7) Uani 1 1 d . . .
C8 C 0.80931(16) 0.0369(6) 0.86013(14) 0.0486(8) Uani 1 1 d . . .
C9 C 0.80473(17) -0.0749(6) 0.80406(16) 0.0601(9) Uani 1 1 d . . .
H9 H 0.7721 -0.2059 0.7963 0.072 Uiso 1 1 calc R . .
C10 C 0.84987(19) 0.0136(7) 0.76026(15) 0.0640(10) Uani 1 1 d . . .
H10 H 0.8476 -0.0586 0.7223 0.077 Uiso 1 1 calc R . .
C11 C 0.89840(17) 0.2071(6) 0.77162(14) 0.0555(9) Uani 1 1 d . . .
H11 H 0.9290 0.2603 0.7413 0.067 Uiso 1 1 calc R . .
C12 C 0.90290(15) 0.3249(6) 0.82706(13) 0.0433(8) Uani 1 1 d . . .
C13 C 0.95547(16) 0.5363(6) 0.83610(14) 0.0461(8) Uani 1 1 d . . .
C14 C 1.05641(17) 0.7525(6) 0.79826(13) 0.0574(9) Uani 1 1 d . . .
H14A H 1.0829 0.7344 0.8357 0.069 Uiso 1 1 calc R . .
H14B H 1.0318 0.9158 0.7984 0.069 Uiso 1 1 calc R . .
C15 C 1.10715(16) 0.7397(6) 0.74708(13) 0.0461(8) Uani 1 1 d . . .
C16 C 1.15832(19) 0.5522(7) 0.74447(15) 0.0660(10) Uani 1 1 d . . .
H16 H 1.1603 0.4298 0.7746 0.079 Uiso 1 1 calc R . .
C17 C 1.20696(19) 0.5402(8) 0.69837(19) 0.0788(12) Uani 1 1 d . . .
H17 H 1.2412 0.4103 0.6972 0.095 Uiso 1 1 calc R . .
C18 C 1.2046(2) 0.7198(8) 0.65444(18) 0.0743(12) Uani 1 1 d . . .
H18 H 1.2381 0.7153 0.6237 0.089 Uiso 1 1 calc R . .
C19 C 1.1531(2) 0.9072(8) 0.65529(15) 0.0736(11) Uani 1 1 d . . .
H19 H 1.1506 1.0267 0.6246 0.088 Uiso 1 1 calc R . .
C20 C 1.10487(17) 0.9175(6) 0.70212(15) 0.0593(9) Uani 1 1 d . . .
H20 H 1.0705 1.0467 0.7031 0.071 Uiso 1 1 calc R . .
C21 C 0.93590(18) 0.8138(7) 1.06082(14) 0.0648(10) Uani 1 1 d . . .
H21A H 0.9761 0.7164 1.0465 0.097 Uiso 1 1 calc R . .
H21B H 0.9510 0.9131 1.0948 0.097 Uiso 1 1 calc R . .
H21C H 0.9188 0.9254 1.0297 0.097 Uiso 1 1 calc R . .
C22 C 0.72100(16) -0.2341(6) 0.91703(16) 0.0599(9) Uani 1 1 d . A .
H22A H 0.7299 -0.3144 0.9555 0.072 Uiso 1 1 calc R . .
H22B H 0.7312 -0.3593 0.8863 0.072 Uiso 1 1 calc R . .
C23 C 0.64255(16) -0.1640(6) 0.91280(14) 0.0536(9) Uani 1 1 d D . .
C24A C 0.5911(4) -0.3340(17) 0.9268(4) 0.084(2) Uani 0.527(11) 1 d PD A -1
H24A H 0.6043 -0.4905 0.9431 0.101 Uiso 0.527(11) 1 calc PR A -1
C25A C 0.5181(4) -0.2792(17) 0.9173(5) 0.084(2) Uani 0.527(11) 1 d PD A -1
H25A H 0.4827 -0.3974 0.9273 0.101 Uiso 0.527(11) 1 calc PR A -1
C26A C 0.4986(6) -0.0382(18) 0.8920(4) 0.084(2) Uani 0.527(11) 1 d PD A -1
H26A H 0.4502 0.0071 0.8873 0.101 Uiso 0.527(11) 1 calc PR A -1
C27A C 0.5509(4) 0.120(2) 0.8752(5) 0.084(2) Uani 0.527(11) 1 d PD A -1
H27A H 0.5389 0.2744 0.8571 0.101 Uiso 0.527(11) 1 calc PR A -1
C28A C 0.6221(5) 0.0592(18) 0.8842(5) 0.084(2) Uani 0.527(11) 1 d PD A -1
H28A H 0.6576 0.1703 0.8709 0.101 Uiso 0.527(11) 1 calc PR A -1
C24B C 0.5959(5) -0.2498(19) 0.9596(5) 0.088(2) Uani 0.473(11) 1 d PD A -2
H24B H 0.6146 -0.3440 0.9915 0.106 Uiso 0.473(11) 1 calc PR A -2
C25B C 0.5230(4) -0.1917(19) 0.9571(6) 0.088(2) Uani 0.473(11) 1 d PD A -2
H25B H 0.4934 -0.2400 0.9885 0.106 Uiso 0.473(11) 1 calc PR A -2
C26B C 0.4948(6) -0.071(3) 0.9116(5) 0.088(2) Uani 0.473(11) 1 d PD A -2
H26B H 0.4449 -0.0577 0.9077 0.106 Uiso 0.473(11) 1 calc PR A -2
C27B C 0.5377(6) 0.036(2) 0.8701(5) 0.088(2) Uani 0.473(11) 1 d PD A -2
H27B H 0.5182 0.1409 0.8405 0.106 Uiso 0.473(11) 1 calc PR A -2
C28B C 0.6126(6) -0.014(2) 0.8722(5) 0.088(2) Uani 0.473(11) 1 d PD A -2
H28B H 0.6421 0.0620 0.8438 0.106 Uiso 0.473(11) 1 calc PR A -2


_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
O1 C13 1.344(3) . ?
O1 C14 1.448(3) . ?
O2 C13 1.198(3) . ?
O3 C4 1.377(4) . ?
O3 C21 1.422(4) . ?
N1 C8 1.375(3) . ?
N1 C1 1.379(4) . ?
N1 C22 1.451(4) . ?
C1 C2 1.381(4) . ?
C1 C6 1.403(4) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C6 1.398(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(4) . ?
C7 C12 1.409(4) . ?
C7 C8 1.425(4) . ?
C8 C9 1.385(4) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.487(4) . ?
C14 C15 1.489(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.367(4) . ?
C15 C20 1.371(4) . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.498(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C28B 1.319(11) . ?
C23 C24A 1.344(8) . ?
C23 C28A 1.385(9) . ?
C23 C24B 1.436(9) . ?
C24A C25A 1.394(8) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.430(10) . ?
C25A H25A 0.9300 . ?
C26A C27A 1.334(10) . ?
C26A H26A 0.9300 . ?
C27A C28A 1.367(9) . ?
C27A H27A 0.9300 . ?
C28A H28A 0.9300 . ?
C24B C25B 1.383(9) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.302(10) . ?
C25B H25B 0.9300 . ?
C26B C27B 1.349(11) . ?
C26B H26B 0.9300 . ?
C27B C28B 1.409(11) . ?
C27B H27B 0.9300 . ?
C28B H28B 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
C13 O1 C14 114.6(2) . . ?
C4 O3 C21 117.0(2) . . ?
C8 N1 C1 108.8(3) . . ?
C8 N1 C22 126.2(3) . . ?
C1 N1 C22 124.7(3) . . ?
N1 C1 C2 128.3(3) . . ?
N1 C1 C6 109.6(3) . . ?
C2 C1 C6 122.1(3) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O3 C4 C5 124.0(3) . . ?
O3 C4 C3 115.1(3) . . ?
C5 C4 C3 120.9(3) . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 134.7(3) . . ?
C1 C6 C7 106.6(3) . . ?
C12 C7 C8 117.2(3) . . ?
C12 C7 C6 137.0(3) . . ?
C8 C7 C6 105.8(3) . . ?
N1 C8 C9 128.2(3) . . ?
N1 C8 C7 109.2(3) . . ?
C9 C8 C7 122.6(3) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 121.7(3) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C7 119.3(3) . . ?
C11 C12 C13 119.1(3) . . ?
C7 C12 C13 121.6(3) . . ?
O2 C13 O1 121.6(3) . . ?
O2 C13 C12 126.2(3) . . ?
O1 C13 C12 112.2(3) . . ?
O1 C14 C15 108.5(2) . . ?
O1 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
O1 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C16 C15 C20 118.3(3) . . ?
C16 C15 C14 120.5(3) . . ?
C20 C15 C14 121.2(3) . . ?
C15 C16 C17 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 120.8(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 C23 115.0(3) . . ?
N1 C22 H22A 108.5 . . ?
C23 C22 H22A 108.5 . . ?
N1 C22 H22B 108.5 . . ?
C23 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C28B C23 C24A 105.3(6) . . ?
C24A C23 C28A 118.6(5) . . ?
C28B C23 C24B 116.0(7) . . ?
C28A C23 C24B 116.0(6) . . ?
C28B C23 C22 126.0(6) . . ?
C24A C23 C22 120.7(4) . . ?
C28A C23 C22 119.7(5) . . ?
C24B C23 C22 117.8(5) . . ?
C23 C24A C25A 121.0(7) . . ?
C23 C24A H24A 119.5 . . ?
C25A C24A H24A 119.5 . . ?
C24A C25A C26A 118.8(7) . . ?
C24A C25A H25A 120.6 . . ?
C26A C25A H25A 120.6 . . ?
C27A C26A C25A 118.8(9) . . ?
C27A C26A H26A 120.6 . . ?
C25A C26A H26A 120.6 . . ?
C26A C27A C28A 120.9(9) . . ?
C26A C27A H27A 119.6 . . ?
C28A C27A H27A 119.6 . . ?
C27A C28A C23 121.6(8) . . ?
C27A C28A H28A 119.2 . . ?
C23 C28A H28A 119.2 . . ?
C25B C24B C23 119.7(7) . . ?
C25B C24B H24B 120.2 . . ?
C23 C24B H24B 120.2 . . ?
C26B C25B C24B 121.3(9) . . ?
C26B C25B H25B 119.3 . . ?
C24B C25B H25B 119.3 . . ?
C25B C26B C27B 120.5(11) . . ?
C25B C26B H26B 119.8 . . ?
C27B C26B H26B 119.8 . . ?
C26B C27B C28B 119.0(11) . . ?
C26B C27B H27B 120.5 . . ?
C28B C27B H27B 120.5 . . ?
C23 C28B C27B 122.6(10) . . ?
C23 C28B H28B 118.7 . . ?
C27B C28B H28B 118.7 . . ?

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
C8 N1 C1 C2 179.1(3) . . . . ?
C22 N1 C1 C2 -6.8(5) . . . . ?
C8 N1 C1 C6 -0.1(3) . . . . ?
C22 N1 C1 C6 174.0(2) . . . . ?
N1 C1 C2 C3 179.0(3) . . . . ?
C6 C1 C2 C3 -2.0(5) . . . . ?
C1 C2 C3 C4 1.6(5) . . . . ?
C21 O3 C4 C5 -1.7(4) . . . . ?
C21 O3 C4 C3 178.1(3) . . . . ?
C2 C3 C4 O3 179.9(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
O3 C4 C5 C6 179.1(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
N1 C1 C6 C5 -179.8(2) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
N1 C1 C6 C7 0.2(3) . . . . ?
C2 C1 C6 C7 -179.0(3) . . . . ?
C5 C6 C7 C12 1.7(6) . . . . ?
C1 C6 C7 C12 -178.4(3) . . . . ?
C5 C6 C7 C8 179.7(3) . . . . ?
C1 C6 C7 C8 -0.3(3) . . . . ?
C1 N1 C8 C9 179.6(3) . . . . ?
C22 N1 C8 C9 5.6(5) . . . . ?
C1 N1 C8 C7 -0.1(3) . . . . ?
C22 N1 C8 C7 -174.1(2) . . . . ?
C12 C7 C8 N1 178.8(2) . . . . ?
C6 C7 C8 N1 0.2(3) . . . . ?
C12 C7 C8 C9 -1.0(4) . . . . ?
C6 C7 C8 C9 -179.5(3) . . . . ?
N1 C8 C9 C10 -178.7(3) . . . . ?
C7 C8 C9 C10 1.0(5) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C9 C10 C11 C12 -1.4(5) . . . . ?
C10 C11 C12 C7 1.4(5) . . . . ?
C10 C11 C12 C13 -178.8(3) . . . . ?
C8 C7 C12 C11 -0.3(4) . . . . ?
C6 C7 C12 C11 177.7(3) . . . . ?
C8 C7 C12 C13 180.0(2) . . . . ?
C6 C7 C12 C13 -2.1(5) . . . . ?
C14 O1 C13 O2 0.1(4) . . . . ?
C14 O1 C13 C12 179.5(2) . . . . ?
C11 C12 C13 O2 165.2(3) . . . . ?
C7 C12 C13 O2 -15.0(5) . . . . ?
C11 C12 C13 O1 -14.2(4) . . . . ?
C7 C12 C13 O1 165.6(2) . . . . ?
C13 O1 C14 C15 179.1(2) . . . . ?
O1 C14 C15 C16 -73.2(4) . . . . ?
O1 C14 C15 C20 108.1(3) . . . . ?
C20 C15 C16 C17 0.3(5) . . . . ?
C14 C15 C16 C17 -178.4(3) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
C16 C17 C18 C19 -1.7(6) . . . . ?
C17 C18 C19 C20 2.0(5) . . . . ?
C16 C15 C20 C19 0.1(5) . . . . ?
C14 C15 C20 C19 178.8(3) . . . . ?
C18 C19 C20 C15 -1.2(5) . . . . ?
C8 N1 C22 C23 -101.8(3) . . . . ?
C1 N1 C22 C23 85.1(4) . . . . ?
N1 C22 C23 C28B 45.8(8) . . . . ?
N1 C22 C23 C24A -170.0(6) . . . . ?
N1 C22 C23 C28A 21.7(7) . . . . ?
N1 C22 C23 C24B -128.9(6) . . . . ?
C28B C23 C24A C25A -22.9(9) . . . . ?
C28A C23 C24A C25A -5.1(9) . . . . ?
C24B C23 C24A C25A 90.5(11) . . . . ?
C22 C23 C24A C25A -173.5(5) . . . . ?
C23 C24A C25A C26A 0.3(10) . . . . ?
C24A C25A C26A C27A 3.7(14) . . . . ?
C25A C26A C27A C28A -2.8(16) . . . . ?
C26A C27A C28A C23 -2.2(15) . . . . ?
C28B C23 C28A C27A 61(2) . . . . ?
C24A C23 C28A C27A 6.2(11) . . . . ?
C24B C23 C28A C27A -34.2(11) . . . . ?
C22 C23 C28A C27A 174.7(7) . . . . ?
C28B C23 C24B C25B 5.5(9) . . . . ?
C24A C23 C24B C25B -74.5(10) . . . . ?
C28A C23 C24B C25B 29.0(9) . . . . ?
C22 C23 C24B C25B -179.3(6) . . . . ?
C23 C24B C25B C26B 3.3(13) . . . . ?
C24B C25B C26B C27B -10.3(19) . . . . ?
C25B C26B C27B C28B 8.4(19) . . . . ?
C24A C23 C28B C27B 29.3(11) . . . . ?
C28A C23 C28B C27B -103(3) . . . . ?
C24B C23 C28B C27B -7.4(12) . . . . ?
C22 C23 C28B C27B 177.8(7) . . . . ?
C26B C27B C28B C23 0.9(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 1005568'
#######################################################################
#
#                 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_R6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N O4'
_chemical_formula_sum            'C16 H13 N O4'
_chemical_formula_weight         283.27

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_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

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                   32.374(8)
_cell_length_b                   5.4040(12)
_cell_length_c                   16.122(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.805(9)
_cell_angle_gamma                90.00
_cell_volume                     2560.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    261(2)
_cell_measurement_reflns_used    825
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      20.80

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9707
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      261(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            21895
_diffrn_reflns_av_R_equivalents  0.6463
_diffrn_reflns_av_sigmaI/netI    0.3255
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         27.66
_reflns_number_total             2953
_reflns_number_gt                1072
_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)+(0.0177P)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         2953
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2715
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.1825
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL R6_C in C2/c
CELL 0.71073 32.3736 5.4040 16.1220 90.000 114.805 90.000
ZERR 8.00 0.0080 0.0012 0.0036 0.000 0.009 0.000
LATT 7
SYMM -x, y, -z+1/2
SFAC C H N O
UNIT 128 104 8 32
TEMP -105.950
ACTA
TEMP -12
SIZE 0.28 0.18 0.12
L.S. 12
FMAP 2
PLAN 5
BOND $H
HTAB
CONF
WGHT    0.017700
FVAR       0.06913
N1    3    0.176451    0.629954    0.137972    11.00000    0.01676    0.02575 =
         0.01681    0.00282    0.00233   -0.00218
AFIX  43
H1    2    0.200542    0.591816    0.185723    11.00000   -1.20000
AFIX   0
O1    4    0.028336    0.894132   -0.127945    11.00000    0.06044    0.06892 =
         0.03769   -0.02139   -0.01562    0.04118
O2    4    0.014852    1.242380   -0.072181    11.00000    0.02509    0.05088 =
         0.02789   -0.00342   -0.00045    0.01730
O3    4    0.243586    0.260148    0.176203    11.00000    0.02154    0.03160 =
         0.01941   -0.00130    0.00566    0.00073
O4    4    0.236243    0.000262    0.062046    11.00000    0.02562    0.03188 =
         0.02078    0.00154    0.00497    0.01402
 
C1    1    0.161844    0.514247    0.055274    11.00000    0.01580    0.02763 =
         0.01736    0.00111    0.00714   -0.00367
C2    1    0.121594    0.630001   -0.007350    11.00000    0.01252    0.02403 =
         0.02570   -0.00256    0.00899   -0.00268
C3    1    0.100911    0.538010   -0.096589    11.00000    0.02052    0.03241 =
         0.01538   -0.00019    0.00624   -0.00021
AFIX  43
H3    2    0.074619    0.611369   -0.139383    11.00000   -1.20000
AFIX   0
C4    1    0.120010    0.336691   -0.120456    11.00000    0.02349    0.03789 =
         0.01470    0.00037    0.00587   -0.00065
AFIX  43
H4    2    0.106030    0.274342   -0.179577    11.00000   -1.20000
AFIX   0
C5    1    0.159230    0.226347   -0.058779    11.00000    0.02434    0.02820 =
         0.02395   -0.00247    0.01330    0.00449
AFIX  43
H5    2    0.171009    0.090746   -0.077151    11.00000   -1.20000
AFIX   0
C6    1    0.181793    0.313535    0.030960    11.00000    0.01717    0.02573 =
         0.02025    0.00248    0.00591   -0.00007
C7    1    0.146438    0.818616    0.133127    11.00000    0.01921    0.02321 =
         0.01804    0.00108    0.00727    0.00090
C8    1    0.111054    0.826075    0.043161    11.00000    0.01824    0.02214 =
         0.01921   -0.00123    0.00874   -0.00661
C9    1    0.077592    1.010312    0.025078    11.00000    0.01493    0.02677 =
         0.02443    0.00309    0.00713    0.00279
C10   1    0.080629    1.172279    0.094120    11.00000    0.02186    0.02993 =
         0.02453    0.00033    0.00883   -0.00039
AFIX  43
H10   2    0.058809    1.295615    0.081781    11.00000   -1.20000
AFIX   0
C11   1    0.115920    1.154183    0.182245    11.00000    0.03704    0.02500 =
         0.02969   -0.00746    0.01868   -0.00522
AFIX  43
H11   2    0.116854    1.264136    0.227375    11.00000   -1.20000
AFIX   0
C12   1    0.149016    0.976819    0.202728    11.00000    0.02186    0.03155 =
         0.02120   -0.00234    0.00883   -0.00513
AFIX  43
H12   2    0.172312    0.963223    0.261130    11.00000   -1.20000
AFIX   0
C13   1    0.038844    1.037025   -0.065852    11.00000    0.02136    0.03022 =
         0.02541    0.00383    0.01145    0.00882
C14   1   -0.022892    1.293215   -0.157636    11.00000    0.02323    0.04836 =
         0.03332   -0.00006    0.00915    0.01151
AFIX 137
H14A  2   -0.024524    1.168604   -0.201346    11.00000   -1.50000
H14B  2   -0.018884    1.452557   -0.179551    11.00000   -1.50000
H14C  2   -0.050551    1.292535   -0.149252    11.00000   -1.50000
AFIX   0
C15   1    0.223137    0.192913    0.097219    11.00000    0.01683    0.02507 =
         0.02719    0.00165    0.01131   -0.00046
C16   1    0.275061   -0.135740    0.125111    11.00000    0.02746    0.04089 =
         0.03100    0.00233    0.01139    0.01312
AFIX 137
H16A  2    0.301289   -0.029842    0.147586    11.00000   -1.50000
H16B  2    0.280678   -0.275080    0.094354    11.00000   -1.50000
H16C  2    0.269048   -0.192803    0.175361    11.00000   -1.50000
HKLF   4
 
REM  R6_C in C2/c
REM R1 =  0.0792 for   1072 Fo > 4sig(Fo)  and  0.2715 for all   2953 data
REM    192 parameters refined using      0 restraints
 
END  
     
WGHT      0.0177      0.0000 
REM Highest difference peak  0.337,  deepest hole -0.309,  1-sigma level  0.073
Q1    1   0.1983  0.7988  0.2305  11.00000  0.05    0.34
Q2    1  -0.0340  1.5174 -0.1435  11.00000  0.05    0.30
Q3    1   0.1483 -0.0150 -0.0496  11.00000  0.05    0.28
Q4    1   0.1349  1.1669  0.1906  11.00000  0.05    0.26
Q5    1   0.2129  0.9110  0.3142  11.00000  0.05    0.26
;

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 0.17645(11) 0.6300(6) 0.1380(2) 0.0214(9) Uani 1 1 d . . .
H1 H 0.2005 0.5918 0.1857 0.026 Uiso 1 1 calc R . .
O1 O 0.02834(12) 0.8941(8) -0.1279(3) 0.0680(13) Uani 1 1 d . . .
O2 O 0.01485(9) 1.2424(6) -0.0722(2) 0.0385(10) Uani 1 1 d . . .
O3 O 0.24359(9) 0.2601(5) 0.1762(2) 0.0252(8) Uani 1 1 d . . .
O4 O 0.23624(9) 0.0003(6) 0.0620(2) 0.0277(8) Uani 1 1 d . . .
C1 C 0.16184(13) 0.5142(9) 0.0553(3) 0.0202(11) Uani 1 1 d . . .
C2 C 0.12159(12) 0.6300(8) -0.0073(3) 0.0204(11) Uani 1 1 d . . .
C3 C 0.10091(13) 0.5380(9) -0.0966(3) 0.0232(11) Uani 1 1 d . . .
H3 H 0.0746 0.6114 -0.1394 0.028 Uiso 1 1 calc R . .
C4 C 0.12001(14) 0.3367(9) -0.1205(3) 0.0261(12) Uani 1 1 d . . .
H4 H 0.1060 0.2743 -0.1796 0.031 Uiso 1 1 calc R . .
C5 C 0.15923(13) 0.2263(8) -0.0588(3) 0.0244(12) Uani 1 1 d . . .
H5 H 0.1710 0.0907 -0.0772 0.029 Uiso 1 1 calc R . .
C6 C 0.18179(13) 0.3135(9) 0.0310(3) 0.0217(11) Uani 1 1 d . . .
C7 C 0.14644(13) 0.8186(8) 0.1331(3) 0.0203(11) Uani 1 1 d . . .
C8 C 0.11105(13) 0.8261(8) 0.0432(3) 0.0196(11) Uani 1 1 d . . .
C9 C 0.07759(13) 1.0103(9) 0.0251(3) 0.0224(11) Uani 1 1 d . . .
C10 C 0.08063(14) 1.1723(9) 0.0941(3) 0.0257(12) Uani 1 1 d . . .
H10 H 0.0588 1.2956 0.0818 0.031 Uiso 1 1 calc R . .
C11 C 0.11592(14) 1.1542(9) 0.1822(3) 0.0290(12) Uani 1 1 d . . .
H11 H 0.1169 1.2641 0.2274 0.035 Uiso 1 1 calc R . .
C12 C 0.14902(13) 0.9768(8) 0.2027(3) 0.0249(12) Uani 1 1 d . . .
H12 H 0.1723 0.9632 0.2611 0.030 Uiso 1 1 calc R . .
C13 C 0.03884(14) 1.0370(9) -0.0659(3) 0.0251(12) Uani 1 1 d . . .
C14 C -0.02289(14) 1.2932(9) -0.1576(3) 0.0359(14) Uani 1 1 d . . .
H14A H -0.0245 1.1686 -0.2013 0.054 Uiso 1 1 calc R . .
H14B H -0.0189 1.4526 -0.1796 0.054 Uiso 1 1 calc R . .
H14C H -0.0506 1.2925 -0.1493 0.054 Uiso 1 1 calc R . .
C15 C 0.22314(14) 0.1929(9) 0.0972(3) 0.0223(11) Uani 1 1 d . . .
C16 C 0.27506(14) -0.1357(9) 0.1251(3) 0.0334(13) Uani 1 1 d . . .
H16A H 0.3013 -0.0298 0.1476 0.050 Uiso 1 1 calc R . .
H16B H 0.2807 -0.2751 0.0944 0.050 Uiso 1 1 calc R . .
H16C H 0.2690 -0.1928 0.1754 0.050 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.365(5) . ?
N1 C7 1.388(5) . ?
N1 H1 0.8600 . ?
O1 C13 1.195(5) . ?
O2 C13 1.334(5) . ?
O2 C14 1.433(5) . ?
O3 C15 1.218(5) . ?
O4 C15 1.337(5) . ?
O4 C16 1.443(5) . ?
C1 C6 1.400(6) . ?
C1 C2 1.416(5) . ?
C2 C3 1.399(6) . ?
C2 C8 1.461(6) . ?
C3 C4 1.383(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(6) . ?
C5 H5 0.9300 . ?
C6 C15 1.469(6) . ?
C7 C12 1.385(5) . ?
C7 C8 1.422(6) . ?
C8 C9 1.409(6) . ?
C9 C10 1.387(6) . ?
C9 C13 1.483(6) . ?
C10 C11 1.404(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 N1 C7 109.5(4) . . ?
C1 N1 H1 125.2 . . ?
C7 N1 H1 125.2 . . ?
C13 O2 C14 117.9(4) . . ?
C15 O4 C16 115.8(3) . . ?
N1 C1 C6 128.1(4) . . ?
N1 C1 C2 109.4(4) . . ?
C6 C1 C2 122.5(4) . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 C8 135.1(4) . . ?
C1 C2 C8 106.4(4) . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 116.6(4) . . ?
C1 C6 C15 121.8(4) . . ?
C5 C6 C15 121.5(4) . . ?
C12 C7 N1 127.2(4) . . ?
C12 C7 C8 123.9(4) . . ?
N1 C7 C8 108.9(4) . . ?
C9 C8 C7 116.8(4) . . ?
C9 C8 C2 137.4(4) . . ?
C7 C8 C2 105.7(4) . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 C13 118.5(4) . . ?
C8 C9 C13 122.1(4) . . ?
C9 C10 C11 121.5(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C7 117.5(4) . . ?
C11 C12 H12 121.3 . . ?
C7 C12 H12 121.3 . . ?
O1 C13 O2 121.4(4) . . ?
O1 C13 C9 126.2(4) . . ?
O2 C13 C9 112.4(4) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 123.1(4) . . ?
O3 C15 C6 123.9(4) . . ?
O4 C15 C6 113.1(4) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C6 -179.2(4) . . . . ?
C7 N1 C1 C2 1.1(4) . . . . ?
N1 C1 C2 C3 -179.8(3) . . . . ?
C6 C1 C2 C3 0.6(6) . . . . ?
N1 C1 C2 C8 -1.4(4) . . . . ?
C6 C1 C2 C8 179.0(4) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C8 C2 C3 C4 -177.1(4) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
N1 C1 C6 C5 178.8(4) . . . . ?
C2 C1 C6 C5 -1.7(6) . . . . ?
N1 C1 C6 C15 1.5(6) . . . . ?
C2 C1 C6 C15 -178.9(4) . . . . ?
C4 C5 C6 C1 1.5(6) . . . . ?
C4 C5 C6 C15 178.8(4) . . . . ?
C1 N1 C7 C12 179.2(4) . . . . ?
C1 N1 C7 C8 -0.4(4) . . . . ?
C12 C7 C8 C9 1.4(6) . . . . ?
N1 C7 C8 C9 -179.0(3) . . . . ?
C12 C7 C8 C2 179.9(4) . . . . ?
N1 C7 C8 C2 -0.5(4) . . . . ?
C3 C2 C8 C9 -2.8(9) . . . . ?
C1 C2 C8 C9 179.2(5) . . . . ?
C3 C2 C8 C7 179.1(4) . . . . ?
C1 C2 C8 C7 1.1(4) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C2 C8 C9 C10 -177.8(4) . . . . ?
C7 C8 C9 C13 -179.8(4) . . . . ?
C2 C8 C9 C13 2.3(8) . . . . ?
C8 C9 C10 C11 -1.1(6) . . . . ?
C13 C9 C10 C11 178.7(4) . . . . ?
C9 C10 C11 C12 0.8(7) . . . . ?
C10 C11 C12 C7 0.5(6) . . . . ?
N1 C7 C12 C11 178.8(4) . . . . ?
C8 C7 C12 C11 -1.7(6) . . . . ?
C14 O2 C13 O1 -2.9(7) . . . . ?
C14 O2 C13 C9 178.4(4) . . . . ?
C10 C9 C13 O1 -169.7(5) . . . . ?
C8 C9 C13 O1 10.2(7) . . . . ?
C10 C9 C13 O2 8.9(6) . . . . ?
C8 C9 C13 O2 -171.2(4) . . . . ?
C16 O4 C15 O3 3.6(6) . . . . ?
C16 O4 C15 C6 -176.4(3) . . . . ?
C1 C6 C15 O3 -1.9(6) . . . . ?
C5 C6 C15 O3 -179.1(4) . . . . ?
C1 C6 C15 O4 178.1(4) . . . . ?
C5 C6 C15 O4 0.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 1005569'
#######################################################################
#
#                 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_R7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 N O3'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36

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           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_Int_Tables_number      61

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

_cell_length_a                   12.295(3)
_cell_length_b                   7.7566(16)
_cell_length_c                   33.943(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3237.0(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2370
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      20.93

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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            5311
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_av_sigmaI/netI    0.1161
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2781
_reflns_number_gt                1433
_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)+(0.0520P)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         2781
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_iucr_refine_instruction_details 
;
TITL R7 in Pbca
CELL 0.71073 12.2948 7.7566 33.9425 90.000 90.000 90.000
ZERR 8.00 0.0031 0.0016 0.0078 0.000 0.000 0.000
LATT 1
SYMM x+1/2, -y+1/2, -z
SYMM -x, y+1/2, -z+1/2
SYMM -x+1/2, -y, z+1/2
SFAC C H N O
UNIT 168 136 8 24
SIZE 0.33 0.21 0.14
TEMP -150
ACTA
L.S. 12
OMIT -1 50
OMIT 11 3 2
OMIT 5 4 27
FMAP 2
PLAN 5
BOND $H
CONF
HTAB
WGHT    0.052000
FVAR       0.10949
N1    3    0.700653   -0.164239    0.714364    11.00000    0.03754    0.04424 =
         0.03645   -0.00502   -0.01170    0.00878
AFIX  43
H1    2    0.745318   -0.200252    0.732876    11.00000   -1.20000
AFIX   0
O1    4    0.258535   -0.225949    0.699360    11.00000    0.03578    0.04980 =
         0.03880    0.00553    0.00867   -0.00296
O2    4    0.469640    0.147597    0.611211    11.00000    0.02440    0.05482 =
         0.04217    0.01083    0.01159    0.00532
O3    4    0.592169    0.160241    0.562365    11.00000    0.02705    0.04203 =
         0.03218    0.00696    0.00522    0.00528
C1    1    0.588800   -0.185811    0.714515    11.00000    0.03623    0.03219 =
         0.02925   -0.00744   -0.00408    0.00628
C2    1    0.545414   -0.102761    0.681123    11.00000    0.02833    0.02535 =
         0.02767   -0.00574   -0.00081    0.00095
C3    1    0.431109   -0.110773    0.675078    11.00000    0.03553    0.02967 =
         0.02459    0.00036    0.00299    0.00210
AFIX  43
H3    2    0.397536   -0.052765    0.653637    11.00000   -1.20000
AFIX   0
C4    1    0.371110   -0.205608    0.701432    11.00000    0.03204    0.03693 =
         0.03580   -0.00195    0.00533   -0.00135
C5    1    0.417998   -0.291991    0.733274    11.00000    0.04474    0.03941 =
         0.03047    0.00833    0.00773    0.00069
AFIX  43
H5    2    0.373232   -0.359056    0.750172    11.00000   -1.20000
AFIX   0
C6    1    0.526690   -0.281862    0.740545    11.00000    0.05266    0.04189 =
         0.02491    0.00219    0.00217    0.00834
AFIX  43
H6    2    0.558596   -0.338269    0.762536    11.00000   -1.20000
AFIX   0
C7    1    0.636874   -0.032028    0.659467    11.00000    0.02635    0.02758 =
         0.02679   -0.00537   -0.00307   -0.00177
C8    1    0.730728   -0.078291    0.680969    11.00000    0.03269    0.03153 =
         0.02858   -0.00734   -0.00411   -0.00121
C9    1    0.837622   -0.045168    0.668518    11.00000    0.03105    0.04018 =
         0.04837   -0.01151   -0.01097    0.00212
AFIX  43
H9    2    0.898520   -0.076700    0.684166    11.00000   -1.20000
AFIX   0
C10   1    0.850138    0.034411    0.632907    11.00000    0.02414    0.03630 =
         0.05685   -0.01497    0.00110   -0.00398
AFIX  43
H10   2    0.921327    0.055541    0.623155    11.00000   -1.20000
AFIX   0
C11   1    0.760213    0.085407    0.610513    11.00000    0.03192    0.03164 =
         0.04079   -0.00922    0.00248   -0.00703
AFIX  43
H11   2    0.771626    0.143246    0.586191    11.00000   -1.20000
AFIX   0
C12   1    0.653525    0.053012    0.623183    11.00000    0.02427    0.02773 =
         0.03342   -0.00749   -0.00061   -0.00108
C13   1    0.202484   -0.144151    0.667118    11.00000    0.02870    0.04237 =
         0.04251   -0.00053    0.00206   -0.00261
AFIX 137
H13A  2    0.214180   -0.019286    0.668324    11.00000   -1.50000
H13B  2    0.124471   -0.168750    0.668985    11.00000   -1.50000
H13C  2    0.230669   -0.188771    0.642109    11.00000   -1.50000
AFIX   0
C14   1    0.561585    0.123257    0.599640    11.00000    0.03591    0.02610 =
         0.03116   -0.00095    0.00932   -0.00512
C15   1    0.512837    0.250490    0.538352    11.00000    0.02765    0.03451 =
         0.04228    0.01140    0.00210    0.00288
AFIX  23
H15A  2    0.487293    0.355740    0.552012    11.00000   -1.20000
H15B  2    0.449323    0.175489    0.533094    11.00000   -1.20000
AFIX   0
C16   1    0.568239    0.296587    0.500827    11.00000    0.02042    0.02930 =
         0.03378   -0.00013    0.00107    0.00139
C17   1    0.662125    0.400775    0.501607    11.00000    0.03571    0.03540 =
         0.03640    0.00340    0.00094    0.00450
AFIX  43
H17   2    0.689231    0.440951    0.526156    11.00000   -1.20000
AFIX   0
C18   1    0.715174    0.445256    0.467380    11.00000    0.03069    0.04392 =
         0.07263    0.01632    0.01931    0.00761
AFIX  43
H18   2    0.777788    0.516913    0.468289    11.00000   -1.20000
AFIX   0
C19   1    0.676703    0.384907    0.431631    11.00000    0.07467    0.05112 =
         0.04444    0.01696    0.03106    0.03082
AFIX  43
H19   2    0.713951    0.413375    0.407987    11.00000   -1.20000
AFIX   0
C20   1    0.585967    0.285184    0.430165    11.00000    0.07676    0.04933 =
         0.02990   -0.00600   -0.01099    0.03123
AFIX  43
H20   2    0.559912    0.245333    0.405439    11.00000   -1.20000
AFIX   0
C21   1    0.530261    0.240357    0.464802    11.00000    0.04166    0.03198 =
         0.04376   -0.00302   -0.01069    0.00777
AFIX  43
H21   2    0.466512    0.171409    0.463428    11.00000   -1.20000
HKLF   4
 
REM  R7 in Pbca
REM R1 =  0.0572 for   1433 Fo > 4sig(Fo)  and  0.1491 for all   2781 data
REM    227 parameters refined using      0 restraints
 
END  
     
WGHT      0.0518      0.0000 
REM Highest difference peak  0.170,  deepest hole -0.186,  1-sigma level  0.047
Q1    1   0.4250 -0.1582  0.7357  11.00000  0.05    0.17
Q2    1   0.6341  0.3422  0.4054  11.00000  0.05    0.16
Q3    1   0.6541  0.2539  0.5689  11.00000  0.05    0.16
Q4    1   0.4787 -0.1816  0.7481  11.00000  0.05    0.16
Q5    1   0.6312  0.2773  0.4999  11.00000  0.05    0.15
;

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 0.7007(2) -0.1642(3) 0.71436(7) 0.0394(7) Uani 1 1 d . . .
H1 H 0.7453 -0.2003 0.7329 0.047 Uiso 1 1 calc R . .
O1 O 0.25853(17) -0.2259(3) 0.69936(5) 0.0415(6) Uani 1 1 d . . .
O2 O 0.46964(16) 0.1476(3) 0.61121(5) 0.0405(6) Uani 1 1 d . . .
O3 O 0.59217(15) 0.1602(2) 0.56237(5) 0.0338(5) Uani 1 1 d . . .
C1 C 0.5888(3) -0.1858(4) 0.71451(8) 0.0326(8) Uani 1 1 d . . .
C2 C 0.5454(2) -0.1028(3) 0.68112(8) 0.0271(7) Uani 1 1 d . . .
C3 C 0.4311(2) -0.1108(4) 0.67508(8) 0.0299(7) Uani 1 1 d . . .
H3 H 0.3975 -0.0528 0.6536 0.036 Uiso 1 1 calc R . .
C4 C 0.3711(2) -0.2056(4) 0.70143(8) 0.0349(8) Uani 1 1 d . . .
C5 C 0.4180(3) -0.2920(4) 0.73327(8) 0.0382(8) Uani 1 1 d . . .
H5 H 0.3732 -0.3591 0.7502 0.046 Uiso 1 1 calc R . .
C6 C 0.5267(3) -0.2819(4) 0.74054(8) 0.0398(8) Uani 1 1 d . . .
H6 H 0.5586 -0.3383 0.7625 0.048 Uiso 1 1 calc R . .
C7 C 0.6369(2) -0.0320(4) 0.65947(7) 0.0269(7) Uani 1 1 d . . .
C8 C 0.7307(2) -0.0783(4) 0.68097(8) 0.0309(8) Uani 1 1 d . . .
C9 C 0.8376(2) -0.0452(4) 0.66852(9) 0.0399(8) Uani 1 1 d . . .
H9 H 0.8985 -0.0767 0.6842 0.048 Uiso 1 1 calc R . .
C10 C 0.8501(2) 0.0344(4) 0.63291(9) 0.0391(8) Uani 1 1 d . . .
H10 H 0.9213 0.0555 0.6232 0.047 Uiso 1 1 calc R . .
C11 C 0.7602(2) 0.0854(4) 0.61051(8) 0.0348(8) Uani 1 1 d . . .
H11 H 0.7716 0.1432 0.5862 0.042 Uiso 1 1 calc R . .
C12 C 0.6535(2) 0.0530(4) 0.62318(8) 0.0285(7) Uani 1 1 d . . .
C13 C 0.2025(2) -0.1442(4) 0.66712(8) 0.0379(8) Uani 1 1 d . . .
H13A H 0.2142 -0.0193 0.6683 0.057 Uiso 1 1 calc R . .
H13B H 0.1245 -0.1687 0.6690 0.057 Uiso 1 1 calc R . .
H13C H 0.2307 -0.1888 0.6421 0.057 Uiso 1 1 calc R . .
C14 C 0.5616(3) 0.1233(4) 0.59964(8) 0.0311(8) Uani 1 1 d . . .
C15 C 0.5128(2) 0.2505(4) 0.53835(8) 0.0348(8) Uani 1 1 d . . .
H15A H 0.4873 0.3557 0.5520 0.042 Uiso 1 1 calc R . .
H15B H 0.4493 0.1755 0.5331 0.042 Uiso 1 1 calc R . .
C16 C 0.5682(2) 0.2966(3) 0.50083(8) 0.0278(7) Uani 1 1 d . . .
C17 C 0.6621(2) 0.4008(4) 0.50161(9) 0.0358(8) Uani 1 1 d . . .
H17 H 0.6892 0.4410 0.5262 0.043 Uiso 1 1 calc R . .
C18 C 0.7152(3) 0.4453(4) 0.46738(11) 0.0491(9) Uani 1 1 d . . .
H18 H 0.7778 0.5169 0.4683 0.059 Uiso 1 1 calc R . .
C19 C 0.6767(3) 0.3849(5) 0.43163(10) 0.0567(11) Uani 1 1 d . . .
H19 H 0.7140 0.4134 0.4080 0.068 Uiso 1 1 calc R . .
C20 C 0.5860(3) 0.2852(5) 0.43016(9) 0.0520(10) Uani 1 1 d . . .
H20 H 0.5599 0.2453 0.4054 0.062 Uiso 1 1 calc R . .
C21 C 0.5303(3) 0.2404(4) 0.46480(9) 0.0391(8) Uani 1 1 d . . .
H21 H 0.4665 0.1714 0.4634 0.047 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.366(3) . ?
N1 C1 1.385(4) . ?
N1 H1 0.8800 . ?
O1 C4 1.395(3) . ?
O1 C13 1.441(3) . ?
O2 C14 1.212(3) . ?
O3 C14 1.351(3) . ?
O3 C15 1.451(3) . ?
C1 C6 1.385(4) . ?
C1 C2 1.409(4) . ?
C2 C3 1.422(4) . ?
C2 C7 1.451(4) . ?
C3 C4 1.373(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(4) . ?
C5 C6 1.361(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.412(4) . ?
C7 C12 1.412(4) . ?
C8 C9 1.404(4) . ?
C9 C10 1.366(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.403(4) . ?
C11 H11 0.9500 . ?
C12 C14 1.488(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 C16 1.488(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.380(4) . ?
C16 C17 1.409(4) . ?
C17 C18 1.376(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.358(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.404(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C8 N1 C1 109.3(2) . . ?
C8 N1 H1 125.3 . . ?
C1 N1 H1 125.3 . . ?
C4 O1 C13 117.6(2) . . ?
C14 O3 C15 116.2(2) . . ?
C6 C1 N1 127.9(3) . . ?
C6 C1 C2 123.4(3) . . ?
N1 C1 C2 108.5(3) . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 C7 106.7(2) . . ?
C3 C2 C7 135.2(3) . . ?
C4 C3 C2 117.4(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 O1 124.1(3) . . ?
C3 C4 C5 122.7(3) . . ?
O1 C4 C5 113.2(3) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 117.2(3) . . ?
C5 C6 H6 121.4 . . ?
C1 C6 H6 121.4 . . ?
C8 C7 C12 116.8(3) . . ?
C8 C7 C2 106.0(2) . . ?
C12 C7 C2 137.0(3) . . ?
N1 C8 C9 126.3(3) . . ?
N1 C8 C7 109.4(3) . . ?
C9 C8 C7 124.3(3) . . ?
C10 C9 C8 117.0(3) . . ?
C10 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C7 119.1(3) . . ?
C11 C12 C14 118.7(3) . . ?
C7 C12 C14 122.0(3) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 O3 122.0(3) . . ?
O2 C14 C12 126.3(3) . . ?
O3 C14 C12 111.7(3) . . ?
O3 C15 C16 106.8(2) . . ?
O3 C15 H15A 110.4 . . ?
C16 C15 H15A 110.4 . . ?
O3 C15 H15B 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C21 C16 C17 118.4(3) . . ?
C21 C16 C15 121.9(3) . . ?
C17 C16 C15 119.8(3) . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 119.9(3) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?

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
C8 N1 C1 C6 172.3(3) . . . . ?
C8 N1 C1 C2 -3.2(3) . . . . ?
C6 C1 C2 C3 3.4(4) . . . . ?
N1 C1 C2 C3 179.1(2) . . . . ?
C6 C1 C2 C7 -174.2(3) . . . . ?
N1 C1 C2 C7 1.6(3) . . . . ?
C1 C2 C3 C4 -2.7(4) . . . . ?
C7 C2 C3 C4 174.0(3) . . . . ?
C2 C3 C4 O1 -179.8(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C13 O1 C4 C3 1.0(4) . . . . ?
C13 O1 C4 C5 -179.0(2) . . . . ?
C3 C4 C5 C6 2.1(5) . . . . ?
O1 C4 C5 C6 -177.9(3) . . . . ?
C4 C5 C6 C1 -1.5(4) . . . . ?
N1 C1 C6 C5 -176.1(3) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C1 C2 C7 C8 0.6(3) . . . . ?
C3 C2 C7 C8 -176.4(3) . . . . ?
C1 C2 C7 C12 174.4(3) . . . . ?
C3 C2 C7 C12 -2.5(6) . . . . ?
C1 N1 C8 C9 -174.1(3) . . . . ?
C1 N1 C8 C7 3.6(3) . . . . ?
C12 C7 C8 N1 -177.8(2) . . . . ?
C2 C7 C8 N1 -2.6(3) . . . . ?
C12 C7 C8 C9 0.0(4) . . . . ?
C2 C7 C8 C9 175.3(3) . . . . ?
N1 C8 C9 C10 176.3(3) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
C8 C9 C10 C11 2.0(4) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?
C10 C11 C12 C14 175.0(3) . . . . ?
C8 C7 C12 C11 0.4(4) . . . . ?
C2 C7 C12 C11 -172.9(3) . . . . ?
C8 C7 C12 C14 -174.0(2) . . . . ?
C2 C7 C12 C14 12.6(5) . . . . ?
C15 O3 C14 O2 7.4(4) . . . . ?
C15 O3 C14 C12 -172.2(2) . . . . ?
C11 C12 C14 O2 -158.9(3) . . . . ?
C7 C12 C14 O2 15.6(5) . . . . ?
C11 C12 C14 O3 20.7(4) . . . . ?
C7 C12 C14 O3 -164.9(2) . . . . ?
C14 O3 C15 C16 173.0(2) . . . . ?
O3 C15 C16 C21 121.1(3) . . . . ?
O3 C15 C16 C17 -59.0(3) . . . . ?
C21 C16 C17 C18 -0.2(4) . . . . ?
C15 C16 C17 C18 179.9(3) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C20 1.3(5) . . . . ?
C18 C19 C20 C21 -0.6(5) . . . . ?
C17 C16 C21 C20 0.9(4) . . . . ?
C15 C16 C21 C20 -179.2(3) . . . . ?
C19 C20 C21 C16 -0.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 1005570'
