# Electronic Supplementary Material (ESI) for RSC Advances.
# 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:
#                         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_13

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C31 H29 Cl O P), C2 H3 N, 2(Cl)'
_chemical_formula_sum            'C64 H61 Cl4 N O2 P2'
_chemical_formula_weight         1079.88

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.9199(4)
_cell_length_b                   18.9724(8)
_cell_length_c                   17.1673(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.522(5)
_cell_angle_gamma                90.00
_cell_volume                     2856.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5123
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      32.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1132
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8869
_exptl_absorpt_correction_T_max  0.9411
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 16.1827
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18809
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4816
_reflns_number_gt                3827
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4816
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0975
_refine_ls_wR_factor_ref         0.2852
_refine_ls_wR_factor_gt          0.2709
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_restrained_S_all      1.227
_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
N1S N 0.2819(14) 0.5392(8) -0.1079(10) 0.120(4) Uani 0.50 1 d P . .
C1S C 0.156(4) 0.5164(16) -0.071(2) 0.26(2) Uani 0.50 1 d P . .
C2S C 0.042(2) 0.5059(13) -0.0162(9) 0.126(6) Uani 0.50 1 d P . .
H2S1 H 0.0503 0.4585 0.0038 0.189 Uiso 0.50 1 calc PR . .
H2S2 H -0.0590 0.5140 -0.0449 0.189 Uiso 0.50 1 calc PR . .
H2S3 H 0.0644 0.5384 0.0272 0.189 Uiso 0.50 1 calc PR . .
Cl1 Cl 1.27145(18) 0.85829(9) 0.06286(9) 0.0999(5) Uani 1 1 d . . .
Cl2 Cl -0.29703(10) 0.30169(5) 0.14235(6) 0.0556(4) Uani 1 1 d . . .
P1 P 0.44234(10) 0.54999(5) 0.25516(6) 0.0525(4) Uani 1 1 d . . .
O1 O 0.5405(4) 0.69930(16) 0.2621(3) 0.0864(11) Uani 1 1 d . . .
H1O H 0.6123 0.7240 0.2826 0.130 Uiso 1 1 calc R . .
C1 C 0.7429(6) 0.6779(2) 0.1148(3) 0.0718(12) Uani 1 1 d . . .
H1 H 0.7214 0.6427 0.0724 0.086 Uiso 1 1 calc R . .
C2 C 0.7467(5) 0.6420(2) 0.1945(3) 0.0654(11) Uani 1 1 d . . .
H2A H 0.8199 0.6625 0.2372 0.078 Uiso 1 1 calc R . .
H2B H 0.7588 0.5912 0.1928 0.078 Uiso 1 1 calc R . .
C3 C 0.5758(5) 0.6666(2) 0.1934(3) 0.0665(11) Uani 1 1 d . . .
C4 C 0.5942(6) 0.7160(3) 0.1229(4) 0.0866(16) Uani 1 1 d . . .
H4A H 0.5136 0.7108 0.0770 0.104 Uiso 1 1 calc R . .
H4B H 0.6087 0.7652 0.1379 0.104 Uiso 1 1 calc R . .
C5 C 0.8792(5) 0.7223(2) 0.1033(3) 0.0621(10) Uani 1 1 d . . .
C6 C 0.9466(5) 0.7130(2) 0.0373(3) 0.0650(11) Uani 1 1 d . . .
H6 H 0.9097 0.6777 0.0012 0.078 Uiso 1 1 calc R . .
C7 C 1.0645(5) 0.7535(3) 0.0234(2) 0.0681(11) Uani 1 1 d . . .
H7 H 1.1076 0.7468 -0.0214 0.082 Uiso 1 1 calc R . .
C8 C 1.1182(5) 0.8052(2) 0.0786(3) 0.0641(11) Uani 1 1 d . . .
C9 C 1.0611(6) 0.8150(2) 0.1444(3) 0.0719(12) Uani 1 1 d . . .
H9 H 1.1026 0.8488 0.1813 0.086 Uiso 1 1 calc R . .
C10 C 0.9370(5) 0.7735(2) 0.1568(3) 0.0673(11) Uani 1 1 d . . .
H10 H 0.8940 0.7807 0.2016 0.081 Uiso 1 1 calc R . .
C11 C 0.4593(5) 0.6078(2) 0.1730(3) 0.0682(12) Uani 1 1 d . . .
C12 C 0.3064(6) 0.6237(3) 0.1200(4) 0.104(2) Uani 1 1 d . . .
H12B H 0.2166 0.6002 0.1318 0.125 Uiso 1 1 calc R . .
H12A H 0.2891 0.6712 0.0994 0.125 Uiso 1 1 calc R . .
C13 C 0.4236(6) 0.5790(3) 0.0889(3) 0.0865(16) Uani 1 1 d . . .
H13B H 0.4761 0.5999 0.0498 0.104 Uiso 1 1 calc R . .
H13A H 0.4036 0.5289 0.0822 0.104 Uiso 1 1 calc R . .
C14 C 0.6283(4) 0.5227(2) 0.3088(2) 0.0509(8) Uani 1 1 d . . .
C15 C 0.7103(4) 0.5721(2) 0.3597(2) 0.0586(9) Uani 1 1 d . . .
H15 H 0.6675 0.6156 0.3678 0.070 Uiso 1 1 calc R . .
C16 C 0.8564(5) 0.5555(2) 0.3981(3) 0.0661(11) Uani 1 1 d . . .
H16 H 0.9129 0.5886 0.4311 0.079 Uiso 1 1 calc R . .
C17 C 0.9187(5) 0.4907(3) 0.3881(3) 0.0741(13) Uani 1 1 d . . .
H17 H 1.0171 0.4801 0.4139 0.089 Uiso 1 1 calc R . .
C18 C 0.8350(5) 0.4417(3) 0.3399(3) 0.0704(12) Uani 1 1 d . . .
H18 H 0.8765 0.3975 0.3339 0.084 Uiso 1 1 calc R . .
C19 C 0.6886(5) 0.4575(2) 0.2998(2) 0.0569(9) Uani 1 1 d . . .
H19 H 0.6323 0.4240 0.2672 0.068 Uiso 1 1 calc R . .
C20 C 0.3437(5) 0.5906(2) 0.3272(3) 0.0663(11) Uani 1 1 d . . .
C21 C 0.3695(6) 0.5628(3) 0.4031(4) 0.0892(16) Uani 1 1 d . . .
H21 H 0.4335 0.5240 0.4149 0.107 Uiso 1 1 calc R . .
C22 C 0.2998(7) 0.5927(5) 0.4624(5) 0.118(3) Uani 1 1 d . . .
H22 H 0.3217 0.5762 0.5143 0.142 Uiso 1 1 calc R . .
C23 C 0.1984(9) 0.6469(5) 0.4416(8) 0.147(5) Uani 1 1 d . . .
H23 H 0.1485 0.6665 0.4795 0.176 Uiso 1 1 calc R . .
C24 C 0.1680(8) 0.6741(4) 0.3612(9) 0.131(4) Uani 1 1 d . . .
H24 H 0.0973 0.7099 0.3463 0.157 Uiso 1 1 calc R . .
C25 C 0.2457(6) 0.6458(3) 0.3100(5) 0.099(2) Uani 1 1 d . . .
H25 H 0.2323 0.6648 0.2593 0.119 Uiso 1 1 calc R . .
C26 C 0.3311(4) 0.4735(2) 0.2163(2) 0.0532(9) Uani 1 1 d . . .
C27 C 0.1919(4) 0.4603(2) 0.2376(3) 0.0626(10) Uani 1 1 d . . .
H27 H 0.1551 0.4912 0.2718 0.075 Uiso 1 1 calc R . .
C28 C 0.1076(6) 0.4030(3) 0.2093(3) 0.0817(14) Uani 1 1 d . . .
H28 H 0.0103 0.3968 0.2205 0.098 Uiso 1 1 calc R . .
C29 C 0.1680(6) 0.3535(3) 0.1633(3) 0.0795(14) Uani 1 1 d . . .
H29 H 0.1157 0.3119 0.1482 0.095 Uiso 1 1 calc R . .
C30 C 0.3036(6) 0.3665(2) 0.1408(3) 0.0685(11) Uani 1 1 d . . .
H30 H 0.3402 0.3353 0.1069 0.082 Uiso 1 1 calc R . .
C31 C 0.3881(5) 0.4258(2) 0.1678(2) 0.0578(9) Uani 1 1 d . . .
H31 H 0.4823 0.4336 0.1534 0.069 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
N1S C1S 1.45(5) . ?
C1S C2S 1.52(5) . ?
Cl1 C8 1.758(5) . ?
P1 C11 1.814(4) . ?
P1 C20 1.815(4) . ?
P1 C26 1.815(4) . ?
P1 C14 1.820(4) . ?
O1 C3 1.418(7) . ?
C1 C2 1.522(7) . ?
C1 C5 1.523(6) . ?
C1 C4 1.539(8) . ?
C2 C3 1.592(6) . ?
C3 C11 1.522(6) . ?
C3 C4 1.562(7) . ?
C5 C10 1.370(6) . ?
C5 C6 1.388(7) . ?
C6 C7 1.358(7) . ?
C7 C8 1.387(7) . ?
C8 C9 1.334(7) . ?
C9 C10 1.407(7) . ?
C11 C13 1.522(8) . ?
C11 C12 1.525(6) . ?
C12 C13 1.516(10) . ?
C14 C19 1.369(5) . ?
C14 C15 1.394(6) . ?
C15 C16 1.385(6) . ?
C16 C17 1.372(7) . ?
C17 C18 1.371(7) . ?
C18 C19 1.394(6) . ?
C20 C25 1.362(7) . ?
C20 C21 1.386(8) . ?
C21 C22 1.407(8) . ?
C22 C23 1.373(14) . ?
C23 C24 1.451(14) . ?
C24 C25 1.329(11) . ?
C26 C27 1.379(6) . ?
C26 C31 1.388(6) . ?
C27 C28 1.361(6) . ?
C28 C29 1.397(8) . ?
C29 C30 1.358(7) . ?
C30 C31 1.386(6) . ?

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
N1S C1S C2S 165.2(16) . . ?
C11 P1 C20 113.1(2) . . ?
C11 P1 C26 108.4(2) . . ?
C20 P1 C26 106.80(19) . . ?
C11 P1 C14 111.58(18) . . ?
C20 P1 C14 106.7(2) . . ?
C26 P1 C14 110.19(18) . . ?
C2 C1 C5 118.5(4) . . ?
C2 C1 C4 90.4(4) . . ?
C5 C1 C4 118.2(4) . . ?
C1 C2 C3 89.6(3) . . ?
O1 C3 C11 105.4(4) . . ?
O1 C3 C4 116.9(4) . . ?
C11 C3 C4 115.2(4) . . ?
O1 C3 C2 118.5(4) . . ?
C11 C3 C2 113.6(4) . . ?
C4 C3 C2 87.1(4) . . ?
C1 C4 C3 90.1(3) . . ?
C10 C5 C6 118.2(4) . . ?
C10 C5 C1 121.1(4) . . ?
C6 C5 C1 120.7(4) . . ?
C7 C6 C5 122.3(4) . . ?
C6 C7 C8 117.6(4) . . ?
C9 C8 C7 122.6(4) . . ?
C9 C8 Cl1 118.5(4) . . ?
C7 C8 Cl1 118.8(4) . . ?
C8 C9 C10 118.9(4) . . ?
C5 C10 C9 120.3(4) . . ?
C13 C11 C3 119.8(4) . . ?
C13 C11 C12 59.7(4) . . ?
C3 C11 C12 119.4(4) . . ?
C13 C11 P1 119.2(3) . . ?
C3 C11 P1 114.5(3) . . ?
C12 C11 P1 113.0(3) . . ?
C13 C12 C11 60.1(3) . . ?
C12 C13 C11 60.3(4) . . ?
C19 C14 C15 120.5(4) . . ?
C19 C14 P1 122.7(3) . . ?
C15 C14 P1 116.8(3) . . ?
C16 C15 C14 119.1(4) . . ?
C17 C16 C15 120.8(4) . . ?
C18 C17 C16 119.6(4) . . ?
C17 C18 C19 120.8(4) . . ?
C14 C19 C18 119.3(4) . . ?
C25 C20 C21 119.1(5) . . ?
C25 C20 P1 123.4(5) . . ?
C21 C20 P1 117.4(4) . . ?
C20 C21 C22 120.5(7) . . ?
C23 C22 C21 118.1(8) . . ?
C22 C23 C24 120.9(6) . . ?
C25 C24 C23 117.1(8) . . ?
C24 C25 C20 124.0(9) . . ?
C27 C26 C31 119.2(3) . . ?
C27 C26 P1 120.4(3) . . ?
C31 C26 P1 120.4(3) . . ?
C28 C27 C26 121.0(4) . . ?
C27 C28 C29 119.6(5) . . ?
C30 C29 C28 119.7(4) . . ?
C29 C30 C31 120.7(4) . . ?
C30 C31 C26 119.6(4) . . ?

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
C5 C1 C2 C3 135.3(4) . . . . ?
C4 C1 C2 C3 12.5(4) . . . . ?
C1 C2 C3 O1 -131.5(4) . . . . ?
C1 C2 C3 C11 104.0(4) . . . . ?
C1 C2 C3 C4 -12.3(4) . . . . ?
C2 C1 C4 C3 -12.7(4) . . . . ?
C5 C1 C4 C3 -135.8(4) . . . . ?
O1 C3 C4 C1 132.8(4) . . . . ?
C11 C3 C4 C1 -102.6(4) . . . . ?
C2 C3 C4 C1 12.2(4) . . . . ?
C2 C1 C5 C10 -50.7(6) . . . . ?
C4 C1 C5 C10 56.8(6) . . . . ?
C2 C1 C5 C6 130.5(5) . . . . ?
C4 C1 C5 C6 -122.0(5) . . . . ?
C10 C5 C6 C7 -1.5(7) . . . . ?
C1 C5 C6 C7 177.4(4) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C6 C7 C8 C9 1.6(7) . . . . ?
C6 C7 C8 Cl1 179.6(3) . . . . ?
C7 C8 C9 C10 -2.8(7) . . . . ?
Cl1 C8 C9 C10 179.1(4) . . . . ?
C6 C5 C10 C9 0.1(7) . . . . ?
C1 C5 C10 C9 -178.7(4) . . . . ?
C8 C9 C10 C5 2.0(8) . . . . ?
O1 C3 C11 C13 157.7(4) . . . . ?
C4 C3 C11 C13 27.3(6) . . . . ?
C2 C3 C11 C13 -71.0(5) . . . . ?
O1 C3 C11 C12 87.9(6) . . . . ?
C4 C3 C11 C12 -42.5(7) . . . . ?
C2 C3 C11 C12 -140.8(5) . . . . ?
O1 C3 C11 P1 -50.7(4) . . . . ?
C4 C3 C11 P1 178.9(4) . . . . ?
C2 C3 C11 P1 80.5(5) . . . . ?
C20 P1 C11 C13 -134.6(4) . . . . ?
C26 P1 C11 C13 -16.4(4) . . . . ?
C14 P1 C11 C13 105.1(4) . . . . ?
C20 P1 C11 C3 73.7(4) . . . . ?
C26 P1 C11 C3 -168.1(3) . . . . ?
C14 P1 C11 C3 -46.6(4) . . . . ?
C20 P1 C11 C12 -67.6(5) . . . . ?
C26 P1 C11 C12 50.6(5) . . . . ?
C14 P1 C11 C12 172.1(4) . . . . ?
C3 C11 C12 C13 109.3(5) . . . . ?
P1 C11 C12 C13 -111.4(4) . . . . ?
C3 C11 C13 C12 -108.7(5) . . . . ?
P1 C11 C13 C12 101.1(4) . . . . ?
C11 P1 C14 C19 -102.5(4) . . . . ?
C20 P1 C14 C19 133.5(3) . . . . ?
C26 P1 C14 C19 18.0(4) . . . . ?
C11 P1 C14 C15 76.5(4) . . . . ?
C20 P1 C14 C15 -47.5(4) . . . . ?
C26 P1 C14 C15 -163.0(3) . . . . ?
C19 C14 C15 C16 3.1(6) . . . . ?
P1 C14 C15 C16 -176.0(3) . . . . ?
C14 C15 C16 C17 -1.7(7) . . . . ?
C15 C16 C17 C18 -0.4(7) . . . . ?
C16 C17 C18 C19 1.3(7) . . . . ?
C15 C14 C19 C18 -2.2(6) . . . . ?
P1 C14 C19 C18 176.8(3) . . . . ?
C17 C18 C19 C14 0.1(7) . . . . ?
C11 P1 C20 C25 22.7(5) . . . . ?
C26 P1 C20 C25 -96.5(4) . . . . ?
C14 P1 C20 C25 145.7(4) . . . . ?
C11 P1 C20 C21 -158.1(3) . . . . ?
C26 P1 C20 C21 82.8(4) . . . . ?
C14 P1 C20 C21 -35.0(4) . . . . ?
C25 C20 C21 C22 -2.3(7) . . . . ?
P1 C20 C21 C22 178.4(4) . . . . ?
C20 C21 C22 C23 4.2(8) . . . . ?
C21 C22 C23 C24 -2.0(10) . . . . ?
C22 C23 C24 C25 -2.0(10) . . . . ?
C23 C24 C25 C20 4.1(9) . . . . ?
C21 C20 C25 C24 -2.1(8) . . . . ?
P1 C20 C25 C24 177.1(5) . . . . ?
C11 P1 C26 C27 -116.3(3) . . . . ?
C20 P1 C26 C27 5.9(4) . . . . ?
C14 P1 C26 C27 121.4(3) . . . . ?
C11 P1 C26 C31 66.7(4) . . . . ?
C20 P1 C26 C31 -171.2(3) . . . . ?
C14 P1 C26 C31 -55.7(4) . . . . ?
C31 C26 C27 C28 -2.5(6) . . . . ?
P1 C26 C27 C28 -179.6(4) . . . . ?
C26 C27 C28 C29 5.3(7) . . . . ?
C27 C28 C29 C30 -6.4(8) . . . . ?
C28 C29 C30 C31 4.8(8) . . . . ?
C29 C30 C31 C26 -2.0(7) . . . . ?
C27 C26 C31 C30 0.8(6) . . . . ?
P1 C26 C31 C30 177.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         2.156
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.114
_database_code_depnum_ccdc_archive 'CCDC 962474'
#######################################################################
#
#                 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_18a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36

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_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.0940(5)
_cell_length_b                   15.4178(15)
_cell_length_c                   17.637(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1657.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    710
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      31.89

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 16.1827
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8425
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_sigmaI/netI    0.1443
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4455
_reflns_number_gt                1524
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'

_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)+(0.0089P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(12)
_refine_ls_number_reflns         4455
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2135
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0471
_refine_ls_goodness_of_fit_ref   0.793
_refine_ls_restrained_S_all      0.793
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7596(3) 0.44496(14) 0.34992(11) 0.0816(6) Uani 1 1 d . . .
O2 O 0.8187(3) 0.32122(12) 0.29582(11) 0.0917(7) Uani 1 1 d . . .
O3 O 0.4243(3) 0.02803(12) 0.33771(11) 0.0917(7) Uani 1 1 d . . .
O4 O 0.1057(3) 0.04114(12) 0.39492(11) 0.0909(6) Uani 1 1 d . . .
N1 N 0.3231(3) 0.40801(14) 0.37353(12) 0.0520(6) Uani 1 1 d . . .
H1N H 0.181(3) 0.4018(12) 0.3662(11) 0.049(7) Uiso 1 1 d . . .
C1 C 0.3790(3) 0.49816(16) 0.35623(13) 0.0533(7) Uani 1 1 d . . .
H1 H 0.3699 0.5078 0.3014 0.064 Uiso 1 1 calc R . .
C2 C 0.6124(4) 0.50846(16) 0.38208(15) 0.0740(8) Uani 1 1 d . . .
H2B H 0.6632 0.5660 0.3684 0.089 Uiso 1 1 calc R . .
H2A H 0.6172 0.5039 0.4369 0.089 Uiso 1 1 calc R . .
C3 C 0.6852(4) 0.36971(19) 0.32394(16) 0.0630(8) Uani 1 1 d . . .
C4 C 0.4454(3) 0.34831(16) 0.32612(13) 0.0462(6) Uani 1 1 d . . .
C5 C 0.3590(3) 0.32808(15) 0.24499(13) 0.0610(7) Uani 1 1 d . . .
H5B H 0.2109 0.3487 0.2359 0.073 Uiso 1 1 calc R . .
H5A H 0.4573 0.3469 0.2050 0.073 Uiso 1 1 calc R . .
C6 C 0.3719(4) 0.23120(15) 0.26158(13) 0.0667(7) Uani 1 1 d . . .
H6B H 0.4952 0.2026 0.2375 0.080 Uiso 1 1 calc R . .
H6A H 0.2362 0.2004 0.2516 0.080 Uiso 1 1 calc R . .
C7 C 0.4091(3) 0.25129(14) 0.34549(13) 0.0456(6) Uani 1 1 d . . .
C8 C 0.5659(4) 0.19455(15) 0.39201(14) 0.0648(7) Uani 1 1 d . . .
H8B H 0.6483 0.2263 0.4300 0.078 Uiso 1 1 calc R . .
H8A H 0.6621 0.1587 0.3614 0.078 Uiso 1 1 calc R . .
C9 C 0.3661(4) 0.14603(16) 0.42381(13) 0.0641(7) Uani 1 1 d . . .
H9 H 0.3724 0.1368 0.4787 0.077 Uiso 1 1 calc R . .
C10 C 0.2235(4) 0.22497(16) 0.40017(14) 0.0708(8) Uani 1 1 d . . .
H10B H 0.0875 0.2094 0.3751 0.085 Uiso 1 1 calc R . .
H10A H 0.1978 0.2663 0.4407 0.085 Uiso 1 1 calc R . .
C11 C 0.3087(5) 0.06603(17) 0.37981(16) 0.0617(8) Uani 1 1 d . . .
C12 C 0.0257(4) -0.03199(17) 0.35286(16) 0.1168(13) Uani 1 1 d . . .
H12C H -0.1285 -0.0390 0.3621 0.175 Uiso 1 1 calc R . .
H12B H 0.1022 -0.0833 0.3686 0.175 Uiso 1 1 calc R . .
H12A H 0.0497 -0.0225 0.2997 0.175 Uiso 1 1 calc R . .
C13 C 0.2327(4) 0.56138(17) 0.39673(16) 0.0527(7) Uani 1 1 d . . .
C14 C 0.1836(4) 0.55165(16) 0.47186(16) 0.0649(8) Uani 1 1 d . . .
H14 H 0.2364 0.5035 0.4979 0.078 Uiso 1 1 calc R . .
C15 C 0.0577(4) 0.6117(2) 0.50983(16) 0.0783(9) Uani 1 1 d . . .
H15 H 0.0239 0.6034 0.5607 0.094 Uiso 1 1 calc R . .
C16 C -0.0176(4) 0.68358(19) 0.4728(2) 0.0805(10) Uani 1 1 d . . .
H16 H -0.0999 0.7247 0.4989 0.097 Uiso 1 1 calc R . .
C17 C 0.0271(4) 0.69538(18) 0.3978(2) 0.0771(9) Uani 1 1 d . . .
H17 H -0.0251 0.7441 0.3725 0.093 Uiso 1 1 calc R . .
C18 C 0.1514(4) 0.63388(18) 0.35948(14) 0.0645(8) Uani 1 1 d . . .
H18 H 0.1806 0.6414 0.3081 0.077 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
O1 C3 1.327(3) . ?
O1 C2 1.444(2) . ?
O2 C3 1.211(3) . ?
O3 C11 1.180(3) . ?
O4 C11 1.322(3) . ?
O4 C12 1.435(2) . ?
N1 C4 1.450(3) . ?
N1 C1 1.463(3) . ?
C1 C13 1.502(3) . ?
C1 C2 1.502(3) . ?
C3 C4 1.499(3) . ?
C4 C7 1.550(3) . ?
C4 C5 1.556(3) . ?
C5 C6 1.524(3) . ?
C6 C7 1.529(3) . ?
C7 C8 1.534(3) . ?
C7 C10 1.541(3) . ?
C8 C9 1.535(3) . ?
C9 C11 1.499(3) . ?
C9 C10 1.553(3) . ?
C13 C14 1.367(3) . ?
C13 C18 1.388(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.366(3) . ?
C16 C17 1.362(3) . ?
C17 C18 1.389(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 121.08(19) . . ?
C11 O4 C12 116.2(2) . . ?
C4 N1 C1 111.30(19) . . ?
N1 C1 C13 112.29(19) . . ?
N1 C1 C2 104.9(2) . . ?
C13 C1 C2 110.4(2) . . ?
O1 C2 C1 113.4(2) . . ?
O2 C3 O1 116.8(2) . . ?
O2 C3 C4 122.0(3) . . ?
O1 C3 C4 121.1(2) . . ?
N1 C4 C3 112.1(2) . . ?
N1 C4 C7 114.33(18) . . ?
C3 C4 C7 110.9(2) . . ?
N1 C4 C5 118.92(19) . . ?
C3 C4 C5 110.5(2) . . ?
C7 C4 C5 87.76(16) . . ?
C6 C5 C4 90.15(17) . . ?
C5 C6 C7 89.71(17) . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 C10 116.34(19) . . ?
C8 C7 C10 88.42(17) . . ?
C6 C7 C4 90.19(17) . . ?
C8 C7 C4 125.40(18) . . ?
C10 C7 C4 119.79(19) . . ?
C7 C8 C9 88.80(16) . . ?
C11 C9 C8 113.4(2) . . ?
C11 C9 C10 112.0(2) . . ?
C8 C9 C10 87.94(17) . . ?
C7 C10 C9 87.91(17) . . ?
O3 C11 O4 122.8(3) . . ?
O3 C11 C9 126.5(3) . . ?
O4 C11 C9 110.7(3) . . ?
C14 C13 C18 118.0(2) . . ?
C14 C13 C1 121.3(3) . . ?
C18 C13 C1 120.6(3) . . ?
C13 C14 C15 121.3(3) . . ?
C16 C15 C14 120.0(3) . . ?
C17 C16 C15 120.4(3) . . ?
C16 C17 C18 119.3(3) . . ?
C13 C18 C17 120.9(3) . . ?

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
C4 N1 C1 C13 172.08(19) . . . . ?
C4 N1 C1 C2 -67.9(2) . . . . ?
C3 O1 C2 C1 -22.6(3) . . . . ?
N1 C1 C2 O1 54.1(3) . . . . ?
C13 C1 C2 O1 175.3(2) . . . . ?
C2 O1 C3 O2 177.9(2) . . . . ?
C2 O1 C3 C4 0.8(3) . . . . ?
C1 N1 C4 C3 48.0(3) . . . . ?
C1 N1 C4 C7 175.34(18) . . . . ?
C1 N1 C4 C5 -83.1(2) . . . . ?
O2 C3 C4 N1 170.1(2) . . . . ?
O1 C3 C4 N1 -13.0(3) . . . . ?
O2 C3 C4 C7 40.9(3) . . . . ?
O1 C3 C4 C7 -142.2(2) . . . . ?
O2 C3 C4 C5 -54.8(3) . . . . ?
O1 C3 C4 C5 122.2(3) . . . . ?
N1 C4 C5 C6 -127.8(2) . . . . ?
C3 C4 C5 C6 100.4(2) . . . . ?
C7 C4 C5 C6 -11.11(16) . . . . ?
C4 C5 C6 C7 11.26(16) . . . . ?
C5 C6 C7 C8 -143.2(2) . . . . ?
C5 C6 C7 C10 112.5(2) . . . . ?
C5 C6 C7 C4 -11.30(16) . . . . ?
N1 C4 C7 C6 132.0(2) . . . . ?
C3 C4 C7 C6 -100.1(2) . . . . ?
C5 C4 C7 C6 11.07(16) . . . . ?
N1 C4 C7 C8 -100.5(3) . . . . ?
C3 C4 C7 C8 27.5(3) . . . . ?
C5 C4 C7 C8 138.6(2) . . . . ?
N1 C4 C7 C10 11.1(3) . . . . ?
C3 C4 C7 C10 139.1(2) . . . . ?
C5 C4 C7 C10 -109.8(2) . . . . ?
C6 C7 C8 C9 -99.8(2) . . . . ?
C10 C7 C8 C9 19.89(17) . . . . ?
C4 C7 C8 C9 146.1(2) . . . . ?
C7 C8 C9 C11 93.4(2) . . . . ?
C7 C8 C9 C10 -19.73(18) . . . . ?
C6 C7 C10 C9 102.9(2) . . . . ?
C8 C7 C10 C9 -19.66(17) . . . . ?
C4 C7 C10 C9 -150.4(2) . . . . ?
C11 C9 C10 C7 -94.8(2) . . . . ?
C8 C9 C10 C7 19.65(17) . . . . ?
C12 O4 C11 O3 -4.4(4) . . . . ?
C12 O4 C11 C9 176.4(2) . . . . ?
C8 C9 C11 O3 18.8(4) . . . . ?
C10 C9 C11 O3 116.4(3) . . . . ?
C8 C9 C11 O4 -162.0(2) . . . . ?
C10 C9 C11 O4 -64.4(3) . . . . ?
N1 C1 C13 C14 45.5(3) . . . . ?
C2 C1 C13 C14 -71.3(3) . . . . ?
N1 C1 C13 C18 -137.6(2) . . . . ?
C2 C1 C13 C18 105.7(3) . . . . ?
C18 C13 C14 C15 -0.1(4) . . . . ?
C1 C13 C14 C15 177.0(2) . . . . ?
C13 C14 C15 C16 -1.2(4) . . . . ?
C14 C15 C16 C17 1.4(4) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
C1 C13 C18 C17 -176.0(2) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.025
_database_code_depnum_ccdc_archive 'CCDC 962475'
#######################################################################
#
#                 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_18b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36

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_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.1255(6)
_cell_length_b                   11.2180(11)
_cell_length_c                   24.188(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1662.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1184
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      32.05

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 16.1827
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13556
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_sigmaI/netI    0.1379
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         29.99
_reflns_number_total             4755
_reflns_number_gt                1883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'

_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)+(0.0179P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(13)
_refine_ls_number_reflns         4755
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1945
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_restrained_S_all      0.840
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1688(2) 0.70322(14) 0.20416(6) 0.0565(5) Uani 1 1 d . . .
O2 O -0.2074(3) 0.60287(15) 0.28062(7) 0.0685(5) Uani 1 1 d . . .
O3 O 0.1843(4) 0.8793(2) 0.44372(8) 0.1178(9) Uani 1 1 d . . .
O4 O 0.5285(3) 0.89456(16) 0.42053(7) 0.0814(6) Uani 1 1 d . . .
N1 N 0.2796(3) 0.67458(17) 0.20801(8) 0.0466(5) Uani 1 1 d . . .
H1N H 0.422(3) 0.6826(16) 0.2144(7) 0.041(6) Uiso 1 1 d . . .
C1 C 0.1943(3) 0.7747(2) 0.17600(8) 0.0439(6) Uani 1 1 d . . .
H1 H 0.1866 0.8460 0.1993 0.053 Uiso 1 1 calc R . .
C2 C -0.0321(4) 0.7385(2) 0.15826(8) 0.0528(7) Uani 1 1 d . . .
H2B H -0.1004 0.8047 0.1391 0.063 Uiso 1 1 calc R . .
H2A H -0.0212 0.6726 0.1324 0.063 Uiso 1 1 calc R . .
C3 C -0.0819(4) 0.6490(2) 0.24878(10) 0.0467(6) Uani 1 1 d . . .
C4 C 0.1606(3) 0.65663(19) 0.25889(9) 0.0398(6) Uani 1 1 d . . .
C5 C 0.2443(4) 0.55391(19) 0.29494(9) 0.0560(7) Uani 1 1 d . . .
H5B H 0.1511 0.4840 0.2942 0.067 Uiso 1 1 calc R . .
H5A H 0.3950 0.5325 0.2876 0.067 Uiso 1 1 calc R . .
C6 C 0.2148(4) 0.6308(2) 0.34667(9) 0.0626(7) Uani 1 1 d . . .
H6B H 0.3402 0.6304 0.3712 0.075 Uiso 1 1 calc R . .
H6A H 0.0814 0.6142 0.3669 0.075 Uiso 1 1 calc R . .
C7 C 0.2010(3) 0.74148(18) 0.30976(8) 0.0411(5) Uani 1 1 d . . .
C8 C 0.0626(4) 0.8484(2) 0.32893(9) 0.0535(6) Uani 1 1 d . . .
H8B H -0.0389 0.8298 0.3585 0.064 Uiso 1 1 calc R . .
H8A H -0.0094 0.8907 0.2991 0.064 Uiso 1 1 calc R . .
C9 C 0.2772(4) 0.90772(19) 0.34883(9) 0.0533(7) Uani 1 1 d . . .
H9 H 0.2891 0.9911 0.3371 0.064 Uiso 1 1 calc R . .
C10 C 0.4037(4) 0.8225(2) 0.31087(9) 0.0546(7) Uani 1 1 d . . .
H10B H 0.5303 0.7864 0.3282 0.065 Uiso 1 1 calc R . .
H10A H 0.4408 0.8565 0.2752 0.065 Uiso 1 1 calc R . .
C11 C 0.3187(6) 0.8923(2) 0.40860(11) 0.0639(7) Uani 1 1 d . . .
C12 C 0.5913(5) 0.8797(3) 0.47786(10) 0.1057(11) Uani 1 1 d . . .
H12C H 0.5208 0.9395 0.5000 0.159 Uiso 1 1 calc R . .
H12B H 0.7467 0.8877 0.4812 0.159 Uiso 1 1 calc R . .
H12A H 0.5478 0.8020 0.4904 0.159 Uiso 1 1 calc R . .
C13 C 0.3293(4) 0.8004(2) 0.12512(9) 0.0448(6) Uani 1 1 d . . .
C14 C 0.3428(4) 0.9156(2) 0.10532(9) 0.0619(8) Uani 1 1 d . . .
H14 H 0.2778 0.9772 0.1251 0.074 Uiso 1 1 calc R . .
C15 C 0.4515(5) 0.9409(3) 0.05654(11) 0.0785(9) Uani 1 1 d . . .
H15 H 0.4555 1.0184 0.0429 0.094 Uiso 1 1 calc R . .
C16 C 0.5538(5) 0.8498(3) 0.02849(11) 0.0801(9) Uani 1 1 d . . .
H16 H 0.6285 0.8661 -0.0041 0.096 Uiso 1 1 calc R . .
C17 C 0.5463(5) 0.7370(3) 0.04796(10) 0.0752(8) Uani 1 1 d . . .
H17 H 0.6180 0.6762 0.0291 0.090 Uiso 1 1 calc R . .
C18 C 0.4315(4) 0.7116(2) 0.09617(9) 0.0602(7) Uani 1 1 d . . .
H18 H 0.4240 0.6334 0.1089 0.072 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
O1 C3 1.348(2) . ?
O1 C2 1.446(2) . ?
O2 C3 1.205(2) . ?
O3 C11 1.192(3) . ?
O4 C11 1.318(3) . ?
O4 C12 1.449(2) . ?
N1 C4 1.445(2) . ?
N1 C1 1.461(2) . ?
C1 C2 1.507(3) . ?
C1 C13 1.511(3) . ?
C3 C4 1.508(3) . ?
C4 C5 1.533(3) . ?
C4 C7 1.575(3) . ?
C5 C6 1.530(3) . ?
C6 C7 1.531(3) . ?
C7 C10 1.539(3) . ?
C7 C8 1.540(3) . ?
C8 C9 1.550(3) . ?
C9 C11 1.478(3) . ?
C9 C10 1.535(3) . ?
C13 C18 1.369(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.351(3) . ?
C17 C18 1.392(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 120.62(17) . . ?
C11 O4 C12 117.8(2) . . ?
C4 N1 C1 112.21(17) . . ?
N1 C1 C2 105.80(19) . . ?
N1 C1 C13 112.49(18) . . ?
C2 C1 C13 108.87(17) . . ?
O1 C2 C1 112.84(17) . . ?
O2 C3 O1 117.0(2) . . ?
O2 C3 C4 123.3(2) . . ?
O1 C3 C4 119.6(2) . . ?
N1 C4 C3 111.53(19) . . ?
N1 C4 C5 114.86(18) . . ?
C3 C4 C5 112.28(19) . . ?
N1 C4 C7 120.12(17) . . ?
C3 C4 C7 108.41(17) . . ?
C5 C4 C7 87.55(15) . . ?
C6 C5 C4 90.10(16) . . ?
C5 C6 C7 89.25(16) . . ?
C6 C7 C10 115.12(19) . . ?
C6 C7 C8 119.08(18) . . ?
C10 C7 C8 88.77(16) . . ?
C6 C7 C4 88.52(16) . . ?
C10 C7 C4 119.84(17) . . ?
C8 C7 C4 128.26(17) . . ?
C7 C8 C9 87.77(16) . . ?
C11 C9 C10 115.2(2) . . ?
C11 C9 C8 113.6(2) . . ?
C10 C9 C8 88.57(16) . . ?
C9 C10 C7 88.34(17) . . ?
O3 C11 O4 121.3(3) . . ?
O3 C11 C9 126.3(3) . . ?
O4 C11 C9 112.3(3) . . ?
C18 C13 C14 118.5(2) . . ?
C18 C13 C1 121.8(2) . . ?
C14 C13 C1 119.6(2) . . ?
C13 C14 C15 121.1(2) . . ?
C16 C15 C14 119.1(3) . . ?
C17 C16 C15 120.5(3) . . ?
C16 C17 C18 120.1(3) . . ?
C13 C18 C17 120.7(3) . . ?

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
C4 N1 C1 C2 -66.0(2) . . . . ?
C4 N1 C1 C13 175.26(17) . . . . ?
C3 O1 C2 C1 -32.8(3) . . . . ?
N1 C1 C2 O1 54.4(2) . . . . ?
C13 C1 C2 O1 175.57(18) . . . . ?
C2 O1 C3 O2 -166.82(19) . . . . ?
C2 O1 C3 C4 17.8(3) . . . . ?
C1 N1 C4 C3 51.7(2) . . . . ?
C1 N1 C4 C5 -179.09(18) . . . . ?
C1 N1 C4 C7 -76.7(2) . . . . ?
O2 C3 C4 N1 158.8(2) . . . . ?
O1 C3 C4 N1 -26.1(3) . . . . ?
O2 C3 C4 C5 28.3(3) . . . . ?
O1 C3 C4 C5 -156.66(19) . . . . ?
O2 C3 C4 C7 -66.8(3) . . . . ?
O1 C3 C4 C7 108.3(2) . . . . ?
N1 C4 C5 C6 138.24(19) . . . . ?
C3 C4 C5 C6 -92.9(2) . . . . ?
C7 C4 C5 C6 15.97(17) . . . . ?
C4 C5 C6 C7 -16.43(17) . . . . ?
C5 C6 C7 C10 -106.5(2) . . . . ?
C5 C6 C7 C8 149.96(19) . . . . ?
C5 C6 C7 C4 15.98(17) . . . . ?
N1 C4 C7 C6 -133.5(2) . . . . ?
C3 C4 C7 C6 96.7(2) . . . . ?
C5 C4 C7 C6 -15.97(17) . . . . ?
N1 C4 C7 C10 -15.1(3) . . . . ?
C3 C4 C7 C10 -144.9(2) . . . . ?
C5 C4 C7 C10 102.4(2) . . . . ?
N1 C4 C7 C8 99.7(3) . . . . ?
C3 C4 C7 C8 -30.1(3) . . . . ?
C5 C4 C7 C8 -142.8(2) . . . . ?
C6 C7 C8 C9 99.2(2) . . . . ?
C10 C7 C8 C9 -19.11(16) . . . . ?
C4 C7 C8 C9 -147.2(2) . . . . ?
C7 C8 C9 C11 -97.8(2) . . . . ?
C7 C8 C9 C10 19.16(16) . . . . ?
C11 C9 C10 C7 96.3(2) . . . . ?
C8 C9 C10 C7 -19.17(16) . . . . ?
C6 C7 C10 C9 -102.5(2) . . . . ?
C8 C7 C10 C9 19.29(16) . . . . ?
C4 C7 C10 C9 153.85(18) . . . . ?
C12 O4 C11 O3 0.5(4) . . . . ?
C12 O4 C11 C9 -179.7(2) . . . . ?
C10 C9 C11 O3 -127.8(3) . . . . ?
C8 C9 C11 O3 -27.7(4) . . . . ?
C10 C9 C11 O4 52.4(3) . . . . ?
C8 C9 C11 O4 152.4(2) . . . . ?
N1 C1 C13 C18 33.5(3) . . . . ?
C2 C1 C13 C18 -83.4(3) . . . . ?
N1 C1 C13 C14 -149.6(2) . . . . ?
C2 C1 C13 C14 93.4(2) . . . . ?
C18 C13 C14 C15 1.8(4) . . . . ?
C1 C13 C14 C15 -175.1(2) . . . . ?
C13 C14 C15 C16 -2.2(4) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
C1 C13 C18 C17 176.9(2) . . . . ?
C16 C17 C18 C13 -1.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 962476'
#######################################################################
#
#                 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_18c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.260(3)
_cell_length_b                   5.820(2)
_cell_length_c                   14.060(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.37(3)
_cell_angle_gamma                90.00
_cell_volume                     830.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    302
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      17.63

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 16.1827
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7180
_diffrn_reflns_av_R_equivalents  0.1552
_diffrn_reflns_av_sigmaI/netI    0.4140
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4370
_reflns_number_gt                836
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'

_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5(4)
_refine_ls_number_reflns         4370
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.3881
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   0.696
_refine_ls_restrained_S_all      0.696
_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
O1 O 0.6774(5) -0.0663(8) 0.1019(3) 0.0849(13) Uani 1 1 d . . .
O2 O 0.4630(4) -0.1055(9) 0.0675(3) 0.0919(14) Uani 1 1 d . . .
O3 O 0.8193(7) 0.0443(14) 0.4550(5) 0.189(3) Uani 1 1 d . . .
O4 O 0.7127(5) -0.2478(11) 0.4987(4) 0.1131(18) Uani 1 1 d . . .
N1 N 0.6469(6) 0.3909(10) 0.1618(4) 0.0685(16) Uani 1 1 d . . .
H1N H 0.614(6) 0.499(13) 0.138(5) 0.082 Uiso 1 1 d . . .
C1 C 0.7637(6) 0.3184(11) 0.1220(4) 0.0668(18) Uani 1 1 d . . .
H1 H 0.7490 0.3351 0.0519 0.080 Uiso 1 1 calc R . .
C2 C 0.7856(6) 0.0708(11) 0.1487(5) 0.079(2) Uani 1 1 d . . .
H2A H 0.8674 0.0183 0.1292 0.095 Uiso 1 1 calc R . .
H2B H 0.7923 0.0534 0.2178 0.095 Uiso 1 1 calc R . .
C3 C 0.5554(7) 0.0050(12) 0.1029(5) 0.0699(19) Uani 1 1 d . . .
C4 C 0.5396(5) 0.2227(12) 0.1629(4) 0.0646(17) Uani 1 1 d . . .
C5 C 0.4012(5) 0.3282(12) 0.1435(4) 0.081(2) Uani 1 1 d . . .
H5A H 0.3512 0.2794 0.0830 0.098 Uiso 1 1 calc R . .
H5B H 0.4011 0.4943 0.1488 0.098 Uiso 1 1 calc R . .
C6 C 0.3589(6) 0.2041(15) 0.2326(5) 0.107(3) Uani 1 1 d . . .
H6A H 0.3219 0.3055 0.2765 0.128 Uiso 1 1 calc R . .
H6B H 0.3036 0.0703 0.2168 0.128 Uiso 1 1 calc R . .
C7 C 0.5067(6) 0.1476(12) 0.2633(4) 0.0670(19) Uani 1 1 d . . .
C8 C 0.5780(6) 0.2538(13) 0.3564(4) 0.086(2) Uani 1 1 d . . .
H8A H 0.6631 0.3184 0.3492 0.103 Uiso 1 1 calc R . .
H8B H 0.5249 0.3658 0.3845 0.103 Uiso 1 1 calc R . .
C9 C 0.5881(7) 0.0234(13) 0.4095(5) 0.078(2) Uani 1 1 d . . .
H9 H 0.5196 0.0108 0.4510 0.094 Uiso 1 1 calc R . .
C10 C 0.5419(5) -0.0952(13) 0.3087(4) 0.086(2) Uani 1 1 d . . .
H10A H 0.6123 -0.1726 0.2822 0.103 Uiso 1 1 calc R . .
H10B H 0.4663 -0.1954 0.3082 0.103 Uiso 1 1 calc R . .
C11 C 0.7135(10) -0.0507(16) 0.4597(6) 0.109(3) Uani 1 1 d . . .
C12 C 0.8329(7) -0.3482(16) 0.5408(6) 0.131(3) Uani 1 1 d . . .
H12A H 0.8154 -0.4668 0.5847 0.196 Uiso 1 1 calc R . .
H12B H 0.8879 -0.2327 0.5750 0.196 Uiso 1 1 calc R . .
H12C H 0.8769 -0.4131 0.4914 0.196 Uiso 1 1 calc R . .
C13 C 0.8822(6) 0.4539(12) 0.1642(5) 0.0668(18) Uani 1 1 d . . .
C14 C 0.9035(7) 0.5290(13) 0.2573(6) 0.089(2) Uani 1 1 d . . .
H14 H 0.8418 0.4993 0.2981 0.107 Uiso 1 1 calc R . .
C15 C 1.0196(8) 0.6515(15) 0.2914(6) 0.109(3) Uani 1 1 d . . .
H15 H 1.0328 0.7062 0.3542 0.130 Uiso 1 1 calc R . .
C16 C 1.1109(7) 0.6898(15) 0.2341(7) 0.105(3) Uani 1 1 d . . .
H16 H 1.1896 0.7616 0.2585 0.126 Uiso 1 1 calc R . .
C17 C 1.0887(8) 0.6246(16) 0.1418(7) 0.108(3) Uani 1 1 d . . .
H17 H 1.1493 0.6611 0.1009 0.129 Uiso 1 1 calc R . .
C18 C 0.9774(7) 0.5046(15) 0.1076(5) 0.092(2) Uani 1 1 d . . .
H18 H 0.9654 0.4554 0.0440 0.110 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
O1 C3 1.321(6) . ?
O1 C2 1.444(7) . ?
O2 C3 1.192(6) . ?
O3 C11 1.228(9) . ?
O4 C11 1.272(10) . ?
O4 C12 1.414(7) . ?
N1 C1 1.457(7) . ?
N1 C4 1.475(8) . ?
C1 C13 1.497(8) . ?
C1 C2 1.498(9) . ?
C3 C4 1.544(9) . ?
C4 C5 1.535(7) . ?
C4 C7 1.561(7) . ?
C5 C6 1.561(7) . ?
C6 C7 1.551(7) . ?
C7 C8 1.533(8) . ?
C7 C10 1.571(9) . ?
C8 C9 1.531(9) . ?
C9 C11 1.440(9) . ?
C9 C10 1.586(8) . ?
C13 C14 1.368(7) . ?
C13 C18 1.378(7) . ?
C14 C15 1.410(8) . ?
C15 C16 1.339(7) . ?
C16 C17 1.340(8) . ?
C17 C18 1.365(9) . ?

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
C3 O1 C2 119.2(5) . . ?
C11 O4 C12 119.5(7) . . ?
C1 N1 C4 117.9(5) . . ?
N1 C1 C13 111.2(5) . . ?
N1 C1 C2 106.5(5) . . ?
C13 C1 C2 109.0(5) . . ?
O1 C2 C1 109.9(5) . . ?
O2 C3 O1 121.6(7) . . ?
O2 C3 C4 122.0(6) . . ?
O1 C3 C4 116.0(5) . . ?
N1 C4 C5 113.9(6) . . ?
N1 C4 C3 113.6(5) . . ?
C5 C4 C3 113.5(5) . . ?
N1 C4 C7 117.1(5) . . ?
C5 C4 C7 87.5(4) . . ?
C3 C4 C7 108.5(6) . . ?
C4 C5 C6 91.8(5) . . ?
C7 C6 C5 86.9(4) . . ?
C8 C7 C6 118.5(6) . . ?
C8 C7 C4 121.3(5) . . ?
C6 C7 C4 91.2(4) . . ?
C8 C7 C10 87.9(4) . . ?
C6 C7 C10 117.5(5) . . ?
C4 C7 C10 123.5(6) . . ?
C9 C8 C7 93.1(5) . . ?
C11 C9 C8 119.6(6) . . ?
C11 C9 C10 115.9(6) . . ?
C8 C9 C10 87.4(5) . . ?
C7 C10 C9 89.6(5) . . ?
O3 C11 O4 119.4(9) . . ?
O3 C11 C9 124.9(9) . . ?
O4 C11 C9 114.8(8) . . ?
C14 C13 C18 117.1(6) . . ?
C14 C13 C1 123.7(6) . . ?
C18 C13 C1 119.2(7) . . ?
C13 C14 C15 119.7(7) . . ?
C16 C15 C14 120.7(8) . . ?
C15 C16 C17 120.0(8) . . ?
C16 C17 C18 120.1(8) . . ?
C17 C18 C13 122.2(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
C4 N1 C1 C13 -154.0(5) . . . . ?
C4 N1 C1 C2 -35.5(8) . . . . ?
C3 O1 C2 C1 -45.7(7) . . . . ?
N1 C1 C2 O1 64.9(7) . . . . ?
C13 C1 C2 O1 -175.1(5) . . . . ?
C2 O1 C3 O2 -177.9(6) . . . . ?
C2 O1 C3 C4 -5.2(8) . . . . ?
C1 N1 C4 C5 -143.6(5) . . . . ?
C1 N1 C4 C3 -11.4(8) . . . . ?
C1 N1 C4 C7 116.5(6) . . . . ?
O2 C3 C4 N1 -152.7(6) . . . . ?
O1 C3 C4 N1 34.6(8) . . . . ?
O2 C3 C4 C5 -20.3(9) . . . . ?
O1 C3 C4 C5 167.0(5) . . . . ?
O2 C3 C4 C7 75.2(8) . . . . ?
O1 C3 C4 C7 -97.5(6) . . . . ?
N1 C4 C5 C6 -130.9(6) . . . . ?
C3 C4 C5 C6 96.9(6) . . . . ?
C7 C4 C5 C6 -12.2(5) . . . . ?
C4 C5 C6 C7 12.3(5) . . . . ?
C5 C6 C7 C8 115.0(6) . . . . ?
C5 C6 C7 C4 -12.1(5) . . . . ?
C5 C6 C7 C10 -141.4(6) . . . . ?
N1 C4 C7 C8 3.2(9) . . . . ?
C5 C4 C7 C8 -112.5(6) . . . . ?
C3 C4 C7 C8 133.5(6) . . . . ?
N1 C4 C7 C6 128.0(6) . . . . ?
C5 C4 C7 C6 12.3(5) . . . . ?
C3 C4 C7 C6 -101.7(5) . . . . ?
N1 C4 C7 C10 -107.4(7) . . . . ?
C5 C4 C7 C10 136.9(6) . . . . ?
C3 C4 C7 C10 22.9(8) . . . . ?
C6 C7 C8 C9 109.3(6) . . . . ?
C4 C7 C8 C9 -139.7(6) . . . . ?
C10 C7 C8 C9 -11.0(5) . . . . ?
C7 C8 C9 C11 129.4(6) . . . . ?
C7 C8 C9 C10 10.9(5) . . . . ?
C8 C7 C10 C9 10.6(5) . . . . ?
C6 C7 C10 C9 -110.7(6) . . . . ?
C4 C7 C10 C9 137.5(6) . . . . ?
C11 C9 C10 C7 -132.5(6) . . . . ?
C8 C9 C10 C7 -10.7(5) . . . . ?
C12 O4 C11 O3 3.6(14) . . . . ?
C12 O4 C11 C9 173.2(6) . . . . ?
C8 C9 C11 O3 -8.7(13) . . . . ?
C10 C9 C11 O3 93.9(11) . . . . ?
C8 C9 C11 O4 -177.7(7) . . . . ?
C10 C9 C11 O4 -75.1(10) . . . . ?
N1 C1 C13 C14 35.1(9) . . . . ?
C2 C1 C13 C14 -82.0(8) . . . . ?
N1 C1 C13 C18 -146.0(6) . . . . ?
C2 C1 C13 C18 96.9(7) . . . . ?
C18 C13 C14 C15 -0.3(10) . . . . ?
C1 C13 C14 C15 178.6(7) . . . . ?
C13 C14 C15 C16 -1.8(12) . . . . ?
C14 C15 C16 C17 4.3(13) . . . . ?
C15 C16 C17 C18 -4.7(14) . . . . ?
C16 C17 C18 C13 2.6(13) . . . . ?
C14 C13 C18 C17 -0.1(11) . . . . ?
C1 C13 C18 C17 -179.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 962477'
