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# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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data_1d

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H28 Cl N3 O4'
_chemical_formula_sum            'C32 H28 Cl N3 O4'
_chemical_formula_weight         554.02

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.2361(14)
_cell_length_b                   10.7356(15)
_cell_length_c                   14.661(2)
_cell_angle_alpha                88.151(4)
_cell_angle_beta                 74.970(4)
_cell_angle_gamma                79.593(4)
_cell_volume                     1530.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6534
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.00

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.955
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5396
_reflns_number_gt                3632
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1002P)²+0.2726P] 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         5393
_refine_ls_number_parameters     363
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1780
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.171
_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
C1 C 1.2807(3) 0.6841(3) -0.1905(2) 0.0532(7) Uani 1 1 d U . .
C2 C 1.4059(3) 0.7225(3) -0.2258(2) 0.0651(7) Uani 1 1 d U . .
H2 H 1.4579 0.7029 -0.2874 0.078 Uiso 1 1 calc R . .
C3 C 1.4500(4) 0.7913(3) -0.1656(3) 0.0697(7) Uani 1 1 d U . .
H3 H 1.5338 0.8186 -0.1871 0.084 Uiso 1 1 calc R . .
C4 C 1.3721(3) 0.8215(3) -0.0724(2) 0.0651(7) Uani 1 1 d U . .
C5 C 1.3574(4) 0.9215(4) 0.0755(3) 0.0866(12) Uani 1 1 d . . .
H5A H 1.2680 0.9684 0.0759 0.130 Uiso 1 1 calc R . .
H5B H 1.4059 0.9727 0.1025 0.130 Uiso 1 1 calc R . .
H5C H 1.3477 0.8462 0.1119 0.130 Uiso 1 1 calc R . .
C6 C 1.2485(3) 0.7861(3) -0.0385(2) 0.0574(7) Uani 1 1 d U . .
H6 H 1.1963 0.8078 0.0227 0.069 Uiso 1 1 calc R . .
C7 C 1.2013(3) 0.7157(3) -0.0980(2) 0.0497(6) Uani 1 1 d U . .
C8 C 1.0809(3) 0.6612(3) -0.08320(19) 0.0494(6) Uani 1 1 d U . .
C9 C 1.0919(3) 0.5993(3) -0.1653(2) 0.0544(7) Uani 1 1 d U . .
H9 H 1.0280 0.5533 -0.1754 0.065 Uiso 1 1 calc R . .
C10 C 0.9692(3) 0.6656(3) 0.00662(19) 0.0488(6) Uani 1 1 d U . .
H10A H 1.0112 0.6462 0.0587 0.059 Uiso 1 1 calc R . .
H10B H 0.9165 0.6000 0.0035 0.059 Uiso 1 1 calc R . .
C11 C 0.8713(3) 0.7910(3) 0.02760(18) 0.0470(6) Uani 1 1 d U . .
H11A H 0.9211 0.8566 0.0362 0.056 Uiso 1 1 calc R . .
H11B H 0.8316 0.8139 -0.0253 0.056 Uiso 1 1 calc R . .
C12 C 0.6539(3) 0.7254(3) 0.11302(19) 0.0470(6) Uani 1 1 d U . .
H12 H 0.6294 0.7042 0.0595 0.056 Uiso 1 1 calc R . .
C13 C 0.5864(3) 0.7042(3) 0.20456(18) 0.0428(5) Uani 1 1 d U . .
C14 C 0.4660(3) 0.6451(3) 0.23319(19) 0.0453(6) Uani 1 1 d U . .
C15 C 0.3170(3) 0.5358(4) 0.1803(2) 0.0679(10) Uani 1 1 d U . .
H15A H 0.2311 0.5947 0.2021 0.081 Uiso 1 1 calc R . .
H15B H 0.3257 0.4744 0.2293 0.081 Uiso 1 1 calc R . .
C16 C 0.3194(4) 0.4706(4) 0.0914(3) 0.0746(10) Uani 1 1 d U . .
H16A H 0.3041 0.5327 0.0448 0.112 Uiso 1 1 calc R . .
H16B H 0.2484 0.4202 0.1039 0.112 Uiso 1 1 calc R . .
H16C H 0.4072 0.4171 0.0682 0.112 Uiso 1 1 calc R . .
C17 C 0.5871(3) 0.6385(3) 0.42236(17) 0.0406(6) Uani 1 1 d U . .
C18 C 0.6180(3) 0.7592(2) 0.36988(17) 0.0383(5) Uani 1 1 d U . .
H18 H 0.6937 0.7847 0.3898 0.046 Uiso 1 1 calc R . .
C19 C 0.4898(3) 0.8531(2) 0.41247(18) 0.0413(5) Uani 1 1 d U . .
C20 C 0.4474(3) 0.9754(3) 0.38874(19) 0.0470(6) Uani 1 1 d U . .
H20 H 0.5012 1.0146 0.3391 0.056 Uiso 1 1 calc R . .
C21 C 0.3211(3) 1.0388(3) 0.4415(2) 0.0543(7) Uani 1 1 d U . .
C22 C 0.2414(3) 0.9822(3) 0.5161(2) 0.0587(7) Uani 1 1 d U . .
H22 H 0.1577 1.0274 0.5505 0.070 Uiso 1 1 calc R . .
C23 C 0.2850(3) 0.8589(3) 0.5402(2) 0.0561(7) Uani 1 1 d U . .
H23 H 0.2324 0.8202 0.5907 0.067 Uiso 1 1 calc R . .
C24 C 0.4084(3) 0.7958(3) 0.48698(18) 0.0450(6) Uani 1 1 d U . .
C25 C 0.6596(3) 0.7497(2) 0.26349(17) 0.0379(5) Uani 1 1 d U . .
C26 C 0.7680(3) 0.7952(2) 0.20604(17) 0.0377(5) Uani 1 1 d U . .
C27 C 0.8732(3) 0.8557(3) 0.22942(18) 0.0415(5) Uani 1 1 d U . .
C28 C 0.9693(3) 0.7881(3) 0.2730(2) 0.0516(6) Uani 1 1 d U . .
H28 H 0.9679 0.7031 0.2865 0.062 Uiso 1 1 calc R . .
C29 C 1.0668(3) 0.8458(3) 0.2965(2) 0.0603(7) Uani 1 1 d U . .
H29 H 1.1298 0.7999 0.3262 0.072 Uiso 1 1 calc R . .
C30 C 1.0702(3) 0.9718(3) 0.2758(2) 0.0621(7) Uani 1 1 d U . .
H30 H 1.1360 1.0105 0.2913 0.075 Uiso 1 1 calc R . .
C31 C 0.9773(3) 1.0400(3) 0.2326(2) 0.0597(7) Uani 1 1 d U . .
H31 H 0.9800 1.1248 0.2187 0.072 Uiso 1 1 calc R . .
C32 C 0.8796(3) 0.9826(3) 0.2099(2) 0.0506(6) Uani 1 1 d U . .
H32 H 0.8166 1.0296 0.1807 0.061 Uiso 1 1 calc R . .
Cl1 Cl 0.26206(10) 1.19403(8) 0.41323(7) 0.0807(3) Uani 1 1 d . . .
N1 N 1.2096(3) 0.6144(2) -0.23031(17) 0.0599(7) Uani 1 1 d . . .
H1 H 1.2352 0.5849 -0.2873 0.072 Uiso 1 1 calc R . .
N2 N 0.7616(2) 0.7818(2) 0.11320(14) 0.0422(6) Uani 1 1 d . . .
N3 N 0.4725(2) 0.6705(2) 0.49371(15) 0.0471(6) Uani 1 1 d . . .
H3A H 0.4427 0.6200 0.5378 0.056 Uiso 1 1 calc R . .
O1 O 1.4335(3) 0.8869(3) -0.0208(2) 0.0947(9) Uani 1 1 d . . .
O2 O 0.4021(2) 0.6336(2) 0.31393(14) 0.0682(7) Uani 1 1 d . . .
O3 O 0.4319(2) 0.6032(2) 0.15918(14) 0.0620(6) Uani 1 1 d . . .
O4 O 0.6555(2) 0.53075(18) 0.40560(12) 0.0504(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.370(4) . ?
C1 C2 1.383(4) . ?
C1 C7 1.405(4) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.352(4) . ?
C4 O1 1.379(4) . ?
C5 O1 1.447(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.399(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.422(4) . ?
C8 C9 1.362(4) . ?
C8 C10 1.499(4) . ?
C9 N1 1.361(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.513(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.465(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.351(4) . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C13 C25 1.429(4) . ?
C13 C14 1.447(4) . ?
C14 O2 1.209(3) . ?
C14 O3 1.337(3) . ?
C15 O3 1.451(4) . ?
C15 C16 1.492(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O4 1.235(3) . ?
C17 N3 1.353(3) . ?
C17 C18 1.526(4) . ?
C18 C19 1.505(4) . ?
C18 C25 1.508(3) . ?
C18 H18 0.9800 . ?
C19 C20 1.370(4) . ?
C19 C24 1.391(4) . ?
C20 C21 1.389(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(4) . ?
C21 Cl1 1.743(3) . ?
C22 C23 1.384(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(4) . ?
C23 H23 0.9300 . ?
C24 N3 1.398(4) . ?
C25 C26 1.365(3) . ?
C26 N2 1.393(3) . ?
C26 C27 1.468(4) . ?
C27 C32 1.392(4) . ?
C27 C28 1.394(4) . ?
C28 C29 1.383(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.382(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.368(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.379(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
N1 H1 0.8600 . ?
N3 H3A 0.8600 . ?

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
N1 C1 C2 131.6(3) . . ?
N1 C1 C7 106.9(3) . . ?
C2 C1 C7 121.4(3) . . ?
C3 C2 C1 116.9(3) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.0 . . ?
C6 C4 O1 124.5(3) . . ?
C6 C4 C3 121.2(3) . . ?
O1 C4 C3 114.4(3) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 118.2(3) . . ?
C4 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C6 C7 C1 120.4(3) . . ?
C6 C7 C8 132.0(3) . . ?
C1 C7 C8 107.6(3) . . ?
C9 C8 C7 106.0(2) . . ?
C9 C8 C10 127.4(3) . . ?
C7 C8 C10 126.5(3) . . ?
N1 C9 C8 110.3(3) . . ?
N1 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C8 C10 C11 114.8(2) . . ?
C8 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C8 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
N2 C11 C10 110.0(2) . . ?
N2 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N2 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N2 C12 C13 109.1(2) . . ?
N2 C12 H12 125.4 . . ?
C13 C12 H12 125.4 . . ?
C12 C13 C25 106.5(2) . . ?
C12 C13 C14 125.5(3) . . ?
C25 C13 C14 127.9(2) . . ?
O2 C14 O3 122.8(3) . . ?
O2 C14 C13 125.2(3) . . ?
O3 C14 C13 112.0(2) . . ?
O3 C15 C16 107.3(3) . . ?
O3 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O3 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 N3 125.3(2) . . ?
O4 C17 C18 126.9(2) . . ?
N3 C17 C18 107.8(2) . . ?
C19 C18 C25 115.8(2) . . ?
C19 C18 C17 102.0(2) . . ?
C25 C18 C17 116.3(2) . . ?
C19 C18 H18 107.4 . . ?
C25 C18 H18 107.4 . . ?
C17 C18 H18 107.4 . . ?
C20 C19 C24 120.6(2) . . ?
C20 C19 C18 130.9(2) . . ?
C24 C19 C18 108.5(2) . . ?
C19 C20 C21 117.5(3) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
C22 C21 C20 121.8(3) . . ?
C22 C21 Cl1 119.1(2) . . ?
C20 C21 Cl1 119.2(2) . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 117.6(3) . . ?
C24 C23 H23 121.2 . . ?
C22 C23 H23 121.2 . . ?
C23 C24 C19 121.9(3) . . ?
C23 C24 N3 129.0(3) . . ?
C19 C24 N3 109.0(2) . . ?
C26 C25 C13 107.7(2) . . ?
C26 C25 C18 125.3(2) . . ?
C13 C25 C18 126.7(2) . . ?
C25 C26 N2 107.6(2) . . ?
C25 C26 C27 130.4(2) . . ?
N2 C26 C27 121.9(2) . . ?
C32 C27 C28 117.6(3) . . ?
C32 C27 C26 121.4(3) . . ?
C28 C27 C26 121.0(2) . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C28 119.8(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 119.7(3) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C27 121.5(3) . . ?
C31 C32 H32 119.2 . . ?
C27 C32 H32 119.2 . . ?
C9 N1 C1 109.0(2) . . ?
C9 N1 H1 125.5 . . ?
C1 N1 H1 125.5 . . ?
C12 N2 C26 109.1(2) . . ?
C12 N2 C11 122.2(2) . . ?
C26 N2 C11 126.6(2) . . ?
C17 N3 C24 111.7(2) . . ?
C17 N3 H3A 124.1 . . ?
C24 N3 H3A 124.1 . . ?
C4 O1 C5 116.8(3) . . ?
C14 O3 C15 116.5(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.86 2.11 2.929(3) 160.1 2_765
N3 H3A O4 0.86 2.09 2.894(3) 154.5 2_666

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.056


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.500 193 46 ' '
_platon_squeeze_details          
; 
;
_database_code_depnum_ccdc_archive 'CCDC 1013721'
#######################################################################
#
#                 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_1i

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H26 Cl N3 O5'
_chemical_formula_sum            'C32 H26 Cl N3 O5'
_chemical_formula_weight         568.01

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.634(2)
_cell_length_b                   19.608(5)
_cell_length_c                   15.793(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.544(7)
_cell_angle_gamma                90.00
_cell_volume                     2874.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7141
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      22.15

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.961
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50091
_diffrn_reflns_av_R_equivalents  0.1138
_diffrn_reflns_av_sigmaI/netI    0.0966
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.58
_reflns_number_total             6665
_reflns_number_gt                2818
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0770P)²+0.3569P] 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         6621
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1896
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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
C1 C 0.3461(3) 0.64829(15) 0.43425(17) 0.0743(8) Uani 1 1 d . . .
C2 C 0.2563(4) 0.62593(18) 0.3545(2) 0.1082(12) Uani 1 1 d . . .
H2 H 0.2321 0.5801 0.3446 0.130 Uiso 1 1 calc R . .
C3 C 0.2055(4) 0.6742(2) 0.2915(2) 0.1141(13) Uani 1 1 d . . .
H3 H 0.1445 0.6606 0.2379 0.137 Uiso 1 1 calc R . .
C4 C 0.2416(3) 0.74311(18) 0.30441(19) 0.0917(10) Uani 1 1 d . . .
C5 C 0.2289(5) 0.8510(2) 0.2359(3) 0.1474(17) Uani 1 1 d . . .
H5A H 0.1940 0.8761 0.2783 0.221 Uiso 1 1 calc R . .
H5B H 0.1925 0.8713 0.1789 0.221 Uiso 1 1 calc R . .
H5C H 0.3323 0.8521 0.2522 0.221 Uiso 1 1 calc R . .
C6 C 0.3284(3) 0.76542(15) 0.38248(17) 0.0772(8) Uani 1 1 d . . .
H6 H 0.3520 0.8113 0.3914 0.093 Uiso 1 1 calc R . .
C7 C 0.3813(3) 0.71723(14) 0.44911(17) 0.0659(7) Uani 1 1 d . . .
C8 C 0.6646(3) 0.76166(14) 0.66132(18) 0.0842(9) Uani 1 1 d . A .
H8A H 0.7465 0.7565 0.6372 0.101 Uiso 1 1 calc R . .
H8B H 0.6869 0.7978 0.7048 0.101 Uiso 1 1 calc R . .
C9 C 0.5369(3) 0.78174(14) 0.58997(18) 0.0890(10) Uani 1 1 d . . .
H9A H 0.5650 0.8156 0.5529 0.107 Uiso 1 1 calc R . .
H9B H 0.4656 0.8022 0.6153 0.107 Uiso 1 1 calc R . .
C10 C 0.4724(3) 0.72211(13) 0.53563(16) 0.0648(7) Uani 1 1 d . . .
C11 C 0.4885(3) 0.65746(13) 0.56998(16) 0.0638(7) Uani 1 1 d . . .
C12 C 0.5705(3) 0.64340(12) 0.65881(16) 0.0578(7) Uani 1 1 d . A .
C13 C 0.5896(3) 0.58906(11) 0.71648(16) 0.0552(6) Uani 1 1 d . . .
C14 C 0.5212(3) 0.52306(13) 0.6948(2) 0.0662(7) Uani 1 1 d . . .
C15 C 0.4681(4) 0.41849(15) 0.7524(2) 0.1112(12) Uani 1 1 d . . .
H15A H 0.3694 0.4227 0.7189 0.167 Uiso 1 1 calc R . .
H15B H 0.4721 0.3985 0.8085 0.167 Uiso 1 1 calc R . .
H15C H 0.5189 0.3900 0.7213 0.167 Uiso 1 1 calc R . .
C16 C 0.6141(3) 0.54835(13) 0.92848(16) 0.0626(7) Uani 1 1 d . . .
C17 C 0.7271(3) 0.57491(11) 0.88533(16) 0.0577(7) Uani 1 1 d . . .
H17 H 0.7846 0.6078 0.9270 0.069 Uiso 1 1 calc R . .
C18 C 0.8230(3) 0.51355(12) 0.88948(16) 0.0583(7) Uani 1 1 d . . .
C19 C 0.9405(3) 0.50275(14) 0.85865(18) 0.0719(8) Uani 1 1 d . . .
H19 H 0.9722 0.5361 0.8264 0.086 Uiso 1 1 calc R . .
C20 C 1.0118(3) 0.44075(18) 0.8766(2) 0.0820(9) Uani 1 1 d . . .
C21 C 0.9667(4) 0.39087(16) 0.9232(2) 0.0833(9) Uani 1 1 d . . .
H21 H 1.0164 0.3497 0.9338 0.100 Uiso 1 1 calc R . .
C22 C 0.8481(3) 0.40090(14) 0.95469(18) 0.0744(8) Uani 1 1 d . . .
H22 H 0.8163 0.3671 0.9864 0.089 Uiso 1 1 calc R . .
C23 C 0.7780(3) 0.46284(13) 0.93758(16) 0.0613(7) Uani 1 1 d . . .
C24 C 0.6762(2) 0.61264(12) 0.80022(15) 0.0527(6) Uani 1 1 d . . .
C25 C 0.7078(2) 0.67951(13) 0.79063(15) 0.0550(6) Uani 1 1 d . A .
C26 C 0.7803(3) 0.73128(12) 0.85576(16) 0.0538(6) Uani 1 1 d . . .
C27 C 0.6994(10) 0.7831(6) 0.8791(7) 0.065(2) Uani 0.69(3) 1 d P A 1
H27A H 0.6005 0.7835 0.8536 0.077 Uiso 0.69(3) 1 calc PR A 1
C28 C 0.7592(12) 0.8351(6) 0.9395(7) 0.070(2) Uani 0.69(3) 1 d P A 1
H28A H 0.7022 0.8689 0.9543 0.084 Uiso 0.69(3) 1 calc PR A 1
C27' C 0.707(2) 0.7574(15) 0.9072(19) 0.069(5) Uani 0.31(3) 1 d P A 2
H27B H 0.6155 0.7410 0.9056 0.083 Uiso 0.31(3) 1 calc PR A 2
C28' C 0.766(3) 0.8076(15) 0.961(2) 0.077(6) Uani 0.31(3) 1 d P A 2
H28B H 0.7081 0.8273 0.9936 0.093 Uiso 0.31(3) 1 calc PR A 2
C29 C 0.9034(3) 0.83350(15) 0.97505(19) 0.0721(8) Uani 1 1 d . . .
C30 C 0.8885(5) 0.9319(2) 1.0615(3) 0.170(2) Uani 1 1 d . . .
H30A H 0.8286 0.9556 1.0118 0.255 Uiso 1 1 calc R A .
H30B H 0.9505 0.9640 1.0996 0.255 Uiso 1 1 calc R . .
H30C H 0.8290 0.9094 1.0929 0.255 Uiso 1 1 calc R . .
C31 C 0.9889(13) 0.7837(6) 0.9563(12) 0.087(3) Uani 0.71(3) 1 d P A 1
H31A H 1.0874 0.7828 0.9831 0.105 Uiso 0.71(3) 1 calc PR A 1
C32 C 0.9235(14) 0.7344(5) 0.8953(9) 0.075(3) Uani 0.71(3) 1 d P A 1
H32A H 0.9821 0.7013 0.8807 0.090 Uiso 0.71(3) 1 calc PR A 1
C31' C 0.977(3) 0.802(3) 0.919(3) 0.103(10) Uani 0.29(3) 1 d P A 2
H31B H 1.0672 0.8188 0.9202 0.124 Uiso 0.29(3) 1 calc PR A 2
C32' C 0.928(4) 0.748(2) 0.864(3) 0.112(12) Uani 0.29(3) 1 d P A 2
H32B H 0.9854 0.7246 0.8342 0.135 Uiso 0.29(3) 1 calc PR A 2
Cl1 Cl 1.16111(10) 0.42656(5) 0.83765(8) 0.1358(5) Uani 1 1 d . . .
N1 N 0.4136(3) 0.61226(11) 0.50854(14) 0.0789(7) Uani 1 1 d . . .
H1 H 0.4095 0.5688 0.5152 0.095 Uiso 1 1 calc R . .
N2 N 0.6430(2) 0.69814(10) 0.70425(13) 0.0603(6) Uani 1 1 d . . .
N3 N 0.6558(2) 0.48520(10) 0.96118(13) 0.0691(6) Uani 1 1 d . . .
H3A H 0.6124 0.4619 0.9925 0.083 Uiso 1 1 calc R . .
O1 O 0.1825(3) 0.78418(15) 0.23354(15) 0.1252(9) Uani 1 1 d . . .
O2 O 0.4580(3) 0.50288(9) 0.62217(14) 0.1028(8) Uani 1 1 d . . .
O3 O 0.5337(2) 0.48465(9) 0.76515(12) 0.0793(6) Uani 1 1 d . . .
O4 O 0.5077(2) 0.57906(9) 0.93645(12) 0.0749(5) Uani 1 1 d . . .
O5 O 0.9735(2) 0.88268(12) 1.03203(15) 0.1085(7) Uani 1 1 d . A .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.375(3) . ?
C1 C2 1.394(4) . ?
C1 C7 1.398(4) . ?
C2 C3 1.366(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.363(4) . ?
C4 O1 1.373(4) . ?
C5 O1 1.382(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.404(4) . ?
C6 H6 0.9300 . ?
C7 C10 1.415(3) . ?
C8 N2 1.459(3) . ?
C8 C9 1.481(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.485(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.371(3) . ?
C11 N1 1.368(3) . ?
C11 C12 1.440(3) . ?
C12 N2 1.373(3) . ?
C12 C13 1.382(3) . ?
C13 C24 1.438(3) . ?
C13 C14 1.451(3) . ?
C14 O2 1.212(3) . ?
C14 O3 1.321(3) . ?
C15 O3 1.433(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O4 1.224(3) . ?
C16 N3 1.360(3) . ?
C16 C17 1.523(4) . ?
C17 C24 1.497(3) . ?
C17 C18 1.507(3) . ?
C17 H17 0.9800 . ?
C18 C19 1.364(4) . ?
C18 C23 1.389(3) . ?
C19 C20 1.387(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(4) . ?
C20 Cl1 1.732(3) . ?
C21 C22 1.377(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9300 . ?
C23 N3 1.397(3) . ?
C24 C25 1.364(3) . ?
C25 N2 1.389(3) . ?
C25 C26 1.480(3) . ?
C26 C27' 1.32(2) . ?
C26 C32 1.354(13) . ?
C26 C27 1.390(10) . ?
C26 C32' 1.43(3) . ?
C27 C28 1.409(15) . ?
C27 H27A 0.9300 . ?
C28 C29 1.351(11) . ?
C28 H28A 0.9300 . ?
C27' C28' 1.33(3) . ?
C27' H27B 0.9300 . ?
C28' C29 1.38(2) . ?
C28' H28B 0.9300 . ?
C29 C31 1.360(13) . ?
C29 O5 1.368(3) . ?
C29 C31' 1.42(3) . ?
C30 O5 1.422(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.390(19) . ?
C31 H31A 0.9300 . ?
C32 H32A 0.9300 . ?
C31' C32' 1.37(5) . ?
C31' H31B 0.9300 . ?
C32' H32B 0.9300 . ?
N1 H1 0.8600 . ?
N3 H3A 0.8600 . ?

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
N1 C1 C2 130.3(3) . . ?
N1 C1 C7 108.4(2) . . ?
C2 C1 C7 121.3(3) . . ?
C3 C2 C1 117.1(3) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 122.5(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C6 C4 O1 124.7(3) . . ?
C6 C4 C3 120.8(3) . . ?
O1 C4 C3 114.6(3) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 118.2(3) . . ?
C4 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C1 C7 C6 120.1(2) . . ?
C1 C7 C10 106.7(2) . . ?
C6 C7 C10 133.2(2) . . ?
N2 C8 C9 112.8(2) . . ?
N2 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 111.3(2) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C7 107.1(2) . . ?
C11 C10 C9 120.9(2) . . ?
C7 C10 C9 131.8(2) . . ?
N1 C11 C10 109.6(2) . . ?
N1 C11 C12 127.9(2) . . ?
C10 C11 C12 122.5(2) . . ?
N2 C12 C13 107.4(2) . . ?
N2 C12 C11 115.4(2) . . ?
C13 C12 C11 137.0(2) . . ?
C12 C13 C24 107.5(2) . . ?
C12 C13 C14 124.1(2) . . ?
C24 C13 C14 128.2(2) . . ?
O2 C14 O3 121.3(2) . . ?
O2 C14 C13 126.6(3) . . ?
O3 C14 C13 112.1(2) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 N3 125.4(2) . . ?
O4 C16 C17 126.6(2) . . ?
N3 C16 C17 107.9(2) . . ?
C24 C17 C18 118.9(2) . . ?
C24 C17 C16 118.0(2) . . ?
C18 C17 C16 102.2(2) . . ?
C24 C17 H17 105.5 . . ?
C18 C17 H17 105.5 . . ?
C16 C17 H17 105.5 . . ?
C19 C18 C23 119.7(2) . . ?
C19 C18 C17 131.8(2) . . ?
C23 C18 C17 108.5(2) . . ?
C18 C19 C20 118.4(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C21 C20 C19 121.8(3) . . ?
C21 C20 Cl1 119.5(3) . . ?
C19 C20 Cl1 118.8(3) . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 117.7(3) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 H22 121.2 . . ?
C22 C23 C18 121.9(3) . . ?
C22 C23 N3 128.8(3) . . ?
C18 C23 N3 109.3(2) . . ?
C25 C24 C13 107.4(2) . . ?
C25 C24 C17 123.1(2) . . ?
C13 C24 C17 129.5(2) . . ?
C24 C25 N2 107.9(2) . . ?
C24 C25 C26 131.3(2) . . ?
N2 C25 C26 120.4(2) . . ?
C27' C26 C32 110.3(12) . . ?
C27' C26 C27 28.2(11) . . ?
C32 C26 C27 114.7(6) . . ?
C27' C26 C32' 123.0(16) . . ?
C32 C26 C32' 23.7(19) . . ?
C27 C26 C32' 115.2(15) . . ?
C27' C26 C25 117.6(9) . . ?
C32 C26 C25 125.8(5) . . ?
C27 C26 C25 119.5(4) . . ?
C32' C26 C25 119.3(13) . . ?
C26 C27 C28 123.5(8) . . ?
C26 C27 H27A 118.3 . . ?
C28 C27 H27A 118.3 . . ?
C29 C28 C27 116.9(8) . . ?
C29 C28 H28A 121.5 . . ?
C27 C28 H28A 121.5 . . ?
C26 C27' C28' 118.6(17) . . ?
C26 C27' H27B 120.7 . . ?
C28' C27' H27B 120.7 . . ?
C27' C28' C29 126.8(18) . . ?
C27' C28' H28B 116.6 . . ?
C29 C28' H28B 116.6 . . ?
C28 C29 C31 122.8(7) . . ?
C28 C29 O5 121.9(5) . . ?
C31 C29 O5 115.3(6) . . ?
C28 C29 C28' 26.8(11) . . ?
C31 C29 C28' 108.3(12) . . ?
O5 C29 C28' 130.2(10) . . ?
C28 C29 C31' 112.4(14) . . ?
C31 C29 C31' 27.6(17) . . ?
O5 C29 C31' 118.7(13) . . ?
C28' C29 C31' 111.0(16) . . ?
O5 C30 H30A 109.5 . . ?
O5 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O5 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 C32 117.4(10) . . ?
C29 C31 H31A 121.3 . . ?
C32 C31 H31A 121.3 . . ?
C26 C32 C31 124.6(9) . . ?
C26 C32 H32A 117.7 . . ?
C31 C32 H32A 117.7 . . ?
C32' C31' C29 127(2) . . ?
C32' C31' H31B 116.7 . . ?
C29 C31' H31B 116.7 . . ?
C31' C32' C26 113(2) . . ?
C31' C32' H32B 123.5 . . ?
C26 C32' H32B 123.5 . . ?
C11 N1 C1 108.1(2) . . ?
C11 N1 H1 125.9 . . ?
C1 N1 H1 125.9 . . ?
C12 N2 C25 109.86(19) . . ?
C12 N2 C8 122.7(2) . . ?
C25 N2 C8 126.7(2) . . ?
C16 N3 C23 111.6(2) . . ?
C16 N3 H3A 124.2 . . ?
C23 N3 H3A 124.2 . . ?
C4 O1 C5 118.3(3) . . ?
C14 O3 C15 117.4(2) . . ?
C29 O5 C30 117.9(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O4 0.86 1.98 2.837(3) 171.0 3_667
N1 H1 O2 0.86 2.08 2.755(3) 135.1 .

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 1013722'
#######################################################################
#
#                 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_B1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 F N3 O5'
_chemical_formula_sum            'C26 H26 F N3 O5'
_chemical_formula_weight         479.50

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.4883(8)
_cell_length_b                   14.9998(15)
_cell_length_c                   15.5192(16)
_cell_angle_alpha                61.259(3)
_cell_angle_beta                 89.624(3)
_cell_angle_gamma                87.591(3)
_cell_volume                     1526.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.41

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.043
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.979
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23248
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         27.55
_reflns_number_total             7059
_reflns_number_gt                4503
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1227P)²+0.0399P] 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         6992
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.2200
_refine_ls_wR_factor_gt          0.2039
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
C1 C 0.1703(3) 0.44810(17) 0.37559(14) 0.0534(5) Uani 1 1 d . . .
C2 C 0.1222(3) 0.4292(2) 0.29914(17) 0.0726(7) Uani 1 1 d . . .
H2 H 0.0725 0.4802 0.2404 0.087 Uiso 1 1 calc R . .
C3 C 0.1520(5) 0.3320(3) 0.3149(2) 0.0911(9) Uani 1 1 d . . .
H3 H 0.1218 0.3167 0.2656 0.109 Uiso 1 1 calc R . .
C4 C 0.2253(5) 0.2559(2) 0.4017(3) 0.1002(10) Uani 1 1 d . . .
H4 H 0.2435 0.1906 0.4097 0.120 Uiso 1 1 calc R . .
C5 C 0.2723(4) 0.2750(2) 0.47704(18) 0.0743(7) Uani 1 1 d . . .
H5 H 0.3229 0.2231 0.5351 0.089 Uiso 1 1 calc R . .
C6 C 0.2435(3) 0.37176(16) 0.46533(14) 0.0521(5) Uani 1 1 d . . .
C7 C 0.2699(2) 0.41817(15) 0.52667(14) 0.0492(5) Uani 1 1 d . . .
C8 C 0.2152(3) 0.51722(16) 0.47168(14) 0.0559(5) Uani 1 1 d . . .
H8 H 0.2176 0.5656 0.4928 0.067 Uiso 1 1 calc R . .
C9 C 0.3326(3) 0.36444(16) 0.63080(14) 0.0562(5) Uani 1 1 d . . .
H9A H 0.4500 0.3328 0.6344 0.067 Uiso 1 1 calc R . .
H9B H 0.2520 0.3107 0.6688 0.067 Uiso 1 1 calc R . .
C10 C 0.3435(3) 0.43299(15) 0.67656(13) 0.0522(5) Uani 1 1 d . . .
H10A H 0.4408 0.4783 0.6471 0.063 Uiso 1 1 calc R . .
H10B H 0.2335 0.4746 0.6619 0.063 Uiso 1 1 calc R . .
C11 C 0.5284(2) 0.36431(14) 0.82522(14) 0.0460(4) Uani 1 1 d . . .
H11 H 0.6233 0.3927 0.7832 0.055 Uiso 1 1 calc R . .
C12 C 0.5708(2) 0.31387(13) 0.92425(13) 0.0412(4) Uani 1 1 d . . .
C13 C 0.4287(2) 0.27428(14) 0.99329(14) 0.0438(4) Uani 1 1 d . . .
C14 C 0.3466(4) 0.1923(2) 1.16019(18) 0.0820(8) Uani 1 1 d . . .
H14A H 0.2468 0.2405 1.1423 0.123 Uiso 1 1 calc R . .
H14B H 0.3934 0.1781 1.2232 0.123 Uiso 1 1 calc R . .
H14C H 0.3083 0.1305 1.1635 0.123 Uiso 1 1 calc R . .
C15 C 0.7648(2) 0.30587(14) 0.95553(13) 0.0443(4) Uani 1 1 d . . .
H15 H 0.8204 0.3621 0.8995 0.053 Uiso 1 1 calc R . .
C16 C 0.7939(3) 0.32678(15) 1.04025(16) 0.0538(5) Uani 1 1 d . . .
C17 C 0.7353(6) 0.4467(2) 1.0984(3) 0.1106(13) Uani 1 1 d . . .
H17A H 0.8547 0.4273 1.1270 0.133 Uiso 1 1 calc R . .
H17B H 0.7207 0.5203 1.0679 0.133 Uiso 1 1 calc R . .
C18 C 0.6063(9) 0.4018(4) 1.1757(4) 0.1570(19) Uani 1 1 d . . .
H18A H 0.4877 0.4197 1.1478 0.236 Uiso 1 1 calc R . .
H18B H 0.6206 0.4268 1.2217 0.236 Uiso 1 1 calc R . .
H18C H 0.6248 0.3291 1.2090 0.236 Uiso 1 1 calc R . .
C19 C 0.9062(2) 0.21739(16) 0.86875(14) 0.0523(5) Uani 1 1 d . . .
C20 C 0.8708(2) 0.21049(14) 0.96877(13) 0.0437(4) Uani 1 1 d . . .
H20 H 0.9864 0.2077 0.9994 0.052 Uiso 1 1 calc R . .
C21 C 0.7917(2) 0.10731(14) 1.02481(14) 0.0447(4) Uani 1 1 d . . .
C22 C 0.7364(3) 0.05333(15) 1.12026(15) 0.0544(5) Uani 1 1 d . . .
H22 H 0.7369 0.0809 1.1627 0.065 Uiso 1 1 calc R . .
C23 C 0.6799(3) -0.04357(17) 1.15042(18) 0.0654(6) Uani 1 1 d . . .
C24 C 0.6774(3) -0.08793(17) 1.0922(2) 0.0683(6) Uani 1 1 d . . .
H24 H 0.6384 -0.1537 1.1167 0.082 Uiso 1 1 calc R . .
C25 C 0.7330(3) -0.03452(17) 0.99661(19) 0.0636(6) Uani 1 1 d . . .
H25 H 0.7323 -0.0631 0.9551 0.076 Uiso 1 1 calc R . .
C26 C 0.7901(2) 0.06290(15) 0.96401(15) 0.0497(5) Uani 1 1 d . . .
F1 F 0.6244(3) -0.09793(11) 1.24523(12) 0.1026(6) Uani 1 1 d . . .
N1 N 0.1562(2) 0.53648(14) 0.38095(12) 0.0581(5) Uani 1 1 d . . .
H1 H 0.1167 0.5946 0.3349 0.070 Uiso 1 1 calc R . .
N2 N 0.3715(2) 0.37740(13) 0.78262(11) 0.0530(4) Uani 1 1 d . . .
H2A H 0.2807 0.3518 0.8192 0.064 Uiso 1 1 calc R . .
N3 N 0.8560(2) 0.13063(14) 0.87213(13) 0.0569(5) Uani 1 1 d . . .
H3A H 0.8637 0.1184 0.8235 0.068 Uiso 1 1 calc R . .
O1 O 0.27152(18) 0.27647(12) 0.97143(10) 0.0605(4) Uani 1 1 d . . .
O2 O 0.48282(18) 0.23386(11) 1.08806(9) 0.0562(4) Uani 1 1 d . . .
O3 O 0.8818(2) 0.27308(12) 1.11349(11) 0.0654(4) Uani 1 1 d . . .
O4 O 0.7176(3) 0.41554(12) 1.02245(13) 0.0800(5) Uani 1 1 d . . .
O5 O 0.9684(2) 0.29017(12) 0.79783(10) 0.0676(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.367(3) . ?
C1 C2 1.399(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.365(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(3) . ?
C7 C8 1.356(3) . ?
C7 C9 1.486(3) . ?
C8 N1 1.367(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.509(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.455(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.312(2) . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.435(3) . ?
C12 C15 1.516(2) . ?
C13 O1 1.222(2) . ?
C13 O2 1.351(2) . ?
C14 O2 1.431(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.510(3) . ?
C15 C20 1.531(3) . ?
C15 H15 0.9800 . ?
C16 O3 1.208(2) . ?
C16 O4 1.327(3) . ?
C17 C18 1.445(7) . ?
C17 O4 1.471(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O5 1.225(2) . ?
C19 N3 1.346(3) . ?
C19 C20 1.527(3) . ?
C20 C21 1.509(3) . ?
C20 H20 0.9800 . ?
C21 C22 1.374(3) . ?
C21 C26 1.393(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.355(4) . ?
C23 F1 1.367(3) . ?
C24 C25 1.377(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9300 . ?
C26 N3 1.396(3) . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?

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
N1 C1 C2 129.8(2) . . ?
N1 C1 C6 107.67(17) . . ?
C2 C1 C6 122.6(2) . . ?
C3 C2 C1 116.7(2) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 122.0(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 118.30(19) . . ?
C5 C6 C7 134.75(19) . . ?
C1 C6 C7 106.95(18) . . ?
C8 C7 C6 105.78(18) . . ?
C8 C7 C9 128.28(19) . . ?
C6 C7 C9 125.81(18) . . ?
C7 C8 N1 110.9(2) . . ?
C7 C8 H8 124.5 . . ?
N1 C8 H8 124.5 . . ?
C7 C9 C10 113.69(17) . . ?
C7 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C7 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
N2 C10 C9 113.20(17) . . ?
N2 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 128.45(18) . . ?
N2 C11 H11 115.8 . . ?
C12 C11 H11 115.8 . . ?
C11 C12 C13 118.57(16) . . ?
C11 C12 C15 118.60(16) . . ?
C13 C12 C15 122.80(15) . . ?
O1 C13 O2 121.20(17) . . ?
O1 C13 C12 124.99(17) . . ?
O2 C13 C12 113.81(15) . . ?
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 . . ?
C16 C15 C12 114.40(16) . . ?
C16 C15 C20 112.22(15) . . ?
C12 C15 C20 115.31(14) . . ?
C16 C15 H15 104.5 . . ?
C12 C15 H15 104.5 . . ?
C20 C15 H15 104.5 . . ?
O3 C16 O4 123.20(19) . . ?
O3 C16 C15 125.37(19) . . ?
O4 C16 C15 111.35(17) . . ?
C18 C17 O4 113.0(3) . . ?
C18 C17 H17A 109.0 . . ?
O4 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
O4 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 N3 126.3(2) . . ?
O5 C19 C20 125.4(2) . . ?
N3 C19 C20 108.31(17) . . ?
C21 C20 C19 102.04(16) . . ?
C21 C20 C15 120.11(15) . . ?
C19 C20 C15 110.04(14) . . ?
C21 C20 H20 108.0 . . ?
C19 C20 H20 108.0 . . ?
C15 C20 H20 108.0 . . ?
C22 C21 C26 119.62(18) . . ?
C22 C21 C20 131.90(18) . . ?
C26 C21 C20 108.36(17) . . ?
C21 C22 C23 117.0(2) . . ?
C21 C22 H22 121.5 . . ?
C23 C22 H22 121.5 . . ?
C24 C23 F1 118.4(2) . . ?
C24 C23 C22 124.1(2) . . ?
F1 C23 C22 117.5(2) . . ?
C23 C24 C25 119.2(2) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 118.1(2) . . ?
C24 C25 H25 121.0 . . ?
C26 C25 H25 121.0 . . ?
C25 C26 C21 121.9(2) . . ?
C25 C26 N3 128.8(2) . . ?
C21 C26 N3 109.26(17) . . ?
C8 N1 C1 108.68(17) . . ?
C8 N1 H1 125.7 . . ?
C1 N1 H1 125.7 . . ?
C11 N2 C10 123.31(17) . . ?
C11 N2 H2A 118.3 . . ?
C10 N2 H2A 118.3 . . ?
C19 N3 C26 112.00(17) . . ?
C19 N3 H3A 124.0 . . ?
C26 N3 H3A 124.0 . . ?
C13 O2 C14 116.16(17) . . ?
C16 O4 C17 117.64(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.86 2.03 2.867(2) 162.9 2_666
N2 H2A O1 0.86 2.07 2.691(2) 128.1 .
N2 H2A O5 0.86 2.63 3.302(2) 135.8 1_455

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.059


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.018 0.000 0.500 410 96 ' '
_platon_squeeze_details          
; 
;
_database_code_depnum_ccdc_archive 'CCDC 1013723'
#######################################################################
#
#                 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_b2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H36 F N3 O6'
_chemical_formula_sum            'C31 H36 F N3 O6'
_chemical_formula_weight         565.63

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.7364(12)
_cell_length_b                   14.951(2)
_cell_length_c                   14.954(2)
_cell_angle_alpha                118.534(4)
_cell_angle_beta                 92.439(5)
_cell_angle_gamma                90.153(4)
_cell_volume                     1517.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7884
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      25.80

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.979
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29606
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.55
_reflns_number_total             7002
_reflns_number_gt                3564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0650P)²+0.9399P] 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         6949
_refine_ls_number_parameters     374
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1687
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.1935
_refine_ls_wR_factor_gt          0.1562
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.021
_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
C1 C 1.3600(4) 0.3760(2) 0.0664(3) 0.0581(8) Uani 1 1 d . . .
C2 C 1.4227(4) 0.3029(2) 0.0901(3) 0.0776(11) Uani 1 1 d . . .
H2 H 1.4725 0.2445 0.0408 0.093 Uiso 1 1 calc R . .
C3 C 1.4100(5) 0.3179(3) 0.1862(4) 0.0890(12) Uani 1 1 d . . .
H3 H 1.4529 0.2697 0.2033 0.107 Uiso 1 1 calc R . .
C4 C 1.3330(5) 0.4052(3) 0.2606(3) 0.0837(11) Uani 1 1 d . . .
C5 C 1.2562(9) 0.4955(5) 0.4342(4) 0.167(3) Uani 1 1 d . . .
H5A H 1.3143 0.5563 0.4433 0.250 Uiso 1 1 calc R . .
H5B H 1.2690 0.4909 0.4960 0.250 Uiso 1 1 calc R . .
H5C H 1.1356 0.4976 0.4176 0.250 Uiso 1 1 calc R . .
C6 C 1.2687(4) 0.4788(2) 0.2387(3) 0.0679(9) Uani 1 1 d . . .
H6 H 1.2172 0.5363 0.2882 0.082 Uiso 1 1 calc R . .
C7 C 1.2832(3) 0.4645(2) 0.1401(2) 0.0520(7) Uani 1 1 d . . .
C8 C 1.2380(3) 0.52473(19) 0.0923(2) 0.0472(7) Uani 1 1 d . . .
C9 C 1.2868(4) 0.4715(2) -0.0056(2) 0.0559(8) Uani 1 1 d . . .
H9 H 1.2734 0.4932 -0.0542 0.067 Uiso 1 1 calc R . .
C10 C 1.1642(4) 0.62900(19) 0.1440(2) 0.0531(7) Uani 1 1 d . . .
H10A H 1.2411 0.6728 0.2016 0.064 Uiso 1 1 calc R . .
H10B H 1.0539 0.6247 0.1704 0.064 Uiso 1 1 calc R . .
C11 C 1.1374(4) 0.67765(18) 0.0768(2) 0.0496(7) Uani 1 1 d . . .
H11A H 1.2392 0.6681 0.0377 0.060 Uiso 1 1 calc R . .
H11B H 1.0397 0.6443 0.0291 0.060 Uiso 1 1 calc R . .
C12 C 0.9554(3) 0.82812(19) 0.13674(19) 0.0437(6) Uani 1 1 d . . .
H12 H 0.8637 0.7836 0.0996 0.052 Uiso 1 1 calc R . .
C13 C 0.9175(3) 0.92973(18) 0.18608(19) 0.0399(6) Uani 1 1 d . . .
C14 C 1.0550(4) 1.00251(19) 0.2415(2) 0.0450(6) Uani 1 1 d . . .
C15 C 1.1448(5) 1.1768(2) 0.3270(3) 0.0923(12) Uani 1 1 d . . .
H15A H 1.1835 1.1745 0.3877 0.138 Uiso 1 1 calc R . .
H15B H 1.0999 1.2427 0.3449 0.138 Uiso 1 1 calc R . .
H15C H 1.2403 1.1643 0.2839 0.138 Uiso 1 1 calc R . .
C16 C 0.7807(8) 0.5326(4) 0.2918(5) 0.1497(16) Uani 1 1 d U . .
H16A H 0.9022 0.5460 0.2920 0.225 Uiso 1 1 calc R . .
H16B H 0.7331 0.4991 0.2229 0.225 Uiso 1 1 calc R . .
H16C H 0.7640 0.4897 0.3224 0.225 Uiso 1 1 calc R . .
C17 C 0.6969(8) 0.6250(4) 0.3477(5) 0.1432(16) Uani 1 1 d U . .
H17A H 0.7277 0.6492 0.4193 0.172 Uiso 1 1 calc R . .
H17B H 0.5733 0.6101 0.3383 0.172 Uiso 1 1 calc R . .
C18 C 0.7294(6) 0.7122(3) 0.3257(4) 0.1059(14) Uani 1 1 d . . .
H18A H 0.8447 0.7405 0.3524 0.127 Uiso 1 1 calc R . .
H18B H 0.7267 0.6855 0.2524 0.127 Uiso 1 1 calc R . .
C19 C 0.6049(5) 0.7946(3) 0.3689(3) 0.0791(10) Uani 1 1 d . . .
H19A H 0.4895 0.7658 0.3431 0.095 Uiso 1 1 calc R . .
H19B H 0.6090 0.8216 0.4422 0.095 Uiso 1 1 calc R . .
C20 C 0.6995(4) 0.9766(2) 0.4166(2) 0.0550(8) Uani 1 1 d . . .
C21 C 0.7614(4) 1.0127(3) 0.5165(3) 0.0695(9) Uani 1 1 d . . .
H21 H 0.7660 0.9706 0.5463 0.083 Uiso 1 1 calc R . .
C22 C 0.8161(5) 1.1138(3) 0.5703(3) 0.0766(10) Uani 1 1 d . . .
H22 H 0.8606 1.1408 0.6371 0.092 Uiso 1 1 calc R . .
C23 C 0.8040(4) 1.1733(3) 0.5244(3) 0.0718(10) Uani 1 1 d . . .
C24 C 0.7426(4) 1.1397(2) 0.4257(2) 0.0619(8) Uani 1 1 d . . .
H24 H 0.7356 1.1831 0.3974 0.074 Uiso 1 1 calc R . .
C25 C 0.6915(3) 1.0379(2) 0.3704(2) 0.0507(7) Uani 1 1 d . . .
C26 C 0.6175(3) 0.97622(19) 0.2633(2) 0.0501(7) Uani 1 1 d . . .
H26 H 0.5089 1.0061 0.2557 0.060 Uiso 1 1 calc R . .
C27 C 0.5777(3) 0.8747(2) 0.2584(2) 0.0529(7) Uani 1 1 d . . .
C28 C 0.7342(3) 0.9603(2) 0.1757(2) 0.0476(7) Uani 1 1 d . . .
H28 H 0.6821 0.9014 0.1154 0.057 Uiso 1 1 calc R . .
C29 C 0.7197(4) 1.0475(2) 0.1520(2) 0.0638(9) Uani 1 1 d . . .
C30 C 0.8109(6) 1.1105(4) 0.0410(3) 0.1023(15) Uani 1 1 d . . .
H30A H 0.6931 1.1330 0.0423 0.123 Uiso 1 1 calc R . .
H30B H 0.8468 1.0812 -0.0286 0.123 Uiso 1 1 calc R . .
C31 C 0.9271(9) 1.1999(4) 0.1086(5) 0.153(2) Uani 1 1 d . . .
H31A H 0.8852 1.2327 0.1761 0.229 Uiso 1 1 calc R . .
H31B H 0.9282 1.2473 0.0823 0.229 Uiso 1 1 calc R . .
H31C H 1.0423 1.1771 0.1106 0.229 Uiso 1 1 calc R . .
F1 F 0.8531(3) 1.27388(15) 0.57992(16) 0.1051(8) Uani 1 1 d . . .
N1 N 1.3585(3) 0.38132(17) -0.0222(2) 0.0642(7) Uani 1 1 d . . .
H1 H 1.3961 0.3358 -0.0790 0.077 Uiso 1 1 calc R . .
N2 N 1.1059(3) 0.78553(15) 0.13530(17) 0.0494(6) Uani 1 1 d . . .
H2A H 1.1912 0.8248 0.1718 0.059 Uiso 1 1 calc R . .
N3 N 0.6315(3) 0.87856(18) 0.3475(2) 0.0579(6) Uani 1 1 d . . .
O1 O 1.3290(5) 0.4103(3) 0.3547(3) 0.1279(11) Uani 1 1 d . . .
O2 O 1.2016(2) 0.98197(14) 0.25811(16) 0.0624(6) Uani 1 1 d . . .
O3 O 1.0107(2) 1.09989(13) 0.27343(15) 0.0598(5) Uani 1 1 d . . .
O4 O 0.6261(3) 1.11852(18) 0.1937(2) 0.0898(8) Uani 1 1 d . . .
O5 O 0.8165(3) 1.03288(17) 0.07418(17) 0.0778(7) Uani 1 1 d . . .
O6 O 0.5085(2) 0.79986(15) 0.18538(16) 0.0648(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.365(4) . ?
C1 C2 1.384(5) . ?
C1 C7 1.409(4) . ?
C2 C3 1.353(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(5) . ?
C3 H3 0.9300 . ?
C4 O1 1.374(5) . ?
C4 C6 1.378(5) . ?
C5 O1 1.402(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.395(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.429(4) . ?
C8 C9 1.361(4) . ?
C8 C10 1.498(3) . ?
C9 N1 1.372(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.504(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.449(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.325(3) . ?
C12 C13 1.374(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.435(4) . ?
C13 C28 1.515(3) . ?
C14 O2 1.222(3) . ?
C14 O3 1.348(3) . ?
C15 O3 1.443(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.405(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.511(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.471(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N3 1.451(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.386(4) . ?
C20 C21 1.386(4) . ?
C20 N3 1.413(4) . ?
C21 C22 1.385(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.360(5) . ?
C22 H22 0.9300 . ?
C23 F1 1.368(4) . ?
C23 C24 1.374(5) . ?
C24 C25 1.387(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.501(4) . ?
C26 C27 1.514(4) . ?
C26 C28 1.546(4) . ?
C26 H26 0.9800 . ?
C27 O6 1.229(3) . ?
C27 N3 1.354(4) . ?
C28 C29 1.509(4) . ?
C28 H28 0.9800 . ?
C29 O4 1.204(3) . ?
C29 O5 1.339(4) . ?
C30 O5 1.464(4) . ?
C30 C31 1.497(7) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?

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
N1 C1 C2 131.0(3) . . ?
N1 C1 C7 107.8(3) . . ?
C2 C1 C7 121.2(4) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O1 C4 C6 124.0(4) . . ?
O1 C4 C3 114.6(4) . . ?
C6 C4 C3 121.4(4) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 118.1(3) . . ?
C4 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C6 C7 C1 119.7(3) . . ?
C6 C7 C8 133.3(3) . . ?
C1 C7 C8 107.0(3) . . ?
C9 C8 C7 106.2(2) . . ?
C9 C8 C10 128.0(3) . . ?
C7 C8 C10 125.6(3) . . ?
C8 C9 N1 110.4(3) . . ?
C8 C9 H9 124.8 . . ?
N1 C9 H9 124.8 . . ?
C8 C10 C11 114.6(2) . . ?
C8 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C8 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 C10 111.9(2) . . ?
N2 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N2 C12 C13 128.2(2) . . ?
N2 C12 H12 115.9 . . ?
C13 C12 H12 115.9 . . ?
C12 C13 C14 118.5(2) . . ?
C12 C13 C28 118.6(2) . . ?
C14 C13 C28 122.8(2) . . ?
O2 C14 O3 120.8(2) . . ?
O2 C14 C13 125.4(2) . . ?
O3 C14 C13 113.7(2) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C16 C17 C18 119.4(5) . . ?
C16 C17 H17A 107.5 . . ?
C18 C17 H17A 107.5 . . ?
C16 C17 H17B 107.5 . . ?
C18 C17 H17B 107.5 . . ?
H17A C17 H17B 107.0 . . ?
C19 C18 C17 114.6(4) . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
N3 C19 C18 115.7(3) . . ?
N3 C19 H19A 108.3 . . ?
C18 C19 H19A 108.3 . . ?
N3 C19 H19B 108.3 . . ?
C18 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C25 C20 C21 122.3(3) . . ?
C25 C20 N3 109.3(3) . . ?
C21 C20 N3 128.4(3) . . ?
C22 C21 C20 117.6(3) . . ?
C22 C21 H21 121.2 . . ?
C20 C21 H21 121.2 . . ?
C23 C22 C21 119.3(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 F1 118.4(3) . . ?
C22 C23 C24 124.3(3) . . ?
F1 C23 C24 117.2(4) . . ?
C23 C24 C25 116.8(3) . . ?
C23 C24 H24 121.6 . . ?
C25 C24 H24 121.6 . . ?
C20 C25 C24 119.7(3) . . ?
C20 C25 C26 108.9(2) . . ?
C24 C25 C26 131.3(3) . . ?
C25 C26 C27 102.0(3) . . ?
C25 C26 C28 117.6(2) . . ?
C27 C26 C28 109.7(2) . . ?
C25 C26 H26 109.1 . . ?
C27 C26 H26 109.1 . . ?
C28 C26 H26 109.1 . . ?
O6 C27 N3 124.7(3) . . ?
O6 C27 C26 126.0(3) . . ?
N3 C27 C26 109.3(2) . . ?
C29 C28 C13 115.0(2) . . ?
C29 C28 C26 110.9(2) . . ?
C13 C28 C26 115.1(2) . . ?
C29 C28 H28 104.8 . . ?
C13 C28 H28 104.8 . . ?
C26 C28 H28 104.8 . . ?
O4 C29 O5 124.1(3) . . ?
O4 C29 C28 124.5(3) . . ?
O5 C29 C28 111.3(2) . . ?
O5 C30 C31 111.0(4) . . ?
O5 C30 H30A 109.4 . . ?
C31 C30 H30A 109.4 . . ?
O5 C30 H30B 109.4 . . ?
C31 C30 H30B 109.4 . . ?
H30A C30 H30B 108.0 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C1 N1 C9 108.6(2) . . ?
C1 N1 H1 125.7 . . ?
C9 N1 H1 125.7 . . ?
C12 N2 C11 124.8(2) . . ?
C12 N2 H2A 117.6 . . ?
C11 N2 H2A 117.6 . . ?
C27 N3 C20 110.5(2) . . ?
C27 N3 C19 122.9(3) . . ?
C20 N3 C19 126.4(3) . . ?
C4 O1 C5 118.6(3) . . ?
C14 O3 C15 116.6(2) . . ?
C29 O5 C30 117.2(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O6 0.86 2.05 2.875(3) 159.8 2_765
N2 H2A O2 0.86 2.07 2.696(3) 129.0 .
N2 H2A O6 0.86 2.50 3.155(3) 133.8 1_655

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.044
#===================================================================
_database_code_depnum_ccdc_archive 'CCDC 1013724'
#######################################################################
#
#                 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_4b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H23 Cl N2 O4'
_chemical_formula_sum            'C28 H23 Cl N2 O4'
_chemical_formula_weight         486.93

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   12.0614(17)
_cell_length_b                   9.0234(13)
_cell_length_c                   22.676(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.047(2)
_cell_angle_gamma                90.00
_cell_volume                     2467.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5075
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016.0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.962
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21008
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.45
_reflns_number_total             5652
_reflns_number_gt                3789
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0591P)²+0.6776P] 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         5634
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C1 C 0.68592(18) 0.4550(2) 0.51715(10) 0.0558(5) Uani 1 1 d . . .
H1 H 0.7335 0.4089 0.4911 0.067 Uiso 1 1 calc R . .
C2 C 0.65121(19) 0.3799(3) 0.56751(11) 0.0637(6) Uani 1 1 d . . .
C3 C 0.6881(2) 0.2224(3) 0.57926(13) 0.0890(9) Uani 1 1 d . . .
H3A H 0.7372 0.2204 0.6131 0.134 Uiso 1 1 calc R . .
H3B H 0.7260 0.1849 0.5455 0.134 Uiso 1 1 calc R . .
H3C H 0.6245 0.1617 0.5867 0.134 Uiso 1 1 calc R . .
C4 C 0.5810(2) 0.4530(3) 0.60538(10) 0.0673(7) Uani 1 1 d . . .
H4 H 0.5585 0.4040 0.6392 0.081 Uiso 1 1 calc R . .
C5 C 0.54241(18) 0.5967(3) 0.59531(9) 0.0612(6) Uani 1 1 d . . .
H5 H 0.4948 0.6432 0.6213 0.073 Uiso 1 1 calc R . .
C6 C 0.57830(16) 0.6671(2) 0.54470(8) 0.0485(5) Uani 1 1 d . . .
C7 C 0.60941(15) 0.8411(2) 0.47330(8) 0.0434(4) Uani 1 1 d . . .
C8 C 0.67055(14) 0.7001(2) 0.45508(7) 0.0418(4) Uani 1 1 d . . .
H8 H 0.6282 0.6594 0.4215 0.050 Uiso 1 1 calc R . .
C9 C 0.64957(15) 0.5972(2) 0.50622(8) 0.0454(4) Uani 1 1 d . . .
C10 C 0.78801(15) 0.7116(2) 0.43521(7) 0.0418(4) Uani 1 1 d . . .
C11 C 0.88650(16) 0.7313(2) 0.47031(8) 0.0513(5) Uani 1 1 d . . .
C12 C 0.89844(18) 0.7659(3) 0.53318(9) 0.0595(5) Uani 1 1 d . . .
C13 C 0.8064(2) 0.8583(3) 0.61669(9) 0.0761(7) Uani 1 1 d . . .
H13A H 0.8248 0.7702 0.6385 0.114 Uiso 1 1 calc R . .
H13B H 0.7339 0.8917 0.6274 0.114 Uiso 1 1 calc R . .
H13C H 0.8598 0.9342 0.6256 0.114 Uiso 1 1 calc R . .
C14 C 0.97458(17) 0.7101(3) 0.43413(9) 0.0605(6) Uani 1 1 d . . .
H14 H 1.0488 0.7153 0.4457 0.073 Uiso 1 1 calc R . .
C15 C 0.82111(15) 0.6798(2) 0.37869(8) 0.0425(4) Uani 1 1 d . . .
C16 C 0.75071(14) 0.6432(2) 0.32688(7) 0.0409(4) Uani 1 1 d . . .
C17 C 0.66945(16) 0.7423(2) 0.30822(8) 0.0483(4) Uani 1 1 d . . .
H17 H 0.6624 0.8326 0.3276 0.058 Uiso 1 1 calc R . .
C18 C 0.59885(17) 0.7094(2) 0.26148(9) 0.0518(5) Uani 1 1 d . . .
H18 H 0.5449 0.7771 0.2494 0.062 Uiso 1 1 calc R . .
C19 C 0.60880(16) 0.5760(2) 0.23292(8) 0.0468(4) Uani 1 1 d . . .
C20 C 0.68821(19) 0.4761(2) 0.25030(10) 0.0615(6) Uani 1 1 d . . .
H20 H 0.6945 0.3860 0.2308 0.074 Uiso 1 1 calc R . .
C21 C 0.75910(18) 0.5097(2) 0.29706(9) 0.0562(5) Uani 1 1 d . . .
H21 H 0.8132 0.4417 0.3086 0.067 Uiso 1 1 calc R . .
C22 C 1.00694(15) 0.6564(2) 0.32887(8) 0.0470(4) Uani 1 1 d . . .
C23 C 0.98367(16) 0.7210(2) 0.27513(9) 0.0513(5) Uani 1 1 d . . .
H23 H 0.9222 0.7825 0.2708 0.062 Uiso 1 1 calc R . .
C24 C 1.05141(16) 0.6951(2) 0.22699(9) 0.0505(5) Uani 1 1 d . . .
H24 H 1.0335 0.7353 0.1903 0.061 Uiso 1 1 calc R . .
C25 C 1.14548(16) 0.6090(2) 0.23448(9) 0.0521(5) Uani 1 1 d . . .
C26 C 1.1879(2) 0.6132(3) 0.13188(10) 0.0865(8) Uani 1 1 d . . .
H26A H 1.1176 0.5684 0.1226 0.130 Uiso 1 1 calc R . .
H26B H 1.2430 0.5755 0.1058 0.130 Uiso 1 1 calc R . .
H26C H 1.1822 0.7187 0.1273 0.130 Uiso 1 1 calc R . .
C27 C 1.17012(17) 0.5483(2) 0.28892(9) 0.0583(5) Uani 1 1 d . . .
H27 H 1.2345 0.4926 0.2941 0.070 Uiso 1 1 calc R . .
C28 C 1.10060(16) 0.5690(2) 0.33588(9) 0.0547(5) Uani 1 1 d . . .
H28 H 1.1166 0.5245 0.3720 0.066 Uiso 1 1 calc R . .
Cl1 Cl 0.51889(5) 0.53542(7) 0.17410(2) 0.06662(19) Uani 1 1 d . . .
N1 N 0.55436(13) 0.81059(18) 0.52376(7) 0.0487(4) Uani 1 1 d . . .
H1A H 0.5104 0.8715 0.5407 0.058 Uiso 1 1 calc R . .
N2 N 0.93665(12) 0.68025(19) 0.37855(7) 0.0509(4) Uani 1 1 d . . .
O1 O 0.60509(11) 0.95801(15) 0.44586(6) 0.0545(4) Uani 1 1 d . . .
O2 O 0.97990(15) 0.7425(3) 0.56326(8) 0.1059(8) Uani 1 1 d . . .
O3 O 0.80708(12) 0.82640(17) 0.55454(6) 0.0593(4) Uani 1 1 d . . .
O4 O 1.21874(13) 0.5796(2) 0.19075(7) 0.0785(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.378(3) . ?
C1 C2 1.398(3) . ?
C1 H1 0.9300 . ?
C2 C4 1.384(3) . ?
C2 C3 1.512(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C9 1.388(3) . ?
C6 N1 1.407(3) . ?
C7 O1 1.226(2) . ?
C7 N1 1.361(2) . ?
C7 C8 1.531(3) . ?
C8 C10 1.498(2) . ?
C8 C9 1.510(2) . ?
C8 H8 0.9800 . ?
C10 C15 1.379(2) . ?
C10 C11 1.429(3) . ?
C11 C14 1.368(3) . ?
C11 C12 1.464(3) . ?
C12 O2 1.205(2) . ?
C12 O3 1.329(2) . ?
C13 O3 1.439(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N2 1.360(2) . ?
C14 H14 0.9300 . ?
C15 N2 1.394(2) . ?
C15 C16 1.475(2) . ?
C16 C21 1.386(3) . ?
C16 C17 1.387(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(3) . ?
C19 Cl1 1.7425(19) . ?
C20 C21 1.383(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.375(3) . ?
C22 C28 1.385(3) . ?
C22 N2 1.438(2) . ?
C23 C24 1.395(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9300 . ?
C25 O4 1.366(2) . ?
C25 C27 1.378(3) . ?
C26 O4 1.412(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.380(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
N1 H1A 0.8600 . ?

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
C9 C1 C2 119.9(2) . . ?
C9 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C4 C2 C1 118.1(2) . . ?
C4 C2 C3 121.3(2) . . ?
C1 C2 C3 120.5(2) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 C5 123.2(2) . . ?
C2 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C6 C5 C4 116.9(2) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C9 C6 C5 121.2(2) . . ?
C9 C6 N1 109.35(16) . . ?
C5 C6 N1 129.4(2) . . ?
O1 C7 N1 125.72(17) . . ?
O1 C7 C8 126.49(16) . . ?
N1 C7 C8 107.67(15) . . ?
C10 C8 C9 116.51(15) . . ?
C10 C8 C7 119.08(15) . . ?
C9 C8 C7 102.42(14) . . ?
C10 C8 H8 105.9 . . ?
C9 C8 H8 105.9 . . ?
C7 C8 H8 105.9 . . ?
C1 C9 C6 120.59(18) . . ?
C1 C9 C8 130.81(18) . . ?
C6 C9 C8 108.56(16) . . ?
C15 C10 C11 106.95(16) . . ?
C15 C10 C8 123.80(16) . . ?
C11 C10 C8 128.48(16) . . ?
C14 C11 C10 107.19(17) . . ?
C14 C11 C12 123.39(18) . . ?
C10 C11 C12 129.42(18) . . ?
O2 C12 O3 122.6(2) . . ?
O2 C12 C11 125.4(2) . . ?
O3 C12 C11 112.02(17) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C11 109.38(18) . . ?
N2 C14 H14 125.3 . . ?
C11 C14 H14 125.3 . . ?
C10 C15 N2 107.94(15) . . ?
C10 C15 C16 127.93(16) . . ?
N2 C15 C16 124.06(15) . . ?
C21 C16 C17 117.97(17) . . ?
C21 C16 C15 122.51(17) . . ?
C17 C16 C15 119.47(16) . . ?
C18 C17 C16 121.22(18) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 119.53(18) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 120.56(18) . . ?
C20 C19 Cl1 120.31(15) . . ?
C18 C19 Cl1 119.13(16) . . ?
C19 C20 C21 119.74(19) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 120.98(19) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C23 C22 C28 119.74(18) . . ?
C23 C22 N2 121.13(17) . . ?
C28 C22 N2 119.12(18) . . ?
C22 C23 C24 120.63(18) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 119.26(19) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
O4 C25 C27 116.20(18) . . ?
O4 C25 C24 124.04(19) . . ?
C27 C25 C24 119.76(18) . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 C28 120.88(19) . . ?
C25 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C28 C22 119.64(19) . . ?
C27 C28 H28 120.2 . . ?
C22 C28 H28 120.2 . . ?
C7 N1 C6 111.68(16) . . ?
C7 N1 H1A 124.2 . . ?
C6 N1 H1A 124.2 . . ?
C14 N2 C15 108.54(16) . . ?
C14 N2 C22 124.22(16) . . ?
C15 N2 C22 127.23(15) . . ?
C12 O3 C13 117.33(17) . . ?
C25 O4 C26 118.80(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86 2.10 2.929(2) 161.6 3_676

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 1022835'
#######################################################################
#
#                 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_zhud140902

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H23 F N2 O4'
_chemical_formula_sum            'C28 H23 F N2 O4'
_chemical_formula_weight         470.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   14.6316(16)
_cell_length_b                   9.0132(9)
_cell_length_c                   21.8076(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.256(6)
_cell_angle_gamma                90.00
_cell_volume                     2377.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8649
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.978
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13293
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3637
_reflns_number_gt                2469
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0453P)²+8.6497P] 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         3637
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.2251
_refine_ls_wR_factor_gt          0.2145
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C1 C 0.7190(4) 1.1284(6) 0.5203(3) 0.0463(13) Uani 1 1 d . . .
C2 C 0.7866(5) 1.2307(6) 0.5732(3) 0.0560(15) Uani 1 1 d . . .
H2 H 0.7635 1.2834 0.5989 0.067 Uiso 1 1 calc R . .
C3 C 0.8906(5) 1.2531(6) 0.5873(3) 0.0593(16) Uani 1 1 d . . .
H3 H 0.9392 1.3206 0.6233 0.071 Uiso 1 1 calc R . .
C4 C 0.9213(5) 1.1747(7) 0.5475(3) 0.0595(16) Uani 1 1 d . . .
C5 C 0.8543(5) 1.0716(7) 0.4944(3) 0.0549(15) Uani 1 1 d . . .
H5 H 0.8776 1.0195 0.4688 0.066 Uiso 1 1 calc R . .
C6 C 0.7516(4) 1.0485(6) 0.4806(3) 0.0432(13) Uani 1 1 d . . .
C7 C 0.6621(4) 0.9402(6) 0.4301(3) 0.0449(13) Uani 1 1 d . . .
H7 H 0.6270 0.9770 0.3793 0.054 Uiso 1 1 calc R . .
C8 C 0.5795(4) 0.9619(7) 0.4510(3) 0.0500(14) Uani 1 1 d . . .
C9 C 0.7004(4) 0.7857(6) 0.4319(3) 0.0416(12) Uani 1 1 d . . .
C10 C 0.6955(4) 0.7218(6) 0.3731(3) 0.0421(12) Uani 1 1 d . . .
C11 C 0.6448(4) 0.7822(6) 0.2972(3) 0.0442(13) Uani 1 1 d . . .
C12 C 0.5355(4) 0.7567(7) 0.2430(3) 0.0552(15) Uani 1 1 d . . .
H12 H 0.4929 0.6989 0.2531 0.066 Uiso 1 1 calc R . .
C13 C 0.4887(5) 0.8173(7) 0.1730(3) 0.0627(17) Uani 1 1 d . . .
H13 H 0.4148 0.7979 0.1365 0.075 Uiso 1 1 calc R . .
C14 C 0.5476(5) 0.9047(6) 0.1560(3) 0.0535(14) Uani 1 1 d . . .
C15 C 0.4964(6) 0.9682(9) 0.0786(3) 0.088(2) Uani 1 1 d . . .
H15A H 0.4204 0.9383 0.0473 0.132 Uiso 1 1 calc R . .
H15B H 0.5359 0.9319 0.0584 0.132 Uiso 1 1 calc R . .
H15C H 0.5007 1.0745 0.0813 0.132 Uiso 1 1 calc R . .
C16 C 0.6560(6) 0.9331(7) 0.2112(3) 0.0684(18) Uani 1 1 d . . .
H16 H 0.6973 0.9951 0.2015 0.082 Uiso 1 1 calc R . .
C17 C 0.7048(5) 0.8714(7) 0.2806(3) 0.0598(16) Uani 1 1 d . . .
H17 H 0.7790 0.8900 0.3167 0.072 Uiso 1 1 calc R . .
C18 C 0.6968(4) 0.4442(6) 0.2847(3) 0.0512(14) Uani 1 1 d . . .
H18 H 0.6255 0.4826 0.2603 0.061 Uiso 1 1 calc R . .
C19 C 0.7230(5) 0.3446(6) 0.2490(3) 0.0542(15) Uani 1 1 d . . .
H19 H 0.6696 0.3169 0.2003 0.065 Uiso 1 1 calc R . .
C20 C 0.8272(5) 0.2865(6) 0.2845(3) 0.0519(14) Uani 1 1 d . . .
C21 C 0.9467(6) 0.1139(10) 0.2795(4) 0.101(3) Uani 1 1 d . . .
H21A H 0.9617 0.0655 0.3234 0.151 Uiso 1 1 calc R . .
H21B H 1.0041 0.1847 0.2926 0.151 Uiso 1 1 calc R . .
H21C H 0.9443 0.0414 0.2463 0.151 Uiso 1 1 calc R . .
C22 C 0.9060(5) 0.3273(8) 0.3559(3) 0.0682(19) Uani 1 1 d . . .
H22 H 0.9768 0.2872 0.3806 0.082 Uiso 1 1 calc R . .
C23 C 0.8794(5) 0.4285(8) 0.3911(3) 0.0669(18) Uani 1 1 d . . .
H23 H 0.9335 0.4575 0.4394 0.080 Uiso 1 1 calc R . .
C24 C 0.7753(4) 0.4871(6) 0.3565(3) 0.0460(13) Uani 1 1 d . . .
C25 C 0.7869(5) 0.5645(6) 0.4689(3) 0.0518(14) Uani 1 1 d . . .
H25 H 0.8247 0.4815 0.4973 0.062 Uiso 1 1 calc R . .
C26 C 0.7588(4) 0.6865(6) 0.4929(3) 0.0450(13) Uani 1 1 d . . .
C27 C 0.7795(5) 0.6926(6) 0.5669(3) 0.0474(13) Uani 1 1 d . . .
C28 C 0.7519(6) 0.8437(8) 0.6448(3) 0.079(2) Uani 1 1 d . . .
H28A H 0.8072 0.7787 0.6823 0.118 Uiso 1 1 calc R . .
H28B H 0.6824 0.8250 0.6384 0.118 Uiso 1 1 calc R . .
H28C H 0.7733 0.9449 0.6597 0.118 Uiso 1 1 calc R . .
F1 F 1.0236(3) 1.1991(4) 0.5624(2) 0.0875(12) Uani 1 1 d . . .
N1 N 0.6140(4) 1.0793(5) 0.4980(2) 0.0516(12) Uani 1 1 d . . .
H1 H 0.5756 1.1188 0.5125 0.062 Uiso 1 1 d R . .
N2 N 0.7500(3) 0.5858(5) 0.3965(2) 0.0461(11) Uani 1 1 d . . .
O1 O 0.4969(3) 0.8876(5) 0.4291(2) 0.0658(12) Uani 1 1 d . . .
O2 O 0.8452(3) 0.1869(5) 0.2445(2) 0.0692(12) Uani 1 1 d . . .
O3 O 0.8280(4) 0.6020(5) 0.6143(2) 0.0852(15) Uani 1 1 d . . .
O4 O 0.7410(4) 0.8176(5) 0.5762(2) 0.0649(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.369(7) . ?
C1 N1 1.398(7) . ?
C1 C6 1.399(7) . ?
C2 C3 1.388(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(8) . ?
C3 H3 0.9300 . ?
C4 F1 1.359(6) . ?
C4 C5 1.374(8) . ?
C5 C6 1.373(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.502(7) . ?
C7 C9 1.494(7) . ?
C7 C8 1.525(7) . ?
C7 H7 0.9800 . ?
C8 O1 1.219(6) . ?
C8 N1 1.358(7) . ?
C9 C10 1.369(7) . ?
C9 C26 1.421(7) . ?
C10 N2 1.393(6) . ?
C10 C11 1.485(7) . ?
C11 C12 1.371(7) . ?
C11 C17 1.381(7) . ?
C12 C13 1.385(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(8) . ?
C13 H13 0.9300 . ?
C14 C16 1.371(8) . ?
C14 C15 1.521(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.377(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C24 1.376(7) . ?
C18 C19 1.378(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(7) . ?
C19 H19 0.9300 . ?
C20 C22 1.366(7) . ?
C20 O2 1.376(6) . ?
C21 O2 1.395(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.381(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(7) . ?
C23 H23 0.9300 . ?
C24 N2 1.434(6) . ?
C25 N2 1.364(6) . ?
C25 C26 1.375(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.466(7) . ?
C27 O3 1.189(6) . ?
C27 O4 1.326(6) . ?
C28 O4 1.432(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
N1 H1 0.8597 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 129.5(5) . . ?
C2 C1 C6 122.2(5) . . ?
N1 C1 C6 108.2(5) . . ?
C1 C2 C3 117.7(5) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 119.5(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
F1 C4 C5 118.6(6) . . ?
F1 C4 C3 118.3(6) . . ?
C5 C4 C3 123.2(6) . . ?
C6 C5 C4 117.5(5) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C1 119.9(5) . . ?
C5 C6 C7 130.8(5) . . ?
C1 C6 C7 109.2(5) . . ?
C9 C7 C6 115.3(4) . . ?
C9 C7 C8 117.4(4) . . ?
C6 C7 C8 102.0(4) . . ?
C9 C7 H7 107.2 . . ?
C6 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
O1 C8 N1 126.1(5) . . ?
O1 C8 C7 126.1(5) . . ?
N1 C8 C7 107.8(5) . . ?
C10 C9 C26 107.4(4) . . ?
C10 C9 C7 123.1(4) . . ?
C26 C9 C7 129.0(4) . . ?
C9 C10 N2 108.0(4) . . ?
C9 C10 C11 128.2(5) . . ?
N2 C10 C11 123.7(4) . . ?
C12 C11 C17 118.5(5) . . ?
C12 C11 C10 120.6(5) . . ?
C17 C11 C10 120.9(5) . . ?
C11 C12 C13 119.8(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 122.1(6) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C16 117.7(5) . . ?
C13 C14 C15 121.8(6) . . ?
C16 C14 C15 120.5(6) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 C17 121.2(6) . . ?
C14 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C11 120.7(6) . . ?
C16 C17 H17 119.7 . . ?
C11 C17 H17 119.7 . . ?
C24 C18 C19 120.4(5) . . ?
C24 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.3(5) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C22 C20 C19 120.0(5) . . ?
C22 C20 O2 123.9(5) . . ?
C19 C20 O2 116.1(5) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 C23 119.3(5) . . ?
C20 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 121.5(5) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C18 118.4(5) . . ?
C23 C24 N2 119.5(5) . . ?
C18 C24 N2 122.0(5) . . ?
N2 C25 C26 108.6(5) . . ?
N2 C25 H25 125.7 . . ?
C26 C25 H25 125.7 . . ?
C25 C26 C9 107.3(4) . . ?
C25 C26 C27 121.8(5) . . ?
C9 C26 C27 130.6(5) . . ?
O3 C27 O4 123.2(5) . . ?
O3 C27 C26 125.8(5) . . ?
O4 C27 C26 111.0(5) . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C8 N1 C1 112.2(4) . . ?
C8 N1 H1 123.9 . . ?
C1 N1 H1 124.0 . . ?
C25 N2 C10 108.6(4) . . ?
C25 N2 C24 123.2(5) . . ?
C10 N2 C24 127.9(4) . . ?
C20 O2 C21 119.1(5) . . ?
C27 O4 C28 119.5(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.07 2.855(6) 151.7 3_676

_diffrn_measured_fraction_theta_max 0.867
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.867
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 1022862'
