# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a
_audit_block_doi                 10.5517/cc13rk3j
_database_code_depnum_ccdc_archive 'CCDC 1035527'
_audit_update_record             
;
2014-11-24 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H33 Cl N2 O6'
_chemical_formula_sum            'C34 H33 Cl N2 O6'
_chemical_formula_weight         601.07

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                   11.4719(17)
_cell_length_b                   12.6980(19)
_cell_length_c                   13.0030(18)
_cell_angle_alpha                104.987(4)
_cell_angle_beta                 106.388(4)
_cell_angle_gamma                111.648(4)
_cell_volume                     1543.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5535
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      22.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.963
_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            23556
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0890
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.57
_reflns_number_total             7130
_reflns_number_gt                3449
_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)+(0.1048P)²+0.4756P] 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         7079
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1682
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2296
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 1.4259(4) 0.9916(4) 0.2908(3) 0.0704(11) Uani 1 1 d . . .
H1 H 1.3737 0.9131 0.2862 0.084 Uiso 1 1 calc R . .
C2 C 1.5438(4) 1.0750(5) 0.3901(4) 0.0858(13) Uani 1 1 d . . .
H2 H 1.5720 1.0522 0.4513 0.103 Uiso 1 1 calc R . .
C3 C 1.6192(4) 1.1903(4) 0.3997(4) 0.0936(14) Uani 1 1 d . . .
H3 H 1.6992 1.2474 0.4674 0.112 Uiso 1 1 calc R . .
C4 C 1.5777(5) 1.2218(4) 0.3105(5) 0.126(2) Uani 1 1 d . . .
H4 H 1.6288 1.3013 0.3166 0.151 Uiso 1 1 calc R . .
C5 C 1.4594(4) 1.1369(4) 0.2095(4) 0.1078(18) Uani 1 1 d . . .
H5 H 1.4321 1.1601 0.1485 0.129 Uiso 1 1 calc R . .
C6 C 1.3831(3) 1.0211(3) 0.1979(3) 0.0549(9) Uani 1 1 d . . .
C7 C 1.2568(3) 0.9271(3) 0.0852(3) 0.0588(9) Uani 1 1 d . . .
H7A H 1.2353 0.9693 0.0361 0.071 Uiso 1 1 calc R . .
H7B H 1.2783 0.8669 0.0435 0.071 Uiso 1 1 calc R . .
C8 C 1.0842(3) 0.7412(3) 0.0874(2) 0.0423(7) Uani 1 1 d . . .
C9 C 0.9509(3) 0.7022(3) 0.1048(2) 0.0395(7) Uani 1 1 d . . .
C10 C 0.9384(3) 0.8203(3) 0.1300(2) 0.0440(8) Uani 1 1 d . . .
C11 C 0.8390(4) 0.8467(3) 0.1524(3) 0.0558(9) Uani 1 1 d . . .
H11 H 0.7646 0.7879 0.1564 0.067 Uiso 1 1 calc R . .
C12 C 0.8550(4) 0.9651(4) 0.1687(3) 0.0644(10) Uani 1 1 d . . .
C13 C 0.9666(5) 1.0535(4) 0.1662(3) 0.0699(11) Uani 1 1 d . . .
H13 H 0.9741 1.1315 0.1772 0.084 Uiso 1 1 calc R . .
C14 C 1.0682(4) 1.0282(3) 0.1475(3) 0.0611(10) Uani 1 1 d . . .
H14 H 1.1452 1.0883 0.1474 0.073 Uiso 1 1 calc R . .
C15 C 1.0510(3) 0.9110(3) 0.1290(2) 0.0491(8) Uani 1 1 d . . .
C16 C 0.8272(3) 0.5855(3) -0.0032(2) 0.0409(7) Uani 1 1 d . . .
H16 H 0.8550 0.5210 -0.0206 0.049 Uiso 1 1 calc R . .
C17 C 0.7798(3) 0.6076(3) -0.1138(2) 0.0461(8) Uani 1 1 d . . .
C18 C 0.6595(3) 0.5019(3) -0.2208(2) 0.0454(8) Uani 1 1 d . . .
C19 C 0.5800(3) 0.5278(3) -0.3023(3) 0.0580(9) Uani 1 1 d . . .
H19 H 0.6031 0.6098 -0.2898 0.070 Uiso 1 1 calc R . .
C20 C 0.4661(4) 0.4322(4) -0.4027(3) 0.0650(10) Uani 1 1 d . . .
H20 H 0.4128 0.4513 -0.4555 0.078 Uiso 1 1 calc R . .
C21 C 0.4306(4) 0.3102(4) -0.4255(3) 0.0664(10) Uani 1 1 d . . .
C22 C 0.3069(4) 0.2058(5) -0.5353(4) 0.1085(17) Uani 1 1 d . . .
H22A H 0.2352 0.1625 -0.5145 0.163 Uiso 1 1 calc R . .
H22B H 0.3340 0.1494 -0.5733 0.163 Uiso 1 1 calc R . .
H22C H 0.2733 0.2396 -0.5878 0.163 Uiso 1 1 calc R . .
C23 C 0.5115(4) 0.2855(3) -0.3444(3) 0.0699(10) Uani 1 1 d . . .
H23 H 0.4899 0.2035 -0.3584 0.084 Uiso 1 1 calc R . .
C24 C 0.6232(3) 0.3784(3) -0.2437(3) 0.0557(9) Uani 1 1 d . . .
H24 H 0.6748 0.3585 -0.1904 0.067 Uiso 1 1 calc R . .
C25 C 0.7185(3) 0.5451(3) 0.0456(2) 0.0469(8) Uani 1 1 d . . .
H25 H 0.6596 0.5835 0.0281 0.056 Uiso 1 1 calc R . .
C26 C 0.6269(3) 0.4094(3) 0.0129(3) 0.0636(10) Uani 1 1 d . . .
H26A H 0.6733 0.3608 -0.0020 0.076 Uiso 1 1 calc R . .
H26B H 0.5410 0.3755 -0.0554 0.076 Uiso 1 1 calc R . .
C27 C 0.6023(4) 0.4142(4) 0.1226(3) 0.0880(13) Uani 1 1 d . . .
H27A H 0.5303 0.4369 0.1227 0.106 Uiso 1 1 calc R . .
H27B H 0.5759 0.3346 0.1281 0.106 Uiso 1 1 calc R . .
C28 C 0.7375(4) 0.5109(4) 0.2208(3) 0.0811(13) Uani 1 1 d . . .
H28A H 0.7243 0.5510 0.2876 0.097 Uiso 1 1 calc R . .
H28B H 0.7958 0.4746 0.2450 0.097 Uiso 1 1 calc R . .
C29 C 0.9477(3) 0.6555(3) 0.2052(2) 0.0432(7) Uani 1 1 d . . .
C30 C 1.0379(4) 0.7673(3) 0.3238(3) 0.0486(8) Uani 1 1 d . . .
C31 C 1.0614(5) 0.8817(4) 0.5074(3) 0.0889(13) Uani 1 1 d . . .
H31A H 1.1253 0.8573 0.5454 0.133 Uiso 1 1 calc R . .
H31B H 1.0069 0.8893 0.5502 0.133 Uiso 1 1 calc R . .
H31C H 1.1115 0.9601 0.5054 0.133 Uiso 1 1 calc R . .
C32 C 1.0100(3) 0.5656(3) 0.2048(3) 0.0469(8) Uani 1 1 d . . .
H32A H 0.9480 0.4890 0.1353 0.056 Uiso 1 1 calc R . .
H32B H 1.0970 0.6021 0.1985 0.056 Uiso 1 1 calc R . .
C33 C 1.0353(3) 0.5349(3) 0.3093(3) 0.0496(8) Uani 1 1 d . . .
C34 C 1.0757(7) 0.3955(5) 0.3817(4) 0.136(2) Uani 1 1 d . . .
H34A H 1.1497 0.4676 0.4494 0.205 Uiso 1 1 calc R . .
H34B H 1.1048 0.3341 0.3623 0.205 Uiso 1 1 calc R . .
H34C H 0.9967 0.3624 0.3984 0.205 Uiso 1 1 calc R . .
Cl1 Cl 0.72729(14) 0.99819(12) 0.18987(10) 0.0989(5) Uani 1 1 d . . .
N1 N 1.1361(2) 0.8623(2) 0.1032(2) 0.0467(6) Uani 1 1 d . . .
N2 N 0.7999(2) 0.5997(3) 0.1753(2) 0.0517(7) Uani 1 1 d . . .
O1 O 1.1347(2) 0.67528(19) 0.05906(18) 0.0503(6) Uani 1 1 d . . .
O2 O 0.8371(3) 0.7076(2) -0.11572(19) 0.0694(7) Uani 1 1 d . . .
O3 O 1.1595(3) 0.8292(2) 0.35300(19) 0.0620(6) Uani 1 1 d . . .
O4 O 0.9706(2) 0.7882(2) 0.38764(19) 0.0632(7) Uani 1 1 d . . .
O5 O 1.0531(3) 0.5952(2) 0.4056(2) 0.0672(7) Uani 1 1 d . . .
O6 O 1.0395(3) 0.4291(3) 0.2841(2) 0.0906(9) 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 1.367(5) . ?
C1 C6 1.369(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.348(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.343(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.346(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.514(4) . ?
C7 N1 1.446(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.222(3) . ?
C8 N1 1.361(4) . ?
C8 C9 1.526(4) . ?
C9 C10 1.519(4) . ?
C9 C16 1.559(4) . ?
C9 C29 1.571(4) . ?
C10 C15 1.384(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.396(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(6) . ?
C12 Cl1 1.738(4) . ?
C13 C14 1.385(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(5) . ?
C14 H14 0.9300 . ?
C15 N1 1.404(4) . ?
C16 C17 1.525(4) . ?
C16 C25 1.537(4) . ?
C16 H16 0.9800 . ?
C17 O2 1.206(4) . ?
C17 C18 1.493(4) . ?
C18 C19 1.385(4) . ?
C18 C24 1.389(4) . ?
C19 C20 1.390(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(5) . ?
C20 H20 0.9300 . ?
C21 C23 1.381(5) . ?
C21 C22 1.516(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.374(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.492(4) . ?
C25 C26 1.513(5) . ?
C25 H25 0.9800 . ?
C26 C27 1.521(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.487(5) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 N2 1.457(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 N2 1.458(4) . ?
C29 C30 1.532(4) . ?
C29 C32 1.555(4) . ?
C30 O3 1.202(4) . ?
C30 O4 1.325(4) . ?
C31 O4 1.462(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.488(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 O5 1.201(4) . ?
C33 O6 1.320(4) . ?
C34 O6 1.441(5) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.5(4) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 117.4(3) . . ?
C5 C6 C7 120.9(3) . . ?
C1 C6 C7 121.7(3) . . ?
N1 C7 C6 113.7(3) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 N1 124.6(3) . . ?
O1 C8 C9 126.7(3) . . ?
N1 C8 C9 108.6(3) . . ?
C10 C9 C8 101.8(2) . . ?
C10 C9 C16 115.8(2) . . ?
C8 C9 C16 111.7(2) . . ?
C10 C9 C29 111.3(2) . . ?
C8 C9 C29 116.6(2) . . ?
C16 C9 C29 100.3(2) . . ?
C15 C10 C11 120.1(3) . . ?
C15 C10 C9 108.7(3) . . ?
C11 C10 C9 131.2(3) . . ?
C10 C11 C12 117.4(3) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C13 C12 C11 121.7(4) . . ?
C13 C12 Cl1 120.1(3) . . ?
C11 C12 Cl1 118.3(3) . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 117.4(4) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C14 C15 C10 122.5(3) . . ?
C14 C15 N1 127.7(3) . . ?
C10 C15 N1 109.7(3) . . ?
C17 C16 C25 115.2(2) . . ?
C17 C16 C9 114.5(2) . . ?
C25 C16 C9 102.2(2) . . ?
C17 C16 H16 108.2 . . ?
C25 C16 H16 108.2 . . ?
C9 C16 H16 108.2 . . ?
O2 C17 C18 120.3(3) . . ?
O2 C17 C16 121.4(3) . . ?
C18 C17 C16 118.3(3) . . ?
C19 C18 C24 118.0(3) . . ?
C19 C18 C17 118.5(3) . . ?
C24 C18 C17 123.4(3) . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C23 117.5(3) . . ?
C20 C21 C22 121.6(4) . . ?
C23 C21 C22 120.9(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 122.0(4) . . ?
C24 C23 H23 119.0 . . ?
C21 C23 H23 119.0 . . ?
C23 C24 C18 120.5(3) . . ?
C23 C24 H24 119.8 . . ?
C18 C24 H24 119.8 . . ?
N2 C25 C26 105.2(2) . . ?
N2 C25 C16 104.7(2) . . ?
C26 C25 C16 121.0(3) . . ?
N2 C25 H25 108.5 . . ?
C26 C25 H25 108.5 . . ?
C16 C25 H25 108.5 . . ?
C25 C26 C27 101.6(3) . . ?
C25 C26 H26A 111.5 . . ?
C27 C26 H26A 111.5 . . ?
C25 C26 H26B 111.5 . . ?
C27 C26 H26B 111.5 . . ?
H26A C26 H26B 109.3 . . ?
C28 C27 C26 104.2(3) . . ?
C28 C27 H27A 110.9 . . ?
C26 C27 H27A 110.9 . . ?
C28 C27 H27B 110.9 . . ?
C26 C27 H27B 110.9 . . ?
H27A C27 H27B 108.9 . . ?
N2 C28 C27 105.8(3) . . ?
N2 C28 H28A 110.6 . . ?
C27 C28 H28A 110.6 . . ?
N2 C28 H28B 110.6 . . ?
C27 C28 H28B 110.6 . . ?
H28A C28 H28B 108.7 . . ?
N2 C29 C30 114.5(3) . . ?
N2 C29 C32 115.3(3) . . ?
C30 C29 C32 106.5(2) . . ?
N2 C29 C9 99.9(2) . . ?
C30 C29 C9 108.7(2) . . ?
C32 C29 C9 111.8(2) . . ?
O3 C30 O4 124.6(3) . . ?
O3 C30 C29 120.9(3) . . ?
O4 C30 C29 114.6(3) . . ?
O4 C31 H31A 109.5 . . ?
O4 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O4 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C29 115.6(3) . . ?
C33 C32 H32A 108.4 . . ?
C29 C32 H32A 108.4 . . ?
C33 C32 H32B 108.4 . . ?
C29 C32 H32B 108.4 . . ?
H32A C32 H32B 107.5 . . ?
O5 C33 O6 122.0(3) . . ?
O5 C33 C32 127.4(3) . . ?
O6 C33 C32 110.6(3) . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C8 N1 C15 111.2(3) . . ?
C8 N1 C7 123.4(3) . . ?
C15 N1 C7 125.2(3) . . ?
C28 N2 C29 120.9(3) . . ?
C28 N2 C25 108.5(3) . . ?
C29 N2 C25 110.6(2) . . ?
C30 O4 C31 113.6(3) . . ?
C33 O6 C34 115.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a'
_audit_block_doi                 10.5517/cc13rk4k
_database_code_depnum_ccdc_archive 'CCDC 1035528'
_audit_update_record             
;
2014-11-24 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H33 Cl N2 O6'
_chemical_formula_sum            'C34 H33 Cl N2 O6'
_chemical_formula_weight         601.07

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   12.300(2)
_cell_length_b                   9.3444(17)
_cell_length_c                   27.632(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.945(7)
_cell_angle_gamma                90.00
_cell_volume                     3068.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2232
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      19.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.963
_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            26143
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0997
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         27.55
_reflns_number_total             7069
_reflns_number_gt                3488
_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)+(0.0548P)²+1.0889P] 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     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1657
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1334
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.6627(3) 0.4321(4) 1.06153(13) 0.0600(11) Uani 1 1 d . . .
H1 H 0.6189 0.4893 1.0364 0.072 Uiso 1 1 calc R . .
C2 C 0.6115(4) 0.3529(5) 1.09220(17) 0.0798(14) Uani 1 1 d . . .
H2 H 0.5338 0.3564 1.0872 0.096 Uiso 1 1 calc R . .
C3 C 0.6762(4) 0.2692(5) 1.13010(17) 0.0790(13) Uani 1 1 d . . .
H3 H 0.6424 0.2152 1.1505 0.095 Uiso 1 1 calc R . .
C4 C 0.7910(4) 0.2666(4) 1.13731(15) 0.0675(12) Uani 1 1 d . . .
H4 H 0.8351 0.2120 1.1632 0.081 Uiso 1 1 calc R . .
C5 C 0.8413(3) 0.3441(4) 1.10661(13) 0.0495(9) Uani 1 1 d . . .
H5 H 0.9191 0.3409 1.1118 0.059 Uiso 1 1 calc R . .
C6 C 0.7774(3) 0.4267(3) 1.06805(11) 0.0364(8) Uani 1 1 d . . .
C7 C 0.8324(3) 0.5099(3) 1.03410(11) 0.0410(8) Uani 1 1 d . . .
H7A H 0.8014 0.6059 1.0298 0.049 Uiso 1 1 calc R . .
H7B H 0.9124 0.5176 1.0497 0.049 Uiso 1 1 calc R . .
C8 C 0.7353(3) 0.4872(4) 0.94309(11) 0.0351(7) Uani 1 1 d . . .
C9 C 0.7329(2) 0.3763(3) 0.90082(10) 0.0318(7) Uani 1 1 d . . .
C10 C 0.8366(2) 0.2895(3) 0.92336(10) 0.0321(7) Uani 1 1 d . . .
C11 C 0.8922(3) 0.1875(3) 0.90279(11) 0.0368(8) Uani 1 1 d . . .
H11 H 0.8657 0.1606 0.8694 0.044 Uiso 1 1 calc R . .
C12 C 0.9885(3) 0.1262(3) 0.93294(12) 0.0382(8) Uani 1 1 d . . .
C13 C 1.0288(3) 0.1644(4) 0.98255(12) 0.0422(8) Uani 1 1 d . . .
H13 H 1.0927 0.1198 1.0021 0.051 Uiso 1 1 calc R . .
C14 C 0.9753(3) 0.2678(3) 1.00330(11) 0.0381(8) Uani 1 1 d . . .
H14 H 1.0026 0.2947 1.0366 0.046 Uiso 1 1 calc R . .
C15 C 0.8798(2) 0.3308(3) 0.97329(10) 0.0309(7) Uani 1 1 d . . .
C16 C 0.7266(2) 0.4429(3) 0.84897(10) 0.0347(7) Uani 1 1 d . . .
H16 H 0.7416 0.3666 0.8272 0.042 Uiso 1 1 calc R . .
C17 C 0.8124(3) 0.5597(3) 0.85061(11) 0.0382(8) Uani 1 1 d . . .
C18 C 0.8286(3) 0.6223(3) 0.80344(11) 0.0372(8) Uani 1 1 d . . .
C19 C 0.7954(3) 0.5543(4) 0.75744(12) 0.0484(9) Uani 1 1 d . . .
H19 H 0.7592 0.4662 0.7549 0.058 Uiso 1 1 calc R . .
C20 C 0.8159(3) 0.6171(4) 0.71510(13) 0.0588(11) Uani 1 1 d . . .
H20 H 0.7939 0.5696 0.6845 0.071 Uiso 1 1 calc R . .
C21 C 0.8682(3) 0.7480(5) 0.71743(14) 0.0566(10) Uani 1 1 d . . .
C22 C 0.8891(4) 0.8168(5) 0.67117(16) 0.0925(16) Uani 1 1 d . . .
H22A H 0.8551 0.7598 0.6423 0.139 Uiso 1 1 calc R . .
H22B H 0.9686 0.8234 0.6747 0.139 Uiso 1 1 calc R . .
H22C H 0.8568 0.9109 0.6671 0.139 Uiso 1 1 calc R . .
C23 C 0.9007(3) 0.8151(4) 0.76356(14) 0.0587(10) Uani 1 1 d . . .
H23 H 0.9362 0.9037 0.7659 0.070 Uiso 1 1 calc R . .
C24 C 0.8820(3) 0.7543(4) 0.80594(12) 0.0491(9) Uani 1 1 d . . .
H24 H 0.9051 0.8016 0.8365 0.059 Uiso 1 1 calc R . .
C25 C 0.6032(3) 0.4866(4) 0.82947(11) 0.0431(8) Uani 1 1 d . . .
H25 H 0.5946 0.5858 0.8394 0.052 Uiso 1 1 calc R . .
C26 C 0.5420(3) 0.4684(5) 0.77449(12) 0.0656(12) Uani 1 1 d . . .
H26A H 0.5716 0.3879 0.7597 0.079 Uiso 1 1 calc R . .
H26B H 0.5471 0.5542 0.7555 0.079 Uiso 1 1 calc R . .
C27 C 0.4214(3) 0.4409(5) 0.77691(14) 0.0731(13) Uani 1 1 d . . .
H27A H 0.3841 0.5296 0.7814 0.088 Uiso 1 1 calc R . .
H27B H 0.3784 0.3937 0.7468 0.088 Uiso 1 1 calc R . .
C28 C 0.4354(3) 0.3445(4) 0.82223(12) 0.0550(10) Uani 1 1 d . . .
H28A H 0.3735 0.3566 0.8376 0.066 Uiso 1 1 calc R . .
H28B H 0.4393 0.2448 0.8130 0.066 Uiso 1 1 calc R . .
C29 C 0.6166(2) 0.2929(3) 0.89018(10) 0.0330(7) Uani 1 1 d . . .
C30 C 0.6343(3) 0.1499(3) 0.86577(12) 0.0395(8) Uani 1 1 d . . .
C31 C 0.6739(4) -0.0961(4) 0.87910(17) 0.0851(15) Uani 1 1 d . . .
H31A H 0.6074 -0.1227 0.8539 0.128 Uiso 1 1 calc R . .
H31B H 0.6880 -0.1653 0.9057 0.128 Uiso 1 1 calc R . .
H31C H 0.7369 -0.0928 0.8646 0.128 Uiso 1 1 calc R . .
C32 C 0.5785(3) 0.2688(4) 0.93814(11) 0.0399(8) Uani 1 1 d . . .
H32A H 0.6399 0.2252 0.9630 0.048 Uiso 1 1 calc R . .
H32B H 0.5635 0.3612 0.9511 0.048 Uiso 1 1 calc R . .
C33 C 0.4756(3) 0.1765(4) 0.93202(13) 0.0453(9) Uani 1 1 d . . .
C34 C 0.3459(4) 0.0894(5) 0.97475(17) 0.0898(16) Uani 1 1 d . . .
H34A H 0.2811 0.1330 0.9527 0.135 Uiso 1 1 calc R . .
H34B H 0.3360 0.0855 1.0081 0.135 Uiso 1 1 calc R . .
H34C H 0.3550 -0.0059 0.9634 0.135 Uiso 1 1 calc R . .
Cl1 Cl 1.05861(8) -0.00456(10) 0.90751(4) 0.0585(3) Uani 1 1 d . . .
N1 N 0.8157(2) 0.4425(3) 0.98469(8) 0.0340(6) Uani 1 1 d . . .
N2 N 0.5424(2) 0.3913(3) 0.85633(9) 0.0379(7) Uani 1 1 d . . .
O1 O 0.67411(19) 0.5898(2) 0.94138(8) 0.0463(6) Uani 1 1 d . . .
O2 O 0.8684(2) 0.6036(3) 0.89105(8) 0.0576(7) Uani 1 1 d . . .
O3 O 0.6338(2) 0.1362(3) 0.82238(8) 0.0543(7) Uani 1 1 d . . .
O4 O 0.6577(2) 0.0432(2) 0.89887(8) 0.0535(7) Uani 1 1 d . . .
O5 O 0.4263(2) 0.1138(3) 0.89531(10) 0.0747(9) Uani 1 1 d . . .
O6 O 0.4453(2) 0.1734(3) 0.97486(9) 0.0668(8) 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 C6 1.377(5) . ?
C1 C2 1.392(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(4) . ?
C7 N1 1.469(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.212(4) . ?
C8 N1 1.374(4) . ?
C8 C9 1.556(4) . ?
C9 C10 1.504(4) . ?
C9 C16 1.545(4) . ?
C9 C29 1.588(4) . ?
C10 C11 1.379(4) . ?
C10 C15 1.399(4) . ?
C11 C12 1.384(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(4) . ?
C12 Cl1 1.745(3) . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9300 . ?
C15 N1 1.392(4) . ?
C16 C17 1.511(4) . ?
C16 C25 1.529(4) . ?
C16 H16 0.9800 . ?
C17 O2 1.222(3) . ?
C17 C18 1.488(4) . ?
C18 C19 1.385(4) . ?
C18 C24 1.390(4) . ?
C19 C20 1.389(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(5) . ?
C20 H20 0.9300 . ?
C21 C23 1.384(5) . ?
C21 C22 1.511(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.374(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.480(4) . ?
C25 C26 1.522(4) . ?
C25 H25 0.9800 . ?
C26 C27 1.523(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.516(5) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 N2 1.473(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 N2 1.454(4) . ?
C29 C32 1.532(4) . ?
C29 C30 1.537(4) . ?
C30 O3 1.204(3) . ?
C30 O4 1.334(4) . ?
C31 O4 1.445(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.504(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 O5 1.193(4) . ?
C33 O6 1.330(4) . ?
C34 O6 1.452(4) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.6(4) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 C7 120.6(3) . . ?
C5 C6 C7 120.6(3) . . ?
N1 C7 C6 112.3(2) . . ?
N1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
O1 C8 N1 125.4(3) . . ?
O1 C8 C9 127.3(3) . . ?
N1 C8 C9 107.2(3) . . ?
C10 C9 C16 115.8(3) . . ?
C10 C9 C8 101.4(2) . . ?
C16 C9 C8 114.5(2) . . ?
C10 C9 C29 116.0(2) . . ?
C16 C9 C29 101.5(2) . . ?
C8 C9 C29 107.9(2) . . ?
C11 C10 C15 119.6(3) . . ?
C11 C10 C9 131.3(3) . . ?
C15 C10 C9 109.0(3) . . ?
C10 C11 C12 118.5(3) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 121.6(3) . . ?
C13 C12 Cl1 119.6(2) . . ?
C11 C12 Cl1 118.9(2) . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 118.2(3) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C14 C15 N1 128.8(3) . . ?
C14 C15 C10 121.5(3) . . ?
N1 C15 C10 109.6(2) . . ?
C17 C16 C25 116.1(3) . . ?
C17 C16 C9 113.3(2) . . ?
C25 C16 C9 104.0(2) . . ?
C17 C16 H16 107.7 . . ?
C25 C16 H16 107.7 . . ?
C9 C16 H16 107.7 . . ?
O2 C17 C18 119.9(3) . . ?
O2 C17 C16 119.6(3) . . ?
C18 C17 C16 120.5(3) . . ?
C19 C18 C24 118.4(3) . . ?
C19 C18 C17 123.3(3) . . ?
C24 C18 C17 118.2(3) . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C23 117.8(3) . . ?
C20 C21 C22 121.2(4) . . ?
C23 C21 C22 121.0(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 121.7(4) . . ?
C24 C23 H23 119.2 . . ?
C21 C23 H23 119.2 . . ?
C23 C24 C18 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C18 C24 H24 119.8 . . ?
N2 C25 C26 104.4(3) . . ?
N2 C25 C16 104.3(2) . . ?
C26 C25 C16 120.9(3) . . ?
N2 C25 H25 108.9 . . ?
C26 C25 H25 108.9 . . ?
C16 C25 H25 108.9 . . ?
C25 C26 C27 102.3(3) . . ?
C25 C26 H26A 111.3 . . ?
C27 C26 H26A 111.3 . . ?
C25 C26 H26B 111.3 . . ?
C27 C26 H26B 111.3 . . ?
H26A C26 H26B 109.2 . . ?
C28 C27 C26 103.4(3) . . ?
C28 C27 H27A 111.1 . . ?
C26 C27 H27A 111.1 . . ?
C28 C27 H27B 111.1 . . ?
C26 C27 H27B 111.1 . . ?
H27A C27 H27B 109.0 . . ?
N2 C28 C27 104.1(3) . . ?
N2 C28 H28A 110.9 . . ?
C27 C28 H28A 110.9 . . ?
N2 C28 H28B 110.9 . . ?
C27 C28 H28B 110.9 . . ?
H28A C28 H28B 108.9 . . ?
N2 C29 C32 111.5(3) . . ?
N2 C29 C30 113.8(2) . . ?
C32 C29 C30 111.2(2) . . ?
N2 C29 C9 101.2(2) . . ?
C32 C29 C9 112.0(2) . . ?
C30 C29 C9 106.6(2) . . ?
O3 C30 O4 123.2(3) . . ?
O3 C30 C29 124.4(3) . . ?
O4 C30 C29 112.3(3) . . ?
O4 C31 H31A 109.5 . . ?
O4 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O4 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C29 115.0(3) . . ?
C33 C32 H32A 108.5 . . ?
C29 C32 H32A 108.5 . . ?
C33 C32 H32B 108.5 . . ?
C29 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
O5 C33 O6 123.2(3) . . ?
O5 C33 C32 127.3(3) . . ?
O6 C33 C32 109.4(3) . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C8 N1 C15 111.5(2) . . ?
C8 N1 C7 123.0(3) . . ?
C15 N1 C7 125.5(2) . . ?
C29 N2 C28 122.2(3) . . ?
C29 N2 C25 112.8(2) . . ?
C28 N2 C25 110.0(2) . . ?
C30 O4 C31 116.2(3) . . ?
C33 O6 C34 116.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.065
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2a
_audit_block_doi                 10.5517/cc13rk5l
_database_code_depnum_ccdc_archive 'CCDC 1035529'
_audit_update_record             
;
2014-11-24 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H28 Cl2 N2 O6'
_chemical_formula_sum            'C31 H28 Cl2 N2 O6'
_chemical_formula_weight         595.45

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                   11.583(2)
_cell_length_b                   11.842(2)
_cell_length_c                   12.658(2)
_cell_angle_alpha                101.756(5)
_cell_angle_beta                 108.305(5)
_cell_angle_gamma                110.254(5)
_cell_volume                     1448.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3373
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      21.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.952
_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            20872
_diffrn_reflns_av_R_equivalents  0.1064
_diffrn_reflns_av_sigmaI/netI    0.1887
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         27.52
_reflns_number_total             6674
_reflns_number_gt                2637
_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)+(0.0627P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6536
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2263
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1551
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_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 0.1847(3) 0.5719(4) -0.1010(3) 0.0647(11) Uani 1 1 d . . .
H1 H 0.1969 0.6185 -0.1507 0.078 Uiso 1 1 calc R . .
C2 C 0.1422(4) 0.4409(5) -0.1427(4) 0.0834(14) Uani 1 1 d . . .
H2 H 0.1266 0.4000 -0.2202 0.100 Uiso 1 1 calc R . .
C3 C 0.1229(4) 0.3706(4) -0.0713(5) 0.0815(14) Uani 1 1 d . . .
H3 H 0.0952 0.2824 -0.0997 0.098 Uiso 1 1 calc R . .
C4 C 0.1446(4) 0.4306(5) 0.0413(4) 0.0835(13) Uani 1 1 d . . .
H4 H 0.1297 0.3832 0.0900 0.100 Uiso 1 1 calc R . .
C5 C 0.1888(4) 0.5623(4) 0.0839(3) 0.0679(11) Uani 1 1 d . . .
H5 H 0.2051 0.6027 0.1618 0.082 Uiso 1 1 calc R . .
C6 C 0.2090(3) 0.6340(3) 0.0136(3) 0.0427(9) Uani 1 1 d . . .
C7 C 0.2585(3) 0.7775(3) 0.0623(3) 0.0474(9) Uani 1 1 d . . .
H7A H 0.2456 0.8096 -0.0030 0.057 Uiso 1 1 calc R . .
H7B H 0.2046 0.7961 0.1023 0.057 Uiso 1 1 calc R . .
C8 C 0.4445(3) 0.8820(3) 0.2655(3) 0.0353(8) Uani 1 1 d . . .
C9 C 0.6006(3) 0.9401(3) 0.3231(2) 0.0310(7) Uani 1 1 d . . .
C10 C 0.6319(3) 0.9309(3) 0.2154(2) 0.0307(7) Uani 1 1 d . . .
C11 C 0.7525(3) 0.9657(3) 0.2046(3) 0.0368(8) Uani 1 1 d . . .
H11 H 0.8344 1.0027 0.2716 0.044 Uiso 1 1 calc R . .
C12 C 0.7497(3) 0.9446(3) 0.0922(3) 0.0423(9) Uani 1 1 d . . .
C13 C 0.6293(4) 0.8911(3) -0.0081(3) 0.0509(10) Uani 1 1 d . . .
H13 H 0.6302 0.8800 -0.0826 0.061 Uiso 1 1 calc R . .
C14 C 0.5070(3) 0.8536(3) 0.0021(3) 0.0465(9) Uani 1 1 d . . .
H14 H 0.4250 0.8164 -0.0648 0.056 Uiso 1 1 calc R . .
C15 C 0.5108(3) 0.8731(3) 0.1130(3) 0.0363(8) Uani 1 1 d . . .
C16 C 0.6628(3) 1.0746(3) 0.4175(2) 0.0331(8) Uani 1 1 d . . .
H16 H 0.6075 1.0688 0.4628 0.040 Uiso 1 1 calc R . .
C17 C 0.6604(3) 1.1805(3) 0.3685(3) 0.0382(8) Uani 1 1 d . . .
C18 C 0.7421(3) 1.3166(3) 0.4502(3) 0.0379(8) Uani 1 1 d . . .
C19 C 0.7731(3) 1.4134(3) 0.4033(3) 0.0493(9) Uani 1 1 d . . .
H19 H 0.7391 1.3921 0.3212 0.059 Uiso 1 1 calc R . .
C20 C 0.8523(4) 1.5390(3) 0.4746(4) 0.0561(10) Uani 1 1 d . . .
H20 H 0.8734 1.6027 0.4418 0.067 Uiso 1 1 calc R . .
C21 C 0.9001(3) 1.5701(3) 0.5953(3) 0.0490(9) Uani 1 1 d . . .
C22 C 0.8685(3) 1.4777(3) 0.6445(3) 0.0492(9) Uani 1 1 d . . .
H22 H 0.9002 1.5003 0.7266 0.059 Uiso 1 1 calc R . .
C23 C 0.7896(3) 1.3512(3) 0.5723(3) 0.0439(9) Uani 1 1 d . . .
H23 H 0.7680 1.2882 0.6058 0.053 Uiso 1 1 calc R . .
C24 C 0.8014(3) 1.0928(3) 0.5023(3) 0.0414(8) Uani 1 1 d . . .
H24A H 0.8740 1.1573 0.4943 0.050 Uiso 1 1 calc R . .
H24B H 0.8128 1.1196 0.5841 0.050 Uiso 1 1 calc R . .
C25 C 0.8917(3) 0.9493(3) 0.5663(3) 0.0531(10) Uani 1 1 d . . .
H25A H 0.9823 1.0159 0.5966 0.080 Uiso 1 1 calc R . .
H25B H 0.8907 0.8671 0.5386 0.080 Uiso 1 1 calc R . .
H25C H 0.8607 0.9524 0.6284 0.080 Uiso 1 1 calc R . .
C26 C 0.6630(3) 0.8678(3) 0.4004(3) 0.0344(8) Uani 1 1 d . . .
C27 C 0.6632(4) 0.7531(3) 0.3189(3) 0.0403(8) Uani 1 1 d . . .
C28 C 0.5224(4) 0.5607(4) 0.1560(3) 0.0855(14) Uani 1 1 d . . .
H28A H 0.5675 0.5918 0.1087 0.128 Uiso 1 1 calc R . .
H28B H 0.4282 0.5056 0.1060 0.128 Uiso 1 1 calc R . .
H28C H 0.5629 0.5133 0.1944 0.128 Uiso 1 1 calc R . .
C29 C 0.5873(3) 0.8258(3) 0.4772(3) 0.0408(8) Uani 1 1 d . . .
H29A H 0.6067 0.9022 0.5390 0.049 Uiso 1 1 calc R . .
H29B H 0.4907 0.7847 0.4276 0.049 Uiso 1 1 calc R . .
C30 C 0.6214(3) 0.7357(4) 0.5349(3) 0.0476(9) Uani 1 1 d . . .
C31 C 0.6341(6) 0.6695(5) 0.7004(4) 0.1202(19) Uani 1 1 d . . .
H31A H 0.5857 0.5831 0.6444 0.180 Uiso 1 1 calc R . .
H31B H 0.6007 0.6760 0.7608 0.180 Uiso 1 1 calc R . .
H31C H 0.7289 0.6914 0.7364 0.180 Uiso 1 1 calc R . .
Cl1 Cl 0.90162(9) 0.98699(10) 0.07656(8) 0.0675(3) Uani 1 1 d . . .
Cl2 Cl 1.00625(11) 1.72843(9) 0.68815(10) 0.0835(4) Uani 1 1 d . . .
N1 N 0.4010(2) 0.8443(2) 0.1455(2) 0.0382(7) Uani 1 1 d . . .
N2 N 0.8023(2) 0.9683(2) 0.4681(2) 0.0372(7) Uani 1 1 d . . .
O1 O 0.3712(2) 0.8738(2) 0.31802(18) 0.0440(6) Uani 1 1 d . . .
O2 O 0.5912(2) 1.1551(2) 0.2645(2) 0.0599(7) Uani 1 1 d . . .
O3 O 0.7616(2) 0.7422(2) 0.31702(19) 0.0531(6) Uani 1 1 d . . .
O4 O 0.5351(2) 0.6680(2) 0.24476(19) 0.0505(6) Uani 1 1 d . . .
O5 O 0.6470(3) 0.6529(3) 0.4933(2) 0.0728(8) Uani 1 1 d . . .
O6 O 0.6143(3) 0.7579(2) 0.6392(2) 0.0760(8) 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 C6 1.375(4) . ?
C1 C2 1.380(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(4) . ?
C7 N1 1.457(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.223(3) . ?
C8 N1 1.359(4) . ?
C8 C9 1.543(4) . ?
C9 C10 1.509(4) . ?
C9 C16 1.540(4) . ?
C9 C26 1.593(4) . ?
C10 C11 1.373(4) . ?
C10 C15 1.395(4) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(4) . ?
C12 Cl1 1.742(3) . ?
C13 C14 1.387(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(4) . ?
C14 H14 0.9300 . ?
C15 N1 1.411(3) . ?
C16 C17 1.514(4) . ?
C16 C24 1.535(4) . ?
C16 H16 0.9800 . ?
C17 O2 1.214(3) . ?
C17 C18 1.487(4) . ?
C18 C23 1.382(4) . ?
C18 C19 1.387(4) . ?
C19 C20 1.363(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(4) . ?
C21 Cl2 1.734(3) . ?
C22 C23 1.373(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 N2 1.454(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N2 1.462(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 N2 1.463(3) . ?
C26 C27 1.530(4) . ?
C26 C29 1.547(4) . ?
C27 O3 1.197(3) . ?
C27 O4 1.343(4) . ?
C28 O4 1.443(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.501(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 O5 1.190(4) . ?
C30 O6 1.327(4) . ?
C31 O6 1.461(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.4(4) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 118.2(4) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 121.5(4) . . ?
N1 C7 C6 112.4(3) . . ?
N1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
O1 C8 N1 125.1(3) . . ?
O1 C8 C9 126.3(3) . . ?
N1 C8 C9 108.6(2) . . ?
C10 C9 C16 117.5(2) . . ?
C10 C9 C8 101.6(2) . . ?
C16 C9 C8 111.0(2) . . ?
C10 C9 C26 111.0(2) . . ?
C16 C9 C26 100.8(2) . . ?
C8 C9 C26 115.6(2) . . ?
C11 C10 C15 119.3(3) . . ?
C11 C10 C9 131.5(3) . . ?
C15 C10 C9 109.2(2) . . ?
C10 C11 C12 118.5(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 Cl1 119.2(3) . . ?
C11 C12 Cl1 119.3(3) . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 117.8(3) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C10 122.6(3) . . ?
C14 C15 N1 128.1(3) . . ?
C10 C15 N1 109.2(3) . . ?
C17 C16 C24 117.1(2) . . ?
C17 C16 C9 115.0(2) . . ?
C24 C16 C9 104.6(2) . . ?
C17 C16 H16 106.4 . . ?
C24 C16 H16 106.4 . . ?
C9 C16 H16 106.4 . . ?
O2 C17 C18 120.3(3) . . ?
O2 C17 C16 120.7(3) . . ?
C18 C17 C16 119.0(3) . . ?
C23 C18 C19 118.1(3) . . ?
C23 C18 C17 122.6(3) . . ?
C19 C18 C17 119.3(3) . . ?
C20 C19 C18 121.5(3) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 Cl2 119.0(3) . . ?
C20 C21 Cl2 120.0(3) . . ?
C21 C22 C23 119.7(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C18 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
N2 C24 C16 105.8(2) . . ?
N2 C24 H24A 110.6 . . ?
C16 C24 H24A 110.6 . . ?
N2 C24 H24B 110.6 . . ?
C16 C24 H24B 110.6 . . ?
H24A C24 H24B 108.7 . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 C27 109.0(2) . . ?
N2 C26 C29 114.5(2) . . ?
C27 C26 C29 111.3(2) . . ?
N2 C26 C9 99.6(2) . . ?
C27 C26 C9 109.7(2) . . ?
C29 C26 C9 112.1(2) . . ?
O3 C27 O4 124.5(3) . . ?
O3 C27 C26 125.9(3) . . ?
O4 C27 C26 109.5(3) . . ?
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 . . ?
C30 C29 C26 115.6(3) . . ?
C30 C29 H29A 108.4 . . ?
C26 C29 H29A 108.4 . . ?
C30 C29 H29B 108.4 . . ?
C26 C29 H29B 108.4 . . ?
H29A C29 H29B 107.4 . . ?
O5 C30 O6 123.7(3) . . ?
O5 C30 C29 126.1(3) . . ?
O6 C30 C29 110.2(3) . . ?
O6 C31 H31A 109.5 . . ?
O6 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O6 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C8 N1 C15 111.3(2) . . ?
C8 N1 C7 123.6(2) . . ?
C15 N1 C7 125.0(3) . . ?
C24 N2 C25 112.8(2) . . ?
C24 N2 C26 109.5(2) . . ?
C25 N2 C26 117.7(2) . . ?
C27 O4 C28 114.7(2) . . ?
C30 O6 C31 115.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.059
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2f
_audit_block_doi                 10.5517/cc13rk6m
_database_code_depnum_ccdc_archive 'CCDC 1035530'
_audit_update_record             
;
2014-11-24 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 Cl N2 O6'
_chemical_formula_sum            'C25 H25 Cl N2 O6'
_chemical_formula_weight         484.92

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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.5714(10)
_cell_length_b                   15.502(2)
_cell_length_c                   20.241(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2375.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      22.37

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.964
_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            35908
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.53
_reflns_number_total             5479
_reflns_number_gt                3678
_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)+(0.0536P)²+0.1462P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5465
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.0809(3) 0.16982(14) 0.28296(10) 0.0412(5) Uani 1 1 d . . .
C2 C 0.0302(3) 0.13574(15) 0.22251(12) 0.0583(7) Uani 1 1 d . . .
H2 H -0.0787 0.1088 0.2174 0.070 Uiso 1 1 calc R . .
C3 C 0.1454(4) 0.14283(16) 0.17024(11) 0.0594(7) Uani 1 1 d . . .
H3 H 0.1151 0.1203 0.1292 0.071 Uiso 1 1 calc R . .
C4 C 0.3047(3) 0.18305(15) 0.17874(11) 0.0530(6) Uani 1 1 d . . .
C5 C 0.3564(3) 0.21824(14) 0.23858(10) 0.0433(5) Uani 1 1 d . . .
H5 H 0.4650 0.2456 0.2432 0.052 Uiso 1 1 calc R . .
C6 C 0.2413(3) 0.21129(13) 0.29104(10) 0.0362(5) Uani 1 1 d . . .
C7 C 0.2563(2) 0.24186(13) 0.36227(9) 0.0342(5) Uani 1 1 d . . .
C8 C 0.0835(3) 0.20670(14) 0.39183(11) 0.0413(5) Uani 1 1 d . . .
C9 C 0.4279(3) 0.21182(13) 0.39822(10) 0.0371(5) Uani 1 1 d . . .
H9 H 0.4029 0.2070 0.4456 0.045 Uiso 1 1 calc R . .
C10 C 0.4907(3) 0.12504(14) 0.37334(10) 0.0406(5) Uani 1 1 d . . .
C11 C 0.3865(3) 0.04584(13) 0.38670(11) 0.0396(5) Uani 1 1 d . . .
C12 C 0.3989(3) -0.02246(15) 0.34224(11) 0.0488(6) Uani 1 1 d . . .
H12 H 0.4656 -0.0163 0.3040 0.059 Uiso 1 1 calc R . .
C13 C 0.3133(3) -0.09885(16) 0.35457(12) 0.0555(6) Uani 1 1 d . . .
H13 H 0.3207 -0.1432 0.3237 0.067 Uiso 1 1 calc R . .
C14 C 0.2172(3) -0.11159(15) 0.41118(13) 0.0562(6) Uani 1 1 d . . .
C15 C 0.1311(4) -0.19708(17) 0.42509(16) 0.0828(9) Uani 1 1 d . . .
H15A H 0.1547 -0.2361 0.3893 0.124 Uiso 1 1 calc R . .
H15B H 0.0058 -0.1892 0.4294 0.124 Uiso 1 1 calc R . .
H15C H 0.1777 -0.2205 0.4654 0.124 Uiso 1 1 calc R . .
C16 C 0.2038(4) -0.04342(16) 0.45529(13) 0.0585(7) Uani 1 1 d . . .
H16 H 0.1387 -0.0505 0.4939 0.070 Uiso 1 1 calc R . .
C17 C 0.2850(3) 0.03464(15) 0.44300(12) 0.0495(6) Uani 1 1 d . . .
H17 H 0.2716 0.0800 0.4727 0.059 Uiso 1 1 calc R . .
C18 C 0.5570(3) 0.28655(13) 0.38767(11) 0.0438(5) Uani 1 1 d . . .
H18A H 0.5950 0.3099 0.4298 0.053 Uiso 1 1 calc R . .
H18B H 0.6602 0.2671 0.3635 0.053 Uiso 1 1 calc R . .
C19 C 0.5438(3) 0.43614(14) 0.35484(11) 0.0512(6) Uani 1 1 d . . .
H19A H 0.4760 0.4774 0.3302 0.077 Uiso 1 1 calc R . .
H19B H 0.6615 0.4334 0.3373 0.077 Uiso 1 1 calc R . .
H19C H 0.5486 0.4534 0.4004 0.077 Uiso 1 1 calc R . .
C20 C 0.2741(3) 0.34337(13) 0.36636(9) 0.0361(5) Uani 1 1 d . . .
C21 C 0.1480(3) 0.37949(13) 0.31469(11) 0.0422(5) Uani 1 1 d . . .
C22 C 0.1096(4) 0.4329(2) 0.20816(13) 0.0799(9) Uani 1 1 d . . .
H22A H 0.0669 0.3802 0.1890 0.120 Uiso 1 1 calc R . .
H22B H 0.1734 0.4651 0.1754 0.120 Uiso 1 1 calc R . .
H22C H 0.0116 0.4665 0.2237 0.120 Uiso 1 1 calc R . .
C23 C 0.2243(3) 0.37718(13) 0.43530(10) 0.0448(5) Uani 1 1 d . . .
H23A H 0.1144 0.3502 0.4487 0.054 Uiso 1 1 calc R . .
H23B H 0.3148 0.3594 0.4664 0.054 Uiso 1 1 calc R . .
C24 C 0.2029(3) 0.47288(15) 0.44002(12) 0.0445(5) Uani 1 1 d . . .
C25 C 0.1890(5) 0.58853(16) 0.51532(14) 0.0785(9) Uani 1 1 d . . .
H25A H 0.2718 0.6227 0.4907 0.118 Uiso 1 1 calc R . .
H25B H 0.2034 0.5996 0.5617 0.118 Uiso 1 1 calc R . .
H25C H 0.0709 0.6033 0.5022 0.118 Uiso 1 1 calc R . .
Cl1 Cl 0.44885(14) 0.18977(6) 0.11192(3) 0.0985(3) Uani 1 1 d . . .
N1 N -0.0083(2) 0.16822(12) 0.34279(9) 0.0482(5) Uani 1 1 d . . .
H1 H -0.1107 0.1453 0.3481 0.058 Uiso 1 1 calc R . .
N2 N 0.4613(2) 0.35172(11) 0.34986(8) 0.0373(4) Uani 1 1 d . . .
O1 O 0.0364(2) 0.21162(11) 0.44902(7) 0.0547(4) Uani 1 1 d . . .
O2 O 0.62635(19) 0.11915(11) 0.34130(9) 0.0577(5) Uani 1 1 d . . .
O3 O -0.0090(2) 0.37141(11) 0.32074(9) 0.0622(5) Uani 1 1 d . . .
O4 O 0.2252(2) 0.41325(10) 0.26265(7) 0.0510(4) Uani 1 1 d . . .
O5 O 0.1744(3) 0.52138(10) 0.39581(9) 0.0699(5) Uani 1 1 d . . .
O6 O 0.2202(3) 0.49846(10) 0.50233(8) 0.0603(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 C6 1.384(3) . ?
C1 N1 1.387(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 Cl1 1.741(2) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.522(3) . ?
C7 C8 1.539(3) . ?
C7 C9 1.560(3) . ?
C7 C20 1.582(3) . ?
C8 O1 1.214(2) . ?
C8 N1 1.350(3) . ?
C9 C10 1.513(3) . ?
C9 C18 1.530(3) . ?
C9 H9 0.9800 . ?
C10 O2 1.218(2) . ?
C10 C11 1.484(3) . ?
C11 C17 1.385(3) . ?
C11 C12 1.393(3) . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 C16 1.387(3) . ?
C14 C15 1.503(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N2 1.460(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N2 1.454(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N2 1.462(3) . ?
C20 C21 1.523(3) . ?
C20 C23 1.538(3) . ?
C21 O3 1.202(3) . ?
C21 O4 1.314(3) . ?
C22 O4 1.441(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.495(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O5 1.189(3) . ?
C24 O6 1.329(3) . ?
C25 O6 1.440(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N1 H1 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
C6 C1 N1 109.40(18) . . ?
C6 C1 C2 121.6(2) . . ?
N1 C1 C2 129.0(2) . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 122.6(2) . . ?
C3 C4 Cl1 118.82(18) . . ?
C5 C4 Cl1 118.60(19) . . ?
C6 C5 C4 117.7(2) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C1 120.03(19) . . ?
C5 C6 C7 131.16(18) . . ?
C1 C6 C7 108.81(17) . . ?
C6 C7 C8 101.21(16) . . ?
C6 C7 C9 114.29(16) . . ?
C8 C7 C9 114.91(15) . . ?
C6 C7 C20 111.46(16) . . ?
C8 C7 C20 113.85(16) . . ?
C9 C7 C20 101.63(16) . . ?
O1 C8 N1 125.28(19) . . ?
O1 C8 C7 126.8(2) . . ?
N1 C8 C7 107.95(18) . . ?
C10 C9 C18 115.23(17) . . ?
C10 C9 C7 111.81(16) . . ?
C18 C9 C7 103.93(15) . . ?
C10 C9 H9 108.5 . . ?
C18 C9 H9 108.5 . . ?
C7 C9 H9 108.5 . . ?
O2 C10 C11 118.89(19) . . ?
O2 C10 C9 120.57(19) . . ?
C11 C10 C9 120.53(18) . . ?
C17 C11 C12 118.3(2) . . ?
C17 C11 C10 123.3(2) . . ?
C12 C11 C10 118.38(19) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C16 117.8(2) . . ?
C13 C14 C15 120.9(2) . . ?
C16 C14 C15 121.3(2) . . ?
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 . . ?
C17 C16 C14 121.3(2) . . ?
C17 C16 H16 119.4 . . ?
C14 C16 H16 119.4 . . ?
C16 C17 C11 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C11 C17 H17 119.8 . . ?
N2 C18 C9 106.27(16) . . ?
N2 C18 H18A 110.5 . . ?
C9 C18 H18A 110.5 . . ?
N2 C18 H18B 110.5 . . ?
C9 C18 H18B 110.5 . . ?
H18A C18 H18B 108.7 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 114.74(17) . . ?
N2 C20 C23 114.52(17) . . ?
C21 C20 C23 110.13(17) . . ?
N2 C20 C7 99.12(16) . . ?
C21 C20 C7 106.05(16) . . ?
C23 C20 C7 111.46(16) . . ?
O3 C21 O4 124.3(2) . . ?
O3 C21 C20 120.8(2) . . ?
O4 C21 C20 114.70(19) . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C20 115.00(18) . . ?
C24 C23 H23A 108.5 . . ?
C20 C23 H23A 108.5 . . ?
C24 C23 H23B 108.5 . . ?
C20 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
O5 C24 O6 122.9(2) . . ?
O5 C24 C23 126.8(2) . . ?
O6 C24 C23 110.24(19) . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8 N1 C1 112.56(17) . . ?
C8 N1 H1 123.7 . . ?
C1 N1 H1 123.7 . . ?
C19 N2 C18 111.92(16) . . ?
C19 N2 C20 118.72(18) . . ?
C18 N2 C20 107.46(16) . . ?
C21 O4 C22 115.3(2) . . ?
C24 O6 C25 116.51(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 O2 0.86 2.04 2.869(2) 162.8 1_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.038
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2k
_audit_block_doi                 10.5517/cc13rk7n
_database_code_depnum_ccdc_archive 'CCDC 1035531'
_audit_update_record             
;
2014-11-24 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H33 F N2 O6'
_chemical_formula_sum            'C33 H33 F N2 O6'
_chemical_formula_weight         572.61

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   12.0486(15)
_cell_length_b                   19.463(2)
_cell_length_c                   13.0530(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.160(2)
_cell_angle_gamma                90.00
_cell_volume                     2940.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6213
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_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            17333
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             9314
_reflns_number_gt                7107
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(15)
_refine_ls_number_reflns         9314
_refine_ls_number_parameters     763
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.1072
_refine_ls_wR_factor_ref         0.2921
_refine_ls_wR_factor_gt          0.2579
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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 0.4405(5) 0.0932(4) 0.1310(5) 0.0524(15) Uani 1 1 d . . .
H1 H 0.5100 0.0884 0.1838 0.063 Uiso 1 1 calc R . .
C2 C 0.4257(7) 0.0594(4) 0.0317(6) 0.073(2) Uani 1 1 d . . .
H2 H 0.4866 0.0354 0.0176 0.087 Uiso 1 1 calc R . .
C3 C 0.3193(8) 0.0629(4) -0.0437(5) 0.0660(19) Uani 1 1 d . . .
H3 H 0.3071 0.0394 -0.1079 0.079 Uiso 1 1 calc R . .
C4 C 0.2325(6) 0.1007(3) -0.0237(5) 0.0511(14) Uani 1 1 d . . .
H4 H 0.1613 0.1033 -0.0747 0.061 Uiso 1 1 calc R . .
C5 C 0.2499(5) 0.1360(3) 0.0739(4) 0.0462(13) Uani 1 1 d . . .
H5 H 0.1901 0.1618 0.0866 0.055 Uiso 1 1 calc R . .
C6 C 0.3553(4) 0.1325(3) 0.1508(4) 0.0390(11) Uani 1 1 d . . .
C7 C 0.3771(5) 0.1670(3) 0.2563(4) 0.0456(13) Uani 1 1 d . . .
H7A H 0.3433 0.1393 0.3017 0.055 Uiso 1 1 calc R . .
H7B H 0.4598 0.1686 0.2892 0.055 Uiso 1 1 calc R . .
C8 C 0.2291(4) 0.2519(3) 0.2723(4) 0.0305(10) Uani 1 1 d . . .
C9 C 0.2101(4) 0.3298(3) 0.2654(4) 0.0302(10) Uani 1 1 d . . .
C10 C 0.3218(4) 0.3544(3) 0.2452(4) 0.0328(10) Uani 1 1 d . . .
C11 C 0.3607(5) 0.4196(4) 0.2321(5) 0.0534(15) Uani 1 1 d . . .
H11 H 0.3170 0.4584 0.2360 0.064 Uiso 1 1 calc R . .
C12 C 0.4681(5) 0.4246(4) 0.2129(6) 0.0570(16) Uani 1 1 d . . .
C13 C 0.5354(6) 0.3690(5) 0.2072(5) 0.065(2) Uani 1 1 d . . .
H13 H 0.6076 0.3753 0.1958 0.078 Uiso 1 1 calc R . .
C14 C 0.4959(4) 0.3022(4) 0.2186(4) 0.0479(14) Uani 1 1 d . . .
H14 H 0.5397 0.2635 0.2143 0.057 Uiso 1 1 calc R . .
C15 C 0.3877(4) 0.2972(3) 0.2368(4) 0.0364(11) Uani 1 1 d . . .
C16 C 0.1845(4) 0.3575(3) 0.3658(4) 0.0319(10) Uani 1 1 d . . .
H16 H 0.1287 0.3259 0.3825 0.038 Uiso 1 1 calc R . .
C17 C 0.2877(4) 0.3605(3) 0.4646(4) 0.0399(12) Uani 1 1 d . . .
C18 C 0.2744(4) 0.3935(3) 0.5639(4) 0.0361(11) Uani 1 1 d . . .
C19 C 0.1666(5) 0.4018(3) 0.5852(5) 0.0446(12) Uani 1 1 d . . .
H19 H 0.0984 0.3889 0.5353 0.053 Uiso 1 1 calc R . .
C20 C 0.1652(7) 0.4299(4) 0.6827(5) 0.0612(17) Uani 1 1 d . . .
H20 H 0.0949 0.4351 0.6982 0.073 Uiso 1 1 calc R . .
C21 C 0.2624(9) 0.4497(4) 0.7550(6) 0.076(2) Uani 1 1 d . . .
H21 H 0.2575 0.4697 0.8183 0.091 Uiso 1 1 calc R . .
C22 C 0.3644(9) 0.4414(5) 0.7388(6) 0.078(2) Uani 1 1 d . . .
H22 H 0.4305 0.4546 0.7912 0.094 Uiso 1 1 calc R . .
C23 C 0.3749(6) 0.4125(4) 0.6417(5) 0.0595(16) Uani 1 1 d . . .
H23 H 0.4471 0.4063 0.6303 0.071 Uiso 1 1 calc R . .
C24 C 0.1193(5) 0.4265(3) 0.3305(4) 0.0383(11) Uani 1 1 d . . .
H24A H 0.0490 0.4284 0.3527 0.046 Uiso 1 1 calc R . .
H24B H 0.1677 0.4653 0.3609 0.046 Uiso 1 1 calc R . .
C25 C -0.0144(5) 0.4653(3) 0.1633(5) 0.0458(13) Uani 1 1 d . . .
H25A H -0.0349 0.4585 0.0875 0.069 Uiso 1 1 calc R . .
H25B H -0.0020 0.5133 0.1789 0.069 Uiso 1 1 calc R . .
H25C H -0.0757 0.4490 0.1907 0.069 Uiso 1 1 calc R . .
C26 C 0.1013(4) 0.3567(3) 0.1751(4) 0.0293(10) Uani 1 1 d . . .
C27 C 0.1272(5) 0.3601(3) 0.0670(4) 0.0388(12) Uani 1 1 d . . .
C28 C 0.1825(5) 0.2929(4) -0.0614(4) 0.0497(14) Uani 1 1 d . . .
H28A H 0.1352 0.3256 -0.1109 0.060 Uiso 1 1 calc R . .
H28B H 0.1641 0.2473 -0.0910 0.060 Uiso 1 1 calc R . .
C29 C 0.3083(6) 0.3078(6) -0.0499(6) 0.072(2) Uani 1 1 d . . .
H29A H 0.3255 0.3543 -0.0259 0.109 Uiso 1 1 calc R . .
H29B H 0.3238 0.3019 -0.1176 0.109 Uiso 1 1 calc R . .
H29C H 0.3555 0.2768 0.0012 0.109 Uiso 1 1 calc R . .
C30 C -0.0054(4) 0.3115(3) 0.1678(4) 0.0350(11) Uani 1 1 d . . .
H30A H 0.0185 0.2638 0.1702 0.042 Uiso 1 1 calc R . .
H30B H -0.0313 0.3200 0.2307 0.042 Uiso 1 1 calc R . .
C31 C -0.1076(4) 0.3211(4) 0.0706(4) 0.0461(13) Uani 1 1 d . . .
C32 C -0.3121(7) 0.3072(6) 0.0078(8) 0.088(3) Uani 1 1 d . . .
H32A H -0.3710 0.2844 0.0332 0.106 Uiso 1 1 calc R . .
H32B H -0.2968 0.2793 -0.0482 0.106 Uiso 1 1 calc R . .
C33 C -0.3540(9) 0.3761(8) -0.0350(9) 0.109(4) Uani 1 1 d . . .
H33A H -0.4039 0.3945 0.0041 0.164 Uiso 1 1 calc R . .
H33B H -0.3960 0.3720 -0.1090 0.164 Uiso 1 1 calc R . .
H33C H -0.2892 0.4062 -0.0280 0.164 Uiso 1 1 calc R . .
C34 C 0.6659(6) 0.4453(4) 0.5715(7) 0.0626(18) Uani 1 1 d . . .
H34 H 0.6016 0.4531 0.5139 0.075 Uiso 1 1 calc R . .
C35 C 0.6796(9) 0.4833(5) 0.6652(10) 0.108(4) Uani 1 1 d . . .
H35 H 0.6236 0.5147 0.6715 0.130 Uiso 1 1 calc R . .
C36 C 0.7789(8) 0.4730(5) 0.7489(7) 0.077(2) Uani 1 1 d . . .
H36 H 0.7927 0.5007 0.8092 0.093 Uiso 1 1 calc R . .
C37 C 0.8508(8) 0.4264(5) 0.7440(6) 0.074(2) Uani 1 1 d . . .
H37 H 0.9105 0.4164 0.8046 0.089 Uiso 1 1 calc R . .
C38 C 0.8432(7) 0.3894(4) 0.6498(5) 0.0616(18) Uani 1 1 d . . .
H38 H 0.9024 0.3600 0.6449 0.074 Uiso 1 1 calc R . .
C39 C 0.7440(5) 0.3978(3) 0.5630(4) 0.0416(12) Uani 1 1 d . . .
C40 C 0.7318(6) 0.3605(3) 0.4573(5) 0.0488(15) Uani 1 1 d . . .
H40A H 0.6509 0.3607 0.4170 0.059 Uiso 1 1 calc R . .
H40B H 0.7740 0.3862 0.4165 0.059 Uiso 1 1 calc R . .
C41 C 0.8755(4) 0.2724(3) 0.4502(4) 0.0292(10) Uani 1 1 d . . .
C42 C 0.8857(4) 0.1939(3) 0.4535(4) 0.0285(10) Uani 1 1 d . . .
C43 C 0.7733(4) 0.1722(3) 0.4712(4) 0.0350(10) Uani 1 1 d . . .
C44 C 0.7299(5) 0.1079(4) 0.4809(5) 0.0491(14) Uani 1 1 d . . .
H44 H 0.7700 0.0680 0.4744 0.059 Uiso 1 1 calc R . .
C45 C 0.6197(6) 0.1060(5) 0.5014(5) 0.063(2) Uani 1 1 d . . .
C46 C 0.5571(4) 0.1645(5) 0.5092(5) 0.062(2) Uani 1 1 d . . .
H46 H 0.4848 0.1605 0.5212 0.074 Uiso 1 1 calc R . .
C47 C 0.6012(5) 0.2286(4) 0.4993(5) 0.0539(16) Uani 1 1 d . . .
H47 H 0.5603 0.2682 0.5055 0.065 Uiso 1 1 calc R . .
C48 C 0.7084(4) 0.2325(3) 0.4798(4) 0.0352(11) Uani 1 1 d . . .
C49 C 0.9148(4) 0.1679(3) 0.3516(4) 0.0317(10) Uani 1 1 d . . .
H49 H 0.9721 0.2000 0.3385 0.038 Uiso 1 1 calc R . .
C50 C 0.8134(4) 0.1691(3) 0.2522(4) 0.0366(11) Uani 1 1 d . . .
C51 C 0.8266(4) 0.1349(3) 0.1526(4) 0.0357(11) Uani 1 1 d . . .
C52 C 0.9301(5) 0.1159(3) 0.1380(5) 0.0461(13) Uani 1 1 d . . .
H52 H 0.9980 0.1251 0.1911 0.055 Uiso 1 1 calc R . .
C53 C 0.9355(6) 0.0832(4) 0.0458(6) 0.0604(18) Uani 1 1 d . . .
H53 H 1.0062 0.0701 0.0362 0.072 Uiso 1 1 calc R . .
C54 C 0.8310(7) 0.0701(4) -0.0341(6) 0.0670(19) Uani 1 1 d . . .
H54 H 0.8330 0.0472 -0.0961 0.080 Uiso 1 1 calc R . .
C55 C 0.7343(6) 0.0892(4) -0.0221(6) 0.0612(17) Uani 1 1 d . . .
H55 H 0.6679 0.0812 -0.0774 0.073 Uiso 1 1 calc R . .
C56 C 0.7226(5) 0.1222(4) 0.0716(5) 0.0508(14) Uani 1 1 d . . .
H56 H 0.6509 0.1348 0.0792 0.061 Uiso 1 1 calc R . .
C57 C 0.9790(5) 0.0987(3) 0.3853(5) 0.0429(12) Uani 1 1 d . . .
H57A H 0.9338 0.0606 0.3474 0.051 Uiso 1 1 calc R . .
H57B H 1.0536 0.0990 0.3705 0.051 Uiso 1 1 calc R . .
C58 C 1.0881(6) 0.0480(4) 0.5537(6) 0.0591(17) Uani 1 1 d . . .
H58A H 1.0810 0.0049 0.5167 0.089 Uiso 1 1 calc R . .
H58B H 1.0854 0.0404 0.6256 0.089 Uiso 1 1 calc R . .
H58C H 1.1604 0.0691 0.5546 0.089 Uiso 1 1 calc R . .
C59 C 0.9906(4) 0.1626(3) 0.5421(4) 0.0332(10) Uani 1 1 d . . .
C60 C 0.9610(4) 0.1596(3) 0.6474(4) 0.0409(12) Uani 1 1 d . . .
C61 C 0.9146(5) 0.2249(5) 0.7832(5) 0.0540(15) Uani 1 1 d . . .
H61A H 0.9379 0.2690 0.8168 0.065 Uiso 1 1 calc R . .
H61B H 0.9561 0.1894 0.8308 0.065 Uiso 1 1 calc R . .
C62 C 0.7844(6) 0.2153(6) 0.7665(6) 0.071(2) Uani 1 1 d . . .
H62A H 0.7434 0.2529 0.7254 0.107 Uiso 1 1 calc R . .
H62B H 0.7684 0.2139 0.8345 0.107 Uiso 1 1 calc R . .
H62C H 0.7601 0.1730 0.7291 0.107 Uiso 1 1 calc R . .
C63 C 1.1047(4) 0.2049(3) 0.5551(4) 0.0394(11) Uani 1 1 d . . .
H63A H 1.1309 0.1985 0.4919 0.047 Uiso 1 1 calc R . .
H63B H 1.0880 0.2533 0.5602 0.047 Uiso 1 1 calc R . .
C64 C 1.2012(5) 0.1844(4) 0.6524(5) 0.0560(18) Uani 1 1 d . . .
C65 C 1.4012(8) 0.1594(13) 0.7152(11) 0.250(12) Uani 1 1 d DU . .
H65A H 1.4485 0.1269 0.6897 0.300 Uiso 1 1 calc R . .
H65B H 1.3739 0.1377 0.7706 0.300 Uiso 1 1 calc R . .
C66 C 1.4690(9) 0.2249(13) 0.7565(12) 0.252(12) Uani 1 1 d DU . .
H66A H 1.5073 0.2406 0.7055 0.378 Uiso 1 1 calc R . .
H66B H 1.5254 0.2154 0.8231 0.378 Uiso 1 1 calc R . .
H66C H 1.4169 0.2598 0.7670 0.378 Uiso 1 1 calc R . .
F1 F 0.5107(4) 0.4880(3) 0.1990(5) 0.0993(18) Uani 1 1 d . . .
F2 F 0.5750(5) 0.0444(3) 0.5147(5) 0.0963(17) Uani 1 1 d . . .
N1 N 0.3309(4) 0.2369(3) 0.2519(3) 0.0349(9) Uani 1 1 d . . .
N2 N 0.0928(4) 0.4268(2) 0.2140(3) 0.0340(9) Uani 1 1 d . . .
N3 N 0.7728(4) 0.2903(3) 0.4671(3) 0.0355(9) Uani 1 1 d . . .
N4 N 0.9928(4) 0.0934(3) 0.4990(4) 0.0412(10) Uani 1 1 d . . .
O1 O 0.1625(3) 0.2099(2) 0.2958(3) 0.0416(8) Uani 1 1 d . . .
O2 O 0.3755(4) 0.3316(4) 0.4654(4) 0.0694(15) Uani 1 1 d . . .
O3 O 0.1293(5) 0.4112(3) 0.0162(3) 0.0615(12) Uani 1 1 d . . .
O4 O 0.1546(3) 0.2969(2) 0.0378(3) 0.0415(8) Uani 1 1 d . . .
O5 O -0.1008(4) 0.3276(4) -0.0172(3) 0.0740(16) Uani 1 1 d . . .
O6 O -0.2066(3) 0.3144(3) 0.0955(4) 0.0652(13) Uani 1 1 d . . .
O7 O 0.9438(3) 0.3136(2) 0.4292(3) 0.0405(8) Uani 1 1 d . . .
O8 O 0.7262(4) 0.1984(3) 0.2515(3) 0.0671(14) Uani 1 1 d . . .
O9 O 0.9460(5) 0.1055(3) 0.6923(4) 0.0713(14) Uani 1 1 d . . .
O10 O 0.9458(3) 0.2217(2) 0.6830(3) 0.0432(9) Uani 1 1 d . . .
O11 O 1.1923(4) 0.1710(5) 0.7367(4) 0.102(3) Uani 1 1 d . . .
O12 O 1.3035(4) 0.1836(6) 0.6270(5) 0.125(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 C6 1.362(8) . ?
C1 C2 1.420(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.410(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.487(8) . ?
C7 N1 1.465(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.243(6) . ?
C8 N1 1.358(7) . ?
C8 C9 1.532(7) . ?
C9 C10 1.519(7) . ?
C9 C16 1.526(7) . ?
C9 C26 1.587(6) . ?
C10 C11 1.380(8) . ?
C10 C15 1.389(8) . ?
C11 C12 1.389(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(12) . ?
C12 F1 1.368(9) . ?
C13 C14 1.406(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(7) . ?
C14 H14 0.9300 . ?
C15 N1 1.400(7) . ?
C16 C17 1.523(7) . ?
C16 C24 1.560(6) . ?
C16 H16 0.9800 . ?
C17 O2 1.197(7) . ?
C17 C18 1.494(8) . ?
C18 C23 1.396(8) . ?
C18 C19 1.411(8) . ?
C19 C20 1.389(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.339(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.315(13) . ?
C21 H21 0.9300 . ?
C22 C23 1.424(11) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 N2 1.464(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N2 1.480(6) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 N2 1.470(6) . ?
C26 C27 1.530(7) . ?
C26 C30 1.538(6) . ?
C27 O3 1.200(7) . ?
C27 O4 1.354(7) . ?
C28 O4 1.427(7) . ?
C28 C29 1.509(9) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.513(7) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 O5 1.179(8) . ?
C31 O6 1.327(7) . ?
C32 O6 1.461(8) . ?
C32 C33 1.485(17) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C39 1.346(9) . ?
C34 C35 1.399(12) . ?
C34 H34 0.9300 . ?
C35 C36 1.391(14) . ?
C35 H35 0.9300 . ?
C36 C37 1.268(12) . ?
C36 H36 0.9300 . ?
C37 C38 1.405(10) . ?
C37 H37 0.9300 . ?
C38 C39 1.409(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.529(8) . ?
C40 N3 1.447(7) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 O7 1.234(6) . ?
C41 N3 1.361(6) . ?
C41 C42 1.533(6) . ?
C42 C43 1.497(7) . ?
C42 C49 1.551(7) . ?
C42 C59 1.578(6) . ?
C43 C44 1.376(9) . ?
C43 C48 1.431(8) . ?
C44 C45 1.426(9) . ?
C44 H44 0.9300 . ?
C45 F2 1.346(9) . ?
C45 C46 1.385(13) . ?
C46 C47 1.376(12) . ?
C46 H46 0.9300 . ?
C47 C48 1.386(8) . ?
C47 H47 0.9300 . ?
C48 N3 1.401(8) . ?
C49 C50 1.515(7) . ?
C49 C57 1.554(7) . ?
C49 H49 0.9800 . ?
C50 O8 1.194(6) . ?
C50 C51 1.508(7) . ?
C51 C52 1.364(8) . ?
C51 C56 1.418(8) . ?
C52 C53 1.379(8) . ?
C52 H52 0.9300 . ?
C53 C54 1.417(10) . ?
C53 H53 0.9300 . ?
C54 C55 1.274(10) . ?
C54 H54 0.9300 . ?
C55 C56 1.422(10) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C57 N4 1.451(8) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C58 N4 1.468(7) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 N4 1.463(7) . ?
C59 C60 1.513(7) . ?
C59 C63 1.571(7) . ?
C60 O9 1.243(8) . ?
C60 O10 1.327(7) . ?
C61 O10 1.459(7) . ?
C61 C62 1.533(8) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C63 C64 1.517(8) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C64 O11 1.164(8) . ?
C64 O12 1.363(7) . ?
C65 O12 1.476(16) . ?
C65 C66 1.529(2) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.6(6) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 118.9(6) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.5(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 118.5(5) . . ?
C1 C6 C7 118.7(5) . . ?
C5 C6 C7 122.7(5) . . ?
N1 C7 C6 114.5(4) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 126.0(4) . . ?
O1 C8 C9 124.7(4) . . ?
N1 C8 C9 109.2(4) . . ?
C10 C9 C16 116.0(4) . . ?
C10 C9 C8 101.4(4) . . ?
C16 C9 C8 111.2(4) . . ?
C10 C9 C26 110.9(4) . . ?
C16 C9 C26 101.5(3) . . ?
C8 C9 C26 116.7(4) . . ?
C11 C10 C15 120.4(5) . . ?
C11 C10 C9 131.2(5) . . ?
C15 C10 C9 108.3(4) . . ?
C10 C11 C12 116.8(6) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
C13 C12 F1 117.2(6) . . ?
C13 C12 C11 123.5(6) . . ?
F1 C12 C11 119.3(7) . . ?
C12 C13 C14 120.2(6) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 116.4(6) . . ?
C15 C14 H14 121.8 . . ?
C13 C14 H14 121.8 . . ?
C10 C15 C14 122.7(5) . . ?
C10 C15 N1 110.4(4) . . ?
C14 C15 N1 126.9(5) . . ?
C17 C16 C9 115.4(4) . . ?
C17 C16 C24 116.3(4) . . ?
C9 C16 C24 104.8(4) . . ?
C17 C16 H16 106.6 . . ?
C9 C16 H16 106.6 . . ?
C24 C16 H16 106.6 . . ?
O2 C17 C18 120.2(5) . . ?
O2 C17 C16 120.0(5) . . ?
C18 C17 C16 119.5(4) . . ?
C23 C18 C19 119.1(5) . . ?
C23 C18 C17 117.6(5) . . ?
C19 C18 C17 123.1(4) . . ?
C20 C19 C18 118.1(6) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 H19 120.9 . . ?
C21 C20 C19 121.9(7) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C20 121.6(7) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 120.7(7) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C18 C23 C22 118.5(7) . . ?
C18 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
N2 C24 C16 104.9(4) . . ?
N2 C24 H24A 110.8 . . ?
C16 C24 H24A 110.8 . . ?
N2 C24 H24B 110.8 . . ?
C16 C24 H24B 110.8 . . ?
H24A C24 H24B 108.8 . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 C27 109.2(4) . . ?
N2 C26 C30 114.5(4) . . ?
C27 C26 C30 110.4(4) . . ?
N2 C26 C9 99.9(4) . . ?
C27 C26 C9 111.1(4) . . ?
C30 C26 C9 111.2(4) . . ?
O3 C27 O4 123.6(5) . . ?
O3 C27 C26 126.0(5) . . ?
O4 C27 C26 110.4(4) . . ?
O4 C28 C29 112.5(5) . . ?
O4 C28 H28A 109.1 . . ?
C29 C28 H28A 109.1 . . ?
O4 C28 H28B 109.1 . . ?
C29 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C26 116.9(4) . . ?
C31 C30 H30A 108.1 . . ?
C26 C30 H30A 108.1 . . ?
C31 C30 H30B 108.1 . . ?
C26 C30 H30B 108.1 . . ?
H30A C30 H30B 107.3 . . ?
O5 C31 O6 124.0(5) . . ?
O5 C31 C30 124.6(5) . . ?
O6 C31 C30 111.1(5) . . ?
O6 C32 C33 109.9(9) . . ?
O6 C32 H32A 109.7 . . ?
C33 C32 H32A 109.7 . . ?
O6 C32 H32B 109.7 . . ?
C33 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C39 C34 C35 121.4(7) . . ?
C39 C34 H34 119.3 . . ?
C35 C34 H34 119.3 . . ?
C36 C35 C34 118.4(7) . . ?
C36 C35 H35 120.8 . . ?
C34 C35 H35 120.8 . . ?
C37 C36 C35 120.9(7) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C36 C37 C38 122.1(8) . . ?
C36 C37 H37 118.9 . . ?
C38 C37 H37 118.9 . . ?
C37 C38 C39 118.5(6) . . ?
C37 C38 H38 120.7 . . ?
C39 C38 H38 120.7 . . ?
C34 C39 C38 118.0(6) . . ?
C34 C39 C40 120.4(5) . . ?
C38 C39 C40 121.2(5) . . ?
N3 C40 C39 115.0(5) . . ?
N3 C40 H40A 108.5 . . ?
C39 C40 H40A 108.5 . . ?
N3 C40 H40B 108.5 . . ?
C39 C40 H40B 108.5 . . ?
H40A C40 H40B 107.5 . . ?
O7 C41 N3 124.3(4) . . ?
O7 C41 C42 126.9(4) . . ?
N3 C41 C42 108.7(4) . . ?
C43 C42 C41 102.5(4) . . ?
C43 C42 C49 118.0(4) . . ?
C41 C42 C49 109.7(4) . . ?
C43 C42 C59 110.7(4) . . ?
C41 C42 C59 116.5(4) . . ?
C49 C42 C59 100.2(3) . . ?
C44 C43 C48 120.6(5) . . ?
C44 C43 C42 130.8(5) . . ?
C48 C43 C42 108.5(4) . . ?
C43 C44 C45 116.0(6) . . ?
C43 C44 H44 122.0 . . ?
C45 C44 H44 122.0 . . ?
F2 C45 C46 118.5(6) . . ?
F2 C45 C44 118.3(8) . . ?
C46 C45 C44 123.2(6) . . ?
C47 C46 C45 120.4(5) . . ?
C47 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
C46 C47 C48 118.1(6) . . ?
C46 C47 H47 120.9 . . ?
C48 C47 H47 120.9 . . ?
C47 C48 N3 129.8(5) . . ?
C47 C48 C43 121.7(6) . . ?
N3 C48 C43 108.5(4) . . ?
C50 C49 C42 114.1(4) . . ?
C50 C49 C57 118.3(4) . . ?
C42 C49 C57 104.7(4) . . ?
C50 C49 H49 106.3 . . ?
C42 C49 H49 106.3 . . ?
C57 C49 H49 106.3 . . ?
O8 C50 C51 120.6(5) . . ?
O8 C50 C49 120.8(5) . . ?
C51 C50 C49 118.6(4) . . ?
C52 C51 C56 120.1(5) . . ?
C52 C51 C50 124.1(4) . . ?
C56 C51 C50 115.8(5) . . ?
C51 C52 C53 120.9(5) . . ?
C51 C52 H52 119.5 . . ?
C53 C52 H52 119.5 . . ?
C52 C53 C54 118.5(6) . . ?
C52 C53 H53 120.7 . . ?
C54 C53 H53 120.7 . . ?
C55 C54 C53 120.8(6) . . ?
C55 C54 H54 119.6 . . ?
C53 C54 H54 119.6 . . ?
C54 C55 C56 123.4(6) . . ?
C54 C55 H55 118.3 . . ?
C56 C55 H55 118.3 . . ?
C51 C56 C55 116.2(6) . . ?
C51 C56 H56 121.9 . . ?
C55 C56 H56 121.9 . . ?
N4 C57 C49 104.9(4) . . ?
N4 C57 H57A 110.8 . . ?
C49 C57 H57A 110.8 . . ?
N4 C57 H57B 110.8 . . ?
C49 C57 H57B 110.8 . . ?
H57A C57 H57B 108.8 . . ?
N4 C58 H58A 109.5 . . ?
N4 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
N4 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
N4 C59 C60 110.3(4) . . ?
N4 C59 C63 114.5(4) . . ?
C60 C59 C63 110.0(4) . . ?
N4 C59 C42 99.8(4) . . ?
C60 C59 C42 109.8(4) . . ?
C63 C59 C42 112.1(4) . . ?
O9 C60 O10 123.7(5) . . ?
O9 C60 C59 124.3(5) . . ?
O10 C60 C59 111.9(5) . . ?
O10 C61 C62 112.1(5) . . ?
O10 C61 H61A 109.2 . . ?
C62 C61 H61A 109.2 . . ?
O10 C61 H61B 109.2 . . ?
C62 C61 H61B 109.2 . . ?
H61A C61 H61B 107.9 . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C64 C63 C59 113.4(5) . . ?
C64 C63 H63A 108.9 . . ?
C59 C63 H63A 108.9 . . ?
C64 C63 H63B 108.9 . . ?
C59 C63 H63B 108.9 . . ?
H63A C63 H63B 107.7 . . ?
O11 C64 O12 123.7(5) . . ?
O11 C64 C63 126.9(5) . . ?
O12 C64 C63 109.5(5) . . ?
O12 C65 C66 103.9(14) . . ?
O12 C65 H65A 111.0 . . ?
C66 C65 H65A 111.0 . . ?
O12 C65 H65B 111.0 . . ?
C66 C65 H65B 111.0 . . ?
H65A C65 H65B 109.0 . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C65 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C8 N1 C15 110.5(4) . . ?
C8 N1 C7 123.1(5) . . ?
C15 N1 C7 126.1(4) . . ?
C24 N2 C26 109.8(4) . . ?
C24 N2 C25 112.2(4) . . ?
C26 N2 C25 116.9(4) . . ?
C41 N3 C48 111.8(4) . . ?
C41 N3 C40 122.0(5) . . ?
C48 N3 C40 125.6(4) . . ?
C57 N4 C59 108.6(4) . . ?
C57 N4 C58 113.0(5) . . ?
C59 N4 C58 117.6(5) . . ?
C27 O4 C28 116.2(5) . . ?
C31 O6 C32 117.6(6) . . ?
C60 O10 C61 116.6(5) . . ?
C64 O12 C65 113.2(7) . . ?

_diffrn_measured_fraction_theta_max 0.918
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.918
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.139

#====================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3b
_audit_block_doi                 10.5517/cc1492wd
_database_code_depnum_ccdc_archive 'CCDC 1051423'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H32 N2 O7 S'
_chemical_formula_sum            'C33 H32 N2 O7 S'
_chemical_formula_weight         600.67

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   18.950(7)
_cell_length_b                   13.964(6)
_cell_length_c                   11.122(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2943(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7536
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.959
_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            27278
_diffrn_reflns_av_R_equivalents  0.1319
_diffrn_reflns_av_sigmaI/netI    0.1324
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         27.81
_reflns_number_total             6853
_reflns_number_gt                3702
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0673P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.035(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6853
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1563
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_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 0.1666(2) 0.0576(2) 0.3943(4) 0.0561(10) Uani 1 1 d . . .
H1A H 0.2148 0.0352 0.4030 0.067 Uiso 1 1 calc R . .
H1B H 0.1376 0.0041 0.3688 0.067 Uiso 1 1 calc R . .
C2 C 0.0890(2) 0.2008(2) 0.4653(4) 0.0605(11) Uani 1 1 d . . .
H2A H 0.0391 0.1982 0.4840 0.073 Uiso 1 1 calc R . .
H2B H 0.1074 0.2619 0.4926 0.073 Uiso 1 1 calc R . .
C3 C 0.10067(16) 0.1895(2) 0.3290(4) 0.0470(9) Uani 1 1 d . . .
H3 H 0.0597 0.1573 0.2936 0.056 Uiso 1 1 calc R . .
C4 C 0.22434(16) 0.1948(2) 0.2836(3) 0.0390(8) Uani 1 1 d . . .
C5 C 0.27738(16) 0.1400(3) 0.2075(3) 0.0443(9) Uani 1 1 d . . .
C6 C 0.3780(2) 0.1608(3) 0.0874(5) 0.0801(14) Uani 1 1 d . . .
H6A H 0.4000 0.1052 0.1217 0.120 Uiso 1 1 calc R . .
H6B H 0.4134 0.2081 0.0702 0.120 Uiso 1 1 calc R . .
H6C H 0.3543 0.1434 0.0144 0.120 Uiso 1 1 calc R . .
C7 C 0.26027(16) 0.2402(2) 0.3927(3) 0.0412(8) Uani 1 1 d . . .
H7A H 0.2892 0.2931 0.3648 0.049 Uiso 1 1 calc R . .
H7B H 0.2240 0.2667 0.4444 0.049 Uiso 1 1 calc R . .
C8 C 0.30568(17) 0.1751(3) 0.4667(4) 0.0486(9) Uani 1 1 d . . .
C9 C 0.3534(3) 0.1483(4) 0.6570(4) 0.0860(15) Uani 1 1 d . . .
H9A H 0.3345 0.0847 0.6634 0.129 Uiso 1 1 calc R . .
H9B H 0.3547 0.1772 0.7353 0.129 Uiso 1 1 calc R . .
H9C H 0.4003 0.1453 0.6247 0.129 Uiso 1 1 calc R . .
C10 C 0.3742(2) 0.5637(3) 0.1046(4) 0.0656(11) Uani 1 1 d . . .
H10 H 0.3450 0.6074 0.1436 0.079 Uiso 1 1 calc R . .
C11 C 0.4463(3) 0.5756(3) 0.1091(5) 0.0831(15) Uani 1 1 d . . .
H11 H 0.4652 0.6274 0.1506 0.100 Uiso 1 1 calc R . .
C12 C 0.4901(2) 0.5123(3) 0.0537(5) 0.0868(16) Uani 1 1 d . . .
H12 H 0.5388 0.5205 0.0573 0.104 Uiso 1 1 calc R . .
C13 C 0.4621(2) 0.4372(4) -0.0069(5) 0.0817(14) Uani 1 1 d . . .
H13 H 0.4915 0.3931 -0.0446 0.098 Uiso 1 1 calc R . .
C14 C 0.3895(2) 0.4261(3) -0.0125(4) 0.0655(12) Uani 1 1 d . . .
H14 H 0.3709 0.3748 -0.0555 0.079 Uiso 1 1 calc R . .
C15 C 0.34470(17) 0.4882(2) 0.0432(4) 0.0475(9) Uani 1 1 d . . .
C16 C 0.26603(17) 0.4785(2) 0.0352(4) 0.0525(10) Uani 1 1 d . . .
H16A H 0.2445 0.5283 0.0837 0.063 Uiso 1 1 calc R . .
H16B H 0.2517 0.4890 -0.0476 0.063 Uiso 1 1 calc R . .
C17 C 0.22533(15) 0.3694(2) 0.1917(3) 0.0397(8) Uani 1 1 d . . .
C18 C 0.18691(15) 0.2717(2) 0.2013(3) 0.0372(8) Uani 1 1 d . . .
C19 C 0.18361(16) 0.2416(2) 0.0713(3) 0.0413(8) Uani 1 1 d . . .
C20 C 0.15744(19) 0.1601(3) 0.0173(4) 0.0532(10) Uani 1 1 d . . .
H20 H 0.1366 0.1122 0.0632 0.064 Uiso 1 1 calc R . .
C21 C 0.1626(2) 0.1509(3) -0.1053(4) 0.0661(12) Uani 1 1 d . . .
H21 H 0.1448 0.0966 -0.1428 0.079 Uiso 1 1 calc R . .
C22 C 0.1939(2) 0.2214(4) -0.1729(4) 0.0712(13) Uani 1 1 d . . .
H22 H 0.1973 0.2139 -0.2558 0.085 Uiso 1 1 calc R . .
C23 C 0.22065(19) 0.3033(3) -0.1196(4) 0.0605(11) Uani 1 1 d . . .
H23 H 0.2416 0.3512 -0.1653 0.073 Uiso 1 1 calc R . .
C24 C 0.21530(16) 0.3112(3) 0.0005(3) 0.0423(8) Uani 1 1 d . . .
C25 C 0.11345(16) 0.2842(2) 0.2634(3) 0.0431(9) Uani 1 1 d . . .
H25 H 0.1176 0.3351 0.3237 0.052 Uiso 1 1 calc R . .
C26 C 0.05607(16) 0.3117(3) 0.1766(4) 0.0518(10) Uani 1 1 d . . .
C27 C 0.06242(17) 0.4044(3) 0.1123(4) 0.0469(9) Uani 1 1 d . . .
C28 C 0.08247(19) 0.4883(3) 0.1682(4) 0.0594(11) Uani 1 1 d . . .
H28 H 0.0936 0.4873 0.2496 0.071 Uiso 1 1 calc R . .
C29 C 0.0864(2) 0.5730(3) 0.1066(4) 0.0626(11) Uani 1 1 d . . .
H29 H 0.0983 0.6294 0.1462 0.075 Uiso 1 1 calc R . .
C30 C 0.07257(17) 0.5735(3) -0.0150(4) 0.0529(10) Uani 1 1 d . . .
C31 C 0.0568(2) 0.6654(3) -0.1923(5) 0.0778(13) Uani 1 1 d . . .
H31A H 0.0880 0.6265 -0.2398 0.117 Uiso 1 1 calc R . .
H31B H 0.0595 0.7307 -0.2191 0.117 Uiso 1 1 calc R . .
H31C H 0.0093 0.6426 -0.2011 0.117 Uiso 1 1 calc R . .
C32 C 0.05388(18) 0.4897(3) -0.0729(4) 0.0618(11) Uani 1 1 d . . .
H32 H 0.0445 0.4898 -0.1550 0.074 Uiso 1 1 calc R . .
C33 C 0.04931(18) 0.4068(3) -0.0082(4) 0.0559(10) Uani 1 1 d . . .
H33 H 0.0369 0.3504 -0.0474 0.067 Uiso 1 1 calc R . .
N1 N 0.16357(13) 0.13251(17) 0.3070(3) 0.0409(7) Uani 1 1 d . . .
N2 N 0.23905(13) 0.38649(18) 0.0744(3) 0.0439(7) Uani 1 1 d . . .
O1 O 0.27367(13) 0.05752(17) 0.1802(3) 0.0615(7) Uani 1 1 d . . .
O2 O 0.32821(11) 0.19928(15) 0.1706(2) 0.0493(6) Uani 1 1 d . . .
O3 O 0.33681(15) 0.1073(2) 0.4289(3) 0.0756(9) Uani 1 1 d . . .
O4 O 0.30953(13) 0.20437(18) 0.5790(2) 0.0582(7) Uani 1 1 d . . .
O5 O 0.23727(12) 0.42379(15) 0.2729(2) 0.0512(6) Uani 1 1 d . . .
O6 O 0.00706(13) 0.25899(19) 0.1552(3) 0.0745(9) Uani 1 1 d . . .
O7 O 0.07695(13) 0.66009(19) -0.0703(3) 0.0684(8) Uani 1 1 d . . .
S1 S 0.13444(5) 0.10482(7) 0.53750(10) 0.0616(3) 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 1.428(4) . ?
C1 S1 1.829(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.540(6) . ?
C2 S1 1.784(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.454(4) . ?
C3 C25 1.530(5) . ?
C3 H3 0.9800 . ?
C4 N1 1.467(4) . ?
C4 C5 1.521(5) . ?
C4 C7 1.529(5) . ?
C4 C18 1.579(5) . ?
C5 O1 1.193(4) . ?
C5 O2 1.335(4) . ?
C6 O2 1.426(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.498(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O3 1.193(4) . ?
C8 O4 1.316(5) . ?
C9 O4 1.434(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.375(5) . ?
C10 C11 1.377(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.361(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.355(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.499(4) . ?
C16 N2 1.450(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O5 1.201(4) . ?
C17 N2 1.352(4) . ?
C17 C18 1.551(4) . ?
C18 C19 1.507(5) . ?
C18 C25 1.564(4) . ?
C19 C20 1.378(5) . ?
C19 C24 1.388(5) . ?
C20 C21 1.373(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.344(5) . ?
C23 H23 0.9300 . ?
C24 N2 1.408(4) . ?
C25 C26 1.504(5) . ?
C25 H25 0.9800 . ?
C26 O6 1.209(4) . ?
C26 C27 1.483(5) . ?
C27 C33 1.364(5) . ?
C27 C28 1.380(5) . ?
C28 C29 1.369(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.378(6) . ?
C29 H29 0.9300 . ?
C30 O7 1.359(5) . ?
C30 C32 1.382(5) . ?
C31 O7 1.412(5) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.366(5) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 S1 108.3(2) . . ?
N1 C1 H1A 110.0 . . ?
S1 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
S1 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C3 C2 S1 107.3(2) . . ?
C3 C2 H2A 110.3 . . ?
S1 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
S1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
N1 C3 C25 105.2(3) . . ?
N1 C3 C2 109.8(3) . . ?
C25 C3 C2 113.8(3) . . ?
N1 C3 H3 109.3 . . ?
C25 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
N1 C4 C5 108.6(2) . . ?
N1 C4 C7 117.0(3) . . ?
C5 C4 C7 110.9(3) . . ?
N1 C4 C18 98.8(2) . . ?
C5 C4 C18 108.4(3) . . ?
C7 C4 C18 112.3(3) . . ?
O1 C5 O2 124.3(3) . . ?
O1 C5 C4 126.1(3) . . ?
O2 C5 C4 109.6(3) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 116.2(3) . . ?
C8 C7 H7A 108.2 . . ?
C4 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C4 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
O3 C8 O4 123.6(4) . . ?
O3 C8 C7 124.9(4) . . ?
O4 C8 C7 111.5(3) . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 120.9(4) . . ?
C15 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 121.8(4) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C10 117.4(3) . . ?
C14 C15 C16 122.4(3) . . ?
C10 C15 C16 120.2(3) . . ?
N2 C16 C15 114.4(3) . . ?
N2 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
N2 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
O5 C17 N2 125.3(3) . . ?
O5 C17 C18 126.4(3) . . ?
N2 C17 C18 108.2(3) . . ?
C19 C18 C17 101.5(3) . . ?
C19 C18 C25 114.7(3) . . ?
C17 C18 C25 110.4(2) . . ?
C19 C18 C4 112.7(3) . . ?
C17 C18 C4 115.3(2) . . ?
C25 C18 C4 102.7(3) . . ?
C20 C19 C24 119.1(3) . . ?
C20 C19 C18 131.5(3) . . ?
C24 C19 C18 109.3(3) . . ?
C21 C20 C19 119.0(4) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 121.0(4) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 117.8(4) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
C23 C24 C19 122.6(4) . . ?
C23 C24 N2 128.1(4) . . ?
C19 C24 N2 109.3(3) . . ?
C26 C25 C3 114.4(3) . . ?
C26 C25 C18 112.8(3) . . ?
C3 C25 C18 104.8(2) . . ?
C26 C25 H25 108.2 . . ?
C3 C25 H25 108.2 . . ?
C18 C25 H25 108.2 . . ?
O6 C26 C27 119.9(3) . . ?
O6 C26 C25 121.7(3) . . ?
C27 C26 C25 118.3(3) . . ?
C33 C27 C28 118.2(4) . . ?
C33 C27 C26 118.7(4) . . ?
C28 C27 C26 123.1(4) . . ?
C29 C28 C27 121.6(4) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C28 C29 C30 119.0(4) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
O7 C30 C29 115.9(4) . . ?
O7 C30 C32 123.9(4) . . ?
C29 C30 C32 120.1(4) . . ?
O7 C31 H31A 109.5 . . ?
O7 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O7 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C30 119.3(4) . . ?
C33 C32 H32 120.4 . . ?
C30 C32 H32 120.4 . . ?
C27 C33 C32 121.8(4) . . ?
C27 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C1 N1 C3 108.6(3) . . ?
C1 N1 C4 121.6(3) . . ?
C3 N1 C4 110.4(2) . . ?
C17 N2 C24 111.7(3) . . ?
C17 N2 C16 121.0(3) . . ?
C24 N2 C16 126.8(3) . . ?
C5 O2 C6 116.3(3) . . ?
C8 O4 C9 115.9(3) . . ?
C30 O7 C31 117.7(3) . . ?
C2 S1 C1 92.29(18) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.81
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.171
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3c
_audit_block_doi                 10.5517/cc1492xf
_database_code_depnum_ccdc_archive 'CCDC 1051424'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H33 Cl N2 O7 S'
_chemical_formula_sum            'C30 H33 Cl N2 O7 S'
_chemical_formula_weight         601.09

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'
S S 0.1246 0.1234 '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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   10.504(2)
_cell_length_b                   16.482(3)
_cell_length_c                   16.712(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2893.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5722
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      21.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  0.928
_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            24036
_diffrn_reflns_av_R_equivalents  0.1097
_diffrn_reflns_av_sigmaI/netI    0.1204
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.66
_reflns_number_total             6633
_reflns_number_gt                3613
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0895P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6633
_refine_ls_number_parameters     374
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1519
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.011
_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 0.1649(6) 0.8533(4) 0.5826(3) 0.0871(19) Uani 1 1 d . . .
H1A H 0.2514 0.8676 0.5705 0.131 Uiso 1 1 calc R . .
H1B H 0.1090 0.8952 0.5637 0.131 Uiso 1 1 calc R . .
H1C H 0.1441 0.8030 0.5567 0.131 Uiso 1 1 calc R . .
C2 C 0.2395(5) 0.7980(3) 0.7025(3) 0.0480(11) Uani 1 1 d . . .
C3 C 0.2375(4) 0.8001(3) 0.7934(2) 0.0401(10) Uani 1 1 d . . .
C4 C 0.0830(6) 0.5187(3) 0.8038(5) 0.100(2) Uani 1 1 d U . .
H4A H -0.0035 0.5375 0.8019 0.150 Uiso 1 1 calc R . .
H4B H 0.0893 0.4740 0.8403 0.150 Uiso 1 1 calc R . .
H4C H 0.1087 0.5014 0.7513 0.150 Uiso 1 1 calc R . .
C5 C 0.1553(5) 0.6539(3) 0.7919(3) 0.0509(11) Uani 1 1 d U . .
C6 C 0.2504(4) 0.7127(2) 0.8238(3) 0.0441(10) Uani 1 1 d . . .
H6A H 0.3348 0.6932 0.8104 0.053 Uiso 1 1 calc R . .
H6B H 0.2437 0.7133 0.8817 0.053 Uiso 1 1 calc R . .
C7 C 0.0040(4) 0.8215(3) 0.8262(3) 0.0483(11) Uani 1 1 d . . .
H7A H -0.0110 0.7868 0.7803 0.058 Uiso 1 1 calc R . .
H7B H -0.0540 0.8671 0.8233 0.058 Uiso 1 1 calc R . .
C8 C 0.1061(4) 0.8162(3) 0.9695(3) 0.0556(13) Uani 1 1 d . . .
H8A H 0.0745 0.8460 1.0155 0.067 Uiso 1 1 calc R . .
H8B H 0.1695 0.7776 0.9877 0.067 Uiso 1 1 calc R . .
C9 C 0.1650(4) 0.8756(3) 0.9068(2) 0.0407(10) Uani 1 1 d . . .
H9 H 0.1301 0.9300 0.9157 0.049 Uiso 1 1 calc R . .
C10 C 0.3117(4) 0.8807(3) 0.9077(2) 0.0370(10) Uani 1 1 d . . .
H10 H 0.3452 0.8410 0.9459 0.044 Uiso 1 1 calc R . .
C11 C 0.3615(4) 0.9637(3) 0.9287(2) 0.0412(10) Uani 1 1 d . . .
C12 C 0.5040(4) 0.9755(3) 0.9352(2) 0.0418(10) Uani 1 1 d . . .
C13 C 0.5849(4) 0.9138(3) 0.9606(3) 0.0549(13) Uani 1 1 d . . .
H13 H 0.5514 0.8634 0.9741 0.066 Uiso 1 1 calc R . .
C14 C 0.7154(5) 0.9270(3) 0.9658(3) 0.0596(13) Uani 1 1 d . . .
H14 H 0.7691 0.8854 0.9823 0.072 Uiso 1 1 calc R . .
C15 C 0.7648(5) 1.0014(3) 0.9464(3) 0.0515(12) Uani 1 1 d . . .
C16 C 0.9528(5) 1.0824(4) 0.9473(4) 0.0801(18) Uani 1 1 d . . .
H16A H 0.9400 1.1025 0.8940 0.120 Uiso 1 1 calc R . .
H16B H 1.0424 1.0773 0.9575 0.120 Uiso 1 1 calc R . .
H16C H 0.9160 1.1194 0.9851 0.120 Uiso 1 1 calc R . .
C17 C 0.6858(5) 1.0619(3) 0.9204(3) 0.0566(13) Uani 1 1 d . . .
H17 H 0.7198 1.1118 0.9057 0.068 Uiso 1 1 calc R . .
C18 C 0.5564(4) 1.0495(3) 0.9157(3) 0.0512(12) Uani 1 1 d . . .
H18 H 0.5037 1.0917 0.8992 0.061 Uiso 1 1 calc R . .
C19 C 0.4830(4) 0.8115(3) 0.8189(3) 0.0433(10) Uani 1 1 d . . .
C20 C 0.3520(4) 0.8556(2) 0.8214(2) 0.0357(9) Uani 1 1 d . . .
C21 C 0.3743(4) 0.9242(3) 0.7646(2) 0.0376(10) Uani 1 1 d . . .
C22 C 0.2948(4) 0.9863(3) 0.7401(2) 0.0429(11) Uani 1 1 d . . .
H22 H 0.2138 0.9921 0.7618 0.051 Uiso 1 1 calc R . .
C23 C 0.3389(5) 1.0395(3) 0.6829(3) 0.0556(13) Uani 1 1 d . . .
C24 C 0.4622(5) 1.0325(4) 0.6515(3) 0.0738(16) Uani 1 1 d . . .
H24 H 0.4911 1.0697 0.6138 0.089 Uiso 1 1 calc R . .
C25 C 0.5402(5) 0.9709(4) 0.6764(3) 0.0733(16) Uani 1 1 d . . .
H25 H 0.6220 0.9659 0.6556 0.088 Uiso 1 1 calc R . .
C26 C 0.4972(4) 0.9166(3) 0.7320(3) 0.0458(11) Uani 1 1 d . . .
C27 C 0.6806(5) 0.8153(4) 0.7410(4) 0.0733(16) Uani 1 1 d . . .
H27A H 0.7216 0.7906 0.7870 0.088 Uiso 1 1 calc R . .
H27B H 0.7353 0.8584 0.7216 0.088 Uiso 1 1 calc R . .
C28 C 0.6623(6) 0.7492(4) 0.6728(4) 0.097(2) Uani 1 1 d . . .
H28A H 0.6129 0.7046 0.6946 0.116 Uiso 1 1 calc R . .
H28B H 0.6127 0.7732 0.6300 0.116 Uiso 1 1 calc R . .
C29 C 0.7790(6) 0.7162(4) 0.6386(5) 0.109(2) Uani 1 1 d . . .
H29A H 0.8343 0.6988 0.6818 0.131 Uiso 1 1 calc R . .
H29B H 0.7578 0.6687 0.6070 0.131 Uiso 1 1 calc R . .
C30 C 0.8480(7) 0.7732(5) 0.5885(5) 0.133(3) Uani 1 1 d . . .
H30A H 0.7916 0.7949 0.5486 0.199 Uiso 1 1 calc R . .
H30B H 0.9174 0.7457 0.5627 0.199 Uiso 1 1 calc R . .
H30C H 0.8805 0.8165 0.6209 0.199 Uiso 1 1 calc R . .
Cl1 Cl 0.23742(13) 1.11350(8) 0.64615(9) 0.0724(4) Uani 1 1 d . . .
N1 N 0.1332(3) 0.8497(2) 0.82588(19) 0.0369(8) Uani 1 1 d . . .
N2 N 0.5566(3) 0.8496(2) 0.7653(2) 0.0504(10) Uani 1 1 d . . .
O1 O 0.1504(3) 0.8443(2) 0.66793(16) 0.0552(8) Uani 1 1 d . . .
O2 O 0.3199(3) 0.7611(2) 0.6670(2) 0.0665(10) Uani 1 1 d . . .
O3 O 0.1649(3) 0.5838(2) 0.8303(2) 0.0686(10) Uani 1 1 d U . .
O4 O 0.0836(3) 0.6652(2) 0.7370(2) 0.0697(10) Uani 1 1 d . . .
O5 O 0.2922(3) 1.0215(2) 0.9367(2) 0.0593(9) Uani 1 1 d . . .
O6 O 0.5127(3) 0.75338(19) 0.85975(18) 0.0545(8) Uani 1 1 d . . .
O7 O 0.8953(3) 1.0071(2) 0.9549(3) 0.0769(12) Uani 1 1 d . . .
S1 S -0.02280(11) 0.76446(8) 0.91928(7) 0.0560(3) 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 O1 1.443(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O2 1.198(5) . ?
C2 O1 1.339(6) . ?
C2 C3 1.519(6) . ?
C3 N1 1.472(5) . ?
C3 C6 1.533(6) . ?
C3 C20 1.582(6) . ?
C4 O3 1.445(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 O4 1.201(6) . ?
C5 O3 1.327(6) . ?
C5 C6 1.491(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N1 1.434(5) . ?
C7 S1 1.839(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.562(6) . ?
C8 S1 1.808(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.457(5) . ?
C9 C10 1.542(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.506(6) . ?
C10 C20 1.558(6) . ?
C10 H10 0.9800 . ?
C11 O5 1.206(5) . ?
C11 C12 1.513(6) . ?
C12 C18 1.377(6) . ?
C12 C13 1.392(6) . ?
C13 C14 1.391(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(7) . ?
C14 H14 0.9300 . ?
C15 C17 1.369(7) . ?
C15 O7 1.381(6) . ?
C16 O7 1.386(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.376(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O6 1.217(5) . ?
C19 N2 1.339(5) . ?
C19 C20 1.556(6) . ?
C20 C21 1.495(6) . ?
C21 C22 1.383(6) . ?
C21 C26 1.407(6) . ?
C22 C23 1.377(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.403(7) . ?
C23 Cl1 1.732(5) . ?
C24 C25 1.370(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.366(7) . ?
C25 H25 0.9300 . ?
C26 N2 1.386(5) . ?
C27 N2 1.477(6) . ?
C27 C28 1.588(8) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.457(8) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.452(9) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 124.7(4) . . ?
O2 C2 C3 121.1(4) . . ?
O1 C2 C3 114.1(4) . . ?
N1 C3 C2 113.1(4) . . ?
N1 C3 C6 117.7(3) . . ?
C2 C3 C6 108.0(3) . . ?
N1 C3 C20 97.8(3) . . ?
C2 C3 C20 107.4(3) . . ?
C6 C3 C20 112.2(3) . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O4 C5 O3 123.5(5) . . ?
O4 C5 C6 126.3(4) . . ?
O3 C5 C6 110.0(4) . . ?
C5 C6 C3 115.7(4) . . ?
C5 C6 H6A 108.4 . . ?
C3 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C3 C6 H6B 108.4 . . ?
H6A C6 H6B 107.4 . . ?
N1 C7 S1 108.3(3) . . ?
N1 C7 H7A 110.0 . . ?
S1 C7 H7A 110.0 . . ?
N1 C7 H7B 110.0 . . ?
S1 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 S1 106.3(3) . . ?
C9 C8 H8A 110.5 . . ?
S1 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
S1 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
N1 C9 C10 104.7(3) . . ?
N1 C9 C8 110.4(3) . . ?
C10 C9 C8 115.1(4) . . ?
N1 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
C8 C9 H9 108.8 . . ?
C11 C10 C9 113.5(4) . . ?
C11 C10 C20 111.3(3) . . ?
C9 C10 C20 104.4(3) . . ?
C11 C10 H10 109.2 . . ?
C9 C10 H10 109.2 . . ?
C20 C10 H10 109.2 . . ?
O5 C11 C10 122.2(4) . . ?
O5 C11 C12 119.1(4) . . ?
C10 C11 C12 118.6(4) . . ?
C18 C12 C13 118.4(4) . . ?
C18 C12 C11 119.5(4) . . ?
C13 C12 C11 122.1(4) . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C17 C15 C14 119.9(5) . . ?
C17 C15 O7 125.8(4) . . ?
C14 C15 O7 114.4(4) . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 120.5(5) . . ?
C15 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C12 120.9(4) . . ?
C17 C18 H18 119.6 . . ?
C12 C18 H18 119.6 . . ?
O6 C19 N2 126.6(4) . . ?
O6 C19 C20 125.3(4) . . ?
N2 C19 C20 108.1(4) . . ?
C21 C20 C19 101.4(3) . . ?
C21 C20 C10 115.4(3) . . ?
C19 C20 C10 112.9(3) . . ?
C21 C20 C3 111.6(3) . . ?
C19 C20 C3 113.2(3) . . ?
C10 C20 C3 102.8(3) . . ?
C22 C21 C26 120.3(4) . . ?
C22 C21 C20 130.8(4) . . ?
C26 C21 C20 108.8(4) . . ?
C23 C22 C21 118.3(4) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C22 C23 C24 121.2(4) . . ?
C22 C23 Cl1 119.2(4) . . ?
C24 C23 Cl1 119.6(4) . . ?
C25 C24 C23 120.0(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 119.6(5) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 N2 130.2(4) . . ?
C25 C26 C21 120.6(4) . . ?
N2 C26 C21 109.2(4) . . ?
N2 C27 C28 110.7(4) . . ?
N2 C27 H27A 109.5 . . ?
C28 C27 H27A 109.5 . . ?
N2 C27 H27B 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
C29 C28 C27 115.8(5) . . ?
C29 C28 H28A 108.3 . . ?
C27 C28 H28A 108.3 . . ?
C29 C28 H28B 108.3 . . ?
C27 C28 H28B 108.3 . . ?
H28A C28 H28B 107.4 . . ?
C30 C29 C28 113.9(7) . . ?
C30 C29 H29A 108.8 . . ?
C28 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
C28 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C7 N1 C9 108.0(3) . . ?
C7 N1 C3 121.7(3) . . ?
C9 N1 C3 109.5(3) . . ?
C19 N2 C26 112.4(3) . . ?
C19 N2 C27 120.9(4) . . ?
C26 N2 C27 126.3(4) . . ?
C2 O1 C1 114.3(4) . . ?
C5 O3 C4 116.9(4) . . ?
C15 O7 C16 119.0(4) . . ?
C8 S1 C7 92.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.065
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4a
_audit_block_doi                 10.5517/cc1492yg
_database_code_depnum_ccdc_archive 'CCDC 1051425'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H35 F N2 O11'
_chemical_formula_sum            'C37 H35 F N2 O11'
_chemical_formula_weight         702.67

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           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                   11.7030(13)
_cell_length_b                   30.077(4)
_cell_length_c                   29.480(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.181(3)
_cell_angle_gamma                90.00
_cell_volume                     10361(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      22.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4416
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.975
_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            93050
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_sigmaI/netI    0.1126
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         25.50
_reflns_number_total             19213
_reflns_number_gt                9215
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0523P)²+1.5769P] 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         19213
_refine_ls_number_parameters     1404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.3613(3) -0.00013(11) 0.26796(11) 0.0633(10) Uani 1 1 d . . .
H1 H 0.2990 0.0099 0.2834 0.076 Uiso 1 1 calc R . .
C2 C 0.4482(4) -0.02249(14) 0.29121(13) 0.0833(12) Uani 1 1 d . . .
H2 H 0.4443 -0.0276 0.3222 0.100 Uiso 1 1 calc R . .
C3 C 0.5393(4) -0.03704(14) 0.26942(16) 0.0929(14) Uani 1 1 d . . .
H3 H 0.5983 -0.0519 0.2855 0.111 Uiso 1 1 calc R . .
C4 C 0.5455(3) -0.03007(14) 0.22333(15) 0.0937(13) Uani 1 1 d . . .
H4 H 0.6077 -0.0406 0.2082 0.112 Uiso 1 1 calc R . .
C5 C 0.4580(3) -0.00728(12) 0.19987(12) 0.0723(11) Uani 1 1 d . . .
H5 H 0.4623 -0.0021 0.1689 0.087 Uiso 1 1 calc R . .
C6 C 0.3653(3) 0.00774(10) 0.22182(10) 0.0502(8) Uani 1 1 d . . .
C7 C 0.2690(3) 0.03361(11) 0.19868(9) 0.0557(9) Uani 1 1 d . . .
H7A H 0.1974 0.0218 0.2085 0.067 Uiso 1 1 calc R . .
H7B H 0.2747 0.0642 0.2089 0.067 Uiso 1 1 calc R . .
C8 C 0.2723(2) 0.07143(11) 0.12429(9) 0.0367(7) Uani 1 1 d . . .
C9 C 0.2380(2) 0.05939(9) 0.07462(8) 0.0329(7) Uani 1 1 d . . .
C10 C 0.2319(2) 0.00946(9) 0.07644(10) 0.0363(7) Uani 1 1 d . . .
C11 C 0.2055(2) -0.02135(10) 0.04297(10) 0.0449(8) Uani 1 1 d . . .
H11 H 0.1995 -0.0133 0.0125 0.054 Uiso 1 1 calc R . .
C12 C 0.1882(3) -0.06426(11) 0.05643(13) 0.0564(9) Uani 1 1 d . . .
C13 C 0.1915(3) -0.07732(12) 0.10101(14) 0.0634(10) Uani 1 1 d . . .
H13 H 0.1763 -0.1067 0.1085 0.076 Uiso 1 1 calc R . .
C14 C 0.2174(2) -0.04653(12) 0.13473(12) 0.0545(9) Uani 1 1 d . . .
H14 H 0.2203 -0.0546 0.1652 0.065 Uiso 1 1 calc R . .
C15 C 0.2391(2) -0.00319(10) 0.12180(10) 0.0384(7) Uani 1 1 d . . .
C16 C 0.1152(2) 0.07857(9) 0.06270(8) 0.0359(7) Uani 1 1 d . . .
H16 H 0.1100 0.1085 0.0755 0.043 Uiso 1 1 calc R . .
C17 C 0.0197(2) 0.04993(10) 0.08024(10) 0.0391(7) Uani 1 1 d . . .
C18 C -0.0089(2) 0.05277(10) 0.12850(9) 0.0372(7) Uani 1 1 d . . .
C19 C 0.0130(2) 0.08957(11) 0.15547(10) 0.0488(8) Uani 1 1 d . . .
H19 H 0.0515 0.1137 0.1438 0.059 Uiso 1 1 calc R . .
C20 C -0.0215(3) 0.09135(12) 0.19966(11) 0.0567(9) Uani 1 1 d . . .
H20 H -0.0067 0.1165 0.2174 0.068 Uiso 1 1 calc R . .
C21 C -0.0773(3) 0.05580(13) 0.21690(11) 0.0578(9) Uani 1 1 d . . .
C22 C -0.0988(4) 0.09168(15) 0.28792(13) 0.1172(17) Uani 1 1 d . . .
H22A H -0.0184 0.0972 0.2934 0.176 Uiso 1 1 calc R . .
H22B H -0.1330 0.0867 0.3163 0.176 Uiso 1 1 calc R . .
H22C H -0.1341 0.1170 0.2730 0.176 Uiso 1 1 calc R . .
C23 C -0.0985(3) 0.01821(12) 0.19068(11) 0.0583(9) Uani 1 1 d . . .
H23 H -0.1356 -0.0061 0.2027 0.070 Uiso 1 1 calc R . .
C24 C -0.0648(2) 0.01698(10) 0.14721(10) 0.0449(8) Uani 1 1 d . . .
H24 H -0.0794 -0.0083 0.1297 0.054 Uiso 1 1 calc R . .
C25 C 0.1086(2) 0.08182(10) 0.01150(9) 0.0435(8) Uani 1 1 d . . .
H25A H 0.0674 0.0566 -0.0018 0.052 Uiso 1 1 calc R . .
H25B H 0.0698 0.1089 0.0016 0.052 Uiso 1 1 calc R . .
C26 C 0.3118(2) 0.08040(9) 0.03721(9) 0.0346(7) Uani 1 1 d . . .
C27 C 0.3515(3) 0.12771(10) 0.05119(9) 0.0421(8) Uani 1 1 d . . .
C28 C 0.2867(3) 0.19993(11) 0.06640(12) 0.0750(11) Uani 1 1 d . . .
H28A H 0.3136 0.1981 0.0977 0.112 Uiso 1 1 calc R . .
H28B H 0.2177 0.2172 0.0639 0.112 Uiso 1 1 calc R . .
H28C H 0.3441 0.2138 0.0492 0.112 Uiso 1 1 calc R . .
C29 C 0.4164(2) 0.05264(10) 0.02629(9) 0.0412(7) Uani 1 1 d . . .
H29A H 0.3900 0.0240 0.0148 0.049 Uiso 1 1 calc R . .
H29B H 0.4549 0.0673 0.0021 0.049 Uiso 1 1 calc R . .
C30 C 0.5013(2) 0.04500(9) 0.06503(11) 0.0390(7) Uani 1 1 d . . .
C31 C 0.6951(2) 0.02839(12) 0.08422(10) 0.0618(10) Uani 1 1 d . . .
H31A H 0.7065 0.0535 0.1041 0.093 Uiso 1 1 calc R . .
H31B H 0.7648 0.0220 0.0699 0.093 Uiso 1 1 calc R . .
H31C H 0.6732 0.0030 0.1015 0.093 Uiso 1 1 calc R . .
C32 C 0.2446(2) 0.09427(9) -0.04571(9) 0.0367(7) Uani 1 1 d . . .
C33 C 0.3644(3) 0.10400(15) -0.05807(12) 0.0609(10) Uani 1 1 d . A .
C34 C 0.5223(4) 0.0895(3) -0.0966(2) 0.099(3) Uani 0.677(8) 1 d P A 1
H34A H 0.5105 0.1116 -0.1199 0.148 Uiso 0.677(8) 1 calc PR A 1
H34B H 0.5640 0.0650 -0.1083 0.148 Uiso 0.677(8) 1 calc PR A 1
H34C H 0.5651 0.1022 -0.0711 0.148 Uiso 0.677(8) 1 calc PR A 1
C34' C 0.5406(8) 0.1336(4) -0.0589(6) 0.106(7) Uani 0.323(8) 1 d P A 2
H34D H 0.5765 0.1087 -0.0436 0.159 Uiso 0.323(8) 1 calc PR A 2
H34E H 0.5818 0.1603 -0.0506 0.159 Uiso 0.323(8) 1 calc PR A 2
H34F H 0.5411 0.1293 -0.0911 0.159 Uiso 0.323(8) 1 calc PR A 2
C35 C 0.1586(2) 0.09958(10) -0.07730(9) 0.0463(8) Uani 1 1 d . . .
H35 H 0.0851 0.0917 -0.0698 0.056 Uiso 1 1 calc R . .
C36 C 0.1738(3) 0.11687(10) -0.12223(10) 0.0468(8) Uani 1 1 d . . .
C37 C 0.0692(3) 0.14030(14) -0.18923(10) 0.0915(13) Uani 1 1 d . . .
H37A H 0.0983 0.1700 -0.1855 0.137 Uiso 1 1 calc R . .
H37B H -0.0083 0.1414 -0.2017 0.137 Uiso 1 1 calc R . .
H37C H 0.1156 0.1242 -0.2095 0.137 Uiso 1 1 calc R . .
C38 C 0.8211(4) 0.69826(13) 0.29573(12) 0.0876(13) Uani 1 1 d . . .
H38 H 0.7625 0.6887 0.3134 0.105 Uiso 1 1 calc R . .
C39 C 0.9208(6) 0.71549(18) 0.31605(16) 0.126(2) Uani 1 1 d . . .
H39 H 0.9299 0.7164 0.3476 0.152 Uiso 1 1 calc R . .
C40 C 1.0056(5) 0.7311(2) 0.2909(2) 0.140(2) Uani 1 1 d . . .
H40 H 1.0708 0.7437 0.3050 0.168 Uiso 1 1 calc R . .
C41 C 0.9946(4) 0.72820(17) 0.24507(18) 0.1203(18) Uani 1 1 d . . .
H41 H 1.0529 0.7382 0.2275 0.144 Uiso 1 1 calc R . .
C42 C 0.8964(3) 0.71025(13) 0.22465(12) 0.0806(12) Uani 1 1 d . . .
H42 H 0.8894 0.7083 0.1931 0.097 Uiso 1 1 calc R . .
C43 C 0.8093(3) 0.69531(10) 0.24938(10) 0.0506(8) Uani 1 1 d . . .
C44 C 0.7020(2) 0.67565(11) 0.22842(9) 0.0510(8) Uani 1 1 d . . .
H44A H 0.6864 0.6483 0.2444 0.061 Uiso 1 1 calc R . .
H44B H 0.6395 0.6960 0.2334 0.061 Uiso 1 1 calc R . .
C45 C 0.7156(2) 0.62402(11) 0.16354(9) 0.0330(7) Uani 1 1 d . . .
C46 C 0.6819(2) 0.62549(9) 0.11222(8) 0.0289(6) Uani 1 1 d . . .
C47 C 0.6736(2) 0.67478(9) 0.10361(9) 0.0301(7) Uani 1 1 d . . .
C48 C 0.6517(2) 0.69839(10) 0.06392(10) 0.0393(7) Uani 1 1 d . . .
H48 H 0.6481 0.6844 0.0357 0.047 Uiso 1 1 calc R . .
C49 C 0.6355(2) 0.74336(11) 0.06796(11) 0.0478(8) Uani 1 1 d . . .
C50 C 0.6367(2) 0.76545(11) 0.10871(13) 0.0548(9) Uani 1 1 d . . .
H50 H 0.6235 0.7959 0.1097 0.066 Uiso 1 1 calc R . .
C51 C 0.6580(2) 0.74134(11) 0.14820(11) 0.0498(8) Uani 1 1 d . . .
H51 H 0.6593 0.7553 0.1764 0.060 Uiso 1 1 calc R . .
C52 C 0.6772(2) 0.69650(10) 0.14508(9) 0.0347(7) Uani 1 1 d . . .
C53 C 0.5603(2) 0.60362(9) 0.10396(8) 0.0324(7) Uani 1 1 d . . .
H53 H 0.5584 0.5755 0.1207 0.039 Uiso 1 1 calc R . .
C54 C 0.4633(2) 0.63355(10) 0.11854(9) 0.0353(7) Uani 1 1 d . . .
C55 C 0.4375(2) 0.63620(9) 0.16683(9) 0.0336(7) Uani 1 1 d . . .
C56 C 0.4630(2) 0.60259(10) 0.19789(10) 0.0475(8) Uani 1 1 d . . .
H56 H 0.4970 0.5766 0.1881 0.057 Uiso 1 1 calc R . .
C57 C 0.4390(3) 0.60691(11) 0.24308(11) 0.0559(9) Uani 1 1 d . . .
H57 H 0.4555 0.5838 0.2634 0.067 Uiso 1 1 calc R . .
C58 C 0.3906(3) 0.64563(12) 0.25774(10) 0.0531(9) Uani 1 1 d . . .
C59 C 0.4047(4) 0.62270(17) 0.33505(12) 0.1174(17) Uani 1 1 d . . .
H59A H 0.3630 0.5955 0.3300 0.176 Uiso 1 1 calc R . .
H59B H 0.3906 0.6340 0.3647 0.176 Uiso 1 1 calc R . .
H59C H 0.4850 0.6172 0.3331 0.176 Uiso 1 1 calc R . .
C60 C 0.3629(3) 0.67914(11) 0.22704(11) 0.0546(9) Uani 1 1 d . . .
H60 H 0.3285 0.7050 0.2369 0.066 Uiso 1 1 calc R . .
C61 C 0.3857(2) 0.67444(10) 0.18225(10) 0.0441(8) Uani 1 1 d . . .
H61 H 0.3662 0.6972 0.1619 0.053 Uiso 1 1 calc R . .
C62 C 0.5533(2) 0.59392(10) 0.05355(8) 0.0402(7) Uani 1 1 d . . .
H62A H 0.5108 0.5667 0.0471 0.048 Uiso 1 1 calc R . .
H62B H 0.5160 0.6181 0.0368 0.048 Uiso 1 1 calc R . .
C63 C 0.7558(2) 0.59770(9) 0.07986(8) 0.0311(7) Uani 1 1 d . . .
C64 C 0.7856(3) 0.55284(10) 0.10310(9) 0.0392(7) Uani 1 1 d . . .
C65 C 0.9264(3) 0.51264(11) 0.14500(11) 0.0719(11) Uani 1 1 d . . .
H65A H 0.8893 0.5139 0.1732 0.108 Uiso 1 1 calc R . .
H65B H 1.0079 0.5120 0.1510 0.108 Uiso 1 1 calc R . .
H65C H 0.9027 0.4863 0.1287 0.108 Uiso 1 1 calc R . .
C66 C 0.8610(2) 0.62232(9) 0.06349(9) 0.0377(7) Uani 1 1 d . . .
H66A H 0.9015 0.6023 0.0442 0.045 Uiso 1 1 calc R . .
H66B H 0.8343 0.6471 0.0448 0.045 Uiso 1 1 calc R . .
C67 C 0.9444(2) 0.63971(9) 0.09925(10) 0.0384(7) Uani 1 1 d . . .
C68 C 1.1383(2) 0.65963(12) 0.11397(11) 0.0663(10) Uani 1 1 d . . .
H68A H 1.1049 0.6767 0.1374 0.099 Uiso 1 1 calc R . .
H68B H 1.1871 0.6784 0.0972 0.099 Uiso 1 1 calc R . .
H68C H 1.1826 0.6357 0.1275 0.099 Uiso 1 1 calc R . .
C69 C 0.6936(2) 0.57065(9) 0.00036(9) 0.0348(7) Uani 1 1 d . . .
C70 C 0.8126(2) 0.55339(11) -0.00538(10) 0.0400(7) Uani 1 1 d . . .
C71 C 0.9806(3) 0.56269(13) -0.04504(12) 0.0877(13) Uani 1 1 d . . .
H71A H 1.0292 0.5675 -0.0182 0.132 Uiso 1 1 calc R . .
H71B H 1.0083 0.5798 -0.0697 0.132 Uiso 1 1 calc R . .
H71C H 0.9809 0.5317 -0.0528 0.132 Uiso 1 1 calc R . .
C72 C 0.6127(3) 0.56728(10) -0.03362(9) 0.0497(8) Uani 1 1 d . . .
H72 H 0.5416 0.5797 -0.0290 0.060 Uiso 1 1 calc R . .
C73 C 0.6272(3) 0.54587(12) -0.07677(11) 0.0609(10) Uani 1 1 d . . .
C74 C 0.7262(3) 0.49253(13) -0.11839(11) 0.0919(13) Uani 1 1 d . . .
H74A H 0.6552 0.4804 -0.1307 0.138 Uiso 1 1 calc R . .
H74B H 0.7802 0.4689 -0.1127 0.138 Uiso 1 1 calc R . .
H74C H 0.7559 0.5131 -0.1397 0.138 Uiso 1 1 calc R . .
C75 C 0.0220(3) 0.86756(13) 0.32653(11) 0.0735(11) Uani 1 1 d . . .
H75 H 0.0046 0.8436 0.3449 0.088 Uiso 1 1 calc R . .
C76 C -0.0632(3) 0.89804(15) 0.31332(12) 0.0833(12) Uani 1 1 d . . .
H76 H -0.1366 0.8947 0.3234 0.100 Uiso 1 1 calc R . .
C77 C -0.0392(4) 0.93247(14) 0.28579(13) 0.0805(12) Uani 1 1 d . . .
H77 H -0.0958 0.9531 0.2774 0.097 Uiso 1 1 calc R . .
C78 C 0.0670(4) 0.93687(13) 0.27057(13) 0.0842(12) Uani 1 1 d . . .
H78 H 0.0824 0.9598 0.2507 0.101 Uiso 1 1 calc R . .
C79 C 0.1531(3) 0.90735(13) 0.28435(11) 0.0704(10) Uani 1 1 d . . .
H79 H 0.2264 0.9111 0.2743 0.085 Uiso 1 1 calc R . .
C80 C 0.1305(3) 0.87251(11) 0.31275(10) 0.0525(8) Uani 1 1 d . . .
C81 C 0.2252(3) 0.84066(12) 0.32807(9) 0.0586(9) Uani 1 1 d . . .
H81A H 0.2167 0.8134 0.3106 0.070 Uiso 1 1 calc R . .
H81B H 0.2984 0.8537 0.3216 0.070 Uiso 1 1 calc R . .
C82 C 0.2148(2) 0.78760(11) 0.39213(9) 0.0376(7) Uani 1 1 d . . .
C83 C 0.2389(2) 0.78890(9) 0.44395(8) 0.0324(7) Uani 1 1 d . . .
C84 C 0.2445(2) 0.83808(9) 0.45311(9) 0.0334(7) Uani 1 1 d . . .
C85 C 0.2609(2) 0.86132(10) 0.49311(10) 0.0412(7) Uani 1 1 d . . .
H85 H 0.2628 0.8471 0.5211 0.049 Uiso 1 1 calc R . .
C86 C 0.2745(2) 0.90666(11) 0.48983(11) 0.0491(8) Uani 1 1 d . . .
C87 C 0.2775(2) 0.92882(11) 0.44963(12) 0.0550(9) Uani 1 1 d . . .
H87 H 0.2903 0.9593 0.4492 0.066 Uiso 1 1 calc R . .
C88 C 0.2613(2) 0.90538(11) 0.40974(11) 0.0510(8) Uani 1 1 d . . .
H88 H 0.2626 0.9198 0.3818 0.061 Uiso 1 1 calc R . .
C89 C 0.2433(2) 0.86044(10) 0.41188(10) 0.0378(7) Uani 1 1 d . . .
C90 C 0.3593(2) 0.76676(9) 0.45414(8) 0.0316(7) Uani 1 1 d . . .
H90 H 0.3619 0.7385 0.4377 0.038 Uiso 1 1 calc R . .
C91 C 0.4565(2) 0.79621(10) 0.43990(9) 0.0347(7) Uani 1 1 d . . .
C92 C 0.4885(2) 0.79555(10) 0.39189(9) 0.0348(7) Uani 1 1 d . . .
C93 C 0.5358(2) 0.83385(10) 0.37490(9) 0.0445(8) Uani 1 1 d . . .
H93 H 0.5427 0.8590 0.3932 0.053 Uiso 1 1 calc R . .
C94 C 0.5730(3) 0.83545(11) 0.33112(10) 0.0541(9) Uani 1 1 d . . .
H94 H 0.6043 0.8615 0.3201 0.065 Uiso 1 1 calc R . .
C95 C 0.5634(3) 0.79833(12) 0.30429(10) 0.0548(9) Uani 1 1 d . . .
C96 C 0.6563(5) 0.83401(18) 0.24426(14) 0.163(3) Uani 1 1 d . . .
H96A H 0.7253 0.8390 0.2627 0.244 Uiso 1 1 calc R . .
H96B H 0.6078 0.8597 0.2455 0.244 Uiso 1 1 calc R . .
H96C H 0.6750 0.8288 0.2134 0.244 Uiso 1 1 calc R . .
C97 C 0.5149(3) 0.76032(11) 0.32025(11) 0.0582(9) Uani 1 1 d . . .
H97 H 0.5079 0.7354 0.3017 0.070 Uiso 1 1 calc R . .
C98 C 0.4765(2) 0.75885(10) 0.36353(10) 0.0460(8) Uani 1 1 d . . .
H98 H 0.4424 0.7331 0.3738 0.055 Uiso 1 1 calc R . .
C99 C 0.3603(2) 0.75732(10) 0.50450(8) 0.0374(7) Uani 1 1 d . . .
H99A H 0.4033 0.7305 0.5120 0.045 Uiso 1 1 calc R . .
H99B H 0.3942 0.7819 0.5218 0.045 Uiso 1 1 calc R . .
C100 C 0.1598(2) 0.76055(9) 0.47422(8) 0.0351(7) Uani 1 1 d . . .
C101 C 0.1219(3) 0.71708(11) 0.45058(9) 0.0454(8) Uani 1 1 d . . .
C102 C 0.1826(3) 0.64633(12) 0.42785(13) 0.0901(13) Uani 1 1 d . . .
H02A H 0.1152 0.6335 0.4397 0.135 Uiso 1 1 calc R . .
H02B H 0.2460 0.6264 0.4331 0.135 Uiso 1 1 calc R . .
H02C H 0.1698 0.6513 0.3958 0.135 Uiso 1 1 calc R . .
C103 C 0.0529(2) 0.78543(10) 0.48844(9) 0.0424(8) Uani 1 1 d . . .
H03D H 0.0105 0.7660 0.5077 0.051 Uiso 1 1 calc R . .
H03E H 0.0774 0.8110 0.5066 0.051 Uiso 1 1 calc R . .
C104 C -0.0260(2) 0.80112(10) 0.45019(11) 0.0444(8) Uani 1 1 d . . .
C105 C -0.2171(2) 0.81996(12) 0.43064(11) 0.0658(10) Uani 1 1 d . . .
H05A H -0.1982 0.8493 0.4206 0.099 Uiso 1 1 calc R . .
H05B H -0.2904 0.8206 0.4438 0.099 Uiso 1 1 calc R . .
H05C H -0.2201 0.8000 0.4052 0.099 Uiso 1 1 calc R . .
C106 C 0.2135(2) 0.73238(9) 0.55403(9) 0.0338(7) Uani 1 1 d . . .
C107 C 0.0931(2) 0.71578(11) 0.55800(10) 0.0402(7) Uani 1 1 d . . .
C108 C -0.0813(3) 0.72883(13) 0.59171(13) 0.0829(12) Uani 1 1 d . . .
H08A H -0.1213 0.7243 0.5628 0.124 Uiso 1 1 calc R . .
H08B H -0.1189 0.7517 0.6080 0.124 Uiso 1 1 calc R . .
H08C H -0.0812 0.7017 0.6088 0.124 Uiso 1 1 calc R . .
C109 C 0.2912(2) 0.72615(9) 0.58891(9) 0.0425(8) Uani 1 1 d . . .
H09A H 0.3650 0.7370 0.5865 0.051 Uiso 1 1 calc R . .
C110 C 0.2636(3) 0.70325(11) 0.62989(10) 0.0491(8) Uani 1 1 d . . .
C111 C 0.3317(4) 0.68355(17) 0.70375(13) 0.137(2) Uani 1 1 d . . .
H11A H 0.2599 0.6929 0.7148 0.205 Uiso 1 1 calc R . .
H11B H 0.3924 0.6908 0.7257 0.205 Uiso 1 1 calc R . .
H11C H 0.3303 0.6520 0.6988 0.205 Uiso 1 1 calc R . .
F1 F 0.16447(17) -0.09519(6) 0.02359(7) 0.0874(6) Uani 1 1 d . . .
F2 F 0.61807(15) 0.76720(6) 0.02905(6) 0.0736(6) Uani 1 1 d . . .
F3 F 0.28816(15) 0.93002(6) 0.52938(6) 0.0722(6) Uani 1 1 d . . .
N1 N 0.26439(18) 0.03345(8) 0.14949(7) 0.0398(6) Uani 1 1 d . . .
N2 N 0.22694(17) 0.08203(7) -0.00195(7) 0.0365(6) Uani 1 1 d . . .
N3 N 0.70124(18) 0.66585(8) 0.18011(7) 0.0362(6) Uani 1 1 d . . .
N4 N 0.67231(17) 0.58919(7) 0.04138(7) 0.0350(6) Uani 1 1 d . . .
N5 N 0.22581(18) 0.82993(9) 0.37624(7) 0.0398(6) Uani 1 1 d . . .
N6 N 0.23914(17) 0.75177(7) 0.51412(7) 0.0342(6) Uani 1 1 d . . .
O1 O 0.29170(16) 0.10847(7) 0.13934(6) 0.0486(5) Uani 1 1 d . . .
O2 O -0.03292(16) 0.02432(7) 0.05491(7) 0.0522(6) Uani 1 1 d . . .
O3 O -0.1149(2) 0.05350(9) 0.25979(8) 0.0887(8) Uani 1 1 d . . .
O4 O 0.44863(18) 0.13695(7) 0.06219(7) 0.0586(6) Uani 1 1 d . . .
O5 O 0.26395(17) 0.15589(7) 0.04900(7) 0.0513(5) Uani 1 1 d . . .
O6 O 0.48107(16) 0.04320(8) 0.10414(7) 0.0593(6) Uani 1 1 d . . .
O7 O 0.60558(16) 0.03840(7) 0.04988(6) 0.0523(6) Uani 1 1 d . . .
O8 O 0.4124(2) 0.13795(9) -0.04451(8) 0.0745(7) Uani 1 1 d . . .
O9 O 0.40969(19) 0.07365(9) -0.08212(8) 0.0703(7) Uani 1 1 d . . .
O10 O 0.25964(19) 0.13029(8) -0.13776(7) 0.0691(7) Uani 1 1 d . . .
O11 O 0.07223(18) 0.11834(8) -0.14581(7) 0.0707(7) Uani 1 1 d . . .
O12 O 0.73995(16) 0.59131(7) 0.18577(6) 0.0480(5) Uani 1 1 d . . .
O13 O 0.41049(15) 0.65657(7) 0.09031(6) 0.0476(5) Uani 1 1 d . . .
O14 O 0.3681(2) 0.65438(9) 0.30162(8) 0.0833(8) Uani 1 1 d . . .
O15 O 0.71758(18) 0.52360(7) 0.10740(7) 0.0525(6) Uani 1 1 d . . .
O16 O 0.89542(16) 0.55136(6) 0.11804(6) 0.0478(5) Uani 1 1 d . . .
O17 O 0.92273(16) 0.65158(8) 0.13635(7) 0.0602(6) Uani 1 1 d . . .
O18 O 1.04867(16) 0.64164(7) 0.08370(6) 0.0542(6) Uani 1 1 d . . .
O19 O 0.85509(17) 0.52385(7) 0.01692(7) 0.0533(6) Uani 1 1 d . . .
O20 O 0.86467(16) 0.57649(7) -0.03669(7) 0.0517(5) Uani 1 1 d . . .
O21 O 0.5714(3) 0.55552(11) -0.11116(9) 0.1247(12) Uani 1 1 d . . .
O22 O 0.7073(2) 0.51527(7) -0.07659(7) 0.0661(6) Uani 1 1 d . . .
O23 O 0.19972(16) 0.75426(7) 0.36940(6) 0.0520(6) Uani 1 1 d . . .
O24 O 0.50654(15) 0.82062(7) 0.46743(6) 0.0479(5) Uani 1 1 d . . .
O25 O 0.5982(2) 0.79628(9) 0.26091(7) 0.0835(8) Uani 1 1 d . . .
O26 O 0.02688(19) 0.71059(8) 0.43499(7) 0.0683(7) Uani 1 1 d . . .
O27 O 0.20786(18) 0.68804(7) 0.45031(7) 0.0529(6) Uani 1 1 d . . .
O28 O -0.00128(17) 0.81012(9) 0.41301(8) 0.0833(8) Uani 1 1 d . . .
O29 O -0.13122(15) 0.80500(7) 0.46419(7) 0.0542(6) Uani 1 1 d . . .
O30 O 0.05448(17) 0.68446(7) 0.53783(7) 0.0581(6) Uani 1 1 d . . .
O31 O 0.03539(16) 0.74213(7) 0.58493(6) 0.0504(5) Uani 1 1 d . . .
O32 O 0.1769(2) 0.68377(8) 0.63723(7) 0.0642(6) Uani 1 1 d . . .
O33 O 0.3505(2) 0.70599(9) 0.66141(8) 0.0944(9) 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 1.371(5) . ?
C1 C6 1.384(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.502(4) . ?
C7 N1 1.448(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.216(3) . ?
C8 N1 1.369(3) . ?
C8 C9 1.540(4) . ?
C9 C10 1.505(4) . ?
C9 C16 1.570(3) . ?
C9 C26 1.571(3) . ?
C10 C11 1.376(4) . ?
C10 C15 1.388(4) . ?
C11 C12 1.369(4) . ?
C11 H11 0.9300 . ?
C12 F1 1.360(4) . ?
C12 C13 1.370(4) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 N1 1.393(3) . ?
C16 C25 1.510(3) . ?
C16 C17 1.524(4) . ?
C16 H16 0.9800 . ?
C17 O2 1.216(3) . ?
C17 C18 1.482(4) . ?
C18 C19 1.378(4) . ?
C18 C24 1.389(4) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(4) . ?
C20 H20 0.9300 . ?
C21 O3 1.363(3) . ?
C21 C23 1.384(4) . ?
C22 O3 1.423(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.362(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.461(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 N2 1.481(3) . ?
C26 C29 1.530(3) . ?
C26 C27 1.546(4) . ?
C27 O4 1.197(3) . ?
C27 O5 1.329(3) . ?
C28 O5 1.440(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.490(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 O6 1.191(3) . ?
C30 O7 1.337(3) . ?
C31 O7 1.447(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C35 1.342(4) . ?
C32 N2 1.368(3) . ?
C32 C33 1.497(4) . ?
C33 O8 1.222(4) . ?
C33 O9 1.288(4) . ?
C34 O9 1.487(5) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C34' O8 1.587(10) . ?
C34' H34D 0.9600 . ?
C34' H34E 0.9600 . ?
C34' H34F 0.9600 . ?
C35 C36 1.443(4) . ?
C35 H35 0.9300 . ?
C36 O10 1.197(3) . ?
C36 O11 1.344(3) . ?
C37 O11 1.439(4) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C43 1.369(4) . ?
C38 C39 1.382(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.355(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.352(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.377(5) . ?
C41 H41 0.9300 . ?
C42 C43 1.362(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.491(4) . ?
C44 N3 1.454(3) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 O12 1.207(3) . ?
C45 N3 1.364(3) . ?
C45 C46 1.543(3) . ?
C46 C47 1.506(4) . ?
C46 C63 1.564(3) . ?
C46 C53 1.574(3) . ?
C47 C48 1.380(3) . ?
C47 C52 1.385(3) . ?
C48 C49 1.372(4) . ?
C48 H48 0.9300 . ?
C49 F2 1.359(3) . ?
C49 C50 1.372(4) . ?
C50 C51 1.382(4) . ?
C50 H50 0.9300 . ?
C51 C52 1.371(4) . ?
C51 H51 0.9300 . ?
C52 N3 1.401(3) . ?
C53 C62 1.512(3) . ?
C53 C54 1.529(3) . ?
C53 H53 0.9800 . ?
C54 O13 1.223(3) . ?
C54 C55 1.474(4) . ?
C55 C56 1.385(4) . ?
C55 C61 1.388(4) . ?
C56 C57 1.383(4) . ?
C56 H56 0.9300 . ?
C57 C58 1.375(4) . ?
C57 H57 0.9300 . ?
C58 O14 1.360(3) . ?
C58 C60 1.381(4) . ?
C59 O14 1.420(4) . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C60 C61 1.369(4) . ?
C60 H60 0.9300 . ?
C61 H61 0.9300 . ?
C62 N4 1.465(3) . ?
C62 H62A 0.9700 . ?
C62 H62B 0.9700 . ?
C63 N4 1.478(3) . ?
C63 C66 1.537(3) . ?
C63 C64 1.545(4) . ?
C64 O15 1.198(3) . ?
C64 O16 1.336(3) . ?
C65 O16 1.445(3) . ?
C65 H65A 0.9600 . ?
C65 H65B 0.9600 . ?
C65 H65C 0.9600 . ?
C66 C67 1.491(4) . ?
C66 H66A 0.9700 . ?
C66 H66B 0.9700 . ?
C67 O17 1.191(3) . ?
C67 O18 1.329(3) . ?
C68 O18 1.444(3) . ?
C68 H68A 0.9600 . ?
C68 H68B 0.9600 . ?
C68 H68C 0.9600 . ?
C69 C72 1.344(4) . ?
C69 N4 1.367(3) . ?
C69 C70 1.504(4) . ?
C70 O19 1.197(3) . ?
C70 O20 1.330(3) . ?
C71 O20 1.453(3) . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
C72 C73 1.444(4) . ?
C72 H72 0.9300 . ?
C73 O21 1.211(4) . ?
C73 O22 1.313(4) . ?
C74 O22 1.437(3) . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 0.9600 . ?
C75 C80 1.363(4) . ?
C75 C76 1.394(5) . ?
C75 H75 0.9300 . ?
C76 C77 1.355(5) . ?
C76 H76 0.9300 . ?
C77 C78 1.351(5) . ?
C77 H77 0.9300 . ?
C78 C79 1.387(5) . ?
C78 H78 0.9300 . ?
C79 C80 1.376(4) . ?
C79 H79 0.9300 . ?
C80 C81 1.515(4) . ?
C81 N5 1.456(3) . ?
C81 H81A 0.9700 . ?
C81 H81B 0.9700 . ?
C82 O23 1.214(3) . ?
C82 N5 1.365(4) . ?
C82 C83 1.539(4) . ?
C83 C84 1.504(4) . ?
C83 C90 1.572(3) . ?
C83 C100 1.572(3) . ?
C84 C85 1.375(4) . ?
C84 C89 1.389(4) . ?
C85 C86 1.377(4) . ?
C85 H85 0.9300 . ?
C86 C87 1.362(4) . ?
C86 F3 1.363(3) . ?
C87 C88 1.375(4) . ?
C87 H87 0.9300 . ?
C88 C89 1.370(4) . ?
C88 H88 0.9300 . ?
C89 N5 1.401(3) . ?
C90 C99 1.511(3) . ?
C90 C91 1.519(3) . ?
C90 H90 0.9800 . ?
C91 O24 1.220(3) . ?
C91 C92 1.484(4) . ?
C92 C93 1.384(4) . ?
C92 C98 1.387(4) . ?
C93 C94 1.386(4) . ?
C93 H93 0.9300 . ?
C94 C95 1.369(4) . ?
C94 H94 0.9300 . ?
C95 O25 1.365(3) . ?
C95 C97 1.371(4) . ?
C96 O25 1.424(4) . ?
C96 H96A 0.9600 . ?
C96 H96B 0.9600 . ?
C96 H96C 0.9600 . ?
C97 C98 1.376(4) . ?
C97 H97 0.9300 . ?
C98 H98 0.9300 . ?
C99 N6 1.471(3) . ?
C99 H99A 0.9700 . ?
C99 H99B 0.9700 . ?
C100 N6 1.481(3) . ?
C100 C101 1.536(4) . ?
C100 C103 1.536(3) . ?
C101 O26 1.195(3) . ?
C101 O27 1.333(3) . ?
C102 O27 1.441(4) . ?
C102 H02A 0.9600 . ?
C102 H02B 0.9600 . ?
C102 H02C 0.9600 . ?
C103 C104 1.494(4) . ?
C103 H03D 0.9700 . ?
C103 H03E 0.9700 . ?
C104 O28 1.180(3) . ?
C104 O29 1.325(3) . ?
C105 O29 1.443(3) . ?
C105 H05A 0.9600 . ?
C105 H05B 0.9600 . ?
C105 H05C 0.9600 . ?
C106 C109 1.347(4) . ?
C106 N6 1.361(3) . ?
C106 C107 1.506(4) . ?
C107 O30 1.190(3) . ?
C107 O31 1.332(3) . ?
C108 O31 1.448(3) . ?
C108 H08A 0.9600 . ?
C108 H08B 0.9600 . ?
C108 H08C 0.9600 . ?
C109 C110 1.443(4) . ?
C109 H09A 0.9300 . ?
C110 O32 1.202(3) . ?
C110 O33 1.341(3) . ?
C111 O33 1.447(4) . ?
C111 H11A 0.9600 . ?
C111 H11B 0.9600 . ?
C111 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.7(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 123.4(3) . . ?
C1 C6 C7 118.0(3) . . ?
N1 C7 C6 116.0(2) . . ?
N1 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
O1 C8 N1 125.7(3) . . ?
O1 C8 C9 126.6(3) . . ?
N1 C8 C9 107.3(3) . . ?
C10 C9 C8 102.2(2) . . ?
C10 C9 C16 109.3(2) . . ?
C8 C9 C16 108.3(2) . . ?
C10 C9 C26 117.1(2) . . ?
C8 C9 C26 116.6(2) . . ?
C16 C9 C26 103.12(19) . . ?
C11 C10 C15 120.4(3) . . ?
C11 C10 C9 131.0(3) . . ?
C15 C10 C9 107.9(2) . . ?
C12 C11 C10 117.3(3) . . ?
C12 C11 H11 121.4 . . ?
C10 C11 H11 121.4 . . ?
F1 C12 C11 117.8(3) . . ?
F1 C12 C13 118.7(3) . . ?
C11 C12 C13 123.5(3) . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 118.0(3) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C14 C15 C10 121.4(3) . . ?
C14 C15 N1 128.3(3) . . ?
C10 C15 N1 110.3(3) . . ?
C25 C16 C17 112.2(2) . . ?
C25 C16 C9 104.0(2) . . ?
C17 C16 C9 113.3(2) . . ?
C25 C16 H16 109.0 . . ?
C17 C16 H16 109.0 . . ?
C9 C16 H16 109.0 . . ?
O2 C17 C18 119.5(3) . . ?
O2 C17 C16 120.4(2) . . ?
C18 C17 C16 120.2(3) . . ?
C19 C18 C24 118.0(3) . . ?
C19 C18 C17 123.7(3) . . ?
C24 C18 C17 118.2(3) . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
O3 C21 C20 124.8(3) . . ?
O3 C21 C23 114.8(3) . . ?
C20 C21 C23 120.4(3) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 119.7(3) . . ?
C24 C23 H23 120.2 . . ?
C21 C23 H23 120.2 . . ?
C23 C24 C18 121.3(3) . . ?
C23 C24 H24 119.3 . . ?
C18 C24 H24 119.3 . . ?
N2 C25 C16 106.0(2) . . ?
N2 C25 H25A 110.5 . . ?
C16 C25 H25A 110.5 . . ?
N2 C25 H25B 110.5 . . ?
C16 C25 H25B 110.5 . . ?
H25A C25 H25B 108.7 . . ?
N2 C26 C29 111.3(2) . . ?
N2 C26 C27 110.9(2) . . ?
C29 C26 C27 109.0(2) . . ?
N2 C26 C9 100.92(19) . . ?
C29 C26 C9 113.9(2) . . ?
C27 C26 C9 110.6(2) . . ?
O4 C27 O5 125.7(3) . . ?
O4 C27 C26 123.5(3) . . ?
O5 C27 C26 110.8(2) . . ?
O5 C28 H28A 109.5 . . ?
O5 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O5 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C26 115.5(2) . . ?
C30 C29 H29A 108.4 . . ?
C26 C29 H29A 108.4 . . ?
C30 C29 H29B 108.4 . . ?
C26 C29 H29B 108.4 . . ?
H29A C29 H29B 107.5 . . ?
O6 C30 O7 123.4(3) . . ?
O6 C30 C29 126.1(3) . . ?
O7 C30 C29 110.4(3) . . ?
O7 C31 H31A 109.5 . . ?
O7 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O7 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C35 C32 N2 122.7(2) . . ?
C35 C32 C33 119.0(3) . . ?
N2 C32 C33 118.3(2) . . ?
O8 C33 O9 125.2(3) . . ?
O8 C33 C32 120.2(4) . . ?
O9 C33 C32 114.5(4) . . ?
O9 C34 H34A 109.5 . . ?
O9 C34 H34B 109.5 . . ?
O9 C34 H34C 109.5 . . ?
O8 C34' H34D 109.5 . . ?
O8 C34' H34E 109.5 . . ?
H34D C34' H34E 109.5 . . ?
O8 C34' H34F 109.5 . . ?
H34D C34' H34F 109.5 . . ?
H34E C34' H34F 109.5 . . ?
C32 C35 C36 123.6(3) . . ?
C32 C35 H35 118.2 . . ?
C36 C35 H35 118.2 . . ?
O10 C36 O11 121.9(3) . . ?
O10 C36 C35 128.4(3) . . ?
O11 C36 C35 109.6(3) . . ?
O11 C37 H37A 109.5 . . ?
O11 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O11 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C43 C38 C39 119.6(4) . . ?
C43 C38 H38 120.2 . . ?
C39 C38 H38 120.2 . . ?
C40 C39 C38 121.2(5) . . ?
C40 C39 H39 119.4 . . ?
C38 C39 H39 119.4 . . ?
C41 C40 C39 119.5(5) . . ?
C41 C40 H40 120.2 . . ?
C39 C40 H40 120.2 . . ?
C40 C41 C42 119.5(5) . . ?
C40 C41 H41 120.2 . . ?
C42 C41 H41 120.2 . . ?
C43 C42 C41 121.8(4) . . ?
C43 C42 H42 119.1 . . ?
C41 C42 H42 119.1 . . ?
C42 C43 C38 118.4(3) . . ?
C42 C43 C44 123.2(3) . . ?
C38 C43 C44 118.4(3) . . ?
N3 C44 C43 116.5(2) . . ?
N3 C44 H44A 108.2 . . ?
C43 C44 H44A 108.2 . . ?
N3 C44 H44B 108.2 . . ?
C43 C44 H44B 108.2 . . ?
H44A C44 H44B 107.3 . . ?
O12 C45 N3 126.0(2) . . ?
O12 C45 C46 126.5(3) . . ?
N3 C45 C46 107.2(2) . . ?
C47 C46 C45 101.8(2) . . ?
C47 C46 C63 117.1(2) . . ?
C45 C46 C63 117.6(2) . . ?
C47 C46 C53 109.6(2) . . ?
C45 C46 C53 108.63(19) . . ?
C63 C46 C53 102.00(19) . . ?
C48 C47 C52 120.0(3) . . ?
C48 C47 C46 131.0(2) . . ?
C52 C47 C46 108.5(2) . . ?
C49 C48 C47 117.0(3) . . ?
C49 C48 H48 121.5 . . ?
C47 C48 H48 121.5 . . ?
F2 C49 C48 117.5(3) . . ?
F2 C49 C50 118.5(3) . . ?
C48 C49 C50 123.9(3) . . ?
C49 C50 C51 118.4(3) . . ?
C49 C50 H50 120.8 . . ?
C51 C50 H50 120.8 . . ?
C52 C51 C50 118.8(3) . . ?
C52 C51 H51 120.6 . . ?
C50 C51 H51 120.6 . . ?
C51 C52 C47 121.7(3) . . ?
C51 C52 N3 128.6(3) . . ?
C47 C52 N3 109.6(2) . . ?
C62 C53 C54 112.9(2) . . ?
C62 C53 C46 103.42(19) . . ?
C54 C53 C46 112.9(2) . . ?
C62 C53 H53 109.1 . . ?
C54 C53 H53 109.1 . . ?
C46 C53 H53 109.1 . . ?
O13 C54 C55 120.2(2) . . ?
O13 C54 C53 119.8(2) . . ?
C55 C54 C53 119.9(2) . . ?
C56 C55 C61 118.0(3) . . ?
C56 C55 C54 123.4(3) . . ?
C61 C55 C54 118.5(3) . . ?
C57 C56 C55 121.3(3) . . ?
C57 C56 H56 119.3 . . ?
C55 C56 H56 119.3 . . ?
C58 C57 C56 119.5(3) . . ?
C58 C57 H57 120.3 . . ?
C56 C57 H57 120.3 . . ?
O14 C58 C57 124.6(3) . . ?
O14 C58 C60 115.5(3) . . ?
C57 C58 C60 119.9(3) . . ?
O14 C59 H59A 109.5 . . ?
O14 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
O14 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C61 C60 C58 120.3(3) . . ?
C61 C60 H60 119.8 . . ?
C58 C60 H60 119.8 . . ?
C60 C61 C55 120.9(3) . . ?
C60 C61 H61 119.6 . . ?
C55 C61 H61 119.6 . . ?
N4 C62 C53 105.0(2) . . ?
N4 C62 H62A 110.7 . . ?
C53 C62 H62A 110.7 . . ?
N4 C62 H62B 110.7 . . ?
C53 C62 H62B 110.7 . . ?
H62A C62 H62B 108.8 . . ?
N4 C63 C66 110.5(2) . . ?
N4 C63 C64 108.2(2) . . ?
C66 C63 C64 113.2(2) . . ?
N4 C63 C46 101.34(19) . . ?
C66 C63 C46 114.4(2) . . ?
C64 C63 C46 108.4(2) . . ?
O15 C64 O16 125.0(3) . . ?
O15 C64 C63 123.6(3) . . ?
O16 C64 C63 111.4(3) . . ?
O16 C65 H65A 109.5 . . ?
O16 C65 H65B 109.5 . . ?
H65A C65 H65B 109.5 . . ?
O16 C65 H65C 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C67 C66 C63 116.8(2) . . ?
C67 C66 H66A 108.1 . . ?
C63 C66 H66A 108.1 . . ?
C67 C66 H66B 108.1 . . ?
C63 C66 H66B 108.1 . . ?
H66A C66 H66B 107.3 . . ?
O17 C67 O18 123.4(3) . . ?
O17 C67 C66 126.2(3) . . ?
O18 C67 C66 110.4(2) . . ?
O18 C68 H68A 109.5 . . ?
O18 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
O18 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C72 C69 N4 122.3(2) . . ?
C72 C69 C70 120.6(2) . . ?
N4 C69 C70 117.1(2) . . ?
O19 C70 O20 125.2(3) . . ?
O19 C70 C69 123.6(3) . . ?
O20 C70 C69 111.1(3) . . ?
O20 C71 H71A 109.5 . . ?
O20 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
O20 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C69 C72 C73 125.3(3) . . ?
C69 C72 H72 117.3 . . ?
C73 C72 H72 117.3 . . ?
O21 C73 O22 121.6(3) . . ?
O21 C73 C72 123.1(3) . . ?
O22 C73 C72 115.3(3) . . ?
O22 C74 H74A 109.5 . . ?
O22 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
O22 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C80 C75 C76 120.6(4) . . ?
C80 C75 H75 119.7 . . ?
C76 C75 H75 119.7 . . ?
C77 C76 C75 120.1(4) . . ?
C77 C76 H76 120.0 . . ?
C75 C76 H76 120.0 . . ?
C78 C77 C76 119.9(4) . . ?
C78 C77 H77 120.0 . . ?
C76 C77 H77 120.0 . . ?
C77 C78 C79 120.5(4) . . ?
C77 C78 H78 119.8 . . ?
C79 C78 H78 119.8 . . ?
C80 C79 C78 120.3(4) . . ?
C80 C79 H79 119.8 . . ?
C78 C79 H79 119.8 . . ?
C75 C80 C79 118.6(3) . . ?
C75 C80 C81 121.4(3) . . ?
C79 C80 C81 120.1(3) . . ?
N5 C81 C80 113.3(2) . . ?
N5 C81 H81A 108.9 . . ?
C80 C81 H81A 108.9 . . ?
N5 C81 H81B 108.9 . . ?
C80 C81 H81B 108.9 . . ?
H81A C81 H81B 107.7 . . ?
O23 C82 N5 126.5(3) . . ?
O23 C82 C83 125.6(3) . . ?
N5 C82 C83 107.6(2) . . ?
C84 C83 C82 101.9(2) . . ?
C84 C83 C90 110.7(2) . . ?
C82 C83 C90 107.0(2) . . ?
C84 C83 C100 116.9(2) . . ?
C82 C83 C100 117.9(2) . . ?
C90 C83 C100 102.2(2) . . ?
C85 C84 C89 119.9(3) . . ?
C85 C84 C83 131.0(3) . . ?
C89 C84 C83 108.7(2) . . ?
C84 C85 C86 117.0(3) . . ?
C84 C85 H85 121.5 . . ?
C86 C85 H85 121.5 . . ?
C87 C86 F3 119.0(3) . . ?
C87 C86 C85 123.7(3) . . ?
F3 C86 C85 117.3(3) . . ?
C86 C87 C88 119.0(3) . . ?
C86 C87 H87 120.5 . . ?
C88 C87 H87 120.5 . . ?
C89 C88 C87 118.7(3) . . ?
C89 C88 H88 120.6 . . ?
C87 C88 H88 120.6 . . ?
C88 C89 C84 121.6(3) . . ?
C88 C89 N5 128.9(3) . . ?
C84 C89 N5 109.5(3) . . ?
C99 C90 C91 114.6(2) . . ?
C99 C90 C83 103.03(19) . . ?
C91 C90 C83 112.2(2) . . ?
C99 C90 H90 109.0 . . ?
C91 C90 H90 109.0 . . ?
C83 C90 H90 109.0 . . ?
O24 C91 C92 120.3(2) . . ?
O24 C91 C90 120.4(2) . . ?
C92 C91 C90 119.2(2) . . ?
C93 C92 C98 118.2(3) . . ?
C93 C92 C91 117.5(3) . . ?
C98 C92 C91 124.3(3) . . ?
C92 C93 C94 121.3(3) . . ?
C92 C93 H93 119.4 . . ?
C94 C93 H93 119.4 . . ?
C95 C94 C93 119.3(3) . . ?
C95 C94 H94 120.3 . . ?
C93 C94 H94 120.3 . . ?
O25 C95 C94 124.0(3) . . ?
O25 C95 C97 115.8(3) . . ?
C94 C95 C97 120.3(3) . . ?
O25 C96 H96A 109.5 . . ?
O25 C96 H96B 109.5 . . ?
H96A C96 H96B 109.5 . . ?
O25 C96 H96C 109.5 . . ?
H96A C96 H96C 109.5 . . ?
H96B C96 H96C 109.5 . . ?
C95 C97 C98 120.5(3) . . ?
C95 C97 H97 119.8 . . ?
C98 C97 H97 119.8 . . ?
C97 C98 C92 120.4(3) . . ?
C97 C98 H98 119.8 . . ?
C92 C98 H98 119.8 . . ?
N6 C99 C90 104.8(2) . . ?
N6 C99 H99A 110.8 . . ?
C90 C99 H99A 110.8 . . ?
N6 C99 H99B 110.8 . . ?
C90 C99 H99B 110.8 . . ?
H99A C99 H99B 108.9 . . ?
N6 C100 C101 111.2(2) . . ?
N6 C100 C103 110.7(2) . . ?
C101 C100 C103 108.6(2) . . ?
N6 C100 C83 100.64(19) . . ?
C101 C100 C83 111.6(2) . . ?
C103 C100 C83 113.9(2) . . ?
O26 C101 O27 125.3(3) . . ?
O26 C101 C100 123.6(3) . . ?
O27 C101 C100 111.2(3) . . ?
O27 C102 H02A 109.5 . . ?
O27 C102 H02B 109.5 . . ?
H02A C102 H02B 109.5 . . ?
O27 C102 H02C 109.5 . . ?
H02A C102 H02C 109.5 . . ?
H02B C102 H02C 109.5 . . ?
C104 C103 C100 115.3(2) . . ?
C104 C103 H03D 108.5 . . ?
C100 C103 H03D 108.5 . . ?
C104 C103 H03E 108.5 . . ?
C100 C103 H03E 108.5 . . ?
H03D C103 H03E 107.5 . . ?
O28 C104 O29 123.3(3) . . ?
O28 C104 C103 126.8(3) . . ?
O29 C104 C103 109.8(3) . . ?
O29 C105 H05A 109.5 . . ?
O29 C105 H05B 109.5 . . ?
H05A C105 H05B 109.5 . . ?
O29 C105 H05C 109.5 . . ?
H05A C105 H05C 109.5 . . ?
H05B C105 H05C 109.5 . . ?
C109 C106 N6 123.2(2) . . ?
C109 C106 C107 119.3(2) . . ?
N6 C106 C107 117.5(2) . . ?
O30 C107 O31 125.3(3) . . ?
O30 C107 C106 123.7(3) . . ?
O31 C107 C106 110.9(3) . . ?
O31 C108 H08A 109.5 . . ?
O31 C108 H08B 109.5 . . ?
H08A C108 H08B 109.5 . . ?
O31 C108 H08C 109.5 . . ?
H08A C108 H08C 109.5 . . ?
H08B C108 H08C 109.5 . . ?
C106 C109 C110 122.2(3) . . ?
C106 C109 H09A 118.9 . . ?
C110 C109 H09A 118.9 . . ?
O32 C110 O33 121.4(3) . . ?
O32 C110 C109 127.9(3) . . ?
O33 C110 C109 110.8(3) . . ?
O33 C111 H11A 109.5 . . ?
O33 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
O33 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
C8 N1 C15 111.1(2) . . ?
C8 N1 C7 122.7(3) . . ?
C15 N1 C7 125.8(3) . . ?
C32 N2 C25 116.9(2) . . ?
C32 N2 C26 127.9(2) . . ?
C25 N2 C26 113.1(2) . . ?
C45 N3 C52 111.5(2) . . ?
C45 N3 C44 122.9(2) . . ?
C52 N3 C44 125.4(2) . . ?
C69 N4 C62 118.6(2) . . ?
C69 N4 C63 127.2(2) . . ?
C62 N4 C63 113.10(19) . . ?
C82 N5 C89 111.5(2) . . ?
C82 N5 C81 123.1(3) . . ?
C89 N5 C81 125.4(3) . . ?
C106 N6 C99 118.4(2) . . ?
C106 N6 C100 127.2(2) . . ?
C99 N6 C100 113.27(19) . . ?
C21 O3 C22 117.4(3) . . ?
C27 O5 C28 116.3(2) . . ?
C30 O7 C31 115.8(2) . . ?
C33 O8 C34' 105.6(6) . . ?
C33 O9 C34 109.2(4) . . ?
C36 O11 C37 116.9(2) . . ?
C58 O14 C59 117.6(3) . . ?
C64 O16 C65 114.6(2) . . ?
C67 O18 C68 116.9(2) . . ?
C70 O20 C71 115.9(2) . . ?
C73 O22 C74 118.3(3) . . ?
C95 O25 C96 117.4(3) . . ?
C101 O27 C102 115.9(3) . . ?
C104 O29 C105 116.0(2) . . ?
C107 O31 C108 115.6(3) . . ?
C110 O33 C111 115.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.044
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4e
_audit_block_doi                 10.5517/cc1492zh
_database_code_depnum_ccdc_archive 'CCDC 1051426'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H37 Cl N2 O10'
_chemical_formula_sum            'C34 H37 Cl N2 O10'
_chemical_formula_weight         669.11

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                   10.5329(12)
_cell_length_b                   10.6066(11)
_cell_length_c                   19.252(2)
_cell_angle_alpha                104.723(3)
_cell_angle_beta                 97.305(3)
_cell_angle_gamma                107.595(3)
_cell_volume                     1933.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_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_reflns_number            27745
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         27.57
_reflns_number_total             8645
_reflns_number_gt                5313
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1923P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8645
_refine_ls_number_parameters     431
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0894
_refine_ls_wR_factor_ref         0.2992
_refine_ls_wR_factor_gt          0.2795
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.124
_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 0.4818(10) 1.4458(8) 0.3265(5) 0.190(3) Uani 1 1 d U . .
H1A H 0.4608 1.4362 0.3724 0.286 Uiso 1 1 calc R . .
H1B H 0.4907 1.5378 0.3250 0.286 Uiso 1 1 calc R . .
H1C H 0.5660 1.4303 0.3220 0.286 Uiso 1 1 calc R . .
C2 C 0.3762(7) 1.3477(5) 0.2680(3) 0.1247(17) Uani 1 1 d U . .
H2A H 0.4015 1.3520 0.2217 0.150 Uiso 1 1 calc R . .
H2B H 0.2941 1.3710 0.2690 0.150 Uiso 1 1 calc R . .
C3 C 0.3455(5) 1.1974(4) 0.2719(3) 0.1009(13) Uani 1 1 d U . .
H3A H 0.4252 1.1712 0.2667 0.121 Uiso 1 1 calc R . .
H3B H 0.3271 1.1946 0.3197 0.121 Uiso 1 1 calc R . .
C4 C 0.2319(5) 1.1005(4) 0.2159(3) 0.0869(11) Uani 1 1 d U . .
H4A H 0.2540 1.1004 0.1685 0.104 Uiso 1 1 calc R . .
H4B H 0.1553 1.1328 0.2189 0.104 Uiso 1 1 calc R . .
C5 C 0.0743(3) 0.8967(3) 0.23990(14) 0.0408(6) Uani 1 1 d . . .
C6 C 0.0485(2) 0.7380(2) 0.22116(13) 0.0361(6) Uani 1 1 d . . .
C7 C 0.1638(3) 0.7249(3) 0.18455(13) 0.0403(6) Uani 1 1 d . . .
C8 C 0.2428(3) 0.8561(3) 0.18409(16) 0.0471(7) Uani 1 1 d . . .
C9 C 0.3587(3) 0.8776(4) 0.1549(2) 0.0649(9) Uani 1 1 d . . .
H9 H 0.4116 0.9662 0.1559 0.078 Uiso 1 1 calc R . .
C10 C 0.3924(3) 0.7628(4) 0.1243(2) 0.0660(9) Uani 1 1 d . . .
H10 H 0.4686 0.7738 0.1036 0.079 Uiso 1 1 calc R . .
C11 C 0.3151(3) 0.6328(3) 0.12411(16) 0.0539(7) Uani 1 1 d . . .
C12 C 0.1995(3) 0.6104(3) 0.15440(14) 0.0449(6) Uani 1 1 d . . .
H12 H 0.1483 0.5219 0.1543 0.054 Uiso 1 1 calc R . .
C13 C 0.0525(3) 0.6948(3) 0.29297(14) 0.0443(6) Uani 1 1 d . . .
H13 H 0.0077 0.7453 0.3255 0.053 Uiso 1 1 calc R . .
C14 C 0.1970(3) 0.7262(3) 0.33407(15) 0.0551(7) Uani 1 1 d . . .
C15 C 0.2832(4) 0.8713(4) 0.37401(18) 0.0660(9) Uani 1 1 d . . .
C16 C 0.2313(5) 0.9652(4) 0.41353(19) 0.0826(11) Uani 1 1 d . . .
H16 H 0.1388 0.9397 0.4138 0.099 Uiso 1 1 calc R . .
C17 C 0.3219(8) 1.0997(5) 0.4532(3) 0.122(2) Uani 1 1 d . . .
H17 H 0.2895 1.1632 0.4814 0.147 Uiso 1 1 calc R . .
C18 C 0.4603(9) 1.1400(7) 0.4509(4) 0.151(3) Uani 1 1 d . . .
C19 C 0.5594(11) 1.2872(8) 0.4904(6) 0.256(7) Uani 1 1 d . . .
H19A H 0.6386 1.2838 0.5195 0.384 Uiso 1 1 calc R . .
H19B H 0.5157 1.3379 0.5217 0.384 Uiso 1 1 calc R . .
H19C H 0.5864 1.3328 0.4547 0.384 Uiso 1 1 calc R . .
C20 C 0.5058(7) 1.0424(8) 0.4093(5) 0.154(3) Uani 1 1 d . . .
H20 H 0.5973 1.0668 0.4069 0.185 Uiso 1 1 calc R . .
C21 C 0.4211(4) 0.9157(6) 0.3732(3) 0.1119(17) Uani 1 1 d . . .
H21 H 0.4552 0.8529 0.3459 0.134 Uiso 1 1 calc R . .
C22 C -0.0325(3) 0.5403(3) 0.26761(16) 0.0562(8) Uani 1 1 d . . .
H22A H 0.0257 0.4846 0.2621 0.067 Uiso 1 1 calc R . .
H22B H -0.0870 0.5176 0.3027 0.067 Uiso 1 1 calc R . .
C23 C -0.0984(2) 0.6420(2) 0.17325(13) 0.0348(5) Uani 1 1 d . . .
C24 C -0.2091(3) 0.7050(3) 0.19236(15) 0.0435(6) Uani 1 1 d . . .
C25 C -0.3190(4) 0.7762(5) 0.2870(2) 0.0888(12) Uani 1 1 d . . .
H25A H -0.2901 0.8681 0.2823 0.133 Uiso 1 1 calc R . .
H25B H -0.3165 0.7825 0.3378 0.133 Uiso 1 1 calc R . .
H25C H -0.4105 0.7250 0.2586 0.133 Uiso 1 1 calc R . .
C26 C -0.1028(3) 0.6065(3) 0.08976(14) 0.0409(6) Uani 1 1 d . . .
H26A H -0.0549 0.5417 0.0770 0.049 Uiso 1 1 calc R . .
H26B H -0.1973 0.5594 0.0633 0.049 Uiso 1 1 calc R . .
C27 C -0.0429(3) 0.7264(3) 0.06407(14) 0.0422(6) Uani 1 1 d . . .
C28 C 0.0492(7) 0.7855(5) -0.0342(3) 0.134(2) Uani 1 1 d . . .
H28A H 0.0080 0.8555 -0.0240 0.201 Uiso 1 1 calc R . .
H28B H 0.0306 0.7424 -0.0865 0.201 Uiso 1 1 calc R . .
H28C H 0.1461 0.8276 -0.0153 0.201 Uiso 1 1 calc R . .
C29 C -0.2362(3) 0.4004(3) 0.16915(14) 0.0399(6) Uani 1 1 d . . .
C30 C -0.2364(3) 0.2891(3) 0.20604(16) 0.0475(7) Uani 1 1 d . . .
C31 C -0.1866(5) 0.0865(4) 0.1970(2) 0.0963(15) Uani 1 1 d . . .
H31A H -0.1445 0.1176 0.2485 0.144 Uiso 1 1 calc R . .
H31B H -0.1400 0.0328 0.1698 0.144 Uiso 1 1 calc R . .
H31C H -0.2806 0.0300 0.1894 0.144 Uiso 1 1 calc R . .
C32 C -0.3441(3) 0.3781(3) 0.11666(16) 0.0461(7) Uani 1 1 d . . .
H32 H -0.3484 0.4508 0.0989 0.055 Uiso 1 1 calc R . .
C33 C -0.4543(3) 0.2453(3) 0.08665(16) 0.0478(7) Uani 1 1 d . . .
C34 C -0.6610(3) 0.1206(4) -0.0013(2) 0.0724(10) Uani 1 1 d . . .
H34A H -0.6301 0.0432 -0.0145 0.109 Uiso 1 1 calc R . .
H34B H -0.7107 0.1275 -0.0447 0.109 Uiso 1 1 calc R . .
H34C H -0.7195 0.1070 0.0326 0.109 Uiso 1 1 calc R . .
Cl1 Cl 0.36332(9) 0.49241(10) 0.08575(5) 0.0755(4) Uani 1 1 d . . .
N1 N 0.1877(2) 0.9553(2) 0.21809(14) 0.0528(6) Uani 1 1 d . . .
N2 N -0.1203(2) 0.5158(2) 0.19644(11) 0.0394(5) Uani 1 1 d . . .
O1 O 0.0048(2) 0.9558(2) 0.27049(11) 0.0525(5) Uani 1 1 d . . .
O2 O 0.2435(3) 0.6341(3) 0.33117(15) 0.0900(9) Uani 1 1 d . . .
O3 O -0.2714(2) 0.7444(2) 0.15247(12) 0.0587(6) Uani 1 1 d . . .
O4 O -0.2282(2) 0.7053(2) 0.26006(11) 0.0573(6) Uani 1 1 d . . .
O5 O -0.0286(2) 0.8452(2) 0.09168(11) 0.0585(6) Uani 1 1 d . . .
O6 O -0.0075(3) 0.6801(2) 0.00101(13) 0.0812(8) Uani 1 1 d . . .
O7 O -0.2804(3) 0.2829(3) 0.25908(14) 0.0764(7) Uani 1 1 d . . .
O8 O -0.1783(2) 0.2057(2) 0.17193(11) 0.0590(6) Uani 1 1 d . . .
O9 O -0.4664(2) 0.1443(2) 0.10765(15) 0.0794(8) Uani 1 1 d . . .
O10 O -0.54600(19) 0.24567(19) 0.03265(11) 0.0536(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 C2 1.405(10) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.551(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.419(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.481(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.214(3) . ?
C5 N1 1.342(4) . ?
C5 C6 1.558(3) . ?
C6 C7 1.504(3) . ?
C6 C13 1.563(3) . ?
C6 C23 1.578(3) . ?
C7 C12 1.387(4) . ?
C7 C8 1.392(4) . ?
C8 C9 1.389(4) . ?
C8 N1 1.410(4) . ?
C9 C10 1.381(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.399(4) . ?
C11 Cl1 1.736(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.518(4) . ?
C13 C22 1.523(4) . ?
C13 H13 0.9800 . ?
C14 O2 1.211(4) . ?
C14 C15 1.470(5) . ?
C15 C16 1.386(6) . ?
C15 C21 1.388(6) . ?
C16 C17 1.402(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(11) . ?
C17 H17 0.9300 . ?
C18 C20 1.384(12) . ?
C18 C19 1.522(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.314(9) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 N2 1.466(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 N2 1.479(3) . ?
C23 C26 1.546(3) . ?
C23 C24 1.548(3) . ?
C24 O3 1.181(3) . ?
C24 O4 1.343(3) . ?
C25 O4 1.454(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.475(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 O5 1.191(3) . ?
C27 O6 1.333(3) . ?
C28 O6 1.467(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C32 1.340(4) . ?
C29 N2 1.368(3) . ?
C29 C30 1.524(4) . ?
C30 O7 1.182(3) . ?
C30 O8 1.312(3) . ?
C31 O8 1.447(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.446(4) . ?
C32 H32 0.9300 . ?
C33 O9 1.216(3) . ?
C33 O10 1.328(3) . ?
C34 O10 1.428(4) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 112.2(6) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 111.8(5) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 N1 116.1(4) . . ?
C3 C4 H4A 108.3 . . ?
N1 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
N1 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
O1 C5 N1 126.8(2) . . ?
O1 C5 C6 125.3(2) . . ?
N1 C5 C6 107.9(2) . . ?
C7 C6 C5 101.9(2) . . ?
C7 C6 C13 113.3(2) . . ?
C5 C6 C13 110.3(2) . . ?
C7 C6 C23 114.65(19) . . ?
C5 C6 C23 114.16(18) . . ?
C13 C6 C23 102.84(18) . . ?
C12 C7 C8 119.8(2) . . ?
C12 C7 C6 131.5(2) . . ?
C8 C7 C6 108.7(2) . . ?
C9 C8 C7 122.1(3) . . ?
C9 C8 N1 128.3(3) . . ?
C7 C8 N1 109.5(2) . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.9(3) . . ?
C10 C11 Cl1 118.9(2) . . ?
C12 C11 Cl1 119.2(2) . . ?
C7 C12 C11 117.7(3) . . ?
C7 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C14 C13 C22 112.8(2) . . ?
C14 C13 C6 112.7(2) . . ?
C22 C13 C6 104.9(2) . . ?
C14 C13 H13 108.7 . . ?
C22 C13 H13 108.7 . . ?
C6 C13 H13 108.7 . . ?
O2 C14 C15 120.0(3) . . ?
O2 C14 C13 120.7(3) . . ?
C15 C14 C13 119.2(3) . . ?
C16 C15 C21 118.7(4) . . ?
C16 C15 C14 121.9(3) . . ?
C21 C15 C14 119.4(4) . . ?
C15 C16 C17 118.3(5) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C18 C17 C16 121.0(6) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C20 C18 C17 118.1(5) . . ?
C20 C18 C19 119.8(10) . . ?
C17 C18 C19 122.1(10) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C18 120.7(7) . . ?
C21 C20 H20 119.6 . . ?
C18 C20 H20 119.6 . . ?
C20 C21 C15 123.1(7) . . ?
C20 C21 H21 118.4 . . ?
C15 C21 H21 118.4 . . ?
N2 C22 C13 105.0(2) . . ?
N2 C22 H22A 110.7 . . ?
C13 C22 H22A 110.7 . . ?
N2 C22 H22B 110.7 . . ?
C13 C22 H22B 110.7 . . ?
H22A C22 H22B 108.8 . . ?
N2 C23 C26 110.38(19) . . ?
N2 C23 C24 109.40(19) . . ?
C26 C23 C24 110.57(19) . . ?
N2 C23 C6 101.71(17) . . ?
C26 C23 C6 112.19(19) . . ?
C24 C23 C6 112.24(19) . . ?
O3 C24 O4 124.1(2) . . ?
O3 C24 C23 125.0(2) . . ?
O4 C24 C23 110.8(2) . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C23 115.3(2) . . ?
C27 C26 H26A 108.4 . . ?
C23 C26 H26A 108.4 . . ?
C27 C26 H26B 108.4 . . ?
C23 C26 H26B 108.4 . . ?
H26A C26 H26B 107.5 . . ?
O5 C27 O6 123.4(3) . . ?
O5 C27 C26 128.4(2) . . ?
O6 C27 C26 108.2(2) . . ?
O6 C28 H28A 109.5 . . ?
O6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C32 C29 N2 127.7(2) . . ?
C32 C29 C30 119.3(2) . . ?
N2 C29 C30 112.9(2) . . ?
O7 C30 O8 125.8(3) . . ?
O7 C30 C29 123.7(3) . . ?
O8 C30 C29 110.5(2) . . ?
O8 C31 H31A 109.5 . . ?
O8 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O8 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 C33 122.5(2) . . ?
C29 C32 H32 118.8 . . ?
C33 C32 H32 118.8 . . ?
O9 C33 O10 122.3(2) . . ?
O9 C33 C32 125.9(3) . . ?
O10 C33 C32 111.7(2) . . ?
O10 C34 H34A 109.5 . . ?
O10 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O10 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C5 N1 C8 111.9(2) . . ?
C5 N1 C4 123.2(3) . . ?
C8 N1 C4 123.7(3) . . ?
C29 N2 C22 119.7(2) . . ?
C29 N2 C23 123.61(19) . . ?
C22 N2 C23 113.6(2) . . ?
C24 O4 C25 115.4(2) . . ?
C27 O6 C28 115.6(3) . . ?
C30 O8 C31 115.3(3) . . ?
C33 O10 C34 117.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.104

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 -0.010 0.500 331 124 ' '
_platon_squeeze_details          
; 
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4i
_audit_block_doi                 10.5517/cc14930k
_database_code_depnum_ccdc_archive 'CCDC 1051427'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H42 N2 O10'
_chemical_formula_sum            'C44 H42 N2 O10'
_chemical_formula_weight         758.80

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   '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                   15.9722(18)
_cell_length_b                   8.9978(10)
_cell_length_c                   27.367(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.485(4)
_cell_angle_gamma                90.00
_cell_volume                     3921.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8672
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      22.42

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.977
_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            40946
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0829
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.62
_reflns_number_total             9030
_reflns_number_gt                4344
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0859P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0199(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9030
_refine_ls_number_parameters     511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 -0.16054(15) 0.5879(3) 0.08362(11) 0.0752(8) Uani 1 1 d . . .
H1 H -0.1668 0.6182 0.0510 0.090 Uiso 1 1 calc R . .
C2 C -0.22892(18) 0.5369(4) 0.10585(16) 0.0982(11) Uani 1 1 d . . .
H2 H -0.2811 0.5330 0.0883 0.118 Uiso 1 1 calc R . .
C3 C -0.22110(18) 0.4919(4) 0.15346(17) 0.0918(11) Uani 1 1 d . . .
H3 H -0.2677 0.4578 0.1685 0.110 Uiso 1 1 calc R . .
C4 C -0.14406(18) 0.4974(3) 0.17896(13) 0.0833(9) Uani 1 1 d . . .
H4 H -0.1381 0.4675 0.2116 0.100 Uiso 1 1 calc R . .
C5 C -0.07512(16) 0.5473(3) 0.15620(11) 0.0667(8) Uani 1 1 d . . .
H5 H -0.0227 0.5484 0.1735 0.080 Uiso 1 1 calc R . .
C6 C -0.08277(13) 0.5949(3) 0.10890(9) 0.0526(6) Uani 1 1 d . . .
C7 C -0.01045(13) 0.6630(3) 0.08438(9) 0.0589(7) Uani 1 1 d . . .
H7A H -0.0227 0.6575 0.0491 0.071 Uiso 1 1 calc R . .
H7B H -0.0066 0.7674 0.0932 0.071 Uiso 1 1 calc R . .
C8 C 0.13996(13) 0.6726(3) 0.11402(8) 0.0444(6) Uani 1 1 d . . .
C9 C 0.21732(12) 0.5705(2) 0.11281(8) 0.0401(5) Uani 1 1 d . . .
C10 C 0.18016(13) 0.4330(2) 0.08770(8) 0.0406(5) Uani 1 1 d . . .
C11 C 0.21484(14) 0.3001(3) 0.07509(8) 0.0497(6) Uani 1 1 d . . .
H11 H 0.2721 0.2830 0.0813 0.060 Uiso 1 1 calc R . .
C12 C 0.16250(16) 0.1907(3) 0.05271(9) 0.0574(7) Uani 1 1 d . . .
H12 H 0.1851 0.1000 0.0441 0.069 Uiso 1 1 calc R . .
C13 C 0.07790(16) 0.2166(3) 0.04340(9) 0.0569(7) Uani 1 1 d . . .
H13 H 0.0443 0.1434 0.0280 0.068 Uiso 1 1 calc R . .
C14 C 0.04172(14) 0.3482(3) 0.05637(8) 0.0520(6) Uani 1 1 d . . .
H14 H -0.0156 0.3650 0.0501 0.062 Uiso 1 1 calc R . .
C15 C 0.09364(13) 0.4541(3) 0.07904(8) 0.0420(6) Uani 1 1 d . . .
C16 C 0.25927(12) 0.5407(2) 0.16541(8) 0.0405(5) Uani 1 1 d . . .
H16 H 0.2612 0.6347 0.1835 0.049 Uiso 1 1 calc R . .
C17 C 0.21429(13) 0.4254(3) 0.19518(8) 0.0426(6) Uani 1 1 d . . .
C18 C 0.15528(13) 0.4769(3) 0.23101(8) 0.0453(6) Uani 1 1 d . . .
C19 C 0.12831(15) 0.6214(3) 0.23476(9) 0.0580(7) Uani 1 1 d . . .
H19 H 0.1486 0.6939 0.2145 0.070 Uiso 1 1 calc R . .
C20 C 0.07125(16) 0.6606(3) 0.26823(10) 0.0684(8) Uani 1 1 d . . .
H20 H 0.0522 0.7582 0.2691 0.082 Uiso 1 1 calc R . .
C21 C 0.04232(17) 0.5584(4) 0.30002(10) 0.0688(8) Uani 1 1 d . . .
C22 C -0.0187(2) 0.6025(4) 0.33683(12) 0.1029(12) Uani 1 1 d . . .
H22A H -0.0137 0.5351 0.3641 0.154 Uiso 1 1 calc R . .
H22B H -0.0750 0.5987 0.3217 0.154 Uiso 1 1 calc R . .
H22C H -0.0064 0.7017 0.3482 0.154 Uiso 1 1 calc R . .
C23 C 0.0711(2) 0.4168(4) 0.29684(12) 0.0956(11) Uani 1 1 d . . .
H23 H 0.0528 0.3455 0.3182 0.115 Uiso 1 1 calc R . .
C24 C 0.12636(19) 0.3750(3) 0.26308(10) 0.0779(9) Uani 1 1 d . . .
H24 H 0.1443 0.2767 0.2620 0.094 Uiso 1 1 calc R . .
C25 C 0.35346(18) 0.5897(4) 0.27919(11) 0.0839(9) Uani 1 1 d . . .
H25 H 0.3438 0.6882 0.2701 0.101 Uiso 1 1 calc R . .
C26 C 0.3288(2) 0.5415(7) 0.32307(14) 0.1264(16) Uani 1 1 d . . .
H26 H 0.3019 0.6060 0.3433 0.152 Uiso 1 1 calc R . .
C27 C 0.3436(3) 0.4019(8) 0.33666(16) 0.136(2) Uani 1 1 d . . .
H27 H 0.3272 0.3704 0.3668 0.163 Uiso 1 1 calc R . .
C28 C 0.3821(3) 0.3024(6) 0.30787(17) 0.1232(15) Uani 1 1 d . . .
H28 H 0.3914 0.2048 0.3180 0.148 Uiso 1 1 calc R . .
C29 C 0.40727(19) 0.3520(4) 0.26256(12) 0.0888(10) Uani 1 1 d . . .
H29 H 0.4341 0.2873 0.2424 0.107 Uiso 1 1 calc R . .
C30 C 0.39199(15) 0.4972(3) 0.24809(9) 0.0595(7) Uani 1 1 d . . .
C31 C 0.41293(14) 0.5506(3) 0.19852(8) 0.0561(7) Uani 1 1 d . . .
H31A H 0.4688 0.5164 0.1924 0.067 Uiso 1 1 calc R . .
H31B H 0.4135 0.6584 0.1983 0.067 Uiso 1 1 calc R . .
C32 C 0.34983(12) 0.4949(3) 0.15716(8) 0.0418(6) Uani 1 1 d . . .
H32 H 0.3531 0.3863 0.1552 0.050 Uiso 1 1 calc R . .
C33 C 0.44382(12) 0.5714(2) 0.09339(8) 0.0418(6) Uani 1 1 d . . .
C34 C 0.49941(14) 0.4378(3) 0.10354(9) 0.0494(6) Uani 1 1 d . . .
C35 C 0.5224(2) 0.1881(4) 0.08403(15) 0.1131(13) Uani 1 1 d . . .
H35A H 0.5781 0.2136 0.0762 0.170 Uiso 1 1 calc R . .
H35B H 0.4998 0.1133 0.0617 0.170 Uiso 1 1 calc R . .
H35C H 0.5242 0.1507 0.1169 0.170 Uiso 1 1 calc R . .
C36 C 0.47289(13) 0.6899(3) 0.06972(8) 0.0495(6) Uani 1 1 d . . .
H36 H 0.4403 0.7757 0.0680 0.059 Uiso 1 1 calc R . .
C37 C 0.55158(15) 0.6921(3) 0.04680(9) 0.0502(6) Uani 1 1 d . . .
C38 C 0.65168(18) 0.8510(4) 0.01505(11) 0.0943(10) Uani 1 1 d . . .
H38A H 0.6976 0.8252 0.0382 0.141 Uiso 1 1 calc R . .
H38B H 0.6572 0.9528 0.0053 0.141 Uiso 1 1 calc R . .
H38C H 0.6523 0.7878 -0.0132 0.141 Uiso 1 1 calc R . .
C39 C 0.29179(12) 0.6455(2) 0.08701(8) 0.0404(6) Uani 1 1 d . . .
C40 C 0.30040(14) 0.8133(3) 0.09943(10) 0.0494(6) Uani 1 1 d . . .
C41 C 0.3260(3) 0.9926(3) 0.16167(13) 0.1048(12) Uani 1 1 d . . .
H41A H 0.3619 1.0492 0.1421 0.157 Uiso 1 1 calc R . .
H41B H 0.3466 0.9985 0.1955 0.157 Uiso 1 1 calc R . .
H41C H 0.2700 1.0319 0.1577 0.157 Uiso 1 1 calc R . .
C42 C 0.28575(14) 0.6281(3) 0.03091(8) 0.0495(6) Uani 1 1 d . . .
H42A H 0.3388 0.6584 0.0191 0.059 Uiso 1 1 calc R . .
H42B H 0.2779 0.5237 0.0231 0.059 Uiso 1 1 calc R . .
C43 C 0.21663(16) 0.7148(3) 0.00356(9) 0.0533(6) Uani 1 1 d . . .
C44 C 0.17959(18) 0.8556(4) -0.06733(11) 0.0904(10) Uani 1 1 d . . .
H44A H 0.1412 0.7839 -0.0823 0.136 Uiso 1 1 calc R . .
H44B H 0.2056 0.9095 -0.0924 0.136 Uiso 1 1 calc R . .
H44C H 0.1496 0.9236 -0.0480 0.136 Uiso 1 1 calc R . .
N1 N 0.07081(10) 0.5936(2) 0.09686(7) 0.0459(5) Uani 1 1 d . . .
N2 N 0.36401(10) 0.55955(19) 0.10886(6) 0.0410(5) Uani 1 1 d . . .
O1 O 0.14048(10) 0.80004(19) 0.12884(6) 0.0591(5) Uani 1 1 d . . .
O2 O 0.22834(10) 0.29441(19) 0.18991(6) 0.0584(5) Uani 1 1 d . . .
O3 O 0.56214(11) 0.4369(2) 0.13094(7) 0.0764(6) Uani 1 1 d . . .
O4 O 0.46944(11) 0.3193(2) 0.07987(7) 0.0717(5) Uani 1 1 d . . .
O5 O 0.59305(11) 0.5846(2) 0.03719(7) 0.0725(5) Uani 1 1 d . . .
O6 O 0.57349(10) 0.8318(2) 0.03731(6) 0.0697(5) Uani 1 1 d . . .
O7 O 0.28999(11) 0.90934(19) 0.06891(7) 0.0674(5) Uani 1 1 d . . .
O8 O 0.32524(10) 0.83839(17) 0.14594(6) 0.0594(5) Uani 1 1 d . . .
O9 O 0.14483(11) 0.7201(2) 0.01370(6) 0.0755(6) Uani 1 1 d . . .
O10 O 0.24362(10) 0.7799(2) -0.03604(6) 0.0662(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 C2 1.370(4) . ?
C1 C6 1.375(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.511(3) . ?
C7 N1 1.457(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.216(3) . ?
C8 N1 1.365(3) . ?
C8 C9 1.542(3) . ?
C9 C10 1.514(3) . ?
C9 C16 1.563(3) . ?
C9 C39 1.581(3) . ?
C10 C11 1.373(3) . ?
C10 C15 1.397(3) . ?
C11 C12 1.401(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.404(3) . ?
C16 C17 1.533(3) . ?
C16 C32 1.538(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.210(3) . ?
C17 C18 1.486(3) . ?
C18 C24 1.374(3) . ?
C18 C19 1.376(3) . ?
C19 C20 1.388(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(4) . ?
C20 H20 0.9300 . ?
C21 C23 1.360(4) . ?
C21 C22 1.509(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.379(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.364(5) . ?
C25 C30 1.370(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.326(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.406(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.501(3) . ?
C31 C32 1.539(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N2 1.478(3) . ?
C32 H32 0.9800 . ?
C33 C36 1.349(3) . ?
C33 N2 1.378(3) . ?
C33 C34 1.507(3) . ?
C34 O3 1.204(3) . ?
C34 O4 1.318(3) . ?
C35 O4 1.451(3) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.448(3) . ?
C36 H36 0.9300 . ?
C37 O5 1.212(3) . ?
C37 O6 1.335(3) . ?
C38 O6 1.442(3) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 N2 1.476(2) . ?
C39 C42 1.538(3) . ?
C39 C40 1.552(3) . ?
C40 O7 1.204(3) . ?
C40 O8 1.323(3) . ?
C41 O8 1.452(3) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C43 1.502(3) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 O9 1.202(3) . ?
C43 O10 1.333(3) . ?
C44 O10 1.451(3) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 122.4(2) . . ?
C1 C6 C7 119.1(2) . . ?
N1 C7 C6 114.82(19) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
O1 C8 N1 126.1(2) . . ?
O1 C8 C9 125.7(2) . . ?
N1 C8 C9 108.1(2) . . ?
C10 C9 C8 102.13(17) . . ?
C10 C9 C16 113.75(17) . . ?
C8 C9 C16 111.65(17) . . ?
C10 C9 C39 115.35(17) . . ?
C8 C9 C39 112.78(17) . . ?
C16 C9 C39 101.61(15) . . ?
C11 C10 C15 119.3(2) . . ?
C11 C10 C9 132.39(19) . . ?
C15 C10 C9 108.26(19) . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 117.5(2) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C10 122.3(2) . . ?
C14 C15 N1 127.6(2) . . ?
C10 C15 N1 110.07(19) . . ?
C17 C16 C32 112.47(17) . . ?
C17 C16 C9 114.89(17) . . ?
C32 C16 C9 104.55(16) . . ?
C17 C16 H16 108.2 . . ?
C32 C16 H16 108.2 . . ?
C9 C16 H16 108.2 . . ?
O2 C17 C18 121.0(2) . . ?
O2 C17 C16 119.8(2) . . ?
C18 C17 C16 119.2(2) . . ?
C24 C18 C19 117.4(2) . . ?
C24 C18 C17 118.4(2) . . ?
C19 C18 C17 124.2(2) . . ?
C18 C19 C20 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C23 C21 C20 117.1(2) . . ?
C23 C21 C22 121.9(3) . . ?
C20 C21 C22 121.0(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 C24 122.4(3) . . ?
C21 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C18 C24 C23 120.7(3) . . ?
C18 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C30 121.9(4) . . ?
C26 C25 H25 119.1 . . ?
C30 C25 H25 119.1 . . ?
C27 C26 C25 119.4(4) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 122.4(4) . . ?
C26 C27 H27 118.8 . . ?
C28 C27 H27 118.8 . . ?
C27 C28 C29 118.2(4) . . ?
C27 C28 H28 120.9 . . ?
C29 C28 H28 120.9 . . ?
C30 C29 C28 119.8(4) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C25 C30 C29 118.3(3) . . ?
C25 C30 C31 120.6(3) . . ?
C29 C30 C31 121.0(3) . . ?
C30 C31 C32 112.39(19) . . ?
C30 C31 H31A 109.1 . . ?
C32 C31 H31A 109.1 . . ?
C30 C31 H31B 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.9 . . ?
N2 C32 C16 103.74(16) . . ?
N2 C32 C31 113.09(17) . . ?
C16 C32 C31 111.97(19) . . ?
N2 C32 H32 109.3 . . ?
C16 C32 H32 109.3 . . ?
C31 C32 H32 109.3 . . ?
C36 C33 N2 124.72(19) . . ?
C36 C33 C34 119.95(19) . . ?
N2 C33 C34 115.31(19) . . ?
O3 C34 O4 123.6(2) . . ?
O3 C34 C33 124.7(2) . . ?
O4 C34 C33 111.62(19) . . ?
O4 C35 H35A 109.5 . . ?
O4 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O4 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 C37 124.2(2) . . ?
C33 C36 H36 117.9 . . ?
C37 C36 H36 117.9 . . ?
O5 C37 O6 123.5(2) . . ?
O5 C37 C36 126.2(2) . . ?
O6 C37 C36 110.3(2) . . ?
O6 C38 H38A 109.5 . . ?
O6 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O6 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N2 C39 C42 109.71(16) . . ?
N2 C39 C40 111.60(17) . . ?
C42 C39 C40 108.36(18) . . ?
N2 C39 C9 100.76(15) . . ?
C42 C39 C9 114.30(17) . . ?
C40 C39 C9 111.99(17) . . ?
O7 C40 O8 124.1(2) . . ?
O7 C40 C39 122.8(2) . . ?
O8 C40 C39 113.0(2) . . ?
O8 C41 H41A 109.5 . . ?
O8 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O8 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C39 115.52(19) . . ?
C43 C42 H42A 108.4 . . ?
C39 C42 H42A 108.4 . . ?
C43 C42 H42B 108.4 . . ?
C39 C42 H42B 108.4 . . ?
H42A C42 H42B 107.5 . . ?
O9 C43 O10 123.0(2) . . ?
O9 C43 C42 125.6(2) . . ?
O10 C43 C42 111.2(2) . . ?
O10 C44 H44A 109.5 . . ?
O10 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
O10 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C8 N1 C15 111.07(18) . . ?
C8 N1 C7 122.6(2) . . ?
C15 N1 C7 123.54(19) . . ?
C33 N2 C39 123.19(17) . . ?
C33 N2 C32 121.00(16) . . ?
C39 N2 C32 113.53(15) . . ?
C34 O4 C35 115.6(2) . . ?
C37 O6 C38 116.3(2) . . ?
C40 O8 C41 116.3(2) . . ?
C43 O10 C44 115.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.150

#====================================================================
