# Electronic Supplementary Material (ESI) for RSC Advances.
# 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
_database_code_depnum_ccdc_archive 'CCDC 1043442'
_audit_update_record             
;
2015-01-14 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 N2 O5 '
_chemical_formula_sum            'C25 H24 N2 O5 '
_chemical_formula_weight         432.46

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   23.824(3)
_cell_length_b                   10.3816(12)
_cell_length_c                   17.6818(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.662(4)
_cell_angle_gamma                90.00
_cell_volume                     4311.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.79

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.980
_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            32256
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         27.56
_reflns_number_total             4987
_reflns_number_gt                3624
_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)+(0.0606P)²+1.8260P] 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         4972
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.32502(7) 0.50666(17) 0.22828(11) 0.0535(4) Uani 1 1 d . . .
H1 H 0.2936 0.4566 0.2338 0.064 Uiso 1 1 calc R . .
C2 C 0.37398(8) 0.4481(2) 0.21254(12) 0.0692(6) Uani 1 1 d . . .
H2 H 0.3752 0.3590 0.2076 0.083 Uiso 1 1 calc R . .
C3 C 0.42051(8) 0.5206(2) 0.20427(12) 0.0694(6) Uani 1 1 d . . .
H3 H 0.4534 0.4809 0.1940 0.083 Uiso 1 1 calc R . .
C4 C 0.41853(7) 0.6518(2) 0.21119(11) 0.0629(5) Uani 1 1 d . . .
H4 H 0.4500 0.7013 0.2053 0.075 Uiso 1 1 calc R . .
C5 C 0.36969(6) 0.71084(17) 0.22694(10) 0.0483(4) Uani 1 1 d . . .
H5 H 0.3687 0.8000 0.2316 0.058 Uiso 1 1 calc R . .
C6 C 0.32242(6) 0.63886(15) 0.23582(8) 0.0381(3) Uani 1 1 d . . .
C7 C 0.27007(6) 0.70303(16) 0.25598(9) 0.0417(4) Uani 1 1 d . . .
H7A H 0.2635 0.6705 0.3052 0.050 Uiso 1 1 calc R . .
H7B H 0.2771 0.7949 0.2615 0.050 Uiso 1 1 calc R . .
C8 C 0.17824(6) 0.59353(13) 0.20704(8) 0.0326(3) Uani 1 1 d . . .
C9 C 0.13073(5) 0.60089(13) 0.13474(8) 0.0315(3) Uani 1 1 d . . .
C10 C 0.15437(6) 0.70234(13) 0.08741(8) 0.0333(3) Uani 1 1 d . . .
C11 C 0.13555(7) 0.74656(15) 0.01402(9) 0.0418(4) Uani 1 1 d . . .
H11 H 0.1024 0.7141 -0.0149 0.050 Uiso 1 1 calc R . .
C12 C 0.16712(8) 0.84065(16) -0.01588(10) 0.0495(4) Uani 1 1 d . . .
H12 H 0.1547 0.8722 -0.0651 0.059 Uiso 1 1 calc R . .
C13 C 0.21653(8) 0.88741(17) 0.02669(11) 0.0531(4) Uani 1 1 d . . .
H13 H 0.2367 0.9513 0.0059 0.064 Uiso 1 1 calc R . .
C14 C 0.23700(7) 0.84202(16) 0.09937(10) 0.0465(4) Uani 1 1 d . . .
H14 H 0.2706 0.8737 0.1278 0.056 Uiso 1 1 calc R . .
C15 C 0.20558(6) 0.74751(14) 0.12835(8) 0.0345(3) Uani 1 1 d . . .
C16 C 0.04227(6) 0.50627(15) 0.15655(8) 0.0379(3) Uani 1 1 d . . .
H16 H 0.0418 0.4713 0.2079 0.045 Uiso 1 1 calc R . .
C17 C -0.01823(6) 0.54408(17) 0.11910(11) 0.0519(4) Uani 1 1 d . . .
H17A H -0.0246 0.5262 0.0645 0.062 Uiso 1 1 calc R . .
H17B H -0.0465 0.4986 0.1425 0.062 Uiso 1 1 calc R . .
C18 C -0.01994(7) 0.68704(18) 0.13433(11) 0.0526(4) Uani 1 1 d . . .
H18A H -0.0274 0.7042 0.1856 0.063 Uiso 1 1 calc R . .
H18B H -0.0487 0.7294 0.0973 0.063 Uiso 1 1 calc R . .
C19 C 0.03931(7) 0.73039(16) 0.12557(12) 0.0559(5) Uani 1 1 d . . .
H19A H 0.0427 0.7390 0.0719 0.067 Uiso 1 1 calc R . .
H19B H 0.0488 0.8120 0.1512 0.067 Uiso 1 1 calc R . .
C20 C 0.07397(6) 0.41592(14) 0.11193(8) 0.0332(3) Uani 1 1 d . . .
C21 C 0.05297(6) 0.28437(15) 0.09229(9) 0.0404(4) Uani 1 1 d . . .
C22 C 0.07803(12) 0.07342(19) 0.06246(16) 0.0890(8) Uani 1 1 d . . .
H22A H 0.0578 0.0427 0.1015 0.134 Uiso 1 1 calc R . .
H22B H 0.1118 0.0229 0.0629 0.134 Uiso 1 1 calc R . .
H22C H 0.0542 0.0661 0.0132 0.134 Uiso 1 1 calc R . .
C23 C 0.12179(5) 0.46937(13) 0.09752(8) 0.0306(3) Uani 1 1 d . . .
C24 C 0.16548(6) 0.41190(13) 0.05621(8) 0.0324(3) Uani 1 1 d . . .
C25 C 0.18086(8) 0.3242(2) -0.06179(11) 0.0667(6) Uani 1 1 d . . .
H25A H 0.2190 0.3564 -0.0487 0.100 Uiso 1 1 calc R . .
H25B H 0.1672 0.3389 -0.1153 0.100 Uiso 1 1 calc R . .
H25C H 0.1805 0.2336 -0.0513 0.100 Uiso 1 1 calc R . .
N1 N 0.21851(5) 0.68256(12) 0.19921(7) 0.0350(3) Uani 1 1 d . . .
N2 N 0.07609(5) 0.62677(12) 0.16228(7) 0.0369(3) Uani 1 1 d . . .
O1 O 0.17793(5) 0.52223(11) 0.26137(6) 0.0460(3) Uani 1 1 d . . .
O2 O 0.21355(4) 0.39229(12) 0.08573(6) 0.0517(3) Uani 1 1 d . . .
O3 O 0.14453(4) 0.39038(12) -0.01668(6) 0.0489(3) Uani 1 1 d . . .
O4 O 0.00495(5) 0.25150(13) 0.09211(10) 0.0743(4) Uani 1 1 d . . .
O5 O 0.09347(5) 0.20622(11) 0.07708(8) 0.0604(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 C6 1.381(2) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(2) . ?
C7 N1 1.4655(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.2138(17) . ?
C8 N1 1.3559(18) . ?
C8 C9 1.5608(19) . ?
C9 N2 1.4889(17) . ?
C9 C10 1.512(2) . ?
C9 C23 1.5152(19) . ?
C10 C11 1.379(2) . ?
C10 C15 1.3915(19) . ?
C11 C12 1.390(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C15 N1 1.4106(19) . ?
C16 N2 1.4823(19) . ?
C16 C20 1.508(2) . ?
C16 C17 1.533(2) . ?
C16 H16 0.9800 . ?
C17 C18 1.510(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.514(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N2 1.468(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C23 1.3297(19) . ?
C20 C21 1.476(2) . ?
C21 O4 1.1933(18) . ?
C21 O5 1.3224(19) . ?
C22 O5 1.439(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.4927(18) . ?
C24 O2 1.1936(17) . ?
C24 O3 1.3206(18) . ?
C25 O3 1.445(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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 120.57(17) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.34(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.82(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.08(18) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.80(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 118.39(15) . . ?
C1 C6 C7 120.93(14) . . ?
C5 C6 C7 120.64(14) . . ?
N1 C7 C6 113.90(12) . . ?
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 126.51(13) . . ?
O1 C8 C9 125.33(12) . . ?
N1 C8 C9 108.14(11) . . ?
N2 C9 C10 118.86(11) . . ?
N2 C9 C23 103.76(10) . . ?
C10 C9 C23 115.20(11) . . ?
N2 C9 C8 107.13(11) . . ?
C10 C9 C8 101.61(10) . . ?
C23 C9 C8 109.97(11) . . ?
C11 C10 C15 119.72(14) . . ?
C11 C10 C9 131.35(13) . . ?
C15 C10 C9 108.81(12) . . ?
C10 C11 C12 118.74(15) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.53(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.74(16) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 117.31(15) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C10 121.87(14) . . ?
C14 C15 N1 128.09(13) . . ?
C10 C15 N1 110.04(12) . . ?
N2 C16 C20 104.27(11) . . ?
N2 C16 C17 105.92(12) . . ?
C20 C16 C17 116.77(13) . . ?
N2 C16 H16 109.8 . . ?
C20 C16 H16 109.8 . . ?
C17 C16 H16 109.8 . . ?
C18 C17 C16 103.07(13) . . ?
C18 C17 H17A 111.1 . . ?
C16 C17 H17A 111.1 . . ?
C18 C17 H17B 111.1 . . ?
C16 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C17 C18 C19 102.73(13) . . ?
C17 C18 H18A 111.2 . . ?
C19 C18 H18A 111.2 . . ?
C17 C18 H18B 111.2 . . ?
C19 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
N2 C19 C18 103.56(14) . . ?
N2 C19 H19A 111.0 . . ?
C18 C19 H19A 111.0 . . ?
N2 C19 H19B 111.0 . . ?
C18 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C23 C20 C21 127.49(13) . . ?
C23 C20 C16 111.18(12) . . ?
C21 C20 C16 121.27(12) . . ?
O4 C21 O5 123.77(15) . . ?
O4 C21 C20 123.52(15) . . ?
O5 C21 C20 112.68(12) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 C24 128.11(13) . . ?
C20 C23 C9 110.81(12) . . ?
C24 C23 C9 120.93(11) . . ?
O2 C24 O3 125.15(13) . . ?
O2 C24 C23 123.42(13) . . ?
O3 C24 C23 111.39(11) . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8 N1 C15 111.33(11) . . ?
C8 N1 C7 123.71(12) . . ?
C15 N1 C7 124.89(12) . . ?
C19 N2 C16 108.12(11) . . ?
C19 N2 C9 118.51(12) . . ?
C16 N2 C9 108.69(11) . . ?
C24 O3 C25 117.11(13) . . ?
C21 O5 C22 116.82(15) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_1k
_database_code_depnum_ccdc_archive 'CCDC 1043443'
_audit_update_record             
;
2015-01-14 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 Cl N2 O6'
_chemical_formula_sum            'C25 H23 Cl N2 O6'
_chemical_formula_weight         482.90

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                   11.947(2)
_cell_length_b                   15.249(3)
_cell_length_c                   25.716(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4685.1(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9205
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      23.89

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2016
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.956
_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            71450
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         27.54
_reflns_number_total             10765
_reflns_number_gt                8039
_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)+(0.0595P)²+0.3752P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     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(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         10765
_refine_ls_number_parameters     636
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.4188(3) 0.73374(17) 0.36801(10) 0.0677(8) Uani 1 1 d . . .
H1 H 0.4553 0.7816 0.3534 0.081 Uiso 1 1 calc R . .
C2 C 0.3824(4) 0.7376(3) 0.41931(12) 0.0964(13) Uani 1 1 d . . .
H2 H 0.3948 0.7881 0.4387 0.116 Uiso 1 1 calc R . .
C3 C 0.3298(4) 0.6695(4) 0.44111(13) 0.1053(15) Uani 1 1 d . . .
H3 H 0.3062 0.6725 0.4755 0.126 Uiso 1 1 calc R . .
C4 C 0.3110(3) 0.5955(3) 0.41258(15) 0.1075(14) Uani 1 1 d . . .
H4 H 0.2726 0.5486 0.4273 0.129 Uiso 1 1 calc R . .
C5 C 0.3485(3) 0.5899(2) 0.36214(12) 0.0789(9) Uani 1 1 d . . .
H5 H 0.3379 0.5383 0.3436 0.095 Uiso 1 1 calc R . .
C6 C 0.40116(19) 0.65955(15) 0.33878(8) 0.0452(5) Uani 1 1 d . . .
C7 C 0.4439(2) 0.65543(16) 0.28403(8) 0.0492(6) Uani 1 1 d . . .
H7A H 0.5175 0.6821 0.2826 0.059 Uiso 1 1 calc R . .
H7B H 0.4515 0.5945 0.2738 0.059 Uiso 1 1 calc R . .
C8 C 0.38150(16) 0.78619(14) 0.23500(7) 0.0355(4) Uani 1 1 d . . .
C9 C 0.29132(16) 0.81068(13) 0.19357(7) 0.0346(4) Uani 1 1 d . . .
C10 C 0.22522(16) 0.72646(13) 0.18984(7) 0.0350(4) Uani 1 1 d . . .
C11 C 0.12922(17) 0.70561(15) 0.16321(8) 0.0426(5) Uani 1 1 d . . .
H11 H 0.0934 0.7471 0.1426 0.051 Uiso 1 1 calc R . .
C12 C 0.08692(18) 0.62137(16) 0.16781(9) 0.0482(6) Uani 1 1 d . . .
C13 C 0.1383(2) 0.55917(17) 0.19865(10) 0.0600(7) Uani 1 1 d . . .
H13 H 0.1081 0.5031 0.2012 0.072 Uiso 1 1 calc R . .
C14 C 0.2352(2) 0.58022(15) 0.22600(10) 0.0572(6) Uani 1 1 d . . .
H14 H 0.2709 0.5387 0.2467 0.069 Uiso 1 1 calc R . .
C15 C 0.27651(18) 0.66384(13) 0.22166(7) 0.0389(5) Uani 1 1 d . . .
C16 C 0.3676(2) 0.93416(14) 0.14985(8) 0.0439(5) Uani 1 1 d . . .
H16 H 0.441(2) 0.9488(15) 0.1639(9) 0.053 Uiso 1 1 calc . . .
C17 C 0.3577(3) 0.96685(17) 0.09354(9) 0.0603(6) Uani 1 1 d . . .
H17A H 0.2902 1.0013 0.0890 0.072 Uiso 1 1 calc R . .
H17B H 0.4218 1.0026 0.0843 0.072 Uiso 1 1 calc R . .
C18 C 0.3537(2) 0.88523(18) 0.06089(9) 0.0564(6) Uani 1 1 d . . .
H18 H 0.3074 0.8952 0.0300 0.068 Uiso 1 1 calc R . .
C19 C 0.2973(2) 0.82107(16) 0.09644(8) 0.0525(6) Uani 1 1 d . . .
H19A H 0.2177 0.8328 0.0990 0.063 Uiso 1 1 calc R . .
H19B H 0.3084 0.7613 0.0847 0.063 Uiso 1 1 calc R . .
C20 C 0.23065(16) 0.89324(14) 0.21052(8) 0.0374(5) Uani 1 1 d . . .
C21 C 0.14081(18) 0.88754(15) 0.25031(9) 0.0452(5) Uani 1 1 d . . .
C22 C 0.0982(3) 0.8218(2) 0.33123(11) 0.0873(10) Uani 1 1 d . . .
H22A H 0.0835 0.8747 0.3503 0.131 Uiso 1 1 calc R . .
H22B H 0.1288 0.7784 0.3542 0.131 Uiso 1 1 calc R . .
H22C H 0.0296 0.8004 0.3165 0.131 Uiso 1 1 calc R . .
C23 C 0.27726(18) 0.96222(14) 0.18733(8) 0.0415(5) Uani 1 1 d . . .
C24 C 0.2592(2) 1.05814(16) 0.19628(9) 0.0528(6) Uani 1 1 d . . .
C25 C 0.1715(4) 1.16731(19) 0.24506(16) 0.1052(13) Uani 1 1 d . . .
H25A H 0.2056 1.2020 0.2183 0.158 Uiso 1 1 calc R . .
H25B H 0.2046 1.1815 0.2780 0.158 Uiso 1 1 calc R . .
H25C H 0.0927 1.1795 0.2462 0.158 Uiso 1 1 calc R . .
C26 C 0.19117(19) 0.71829(15) 0.88880(9) 0.0461(5) Uani 1 1 d . . .
H26 H 0.1458 0.7525 0.9101 0.055 Uiso 1 1 calc R . .
C27 C 0.1522(2) 0.69189(16) 0.84097(10) 0.0575(6) Uani 1 1 d . . .
H27 H 0.0808 0.7083 0.8303 0.069 Uiso 1 1 calc R . .
C28 C 0.2173(2) 0.64173(17) 0.80905(10) 0.0597(7) Uani 1 1 d . . .
H28 H 0.1904 0.6239 0.7768 0.072 Uiso 1 1 calc R . .
C29 C 0.3228(2) 0.61775(18) 0.82482(10) 0.0638(7) Uani 1 1 d . . .
H29 H 0.3675 0.5838 0.8031 0.077 Uiso 1 1 calc R . .
C30 C 0.3627(2) 0.64391(17) 0.87305(10) 0.0580(6) Uani 1 1 d . . .
H30 H 0.4341 0.6273 0.8836 0.070 Uiso 1 1 calc R . .
C31 C 0.29665(17) 0.69474(13) 0.90557(8) 0.0400(5) Uani 1 1 d . . .
C32 C 0.3391(2) 0.72578(15) 0.95763(9) 0.0491(6) Uani 1 1 d . . .
H32A H 0.3982 0.7683 0.9521 0.059 Uiso 1 1 calc R . .
H32B H 0.2787 0.7550 0.9759 0.059 Uiso 1 1 calc R . .
C33 C 0.49299(18) 0.63747(14) 0.99750(8) 0.0396(5) Uani 1 1 d . . .
C34 C 0.50247(16) 0.55711(13) 1.03478(8) 0.0339(4) Uani 1 1 d . . .
C35 C 0.38063(16) 0.53059(14) 1.04070(8) 0.0369(5) Uani 1 1 d . . .
C36 C 0.33313(18) 0.45947(15) 1.06519(8) 0.0450(5) Uani 1 1 d . . .
H36 H 0.3768 0.4174 1.0817 0.054 Uiso 1 1 calc R . .
C37 C 0.2162(2) 0.45331(18) 1.06413(10) 0.0553(6) Uani 1 1 d . . .
C38 C 0.1511(2) 0.5141(2) 1.03956(10) 0.0617(7) Uani 1 1 d . . .
H38 H 0.0736 0.5079 1.0398 0.074 Uiso 1 1 calc R . .
C39 C 0.19874(19) 0.58455(19) 1.01439(10) 0.0551(6) Uani 1 1 d . . .
H39 H 0.1547 0.6262 0.9977 0.066 Uiso 1 1 calc R . .
C40 C 0.31417(17) 0.59138(15) 1.01462(8) 0.0393(5) Uani 1 1 d . . .
C41 C 0.67266(18) 0.54262(15) 1.08536(8) 0.0419(5) Uani 1 1 d . . .
H41 H 0.734(2) 0.5852(15) 1.0820(9) 0.050 Uiso 1 1 calc . . .
C42 C 0.6764(2) 0.49938(19) 1.13917(9) 0.0584(6) Uani 1 1 d . . .
H42A H 0.7042 0.4398 1.1368 0.070 Uiso 1 1 calc R . .
H42B H 0.7241 0.5323 1.1626 0.070 Uiso 1 1 calc R . .
C43 C 0.5555(2) 0.50038(14) 1.15792(8) 0.0467(5) Uani 1 1 d . . .
H43 H 0.5161 0.4485 1.1448 0.056 Uiso 1 1 calc R . .
C44 C 0.50813(19) 0.58181(14) 1.13291(8) 0.0429(5) Uani 1 1 d . . .
H44A H 0.4276 0.5769 1.1291 0.051 Uiso 1 1 calc R . .
H44B H 0.5248 0.6332 1.1538 0.051 Uiso 1 1 calc R . .
C45 C 0.57843(16) 0.48732(13) 1.01265(7) 0.0345(4) Uani 1 1 d . . .
C46 C 0.5419(2) 0.43371(19) 0.96656(9) 0.0518(6) Uani 1 1 d . A .
C47 C 0.5099(4) 0.4251(3) 0.87748(14) 0.0776(14) Uani 0.740(6) 1 d P A 1
H47A H 0.5519 0.3716 0.8749 0.116 Uiso 0.740(6) 1 calc PR A 1
H47B H 0.5200 0.4590 0.8464 0.116 Uiso 0.740(6) 1 calc PR A 1
H47C H 0.4320 0.4117 0.8818 0.116 Uiso 0.740(6) 1 calc PR A 1
C48 C 0.67301(17) 0.48130(13) 1.03976(8) 0.0370(5) Uani 1 1 d . . .
C49 C 0.77397(19) 0.42815(16) 1.02870(9) 0.0475(5) Uani 1 1 d . . .
C50 C 0.8556(3) 0.3215(2) 0.97393(13) 0.0786(9) Uani 1 1 d . . .
H50A H 0.9201 0.3582 0.9695 0.118 Uiso 1 1 calc R . .
H50B H 0.8398 0.2914 0.9419 0.118 Uiso 1 1 calc R . .
H50C H 0.8699 0.2793 1.0008 0.118 Uiso 1 1 calc R . .
C47' C 0.4888(14) 0.3270(9) 0.9192(5) 0.103(6) Uani 0.260(6) 1 d P A 2
H47D H 0.4316 0.3603 0.9020 0.154 Uiso 0.260(6) 1 calc PR A 2
H47E H 0.4664 0.2666 0.9211 0.154 Uiso 0.260(6) 1 calc PR A 2
H47F H 0.5575 0.3315 0.9000 0.154 Uiso 0.260(6) 1 calc PR A 2
Cl1 Cl -0.03401(6) 0.59286(5) 0.13394(3) 0.0716(2) Uani 1 1 d . . .
Cl2 Cl 0.15481(7) 0.36383(6) 1.09482(4) 0.0935(3) Uani 1 1 d . . .
N1 N 0.36999(14) 0.70024(12) 0.24680(6) 0.0392(4) Uani 1 1 d . . .
N2 N 0.35429(14) 0.83689(11) 0.14653(6) 0.0370(4) Uani 1 1 d . . .
N3 N 0.38193(14) 0.65465(12) 0.99006(7) 0.0420(4) Uani 1 1 d . . .
N4 N 0.56239(14) 0.58817(11) 1.08172(6) 0.0381(4) Uani 1 1 d . . .
O1 O 0.45312(12) 0.83523(10) 0.25224(5) 0.0457(4) Uani 1 1 d . . .
O2 O 0.46247(17) 0.85640(16) 0.04579(7) 0.0773(6) Uani 1 1 d . . .
H2A H 0.5001 0.8466 0.0718 0.116 Uiso 1 1 calc R . .
O3 O 0.04859(15) 0.91768(14) 0.24673(8) 0.0762(6) Uani 1 1 d . . .
O4 O 0.17750(13) 0.84002(12) 0.28995(6) 0.0562(4) Uani 1 1 d . . .
O5 O 0.3070(2) 1.11237(12) 0.17127(9) 0.0843(6) Uani 1 1 d . . .
O6 O 0.1888(2) 1.07501(11) 0.23397(8) 0.0741(5) Uani 1 1 d . . .
O7 O 0.57079(14) 0.67857(11) 0.97981(7) 0.0551(4) Uani 1 1 d . . .
O8 O 0.54389(19) 0.50510(11) 1.21265(6) 0.0653(5) Uani 1 1 d . . .
H8 H 0.5457 0.4555 1.2249 0.098 Uiso 1 1 calc R . .
O9 O 0.5053(2) 0.36097(14) 0.97125(8) 0.0789(6) Uani 1 1 d . . .
O10 O 0.54996(18) 0.47626(13) 0.92301(6) 0.0683(5) Uani 1 1 d . . .
O11 O 0.85890(15) 0.43486(17) 1.05262(9) 0.0872(7) Uani 1 1 d . . .
O12 O 0.76021(14) 0.37501(11) 0.98833(7) 0.0560(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 1.374(4) . ?
C1 C2 1.390(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.337(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.499(3) . ?
C7 N1 1.471(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.220(2) . ?
C8 N1 1.352(3) . ?
C8 C9 1.560(3) . ?
C9 N2 1.480(2) . ?
C9 C10 1.511(3) . ?
C9 C20 1.517(3) . ?
C10 C11 1.373(3) . ?
C10 C15 1.399(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(4) . ?
C12 Cl1 1.742(2) . ?
C13 C14 1.392(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.405(3) . ?
C16 N2 1.494(3) . ?
C16 C23 1.509(3) . ?
C16 C17 1.536(3) . ?
C16 H16 0.98(3) . ?
C17 C18 1.502(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O2 1.426(3) . ?
C18 C19 1.499(3) . ?
C18 H18 0.9800 . ?
C19 N2 1.477(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C23 1.331(3) . ?
C20 C21 1.486(3) . ?
C21 O3 1.197(3) . ?
C21 O4 1.325(3) . ?
C22 O4 1.450(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.496(3) . ?
C24 O5 1.194(3) . ?
C24 O6 1.309(3) . ?
C25 O6 1.451(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.376(3) . ?
C26 C31 1.380(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.366(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.373(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.388(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.387(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.508(3) . ?
C32 N3 1.461(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 O7 1.210(3) . ?
C33 N3 1.366(3) . ?
C33 C34 1.560(3) . ?
C34 N4 1.481(3) . ?
C34 C45 1.510(3) . ?
C34 C35 1.519(3) . ?
C35 C36 1.376(3) . ?
C35 C40 1.393(3) . ?
C36 C37 1.400(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.366(4) . ?
C37 Cl2 1.739(3) . ?
C38 C39 1.377(4) . ?
C38 H38 0.9300 . ?
C39 C40 1.383(3) . ?
C39 H39 0.9300 . ?
C40 N3 1.409(3) . ?
C41 N4 1.492(3) . ?
C41 C48 1.500(3) . ?
C41 C42 1.533(3) . ?
C41 H41 0.98(3) . ?
C42 C43 1.523(4) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 O8 1.416(3) . ?
C43 C44 1.508(3) . ?
C43 H43 0.9800 . ?
C44 N4 1.471(3) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C48 1.331(3) . ?
C45 C46 1.505(3) . ?
C46 O9 1.198(3) . ?
C46 O10 1.298(3) . ?
C47 O10 1.486(4) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 C49 1.481(3) . ?
C49 O11 1.191(3) . ?
C49 O12 1.327(3) . ?
C50 O12 1.450(3) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C47' O9 1.449(12) . ?
C47' H47D 0.9600 . ?
C47' H47E 0.9600 . ?
C47' H47F 0.9600 . ?
O2 H2A 0.8200 . ?
O8 H8 0.8200 . ?

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(3) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 117.9(2) . . ?
C5 C6 C7 122.3(2) . . ?
C1 C6 C7 119.7(2) . . ?
N1 C7 C6 112.82(17) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 N1 125.72(19) . . ?
O1 C8 C9 125.86(19) . . ?
N1 C8 C9 108.35(16) . . ?
N2 C9 C10 116.33(16) . . ?
N2 C9 C20 104.70(16) . . ?
C10 C9 C20 118.30(16) . . ?
N2 C9 C8 105.77(14) . . ?
C10 C9 C8 101.59(16) . . ?
C20 C9 C8 109.42(15) . . ?
C11 C10 C15 119.97(19) . . ?
C11 C10 C9 131.69(19) . . ?
C15 C10 C9 108.31(17) . . ?
C10 C11 C12 118.5(2) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 Cl1 118.96(18) . . ?
C11 C12 Cl1 119.42(19) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 118.2(2) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C10 121.6(2) . . ?
C14 C15 N1 128.0(2) . . ?
C10 C15 N1 110.34(18) . . ?
N2 C16 C23 103.99(17) . . ?
N2 C16 C17 105.07(17) . . ?
C23 C16 C17 117.1(2) . . ?
N2 C16 H16 110.1(14) . . ?
C23 C16 H16 110.1(14) . . ?
C17 C16 H16 110.1(14) . . ?
C18 C17 C16 105.11(19) . . ?
C18 C17 H17A 110.7 . . ?
C16 C17 H17A 110.7 . . ?
C18 C17 H17B 110.7 . . ?
C16 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
O2 C18 C19 112.0(2) . . ?
O2 C18 C17 112.2(2) . . ?
C19 C18 C17 102.38(19) . . ?
O2 C18 H18 110.0 . . ?
C19 C18 H18 110.0 . . ?
C17 C18 H18 110.0 . . ?
N2 C19 C18 102.60(18) . . ?
N2 C19 H19A 111.2 . . ?
C18 C19 H19A 111.2 . . ?
N2 C19 H19B 111.2 . . ?
C18 C19 H19B 111.2 . . ?
H19A C19 H19B 109.2 . . ?
C23 C20 C21 131.1(2) . . ?
C23 C20 C9 109.10(17) . . ?
C21 C20 C9 119.65(18) . . ?
O3 C21 O4 125.0(2) . . ?
O3 C21 C20 126.1(2) . . ?
O4 C21 C20 108.83(18) . . ?
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 . . ?
C20 C23 C24 130.0(2) . . ?
C20 C23 C16 111.18(19) . . ?
C24 C23 C16 118.6(2) . . ?
O5 C24 O6 124.8(2) . . ?
O5 C24 C23 121.7(2) . . ?
O6 C24 C23 113.5(2) . . ?
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 . . ?
C27 C26 C31 120.9(2) . . ?
C27 C26 H26 119.6 . . ?
C31 C26 H26 119.6 . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 119.6(2) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C28 C29 C30 120.2(2) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 120.3(2) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C26 C31 C30 118.5(2) . . ?
C26 C31 C32 120.2(2) . . ?
C30 C31 C32 121.30(19) . . ?
N3 C32 C31 113.05(18) . . ?
N3 C32 H32A 109.0 . . ?
C31 C32 H32A 109.0 . . ?
N3 C32 H32B 109.0 . . ?
C31 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
O7 C33 N3 126.46(19) . . ?
O7 C33 C34 125.60(18) . . ?
N3 C33 C34 107.90(17) . . ?
N4 C34 C45 104.00(15) . . ?
N4 C34 C35 117.83(16) . . ?
C45 C34 C35 115.23(17) . . ?
N4 C34 C33 106.54(15) . . ?
C45 C34 C33 111.45(16) . . ?
C35 C34 C33 101.61(16) . . ?
C36 C35 C40 120.64(19) . . ?
C36 C35 C34 130.61(19) . . ?
C40 C35 C34 108.72(18) . . ?
C35 C36 C37 117.1(2) . . ?
C35 C36 H36 121.5 . . ?
C37 C36 H36 121.5 . . ?
C38 C37 C36 122.1(2) . . ?
C38 C37 Cl2 120.18(19) . . ?
C36 C37 Cl2 117.7(2) . . ?
C37 C38 C39 120.8(2) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C38 C39 C40 118.0(2) . . ?
C38 C39 H39 121.0 . . ?
C40 C39 H39 121.0 . . ?
C39 C40 C35 121.4(2) . . ?
C39 C40 N3 128.5(2) . . ?
C35 C40 N3 110.12(17) . . ?
N4 C41 C48 104.10(16) . . ?
N4 C41 C42 106.40(18) . . ?
C48 C41 C42 115.94(19) . . ?
N4 C41 H41 110.0(14) . . ?
C48 C41 H41 110.0(14) . . ?
C42 C41 H41 110.0(14) . . ?
C43 C42 C41 104.72(18) . . ?
C43 C42 H42A 110.8 . . ?
C41 C42 H42A 110.8 . . ?
C43 C42 H42B 110.8 . . ?
C41 C42 H42B 110.8 . . ?
H42A C42 H42B 108.9 . . ?
O8 C43 C44 110.20(17) . . ?
O8 C43 C42 114.1(2) . . ?
C44 C43 C42 103.22(19) . . ?
O8 C43 H43 109.7 . . ?
C44 C43 H43 109.7 . . ?
C42 C43 H43 109.7 . . ?
N4 C44 C43 105.71(17) . . ?
N4 C44 H44A 110.6 . . ?
C43 C44 H44A 110.6 . . ?
N4 C44 H44B 110.6 . . ?
C43 C44 H44B 110.6 . . ?
H44A C44 H44B 108.7 . . ?
C48 C45 C46 128.41(19) . . ?
C48 C45 C34 111.20(18) . . ?
C46 C45 C34 120.37(17) . . ?
O9 C46 O10 125.2(2) . . ?
O9 C46 C45 122.0(2) . . ?
O10 C46 C45 112.7(2) . . ?
O10 C47 H47A 109.5 . . ?
O10 C47 H47B 109.5 . . ?
O10 C47 H47C 109.5 . . ?
C45 C48 C49 129.0(2) . . ?
C45 C48 C41 111.35(18) . . ?
C49 C48 C41 119.58(19) . . ?
O11 C49 O12 124.2(2) . . ?
O11 C49 C48 123.2(2) . . ?
O12 C49 C48 112.55(19) . . ?
O12 C50 H50A 109.5 . . ?
O12 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
O12 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
O9 C47' H47D 109.5 . . ?
O9 C47' H47E 109.5 . . ?
H47D C47' H47E 109.5 . . ?
O9 C47' H47F 109.5 . . ?
H47D C47' H47F 109.5 . . ?
H47E C47' H47F 109.5 . . ?
C8 N1 C15 111.14(16) . . ?
C8 N1 C7 122.37(18) . . ?
C15 N1 C7 126.38(18) . . ?
C19 N2 C9 115.77(15) . . ?
C19 N2 C16 105.14(17) . . ?
C9 N2 C16 105.99(15) . . ?
C33 N3 C40 111.35(17) . . ?
C33 N3 C32 124.24(19) . . ?
C40 N3 C32 124.27(18) . . ?
C44 N4 C34 119.69(16) . . ?
C44 N4 C41 107.59(15) . . ?
C34 N4 C41 109.21(15) . . ?
C18 O2 H2A 109.5 . . ?
C21 O4 C22 116.8(2) . . ?
C24 O6 C25 115.3(2) . . ?
C43 O8 H8 109.5 . . ?
C46 O9 C47' 106.7(6) . . ?
C46 O10 C47 113.2(3) . . ?
C49 O12 C50 116.5(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8 O1 0.82 1.93 2.744(2) 175.0 3_646

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_1m
_database_code_depnum_ccdc_archive 'CCDC 1043444'
_audit_update_record             
;
2015-01-14 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 Cl N2 O5 S'
_chemical_formula_sum            'C24 H21 Cl N2 O5 S'
_chemical_formula_weight         484.94

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           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                   9.4108(10)
_cell_length_b                   10.1366(12)
_cell_length_c                   13.4852(14)
_cell_angle_alpha                70.823(3)
_cell_angle_beta                 77.865(3)
_cell_angle_gamma                73.128(3)
_cell_volume                     1153.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8393
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.954
_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            17348
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         27.56
_reflns_number_total             5264
_reflns_number_gt                3891
_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)+(0.0520P)²+0.4612P] 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         5264
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.6972(3) -0.3102(2) 0.16043(18) 0.0549(5) Uani 1 1 d . . .
H1 H 0.7578 -0.3309 0.1008 0.066 Uiso 1 1 calc R . .
C2 C 0.5536(3) -0.3286(3) 0.1826(3) 0.0768(8) Uani 1 1 d . . .
H2 H 0.5188 -0.3636 0.1389 0.092 Uiso 1 1 calc R . .
C3 C 0.4630(4) -0.2959(3) 0.2674(3) 0.0905(10) Uani 1 1 d . . .
H3 H 0.3649 -0.3058 0.2810 0.109 Uiso 1 1 calc R . .
C4 C 0.5151(4) -0.2483(3) 0.3335(3) 0.0895(10) Uani 1 1 d . . .
H4 H 0.4529 -0.2277 0.3926 0.107 Uiso 1 1 calc R . .
C5 C 0.6604(3) -0.2306(3) 0.31277(19) 0.0650(6) Uani 1 1 d . . .
H5 H 0.6951 -0.1978 0.3578 0.078 Uiso 1 1 calc R . .
C6 C 0.7531(2) -0.26156(19) 0.22531(15) 0.0424(4) Uani 1 1 d . . .
C7 C 0.9114(2) -0.2458(2) 0.20162(18) 0.0474(5) Uani 1 1 d . . .
H7A H 0.9716 -0.3242 0.2507 0.057 Uiso 1 1 calc R . .
H7B H 0.9515 -0.2529 0.1307 0.057 Uiso 1 1 calc R . .
C8 C 0.86964(19) 0.0248(2) 0.13978(14) 0.0359(4) Uani 1 1 d . . .
C9 C 0.8160(2) 0.0528(2) 0.04528(14) 0.0434(5) Uani 1 1 d . . .
H9 H 0.8063 -0.0212 0.0227 0.052 Uiso 1 1 calc R . .
C10 C 0.7776(2) 0.1942(2) -0.01423(15) 0.0498(5) Uani 1 1 d . . .
H10 H 0.7410 0.2167 -0.0782 0.060 Uiso 1 1 calc R . .
C11 C 0.7928(2) 0.3026(2) 0.02008(15) 0.0497(5) Uani 1 1 d . . .
C12 C 0.8461(2) 0.2748(2) 0.11574(14) 0.0438(4) Uani 1 1 d . . .
H12 H 0.8559 0.3489 0.1382 0.053 Uiso 1 1 calc R . .
C13 C 0.88335(19) 0.13434(19) 0.17523(13) 0.0353(4) Uani 1 1 d . . .
C14 C 0.9477(2) 0.06693(18) 0.28013(13) 0.0332(4) Uani 1 1 d . . .
C15 C 0.9818(2) -0.09639(19) 0.28944(14) 0.0385(4) Uani 1 1 d . . .
N2 N 0.85065(16) 0.08749(15) 0.37713(11) 0.0343(3) Uani 1 1 d . . .
C18 C 0.6909(2) 0.1219(2) 0.38085(16) 0.0434(4) Uani 1 1 d . . .
H18A H 0.6463 0.0737 0.4501 0.052 Uiso 1 1 calc R . .
H18B H 0.6644 0.0901 0.3282 0.052 Uiso 1 1 calc R . .
C17 C 0.7894(2) 0.3385(2) 0.3826(2) 0.0585(6) Uani 1 1 d . . .
H17A H 0.8359 0.4001 0.3207 0.070 Uiso 1 1 calc R . .
H17B H 0.7667 0.3824 0.4399 0.070 Uiso 1 1 calc R . .
C19 C 1.08158(19) 0.11691(18) 0.28506(13) 0.0339(4) Uani 1 1 d . . .
C20 C 1.2165(2) 0.0949(2) 0.20830(15) 0.0421(4) Uani 1 1 d . . .
C21 C 1.4518(3) 0.1454(3) 0.1397(2) 0.0717(7) Uani 1 1 d . . .
H21A H 1.5044 0.0462 0.1618 0.108 Uiso 1 1 calc R . .
H21B H 1.5118 0.2050 0.1442 0.108 Uiso 1 1 calc R . .
H21C H 1.4325 0.1698 0.0679 0.108 Uiso 1 1 calc R . .
C22 C 1.0537(2) 0.18116(17) 0.36126(13) 0.0337(4) Uani 1 1 d . . .
C23 C 1.1582(2) 0.24150(19) 0.39388(14) 0.0381(4) Uani 1 1 d . . .
C24 C 1.1910(3) 0.4490(3) 0.4180(3) 0.0925(11) Uani 1 1 d . . .
H24A H 1.2067 0.3987 0.4903 0.139 Uiso 1 1 calc R . .
H24B H 1.1385 0.5472 0.4127 0.139 Uiso 1 1 calc R . .
H24C H 1.2859 0.4465 0.3743 0.139 Uiso 1 1 calc R . .
Cl1 Cl 0.74871(10) 0.47946(7) -0.05953(5) 0.0864(3) Uani 1 1 d . . .
N1 N 0.92342(17) -0.10954(16) 0.20961(12) 0.0396(4) Uani 1 1 d . . .
C16 C 0.8966(2) 0.18711(19) 0.41490(14) 0.0373(4) Uani 1 1 d . . .
H16 H 0.8954 0.1523 0.4919 0.045 Uiso 1 1 calc R . .
O1 O 1.04213(18) -0.19408(14) 0.35809(12) 0.0560(4) Uani 1 1 d . . .
O2 O 1.23367(18) 0.0194(2) 0.15238(13) 0.0698(5) Uani 1 1 d . . .
O3 O 1.31239(17) 0.16831(17) 0.20731(12) 0.0581(4) Uani 1 1 d . . .
O4 O 1.27212(17) 0.17392(16) 0.42858(13) 0.0598(4) Uani 1 1 d . . .
O5 O 1.10269(17) 0.38037(15) 0.38287(14) 0.0592(4) Uani 1 1 d . . .
S1 S 0.62187(7) 0.31696(6) 0.35413(5) 0.05974(18) 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 1.375(3) . ?
C1 C6 1.384(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.349(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(3) . ?
C7 N1 1.458(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.381(2) . ?
C8 C13 1.391(2) . ?
C8 N1 1.398(2) . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(3) . ?
C11 Cl1 1.740(2) . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.523(2) . ?
C14 N2 1.468(2) . ?
C14 C19 1.509(2) . ?
C14 C15 1.559(2) . ?
C15 O1 1.205(2) . ?
C15 N1 1.366(2) . ?
N2 C18 1.435(2) . ?
N2 C16 1.466(2) . ?
C18 S1 1.829(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 C16 1.552(3) . ?
C17 S1 1.786(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C22 1.333(2) . ?
C19 C20 1.473(3) . ?
C20 O2 1.199(2) . ?
C20 O3 1.321(2) . ?
C21 O3 1.438(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C16 1.497(3) . ?
C22 C23 1.497(2) . ?
C23 O4 1.188(2) . ?
C23 O5 1.321(2) . ?
C24 O5 1.455(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C16 H16 0.9800 . ?

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 121.2(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 121.26(19) . . ?
C1 C6 C7 120.52(19) . . ?
N1 C7 C6 112.70(16) . . ?
N1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C13 121.96(18) . . ?
C9 C8 N1 127.56(17) . . ?
C13 C8 N1 110.41(14) . . ?
C10 C9 C8 117.53(18) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 120.63(17) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 121.99(19) . . ?
C10 C11 Cl1 119.19(15) . . ?
C12 C11 Cl1 118.80(17) . . ?
C13 C12 C11 117.37(18) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C12 C13 C8 120.52(16) . . ?
C12 C13 C14 130.91(16) . . ?
C8 C13 C14 108.53(15) . . ?
N2 C14 C19 102.00(13) . . ?
N2 C14 C13 118.61(14) . . ?
C19 C14 C13 114.52(14) . . ?
N2 C14 C15 106.61(14) . . ?
C19 C14 C15 114.12(14) . . ?
C13 C14 C15 101.24(13) . . ?
O1 C15 N1 125.96(17) . . ?
O1 C15 C14 126.07(15) . . ?
N1 C15 C14 107.87(14) . . ?
C18 N2 C16 110.89(14) . . ?
C18 N2 C14 120.15(14) . . ?
C16 N2 C14 109.83(13) . . ?
N2 C18 S1 108.16(13) . . ?
N2 C18 H18A 110.1 . . ?
S1 C18 H18A 110.1 . . ?
N2 C18 H18B 110.1 . . ?
S1 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C16 C17 S1 107.78(14) . . ?
C16 C17 H17A 110.2 . . ?
S1 C17 H17A 110.2 . . ?
C16 C17 H17B 110.2 . . ?
S1 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C22 C19 C20 129.57(17) . . ?
C22 C19 C14 111.02(15) . . ?
C20 C19 C14 119.37(15) . . ?
O2 C20 O3 124.81(19) . . ?
O2 C20 C19 122.28(19) . . ?
O3 C20 C19 112.90(16) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 C16 110.60(15) . . ?
C19 C22 C23 127.71(17) . . ?
C16 C22 C23 121.69(15) . . ?
O4 C23 O5 124.41(17) . . ?
O4 C23 C22 125.25(17) . . ?
O5 C23 C22 110.28(15) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 N1 C8 111.37(14) . . ?
C15 N1 C7 124.17(16) . . ?
C8 N1 C7 124.39(15) . . ?
N2 C16 C22 102.59(13) . . ?
N2 C16 C17 109.36(15) . . ?
C22 C16 C17 113.61(16) . . ?
N2 C16 H16 110.3 . . ?
C22 C16 H16 110.3 . . ?
C17 C16 H16 110.3 . . ?
C20 O3 C21 116.50(18) . . ?
C23 O5 C24 115.14(16) . . ?
C17 S1 C18 93.24(9) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 1043445'
_audit_update_record             
;
2015-01-14 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H32 N2 O9'
_chemical_formula_sum            'C32 H32 N2 O9'
_chemical_formula_weight         588.60

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           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                   10.0841(17)
_cell_length_b                   11.1503(19)
_cell_length_c                   14.319(3)
_cell_angle_alpha                111.322(2)
_cell_angle_beta                 104.083(2)
_cell_angle_gamma                90.975(2)
_cell_volume                     1444.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5124
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.77

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10603
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5079
_reflns_number_gt                4241
_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)+(0.0731P)²+0.2578P] 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         5045
_refine_ls_number_parameters     405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1238
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 1.1701(2) 0.3290(2) 0.22719(16) 0.0615(5) Uani 1 1 d . . .
H1 H 1.1240 0.3881 0.2033 0.074 Uiso 1 1 calc R . .
C2 C 1.2602(3) 0.2581(3) 0.17593(19) 0.0755(7) Uani 1 1 d . . .
H2 H 1.2737 0.2695 0.1176 0.091 Uiso 1 1 calc R . .
C3 C 1.3298(2) 0.1711(2) 0.2105(2) 0.0765(7) Uani 1 1 d . . .
H3 H 1.3901 0.1235 0.1758 0.092 Uiso 1 1 calc R . .
C4 C 1.3096(2) 0.1551(2) 0.2971(2) 0.0717(6) Uani 1 1 d . . .
H4 H 1.3572 0.0967 0.3212 0.086 Uiso 1 1 calc R . .
C5 C 1.2195(2) 0.22469(19) 0.34845(16) 0.0561(5) Uani 1 1 d . . .
H5 H 1.2064 0.2127 0.4067 0.067 Uiso 1 1 calc R . .
C6 C 1.14805(17) 0.31261(16) 0.31381(13) 0.0428(4) Uani 1 1 d . . .
C7 C 1.05200(19) 0.38810(19) 0.37316(14) 0.0480(4) Uani 1 1 d . . .
H7A H 1.0078 0.3325 0.3981 0.058 Uiso 1 1 calc R . .
H7B H 1.1059 0.4603 0.4335 0.058 Uiso 1 1 calc R . .
C8 C 0.92837(16) 0.56689(15) 0.34202(12) 0.0357(4) Uani 1 1 d . . .
C9 C 0.79417(15) 0.58048(14) 0.26515(11) 0.0320(3) Uani 1 1 d . . .
C10 C 0.74202(15) 0.43836(14) 0.19786(11) 0.0324(3) Uani 1 1 d . . .
C11 C 0.62824(16) 0.38313(15) 0.11464(13) 0.0385(4) Uani 1 1 d . . .
H11 H 0.5649 0.4350 0.0950 0.046 Uiso 1 1 calc R . .
C12 C 0.60769(18) 0.24856(16) 0.05937(14) 0.0456(4) Uani 1 1 d . . .
C13 C 0.4880(2) 0.1879(2) -0.03631(18) 0.0698(6) Uani 1 1 d . . .
H13A H 0.5057 0.2067 -0.0927 0.105 Uiso 1 1 calc R . .
H13B H 0.4055 0.2227 -0.0218 0.105 Uiso 1 1 calc R . .
H13C H 0.4768 0.0957 -0.0551 0.105 Uiso 1 1 calc R . .
C14 C 0.7019(2) 0.17377(16) 0.09301(15) 0.0485(4) Uani 1 1 d . . .
H14 H 0.6875 0.0843 0.0577 0.058 Uiso 1 1 calc R . .
C15 C 0.81690(19) 0.22751(15) 0.17756(14) 0.0444(4) Uani 1 1 d . . .
H15 H 0.8787 0.1757 0.1990 0.053 Uiso 1 1 calc R . .
C16 C 0.83605(16) 0.36075(14) 0.22853(12) 0.0349(3) Uani 1 1 d . . .
C17 C 0.83691(15) 0.64639(14) 0.19687(11) 0.0327(3) Uani 1 1 d . . .
C18 C 0.84829(16) 0.55245(14) 0.09325(12) 0.0342(3) Uani 1 1 d . . .
C19 C 0.7409(2) 0.4611(2) -0.08759(13) 0.0569(5) Uani 1 1 d . . .
H19A H 0.8296 0.4584 -0.1012 0.085 Uiso 1 1 calc R . .
H19B H 0.6763 0.4810 -0.1398 0.085 Uiso 1 1 calc R . .
H19C H 0.7102 0.3783 -0.0890 0.085 Uiso 1 1 calc R . .
C20 C 0.86846(16) 0.77405(14) 0.22573(12) 0.0359(4) Uani 1 1 d . . .
C21 C 0.90383(17) 0.83002(15) 0.15304(12) 0.0388(4) Uani 1 1 d . . .
C22 C 1.0601(3) 0.8362(2) 0.0552(2) 0.0742(7) Uani 1 1 d . . .
H22A H 0.9846 0.8297 -0.0028 0.111 Uiso 1 1 calc R . .
H22B H 1.1308 0.7880 0.0304 0.111 Uiso 1 1 calc R . .
H22C H 1.0964 0.9256 0.0940 0.111 Uiso 1 1 calc R . .
C23 C 0.85943(18) 0.86692(15) 0.33091(13) 0.0434(4) Uani 1 1 d . B .
H23 H 0.9081 0.8347 0.3835 0.052 Uiso 1 1 calc R . .
C24 C 0.9147(3) 1.01029(17) 0.36600(16) 0.0637(6) Uani 1 1 d . . .
H24A H 1.0038 1.0296 0.4165 0.076 Uiso 0.54(3) 1 calc PR A 1
H24B H 0.9251 1.0288 0.3068 0.076 Uiso 0.54(3) 1 calc PR A 1
H24C H 0.9712 1.0220 0.3233 0.076 Uiso 0.46(3) 1 calc PR A 2
H24D H 0.9675 1.0455 0.4384 0.076 Uiso 0.46(3) 1 calc PR A 2
C25 C 0.8194(7) 1.0862(6) 0.4108(10) 0.069(2) Uani 0.502(19) 1 d P B 1
H25A H 0.8191 1.1672 0.4001 0.083 Uiso 0.502(19) 1 calc PR B 1
H25B H 0.8416 1.1052 0.4850 0.083 Uiso 0.502(19) 1 calc PR B 1
C25' C 0.7730(16) 1.0756(8) 0.3487(15) 0.092(4) Uani 0.498(19) 1 d P B 2
H25C H 0.7827 1.1611 0.4028 0.110 Uiso 0.498(19) 1 calc PR B 2
H25D H 0.7516 1.0846 0.2819 0.110 Uiso 0.498(19) 1 calc PR B 2
C26 C 0.6722(3) 0.99886(19) 0.35191(19) 0.0712(6) Uani 1 1 d . . .
H26A H 0.6093 1.0183 0.3957 0.085 Uiso 0.54(3) 1 calc PR A 1
H26B H 0.6300 1.0092 0.2872 0.085 Uiso 0.54(3) 1 calc PR A 1
H26C H 0.5888 0.9937 0.2990 0.085 Uiso 0.46(3) 1 calc PR A 2
H26D H 0.6530 1.0343 0.4193 0.085 Uiso 0.46(3) 1 calc PR A 2
C27 C 0.64682(18) 0.76774(16) 0.33888(12) 0.0412(4) Uani 1 1 d . . .
C28 C 0.52207(19) 0.80293(17) 0.38034(13) 0.0467(4) Uani 1 1 d . B .
C29 C 0.2834(2) 0.8077(3) 0.3365(2) 0.0915(9) Uani 1 1 d . B .
H29A H 0.2663 0.7464 0.3662 0.137 Uiso 1 1 calc R . .
H29B H 0.2078 0.7973 0.2774 0.137 Uiso 1 1 calc R . .
H29C H 0.2927 0.8941 0.3875 0.137 Uiso 1 1 calc R . .
C30 C 0.68470(16) 0.64524(15) 0.31963(12) 0.0362(4) Uani 1 1 d . B .
C31 C 0.60989(18) 0.56435(16) 0.35639(14) 0.0446(4) Uani 1 1 d . . .
C32 C 0.6299(3) 0.4018(2) 0.4279(2) 0.0779(7) Uani 1 1 d . . .
H32A H 0.5973 0.4506 0.4867 0.117 Uiso 1 1 calc R B .
H32B H 0.6967 0.3488 0.4473 0.117 Uiso 1 1 calc R . .
H32C H 0.5540 0.3476 0.3724 0.117 Uiso 1 1 calc R . .
N1 N 0.94545(14) 0.43840(13) 0.31265(10) 0.0376(3) Uani 1 1 d . . .
N2 N 0.71557(17) 0.86971(13) 0.33386(12) 0.0482(4) Uani 1 1 d . B .
O1 O 1.00496(13) 0.65506(12) 0.41412(9) 0.0484(3) Uani 1 1 d . . .
O2 O 0.93239(12) 0.47690(11) 0.08399(9) 0.0457(3) Uani 1 1 d . . .
O3 O 0.75058(12) 0.56073(11) 0.01478(8) 0.0439(3) Uani 1 1 d . . .
O4 O 0.84286(15) 0.91057(14) 0.12878(12) 0.0621(4) Uani 1 1 d . . .
O5 O 1.01220(14) 0.78388(13) 0.12202(10) 0.0537(3) Uani 1 1 d . . .
O6 O 0.52788(15) 0.84856(15) 0.47108(10) 0.0652(4) Uani 1 1 d . . .
O7 O 0.40925(14) 0.78576(15) 0.30389(10) 0.0631(4) Uani 1 1 d . . .
O8 O 0.49057(15) 0.56539(16) 0.35700(15) 0.0790(5) Uani 1 1 d . B .
O9 O 0.69252(13) 0.48954(12) 0.39370(10) 0.0486(3) Uani 1 1 d . B .


_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 1.385(3) . ?
C1 C6 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(2) . ?
C7 N1 1.463(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.2153(19) . ?
C8 N1 1.366(2) . ?
C8 C9 1.571(2) . ?
C9 C10 1.527(2) . ?
C9 C30 1.544(2) . ?
C9 C17 1.549(2) . ?
C10 C11 1.376(2) . ?
C10 C16 1.394(2) . ?
C11 C12 1.402(2) . ?
C11 H11 0.9300 . ?
C12 C14 1.388(3) . ?
C12 C13 1.512(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9300 . ?
C16 N1 1.407(2) . ?
C17 C20 1.338(2) . ?
C17 C18 1.506(2) . ?
C18 O2 1.2018(19) . ?
C18 O3 1.3348(19) . ?
C19 O3 1.461(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.498(2) . ?
C20 C23 1.512(2) . ?
C21 O4 1.203(2) . ?
C21 O5 1.321(2) . ?
C22 O5 1.452(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N2 1.462(2) . ?
C23 C24 1.539(2) . ?
C23 H23 0.9800 . ?
C24 C25 1.408(7) . ?
C24 C25' 1.621(13) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C24 H24D 0.9700 . ?
C25 C26 1.615(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25' C26 1.338(10) . ?
C25' H25C 0.9700 . ?
C25' H25D 0.9700 . ?
C26 N2 1.462(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C26 H26D 0.9700 . ?
C27 N2 1.355(2) . ?
C27 C30 1.372(2) . ?
C27 C28 1.517(2) . ?
C28 O6 1.196(2) . ?
C28 O7 1.328(2) . ?
C29 O7 1.451(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.475(2) . ?
C31 O8 1.206(2) . ?
C31 O9 1.344(2) . ?
C32 O9 1.439(2) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 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 120.52(19) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.47(18) . . ?
C1 C6 C7 122.75(15) . . ?
C5 C6 C7 118.77(16) . . ?
N1 C7 C6 114.37(14) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 125.76(15) . . ?
O1 C8 C9 126.23(14) . . ?
N1 C8 C9 108.01(13) . . ?
C10 C9 C30 109.72(12) . . ?
C10 C9 C17 108.77(12) . . ?
C30 C9 C17 114.59(12) . . ?
C10 C9 C8 101.00(11) . . ?
C30 C9 C8 113.60(12) . . ?
C17 C9 C8 108.23(12) . . ?
C11 C10 C16 120.20(14) . . ?
C11 C10 C9 130.61(14) . . ?
C16 C10 C9 109.09(13) . . ?
C10 C11 C12 120.01(15) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C14 C12 C11 118.37(16) . . ?
C14 C12 C13 121.21(16) . . ?
C11 C12 C13 120.40(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 122.53(15) . . ?
C12 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C16 C15 C14 117.59(16) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C10 121.27(15) . . ?
C15 C16 N1 128.65(15) . . ?
C10 C16 N1 110.07(13) . . ?
C20 C17 C18 120.94(14) . . ?
C20 C17 C9 125.13(14) . . ?
C18 C17 C9 113.85(12) . . ?
O2 C18 O3 124.97(14) . . ?
O2 C18 C17 123.47(14) . . ?
O3 C18 C17 111.51(13) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 C21 121.55(14) . . ?
C17 C20 C23 120.33(14) . . ?
C21 C20 C23 117.98(13) . . ?
O4 C21 O5 124.30(16) . . ?
O4 C21 C20 123.59(16) . . ?
O5 C21 C20 112.07(13) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 C20 109.93(14) . . ?
N2 C23 C24 104.33(15) . . ?
C20 C23 C24 118.12(15) . . ?
N2 C23 H23 108.0 . . ?
C20 C23 H23 108.0 . . ?
C24 C23 H23 108.0 . . ?
C25 C24 C23 107.7(3) . . ?
C25 C24 C25' 32.1(3) . . ?
C23 C24 C25' 101.5(4) . . ?
C25 C24 H24A 110.2 . . ?
C23 C24 H24A 110.2 . . ?
C25' C24 H24A 138.6 . . ?
C25 C24 H24B 110.2 . . ?
C23 C24 H24B 110.2 . . ?
C25' C24 H24B 83.8 . . ?
H24A C24 H24B 108.5 . . ?
C25 C24 H24C 131.8 . . ?
C23 C24 H24C 111.5 . . ?
C25' C24 H24C 111.5 . . ?
H24A C24 H24C 81.4 . . ?
H24B C24 H24C 29.1 . . ?
C25 C24 H24D 80.1 . . ?
C23 C24 H24D 111.5 . . ?
C25' C24 H24D 111.5 . . ?
H24A C24 H24D 31.8 . . ?
H24B C24 H24D 131.0 . . ?
H24C C24 H24D 109.3 . . ?
C24 C25 C26 105.0(4) . . ?
C24 C25 H25A 110.7 . . ?
C26 C25 H25A 110.7 . . ?
C24 C25 H25B 110.7 . . ?
C26 C25 H25B 110.7 . . ?
H25A C25 H25B 108.8 . . ?
C26 C25' C24 108.1(5) . . ?
C26 C25' H25C 110.1 . . ?
C24 C25' H25C 110.1 . . ?
C26 C25' H25D 110.1 . . ?
C24 C25' H25D 110.1 . . ?
H25C C25' H25D 108.4 . . ?
C25' C26 N2 108.8(4) . . ?
C25' C26 C25 32.3(5) . . ?
N2 C26 C25 99.8(3) . . ?
C25' C26 H26A 130.1 . . ?
N2 C26 H26A 111.8 . . ?
C25 C26 H26A 111.8 . . ?
C25' C26 H26B 79.8 . . ?
N2 C26 H26B 111.8 . . ?
C25 C26 H26B 111.8 . . ?
H26A C26 H26B 109.5 . . ?
C25' C26 H26C 109.9 . . ?
N2 C26 H26C 109.9 . . ?
C25 C26 H26C 139.8 . . ?
H26A C26 H26C 81.9 . . ?
H26B C26 H26C 31.9 . . ?
C25' C26 H26D 109.9 . . ?
N2 C26 H26D 109.9 . . ?
C25 C26 H26D 85.1 . . ?
H26A C26 H26D 28.1 . . ?
H26B C26 H26D 130.8 . . ?
H26C C26 H26D 108.3 . . ?
N2 C27 C30 127.37(16) . . ?
N2 C27 C28 113.10(14) . . ?
C30 C27 C28 119.27(16) . . ?
O6 C28 O7 124.86(17) . . ?
O6 C28 C27 123.51(16) . . ?
O7 C28 C27 111.45(14) . . ?
O7 C29 H29A 109.5 . . ?
O7 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O7 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 C31 115.10(14) . . ?
C27 C30 C9 129.23(15) . . ?
C31 C30 C9 115.67(13) . . ?
O8 C31 O9 122.47(17) . . ?
O8 C31 C30 125.79(17) . . ?
O9 C31 C30 111.70(14) . . ?
O9 C32 H32A 109.5 . . ?
O9 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O9 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C8 N1 C16 111.70(13) . . ?
C8 N1 C7 123.11(14) . . ?
C16 N1 C7 124.41(14) . . ?
C27 N2 C23 120.14(13) . . ?
C27 N2 C26 126.79(17) . . ?
C23 N2 C26 111.89(16) . . ?
C18 O3 C19 115.49(13) . . ?
C21 O5 C22 116.86(15) . . ?
C28 O7 C29 114.78(16) . . ?
C31 O9 C32 116.97(16) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1043446'
_audit_update_record             
;
2015-01-14 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H31 F N2 O9'
_chemical_formula_sum            'C28 H31 F N2 O9'
_chemical_formula_weight         558.55

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                   10.200(2)
_cell_length_b                   12.129(2)
_cell_length_c                   22.985(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.804(6)
_cell_angle_gamma                90.00
_cell_volume                     2840.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      24.93

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.974
_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            27342
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         27.55
_reflns_number_total             6503
_reflns_number_gt                4183
_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)+(0.1130P)²+0.8619P] 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         6503
_refine_ls_number_parameters     377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.2162
_refine_ls_wR_factor_gt          0.1774
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 0.0336(10) 0.7966(7) 0.0569(3) 0.144(5) Uani 0.703(13) 1 d P A 1
H1A H -0.0341 0.7593 0.0341 0.217 Uiso 0.703(13) 1 calc PR A 1
H1B H 0.1172 0.7819 0.0411 0.217 Uiso 0.703(13) 1 calc PR A 1
H1C H 0.0171 0.8745 0.0561 0.217 Uiso 0.703(13) 1 calc PR A 1
C1' C -0.095(2) 0.803(2) 0.0974(13) 0.182(13) Uani 0.297(13) 1 d P A 2
H1'1 H -0.1630 0.7490 0.1024 0.272 Uiso 0.297(13) 1 calc PR A 2
H1'2 H -0.0923 0.8213 0.0569 0.272 Uiso 0.297(13) 1 calc PR A 2
H1'3 H -0.1139 0.8678 0.1193 0.272 Uiso 0.297(13) 1 calc PR A 2
C2 C 0.0345(5) 0.7561(4) 0.1186(3) 0.1154(16) Uani 1 1 d . . .
H2A H -0.0505 0.7707 0.1341 0.138 Uiso 0.703(13) 1 calc PR A 1
H2B H 0.0476 0.6769 0.1188 0.138 Uiso 0.703(13) 1 calc PR A 1
H2C H 0.0136 0.6873 0.1376 0.138 Uiso 0.297(13) 1 d PR A 2
H2D H 0.0781 0.7357 0.0836 0.138 Uiso 0.297(13) 1 d PR A 2
C3 C 0.1364(4) 0.8074(3) 0.1566(2) 0.0923(12) Uani 1 1 d . A .
H3A H 0.1203 0.7890 0.1967 0.111 Uiso 1 1 calc R . .
H3B H 0.1297 0.8868 0.1526 0.111 Uiso 1 1 calc R . .
C4 C 0.2722(3) 0.7733(2) 0.14428(16) 0.0666(8) Uani 1 1 d . . .
H4A H 0.2847 0.7832 0.1030 0.080 Uiso 1 1 calc R A .
H4B H 0.3334 0.8218 0.1654 0.080 Uiso 1 1 calc R . .
C5 C 0.3051(2) 0.57570(19) 0.12054(11) 0.0400(5) Uani 1 1 d . . .
C6 C 0.3599(2) 0.47033(18) 0.15242(9) 0.0343(5) Uani 1 1 d . A .
C7 C 0.3746(2) 0.51235(19) 0.21484(9) 0.0358(5) Uani 1 1 d . . .
C8 C 0.3418(2) 0.6238(2) 0.21602(11) 0.0428(6) Uani 1 1 d . A .
C9 C 0.3485(3) 0.6824(2) 0.26762(13) 0.0603(8) Uani 1 1 d . . .
H9 H 0.3262 0.7567 0.2684 0.072 Uiso 1 1 calc R A .
C10 C 0.3891(3) 0.6280(3) 0.31807(13) 0.0699(9) Uani 1 1 d . A .
H10 H 0.3945 0.6653 0.3534 0.084 Uiso 1 1 calc R . .
C11 C 0.4212(3) 0.5192(3) 0.31560(11) 0.0623(8) Uani 1 1 d . . .
C12 C 0.4154(2) 0.4582(2) 0.26483(10) 0.0461(6) Uani 1 1 d . A .
H12 H 0.4381 0.3839 0.2646 0.055 Uiso 1 1 calc R . .
C13 C 0.2647(2) 0.37193(18) 0.14917(9) 0.0363(5) Uani 1 1 d . . .
C14 C 0.1543(2) 0.3787(2) 0.18828(10) 0.0409(5) Uani 1 1 d . A .
C15 C 0.0167(3) 0.5025(3) 0.23597(14) 0.0686(9) Uani 1 1 d . A .
H15A H -0.0655 0.4681 0.2249 0.103 Uiso 1 1 calc R . .
H15B H 0.0039 0.5805 0.2399 0.103 Uiso 1 1 calc R . .
H15C H 0.0498 0.4727 0.2725 0.103 Uiso 1 1 calc R . .
C16 C 0.2705(2) 0.27806(19) 0.11723(10) 0.0407(5) Uani 1 1 d . A .
C17 C 0.1751(3) 0.1848(2) 0.12766(12) 0.0487(6) Uani 1 1 d . . .
C18 C -0.0425(3) 0.1271(3) 0.1074(2) 0.0946(13) Uani 1 1 d . . .
H18A H -0.0076 0.0541 0.1035 0.142 Uiso 1 1 calc R A .
H18B H -0.1119 0.1386 0.0783 0.142 Uiso 1 1 calc R . .
H18C H -0.0762 0.1355 0.1454 0.142 Uiso 1 1 calc R . .
C19 C 0.4975(2) 0.44853(17) 0.12987(9) 0.0346(5) Uani 1 1 d . . .
C20 C 0.6097(2) 0.4968(2) 0.16601(10) 0.0383(5) Uani 1 1 d . A .
C21 C 0.7032(3) 0.6620(3) 0.20120(17) 0.0802(10) Uani 1 1 d . A .
H21A H 0.6959 0.6374 0.2406 0.120 Uiso 1 1 calc R . .
H21B H 0.6883 0.7401 0.1992 0.120 Uiso 1 1 calc R . .
H21C H 0.7895 0.6458 0.1887 0.120 Uiso 1 1 calc R . .
C22 C 0.5232(2) 0.39269(19) 0.08177(10) 0.0387(5) Uani 1 1 d . A .
C23 C 0.6631(3) 0.3721(2) 0.06777(11) 0.0453(6) Uani 1 1 d . . .
C24 C 0.8706(3) 0.4511(3) 0.05759(16) 0.0729(9) Uani 1 1 d . . .
H24A H 0.9103 0.4140 0.0909 0.109 Uiso 1 1 calc R A .
H24B H 0.9103 0.5222 0.0536 0.109 Uiso 1 1 calc R . .
H24C H 0.8834 0.4082 0.0232 0.109 Uiso 1 1 calc R . .
C25 C 0.4132(3) 0.3440(2) 0.04324(10) 0.0471(6) Uani 1 1 d . . .
H25 H 0.3479 0.4018 0.0349 0.056 Uiso 1 1 calc R A .
C26 C 0.4491(3) 0.2915(3) -0.01510(12) 0.0659(8) Uani 1 1 d . A .
H26A H 0.3835 0.3087 -0.0457 0.079 Uiso 1 1 calc R . .
H26B H 0.5340 0.3173 -0.0266 0.079 Uiso 1 1 calc R . .
C27 C 0.4523(4) 0.1696(3) -0.00268(16) 0.0849(11) Uani 1 1 d . . .
H27A H 0.5372 0.1477 0.0144 0.102 Uiso 1 1 calc R A .
H27B H 0.4344 0.1276 -0.0381 0.102 Uiso 1 1 calc R . .
C28 C 0.3460(3) 0.1519(2) 0.03976(13) 0.0639(8) Uani 1 1 d . A .
H28A H 0.2612 0.1415 0.0196 0.077 Uiso 1 1 calc R . .
H28B H 0.3652 0.0886 0.0646 0.077 Uiso 1 1 calc R . .
F1 F 0.4609(2) 0.4662(2) 0.36595(7) 0.0958(7) Uani 1 1 d . A .
N1 N 0.3040(2) 0.65939(16) 0.15996(9) 0.0442(5) Uani 1 1 d . A .
N2 N 0.3496(2) 0.25468(17) 0.07355(9) 0.0482(5) Uani 1 1 d . A .
O1 O 0.2734(2) 0.58190(15) 0.06932(8) 0.0553(5) Uani 1 1 d . A .
O2 O 0.1062(2) 0.30367(17) 0.21360(9) 0.0686(6) Uani 1 1 d . . .
O3 O 0.10953(16) 0.48202(14) 0.19192(8) 0.0477(4) Uani 1 1 d . . .
O4 O 0.2018(2) 0.10190(16) 0.15339(10) 0.0668(6) Uani 1 1 d . A .
O5 O 0.06067(18) 0.20730(16) 0.09975(9) 0.0610(5) Uani 1 1 d . A .
O6 O 0.69020(18) 0.44367(15) 0.19328(9) 0.0551(5) Uani 1 1 d . . .
O7 O 0.60659(16) 0.60592(14) 0.16376(8) 0.0478(4) Uani 1 1 d . . .
O8 O 0.70558(19) 0.28131(16) 0.06050(9) 0.0641(6) Uani 1 1 d . A .
O9 O 0.73240(17) 0.46423(15) 0.06517(8) 0.0507(5) Uani 1 1 d . A .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.499(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H2D 1.0487 . ?
C1' C2 1.50(2) . ?
C1' H1'1 0.9600 . ?
C1' H1'2 0.9600 . ?
C1' H1'3 0.9600 . ?
C2 C3 1.464(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.485(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.461(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.208(3) . ?
C5 N1 1.361(3) . ?
C5 C6 1.563(3) . ?
C6 C7 1.523(3) . ?
C6 C13 1.538(3) . ?
C6 C19 1.543(3) . ?
C7 C12 1.370(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.381(4) . ?
C8 N1 1.395(3) . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(5) . ?
C10 H10 0.9300 . ?
C11 F1 1.367(3) . ?
C11 C12 1.380(4) . ?
C12 H12 0.9300 . ?
C13 C16 1.358(3) . ?
C13 C14 1.476(3) . ?
C14 O2 1.198(3) . ?
C14 O3 1.338(3) . ?
C15 O3 1.441(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N2 1.349(3) . ?
C16 C17 1.519(3) . ?
C17 O4 1.191(3) . ?
C17 O5 1.333(3) . ?
C18 O5 1.450(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C22 1.333(3) . ?
C19 C20 1.500(3) . ?
C20 O6 1.196(3) . ?
C20 O7 1.325(3) . ?
C21 O7 1.447(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.499(3) . ?
C22 C25 1.515(4) . ?
C23 O8 1.198(3) . ?
C23 O9 1.326(3) . ?
C24 O9 1.437(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 N2 1.457(3) . ?
C25 C26 1.544(4) . ?
C25 H25 0.9800 . ?
C26 C27 1.506(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.509(5) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 N2 1.468(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?

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 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H2D 40.1 . . ?
H1A C1 H2D 105.5 . . ?
H1B C1 H2D 74.0 . . ?
H1C C1 H2D 140.8 . . ?
C2 C1' H1'1 109.5 . . ?
C2 C1' H1'2 109.5 . . ?
H1'1 C1' H1'2 109.5 . . ?
C2 C1' H1'3 109.5 . . ?
H1'1 C1' H1'3 109.5 . . ?
H1'2 C1' H1'3 109.5 . . ?
C3 C2 C1 113.3(6) . . ?
C3 C2 C1' 128.6(12) . . ?
C1 C2 C1' 66.8(11) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C1' C2 H2A 42.2 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C1' C2 H2B 119.7 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2C 105.1 . . ?
C1 C2 H2C 135.7 . . ?
C1' C2 H2C 105.1 . . ?
H2A C2 H2C 76.8 . . ?
H2B C2 H2C 34.8 . . ?
C3 C2 H2D 105.1 . . ?
C1 C2 H2D 44.1 . . ?
C1' C2 H2D 105.1 . . ?
H2A C2 H2D 143.8 . . ?
H2B C2 H2D 71.6 . . ?
H2C C2 H2D 105.9 . . ?
C2 C3 C4 114.2(4) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N1 C4 C3 114.4(3) . . ?
N1 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
O1 C5 N1 126.3(2) . . ?
O1 C5 C6 125.5(2) . . ?
N1 C5 C6 108.2(2) . . ?
C7 C6 C13 109.76(17) . . ?
C7 C6 C19 108.94(17) . . ?
C13 C6 C19 115.68(18) . . ?
C7 C6 C5 100.63(17) . . ?
C13 C6 C5 113.69(18) . . ?
C19 C6 C5 107.02(17) . . ?
C12 C7 C8 120.8(2) . . ?
C12 C7 C6 129.9(2) . . ?
C8 C7 C6 109.29(19) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 N1 129.3(2) . . ?
C7 C8 N1 109.7(2) . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 F1 118.8(3) . . ?
C10 C11 C12 123.6(3) . . ?
F1 C11 C12 117.6(3) . . ?
C7 C12 C11 116.8(3) . . ?
C7 C12 H12 121.6 . . ?
C11 C12 H12 121.6 . . ?
C16 C13 C14 115.5(2) . . ?
C16 C13 C6 129.3(2) . . ?
C14 C13 C6 115.19(18) . . ?
O2 C14 O3 122.1(2) . . ?
O2 C14 C13 126.6(2) . . ?
O3 C14 C13 111.26(19) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C13 128.5(2) . . ?
N2 C16 C17 111.8(2) . . ?
C13 C16 C17 119.6(2) . . ?
O4 C17 O5 125.8(2) . . ?
O4 C17 C16 125.1(2) . . ?
O5 C17 C16 108.9(2) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C19 C20 118.8(2) . . ?
C22 C19 C6 125.7(2) . . ?
C20 C19 C6 115.43(18) . . ?
O6 C20 O7 125.0(2) . . ?
O6 C20 C19 124.5(2) . . ?
O7 C20 C19 110.59(19) . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 C23 119.4(2) . . ?
C19 C22 C25 120.9(2) . . ?
C23 C22 C25 119.7(2) . . ?
O8 C23 O9 124.8(2) . . ?
O8 C23 C22 122.6(2) . . ?
O9 C23 C22 112.6(2) . . ?
O9 C24 H24A 109.5 . . ?
O9 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O9 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C25 C22 110.15(19) . . ?
N2 C25 C26 103.8(2) . . ?
C22 C25 C26 117.9(2) . . ?
N2 C25 H25 108.2 . . ?
C22 C25 H25 108.2 . . ?
C26 C25 H25 108.2 . . ?
C27 C26 C25 104.1(2) . . ?
C27 C26 H26A 110.9 . . ?
C25 C26 H26A 110.9 . . ?
C27 C26 H26B 110.9 . . ?
C25 C26 H26B 110.9 . . ?
H26A C26 H26B 108.9 . . ?
C26 C27 C28 104.6(3) . . ?
C26 C27 H27A 110.8 . . ?
C28 C27 H27A 110.8 . . ?
C26 C27 H27B 110.8 . . ?
C28 C27 H27B 110.8 . . ?
H27A C27 H27B 108.9 . . ?
N2 C28 C27 102.8(2) . . ?
N2 C28 H28A 111.2 . . ?
C27 C28 H28A 111.2 . . ?
N2 C28 H28B 111.2 . . ?
C27 C28 H28B 111.2 . . ?
H28A C28 H28B 109.1 . . ?
C5 N1 C8 111.91(19) . . ?
C5 N1 C4 123.4(2) . . ?
C8 N1 C4 124.6(2) . . ?
C16 N2 C25 119.7(2) . . ?
C16 N2 C28 124.9(2) . . ?
C25 N2 C28 112.2(2) . . ?
C14 O3 C15 116.3(2) . . ?
C17 O5 C18 115.3(2) . . ?
C20 O7 C21 115.6(2) . . ?
C23 O9 C24 116.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.215


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