# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_3f
_audit_block_doi                 10.5517/cc13k6jd
_database_code_depnum_ccdc_archive 'CCDC 1029433'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H37 Cl3 N2 O7, C3 H7 N O'
_chemical_formula_sum            'C49 H44 Cl3 N3 O8'
_chemical_formula_weight         909.22

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                   11.5355(12)
_cell_length_b                   12.0272(13)
_cell_length_c                   16.4726(17)
_cell_angle_alpha                105.258(3)
_cell_angle_beta                 90.346(3)
_cell_angle_gamma                91.168(3)
_cell_volume                     2204.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.43

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_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    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             948
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.923
_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            46666
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         27.59
_reflns_number_total             10202
_reflns_number_gt                6729
_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)+(0.0775P)²+1.1458P] 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         10160
_refine_ls_number_parameters     573
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1465
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.032
_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 0.9287(4) 0.2144(4) 0.4362(2) 0.0978(13) Uani 1 1 d . . .
H1A H 0.9787 0.1513 0.4351 0.147 Uiso 1 1 calc R . .
H1B H 0.9537 0.2532 0.3951 0.147 Uiso 1 1 calc R . .
H1C H 0.8506 0.1858 0.4234 0.147 Uiso 1 1 calc R . .
C2 C 0.9332(3) 0.2950(3) 0.51954(18) 0.0704(9) Uani 1 1 d . . .
H2A H 0.8826 0.3590 0.5214 0.085 Uiso 1 1 calc R . .
H2B H 1.0116 0.3252 0.5328 0.085 Uiso 1 1 calc R . .
C3 C 0.8940(2) 0.2943(2) 0.65967(14) 0.0407(5) Uani 1 1 d . . .
C4 C 0.85364(18) 0.22605(18) 0.71850(13) 0.0319(5) Uani 1 1 d . . .
C5 C 0.9233(2) 0.36428(19) 0.85203(13) 0.0357(5) Uani 1 1 d . . .
C6 C 0.81488(19) 0.29661(17) 0.80401(13) 0.0323(5) Uani 1 1 d . . .
C7 C 0.7366(2) 0.39571(18) 0.80013(13) 0.0345(5) Uani 1 1 d . . .
C8 C 0.6307(2) 0.3968(2) 0.76268(15) 0.0419(6) Uani 1 1 d . . .
H8 H 0.5928 0.3287 0.7340 0.050 Uiso 1 1 calc R . .
C9 C 0.5814(2) 0.5035(2) 0.76895(17) 0.0494(6) Uani 1 1 d . . .
C10 C 0.6347(3) 0.6054(2) 0.81093(18) 0.0556(7) Uani 1 1 d . . .
H10 H 0.5989 0.6749 0.8140 0.067 Uiso 1 1 calc R . .
C11 C 0.7419(3) 0.6045(2) 0.84880(17) 0.0515(7) Uani 1 1 d . . .
H11 H 0.7792 0.6729 0.8777 0.062 Uiso 1 1 calc R . .
C12 C 0.7917(2) 0.49971(19) 0.84256(14) 0.0392(5) Uani 1 1 d . . .
C13 C 0.9801(3) 0.5684(2) 0.92127(15) 0.0494(6) Uani 1 1 d . . .
H13A H 1.0410 0.5317 0.9450 0.059 Uiso 1 1 calc R . .
H13B H 0.9383 0.6169 0.9678 0.059 Uiso 1 1 calc R . .
C14 C 1.0357(2) 0.6442(2) 0.87157(16) 0.0458(6) Uani 1 1 d . . .
C15 C 1.0438(3) 0.7621(2) 0.9062(2) 0.0619(8) Uani 1 1 d . . .
H15 H 1.0111 0.7947 0.9582 0.074 Uiso 1 1 calc R . .
C16 C 1.1003(3) 0.8317(3) 0.8635(3) 0.0806(11) Uani 1 1 d . . .
H16 H 1.1054 0.9109 0.8871 0.097 Uiso 1 1 calc R . .
C17 C 1.1487(3) 0.7844(3) 0.7869(3) 0.0825(12) Uani 1 1 d . . .
H17 H 1.1866 0.8315 0.7584 0.099 Uiso 1 1 calc R . .
C18 C 1.1414(3) 0.6681(3) 0.7524(2) 0.0777(10) Uani 1 1 d . . .
H18 H 1.1748 0.6359 0.7005 0.093 Uiso 1 1 calc R . .
C19 C 1.0840(3) 0.5980(3) 0.79463(19) 0.0614(8) Uani 1 1 d . . .
H19 H 1.0783 0.5189 0.7705 0.074 Uiso 1 1 calc R . .
C20 C 0.6769(4) 0.5468(3) 1.0623(3) 0.1170(17) Uani 1 1 d D . .
H20A H 0.7581 0.5640 1.0732 0.176 Uiso 1 1 calc R . .
H20B H 0.6331 0.5884 1.1095 0.176 Uiso 1 1 calc R . .
H20C H 0.6538 0.5691 1.0129 0.176 Uiso 1 1 calc R . .
C21 C 0.6549(3) 0.4206(3) 1.0488(2) 0.0964(14) Uani 1 1 d D . .
H21A H 0.6707 0.3991 1.1004 0.116 Uiso 1 1 calc R . .
H21B H 0.5742 0.4019 1.0333 0.116 Uiso 1 1 calc R . .
C22 C 0.6787(2) 0.27597(19) 0.92033(14) 0.0376(5) Uani 1 1 d . . .
C23 C 0.76853(19) 0.21581(17) 0.85933(13) 0.0306(4) Uani 1 1 d . . .
H23 H 0.8347 0.2050 0.8938 0.037 Uiso 1 1 calc R . .
C24 C 0.61425(19) 0.08899(17) 0.75837(14) 0.0332(5) Uani 1 1 d . . .
C25 C 0.72579(18) 0.09252(17) 0.81074(13) 0.0301(4) Uani 1 1 d . . .
C26 C 0.68969(19) 0.01898(17) 0.86879(13) 0.0333(5) Uani 1 1 d . . .
C27 C 0.7487(2) -0.01031(19) 0.93233(14) 0.0402(5) Uani 1 1 d . . .
H27 H 0.8237 0.0177 0.9476 0.048 Uiso 1 1 calc R . .
C28 C 0.6925(3) -0.0837(2) 0.97339(15) 0.0478(6) Uani 1 1 d . . .
C29 C 0.5814(3) -0.1248(2) 0.95299(16) 0.0505(7) Uani 1 1 d . . .
H29 H 0.5461 -0.1723 0.9824 0.061 Uiso 1 1 calc R . .
C30 C 0.5216(2) -0.0959(2) 0.88877(17) 0.0469(6) Uani 1 1 d . . .
H30 H 0.4465 -0.1237 0.8740 0.056 Uiso 1 1 calc R . .
C31 C 0.5773(2) -0.02412(18) 0.84702(14) 0.0368(5) Uani 1 1 d . . .
C32 C 0.4201(2) -0.0046(2) 0.74195(18) 0.0492(6) Uani 1 1 d . . .
H32A H 0.3924 0.0668 0.7327 0.059 Uiso 1 1 calc R . .
H32B H 0.3676 -0.0276 0.7806 0.059 Uiso 1 1 calc R . .
C33 C 0.4170(2) -0.0961(2) 0.65942(17) 0.0457(6) Uani 1 1 d . . .
C34 C 0.4169(3) -0.2122(2) 0.65670(18) 0.0572(7) Uani 1 1 d . . .
H34 H 0.4204 -0.2345 0.7066 0.069 Uiso 1 1 calc R . .
C35 C 0.4118(3) -0.2949(3) 0.5811(2) 0.0711(9) Uani 1 1 d . . .
H35 H 0.4121 -0.3725 0.5802 0.085 Uiso 1 1 calc R . .
C36 C 0.4061(3) -0.2635(3) 0.5069(2) 0.0747(9) Uani 1 1 d . . .
H36 H 0.4016 -0.3196 0.4558 0.090 Uiso 1 1 calc R . .
C37 C 0.4073(3) -0.1495(3) 0.5086(2) 0.0725(9) Uani 1 1 d . . .
H37 H 0.4036 -0.1279 0.4585 0.087 Uiso 1 1 calc R . .
C38 C 0.4138(3) -0.0662(3) 0.5842(2) 0.0595(7) Uani 1 1 d . . .
H38 H 0.4161 0.0112 0.5844 0.071 Uiso 1 1 calc R . .
C39 C 0.86034(18) 0.11224(18) 0.69706(13) 0.0324(5) Uani 1 1 d . . .
H39 H 0.8870 0.0768 0.6435 0.039 Uiso 1 1 calc R . .
C40 C 0.82777(18) 0.03557(17) 0.75345(13) 0.0307(5) Uani 1 1 d . . .
C41 C 0.79541(19) -0.08622(18) 0.70075(14) 0.0334(5) Uani 1 1 d . . .
C42 C 0.8342(2) -0.1821(2) 0.72398(16) 0.0444(6) Uani 1 1 d . . .
H42 H 0.8775 -0.1719 0.7733 0.053 Uiso 1 1 calc R . .
C43 C 0.8095(3) -0.2925(2) 0.67491(18) 0.0545(7) Uani 1 1 d . . .
H43 H 0.8365 -0.3563 0.6906 0.065 Uiso 1 1 calc R . .
C44 C 0.7450(3) -0.3062(2) 0.60326(19) 0.0554(7) Uani 1 1 d . . .
C45 C 0.7027(2) -0.2135(2) 0.57913(17) 0.0529(7) Uani 1 1 d . . .
H45 H 0.6567 -0.2246 0.5310 0.063 Uiso 1 1 calc R . .
C46 C 0.7299(2) -0.1038(2) 0.62781(15) 0.0421(5) Uani 1 1 d . . .
H46 H 0.7036 -0.0405 0.6112 0.051 Uiso 1 1 calc R . .
C47 C 0.8413(3) 0.8672(4) 0.2694(3) 0.0910(12) Uani 1 1 d . . .
H47 H 0.8312 0.8180 0.2158 0.109 Uiso 1 1 calc R . .
C48 C 0.7607(5) 0.7174(5) 0.3280(5) 0.162(3) Uani 1 1 d . . .
H48A H 0.6894 0.7286 0.3586 0.242 Uiso 1 1 calc R . .
H48B H 0.8125 0.6745 0.3534 0.242 Uiso 1 1 calc R . .
H48C H 0.7450 0.6756 0.2707 0.242 Uiso 1 1 calc R . .
C49 C 0.8370(4) 0.8986(5) 0.4165(3) 0.1142(15) Uani 1 1 d . . .
H49A H 0.8925 0.9579 0.4135 0.171 Uiso 1 1 calc R . .
H49B H 0.8681 0.8523 0.4505 0.171 Uiso 1 1 calc R . .
H49C H 0.7669 0.9332 0.4411 0.171 Uiso 1 1 calc R . .
Cl1 Cl 0.76690(9) -0.12531(7) 1.05261(5) 0.0756(3) Uani 1 1 d . . .
Cl2 Cl 0.44700(7) 0.50768(7) 0.72093(6) 0.0776(3) Uani 1 1 d . . .
Cl3 Cl 0.71397(11) -0.44472(7) 0.54011(7) 0.1039(4) Uani 1 1 d . . .
N1 N 0.53561(16) 0.01647(15) 0.78070(12) 0.0376(4) Uani 1 1 d . . .
N2 N 0.90039(17) 0.47912(15) 0.87317(12) 0.0393(5) Uani 1 1 d . . .
N3 N 0.8116(3) 0.8244(3) 0.3301(2) 0.0848(9) Uani 1 1 d . . .
O1 O 0.89543(18) 0.23269(15) 0.58028(10) 0.0541(5) Uani 1 1 d . . .
O2 O 0.9227(2) 0.39355(16) 0.68157(12) 0.0727(7) Uani 1 1 d . . .
O3 O 1.01137(15) 0.32151(15) 0.86858(11) 0.0474(4) Uani 1 1 d . . .
O4 O 0.72894(16) 0.35693(16) 0.98238(11) 0.0577(5) Uani 1 1 d . . .
O5 O 0.57664(15) 0.25465(15) 0.91459(12) 0.0538(5) Uani 1 1 d . . .
O6 O 0.59702(14) 0.13814(13) 0.70368(10) 0.0423(4) Uani 1 1 d . . .
O7 O 0.91943(13) 0.03186(14) 0.80972(10) 0.0391(4) Uani 1 1 d . . .
H7 H 0.9814 0.0301 0.7854 0.059 Uiso 1 1 calc R . .
O8 O 0.8794(2) 0.9591(3) 0.27160(18) 0.0926(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 C2 1.457(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.462(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.192(3) . ?
C3 O1 1.323(3) . ?
C3 C4 1.496(3) . ?
C4 C39 1.325(3) . ?
C4 C6 1.516(3) . ?
C5 O3 1.209(3) . ?
C5 N2 1.364(3) . ?
C5 C6 1.569(3) . ?
C6 C7 1.524(3) . ?
C6 C23 1.585(3) . ?
C7 C8 1.368(3) . ?
C7 C12 1.400(3) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(4) . ?
C9 Cl2 1.744(3) . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 N2 1.399(3) . ?
C13 N2 1.460(3) . ?
C13 C14 1.512(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.370(4) . ?
C14 C15 1.383(4) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.4904(19) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O4 1.452(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O5 1.198(3) . ?
C22 O4 1.332(3) . ?
C22 C23 1.506(3) . ?
C23 C25 1.557(3) . ?
C23 H23 0.9800 . ?
C24 O6 1.218(3) . ?
C24 N1 1.364(3) . ?
C24 C25 1.538(3) . ?
C25 C26 1.518(3) . ?
C25 C40 1.565(3) . ?
C26 C27 1.371(3) . ?
C26 C31 1.396(3) . ?
C27 C28 1.398(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.372(4) . ?
C28 Cl1 1.743(3) . ?
C29 C30 1.382(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.388(3) . ?
C30 H30 0.9300 . ?
C31 N1 1.395(3) . ?
C32 N1 1.462(3) . ?
C32 C33 1.507(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C38 1.379(4) . ?
C33 C34 1.386(4) . ?
C34 C35 1.374(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.373(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.363(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.378(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C40 1.515(3) . ?
C39 H39 0.9300 . ?
C40 O7 1.411(3) . ?
C40 C41 1.531(3) . ?
C41 C46 1.381(3) . ?
C41 C42 1.388(3) . ?
C42 C43 1.384(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.362(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.376(4) . ?
C44 Cl3 1.745(3) . ?
C45 C46 1.381(3) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 O8 1.172(5) . ?
C47 N3 1.284(5) . ?
C47 H47 0.9300 . ?
C48 N3 1.396(5) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 N3 1.492(6) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
O7 H7 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
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 O1 107.8(3) . . ?
C1 C2 H2A 110.1 . . ?
O1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
O1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 123.1(2) . . ?
O2 C3 C4 123.9(2) . . ?
O1 C3 C4 112.93(19) . . ?
C39 C4 C3 120.47(19) . . ?
C39 C4 C6 124.00(18) . . ?
C3 C4 C6 115.37(18) . . ?
O3 C5 N2 126.0(2) . . ?
O3 C5 C6 125.6(2) . . ?
N2 C5 C6 108.4(2) . . ?
C4 C6 C7 113.78(17) . . ?
C4 C6 C5 108.25(17) . . ?
C7 C6 C5 100.96(17) . . ?
C4 C6 C23 111.03(16) . . ?
C7 C6 C23 115.41(17) . . ?
C5 C6 C23 106.41(16) . . ?
C8 C7 C12 119.8(2) . . ?
C8 C7 C6 131.41(19) . . ?
C12 C7 C6 108.8(2) . . ?
C7 C8 C9 117.7(2) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C10 C9 C8 122.6(3) . . ?
C10 C9 Cl2 118.7(2) . . ?
C8 C9 Cl2 118.8(2) . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 N2 127.7(2) . . ?
C11 C12 C7 121.9(2) . . ?
N2 C12 C7 110.4(2) . . ?
N2 C13 C14 115.0(2) . . ?
N2 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
N2 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C19 C14 C15 119.0(2) . . ?
C19 C14 C13 121.3(2) . . ?
C15 C14 C13 119.6(3) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.6(3) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 C20 109.7(3) . . ?
O4 C21 H21A 109.7 . . ?
C20 C21 H21A 109.7 . . ?
O4 C21 H21B 109.7 . . ?
C20 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
O5 C22 O4 124.4(2) . . ?
O5 C22 C23 125.4(2) . . ?
O4 C22 C23 110.23(19) . . ?
C22 C23 C25 111.20(17) . . ?
C22 C23 C6 110.77(17) . . ?
C25 C23 C6 116.49(16) . . ?
C22 C23 H23 105.9 . . ?
C25 C23 H23 105.9 . . ?
C6 C23 H23 105.9 . . ?
O6 C24 N1 124.0(2) . . ?
O6 C24 C25 127.45(19) . . ?
N1 C24 C25 108.55(18) . . ?
C26 C25 C24 101.36(16) . . ?
C26 C25 C23 112.85(16) . . ?
C24 C25 C23 114.53(17) . . ?
C26 C25 C40 110.38(16) . . ?
C24 C25 C40 110.79(16) . . ?
C23 C25 C40 106.94(16) . . ?
C27 C26 C31 120.1(2) . . ?
C27 C26 C25 131.1(2) . . ?
C31 C26 C25 108.76(19) . . ?
C26 C27 C28 117.7(2) . . ?
C26 C27 H27 121.1 . . ?
C28 C27 H27 121.1 . . ?
C29 C28 C27 122.3(2) . . ?
C29 C28 Cl1 118.99(18) . . ?
C27 C28 Cl1 118.7(2) . . ?
C28 C29 C30 120.2(2) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C31 117.9(2) . . ?
C29 C30 H30 121.0 . . ?
C31 C30 H30 121.0 . . ?
C30 C31 N1 128.5(2) . . ?
C30 C31 C26 121.8(2) . . ?
N1 C31 C26 109.72(18) . . ?
N1 C32 C33 113.5(2) . . ?
N1 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
N1 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C38 C33 C34 118.1(3) . . ?
C38 C33 C32 120.7(2) . . ?
C34 C33 C32 121.3(2) . . ?
C35 C34 C33 120.8(3) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C37 C36 C35 119.5(3) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C38 120.4(3) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C37 C38 C33 120.9(3) . . ?
C37 C38 H38 119.6 . . ?
C33 C38 H38 119.6 . . ?
C4 C39 C40 124.75(19) . . ?
C4 C39 H39 117.6 . . ?
C40 C39 H39 117.6 . . ?
O7 C40 C39 110.72(16) . . ?
O7 C40 C41 110.26(17) . . ?
C39 C40 C41 110.55(17) . . ?
O7 C40 C25 104.98(16) . . ?
C39 C40 C25 108.20(16) . . ?
C41 C40 C25 111.99(16) . . ?
C46 C41 C42 118.3(2) . . ?
C46 C41 C40 121.11(19) . . ?
C42 C41 C40 120.6(2) . . ?
C43 C42 C41 121.1(2) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C44 C43 C42 118.9(2) . . ?
C44 C43 H43 120.6 . . ?
C42 C43 H43 120.6 . . ?
C43 C44 C45 121.8(2) . . ?
C43 C44 Cl3 119.6(2) . . ?
C45 C44 Cl3 118.6(2) . . ?
C44 C45 C46 118.7(3) . . ?
C44 C45 H45 120.7 . . ?
C46 C45 H45 120.7 . . ?
C45 C46 C41 121.3(2) . . ?
C45 C46 H46 119.4 . . ?
C41 C46 H46 119.4 . . ?
O8 C47 N3 129.6(5) . . ?
O8 C47 H47 115.2 . . ?
N3 C47 H47 115.2 . . ?
N3 C48 H48A 109.5 . . ?
N3 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
N3 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N3 C49 H49A 109.5 . . ?
N3 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
N3 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C24 N1 C31 111.40(18) . . ?
C24 N1 C32 121.6(2) . . ?
C31 N1 C32 126.86(19) . . ?
C5 N2 C12 111.42(18) . . ?
C5 N2 C13 123.8(2) . . ?
C12 N2 C13 124.8(2) . . ?
C47 N3 C48 130.0(5) . . ?
C47 N3 C49 115.7(4) . . ?
C48 N3 C49 114.2(4) . . ?
C3 O1 C2 115.5(2) . . ?
C22 O4 C21 117.5(2) . . ?
C40 O7 H7 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O8 0.82 1.88 2.701(3) 174.3 2_766

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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/cc13k6kf
_database_code_depnum_ccdc_archive 'CCDC 1029434'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H38 N2 O8'
_chemical_formula_weight         686.73

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                   10.740(3)
_cell_length_b                   12.889(3)
_cell_length_c                   15.381(4)
_cell_angle_alpha                68.745(3)
_cell_angle_beta                 87.060(3)
_cell_angle_gamma                70.391(3)
_cell_volume                     1863.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6645
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             724
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_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            12005
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6557
_reflns_number_gt                5152
_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)+(0.1700P)²+0.9000P] 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         6287
_refine_ls_number_parameters     463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_ref         0.2499
_refine_ls_wR_factor_gt          0.2365
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.5141(4) 0.8104(3) 0.2244(2) 0.0618(9) Uani 1 1 d . . .
H1 H 0.5080 0.7616 0.1939 0.074 Uiso 1 1 calc R . .
C2 C 0.4764(5) 0.9314(4) 0.1758(3) 0.0810(13) Uani 1 1 d . . .
H2 H 0.4457 0.9632 0.1130 0.097 Uiso 1 1 calc R . .
C3 C 0.4843(5) 1.0049(3) 0.2205(3) 0.0779(12) Uani 1 1 d . . .
H3 H 0.4572 1.0864 0.1885 0.093 Uiso 1 1 calc R . .
C4 C 0.5330(4) 0.9559(3) 0.3134(3) 0.0671(10) Uani 1 1 d . . .
H4 H 0.5401 1.0047 0.3436 0.081 Uiso 1 1 calc R . .
C5 C 0.5706(4) 0.8367(3) 0.3611(2) 0.0550(8) Uani 1 1 d . . .
H5 H 0.6033 0.8051 0.4235 0.066 Uiso 1 1 calc R . .
C6 C 0.5606(3) 0.7612(2) 0.3174(2) 0.0425(6) Uani 1 1 d . . .
C7 C 0.5972(4) 0.6310(3) 0.3756(2) 0.0503(7) Uani 1 1 d . . .
H7A H 0.6912 0.5990 0.3951 0.060 Uiso 1 1 calc R . .
H7B H 0.5494 0.6218 0.4315 0.060 Uiso 1 1 calc R . .
C8 C 0.4558(3) 0.5353(2) 0.33561(17) 0.0345(6) Uani 1 1 d . . .
C9 C 0.4624(2) 0.4549(2) 0.27965(16) 0.0290(5) Uani 1 1 d . . .
C10 C 0.6005(2) 0.4394(2) 0.24443(17) 0.0323(5) Uani 1 1 d . . .
C11 C 0.6761(3) 0.3685(3) 0.1967(2) 0.0425(6) Uani 1 1 d . . .
H11 H 0.6415 0.3215 0.1788 0.051 Uiso 1 1 calc R . .
C12 C 0.8030(3) 0.3695(3) 0.1766(2) 0.0571(8) Uani 1 1 d . . .
H12 H 0.8532 0.3241 0.1437 0.069 Uiso 1 1 calc R . .
C13 C 0.8563(3) 0.4381(3) 0.2053(3) 0.0612(9) Uani 1 1 d . . .
H13 H 0.9418 0.4375 0.1915 0.073 Uiso 1 1 calc R . .
C14 C 0.7837(3) 0.5068(3) 0.2539(3) 0.0558(8) Uani 1 1 d . . .
H14 H 0.8189 0.5528 0.2728 0.067 Uiso 1 1 calc R . .
C15 C 0.6561(3) 0.5052(2) 0.27383(18) 0.0383(6) Uani 1 1 d . . .
C16 C 0.4404(2) 0.3384(2) 0.33993(16) 0.0297(5) Uani 1 1 d . . .
H16 H 0.3711 0.3566 0.3815 0.036 Uiso 1 1 calc R . .
C17 C 0.5628(2) 0.2462(2) 0.40021(17) 0.0338(5) Uani 1 1 d . . .
C18 C 0.7195(3) 0.2120(3) 0.5223(2) 0.0530(8) Uani 1 1 d . . .
H18A H 0.7153 0.2371 0.5750 0.064 Uiso 1 1 calc R . .
H18B H 0.7199 0.1311 0.5459 0.064 Uiso 1 1 calc R . .
C19 C 0.8410(5) 0.2164(8) 0.4774(4) 0.146(3) Uani 1 1 d . . .
H19A H 0.8463 0.1897 0.4262 0.219 Uiso 1 1 calc R . .
H19B H 0.9159 0.1661 0.5220 0.219 Uiso 1 1 calc R . .
H19C H 0.8410 0.2963 0.4544 0.219 Uiso 1 1 calc R . .
C20 C -0.1051(4) 0.9172(4) 0.2532(3) 0.0688(10) Uani 1 1 d . . .
H20 H -0.1786 0.8957 0.2494 0.083 Uiso 1 1 calc R . .
C21 C -0.1202(6) 1.0140(4) 0.2763(4) 0.0991(18) Uani 1 1 d . . .
H21 H -0.2033 1.0566 0.2889 0.119 Uiso 1 1 calc R . .
C22 C -0.0120(6) 1.0486(4) 0.2810(3) 0.0902(15) Uani 1 1 d . . .
H22 H -0.0226 1.1157 0.2945 0.108 Uiso 1 1 calc R . .
C23 C 0.1108(5) 0.9821(4) 0.2655(3) 0.0754(11) Uani 1 1 d . . .
H23 H 0.1839 1.0044 0.2685 0.090 Uiso 1 1 calc R . .
C24 C 0.1267(4) 0.8820(3) 0.2453(2) 0.0590(8) Uani 1 1 d . . .
H24 H 0.2111 0.8353 0.2385 0.071 Uiso 1 1 calc R . .
C25 C 0.0181(3) 0.8510(3) 0.23523(19) 0.0476(7) Uani 1 1 d . . .
C26 C 0.0255(3) 0.7491(3) 0.2059(3) 0.0561(8) Uani 1 1 d . . .
H26A H -0.0130 0.6974 0.2528 0.067 Uiso 1 1 calc R . .
H26B H -0.0291 0.7808 0.1476 0.067 Uiso 1 1 calc R . .
C27 C 0.2097(2) 0.5591(2) 0.23989(18) 0.0369(6) Uani 1 1 d . . .
C28 C 0.3461(2) 0.5130(2) 0.20047(16) 0.0305(5) Uani 1 1 d . . .
C29 C 0.3480(3) 0.6224(2) 0.12034(17) 0.0355(6) Uani 1 1 d . . .
C30 C 0.4378(3) 0.6411(3) 0.05372(18) 0.0432(6) Uani 1 1 d . . .
H30 H 0.5144 0.5792 0.0548 0.052 Uiso 1 1 calc R . .
C31 C 0.4130(4) 0.7537(3) -0.0153(2) 0.0588(9) Uani 1 1 d . . .
H31 H 0.4736 0.7671 -0.0597 0.071 Uiso 1 1 calc R . .
C32 C 0.2975(4) 0.8455(3) -0.0174(2) 0.0700(11) Uani 1 1 d . . .
H32 H 0.2808 0.9197 -0.0642 0.084 Uiso 1 1 calc R . .
C33 C 0.2061(4) 0.8284(3) 0.0496(2) 0.0596(9) Uani 1 1 d . . .
H33 H 0.1293 0.8903 0.0483 0.072 Uiso 1 1 calc R . .
C34 C 0.2332(3) 0.7175(2) 0.11745(19) 0.0418(6) Uani 1 1 d . . .
C35 C 0.3537(2) 0.4048(2) 0.17589(17) 0.0316(5) Uani 1 1 d . . .
H35 H 0.4319 0.3897 0.1405 0.038 Uiso 1 1 calc R . .
C36 C 0.2362(3) 0.4236(2) 0.11384(18) 0.0379(6) Uani 1 1 d . . .
C37 C 0.1586(4) 0.3338(4) 0.0280(3) 0.0724(11) Uani 1 1 d . . .
H37A H 0.0833 0.3348 0.0657 0.087 Uiso 1 1 calc R . .
H37B H 0.1309 0.4022 -0.0300 0.087 Uiso 1 1 calc R . .
C38 C 0.2042(8) 0.2269(7) 0.0084(6) 0.162(4) Uani 1 1 d . . .
H38A H 0.2932 0.2136 -0.0102 0.243 Uiso 1 1 calc R . .
H38B H 0.1473 0.2343 -0.0413 0.243 Uiso 1 1 calc R . .
H38C H 0.2025 0.1614 0.0635 0.243 Uiso 1 1 calc R . .
C39 C 0.3855(2) 0.2985(2) 0.27114(17) 0.0321(5) Uani 1 1 d . . .
H39 H 0.4576 0.2327 0.2631 0.038 Uiso 1 1 calc R . .
C40 C 0.2730(3) 0.2536(2) 0.30885(19) 0.0394(6) Uani 1 1 d . . .
C41 C 0.1969(5) 0.1437(4) 0.4470(3) 0.0770(11) Uani 1 1 d . . .
H41A H 0.1169 0.2055 0.4481 0.115 Uiso 1 1 calc R . .
H41B H 0.2303 0.0912 0.5100 0.115 Uiso 1 1 calc R . .
H41C H 0.1783 0.1003 0.4131 0.115 Uiso 1 1 calc R . .
N1 N 0.5683(2) 0.5618(2) 0.32646(16) 0.0402(5) Uani 1 1 d . . .
N2 N 0.1572(2) 0.6778(2) 0.19289(16) 0.0428(6) Uani 1 1 d . . .
O1 O 0.3639(2) 0.5688(2) 0.38042(15) 0.0519(6) Uani 1 1 d . . .
O2 O 0.6170(2) 0.14869(18) 0.39860(17) 0.0559(6) Uani 1 1 d . . .
O3 O 0.6025(2) 0.28864(17) 0.45659(14) 0.0457(5) Uani 1 1 d . . .
O4 O 0.15962(19) 0.49884(19) 0.30110(14) 0.0470(5) Uani 1 1 d . . .
O5 O 0.1340(2) 0.5053(2) 0.09622(17) 0.0567(6) Uani 1 1 d . . .
O6 O 0.2670(2) 0.3383(2) 0.07822(14) 0.0495(5) Uani 1 1 d . . .
O7 O 0.1800(2) 0.2609(2) 0.26331(17) 0.0616(6) Uani 1 1 d . . .
O8 O 0.2934(2) 0.1943(2) 0.40235(15) 0.0548(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.379(5) . ?
C1 C2 1.384(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(4) . ?
C7 N1 1.470(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.223(3) . ?
C8 N1 1.349(4) . ?
C8 C9 1.553(3) . ?
C9 C10 1.527(3) . ?
C9 C16 1.541(3) . ?
C9 C28 1.572(3) . ?
C10 C15 1.388(4) . ?
C10 C11 1.399(4) . ?
C11 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(4) . ?
C14 H14 0.9300 . ?
C15 N1 1.402(4) . ?
C16 C17 1.509(3) . ?
C16 C39 1.547(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.204(3) . ?
C17 O3 1.331(3) . ?
C18 C19 1.452(6) . ?
C18 O3 1.466(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.375(6) . ?
C20 C25 1.389(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.391(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.388(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.387(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.513(4) . ?
C26 N2 1.455(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 O4 1.216(3) . ?
C27 N2 1.358(4) . ?
C27 C28 1.566(3) . ?
C28 C29 1.505(4) . ?
C28 C35 1.548(3) . ?
C29 C30 1.384(4) . ?
C29 C34 1.406(4) . ?
C30 C31 1.398(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.389(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.396(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.374(4) . ?
C33 H33 0.9300 . ?
C34 N2 1.423(4) . ?
C35 C36 1.520(3) . ?
C35 C39 1.556(3) . ?
C35 H35 0.9800 . ?
C36 O5 1.198(3) . ?
C36 O6 1.339(3) . ?
C37 C38 1.436(8) . ?
C37 O6 1.458(4) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.512(4) . ?
C39 H39 0.9800 . ?
C40 O7 1.208(3) . ?
C40 O8 1.350(3) . ?
C41 O8 1.424(4) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 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 120.9(3) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 123.6(2) . . ?
C5 C6 C7 118.2(3) . . ?
N1 C7 C6 113.9(2) . . ?
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 125.9(2) . . ?
O1 C8 C9 125.5(2) . . ?
N1 C8 C9 108.6(2) . . ?
C10 C9 C16 114.56(19) . . ?
C10 C9 C8 101.08(19) . . ?
C16 C9 C8 112.65(19) . . ?
C10 C9 C28 114.71(19) . . ?
C16 C9 C28 102.36(19) . . ?
C8 C9 C28 111.94(19) . . ?
C15 C10 C11 119.4(2) . . ?
C15 C10 C9 108.5(2) . . ?
C11 C10 C9 132.0(2) . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 118.1(3) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C10 C15 C14 121.9(3) . . ?
C10 C15 N1 110.2(2) . . ?
C14 C15 N1 127.9(3) . . ?
C17 C16 C9 113.1(2) . . ?
C17 C16 C39 114.10(19) . . ?
C9 C16 C39 105.96(19) . . ?
C17 C16 H16 107.8 . . ?
C9 C16 H16 107.8 . . ?
C39 C16 H16 107.8 . . ?
O2 C17 O3 124.5(2) . . ?
O2 C17 C16 125.8(2) . . ?
O3 C17 C16 109.6(2) . . ?
C19 C18 O3 111.2(3) . . ?
C19 C18 H18A 109.4 . . ?
O3 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
O3 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
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 C25 121.1(4) . . ?
C21 C20 H20 119.5 . . ?
C25 C20 H20 119.5 . . ?
C20 C21 C22 120.4(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.0(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 120.6(5) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C20 118.2(3) . . ?
C24 C25 C26 123.9(3) . . ?
C20 C25 C26 117.9(3) . . ?
N2 C26 C25 116.2(3) . . ?
N2 C26 H26A 108.2 . . ?
C25 C26 H26A 108.2 . . ?
N2 C26 H26B 108.2 . . ?
C25 C26 H26B 108.2 . . ?
H26A C26 H26B 107.4 . . ?
O4 C27 N2 126.3(2) . . ?
O4 C27 C28 125.9(2) . . ?
N2 C27 C28 107.8(2) . . ?
C29 C28 C35 116.67(19) . . ?
C29 C28 C27 102.01(19) . . ?
C35 C28 C27 110.1(2) . . ?
C29 C28 C9 116.7(2) . . ?
C35 C28 C9 100.71(18) . . ?
C27 C28 C9 110.77(18) . . ?
C30 C29 C34 119.2(3) . . ?
C30 C29 C28 131.8(2) . . ?
C34 C29 C28 109.0(2) . . ?
C29 C30 C31 119.7(3) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C32 C31 C30 119.9(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 121.3(3) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C32 118.0(3) . . ?
C34 C33 H33 121.0 . . ?
C32 C33 H33 121.0 . . ?
C33 C34 C29 122.1(3) . . ?
C33 C34 N2 128.8(3) . . ?
C29 C34 N2 109.2(2) . . ?
C36 C35 C28 114.8(2) . . ?
C36 C35 C39 116.7(2) . . ?
C28 C35 C39 105.24(18) . . ?
C36 C35 H35 106.5 . . ?
C28 C35 H35 106.5 . . ?
C39 C35 H35 106.5 . . ?
O5 C36 O6 125.2(2) . . ?
O5 C36 C35 125.1(2) . . ?
O6 C36 C35 109.6(2) . . ?
C38 C37 O6 108.4(4) . . ?
C38 C37 H37A 110.0 . . ?
O6 C37 H37A 110.0 . . ?
C38 C37 H37B 110.0 . . ?
O6 C37 H37B 110.0 . . ?
H37A C37 H37B 108.4 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C16 112.2(2) . . ?
C40 C39 C35 116.3(2) . . ?
C16 C39 C35 105.54(19) . . ?
C40 C39 H39 107.5 . . ?
C16 C39 H39 107.5 . . ?
C35 C39 H39 107.5 . . ?
O7 C40 O8 122.4(3) . . ?
O7 C40 C39 126.4(3) . . ?
O8 C40 C39 111.1(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 . . ?
C8 N1 C15 111.6(2) . . ?
C8 N1 C7 122.4(2) . . ?
C15 N1 C7 125.6(2) . . ?
C27 N2 C34 111.5(2) . . ?
C27 N2 C26 123.0(3) . . ?
C34 N2 C26 124.2(3) . . ?
C17 O3 C18 118.4(2) . . ?
C36 O6 C37 116.3(2) . . ?
C40 O8 C41 117.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.093



loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.500 102 23 ' '
_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/. 
# 
# Audit and citation data items have may 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_4d
_audit_block_doi                 10.5517/cc13l7tr
_database_code_depnum_ccdc_archive 'CCDC 1030434'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H36 Cl2 N2 O8'
_chemical_formula_sum            'C41 H36 Cl2 N2 O8'
_chemical_formula_weight         755.62

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                   10.8295(16)
_cell_length_b                   12.8333(19)
_cell_length_c                   15.121(2)
_cell_angle_alpha                85.481(2)
_cell_angle_beta                 76.954(2)
_cell_angle_gamma                75.004(2)
_cell_volume                     1977.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5412
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             788
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.958
_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            13843
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         26.00
_reflns_number_total             7783
_reflns_number_gt                5299
_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_number_reflns         7409
_refine_ls_number_parameters     481
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.1064
_refine_ls_wR_factor_ref         0.3093
_refine_ls_wR_factor_gt          0.2890
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_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 0.4997(5) 1.2522(4) 0.6970(5) 0.0919(19) Uani 1 1 d . . .
H1 H 0.5898 1.2298 0.6760 0.110 Uiso 1 1 calc R . .
C2 C 0.4402(7) 1.3595(4) 0.7085(8) 0.148(4) Uani 1 1 d . . .
H2 H 0.4904 1.4099 0.6957 0.178 Uiso 1 1 calc R . .
C3 C 0.3075(6) 1.3936(4) 0.7387(6) 0.107(2) Uani 1 1 d . . .
H3 H 0.2679 1.4670 0.7442 0.129 Uiso 1 1 calc R . .
C4 C 0.2345(5) 1.3224(4) 0.7601(3) 0.0722(13) Uani 1 1 d . . .
H4 H 0.1449 1.3455 0.7829 0.087 Uiso 1 1 calc R . .
C5 C 0.2935(4) 1.2138(3) 0.7482(3) 0.0694(13) Uani 1 1 d . . .
H5 H 0.2423 1.1643 0.7620 0.083 Uiso 1 1 calc R . .
C6 C 0.4260(4) 1.1774(3) 0.7166(2) 0.0471(8) Uani 1 1 d . . .
C7 C 0.4968(4) 1.0596(3) 0.7035(3) 0.0554(10) Uani 1 1 d . . .
H7A H 0.5643 1.0533 0.6484 0.066 Uiso 1 1 calc R . .
H7B H 0.5396 1.0346 0.7538 0.066 Uiso 1 1 calc R . .
C8 C 0.3446(3) 0.9932(2) 0.6284(2) 0.0388(7) Uani 1 1 d . . .
C9 C 0.3304(4) 1.0679(3) 0.5574(3) 0.0532(9) Uani 1 1 d . . .
H9 H 0.3656 1.1274 0.5531 0.064 Uiso 1 1 calc R . .
C10 C 0.2657(4) 1.0537(3) 0.4951(3) 0.0626(12) Uani 1 1 d . . .
H10 H 0.2549 1.1042 0.4481 0.075 Uiso 1 1 calc R . .
C11 C 0.2140(3) 0.9624(3) 0.5007(2) 0.0522(9) Uani 1 1 d . . .
C12 C 0.2277(3) 0.8858(3) 0.5714(2) 0.0424(8) Uani 1 1 d . . .
H12 H 0.1942 0.8254 0.5748 0.051 Uiso 1 1 calc R . .
C13 C 0.2921(3) 0.9024(2) 0.63532(19) 0.0339(7) Uani 1 1 d . . .
C14 C 0.3265(3) 0.8361(2) 0.71732(19) 0.0324(6) Uani 1 1 d . . .
C15 C 0.4154(3) 0.8963(2) 0.7484(2) 0.0375(7) Uani 1 1 d . . .
C16 C 0.3985(3) 0.7162(2) 0.6991(2) 0.0350(7) Uani 1 1 d . . .
H16 H 0.3428 0.6862 0.6705 0.042 Uiso 1 1 calc R . .
C17 C 0.5294(3) 0.6984(3) 0.6338(2) 0.0398(7) Uani 1 1 d . . .
C18 C 0.6875(4) 0.5698(4) 0.5330(3) 0.0759(14) Uani 1 1 d . . .
H18A H 0.7585 0.5725 0.5614 0.091 Uiso 1 1 calc R . .
H18B H 0.6877 0.6199 0.4815 0.091 Uiso 1 1 calc R . .
C19 C 0.7048(5) 0.4591(5) 0.5026(4) 0.0986(19) Uani 1 1 d . . .
H19A H 0.6987 0.4110 0.5545 0.148 Uiso 1 1 calc R . .
H19B H 0.7892 0.4361 0.4630 0.148 Uiso 1 1 calc R . .
H19C H 0.6379 0.4584 0.4707 0.148 Uiso 1 1 calc R . .
C20 C -0.0438(6) 1.1693(4) 0.7474(4) 0.0785(14) Uani 1 1 d . . .
H20 H 0.0294 1.1159 0.7225 0.094 Uiso 1 1 calc R . .
C21 C -0.0722(9) 1.2691(6) 0.7028(6) 0.126(3) Uani 1 1 d . . .
H21 H -0.0157 1.2856 0.6506 0.151 Uiso 1 1 calc R . .
C22 C -0.1904(10) 1.3447(4) 0.7399(8) 0.132(3) Uani 1 1 d . . .
H22 H -0.2132 1.4109 0.7103 0.158 Uiso 1 1 calc R . .
C23 C -0.2716(9) 1.3221(6) 0.8184(7) 0.129(3) Uani 1 1 d . . .
H23 H -0.3489 1.3721 0.8423 0.155 Uiso 1 1 calc R . .
C24 C -0.2366(6) 1.2250(4) 0.8607(5) 0.0910(17) Uani 1 1 d . . .
H24 H -0.2914 1.2089 0.9139 0.109 Uiso 1 1 calc R . .
C25 C -0.1229(4) 1.1498(3) 0.8271(3) 0.0583(10) Uani 1 1 d . . .
C26 C -0.0874(4) 1.0500(3) 0.8828(3) 0.0543(9) Uani 1 1 d . . .
H26A H -0.0564 1.0685 0.9335 0.065 Uiso 1 1 calc R . .
H26B H -0.1662 1.0258 0.9078 0.065 Uiso 1 1 calc R . .
C27 C -0.0171(3) 0.8789(3) 0.7915(2) 0.0378(7) Uani 1 1 d . . .
C28 C -0.1360(3) 0.8748(3) 0.7757(3) 0.0507(9) Uani 1 1 d . . .
H28 H -0.2092 0.9320 0.7911 0.061 Uiso 1 1 calc R . .
C29 C -0.1445(3) 0.7838(4) 0.7363(3) 0.0573(10) Uani 1 1 d . . .
H29 H -0.2237 0.7792 0.7249 0.069 Uiso 1 1 calc R . .
C30 C -0.0329(4) 0.6989(3) 0.7140(3) 0.0533(9) Uani 1 1 d . . .
C31 C 0.0870(3) 0.7050(3) 0.7301(2) 0.0414(7) Uani 1 1 d . . .
H31 H 0.1603 0.6475 0.7159 0.050 Uiso 1 1 calc R . .
C32 C 0.0960(3) 0.7958(2) 0.76675(18) 0.0315(6) Uani 1 1 d . . .
C33 C 0.2083(3) 0.8241(2) 0.79655(18) 0.0309(6) Uani 1 1 d . . .
C34 C 0.1386(3) 0.9327(2) 0.84553(19) 0.0369(7) Uani 1 1 d . . .
C35 C 0.2783(3) 0.7385(2) 0.85891(19) 0.0333(6) Uani 1 1 d . . .
H35 H 0.3155 0.7755 0.8967 0.040 Uiso 1 1 calc R . .
C36 C 0.1876(3) 0.6788(3) 0.9214(2) 0.0428(8) Uani 1 1 d . . .
C37 C -0.0124(5) 0.7058(5) 1.0341(3) 0.0782(14) Uani 1 1 d . . .
H37A H 0.0299 0.6383 1.0604 0.094 Uiso 1 1 calc R . .
H37B H -0.0556 0.7558 1.0831 0.094 Uiso 1 1 calc R . .
C38 C -0.1056(8) 0.6881(9) 0.9903(4) 0.153(4) Uani 1 1 d . . .
H38A H -0.1202 0.7428 0.9441 0.230 Uiso 1 1 calc R . .
H38B H -0.1862 0.6908 1.0336 0.230 Uiso 1 1 calc R . .
H38C H -0.0745 0.6184 0.9631 0.230 Uiso 1 1 calc R . .
C39 C 0.3927(3) 0.6629(2) 0.7949(2) 0.0359(7) Uani 1 1 d . . .
H39 H 0.3687 0.5946 0.7933 0.043 Uiso 1 1 calc R . .
C40 C 0.5196(3) 0.6374(3) 0.8283(3) 0.0471(8) Uani 1 1 d . . .
C41 C 0.6146(6) 0.6099(6) 0.9567(4) 0.107(2) Uani 1 1 d . . .
H41A H 0.6765 0.5477 0.9279 0.161 Uiso 1 1 calc R . .
H41B H 0.5897 0.5949 1.0205 0.161 Uiso 1 1 calc R . .
H41C H 0.6537 0.6701 0.9477 0.161 Uiso 1 1 calc R . .
Cl1 Cl 0.13983(12) 0.93940(12) 0.41649(7) 0.0780(4) Uani 1 1 d . . .
Cl2 Cl -0.04269(13) 0.58224(13) 0.66790(13) 0.1018(6) Uani 1 1 d . . .
N1 N 0.4131(3) 0.9901(2) 0.69757(19) 0.0431(7) Uani 1 1 d . . .
N2 N 0.0118(3) 0.9598(2) 0.83590(18) 0.0431(7) Uani 1 1 d . . .
O1 O 0.4779(2) 0.8665(2) 0.80766(17) 0.0506(6) Uani 1 1 d . . .
O2 O 0.5901(3) 0.7645(2) 0.6098(2) 0.0641(8) Uani 1 1 d . . .
O3 O 0.5611(2) 0.5996(2) 0.59880(18) 0.0562(7) Uani 1 1 d . . .
O4 O 0.1880(3) 0.9846(2) 0.88387(17) 0.0539(7) Uani 1 1 d . . .
O5 O 0.2039(3) 0.5832(2) 0.9264(2) 0.0700(9) Uani 1 1 d . . .
O6 O 0.0875(2) 0.7503(2) 0.97050(16) 0.0519(6) Uani 1 1 d . . .
O7 O 0.6285(3) 0.6164(3) 0.7769(2) 0.0714(9) Uani 1 1 d . . .
O8 O 0.5001(3) 0.6354(3) 0.9175(2) 0.0661(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 C2 1.368(8) . ?
C1 C6 1.375(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.333(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.514(5) . ?
C7 N1 1.447(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.390(5) . ?
C8 N1 1.404(5) . ?
C8 C13 1.411(4) . ?
C9 C10 1.343(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.414(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.400(5) . ?
C11 Cl1 1.731(4) . ?
C12 C13 1.371(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.509(4) . ?
C14 C15 1.548(5) . ?
C14 C16 1.550(4) . ?
C14 C33 1.574(4) . ?
C15 O1 1.222(4) . ?
C15 N1 1.374(4) . ?
C16 C17 1.507(4) . ?
C16 C39 1.549(4) . ?
C16 H16 0.9800 . ?
C17 O2 1.189(4) . ?
C17 O3 1.344(4) . ?
C18 O3 1.478(4) . ?
C18 C19 1.480(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.359(7) . ?
C20 C21 1.395(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.419(13) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.358(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.490(6) . ?
C26 N2 1.463(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.376(5) . ?
C27 C32 1.399(4) . ?
C27 N2 1.414(5) . ?
C28 C29 1.384(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.398(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.397(5) . ?
C30 Cl2 1.737(4) . ?
C31 C32 1.363(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.522(4) . ?
C33 C35 1.549(4) . ?
C33 C34 1.558(4) . ?
C34 O4 1.205(4) . ?
C34 N2 1.365(4) . ?
C35 C36 1.517(4) . ?
C35 C39 1.549(4) . ?
C35 H35 0.9800 . ?
C36 O5 1.192(4) . ?
C36 O6 1.341(4) . ?
C37 C38 1.399(9) . ?
C37 O6 1.478(4) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.517(5) . ?
C39 H39 0.9800 . ?
C40 O7 1.234(4) . ?
C40 O8 1.316(5) . ?
C41 O8 1.445(6) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 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 119.9(5) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C1 C2 C3 120.6(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.3(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 118.2(4) . . ?
C5 C6 C7 124.1(3) . . ?
C1 C6 C7 117.7(4) . . ?
N1 C7 C6 114.2(3) . . ?
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 . . ?
C9 C8 N1 128.8(3) . . ?
C9 C8 C13 120.5(3) . . ?
N1 C8 C13 110.6(3) . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 Cl1 118.6(3) . . ?
C10 C11 Cl1 120.3(3) . . ?
C13 C12 C11 118.0(3) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C8 120.5(3) . . ?
C12 C13 C14 131.7(3) . . ?
C8 C13 C14 107.8(3) . . ?
C13 C14 C15 102.3(2) . . ?
C13 C14 C16 115.3(2) . . ?
C15 C14 C16 110.7(2) . . ?
C13 C14 C33 116.4(2) . . ?
C15 C14 C33 111.4(2) . . ?
C16 C14 C33 101.0(2) . . ?
O1 C15 N1 125.2(3) . . ?
O1 C15 C14 126.5(3) . . ?
N1 C15 C14 108.3(3) . . ?
C17 C16 C39 118.3(3) . . ?
C17 C16 C14 114.8(2) . . ?
C39 C16 C14 104.2(2) . . ?
C17 C16 H16 106.2 . . ?
C39 C16 H16 106.2 . . ?
C14 C16 H16 106.2 . . ?
O2 C17 O3 124.5(3) . . ?
O2 C17 C16 125.7(3) . . ?
O3 C17 C16 109.4(3) . . ?
O3 C18 C19 108.0(4) . . ?
O3 C18 H18A 110.1 . . ?
C19 C18 H18A 110.1 . . ?
O3 C18 H18B 110.1 . . ?
C19 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
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 . . ?
C25 C20 C21 120.2(6) . . ?
C25 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 117.6(7) . . ?
C20 C21 H21 121.2 . . ?
C22 C21 H21 121.2 . . ?
C23 C22 C21 121.3(5) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 118.5(7) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C23 C24 C25 122.0(7) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
C20 C25 C24 120.3(5) . . ?
C20 C25 C26 121.9(4) . . ?
C24 C25 C26 117.8(5) . . ?
N2 C26 C25 116.3(3) . . ?
N2 C26 H26A 108.2 . . ?
C25 C26 H26A 108.2 . . ?
N2 C26 H26B 108.2 . . ?
C25 C26 H26B 108.2 . . ?
H26A C26 H26B 107.4 . . ?
C28 C27 C32 122.3(3) . . ?
C28 C27 N2 128.2(3) . . ?
C32 C27 N2 109.5(3) . . ?
C27 C28 C29 118.7(3) . . ?
C27 C28 H28 120.7 . . ?
C29 C28 H28 120.7 . . ?
C28 C29 C30 119.5(3) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C31 C30 C29 120.9(4) . . ?
C31 C30 Cl2 118.9(3) . . ?
C29 C30 Cl2 120.1(3) . . ?
C32 C31 C30 119.6(3) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C27 119.0(3) . . ?
C31 C32 C33 131.9(3) . . ?
C27 C32 C33 108.8(3) . . ?
C32 C33 C35 115.0(2) . . ?
C32 C33 C34 101.8(2) . . ?
C35 C33 C34 112.2(2) . . ?
C32 C33 C14 115.0(2) . . ?
C35 C33 C14 101.4(2) . . ?
C34 C33 C14 111.9(2) . . ?
O4 C34 N2 126.0(3) . . ?
O4 C34 C33 126.2(3) . . ?
N2 C34 C33 107.8(3) . . ?
C36 C35 C33 113.4(2) . . ?
C36 C35 C39 113.1(3) . . ?
C33 C35 C39 106.0(2) . . ?
C36 C35 H35 108.1 . . ?
C33 C35 H35 108.1 . . ?
C39 C35 H35 108.1 . . ?
O5 C36 O6 125.6(3) . . ?
O5 C36 C35 125.1(3) . . ?
O6 C36 C35 109.2(3) . . ?
C38 C37 O6 111.3(4) . . ?
C38 C37 H37A 109.4 . . ?
O6 C37 H37A 109.4 . . ?
C38 C37 H37B 109.4 . . ?
O6 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C16 115.5(2) . . ?
C40 C39 C35 112.8(3) . . ?
C16 C39 C35 106.0(2) . . ?
C40 C39 H39 107.4 . . ?
C16 C39 H39 107.4 . . ?
C35 C39 H39 107.4 . . ?
O7 C40 O8 124.2(3) . . ?
O7 C40 C39 123.1(3) . . ?
O8 C40 C39 112.6(3) . . ?
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 . . ?
C15 N1 C8 110.4(3) . . ?
C15 N1 C7 122.0(3) . . ?
C8 N1 C7 126.0(3) . . ?
C34 N2 C27 111.9(2) . . ?
C34 N2 C26 123.0(3) . . ?
C27 N2 C26 123.9(3) . . ?
C17 O3 C18 116.0(3) . . ?
C36 O6 C37 116.5(3) . . ?
C40 O8 C41 117.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.121


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 0.033 0.253 0.490 21 1 ' '
2 -0.033 0.747 0.510 21 1 ' '
3 0.500 0.000 0.000 119 24 ' '
_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/. 
# 
# Audit and citation data items have may 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_4f
_audit_block_doi                 10.5517/cc13sx71
_database_code_depnum_ccdc_archive 'CCDC 1036833'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H38 F2 N2 O8'
_chemical_formula_sum            'C42 H38 F2 N2 O8'
_chemical_formula_weight         736.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   10.5612(11)
_cell_length_b                   12.8164(13)
_cell_length_c                   15.0804(16)
_cell_angle_alpha                85.716(3)
_cell_angle_beta                 77.587(3)
_cell_angle_gamma                76.529(3)
_cell_volume                     1938.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_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            25423
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.59
_reflns_number_total             8762
_reflns_number_gt                5523
_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)+(0.1466P)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       0.076(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8762
_refine_ls_number_parameters     491
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.2364
_refine_ls_wR_factor_gt          0.2154
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.100
_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 0.4765(3) 1.1506(2) 0.2155(2) 0.0842(9) Uani 1 1 d . . .
H1 H 0.5374 1.0869 0.1924 0.101 Uiso 1 1 calc R . .
C2 C 0.4658(5) 1.2425(3) 0.1608(3) 0.1152(13) Uani 1 1 d . . .
H2 H 0.5166 1.2418 0.1005 0.138 Uiso 1 1 calc R . .
C3 C 0.3786(6) 1.3362(3) 0.1961(4) 0.1208(16) Uani 1 1 d . . .
H3 H 0.3714 1.4010 0.1608 0.145 Uiso 1 1 calc R . .
C4 C 0.3063(6) 1.3341(3) 0.2790(5) 0.139(2) Uani 1 1 d . . .
H4 H 0.2463 1.3981 0.3023 0.167 Uiso 1 1 calc R . .
C5 C 0.3154(4) 1.2413(3) 0.3331(3) 0.1104(13) Uani 1 1 d . . .
H5 H 0.2612 1.2420 0.3923 0.132 Uiso 1 1 calc R . .
C6 C 0.4028(3) 1.14843(19) 0.3010(2) 0.0629(7) Uani 1 1 d . . .
C7 C 0.4159(3) 1.0512(2) 0.36405(18) 0.0644(7) Uani 1 1 d . . .
H7A H 0.4436 1.0692 0.4186 0.077 Uiso 1 1 calc R . .
H7B H 0.3276 1.0334 0.3841 0.077 Uiso 1 1 calc R . .
C8 C 0.6371(2) 0.92756(16) 0.33700(14) 0.0436(5) Uani 1 1 d . . .
C9 C 0.70485(18) 0.81978(14) 0.28997(13) 0.0370(4) Uani 1 1 d . . .
C10 C 0.58983(19) 0.79211(15) 0.25859(13) 0.0377(4) Uani 1 1 d . . .
C11 C 0.5781(2) 0.70047(17) 0.22128(15) 0.0486(5) Uani 1 1 d . . .
H11 H 0.6510 0.6405 0.2092 0.058 Uiso 1 1 calc R . .
C12 C 0.4553(2) 0.6995(2) 0.20215(18) 0.0589(6) Uani 1 1 d . . .
C13 C 0.3466(2) 0.7822(2) 0.22115(18) 0.0630(7) Uani 1 1 d . . .
H13 H 0.2642 0.7774 0.2079 0.076 Uiso 1 1 calc R . .
C14 C 0.3578(2) 0.8728(2) 0.25980(18) 0.0602(6) Uani 1 1 d . . .
H14 H 0.2838 0.9317 0.2730 0.072 Uiso 1 1 calc R . .
C15 C 0.4794(2) 0.87613(16) 0.27906(14) 0.0440(5) Uani 1 1 d . . .
C16 C 0.77443(19) 0.73414(15) 0.35244(14) 0.0409(5) Uani 1 1 d . . .
H16 H 0.8137 0.7714 0.3921 0.049 Uiso 1 1 calc R . .
C17 C 0.6789(2) 0.6757(2) 0.41255(16) 0.0551(6) Uani 1 1 d . . .
C18 C 0.4775(4) 0.7012(4) 0.5218(3) 0.1343(17) Uani 1 1 d D . .
H18A H 0.4854 0.7012 0.5860 0.161 Uiso 1 1 calc R . .
H18B H 0.4838 0.6265 0.5055 0.161 Uiso 1 1 calc R . .
C19 C 0.3460(4) 0.7722(5) 0.5083(4) 0.198(3) Uani 1 1 d D . .
H19A H 0.3404 0.8456 0.5257 0.297 Uiso 1 1 calc R . .
H19B H 0.2726 0.7446 0.5461 0.297 Uiso 1 1 calc R . .
H19C H 0.3402 0.7724 0.4443 0.297 Uiso 1 1 calc R . .
C20 C 1.0068(3) 1.2503(2) 0.1877(2) 0.0726(8) Uani 1 1 d . . .
H20 H 1.0999 1.2292 0.1648 0.087 Uiso 1 1 calc R . .
C21 C 0.9458(4) 1.3579(2) 0.1967(3) 0.0992(11) Uani 1 1 d . . .
H21 H 0.9977 1.4105 0.1812 0.119 Uiso 1 1 calc R . .
C22 C 0.8144(4) 1.3885(2) 0.2271(2) 0.0860(10) Uani 1 1 d . . .
H22 H 0.7737 1.4627 0.2322 0.103 Uiso 1 1 calc R . .
C23 C 0.7388(3) 1.3150(2) 0.25060(19) 0.0737(8) Uani 1 1 d . . .
H23 H 0.6454 1.3374 0.2714 0.088 Uiso 1 1 calc R . .
C24 C 0.7988(3) 1.20698(19) 0.24401(19) 0.0645(7) Uani 1 1 d . . .
H24 H 0.7463 1.1551 0.2621 0.077 Uiso 1 1 calc R . .
C25 C 0.9326(2) 1.17385(17) 0.21183(16) 0.0517(6) Uani 1 1 d . . .
C26 C 1.0034(2) 1.05642(18) 0.2022(2) 0.0622(7) Uani 1 1 d . . .
H26A H 1.0769 1.0494 0.1482 0.075 Uiso 1 1 calc R . .
H26B H 1.0432 1.0327 0.2561 0.075 Uiso 1 1 calc R . .
C27 C 0.91743(19) 0.89276(15) 0.24397(15) 0.0409(5) Uani 1 1 d . . .
C28 C 0.82490(18) 0.83228(14) 0.21092(13) 0.0367(4) Uani 1 1 d . . .
C29 C 0.78963(19) 0.90089(16) 0.13083(13) 0.0406(5) Uani 1 1 d . . .
C30 C 0.7171(2) 0.88777(18) 0.06795(14) 0.0493(5) Uani 1 1 d . . .
H30 H 0.6787 0.8272 0.0706 0.059 Uiso 1 1 calc R . .
C31 C 0.7032(3) 0.9660(2) 0.00177(15) 0.0614(7) Uani 1 1 d . . .
C32 C 0.7570(3) 1.0551(2) -0.00462(17) 0.0662(7) Uani 1 1 d . . .
H32 H 0.7426 1.1079 -0.0513 0.079 Uiso 1 1 calc R . .
C33 C 0.8313(2) 1.06765(18) 0.05620(16) 0.0561(6) Uani 1 1 d . . .
H33 H 0.8714 1.1275 0.0516 0.067 Uiso 1 1 calc R . .
C34 C 0.8461(2) 0.99037(16) 0.12449(14) 0.0439(5) Uani 1 1 d . . .
C35 C 0.89524(19) 0.71339(14) 0.19352(13) 0.0378(5) Uani 1 1 d . . .
H35 H 0.8369 0.6823 0.1638 0.045 Uiso 1 1 calc R . .
C36 C 1.0291(2) 0.69772(16) 0.12911(14) 0.0416(5) Uani 1 1 d . . .
C37 C 1.1953(3) 0.5739(2) 0.0347(2) 0.0698(7) Uani 1 1 d . . .
H37A H 1.2646 0.5758 0.0692 0.084 Uiso 1 1 calc R . .
H37B H 1.2023 0.6263 -0.0168 0.084 Uiso 1 1 calc R . .
C38 C 1.2147(3) 0.4646(3) 0.0005(2) 0.0890(10) Uani 1 1 d . . .
H38A H 1.2141 0.4127 0.0516 0.133 Uiso 1 1 calc R . .
H38B H 1.3001 0.4466 -0.0424 0.133 Uiso 1 1 calc R . .
H38C H 1.1425 0.4624 -0.0303 0.133 Uiso 1 1 calc R . .
C39 C 0.88927(18) 0.66012(15) 0.28952(14) 0.0389(5) Uani 1 1 d . . .
H39 H 0.8627 0.5905 0.2876 0.047 Uiso 1 1 calc R . .
C40 C 1.0188(2) 0.63543(16) 0.32218(16) 0.0472(5) Uani 1 1 d . . .
C41 C 1.1095(3) 0.6154(3) 0.4546(2) 0.0786(8) Uani 1 1 d . . .
H41A H 1.1695 0.6637 0.4282 0.094 Uiso 1 1 calc R . .
H41B H 1.1593 0.5403 0.4436 0.094 Uiso 1 1 calc R . .
C42 C 1.0626(4) 0.6324(3) 0.5535(2) 0.0929(10) Uani 1 1 d . . .
H42A H 1.0200 0.7082 0.5639 0.139 Uiso 1 1 calc R . .
H42B H 1.1385 0.6121 0.5837 0.139 Uiso 1 1 calc R . .
H42C H 0.9984 0.5881 0.5781 0.139 Uiso 1 1 calc R . .
F1 F 0.44511(17) 0.60869(14) 0.16487(14) 0.0924(6) Uani 1 1 d . . .
F2 F 0.63211(19) 0.95411(15) -0.06133(11) 0.0919(6) Uani 1 1 d . . .
N1 N 0.51108(17) 0.95668(13) 0.32332(12) 0.0484(5) Uani 1 1 d . . .
N2 N 0.91727(17) 0.98540(13) 0.19313(12) 0.0461(4) Uani 1 1 d . . .
O1 O 0.68858(17) 0.97883(12) 0.37821(12) 0.0620(5) Uani 1 1 d . . .
O2 O 0.6869(2) 0.58107(16) 0.41403(16) 0.0900(7) Uani 1 1 d . . .
O3 O 0.58204(19) 0.74496(16) 0.46302(13) 0.0790(6) Uani 1 1 d . . .
O4 O 0.98097(15) 0.86226(12) 0.30263(11) 0.0543(4) Uani 1 1 d . . .
O5 O 1.09192(15) 0.76640(12) 0.10935(11) 0.0565(4) Uani 1 1 d . . .
O6 O 1.06377(14) 0.60153(12) 0.09350(10) 0.0521(4) Uani 1 1 d . . .
O7 O 1.12665(16) 0.61228(14) 0.27502(12) 0.0643(5) Uani 1 1 d . . .
O8 O 0.99554(15) 0.63777(13) 0.41326(11) 0.0601(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 1.358(4) . ?
C1 C2 1.384(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.319(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.508(4) . ?
C7 N1 1.461(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.219(2) . ?
C8 N1 1.352(3) . ?
C8 C9 1.546(3) . ?
C9 C10 1.516(3) . ?
C9 C16 1.549(3) . ?
C9 C28 1.572(3) . ?
C10 C11 1.381(3) . ?
C10 C15 1.387(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.364(4) . ?
C12 F1 1.366(3) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 N1 1.408(3) . ?
C16 C17 1.503(3) . ?
C16 C39 1.541(3) . ?
C16 H16 1.0000 . ?
C17 O2 1.195(3) . ?
C17 O3 1.325(3) . ?
C18 O3 1.454(4) . ?
C18 C19 1.518(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.374(3) . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.338(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.352(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.367(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.519(3) . ?
C26 N2 1.461(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 O4 1.211(2) . ?
C27 N2 1.364(3) . ?
C27 C28 1.557(3) . ?
C28 C29 1.501(3) . ?
C28 C35 1.546(3) . ?
C29 C30 1.382(3) . ?
C29 C34 1.399(3) . ?
C30 C31 1.367(3) . ?
C30 H30 0.9500 . ?
C31 F2 1.369(3) . ?
C31 C32 1.379(4) . ?
C32 C33 1.368(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(3) . ?
C33 H33 0.9500 . ?
C34 N2 1.394(3) . ?
C35 C36 1.513(3) . ?
C35 C39 1.549(3) . ?
C35 H35 1.0000 . ?
C36 O5 1.205(2) . ?
C36 O6 1.321(2) . ?
C37 O6 1.459(3) . ?
C37 C38 1.483(4) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.509(3) . ?
C39 H39 1.0000 . ?
C40 O7 1.191(3) . ?
C40 O8 1.344(3) . ?
C41 O8 1.434(3) . ?
C41 C42 1.482(5) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
C6 C1 C2 122.1(3) . . ?
C6 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C1 C2 C3 118.4(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.9(4) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 123.7(2) . . ?
C5 C6 C7 118.2(3) . . ?
N1 C7 C6 113.9(2) . . ?
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 125.52(19) . . ?
O1 C8 C9 126.10(18) . . ?
N1 C8 C9 108.37(16) . . ?
C10 C9 C8 101.51(15) . . ?
C10 C9 C16 115.37(15) . . ?
C8 C9 C16 113.32(16) . . ?
C10 C9 C28 114.14(16) . . ?
C8 C9 C28 111.43(15) . . ?
C16 C9 C28 101.53(14) . . ?
C11 C10 C15 119.56(19) . . ?
C11 C10 C9 131.66(18) . . ?
C15 C10 C9 108.64(17) . . ?
C10 C11 C12 117.4(2) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C13 C12 F1 119.7(2) . . ?
C13 C12 C11 123.4(2) . . ?
F1 C12 C11 116.8(2) . . ?
C12 C13 C14 119.1(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 118.6(2) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C10 121.8(2) . . ?
C14 C15 N1 128.27(19) . . ?
C10 C15 N1 109.86(17) . . ?
C17 C16 C39 113.70(18) . . ?
C17 C16 C9 112.10(16) . . ?
C39 C16 C9 106.38(16) . . ?
C17 C16 H16 108.2 . . ?
C39 C16 H16 108.2 . . ?
C9 C16 H16 108.2 . . ?
O2 C17 O3 124.6(2) . . ?
O2 C17 C16 125.5(2) . . ?
O3 C17 C16 110.0(2) . . ?
O3 C18 C19 106.9(3) . . ?
O3 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
O3 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
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 . . ?
C25 C20 C21 119.9(3) . . ?
C25 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C24 119.3(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C20 118.5(2) . . ?
C24 C25 C26 123.1(2) . . ?
C20 C25 C26 118.4(2) . . ?
N2 C26 C25 113.96(19) . . ?
N2 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
N2 C26 H26B 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
O4 C27 N2 125.85(18) . . ?
O4 C27 C28 126.45(18) . . ?
N2 C27 C28 107.68(17) . . ?
C29 C28 C35 117.37(16) . . ?
C29 C28 C27 101.91(15) . . ?
C35 C28 C27 110.57(15) . . ?
C29 C28 C9 115.83(15) . . ?
C35 C28 C9 100.88(14) . . ?
C27 C28 C9 110.49(15) . . ?
C30 C29 C34 120.19(19) . . ?
C30 C29 C28 131.26(18) . . ?
C34 C29 C28 108.54(17) . . ?
C31 C30 C29 116.9(2) . . ?
C31 C30 H30 121.6 . . ?
C29 C30 H30 121.6 . . ?
C30 C31 F2 117.7(2) . . ?
C30 C31 C32 123.5(2) . . ?
F2 C31 C32 118.8(2) . . ?
C33 C32 C31 120.0(2) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 117.8(2) . . ?
C32 C33 H33 121.1 . . ?
C34 C33 H33 121.1 . . ?
C33 C34 N2 128.1(2) . . ?
C33 C34 C29 121.6(2) . . ?
N2 C34 C29 110.23(17) . . ?
C36 C35 C28 114.07(16) . . ?
C36 C35 C39 117.98(15) . . ?
C28 C35 C39 104.54(15) . . ?
C36 C35 H35 106.5 . . ?
C28 C35 H35 106.5 . . ?
C39 C35 H35 106.5 . . ?
O5 C36 O6 124.65(19) . . ?
O5 C36 C35 124.06(18) . . ?
O6 C36 C35 111.17(17) . . ?
O6 C37 C38 108.3(2) . . ?
O6 C37 H37A 110.0 . . ?
C38 C37 H37A 110.0 . . ?
O6 C37 H37B 110.0 . . ?
C38 C37 H37B 110.0 . . ?
H37A C37 H37B 108.4 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C16 113.76(17) . . ?
C40 C39 C35 115.04(17) . . ?
C16 C39 C35 105.68(15) . . ?
C40 C39 H39 107.3 . . ?
C16 C39 H39 107.3 . . ?
C35 C39 H39 107.3 . . ?
O7 C40 O8 124.2(2) . . ?
O7 C40 C39 125.4(2) . . ?
O8 C40 C39 110.35(19) . . ?
O8 C41 C42 108.2(3) . . ?
O8 C41 H41A 110.1 . . ?
C42 C41 H41A 110.1 . . ?
O8 C41 H41B 110.1 . . ?
C42 C41 H41B 110.1 . . ?
H41A C41 H41B 108.4 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C8 N1 C15 111.29(16) . . ?
C8 N1 C7 122.73(19) . . ?
C15 N1 C7 125.16(19) . . ?
C27 N2 C34 111.32(16) . . ?
C27 N2 C26 121.30(19) . . ?
C34 N2 C26 126.41(19) . . ?
C17 O3 C18 116.6(3) . . ?
C36 O6 C37 116.40(18) . . ?
C40 O8 C41 116.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.106



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 0.000 0.500 98 25 ' '
2 0.435 0.518 0.357 20 2 ' '
3 0.500 0.500 0.000 13 1 ' '
4 0.564 0.482 0.643 20 2 ' '
_platon_squeeze_details          
; 
;
#=================================================================

