# 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_3g
_audit_block_doi                 10.5517/cc1j93tr
_database_code_depnum_ccdc_archive 'CCDC 1408944'
_audit_update_record             
;
2015-06-26 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H29 Cl N4 O5'
_chemical_formula_sum            'C35 H29 Cl N4 O5'
_chemical_formula_weight         621.07

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

_symmetry_cell_setting           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                   8.2071(13)
_cell_length_b                   27.176(4)
_cell_length_c                   14.260(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.488(5)
_cell_angle_gamma                90.00
_cell_volume                     3092.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.28

_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      0
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.966
_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            30424
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         27.61
_reflns_number_total             7088
_reflns_number_gt                4438
_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)+(0.0868P)²+0.1864P] 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         7088
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1584
_refine_ls_wR_factor_gt          0.1341
_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 0.4993(5) 0.27124(11) 0.4305(2) 0.1007(11) Uani 1 1 d . . .
H1A H 0.5614 0.2837 0.4914 0.151 Uiso 1 1 calc R . .
H1B H 0.4403 0.2978 0.3928 0.151 Uiso 1 1 calc R . .
H1C H 0.5749 0.2565 0.3966 0.151 Uiso 1 1 calc R . .
C2 C 0.3758(4) 0.23337(8) 0.44727(19) 0.0694(7) Uani 1 1 d . . .
H2A H 0.3108 0.2216 0.3856 0.083 Uiso 1 1 calc R . .
H2B H 0.2991 0.2485 0.4812 0.083 Uiso 1 1 calc R . .
C3 C 0.4624(3) 0.19034(7) 0.50537(15) 0.0477(5) Uani 1 1 d . . .
H3A H 0.5276 0.1728 0.4675 0.057 Uiso 1 1 calc R . .
H3B H 0.5393 0.2027 0.5628 0.057 Uiso 1 1 calc R . .
C4 C 0.3077(2) 0.15600(6) 0.62142(13) 0.0366(4) Uani 1 1 d . . .
C5 C 0.1603(2) 0.11984(6) 0.61738(12) 0.0334(4) Uani 1 1 d . . .
C6 C 0.1423(2) 0.09733(6) 0.51736(12) 0.0356(4) Uani 1 1 d . . .
C7 C 0.0441(3) 0.05970(7) 0.47112(15) 0.0450(5) Uani 1 1 d . . .
H7 H -0.0304 0.0435 0.5007 0.054 Uiso 1 1 calc R . .
C8 C 0.0580(3) 0.04614(7) 0.37924(15) 0.0514(5) Uani 1 1 d . . .
H8 H -0.0061 0.0202 0.3478 0.062 Uiso 1 1 calc R . .
C9 C 0.1647(3) 0.07052(8) 0.33468(15) 0.0529(6) Uani 1 1 d . . .
H9 H 0.1698 0.0615 0.2725 0.064 Uiso 1 1 calc R . .
C10 C 0.2655(3) 0.10838(7) 0.38072(14) 0.0472(5) Uani 1 1 d . . .
H10 H 0.3394 0.1247 0.3510 0.057 Uiso 1 1 calc R . .
C11 C 0.2520(2) 0.12081(6) 0.47178(13) 0.0373(4) Uani 1 1 d . . .
C12 C 0.0007(2) 0.15183(6) 0.61952(12) 0.0349(4) Uani 1 1 d . . .
C13 C -0.0117(3) 0.19420(7) 0.55337(14) 0.0419(5) Uani 1 1 d . . .
C14 C -0.1514(3) 0.12180(7) 0.58741(14) 0.0415(5) Uani 1 1 d . . .
C15 C -0.3958(3) 0.28487(7) 0.71475(13) 0.0434(5) Uani 1 1 d . . .
H15 H -0.4384 0.2532 0.7024 0.052 Uiso 1 1 calc R . .
C16 C -0.5021(3) 0.32428(8) 0.70388(14) 0.0476(5) Uani 1 1 d . . .
C17 C -0.4462(3) 0.37169(8) 0.72302(16) 0.0552(6) Uani 1 1 d . . .
H17 H -0.5208 0.3980 0.7144 0.066 Uiso 1 1 calc R . .
C18 C -0.2786(3) 0.37909(7) 0.75499(18) 0.0617(6) Uani 1 1 d . . .
H18 H -0.2380 0.4108 0.7698 0.074 Uiso 1 1 calc R . .
C19 C -0.1684(3) 0.34026(7) 0.76572(16) 0.0527(5) Uani 1 1 d . . .
H19 H -0.0542 0.3462 0.7877 0.063 Uiso 1 1 calc R . .
C20 C -0.2243(3) 0.29235(6) 0.74432(13) 0.0386(4) Uani 1 1 d . . .
C21 C -0.1020(2) 0.25287(6) 0.74925(14) 0.0408(5) Uani 1 1 d . . .
H21 H 0.0098 0.2620 0.7703 0.049 Uiso 1 1 calc R . .
C22 C -0.1297(2) 0.20577(6) 0.72763(13) 0.0386(4) Uani 1 1 d . . .
H22 H -0.2394 0.1943 0.7137 0.046 Uiso 1 1 calc R . .
C23 C 0.0075(2) 0.17050(6) 0.72466(13) 0.0368(4) Uani 1 1 d . . .
H23 H 0.1149 0.1872 0.7489 0.044 Uiso 1 1 calc R . .
C24 C -0.0970(3) 0.12494(7) 0.85357(13) 0.0401(5) Uani 1 1 d . . .
C25 C -0.0351(3) 0.14351(9) 0.94370(16) 0.0637(6) Uani 1 1 d . . .
H25 H 0.0704 0.1581 0.9592 0.076 Uiso 1 1 calc R . .
C26 C -0.1295(4) 0.14058(11) 1.01141(19) 0.0850(9) Uani 1 1 d . . .
H26 H -0.0871 0.1528 1.0732 0.102 Uiso 1 1 calc R . .
C27 C -0.2840(4) 0.12003(10) 0.9885(2) 0.0765(8) Uani 1 1 d . . .
H27 H -0.3472 0.1181 1.0347 0.092 Uiso 1 1 calc R . .
C28 C -0.3465(3) 0.10238(10) 0.8991(2) 0.0739(7) Uani 1 1 d . . .
H28 H -0.4532 0.0886 0.8835 0.089 Uiso 1 1 calc R . .
C29 C -0.2527(3) 0.10467(9) 0.83041(17) 0.0614(6) Uani 1 1 d . . .
H29 H -0.2957 0.0924 0.7687 0.074 Uiso 1 1 calc R . .
C30 C 0.1043(2) 0.08781(6) 0.77291(13) 0.0364(4) Uani 1 1 d . . .
C31 C 0.1134(3) 0.04825(7) 0.84874(14) 0.0428(5) Uani 1 1 d . . .
C32 C 0.2546(5) 0.02333(13) 1.0039(2) 0.1052(11) Uani 1 1 d . . .
H32A H 0.1620 0.0263 1.0340 0.158 Uiso 1 1 calc R . .
H32B H 0.3572 0.0302 1.0503 0.158 Uiso 1 1 calc R . .
H32C H 0.2582 -0.0095 0.9795 0.158 Uiso 1 1 calc R . .
C33 C 0.1868(2) 0.08384(6) 0.70101(13) 0.0348(4) Uani 1 1 d . . .
C34 C 0.3063(3) 0.04346(6) 0.70634(14) 0.0402(5) Uani 1 1 d . . .
C35 C 0.5141(3) 0.00819(9) 0.6397(2) 0.0712(7) Uani 1 1 d . . .
H35A H 0.5838 0.0028 0.7030 0.107 Uiso 1 1 calc R . .
H35B H 0.5832 0.0161 0.5959 0.107 Uiso 1 1 calc R . .
H35C H 0.4508 -0.0210 0.6181 0.107 Uiso 1 1 calc R . .
Cl1 Cl -0.71641(8) 0.31399(3) 0.66403(5) 0.0807(2) Uani 1 1 d . . .
N1 N 0.3460(2) 0.15617(5) 0.53388(11) 0.0388(4) Uani 1 1 d . . .
N2 N -0.0214(3) 0.22676(7) 0.50337(15) 0.0672(6) Uani 1 1 d . . .
N3 N -0.2689(3) 0.09887(7) 0.56429(15) 0.0639(5) Uani 1 1 d . . .
N4 N 0.0039(2) 0.12641(5) 0.78303(10) 0.0390(4) Uani 1 1 d . . .
O1 O 0.37273(18) 0.18089(5) 0.69062(10) 0.0501(4) Uani 1 1 d . . .
O2 O 0.0176(2) 0.01473(5) 0.84053(11) 0.0614(4) Uani 1 1 d . . .
O3 O 0.2342(2) 0.05821(6) 0.92486(10) 0.0581(4) Uani 1 1 d . . .
O4 O 0.3222(2) 0.00955(5) 0.76190(12) 0.0629(5) Uani 1 1 d . . .
O5 O 0.40116(18) 0.04842(5) 0.64295(11) 0.0530(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 C2 1.502(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.456(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O1 1.213(2) . ?
C4 N1 1.357(2) . ?
C4 C5 1.549(3) . ?
C5 C33 1.518(2) . ?
C5 C6 1.527(2) . ?
C5 C12 1.578(3) . ?
C6 C7 1.372(3) . ?
C6 C11 1.383(3) . ?
C7 C8 1.391(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 N1 1.409(2) . ?
C12 C14 1.472(3) . ?
C12 C13 1.477(3) . ?
C12 C23 1.571(2) . ?
C13 N2 1.127(2) . ?
C14 N3 1.131(3) . ?
C15 C16 1.367(3) . ?
C15 C20 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(3) . ?
C16 Cl1 1.740(2) . ?
C17 C18 1.360(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.460(3) . ?
C21 C22 1.324(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.487(3) . ?
C22 H22 0.9300 . ?
C23 N4 1.463(2) . ?
C23 H23 0.9800 . ?
C24 C29 1.359(3) . ?
C24 C25 1.364(3) . ?
C24 N4 1.445(2) . ?
C25 C26 1.374(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.354(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.347(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.381(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C33 1.358(3) . ?
C30 N4 1.363(2) . ?
C30 C31 1.514(3) . ?
C31 O2 1.191(2) . ?
C31 O3 1.316(2) . ?
C32 O3 1.452(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.462(3) . ?
C34 O4 1.202(2) . ?
C34 O5 1.330(2) . ?
C35 O5 1.441(2) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 111.6(2) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 C2 113.04(18) . . ?
N1 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O1 C4 N1 126.46(17) . . ?
O1 C4 C5 125.16(17) . . ?
N1 C4 C5 108.34(15) . . ?
C33 C5 C6 116.13(14) . . ?
C33 C5 C4 114.33(15) . . ?
C6 C5 C4 101.15(14) . . ?
C33 C5 C12 107.90(14) . . ?
C6 C5 C12 109.80(14) . . ?
C4 C5 C12 107.10(13) . . ?
C7 C6 C11 119.45(17) . . ?
C7 C6 C5 131.73(17) . . ?
C11 C6 C5 108.81(15) . . ?
C6 C7 C8 118.85(19) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 120.74(19) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.05(19) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 117.41(19) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
C10 C11 C6 122.47(18) . . ?
C10 C11 N1 127.58(17) . . ?
C6 C11 N1 109.91(16) . . ?
C14 C12 C13 107.86(16) . . ?
C14 C12 C23 108.36(15) . . ?
C13 C12 C23 109.85(14) . . ?
C14 C12 C5 109.61(14) . . ?
C13 C12 C5 110.55(15) . . ?
C23 C12 C5 110.55(14) . . ?
N2 C13 C12 179.5(2) . . ?
N3 C14 C12 178.8(2) . . ?
C16 C15 C20 119.67(18) . . ?
C16 C15 H15 120.2 . . ?
C20 C15 H15 120.2 . . ?
C15 C16 C17 122.5(2) . . ?
C15 C16 Cl1 118.72(17) . . ?
C17 C16 Cl1 118.76(17) . . ?
C18 C17 C16 118.1(2) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C17 C18 C19 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C19 117.64(18) . . ?
C15 C20 C21 123.02(16) . . ?
C19 C20 C21 119.27(18) . . ?
C22 C21 C20 128.35(19) . . ?
C22 C21 H21 115.8 . . ?
C20 C21 H21 115.8 . . ?
C21 C22 C23 122.68(18) . . ?
C21 C22 H22 118.7 . . ?
C23 C22 H22 118.7 . . ?
N4 C23 C22 113.31(15) . . ?
N4 C23 C12 106.11(13) . . ?
C22 C23 C12 112.11(15) . . ?
N4 C23 H23 108.4 . . ?
C22 C23 H23 108.4 . . ?
C12 C23 H23 108.4 . . ?
C29 C24 C25 120.1(2) . . ?
C29 C24 N4 120.06(18) . . ?
C25 C24 N4 119.83(19) . . ?
C24 C25 C26 119.6(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 120.2(3) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C24 C29 C28 119.6(2) . . ?
C24 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C33 C30 N4 124.14(16) . . ?
C33 C30 C31 122.18(16) . . ?
N4 C30 C31 113.66(15) . . ?
O2 C31 O3 126.26(19) . . ?
O2 C31 C30 123.46(19) . . ?
O3 C31 C30 110.18(17) . . ?
O3 C32 H32A 109.5 . . ?
O3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 C34 117.82(16) . . ?
C30 C33 C5 122.45(16) . . ?
C34 C33 C5 119.73(15) . . ?
O4 C34 O5 122.30(17) . . ?
O4 C34 C33 125.32(18) . . ?
O5 C34 C33 112.37(15) . . ?
O5 C35 H35A 109.5 . . ?
O5 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O5 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C4 N1 C11 111.44(15) . . ?
C4 N1 C3 124.54(16) . . ?
C11 N1 C3 123.94(15) . . ?
C30 N4 C24 120.76(14) . . ?
C30 N4 C23 118.50(14) . . ?
C24 N4 C23 120.65(14) . . ?
C31 O3 C32 115.7(2) . . ?
C34 O5 C35 115.32(16) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.61
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.118
####################################################################### 
# 
# 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_3i
_audit_block_doi                 10.5517/cc1j93vs
_database_code_depnum_ccdc_archive 'CCDC 1408945'
_audit_update_record             
;
2015-06-26 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H28 Br Cl N4 O5'
_chemical_formula_sum            'C39 H28 Br Cl N4 O5'
_chemical_formula_weight         748.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   10.573(2)
_cell_length_b                   13.505(3)
_cell_length_c                   25.317(6)
_cell_angle_alpha                92.856(6)
_cell_angle_beta                 93.307(5)
_cell_angle_gamma                94.257(6)
_cell_volume                     3593.8(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6122
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      20.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1528
_exptl_absorpt_coefficient_mu    1.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_T_max  0.718
_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            38285
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_sigmaI/netI    0.2510
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         0.81
_diffrn_reflns_theta_max         27.54
_reflns_number_total             14437
_reflns_number_gt                5348
_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)+(0.0650P)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         14437
_refine_ls_number_parameters     905
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2621
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.1702
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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
Br1 Br 0.34453(7) 0.80607(5) -0.04547(2) 0.0825(3) Uani 1 1 d . . .
Br2 Br -0.07612(6) 0.26406(6) 0.14166(3) 0.0877(3) Uani 1 1 d . . .
C1 C 0.9775(7) 0.7553(5) 0.0463(4) 0.098(3) Uani 1 1 d . . .
C2 C 0.9708(9) 0.8137(9) 0.0048(4) 0.124(4) Uani 1 1 d . . .
H2 H 1.0160 0.8011 -0.0249 0.148 Uiso 1 1 calc R . .
C3 C 0.8965(9) 0.8913(8) 0.0074(3) 0.133(4) Uani 1 1 d . . .
H3 H 0.8916 0.9329 -0.0207 0.160 Uiso 1 1 calc R . .
C4 C 0.8288(6) 0.9090(6) 0.0508(3) 0.090(2) Uani 1 1 d . . .
H4 H 0.7796 0.9632 0.0520 0.108 Uiso 1 1 calc R . .
C5 C 0.8318(5) 0.8491(5) 0.0921(2) 0.0488(15) Uani 1 1 d . . .
C6 C 0.9091(6) 0.7710(5) 0.0901(3) 0.0719(19) Uani 1 1 d . . .
H6 H 0.9149 0.7293 0.1181 0.086 Uiso 1 1 calc R . .
C7 C 0.7601(5) 0.8627(4) 0.1394(2) 0.0400(14) Uani 1 1 d . . .
H7 H 0.7627 0.8129 0.1634 0.048 Uiso 1 1 calc R . .
C8 C 0.6931(5) 0.9368(4) 0.15151(18) 0.0344(13) Uani 1 1 d . . .
H8 H 0.6926 0.9896 0.1293 0.041 Uiso 1 1 calc R . .
C9 C 0.6175(4) 0.9409(3) 0.19902(18) 0.0322(13) Uani 1 1 d . . .
H9 H 0.6373 0.8857 0.2210 0.039 Uiso 1 1 calc R . .
C10 C 0.4384(4) 0.9016(4) 0.13135(19) 0.0338(13) Uani 1 1 d . . .
C11 C 0.4309(5) 0.8027(4) 0.1156(2) 0.0455(15) Uani 1 1 d . . .
H11 H 0.4462 0.7555 0.1402 0.055 Uiso 1 1 calc R . .
C12 C 0.4008(5) 0.7733(4) 0.0632(2) 0.0518(16) Uani 1 1 d . . .
H12 H 0.3970 0.7063 0.0523 0.062 Uiso 1 1 calc R . .
C13 C 0.3764(5) 0.8430(5) 0.0274(2) 0.0468(15) Uani 1 1 d . . .
C14 C 0.3811(5) 0.9426(5) 0.0435(2) 0.0558(16) Uani 1 1 d . . .
H14 H 0.3636 0.9897 0.0190 0.067 Uiso 1 1 calc R . .
C15 C 0.4117(5) 0.9718(4) 0.0955(2) 0.0475(15) Uani 1 1 d . . .
H15 H 0.4145 1.0387 0.1066 0.057 Uiso 1 1 calc R . .
C16 C 0.3982(4) 0.9592(3) 0.2215(2) 0.0296(12) Uani 1 1 d . . .
C17 C 0.2613(5) 0.9301(5) 0.2031(2) 0.0413(14) Uani 1 1 d . . .
C18 C 0.0809(5) 0.9826(5) 0.1569(3) 0.086(2) Uani 1 1 d . . .
H18A H 0.0852 0.9334 0.1285 0.128 Uiso 1 1 calc R . .
H18B H 0.0492 1.0415 0.1431 0.128 Uiso 1 1 calc R . .
H18C H 0.0250 0.9570 0.1824 0.128 Uiso 1 1 calc R . .
C19 C 0.4341(4) 1.0046(3) 0.26949(19) 0.0300(12) Uani 1 1 d . . .
C20 C 0.3472(5) 1.0255(4) 0.3109(2) 0.0398(14) Uani 1 1 d . . .
C21 C 0.1364(5) 1.0043(5) 0.3378(2) 0.0691(18) Uani 1 1 d . . .
H21A H 0.1697 0.9826 0.3710 0.104 Uiso 1 1 calc R . .
H21B H 0.0583 0.9659 0.3271 0.104 Uiso 1 1 calc R . .
H21C H 0.1210 1.0734 0.3417 0.104 Uiso 1 1 calc R . .
C22 C 0.5714(4) 1.0393(3) 0.28480(17) 0.0281(12) Uani 1 1 d . . .
C23 C 0.5866(5) 1.1464(4) 0.3114(2) 0.0363(13) Uani 1 1 d . . .
C24 C 0.7055(5) 1.2353(4) 0.3882(2) 0.0588(17) Uani 1 1 d . . .
H24A H 0.7067 1.2921 0.3662 0.071 Uiso 1 1 calc R . .
H24B H 0.7917 1.2301 0.4025 0.071 Uiso 1 1 calc R . .
C25 C 0.6240(6) 1.2548(5) 0.4331(2) 0.0545(17) Uani 1 1 d . . .
C26 C 0.5421(7) 1.1838(6) 0.4520(3) 0.0717(19) Uani 1 1 d . . .
H26 H 0.5357 1.1200 0.4359 0.086 Uiso 1 1 calc R . .
C27 C 0.4684(7) 1.2028(7) 0.4942(3) 0.102(3) Uani 1 1 d . . .
H27 H 0.4137 1.1527 0.5060 0.123 Uiso 1 1 calc R . .
C28 C 0.4767(9) 1.2939(10) 0.5177(4) 0.122(4) Uani 1 1 d . . .
H28 H 0.4286 1.3069 0.5466 0.146 Uiso 1 1 calc R . .
C29 C 0.5562(11) 1.3693(7) 0.4996(4) 0.119(4) Uani 1 1 d . . .
H29 H 0.5601 1.4329 0.5158 0.143 Uiso 1 1 calc R . .
C30 C 0.6311(7) 1.3500(5) 0.4564(3) 0.089(2) Uani 1 1 d . . .
H30 H 0.6844 1.4004 0.4439 0.107 Uiso 1 1 calc R . .
C31 C 0.6945(5) 1.0500(4) 0.3660(2) 0.0400(14) Uani 1 1 d . . .
C32 C 0.7668(5) 1.0194(5) 0.4088(2) 0.0607(17) Uani 1 1 d . . .
H32 H 0.8060 1.0650 0.4344 0.073 Uiso 1 1 calc R . .
C33 C 0.7782(6) 0.9185(6) 0.4118(3) 0.080(2) Uani 1 1 d . . .
H33 H 0.8266 0.8959 0.4399 0.096 Uiso 1 1 calc R . .
C34 C 0.7199(7) 0.8514(5) 0.3743(3) 0.076(2) Uani 1 1 d . . .
H34 H 0.7289 0.7839 0.3774 0.092 Uiso 1 1 calc R . .
C35 C 0.6471(5) 0.8827(4) 0.3316(2) 0.0497(15) Uani 1 1 d . . .
H35 H 0.6062 0.8366 0.3066 0.060 Uiso 1 1 calc R . .
C36 C 0.6368(4) 0.9826(4) 0.32685(19) 0.0335(13) Uani 1 1 d . . .
C37 C 0.6463(4) 1.0415(3) 0.23309(18) 0.0296(12) Uani 1 1 d . . .
C38 C 0.6144(5) 1.1237(4) 0.1999(2) 0.0352(14) Uani 1 1 d . . .
C39 C 0.7855(6) 1.0526(4) 0.24699(19) 0.0393(14) Uani 1 1 d . . .
C40 C 0.0847(5) 0.3246(5) 0.1677(2) 0.0525(16) Uani 1 1 d . . .
C41 C 0.1728(6) 0.2670(4) 0.1905(2) 0.0596(17) Uani 1 1 d . . .
H41 H 0.1529 0.1998 0.1949 0.071 Uiso 1 1 calc R . .
C42 C 0.2908(5) 0.3113(4) 0.2066(2) 0.0481(15) Uani 1 1 d . . .
H42 H 0.3522 0.2734 0.2215 0.058 Uiso 1 1 calc R . .
C43 C 0.3190(5) 0.4109(4) 0.20102(19) 0.0389(14) Uani 1 1 d . . .
C44 C 0.2287(5) 0.4679(4) 0.1799(2) 0.0456(15) Uani 1 1 d . . .
H44 H 0.2476 0.5357 0.1768 0.055 Uiso 1 1 calc R . .
C45 C 0.1094(5) 0.4243(5) 0.1633(2) 0.0538(16) Uani 1 1 d . . .
H45 H 0.0471 0.4624 0.1493 0.065 Uiso 1 1 calc R . .
C46 C 0.4975(4) 0.4558(3) 0.26902(19) 0.0324(13) Uani 1 1 d . . .
H46 H 0.5424 0.3957 0.2740 0.039 Uiso 1 1 calc R . .
C47 C 0.3976(4) 0.4602(4) 0.3080(2) 0.0377(13) Uani 1 1 d . . .
H47 H 0.3441 0.5117 0.3068 0.045 Uiso 1 1 calc R . .
C48 C 0.3819(4) 0.3943(4) 0.3441(2) 0.0383(14) Uani 1 1 d . . .
H48 H 0.4365 0.3434 0.3443 0.046 Uiso 1 1 calc R . .
C49 C 0.2870(5) 0.3930(4) 0.3839(2) 0.0395(14) Uani 1 1 d . . .
C50 C 0.2436(5) 0.3019(4) 0.4017(2) 0.0444(14) Uani 1 1 d . . .
H50 H 0.2801 0.2443 0.3908 0.053 Uiso 1 1 calc R . .
C51 C 0.1467(6) 0.2971(5) 0.4352(2) 0.0564(16) Uani 1 1 d . . .
C52 C 0.0941(7) 0.3795(6) 0.4536(3) 0.086(2) Uani 1 1 d . . .
H52 H 0.0292 0.3748 0.4768 0.103 Uiso 1 1 calc R . .
C53 C 0.1393(7) 0.4703(6) 0.4370(3) 0.086(2) Uani 1 1 d . . .
H53 H 0.1040 0.5276 0.4492 0.103 Uiso 1 1 calc R . .
C54 C 0.2355(6) 0.4781(4) 0.4028(2) 0.0578(16) Uani 1 1 d . . .
H54 H 0.2657 0.5402 0.3925 0.069 Uiso 1 1 calc R . .
C55 C 0.5957(5) 0.5486(3) 0.27674(19) 0.0348(13) Uani 1 1 d . . .
C56 C 0.6456(5) 0.5605(4) 0.3327(2) 0.0418(14) Uani 1 1 d . . .
C57 C 0.5240(5) 0.6369(4) 0.2640(2) 0.0432(15) Uani 1 1 d . . .
C58 C 0.7056(4) 0.5375(3) 0.23941(18) 0.0318(13) Uani 1 1 d . . .
C59 C 0.8012(4) 0.4680(4) 0.25941(18) 0.0291(12) Uani 1 1 d . . .
C60 C 0.7917(5) 0.3669(4) 0.26227(19) 0.0391(14) Uani 1 1 d . . .
H60 H 0.7168 0.3295 0.2510 0.047 Uiso 1 1 calc R . .
C61 C 0.8963(6) 0.3214(4) 0.2824(2) 0.0523(16) Uani 1 1 d . . .
H61 H 0.8909 0.2530 0.2857 0.063 Uiso 1 1 calc R . .
C62 C 1.0074(5) 0.3770(5) 0.2973(2) 0.0568(16) Uani 1 1 d . . .
H62 H 1.0765 0.3452 0.3107 0.068 Uiso 1 1 calc R . .
C63 C 1.0201(5) 0.4779(4) 0.2933(2) 0.0485(15) Uani 1 1 d . . .
H63 H 1.0965 0.5148 0.3026 0.058 Uiso 1 1 calc R . .
C64 C 0.9141(5) 0.5224(4) 0.27455(19) 0.0378(13) Uani 1 1 d . . .
C65 C 1.0121(5) 0.6987(4) 0.2680(2) 0.0518(16) Uani 1 1 d . . .
H65A H 0.9819 0.7602 0.2558 0.062 Uiso 1 1 calc R . .
H65B H 1.0731 0.6769 0.2435 0.062 Uiso 1 1 calc R . .
C66 C 1.0791(5) 0.7193(3) 0.3220(2) 0.0415(14) Uani 1 1 d . . .
C67 C 1.0160(6) 0.7159(4) 0.3677(3) 0.0674(18) Uani 1 1 d . . .
H67 H 0.9295 0.6967 0.3662 0.081 Uiso 1 1 calc R . .
C68 C 1.0812(8) 0.7411(5) 0.4163(3) 0.081(2) Uani 1 1 d . . .
H68 H 1.0379 0.7400 0.4472 0.097 Uiso 1 1 calc R . .
C69 C 1.2084(8) 0.7675(5) 0.4187(3) 0.081(2) Uani 1 1 d . . .
H69 H 1.2517 0.7848 0.4513 0.097 Uiso 1 1 calc R . .
C70 C 1.2713(6) 0.7685(5) 0.3743(3) 0.074(2) Uani 1 1 d . . .
H70 H 1.3584 0.7852 0.3763 0.089 Uiso 1 1 calc R . .
C71 C 1.2089(5) 0.7451(4) 0.3258(2) 0.0546(16) Uani 1 1 d . . .
H71 H 1.2538 0.7467 0.2953 0.065 Uiso 1 1 calc R . .
C72 C 0.7884(5) 0.6392(4) 0.2437(2) 0.0401(14) Uani 1 1 d . . .
C73 C 0.6483(5) 0.5116(3) 0.18384(19) 0.0330(13) Uani 1 1 d . . .
C74 C 0.7366(6) 0.5215(4) 0.1423(2) 0.0437(14) Uani 1 1 d . . .
C75 C 0.7722(6) 0.4886(5) 0.0522(2) 0.077(2) Uani 1 1 d . . .
H75A H 0.7915 0.5571 0.0451 0.116 Uiso 1 1 calc R . .
H75B H 0.7305 0.4540 0.0212 0.116 Uiso 1 1 calc R . .
H75C H 0.8495 0.4588 0.0615 0.116 Uiso 1 1 calc R . .
C76 C 0.5260(5) 0.4761(3) 0.1750(2) 0.0330(13) Uani 1 1 d . . .
C77 C 0.4629(5) 0.4619(5) 0.1194(2) 0.0418(14) Uani 1 1 d . . .
C78 C 0.3750(6) 0.3465(5) 0.0532(2) 0.094(2) Uani 1 1 d . . .
H78A H 0.2972 0.3789 0.0535 0.141 Uiso 1 1 calc R . .
H78B H 0.3561 0.2760 0.0475 0.141 Uiso 1 1 calc R . .
H78C H 0.4245 0.3707 0.0253 0.141 Uiso 1 1 calc R . .
Cl1 Cl 1.0737(3) 0.65541(17) 0.04541(14) 0.1949(15) Uani 1 1 d . . .
Cl2 Cl 0.08745(17) 0.18166(13) 0.45562(7) 0.0885(6) Uani 1 1 d . . .
N1 N 0.5911(5) 1.1834(4) 0.17198(18) 0.0589(14) Uani 1 1 d . . .
N2 N 0.8910(5) 1.0600(4) 0.25678(19) 0.0659(15) Uani 1 1 d . . .
N3 N 0.6663(4) 1.1464(3) 0.35503(15) 0.0373(11) Uani 1 1 d . . .
N4 N 0.4803(4) 0.9335(3) 0.18498(15) 0.0331(10) Uani 1 1 d . . .
N5 N 0.4467(4) 0.4546(3) 0.21423(17) 0.0363(11) Uani 1 1 d . . .
N6 N 0.4623(5) 0.6993(4) 0.2535(2) 0.0671(16) Uani 1 1 d . . .
N7 N 0.6860(5) 0.5698(4) 0.3751(2) 0.0640(15) Uani 1 1 d . . .
N8 N 0.9053(4) 0.6241(3) 0.26620(16) 0.0419(11) Uani 1 1 d . . .
O1 O 0.5419(3) 1.2185(3) 0.29310(13) 0.0463(10) Uani 1 1 d . . .
O2 O 0.3809(3) 1.0669(3) 0.35299(15) 0.0616(11) Uani 1 1 d . . .
O3 O 0.2273(3) 0.9908(3) 0.29800(13) 0.0574(11) Uani 1 1 d . . .
O4 O 0.2129(3) 0.8470(3) 0.20347(14) 0.0556(11) Uani 1 1 d . . .
O5 O 0.2084(3) 1.0068(3) 0.18251(14) 0.0517(10) Uani 1 1 d . . .
O6 O 0.4272(4) 0.5309(3) 0.09585(15) 0.0636(12) Uani 1 1 d . . .
O7 O 0.4463(3) 0.3675(3) 0.10351(14) 0.0563(11) Uani 1 1 d . . .
O8 O 0.8447(4) 0.5588(3) 0.15031(13) 0.0545(10) Uani 1 1 d . . .
O9 O 0.6907(3) 0.4828(3) 0.09510(16) 0.0618(11) Uani 1 1 d . . .
O10 O 0.7527(3) 0.7186(3) 0.23187(14) 0.0525(10) 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
Br1 C13 1.892(5) . ?
Br2 C40 1.899(5) . ?
C1 C2 1.345(11) . ?
C1 C6 1.374(9) . ?
C1 Cl1 1.749(8) . ?
C2 C3 1.357(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(8) . ?
C5 C7 1.464(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.302(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.483(6) . ?
C8 H8 0.9300 . ?
C9 N4 1.468(5) . ?
C9 C37 1.573(6) . ?
C9 H9 0.9800 . ?
C10 C11 1.370(6) . ?
C10 C15 1.378(6) . ?
C10 N4 1.438(5) . ?
C11 C12 1.377(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(7) . ?
C14 C15 1.369(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N4 1.354(6) . ?
C16 C19 1.354(6) . ?
C16 C17 1.512(7) . ?
C17 O4 1.199(6) . ?
C17 O5 1.327(6) . ?
C18 O5 1.468(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.464(7) . ?
C19 C22 1.514(6) . ?
C20 O2 1.201(5) . ?
C20 O3 1.335(6) . ?
C21 O3 1.446(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C36 1.507(6) . ?
C22 C23 1.559(6) . ?
C22 C37 1.569(6) . ?
C23 O1 1.214(5) . ?
C23 N3 1.351(6) . ?
C24 N3 1.452(6) . ?
C24 C25 1.489(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.368(8) . ?
C25 C30 1.383(8) . ?
C26 C27 1.382(9) . ?
C26 H26 0.9300 . ?
C27 C28 1.334(11) . ?
C27 H27 0.9300 . ?
C28 C29 1.386(12) . ?
C28 H28 0.9300 . ?
C29 C30 1.411(11) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.386(7) . ?
C31 C36 1.393(6) . ?
C31 N3 1.395(6) . ?
C32 C33 1.382(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.366(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.393(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.372(6) . ?
C35 H35 0.9300 . ?
C37 C38 1.472(7) . ?
C37 C39 1.488(7) . ?
C38 N1 1.130(6) . ?
C39 N2 1.125(6) . ?
C40 C45 1.364(7) . ?
C40 C41 1.377(7) . ?
C41 C42 1.374(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.373(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.371(6) . ?
C43 N5 1.447(6) . ?
C44 C45 1.386(6) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C46 N5 1.457(5) . ?
C46 C47 1.489(6) . ?
C46 C55 1.564(6) . ?
C46 H46 0.9800 . ?
C47 C48 1.316(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.462(7) . ?
C48 H48 0.9300 . ?
C49 C54 1.385(7) . ?
C49 C50 1.386(7) . ?
C50 C51 1.367(7) . ?
C50 H50 0.9300 . ?
C51 C52 1.353(8) . ?
C51 Cl2 1.751(6) . ?
C52 C53 1.377(8) . ?
C52 H52 0.9300 . ?
C53 C54 1.375(8) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C55 C56 1.480(7) . ?
C55 C57 1.499(7) . ?
C55 C58 1.551(6) . ?
C56 N7 1.129(6) . ?
C57 N6 1.136(6) . ?
C58 C59 1.512(6) . ?
C58 C73 1.513(6) . ?
C58 C72 1.569(6) . ?
C59 C60 1.367(6) . ?
C59 C64 1.378(6) . ?
C60 C61 1.388(6) . ?
C60 H60 0.9300 . ?
C61 C62 1.370(7) . ?
C61 H61 0.9300 . ?
C62 C63 1.369(7) . ?
C62 H62 0.9300 . ?
C63 C64 1.382(6) . ?
C63 H63 0.9300 . ?
C64 N8 1.408(6) . ?
C65 N8 1.454(6) . ?
C65 C66 1.505(7) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C66 C67 1.370(7) . ?
C66 C71 1.388(7) . ?
C67 C68 1.389(8) . ?
C67 H67 0.9300 . ?
C68 C69 1.364(9) . ?
C68 H68 0.9300 . ?
C69 C70 1.339(9) . ?
C69 H69 0.9300 . ?
C70 C71 1.370(7) . ?
C70 H70 0.9300 . ?
C71 H71 0.9300 . ?
C72 O10 1.208(5) . ?
C72 N8 1.365(6) . ?
C73 C76 1.348(6) . ?
C73 C74 1.451(7) . ?
C74 O8 1.216(6) . ?
C74 O9 1.329(6) . ?
C75 O9 1.426(6) . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 0.9600 . ?
C76 N5 1.364(6) . ?
C76 C77 1.519(7) . ?
C77 O6 1.203(6) . ?
C77 O7 1.315(6) . ?
C78 O7 1.446(6) . ?
C78 H78A 0.9600 . ?
C78 H78B 0.9600 . ?
C78 H78C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.8(8) . . ?
C2 C1 Cl1 120.3(8) . . ?
C6 C1 Cl1 117.9(8) . . ?
C1 C2 C3 118.5(8) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.7(9) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 121.4(8) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.0(6) . . ?
C4 C5 C7 124.3(6) . . ?
C6 C5 C7 117.7(6) . . ?
C1 C6 C5 119.5(7) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C5 127.2(5) . . ?
C8 C7 H7 116.4 . . ?
C5 C7 H7 116.4 . . ?
C7 C8 C9 123.1(5) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
N4 C9 C8 112.1(4) . . ?
N4 C9 C37 105.8(4) . . ?
C8 C9 C37 112.2(4) . . ?
N4 C9 H9 108.9 . . ?
C8 C9 H9 108.9 . . ?
C37 C9 H9 108.9 . . ?
C11 C10 C15 120.4(5) . . ?
C11 C10 N4 120.2(5) . . ?
C15 C10 N4 119.3(5) . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.5(5) . . ?
C12 C13 Br1 120.7(5) . . ?
C14 C13 Br1 118.7(5) . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 119.7(5) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
N4 C16 C19 124.1(4) . . ?
N4 C16 C17 112.4(4) . . ?
C19 C16 C17 123.5(5) . . ?
O4 C17 O5 125.8(5) . . ?
O4 C17 C16 123.6(5) . . ?
O5 C17 C16 110.3(5) . . ?
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 . . ?
C16 C19 C20 124.6(4) . . ?
C16 C19 C22 121.7(4) . . ?
C20 C19 C22 113.7(4) . . ?
O2 C20 O3 123.2(5) . . ?
O2 C20 C19 123.5(5) . . ?
O3 C20 C19 113.3(5) . . ?
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 . . ?
C36 C22 C19 116.0(4) . . ?
C36 C22 C23 100.6(4) . . ?
C19 C22 C23 112.6(4) . . ?
C36 C22 C37 111.7(4) . . ?
C19 C22 C37 108.3(3) . . ?
C23 C22 C37 107.1(4) . . ?
O1 C23 N3 126.4(5) . . ?
O1 C23 C22 125.0(5) . . ?
N3 C23 C22 108.4(5) . . ?
N3 C24 C25 115.1(5) . . ?
N3 C24 H24A 108.5 . . ?
C25 C24 H24A 108.5 . . ?
N3 C24 H24B 108.5 . . ?
C25 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?
C26 C25 C30 118.5(7) . . ?
C26 C25 C24 123.4(6) . . ?
C30 C25 C24 118.1(7) . . ?
C25 C26 C27 122.6(7) . . ?
C25 C26 H26 118.7 . . ?
C27 C26 H26 118.7 . . ?
C28 C27 C26 119.3(9) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C27 C28 C29 120.6(10) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C30 120.1(9) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 118.8(8) . . ?
C25 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C32 C31 C36 121.9(5) . . ?
C32 C31 N3 128.1(5) . . ?
C36 C31 N3 109.9(4) . . ?
C33 C32 C31 117.4(5) . . ?
C33 C32 H32 121.3 . . ?
C31 C32 H32 121.3 . . ?
C34 C33 C32 121.3(6) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C33 C34 C35 120.9(6) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 119.0(5) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C35 C36 C31 119.4(5) . . ?
C35 C36 C22 131.7(4) . . ?
C31 C36 C22 108.9(4) . . ?
C38 C37 C39 108.1(4) . . ?
C38 C37 C22 112.6(4) . . ?
C39 C37 C22 110.1(4) . . ?
C38 C37 C9 108.4(4) . . ?
C39 C37 C9 107.2(4) . . ?
C22 C37 C9 110.3(4) . . ?
N1 C38 C37 176.1(6) . . ?
N2 C39 C37 178.9(6) . . ?
C45 C40 C41 122.0(5) . . ?
C45 C40 Br2 118.7(5) . . ?
C41 C40 Br2 119.3(5) . . ?
C42 C41 C40 118.3(5) . . ?
C42 C41 H41 120.8 . . ?
C40 C41 H41 120.8 . . ?
C43 C42 C41 120.6(5) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C44 C43 C42 120.3(5) . . ?
C44 C43 N5 119.8(5) . . ?
C42 C43 N5 119.8(5) . . ?
C43 C44 C45 119.8(5) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C40 C45 C44 118.9(5) . . ?
C40 C45 H45 120.5 . . ?
C44 C45 H45 120.5 . . ?
N5 C46 C47 113.1(4) . . ?
N5 C46 C55 105.8(4) . . ?
C47 C46 C55 111.3(4) . . ?
N5 C46 H46 108.8 . . ?
C47 C46 H46 108.8 . . ?
C55 C46 H46 108.8 . . ?
C48 C47 C46 122.8(5) . . ?
C48 C47 H47 118.6 . . ?
C46 C47 H47 118.6 . . ?
C47 C48 C49 126.5(5) . . ?
C47 C48 H48 116.7 . . ?
C49 C48 H48 116.7 . . ?
C54 C49 C50 118.9(5) . . ?
C54 C49 C48 122.8(5) . . ?
C50 C49 C48 118.2(5) . . ?
C51 C50 C49 119.7(5) . . ?
C51 C50 H50 120.2 . . ?
C49 C50 H50 120.2 . . ?
C52 C51 C50 122.2(6) . . ?
C52 C51 Cl2 118.1(6) . . ?
C50 C51 Cl2 119.8(5) . . ?
C51 C52 C53 118.3(6) . . ?
C51 C52 H52 120.9 . . ?
C53 C52 H52 120.9 . . ?
C54 C53 C52 121.3(6) . . ?
C54 C53 H53 119.3 . . ?
C52 C53 H53 119.3 . . ?
C53 C54 C49 119.6(6) . . ?
C53 C54 H54 120.2 . . ?
C49 C54 H54 120.2 . . ?
C56 C55 C57 108.8(4) . . ?
C56 C55 C58 110.6(4) . . ?
C57 C55 C58 111.0(4) . . ?
C56 C55 C46 109.8(4) . . ?
C57 C55 C46 106.3(4) . . ?
C58 C55 C46 110.3(4) . . ?
N7 C56 C55 178.7(6) . . ?
N6 C57 C55 175.2(5) . . ?
C59 C58 C73 115.1(4) . . ?
C59 C58 C55 112.8(4) . . ?
C73 C58 C55 108.3(4) . . ?
C59 C58 C72 101.0(4) . . ?
C73 C58 C72 112.4(4) . . ?
C55 C58 C72 106.9(4) . . ?
C60 C59 C64 120.2(4) . . ?
C60 C59 C58 130.7(4) . . ?
C64 C59 C58 109.1(4) . . ?
C59 C60 C61 118.6(5) . . ?
C59 C60 H60 120.7 . . ?
C61 C60 H60 120.7 . . ?
C62 C61 C60 120.2(5) . . ?
C62 C61 H61 119.9 . . ?
C60 C61 H61 119.9 . . ?
C63 C62 C61 122.1(5) . . ?
C63 C62 H62 119.0 . . ?
C61 C62 H62 119.0 . . ?
C62 C63 C64 117.0(5) . . ?
C62 C63 H63 121.5 . . ?
C64 C63 H63 121.5 . . ?
C59 C64 C63 121.9(5) . . ?
C59 C64 N8 111.1(4) . . ?
C63 C64 N8 127.0(5) . . ?
N8 C65 C66 114.5(4) . . ?
N8 C65 H65A 108.6 . . ?
C66 C65 H65A 108.6 . . ?
N8 C65 H65B 108.6 . . ?
C66 C65 H65B 108.6 . . ?
H65A C65 H65B 107.6 . . ?
C67 C66 C71 118.5(5) . . ?
C67 C66 C65 122.4(5) . . ?
C71 C66 C65 119.2(5) . . ?
C66 C67 C68 120.0(6) . . ?
C66 C67 H67 120.0 . . ?
C68 C67 H67 120.0 . . ?
C69 C68 C67 120.2(7) . . ?
C69 C68 H68 119.9 . . ?
C67 C68 H68 119.9 . . ?
C70 C69 C68 120.1(7) . . ?
C70 C69 H69 120.0 . . ?
C68 C69 H69 120.0 . . ?
C69 C70 C71 120.9(6) . . ?
C69 C70 H70 119.6 . . ?
C71 C70 H70 119.6 . . ?
C70 C71 C66 120.4(6) . . ?
C70 C71 H71 119.8 . . ?
C66 C71 H71 119.8 . . ?
O10 C72 N8 125.6(5) . . ?
O10 C72 C58 125.9(5) . . ?
N8 C72 C58 108.4(5) . . ?
C76 C73 C74 123.5(5) . . ?
C76 C73 C58 121.3(5) . . ?
C74 C73 C58 115.0(4) . . ?
O8 C74 O9 123.0(5) . . ?
O8 C74 C73 122.8(5) . . ?
O9 C74 C73 114.2(5) . . ?
O9 C75 H75A 109.5 . . ?
O9 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
O9 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C73 C76 N5 124.0(4) . . ?
C73 C76 C77 121.7(5) . . ?
N5 C76 C77 114.2(4) . . ?
O6 C77 O7 126.4(5) . . ?
O6 C77 C76 121.8(5) . . ?
O7 C77 C76 111.7(5) . . ?
O7 C78 H78A 109.5 . . ?
O7 C78 H78B 109.5 . . ?
H78A C78 H78B 109.5 . . ?
O7 C78 H78C 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
C23 N3 C31 111.2(4) . . ?
C23 N3 C24 123.0(4) . . ?
C31 N3 C24 125.5(4) . . ?
C16 N4 C10 122.2(4) . . ?
C16 N4 C9 120.1(4) . . ?
C10 N4 C9 117.7(4) . . ?
C76 N5 C43 120.2(4) . . ?
C76 N5 C46 119.9(4) . . ?
C43 N5 C46 118.7(4) . . ?
C72 N8 C64 110.3(4) . . ?
C72 N8 C65 122.7(4) . . ?
C64 N8 C65 125.2(4) . . ?
C20 O3 C21 116.8(4) . . ?
C17 O5 C18 114.5(4) . . ?
C77 O7 C78 115.4(4) . . ?
C74 O9 C75 117.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.870
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.870
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_4c
_audit_block_doi                 10.5517/cc1j93wt
_database_code_depnum_ccdc_archive 'CCDC 1408946'
_audit_update_record             
;
2015-06-26 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H32 N4 O4'
_chemical_formula_sum            'C39 H32 N4 O4'
_chemical_formula_weight         620.69

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                   10.7565(16)
_cell_length_b                   12.240(2)
_cell_length_c                   14.678(2)
_cell_angle_alpha                82.406(5)
_cell_angle_beta                 69.137(5)
_cell_angle_gamma                64.352(5)
_cell_volume                     1627.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7142
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      26.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.982
_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            24921
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0746
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         27.64
_reflns_number_total             7430
_reflns_number_gt                4449
_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)+(0.0749P)²+0.1650P] 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         7430
_refine_ls_number_parameters     427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1575
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.6112(3) 1.3077(2) 0.1838(2) 0.0775(8) Uani 1 1 d . . .
H1 H 0.5144 1.3179 0.2119 0.093 Uiso 1 1 calc R . .
C2 C 0.6498(5) 1.3764(3) 0.1041(3) 0.1130(13) Uani 1 1 d . . .
H2 H 0.5789 1.4329 0.0795 0.136 Uiso 1 1 calc R . .
C3 C 0.7924(6) 1.3603(3) 0.0624(3) 0.1125(13) Uani 1 1 d . . .
H3 H 0.8183 1.4058 0.0090 0.135 Uiso 1 1 calc R . .
C4 C 0.8951(4) 1.2796(3) 0.0978(2) 0.0931(10) Uani 1 1 d . . .
H4 H 0.9918 1.2693 0.0688 0.112 Uiso 1 1 calc R . .
C5 C 0.8579(3) 1.2116(2) 0.17696(17) 0.0637(7) Uani 1 1 d . . .
H5 H 0.9301 1.1560 0.2010 0.076 Uiso 1 1 calc R . .
C6 C 0.7156(3) 1.22493(18) 0.22095(15) 0.0447(5) Uani 1 1 d . . .
C7 C 0.6746(2) 1.15587(17) 0.31070(14) 0.0397(5) Uani 1 1 d . . .
H7A H 0.6681 1.1950 0.3666 0.048 Uiso 1 1 calc R . .
H7B H 0.5786 1.1595 0.3212 0.048 Uiso 1 1 calc R . .
C8 C 0.88058(19) 0.98573(17) 0.34929(12) 0.0308(4) Uani 1 1 d . . .
C9 C 0.96050(18) 0.84592(16) 0.33129(12) 0.0280(4) Uani 1 1 d . . .
C10 C 0.89232(19) 0.82742(17) 0.26304(12) 0.0305(4) Uani 1 1 d . . .
C11 C 0.9183(2) 0.72428(18) 0.21679(13) 0.0385(5) Uani 1 1 d . . .
H11 H 0.9938 0.6507 0.2214 0.046 Uiso 1 1 calc R . .
C12 C 0.8310(2) 0.7309(2) 0.16312(14) 0.0460(5) Uani 1 1 d . . .
C13 C 0.8509(3) 0.6171(2) 0.11946(17) 0.0670(7) Uani 1 1 d . . .
H13A H 0.7609 0.6073 0.1450 0.100 Uiso 1 1 calc R . .
H13B H 0.9267 0.5484 0.1358 0.100 Uiso 1 1 calc R . .
H13C H 0.8778 0.6233 0.0498 0.100 Uiso 1 1 calc R . .
C14 C 0.7248(3) 0.8429(2) 0.15437(16) 0.0535(6) Uani 1 1 d . . .
H14 H 0.6674 0.8481 0.1179 0.064 Uiso 1 1 calc R . .
C15 C 0.6997(2) 0.9481(2) 0.19733(15) 0.0459(5) Uani 1 1 d . . .
H15 H 0.6286 1.0227 0.1893 0.055 Uiso 1 1 calc R . .
C16 C 0.7844(2) 0.93754(17) 0.25254(12) 0.0321(4) Uani 1 1 d . . .
C17 C 0.91138(18) 0.78702(16) 0.43246(12) 0.0266(4) Uani 1 1 d . . .
C18 C 0.7534(2) 0.85015(18) 0.48412(13) 0.0334(4) Uani 1 1 d . . .
C19 C 0.9479(2) 0.65827(18) 0.41538(12) 0.0316(4) Uani 1 1 d . . .
C20 C 1.2056(2) 0.72878(17) 0.35284(13) 0.0345(5) Uani 1 1 d . . .
H20 H 1.3064 0.6902 0.3227 0.041 Uiso 1 1 calc R . .
C21 C 1.12509(19) 0.79675(17) 0.29661(12) 0.0332(4) Uani 1 1 d . . .
C22 C 1.2048(2) 0.8217(2) 0.19810(14) 0.0462(5) Uani 1 1 d . . .
C23 C 1.1791(3) 0.9307(3) 0.05485(15) 0.0688(8) Uani 1 1 d . . .
H23A H 1.2323 0.9770 0.0539 0.103 Uiso 1 1 calc R . .
H23B H 1.1032 0.9772 0.0275 0.103 Uiso 1 1 calc R . .
H23C H 1.2446 0.8570 0.0171 0.103 Uiso 1 1 calc R . .
C24 C 0.6714(3) 0.8726(3) 0.84317(16) 0.0619(7) Uani 1 1 d . . .
H24 H 0.6537 0.9537 0.8317 0.074 Uiso 1 1 calc R . .
C25 C 0.5931(3) 0.8403(3) 0.93162(18) 0.0791(9) Uani 1 1 d . . .
H25 H 0.5216 0.9004 0.9780 0.095 Uiso 1 1 calc R . .
C26 C 0.6188(3) 0.7236(3) 0.95129(17) 0.0780(9) Uani 1 1 d . . .
H26 H 0.5671 0.7029 1.0113 0.094 Uiso 1 1 calc R . .
C27 C 0.7219(3) 0.6354(3) 0.88214(18) 0.0879(10) Uani 1 1 d . . .
H27 H 0.7390 0.5546 0.8949 0.105 Uiso 1 1 calc R . .
C28 C 0.8003(3) 0.6660(2) 0.79390(16) 0.0738(8) Uani 1 1 d . . .
H28 H 0.8713 0.6050 0.7482 0.089 Uiso 1 1 calc R . .
C29 C 0.7756(2) 0.7855(2) 0.77179(13) 0.0448(5) Uani 1 1 d . . .
C30 C 0.8520(2) 0.82012(18) 0.67616(13) 0.0396(5) Uani 1 1 d . . .
H30 H 0.8419 0.8999 0.6696 0.048 Uiso 1 1 calc R . .
C31 C 0.93403(19) 0.74715(17) 0.59869(12) 0.0314(4) Uani 1 1 d . . .
H31 H 0.9539 0.6652 0.6060 0.038 Uiso 1 1 calc R . .
C32 C 0.99663(18) 0.78915(16) 0.49989(12) 0.0288(4) Uani 1 1 d . . .
H32 H 0.9848 0.8723 0.5055 0.035 Uiso 1 1 calc R . .
C33 C 1.23467(18) 0.61250(17) 0.49742(12) 0.0306(4) Uani 1 1 d . . .
C34 C 1.2411(2) 0.63181(18) 0.58646(14) 0.0359(5) Uani 1 1 d . . .
H34 H 1.1952 0.7097 0.6136 0.043 Uiso 1 1 calc R . .
C35 C 1.3156(2) 0.53530(18) 0.63458(14) 0.0397(5) Uani 1 1 d . . .
H35 H 1.3183 0.5483 0.6947 0.048 Uiso 1 1 calc R . .
C36 C 1.3864(2) 0.41898(18) 0.59400(14) 0.0370(5) Uani 1 1 d . . .
C37 C 1.5245(3) 0.2083(2) 0.61363(18) 0.0592(6) Uani 1 1 d . . .
H37A H 1.4529 0.1879 0.6046 0.089 Uiso 1 1 calc R . .
H37B H 1.5639 0.1557 0.6605 0.089 Uiso 1 1 calc R . .
H37C H 1.6020 0.1989 0.5526 0.089 Uiso 1 1 calc R . .
C38 C 1.3822(2) 0.39974(18) 0.50521(14) 0.0392(5) Uani 1 1 d . . .
H38 H 1.4311 0.3222 0.4771 0.047 Uiso 1 1 calc R . .
C39 C 1.3046(2) 0.49671(18) 0.45754(14) 0.0378(5) Uani 1 1 d . . .
H39 H 1.2997 0.4833 0.3982 0.045 Uiso 1 1 calc R . .
N1 N 0.77803(16) 1.02951(13) 0.30487(10) 0.0318(4) Uani 1 1 d . . .
N2 N 0.6330(2) 0.89747(18) 0.52816(13) 0.0563(5) Uani 1 1 d . . .
N3 N 0.9830(2) 0.55854(17) 0.40083(13) 0.0500(5) Uani 1 1 d . . .
N4 N 1.15101(15) 0.71238(14) 0.44971(10) 0.0321(4) Uani 1 1 d . . .
O1 O 0.90242(15) 1.04532(12) 0.39724(10) 0.0437(4) Uani 1 1 d . . .
O2 O 1.33531(18) 0.7804(2) 0.16077(12) 0.0994(8) Uani 1 1 d . . .
O3 O 1.11480(15) 0.90221(13) 0.15385(9) 0.0487(4) Uani 1 1 d . . .
O4 O 1.45752(15) 0.33079(13) 0.64806(10) 0.0495(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 1.375(3) . ?
C1 C2 1.393(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.339(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(3) . ?
C7 N1 1.454(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.218(2) . ?
C8 N1 1.356(2) . ?
C8 C9 1.556(3) . ?
C9 C21 1.507(2) . ?
C9 C10 1.523(2) . ?
C9 C17 1.579(2) . ?
C10 C16 1.381(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.397(3) . ?
C11 H11 0.9300 . ?
C12 C14 1.380(3) . ?
C12 C13 1.509(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 N1 1.409(2) . ?
C17 C18 1.470(3) . ?
C17 C19 1.483(3) . ?
C17 C32 1.580(2) . ?
C18 N2 1.133(2) . ?
C19 N3 1.136(2) . ?
C20 C21 1.352(3) . ?
C20 N4 1.356(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.465(3) . ?
C22 O2 1.199(2) . ?
C22 O3 1.336(2) . ?
C23 O3 1.439(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C29 1.384(3) . ?
C24 C25 1.387(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.344(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.370(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.377(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.384(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.465(3) . ?
C30 C31 1.319(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.493(2) . ?
C31 H31 0.9300 . ?
C32 N4 1.464(2) . ?
C32 H32 0.9800 . ?
C33 C39 1.378(3) . ?
C33 C34 1.389(3) . ?
C33 N4 1.437(2) . ?
C34 C35 1.378(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.387(3) . ?
C35 H35 0.9300 . ?
C36 O4 1.368(2) . ?
C36 C38 1.374(3) . ?
C37 O4 1.424(3) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.391(3) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.3(3) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.2(3) . . ?
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 . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 C7 121.1(2) . . ?
C5 C6 C7 120.60(19) . . ?
N1 C7 C6 113.40(16) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 N1 125.76(18) . . ?
O1 C8 C9 126.44(16) . . ?
N1 C8 C9 107.76(15) . . ?
C21 C9 C10 116.89(14) . . ?
C21 C9 C8 114.28(14) . . ?
C10 C9 C8 101.62(14) . . ?
C21 C9 C17 107.35(14) . . ?
C10 C9 C17 109.55(13) . . ?
C8 C9 C17 106.65(13) . . ?
C16 C10 C11 119.92(17) . . ?
C16 C10 C9 108.50(15) . . ?
C11 C10 C9 131.55(17) . . ?
C10 C11 C12 119.93(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C14 C12 C11 118.04(19) . . ?
C14 C12 C13 121.8(2) . . ?
C11 C12 C13 120.1(2) . . ?
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 123.13(19) . . ?
C12 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C16 C15 C14 117.3(2) . . ?
C16 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
C15 C16 C10 121.63(18) . . ?
C15 C16 N1 128.15(18) . . ?
C10 C16 N1 110.22(15) . . ?
C18 C17 C19 109.03(15) . . ?
C18 C17 C9 111.72(14) . . ?
C19 C17 C9 109.04(13) . . ?
C18 C17 C32 108.79(14) . . ?
C19 C17 C32 107.39(14) . . ?
C9 C17 C32 110.76(13) . . ?
N2 C18 C17 176.6(2) . . ?
N3 C19 C17 176.6(2) . . ?
C21 C20 N4 125.18(17) . . ?
C21 C20 H20 117.4 . . ?
N4 C20 H20 117.4 . . ?
C20 C21 C22 117.05(17) . . ?
C20 C21 C9 122.82(16) . . ?
C22 C21 C9 120.13(16) . . ?
O2 C22 O3 122.24(18) . . ?
O2 C22 C21 125.68(19) . . ?
O3 C22 C21 112.01(17) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C25 120.8(3) . . ?
C29 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 119.5(3) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C26 C27 C28 120.2(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C29 121.4(2) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C24 C29 C28 117.1(2) . . ?
C24 C29 C30 120.8(2) . . ?
C28 C29 C30 122.07(19) . . ?
C31 C30 C29 125.2(2) . . ?
C31 C30 H30 117.4 . . ?
C29 C30 H30 117.4 . . ?
C30 C31 C32 123.44(18) . . ?
C30 C31 H31 118.3 . . ?
C32 C31 H31 118.3 . . ?
N4 C32 C31 114.16(14) . . ?
N4 C32 C17 105.92(13) . . ?
C31 C32 C17 108.98(14) . . ?
N4 C32 H32 109.2 . . ?
C31 C32 H32 109.2 . . ?
C17 C32 H32 109.2 . . ?
C39 C33 C34 119.45(17) . . ?
C39 C33 N4 120.74(16) . . ?
C34 C33 N4 119.77(17) . . ?
C35 C34 C33 119.90(18) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 120.51(18) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
O4 C36 C38 124.99(19) . . ?
O4 C36 C35 115.23(17) . . ?
C38 C36 C35 119.77(18) . . ?
O4 C37 H37A 109.5 . . ?
O4 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O4 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 C39 119.76(19) . . ?
C36 C38 H38 120.1 . . ?
C39 C38 H38 120.1 . . ?
C33 C39 C38 120.59(17) . . ?
C33 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C8 N1 C16 111.63(15) . . ?
C8 N1 C7 123.95(16) . . ?
C16 N1 C7 124.42(15) . . ?
C20 N4 C33 121.09(15) . . ?
C20 N4 C32 116.99(14) . . ?
C33 N4 C32 121.29(13) . . ?
C22 O3 C23 117.57(16) . . ?
C36 O4 C37 118.07(16) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.081

#=====================================================================
####################################################################### 
# 
# 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_zj150724
_audit_block_doi                 10.5517/cc1jhlf1
_database_code_depnum_ccdc_archive 'CCDC 1415163'
_audit_update_record             
;
2015-09-23 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H25 N3 O6'
_chemical_formula_sum            'C34 H25 N3 O6'
_chemical_formula_weight         571.57

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                   10.963(2)
_cell_length_b                   12.057(3)
_cell_length_c                   12.362(3)
_cell_angle_alpha                83.195(8)
_cell_angle_beta                 66.986(7)
_cell_angle_gamma                81.841(7)
_cell_volume                     1485.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4812
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      22.96

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.981
_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            22725
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0979
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.57
_reflns_number_total             6786
_reflns_number_gt                3148
_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)+(0.0703P)²+0.3611P] 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         6786
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1758
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.5570(3) 0.0918(2) 0.1620(3) 0.0465(6) Uani 1 1 d . . .
C2 C 0.4644(3) 0.0079(2) 0.2230(3) 0.0521(7) Uani 1 1 d . . .
C3 C 0.4313(4) -0.0764(3) 0.1763(3) 0.0822(10) Uani 1 1 d . . .
H3 H 0.4710 -0.0872 0.0961 0.099 Uiso 1 1 calc R . .
C4 C 0.3392(5) -0.1429(3) 0.2507(5) 0.1167(16) Uani 1 1 d . . .
H4 H 0.3136 -0.1986 0.2206 0.140 Uiso 1 1 calc R . .
C5 C 0.2833(4) -0.1299(3) 0.3688(5) 0.1189(16) Uani 1 1 d . . .
H5 H 0.2228 -0.1789 0.4175 0.143 Uiso 1 1 calc R . .
C6 C 0.3139(3) -0.0458(3) 0.4187(3) 0.0867(10) Uani 1 1 d . . .
H6 H 0.2751 -0.0365 0.4991 0.104 Uiso 1 1 calc R . .
C7 C 0.4060(3) 0.0236(2) 0.3413(3) 0.0537(7) Uani 1 1 d . . .
C8 C 0.4492(2) 0.1231(2) 0.3678(2) 0.0458(6) Uani 1 1 d . . .
C9 C 0.5354(2) 0.18140(18) 0.24947(19) 0.0374(6) Uani 1 1 d . . .
C10 C 0.4509(2) 0.28772(19) 0.2185(2) 0.0383(6) Uani 1 1 d . . .
C11 C 0.3170(3) 0.2607(2) 0.2366(2) 0.0508(7) Uani 1 1 d . . .
C12 C 0.5150(3) 0.3278(2) 0.0944(3) 0.0472(6) Uani 1 1 d . . .
C13 C 0.4376(2) 0.38591(19) 0.2967(2) 0.0442(6) Uani 1 1 d . . .
H13 H 0.4008 0.3583 0.3797 0.053 Uiso 1 1 calc R . .
C14 C 0.3459(2) 0.4836(2) 0.2772(2) 0.0466(6) Uani 1 1 d . . .
H14 H 0.3701 0.5207 0.2027 0.056 Uiso 1 1 calc R . .
C15 C 0.2334(3) 0.5194(2) 0.3597(2) 0.0473(6) Uani 1 1 d . . .
H15 H 0.2152 0.4851 0.4350 0.057 Uiso 1 1 calc R . .
C16 C 0.1329(2) 0.60842(19) 0.3455(2) 0.0464(6) Uani 1 1 d . . .
C17 C 0.1355(2) 0.6500(2) 0.2348(2) 0.0499(7) Uani 1 1 d . . .
H17 H 0.2029 0.6209 0.1683 0.060 Uiso 1 1 calc R . .
C18 C 0.0412(3) 0.7333(2) 0.2203(3) 0.0552(7) Uani 1 1 d . . .
C19 C 0.0477(3) 0.7772(3) 0.0989(3) 0.0837(10) Uani 1 1 d . . .
H19A H 0.1293 0.8106 0.0570 0.126 Uiso 1 1 calc R . .
H19B H -0.0266 0.8326 0.1056 0.126 Uiso 1 1 calc R . .
H19C H 0.0444 0.7164 0.0569 0.126 Uiso 1 1 calc R . .
C20 C -0.0591(3) 0.7746(2) 0.3196(3) 0.0661(8) Uani 1 1 d . . .
H20 H -0.1247 0.8293 0.3120 0.079 Uiso 1 1 calc R . .
C21 C -0.0631(3) 0.7355(3) 0.4297(3) 0.0723(9) Uani 1 1 d . . .
H21 H -0.1306 0.7649 0.4959 0.087 Uiso 1 1 calc R . .
C22 C 0.0321(3) 0.6530(2) 0.4434(3) 0.0614(8) Uani 1 1 d . . .
H22 H 0.0283 0.6273 0.5185 0.074 Uiso 1 1 calc R . .
C23 C 0.6700(3) 0.5716(3) 0.1384(3) 0.0763(9) Uani 1 1 d . . .
H23 H 0.6935 0.5270 0.0754 0.092 Uiso 1 1 calc R . .
C24 C 0.7054(4) 0.6787(4) 0.1170(5) 0.1118(15) Uani 1 1 d . . .
H24 H 0.7514 0.7069 0.0405 0.134 Uiso 1 1 calc R . .
C25 C 0.6731(5) 0.7416(4) 0.2069(7) 0.1216(19) Uani 1 1 d . . .
H25 H 0.7011 0.8131 0.1922 0.146 Uiso 1 1 calc R . .
C26 C 0.6013(6) 0.7066(4) 0.3191(6) 0.1270(18) Uani 1 1 d . . .
H26 H 0.5775 0.7533 0.3804 0.152 Uiso 1 1 calc R . .
C27 C 0.5628(4) 0.5943(3) 0.3406(4) 0.1014(13) Uani 1 1 d . . .
H27 H 0.5122 0.5672 0.4164 0.122 Uiso 1 1 calc R . .
C28 C 0.6012(3) 0.5286(2) 0.2493(3) 0.0521(7) Uani 1 1 d . . .
C29 C 0.6714(2) 0.3274(2) 0.2579(2) 0.0441(6) Uani 1 1 d . . .
C30 C 0.7916(3) 0.3668(2) 0.2683(3) 0.0564(7) Uani 1 1 d . . .
C31 C 0.9910(3) 0.4440(3) 0.1713(4) 0.1106(14) Uani 1 1 d . . .
H31A H 0.9547 0.5087 0.2165 0.166 Uiso 1 1 calc R . .
H31B H 1.0496 0.4667 0.0932 0.166 Uiso 1 1 calc R . .
H31C H 1.0399 0.3918 0.2083 0.166 Uiso 1 1 calc R . .
C32 C 0.6598(2) 0.21855(19) 0.2507(2) 0.0411(6) Uani 1 1 d . . .
C33 C 0.7618(3) 0.1258(2) 0.2501(2) 0.0527(7) Uani 1 1 d . . .
C34 C 0.9821(3) 0.0741(3) 0.2407(5) 0.1265(18) Uani 1 1 d . . .
H34A H 0.9511 0.0173 0.3035 0.190 Uiso 1 1 calc R . .
H34B H 1.0521 0.1078 0.2489 0.190 Uiso 1 1 calc R . .
H34C H 1.0155 0.0409 0.1664 0.190 Uiso 1 1 calc R . .
N1 N 0.2143(3) 0.2403(2) 0.2506(3) 0.0809(8) Uani 1 1 d . . .
N2 N 0.5623(3) 0.3629(2) -0.0002(2) 0.0737(8) Uani 1 1 d . . .
N3 N 0.57229(19) 0.41322(15) 0.26839(18) 0.0472(5) Uani 1 1 d . . .
O1 O 0.6330(2) 0.09573(16) 0.06065(18) 0.0704(6) Uani 1 1 d . . .
O2 O 0.4214(2) 0.15775(17) 0.46251(18) 0.0737(6) Uani 1 1 d . . .
O3 O 0.7940(2) 0.37892(19) 0.3614(2) 0.0892(7) Uani 1 1 d . . .
O4 O 0.88286(19) 0.39065(15) 0.1649(2) 0.0679(6) Uani 1 1 d . . .
O5 O 0.74524(18) 0.02839(15) 0.25531(18) 0.0665(6) Uani 1 1 d . . .
O6 O 0.8736(2) 0.15890(15) 0.2459(2) 0.0961(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.203(3) . ?
C1 C2 1.461(4) . ?
C1 C9 1.548(3) . ?
C2 C7 1.372(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.355(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.466(4) . ?
C8 O2 1.199(3) . ?
C8 C9 1.546(3) . ?
C9 C32 1.501(3) . ?
C9 C10 1.572(3) . ?
C10 C12 1.469(4) . ?
C10 C11 1.474(3) . ?
C10 C13 1.571(3) . ?
C11 N1 1.129(3) . ?
C12 N2 1.134(3) . ?
C13 N3 1.455(3) . ?
C13 C14 1.497(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.311(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.472(3) . ?
C15 H15 0.9300 . ?
C16 C22 1.384(3) . ?
C16 C17 1.391(4) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C18 C20 1.378(4) . ?
C18 C19 1.509(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.372(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C28 1.361(4) . ?
C23 C24 1.366(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.324(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.351(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.439(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.349(4) . ?
C27 H27 0.9300 . ?
C28 N3 1.443(3) . ?
C29 C32 1.352(3) . ?
C29 N3 1.368(3) . ?
C29 C30 1.518(4) . ?
C30 O3 1.187(3) . ?
C30 O4 1.309(3) . ?
C31 O4 1.458(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.463(3) . ?
C33 O5 1.204(3) . ?
C33 O6 1.323(3) . ?
C34 O6 1.440(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 127.4(2) . . ?
O1 C1 C9 124.7(2) . . ?
C2 C1 C9 107.8(2) . . ?
C7 C2 C3 120.9(3) . . ?
C7 C2 C1 110.4(2) . . ?
C3 C2 C1 128.7(3) . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 122.0(4) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C7 116.1(4) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
C2 C7 C6 121.5(3) . . ?
C2 C7 C8 110.7(2) . . ?
C6 C7 C8 127.7(3) . . ?
O2 C8 C7 127.8(2) . . ?
O2 C8 C9 124.5(2) . . ?
C7 C8 C9 107.7(2) . . ?
C32 C9 C8 113.50(19) . . ?
C32 C9 C1 115.65(19) . . ?
C8 C9 C1 101.77(19) . . ?
C32 C9 C10 108.10(18) . . ?
C8 C9 C10 109.22(18) . . ?
C1 C9 C10 108.32(17) . . ?
C12 C10 C11 107.48(19) . . ?
C12 C10 C13 107.97(19) . . ?
C11 C10 C13 109.41(19) . . ?
C12 C10 C9 110.66(19) . . ?
C11 C10 C9 110.72(19) . . ?
C13 C10 C9 110.51(17) . . ?
N1 C11 C10 179.8(4) . . ?
N2 C12 C10 177.3(3) . . ?
N3 C13 C14 113.59(19) . . ?
N3 C13 C10 106.38(18) . . ?
C14 C13 C10 111.14(19) . . ?
N3 C13 H13 108.5 . . ?
C14 C13 H13 108.5 . . ?
C10 C13 H13 108.5 . . ?
C15 C14 C13 123.4(2) . . ?
C15 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
C14 C15 C16 126.8(2) . . ?
C14 C15 H15 116.6 . . ?
C16 C15 H15 116.6 . . ?
C22 C16 C17 118.0(2) . . ?
C22 C16 C15 120.3(2) . . ?
C17 C16 C15 121.7(2) . . ?
C18 C17 C16 122.2(3) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C20 C18 C17 118.2(3) . . ?
C20 C18 C19 120.9(3) . . ?
C17 C18 C19 120.9(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C18 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C18 C20 H20 119.7 . . ?
C20 C21 C22 120.9(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C16 120.1(3) . . ?
C21 C22 H22 120.0 . . ?
C16 C22 H22 120.0 . . ?
C28 C23 C24 121.7(4) . . ?
C28 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C25 C24 C23 119.0(5) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 122.9(5) . . ?
C24 C25 H25 118.6 . . ?
C26 C25 H25 118.6 . . ?
C25 C26 C27 117.7(4) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C28 C27 C26 119.2(4) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C27 C28 C23 119.4(3) . . ?
C27 C28 N3 120.8(3) . . ?
C23 C28 N3 119.8(3) . . ?
C32 C29 N3 124.5(2) . . ?
C32 C29 C30 123.5(2) . . ?
N3 C29 C30 111.7(2) . . ?
O3 C30 O4 126.6(3) . . ?
O3 C30 C29 121.5(3) . . ?
O4 C30 C29 111.8(3) . . ?
O4 C31 H31A 109.5 . . ?
O4 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O4 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 C33 124.2(2) . . ?
C29 C32 C9 122.1(2) . . ?
C33 C32 C9 113.6(2) . . ?
O5 C33 O6 122.9(2) . . ?
O5 C33 C32 123.6(2) . . ?
O6 C33 C32 113.5(2) . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C29 N3 C28 120.7(2) . . ?
C29 N3 C13 118.73(19) . . ?
C28 N3 C13 120.60(19) . . ?
C30 O4 C31 113.3(3) . . ?
C33 O6 C34 117.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
