# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_psu-24-md-306
_database_code_depnum_ccdc_archive 'CCDC 1457141'
_audit_update_record             
;
2016-03-02 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H36 N4 O8'
_chemical_formula_sum            'C50 H36 N4 O8'
_chemical_formula_weight         820.83

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.0225(15)
_cell_length_b                   19.081(6)
_cell_length_c                   21.963(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.606(13)
_cell_angle_gamma                90.00
_cell_volume                     4191.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5691
_cell_measurement_theta_min      3.4230
_cell_measurement_theta_max      26.3150

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Ruby'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31691
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         29.70
_reflns_number_total             10203
_reflns_number_gt                5452
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0731P)²+0.0000P] 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         10203
_refine_ls_number_parameters     561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1614
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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
O4 O 0.63516(11) 0.23392(7) 0.10264(5) 0.0380(3) Uani 1 1 d . . .
O5 O 0.66309(11) 0.17588(7) 0.21215(5) 0.0368(3) Uani 1 1 d . . .
O3 O 0.23283(14) -0.01959(9) 0.14532(7) 0.0615(4) Uani 1 1 d . . .
O6 O 0.79051(15) 0.19465(9) -0.06651(6) 0.0638(4) Uani 1 1 d . . .
N4 N 0.79940(14) 0.14790(8) 0.13116(6) 0.0375(4) Uani 1 1 d . . .
N3 N 0.49442(14) 0.14399(8) 0.13615(6) 0.0386(4) Uani 1 1 d . . .
O7 O 1.07669(13) 0.06019(9) 0.03146(6) 0.0573(4) Uani 1 1 d . . .
N2 N 0.90983(14) 0.11726(9) 0.10930(6) 0.0409(4) Uani 1 1 d . . .
O2 O 0.20752(15) 0.02189(9) 0.23892(7) 0.0680(5) Uani 1 1 d . . .
O1 O 0.49426(16) -0.00750(9) 0.28913(7) 0.0689(5) Uani 1 1 d . . .
O8 O 1.07334(16) 0.15915(11) -0.02155(8) 0.0820(6) Uani 1 1 d . . .
N1 N 0.38491(14) 0.10145(9) 0.12848(7) 0.0440(4) Uani 1 1 d . . .
C20 C 0.89740(17) 0.19793(11) 0.22457(7) 0.0387(5) Uani 1 1 d . . .
C13 C 0.79261(17) 0.14640(10) 0.19868(7) 0.0365(4) Uani 1 1 d . . .
C9 C 0.37849(17) 0.06879(11) 0.18143(8) 0.0416(5) Uani 1 1 d . . .
C38 C 0.50353(17) 0.20241(11) 0.09155(7) 0.0386(4) Uani 1 1 d . . .
C1 C 0.6018(3) 0.1778(2) 0.44363(13) 0.1004(11) Uani 1 1 d . . .
H1 H 0.6263 0.2036 0.4785 0.121 Uiso 1 1 calc R . .
C14 C 0.80564(17) 0.07250(11) 0.22288(8) 0.0412(5) Uani 1 1 d . . .
C2 C 0.5997(3) 0.1058(2) 0.44610(12) 0.1133(13) Uani 1 1 d . . .
H2 H 0.6206 0.0833 0.4830 0.136 Uiso 1 1 calc R . .
C39 C 0.48819(17) 0.17379(11) 0.02692(8) 0.0394(5) Uani 1 1 d . . .
C12 C 0.55218(17) 0.13806(10) 0.19377(7) 0.0366(4) Uani 1 1 d . . .
C10 C 0.26460(19) 0.02141(11) 0.19245(9) 0.0453(5) Uani 1 1 d . . .
C8 C 0.48032(17) 0.08970(10) 0.22436(7) 0.0382(4) Uani 1 1 d . . .
C35 C 0.6712(4) 0.4022(2) -0.08454(18) 0.1234(13) Uani 1 1 d . . .
H35 H 0.6397 0.4201 -0.1221 0.148 Uiso 1 1 calc R . .
C40 C 0.53610(17) 0.10762(12) 0.01296(8) 0.0443(5) Uani 1 1 d . . .
H40 H 0.5713 0.0789 0.0442 0.053 Uiso 1 1 calc R . .
C21 C 0.8685(2) 0.26830(12) 0.22943(9) 0.0505(5) Uani 1 1 d . . .
H21 H 0.7818 0.2840 0.2199 0.061 Uiso 1 1 calc R . .
C45 C 0.40386(17) 0.25992(11) 0.10568(8) 0.0415(5) Uani 1 1 d . . .
C37 C 0.74476(17) 0.19534(10) 0.09045(7) 0.0365(4) Uani 1 1 d . . .
C4 C 0.53678(19) 0.10018(13) 0.33994(8) 0.0509(6) Uani 1 1 d . . .
C22 C 0.9671(2) 0.31586(13) 0.24834(10) 0.0654(7) Uani 1 1 d . . .
H22 H 0.9470 0.3633 0.2509 0.079 Uiso 1 1 calc R . .
C44 C 0.4361(2) 0.21619(13) -0.01962(8) 0.0537(6) Uani 1 1 d . . .
H44 H 0.4040 0.2606 -0.0111 0.064 Uiso 1 1 calc R . .
C27 C 1.03001(18) 0.12290(12) 0.01671(8) 0.0450(5) Uani 1 1 d . . .
C26 C 0.91784(17) 0.14414(11) 0.05391(8) 0.0404(5) Uani 1 1 d . . .
C41 C 0.53203(19) 0.08413(13) -0.04650(9) 0.0532(6) Uani 1 1 d . . .
H41 H 0.5647 0.0399 -0.0553 0.064 Uiso 1 1 calc R . .
C50 C 0.26831(19) 0.24640(13) 0.09992(9) 0.0571(6) Uani 1 1 d . . .
H50 H 0.2385 0.2024 0.0871 0.069 Uiso 1 1 calc R . .
C15 C 0.7764(2) 0.01396(12) 0.18666(10) 0.0523(5) Uani 1 1 d . . .
H15 H 0.7495 0.0196 0.1457 0.063 Uiso 1 1 calc R . .
C7 C 0.50521(18) 0.05607(13) 0.28560(8) 0.0470(5) Uani 1 1 d . . .
C29 C 0.81670(17) 0.19436(11) 0.03945(7) 0.0390(5) Uani 1 1 d . . .
C5 C 0.5354(2) 0.17255(14) 0.33791(9) 0.0594(6) Uani 1 1 d . . .
H5 H 0.5126 0.1953 0.3013 0.071 Uiso 1 1 calc R . .
C25 C 1.02794(19) 0.17585(12) 0.23818(9) 0.0525(5) Uani 1 1 d . . .
H25 H 1.0498 0.1288 0.2339 0.063 Uiso 1 1 calc R . .
C30 C 0.78559(18) 0.22946(12) -0.02022(8) 0.0449(5) Uani 1 1 d . . .
C28 C 1.1891(2) 0.03589(14) -0.00102(10) 0.0678(7) Uani 1 1 d . . .
H28A H 1.1653 0.0358 -0.0441 0.102 Uiso 1 1 calc R . .
H28B H 1.2125 -0.0108 0.0121 0.102 Uiso 1 1 calc R . .
H28C H 1.2639 0.0665 0.0074 0.102 Uiso 1 1 calc R . .
C23 C 1.0949(2) 0.29251(17) 0.26335(10) 0.0719(8) Uani 1 1 d . . .
H23 H 1.1607 0.3241 0.2772 0.086 Uiso 1 1 calc R . .
C19 C 0.84050(19) 0.06316(13) 0.28436(9) 0.0557(6) Uani 1 1 d . . .
H19 H 0.8569 0.1019 0.3095 0.067 Uiso 1 1 calc R . .
C49 C 0.1762(2) 0.29728(16) 0.11297(10) 0.0672(7) Uani 1 1 d . . .
H49 H 0.0854 0.2872 0.1087 0.081 Uiso 1 1 calc R . .
C31 C 0.7506(2) 0.30486(12) -0.02295(9) 0.0521(5) Uani 1 1 d . . .
C43 C 0.4322(2) 0.19178(16) -0.07936(9) 0.0676(7) Uani 1 1 d . . .
H43 H 0.3971 0.2202 -0.1108 0.081 Uiso 1 1 calc R . .
C6 C 0.5678(3) 0.21135(17) 0.38983(11) 0.0810(8) Uani 1 1 d . . .
H6 H 0.5665 0.2601 0.3882 0.097 Uiso 1 1 calc R . .
C32 C 0.7695(2) 0.34906(14) 0.02614(11) 0.0687(7) Uani 1 1 d . . .
H32 H 0.8046 0.3318 0.0634 0.082 Uiso 1 1 calc R . .
C16 C 0.7872(2) -0.05274(14) 0.21139(13) 0.0698(7) Uani 1 1 d . . .
H16 H 0.7683 -0.0918 0.1870 0.084 Uiso 1 1 calc R . .
C42 C 0.4796(2) 0.12631(15) -0.09254(9) 0.0623(7) Uani 1 1 d . . .
H42 H 0.4761 0.1106 -0.1327 0.075 Uiso 1 1 calc R . .
C34 C 0.6872(4) 0.4452(2) -0.0354(2) 0.1279(13) Uani 1 1 d . . .
H34 H 0.6648 0.4924 -0.0396 0.153 Uiso 1 1 calc R . .
C24 C 1.1256(2) 0.22303(16) 0.25806(10) 0.0670(7) Uani 1 1 d . . .
H24 H 1.2123 0.2076 0.2679 0.080 Uiso 1 1 calc R . .
C3 C 0.5670(3) 0.06660(18) 0.39477(10) 0.0869(9) Uani 1 1 d . . .
H3 H 0.5653 0.0179 0.3970 0.104 Uiso 1 1 calc R . .
C48 C 0.2174(3) 0.36211(16) 0.13204(11) 0.0717(7) Uani 1 1 d . . .
H48 H 0.1552 0.3962 0.1408 0.086 Uiso 1 1 calc R . .
C17 C 0.8258(2) -0.06085(16) 0.27174(15) 0.0828(9) Uani 1 1 d . . .
H17 H 0.8351 -0.1057 0.2881 0.099 Uiso 1 1 calc R . .
C46 C 0.4443(2) 0.32544(14) 0.12482(12) 0.0716(7) Uani 1 1 d . . .
H46 H 0.5350 0.3359 0.1290 0.086 Uiso 1 1 calc R . .
C36 C 0.7017(3) 0.33220(16) -0.07863(12) 0.0837(8) Uani 1 1 d . . .
H36 H 0.6894 0.3028 -0.1123 0.100 Uiso 1 1 calc R . .
C18 C 0.8510(2) -0.00375(16) 0.30848(12) 0.0750(8) Uani 1 1 d . . .
H18 H 0.8752 -0.0100 0.3497 0.090 Uiso 1 1 calc R . .
C47 C 0.3510(3) 0.37642(16) 0.13813(15) 0.0915(9) Uani 1 1 d . . .
H47 H 0.3799 0.4205 0.1512 0.110 Uiso 1 1 calc R . .
C33 C 0.7361(3) 0.42032(17) 0.02029(16) 0.1016(10) Uani 1 1 d . . .
H33 H 0.7469 0.4502 0.0537 0.122 Uiso 1 1 calc R . .
C11 C 0.1136(2) -0.06189(15) 0.14964(12) 0.0805(8) Uani 1 1 d . . .
H11A H 0.1187 -0.0867 0.1877 0.121 Uiso 1 1 calc R . .
H11B H 0.1070 -0.0948 0.1166 0.121 Uiso 1 1 calc R . .
H11C H 0.0363 -0.0321 0.1475 0.121 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O4 C37 1.363(2) . ?
O4 C38 1.456(2) . ?
O5 C12 1.365(2) . ?
O5 C13 1.462(2) . ?
O3 C10 1.320(2) . ?
O3 C11 1.450(3) . ?
O6 C30 1.218(2) . ?
N4 C37 1.363(2) . ?
N4 N2 1.3653(19) . ?
N4 C13 1.489(2) . ?
N3 C12 1.363(2) . ?
N3 N1 1.367(2) . ?
N3 C38 1.491(2) . ?
O7 C27 1.318(3) . ?
O7 C28 1.447(2) . ?
N2 C26 1.327(2) . ?
O2 C10 1.201(2) . ?
O1 C7 1.221(3) . ?
O8 C27 1.191(2) . ?
N1 C9 1.324(2) . ?
C20 C21 1.379(3) . ?
C20 C25 1.389(3) . ?
C20 C13 1.522(3) . ?
C13 C14 1.510(3) . ?
C9 C8 1.403(2) . ?
C9 C10 1.488(3) . ?
C38 C39 1.520(2) . ?
C38 C45 1.529(3) . ?
C1 C6 1.368(4) . ?
C1 C2 1.375(5) . ?
C1 H1 0.9300 . ?
C14 C19 1.385(2) . ?
C14 C15 1.392(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C39 C44 1.380(3) . ?
C39 C40 1.392(3) . ?
C12 C8 1.372(3) . ?
C8 C7 1.497(3) . ?
C35 C34 1.356(5) . ?
C35 C36 1.375(4) . ?
C35 H35 0.9300 . ?
C40 C41 1.379(3) . ?
C40 H40 0.9300 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9300 . ?
C45 C46 1.372(3) . ?
C45 C50 1.381(3) . ?
C37 C29 1.370(2) . ?
C4 C3 1.381(3) . ?
C4 C5 1.382(3) . ?
C4 C7 1.478(3) . ?
C22 C23 1.377(3) . ?
C22 H22 0.9300 . ?
C44 C43 1.391(3) . ?
C44 H44 0.9300 . ?
C27 C26 1.487(3) . ?
C26 C29 1.416(3) . ?
C41 C42 1.371(3) . ?
C41 H41 0.9300 . ?
C50 C49 1.382(3) . ?
C50 H50 0.9300 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C29 C30 1.487(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C25 C24 1.380(3) . ?
C25 H25 0.9300 . ?
C30 C31 1.481(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C23 C24 1.368(4) . ?
C23 H23 0.9300 . ?
C19 C18 1.384(3) . ?
C19 H19 0.9300 . ?
C49 C48 1.362(4) . ?
C49 H49 0.9300 . ?
C31 C32 1.373(3) . ?
C31 C36 1.390(3) . ?
C43 C42 1.374(3) . ?
C43 H43 0.9300 . ?
C6 H6 0.9300 . ?
C32 C33 1.404(4) . ?
C32 H32 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C42 H42 0.9300 . ?
C34 C33 1.374(5) . ?
C34 H34 0.9300 . ?
C24 H24 0.9300 . ?
C3 H3 0.9300 . ?
C48 C47 1.364(3) . ?
C48 H48 0.9300 . ?
C17 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C46 C47 1.393(3) . ?
C46 H46 0.9300 . ?
C36 H36 0.9300 . ?
C18 H18 0.9300 . ?
C47 H47 0.9300 . ?
C33 H33 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C37 O4 C38 118.49(14) . . ?
C12 O5 C13 116.97(14) . . ?
C10 O3 C11 115.95(16) . . ?
C37 N4 N2 110.79(13) . . ?
C37 N4 C13 128.65(15) . . ?
N2 N4 C13 115.52(13) . . ?
C12 N3 N1 110.85(14) . . ?
C12 N3 C38 129.23(15) . . ?
N1 N3 C38 116.42(13) . . ?
C27 O7 C28 116.43(17) . . ?
C26 N2 N4 104.71(14) . . ?
C9 N1 N3 104.73(14) . . ?
C21 C20 C25 118.58(18) . . ?
C21 C20 C13 120.93(17) . . ?
C25 C20 C13 120.19(19) . . ?
O5 C13 N4 106.92(12) . . ?
O5 C13 C14 110.27(14) . . ?
N4 C13 C14 111.11(15) . . ?
O5 C13 C20 106.05(15) . . ?
N4 C13 C20 106.61(14) . . ?
C14 C13 C20 115.42(15) . . ?
N1 C9 C8 112.50(17) . . ?
N1 C9 C10 120.60(16) . . ?
C8 C9 C10 126.62(16) . . ?
O4 C38 N3 106.92(13) . . ?
O4 C38 C39 110.00(13) . . ?
N3 C38 C39 109.78(16) . . ?
O4 C38 C45 105.44(15) . . ?
N3 C38 C45 109.60(14) . . ?
C39 C38 C45 114.75(14) . . ?
C6 C1 C2 119.9(3) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C19 C14 C15 119.0(2) . . ?
C19 C14 C13 118.32(19) . . ?
C15 C14 C13 122.56(16) . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C44 C39 C40 119.23(17) . . ?
C44 C39 C38 119.50(19) . . ?
C40 C39 C38 121.05(16) . . ?
N3 C12 O5 121.41(16) . . ?
N3 C12 C8 107.77(15) . . ?
O5 C12 C8 130.81(15) . . ?
O2 C10 O3 124.50(19) . . ?
O2 C10 C9 123.02(19) . . ?
O3 C10 C9 112.46(16) . . ?
C12 C8 C9 104.14(15) . . ?
C12 C8 C7 131.71(16) . . ?
C9 C8 C7 123.71(17) . . ?
C34 C35 C36 119.9(3) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C41 C40 C39 120.89(19) . . ?
C41 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C46 C45 C50 117.92(19) . . ?
C46 C45 C38 122.15(17) . . ?
C50 C45 C38 119.93(19) . . ?
O4 C37 N4 121.70(14) . . ?
O4 C37 C29 129.82(16) . . ?
N4 C37 C29 108.48(16) . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 C7 117.6(2) . . ?
C5 C4 C7 122.81(19) . . ?
C23 C22 C21 119.7(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C39 C44 C43 119.3(2) . . ?
C39 C44 H44 120.3 . . ?
C43 C44 H44 120.3 . . ?
O8 C27 O7 124.13(19) . . ?
O8 C27 C26 123.4(2) . . ?
O7 C27 C26 112.42(18) . . ?
N2 C26 C29 112.53(16) . . ?
N2 C26 C27 119.32(17) . . ?
C29 C26 C27 128.05(17) . . ?
C42 C41 C40 119.7(2) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
C49 C50 C45 121.1(2) . . ?
C49 C50 H50 119.5 . . ?
C45 C50 H50 119.5 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O1 C7 C4 122.01(19) . . ?
O1 C7 C8 118.19(19) . . ?
C4 C7 C8 119.8(2) . . ?
C37 C29 C26 103.42(16) . . ?
C37 C29 C30 128.49(17) . . ?
C26 C29 C30 127.57(16) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C24 C25 C20 120.7(2) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
O6 C30 C31 121.19(18) . . ?
O6 C30 C29 118.2(2) . . ?
C31 C30 C29 120.61(17) . . ?
O7 C28 H28A 109.5 . . ?
O7 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O7 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C18 C19 C14 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C48 C49 C50 120.6(2) . . ?
C48 C49 H49 119.7 . . ?
C50 C49 H49 119.7 . . ?
C32 C31 C36 118.9(2) . . ?
C32 C31 C30 123.0(2) . . ?
C36 C31 C30 118.0(2) . . ?
C42 C43 C44 120.9(2) . . ?
C42 C43 H43 119.5 . . ?
C44 C43 H43 119.5 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C31 C32 C33 120.2(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C41 C42 C43 120.00(19) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C35 C34 C33 121.1(3) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C23 C24 C25 120.0(2) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C49 C48 C47 119.2(2) . . ?
C49 C48 H48 120.4 . . ?
C47 C48 H48 120.4 . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C45 C46 C47 120.7(2) . . ?
C45 C46 H46 119.6 . . ?
C47 C46 H46 119.6 . . ?
C35 C36 C31 120.8(3) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C48 C47 C46 120.5(3) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C34 C33 C32 119.1(3) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.857
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_md321
_database_code_depnum_ccdc_archive 'CCDC 1457142'
_audit_update_record             
;
2016-03-02 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H23 Br N2 O5'
_chemical_formula_sum            'C32 H23 Br N2 O5'
_chemical_formula_weight         595.43

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'
Br Br -0.2901 2.4595 '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 1 21/c 1'

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

_cell_length_a                   11.941(3)
_cell_length_b                   18.538(3)
_cell_length_c                   12.5422(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.318(17)
_cell_angle_gamma                90.00
_cell_volume                     2775.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5315
_cell_measurement_theta_min      3.0990
_cell_measurement_theta_max      25.4590

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65391
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22197
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         29.41
_reflns_number_total             6761
_reflns_number_gt                3861
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0977P)²+0.2927P] 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       0.0054(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6761
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.2028
_refine_ls_wR_factor_gt          0.1737
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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
Br1 Br -0.04600(5) 0.66684(2) -0.35928(3) 0.1050(3) Uani 1 1 d . . .
O2 O 0.14305(15) 0.62733(9) 0.14932(14) 0.0424(4) Uani 1 1 d . . .
O3 O 0.18791(17) 0.51414(10) 0.08410(16) 0.0535(5) Uani 1 1 d . . .
N2 N 0.22148(19) 0.54466(12) 0.26352(18) 0.0458(5) Uani 1 1 d . . .
N1 N 0.2834(2) 0.52346(13) 0.35059(19) 0.0520(6) Uani 1 1 d . . .
O5 O 0.5159(2) 0.41861(15) 0.3455(2) 0.0736(7) Uani 1 1 d . . .
C27 C 0.2203(2) 0.67123(13) 0.3136(2) 0.0453(7) Uani 1 1 d . . .
C21 C 0.0381(2) 0.59930(14) 0.3064(2) 0.0453(6) Uani 1 1 d . . .
C9 C 0.2396(2) 0.50231(14) 0.1781(2) 0.0467(7) Uani 1 1 d . . .
O1 O 0.3631(2) 0.32833(13) 0.2040(3) 0.0870(9) Uani 1 1 d . . .
C32 C 0.1905(3) 0.69980(17) 0.4107(3) 0.0577(8) Uani 1 1 d . . .
H32 H 0.1274 0.6825 0.4444 0.069 Uiso 1 1 calc R . .
C20 C 0.1538(2) 0.61080(14) 0.2618(2) 0.0429(6) Uani 1 1 d . . .
C14 C 0.0700(2) 0.59252(14) -0.0207(2) 0.0451(6) Uani 1 1 d . . .
C26 C -0.0394(3) 0.65391(18) 0.2907(3) 0.0631(9) Uani 1 1 d . . .
H26 H -0.0195 0.6954 0.2539 0.076 Uiso 1 1 calc R . .
C15 C 0.1346(3) 0.57828(19) -0.1066(3) 0.0642(9) Uani 1 1 d . . .
H15 H 0.2007 0.5522 -0.0974 0.077 Uiso 1 1 calc R . .
C13 C 0.1017(2) 0.56836(13) 0.0895(2) 0.0434(6) Uani 1 1 d . . .
H13 H 0.0360 0.5482 0.1241 0.052 Uiso 1 1 calc R . .
C11 C 0.4218(3) 0.43282(18) 0.3934(3) 0.0627(9) Uani 1 1 d . . .
C22 C 0.0078(3) 0.53883(18) 0.3606(2) 0.0573(8) Uani 1 1 d . . .
H22 H 0.0592 0.5018 0.3719 0.069 Uiso 1 1 calc R . .
C28 C 0.3161(3) 0.69680(18) 0.2660(3) 0.0607(8) Uani 1 1 d . . .
H28 H 0.3379 0.6779 0.2010 0.073 Uiso 1 1 calc R . .
C19 C -0.0285(3) 0.63087(17) -0.0354(3) 0.0573(8) Uani 1 1 d . . .
H19 H -0.0729 0.6407 0.0228 0.069 Uiso 1 1 calc R . .
C7 C 0.3483(3) 0.38284(18) 0.1527(3) 0.0616(8) Uani 1 1 d . . .
C10 C 0.3381(3) 0.46596(16) 0.3169(2) 0.0526(7) Uani 1 1 d . . .
C18 C -0.0613(3) 0.65468(18) -0.1352(3) 0.0656(9) Uani 1 1 d . . .
H18 H -0.1270 0.6812 -0.1446 0.079 Uiso 1 1 calc R . .
O4 O 0.4073(2) 0.4234(2) 0.4849(2) 0.1145(13) Uani 1 1 d . . .
C31 C 0.2540(3) 0.75390(19) 0.4579(3) 0.0712(10) Uani 1 1 d . . .
H31 H 0.2329 0.7733 0.5227 0.085 Uiso 1 1 calc R . .
C8 C 0.3156(2) 0.44927(15) 0.2086(3) 0.0514(7) Uani 1 1 d . . .
C23 C -0.1002(3) 0.5326(2) 0.3990(3) 0.0761(11) Uani 1 1 d . . .
H23 H -0.1203 0.4910 0.4355 0.091 Uiso 1 1 calc R . .
C4 C 0.3620(3) 0.3824(2) 0.0357(3) 0.0672(9) Uani 1 1 d . . .
C30 C 0.3473(3) 0.77881(19) 0.4098(3) 0.0744(10) Uani 1 1 d . . .
H30 H 0.3894 0.8154 0.4418 0.089 Uiso 1 1 calc R . .
C5 C 0.3590(4) 0.3162(3) -0.0177(5) 0.0993(16) Uani 1 1 d . . .
H5 H 0.3443 0.2739 0.0192 0.119 Uiso 1 1 calc R . .
C17 C 0.0037(3) 0.63889(17) -0.2206(2) 0.0636(9) Uani 1 1 d . . .
C29 C 0.3794(3) 0.7506(2) 0.3151(3) 0.0786(11) Uani 1 1 d . . .
H29 H 0.4439 0.7674 0.2833 0.094 Uiso 1 1 calc R . .
C16 C 0.1022(4) 0.6024(2) -0.2075(3) 0.0756(10) Uani 1 1 d . . .
H16 H 0.1473 0.5938 -0.2656 0.091 Uiso 1 1 calc R . .
C25 C -0.1464(3) 0.6472(2) 0.3295(4) 0.0829(12) Uani 1 1 d . . .
H25 H -0.1983 0.6840 0.3188 0.100 Uiso 1 1 calc R . .
C24 C -0.1757(3) 0.5855(3) 0.3842(3) 0.0828(12) Uani 1 1 d . . .
H24 H -0.2475 0.5807 0.4107 0.099 Uiso 1 1 calc R . .
C3 C 0.3855(3) 0.4439(2) -0.0216(3) 0.0775(11) Uani 1 1 d . . .
H3 H 0.3865 0.4882 0.0131 0.093 Uiso 1 1 calc R . .
C12 C 0.6037(4) 0.3860(3) 0.4120(4) 0.0998(15) Uani 1 1 d . . .
H12A H 0.6291 0.4201 0.4648 0.150 Uiso 1 1 calc R . .
H12B H 0.6652 0.3723 0.3684 0.150 Uiso 1 1 calc R . .
H12C H 0.5747 0.3440 0.4467 0.150 Uiso 1 1 calc R . .
C2 C 0.4076(4) 0.4414(3) -0.1299(4) 0.1039(15) Uani 1 1 d . . .
H2 H 0.4250 0.4831 -0.1673 0.125 Uiso 1 1 calc R . .
C1 C 0.4031(5) 0.3752(5) -0.1801(5) 0.132(3) Uani 1 1 d . . .
H1 H 0.4173 0.3720 -0.2525 0.158 Uiso 1 1 calc R . .
C6 C 0.3780(5) 0.3146(4) -0.1246(6) 0.127(2) Uani 1 1 d . . .
H6 H 0.3736 0.2708 -0.1605 0.153 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C17 1.897(3) . ?
O2 C13 1.409(3) . ?
O2 C20 1.446(3) . ?
O3 C9 1.336(3) . ?
O3 C13 1.441(3) . ?
N2 C9 1.350(4) . ?
N2 N1 1.363(3) . ?
N2 C20 1.468(3) . ?
N1 C10 1.324(4) . ?
O5 C11 1.312(4) . ?
O5 C12 1.457(4) . ?
C27 C32 1.382(4) . ?
C27 C28 1.386(4) . ?
C27 C20 1.511(4) . ?
C21 C22 1.364(4) . ?
C21 C26 1.383(4) . ?
C21 C20 1.518(4) . ?
C9 C8 1.386(4) . ?
O1 C7 1.209(4) . ?
C32 C31 1.382(5) . ?
C32 H32 0.9300 . ?
C14 C15 1.365(4) . ?
C14 C19 1.383(4) . ?
C14 C13 1.494(4) . ?
C26 C25 1.382(5) . ?
C26 H26 0.9300 . ?
C15 C16 1.389(5) . ?
C15 H15 0.9300 . ?
C13 H13 0.9800 . ?
C11 O4 1.178(4) . ?
C11 C10 1.501(4) . ?
C22 C23 1.391(5) . ?
C22 H22 0.9300 . ?
C28 C29 1.387(5) . ?
C28 H28 0.9300 . ?
C19 C18 1.377(4) . ?
C19 H19 0.9300 . ?
C7 C8 1.474(4) . ?
C7 C4 1.480(5) . ?
C10 C8 1.413(4) . ?
C18 C17 1.369(5) . ?
C18 H18 0.9300 . ?
C31 C30 1.359(5) . ?
C31 H31 0.9300 . ?
C23 C24 1.343(6) . ?
C23 H23 0.9300 . ?
C4 C3 1.380(6) . ?
C4 C5 1.398(5) . ?
C30 C29 1.361(5) . ?
C30 H30 0.9300 . ?
C5 C6 1.366(9) . ?
C5 H5 0.9300 . ?
C17 C16 1.364(5) . ?
C29 H29 0.9300 . ?
C16 H16 0.9300 . ?
C25 C24 1.384(6) . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?
C3 C2 1.390(6) . ?
C3 H3 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 C1 1.381(9) . ?
C2 H2 0.9300 . ?
C1 C6 1.358(9) . ?
C1 H1 0.9300 . ?
C6 H6 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
C13 O2 C20 112.16(19) . . ?
C9 O3 C13 112.9(2) . . ?
C9 N2 N1 112.0(2) . . ?
C9 N2 C20 124.9(2) . . ?
N1 N2 C20 122.8(2) . . ?
C10 N1 N2 103.8(2) . . ?
C11 O5 C12 115.7(3) . . ?
C32 C27 C28 118.7(3) . . ?
C32 C27 C20 121.3(3) . . ?
C28 C27 C20 119.9(3) . . ?
C22 C21 C26 119.2(3) . . ?
C22 C21 C20 123.6(3) . . ?
C26 C21 C20 117.2(3) . . ?
O3 C9 N2 121.7(2) . . ?
O3 C9 C8 130.3(3) . . ?
N2 C9 C8 108.0(2) . . ?
C27 C32 C31 120.4(3) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
O2 C20 N2 103.2(2) . . ?
O2 C20 C27 107.3(2) . . ?
N2 C20 C27 109.2(2) . . ?
O2 C20 C21 109.1(2) . . ?
N2 C20 C21 112.5(2) . . ?
C27 C20 C21 114.8(2) . . ?
C15 C14 C19 119.3(3) . . ?
C15 C14 C13 122.4(3) . . ?
C19 C14 C13 118.3(3) . . ?
C25 C26 C21 120.3(3) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
O2 C13 O3 108.9(2) . . ?
O2 C13 C14 109.8(2) . . ?
O3 C13 C14 109.4(2) . . ?
O2 C13 H13 109.6 . . ?
O3 C13 H13 109.6 . . ?
C14 C13 H13 109.6 . . ?
O4 C11 O5 124.2(3) . . ?
O4 C11 C10 124.9(3) . . ?
O5 C11 C10 110.8(3) . . ?
C21 C22 C23 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C27 C28 C29 120.1(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C18 C19 C14 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
O1 C7 C8 118.8(3) . . ?
O1 C7 C4 120.3(3) . . ?
C8 C7 C4 120.8(3) . . ?
N1 C10 C8 113.5(2) . . ?
N1 C10 C11 116.9(3) . . ?
C8 C10 C11 129.3(3) . . ?
C17 C18 C19 119.2(3) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C9 C8 C10 102.7(2) . . ?
C9 C8 C7 129.8(3) . . ?
C10 C8 C7 126.4(3) . . ?
C24 C23 C22 121.1(4) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 C7 122.7(3) . . ?
C5 C4 C7 118.5(4) . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C6 C5 C4 119.1(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 Br1 119.8(3) . . ?
C18 C17 Br1 119.2(3) . . ?
C30 C29 C28 120.1(4) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C23 C24 C25 119.7(4) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C4 C3 C2 121.8(4) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C2 C3 118.0(6) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C6 C1 C2 120.6(6) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C6 C5 121.9(6) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?

_diffrn_measured_fraction_theta_max 0.882
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.726
_refine_diff_density_min         -1.186
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_psu-119-vzh-89
_database_code_depnum_ccdc_archive 'CCDC 1457143'
_audit_update_record             
;
2016-03-02 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 Br N3 O4'
_chemical_formula_sum            'C32 H22 Br N3 O4'
_chemical_formula_weight         592.44

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   11.0358(18)
_cell_length_b                   11.317(2)
_cell_length_c                   22.376(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.18(2)
_cell_angle_gamma                90.00
_cell_volume                     2787.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3554
_cell_measurement_theta_min      3.5740
_cell_measurement_theta_max      23.5180

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    1.517
_exptl_absorpt_correction_T_min  0.76822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(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  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14952
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         29.22
_reflns_number_total             6566
_reflns_number_gt                3465
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0622P)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         6566
_refine_ls_number_parameters     436
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

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
C32 C 0.1300(7) 0.1303(6) 0.4814(4) 0.142(4) Uani 0.600(6) 1 d P A 1
H32A H 0.1711 0.0965 0.4492 0.212 Uiso 0.600(6) 1 calc PR A 1
H32B H 0.0609 0.0824 0.4891 0.212 Uiso 0.600(6) 1 calc PR A 1
H32C H 0.1845 0.1335 0.5168 0.212 Uiso 0.600(6) 1 calc PR A 1
C32A C 0.3142(12) 0.1790(12) 0.4601(7) 0.178(7) Uani 0.400(6) 1 d P A 2
H32D H 0.3173 0.1798 0.5031 0.266 Uiso 0.400(6) 1 calc PR A 2
H32E H 0.3941 0.1649 0.4473 0.266 Uiso 0.400(6) 1 calc PR A 2
H32F H 0.2603 0.1174 0.4451 0.266 Uiso 0.400(6) 1 calc PR A 2
C13 C 0.3709(13) 0.8490(7) 0.5286(6) 0.105(4) Uani 0.600(6) 1 d PD A 1
H13 H 0.4168 0.8769 0.5622 0.126 Uiso 0.600(6) 1 calc PR A 1
C14 C 0.4223(7) 0.8108(7) 0.4817(4) 0.120(3) Uani 0.600(6) 1 d PD A 1
H14 H 0.5067 0.8117 0.4826 0.144 Uiso 0.600(6) 1 calc PR A 1
C15 C 0.3592(5) 0.7697(6) 0.4317(3) 0.085(2) Uani 0.600(6) 1 d PD A 1
H15 H 0.4007 0.7371 0.4009 0.102 Uiso 0.600(6) 1 calc PR A 1
C13A C 0.3524(12) 0.9111(11) 0.5166(6) 0.076(4) Uani 0.400(6) 1 d P A 2
H13A H 0.3985 0.9458 0.5484 0.091 Uiso 0.400(6) 1 calc PR A 2
C14A C 0.3840(11) 0.9244(13) 0.4601(6) 0.121(5) Uani 0.400(6) 1 d P A 2
H14A H 0.4471 0.9756 0.4528 0.145 Uiso 0.400(6) 1 calc PR A 2
C15A C 0.3248(9) 0.8632(11) 0.4115(4) 0.096(4) Uani 0.400(6) 1 d P A 2
H15A H 0.3426 0.8776 0.3721 0.116 Uiso 0.400(6) 1 calc PR A 2
C17 C 0.2787(9) 0.6126(9) 0.2962(4) 0.084(3) Uani 0.600(6) 1 d PD A 1
H17 H 0.2692 0.5438 0.3181 0.101 Uiso 0.600(6) 1 calc PR A 1
C18 C 0.3417(12) 0.6044(12) 0.2472(7) 0.111(5) Uani 0.600(6) 1 d PD A 1
H18 H 0.3757 0.5327 0.2369 0.134 Uiso 0.600(6) 1 calc PR A 1
C20 C 0.3060(9) 0.8101(9) 0.2322(4) 0.104(3) Uani 0.600(6) 1 d PD A 1
H20 H 0.3173 0.8785 0.2103 0.125 Uiso 0.600(6) 1 calc PR A 1
C8 C 0.2419(8) 0.8126(7) 0.2831(4) 0.090(3) Uani 0.600(6) 1 d PD A 1
H8 H 0.2077 0.8833 0.2948 0.108 Uiso 0.600(6) 1 calc PR A 1
C17A C 0.3256(11) 0.6366(13) 0.3178(7) 0.070(4) Uani 0.400(6) 1 d PD A 2
H17A H 0.3504 0.5930 0.3517 0.084 Uiso 0.400(6) 1 calc PR A 2
C18A C 0.3867(16) 0.6292(17) 0.2633(9) 0.088(6) Uani 0.400(6) 1 d PD A 2
H18A H 0.4502 0.5756 0.2613 0.105 Uiso 0.400(6) 1 calc PR A 2
C20A C 0.2590(10) 0.7567(13) 0.2143(5) 0.087(4) Uani 0.400(6) 1 d PD A 2
H20A H 0.2295 0.7928 0.1788 0.104 Uiso 0.400(6) 1 calc PR A 2
C8A C 0.1945(8) 0.7704(10) 0.2644(5) 0.064(3) Uani 0.400(6) 1 d PD A 2
H8A H 0.1271 0.8200 0.2627 0.077 Uiso 0.400(6) 1 calc PR A 2
C12 C 0.2525(5) 0.8466(3) 0.52660(17) 0.0967(13) Uani 1 1 d D . .
H12 H 0.2118 0.8779 0.5580 0.116 Uiso 1 1 calc R A 1
C11 C 0.1881(4) 0.7974(3) 0.47788(18) 0.0925(12) Uani 1 1 d D A .
H11 H 0.1071 0.7780 0.4817 0.111 Uiso 1 1 calc R . .
C19 C 0.3549(3) 0.6981(4) 0.21412(18) 0.0893(12) Uani 1 1 d D . .
H19 H 0.3954 0.6928 0.1792 0.107 Uiso 1 1 calc R A 1
C10 C 0.2338(2) 0.7759(2) 0.42599(14) 0.0545(7) Uani 1 1 d D . .
C16 C 0.2280(2) 0.7123(2) 0.31645(12) 0.0469(7) Uani 1 1 d D . .
Br1 Br -0.49691(3) 1.07148(3) 0.289635(19) 0.0887(2) Uani 1 1 d . . .
C21 C -0.0003(2) 0.5667(2) 0.37868(12) 0.0444(6) Uani 1 1 d . A .
O1 O -0.08782(14) 0.63940(15) 0.35603(9) 0.0572(5) Uani 1 1 d . . .
N1 N 0.05186(18) 0.79682(18) 0.35945(10) 0.0525(6) Uani 1 1 d . . .
N2 N 0.11418(17) 0.60419(18) 0.39035(10) 0.0458(5) Uani 1 1 d . . .
C24 C -0.2364(2) 0.4123(2) 0.38506(13) 0.0476(7) Uani 1 1 d . . .
N3 N 0.18705(18) 0.51621(19) 0.41302(10) 0.0476(5) Uani 1 1 d . A .
C22 C -0.0073(2) 0.4493(2) 0.39310(12) 0.0458(6) Uani 1 1 d . . .
C9 C 0.1583(2) 0.7230(2) 0.37320(12) 0.0473(7) Uani 1 1 d D A .
C4 C -0.1610(2) 0.8317(2) 0.33536(13) 0.0500(7) Uani 1 1 d . . .
O2 O -0.09327(18) 0.27103(18) 0.35871(12) 0.0811(7) Uani 1 1 d . . .
C7 C -0.0542(2) 0.7578(2) 0.35131(13) 0.0506(7) Uani 1 1 d . A .
C31 C 0.1638(3) 0.3124(3) 0.44091(14) 0.0624(8) Uani 1 1 d . . .
C30 C 0.1140(2) 0.4233(2) 0.41463(12) 0.0458(6) Uani 1 1 d . A .
O4 O 0.2712(2) 0.2889(2) 0.43783(12) 0.0904(8) Uani 1 1 d . A .
C1 C -0.3597(2) 0.9738(3) 0.30712(14) 0.0608(8) Uani 1 1 d . A .
C3 C -0.1471(3) 0.9516(2) 0.32863(14) 0.0607(8) Uani 1 1 d . A .
H3 H -0.0700 0.9847 0.3338 0.073 Uiso 1 1 calc R . .
C23 C -0.1118(2) 0.3700(2) 0.37775(13) 0.0521(7) Uani 1 1 d . A .
C25 C -0.2602(2) 0.4887(3) 0.43067(14) 0.0628(8) Uani 1 1 d . . .
H25 H -0.1961 0.5209 0.4546 0.075 Uiso 1 1 calc R . .
C28 C -0.4501(3) 0.3977(4) 0.3600(2) 0.0928(12) Uani 1 1 d . . .
H28 H -0.5147 0.3678 0.3356 0.111 Uiso 1 1 calc R . .
C6 C -0.3757(3) 0.8554(3) 0.31209(17) 0.0799(10) Uani 1 1 d . . .
H6 H -0.4529 0.8228 0.3055 0.096 Uiso 1 1 calc R A .
C5 C -0.2768(3) 0.7833(3) 0.32695(16) 0.0742(10) Uani 1 1 d . A .
H5 H -0.2878 0.7024 0.3313 0.089 Uiso 1 1 calc R . .
C26 C -0.3786(3) 0.5182(3) 0.44139(16) 0.0815(10) Uani 1 1 d . . .
H26 H -0.3939 0.5698 0.4723 0.098 Uiso 1 1 calc R . .
C29 C -0.3320(3) 0.3674(3) 0.34904(16) 0.0709(9) Uani 1 1 d . . .
H29 H -0.3175 0.3171 0.3175 0.085 Uiso 1 1 calc R . .
C2 C -0.2459(3) 1.0233(3) 0.31438(15) 0.0674(9) Uani 1 1 d . . .
H2 H -0.2356 1.1042 0.3097 0.081 Uiso 1 1 calc R A .
O3 O 0.0901(2) 0.2475(2) 0.46541(15) 0.1239(12) Uani 1 1 d . A .
C27 C -0.4721(3) 0.4711(4) 0.4064(2) 0.0932(12) Uani 1 1 d . . .
H27 H -0.5518 0.4889 0.4141 0.112 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C32 O3 1.436(7) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C32A O4 1.410(11) . ?
C32A H32D 0.9600 . ?
C32A H32E 0.9600 . ?
C32A H32F 0.9600 . ?
C13 C14 1.302(14) . ?
C13 C12 1.305(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(9) . ?
C14 H14 0.9300 . ?
C15 C10 1.382(6) . ?
C15 H15 0.9300 . ?
C13A C14A 1.345(17) . ?
C13A C12 1.355(16) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.410(14) . ?
C14A H14A 0.9300 . ?
C15A C10 1.462(9) . ?
C15A H15A 0.9300 . ?
C17 C18 1.345(18) . ?
C17 C16 1.352(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.307(11) . ?
C18 H18 0.9300 . ?
C20 C8 1.383(10) . ?
C20 C19 1.447(11) . ?
C20 H20 0.9300 . ?
C8 C16 1.374(8) . ?
C8 H8 0.9300 . ?
C17A C16 1.375(12) . ?
C17A C18A 1.44(3) . ?
C17A H17A 0.9300 . ?
C18A C19 1.374(16) . ?
C18A H18A 0.9300 . ?
C20A C19 1.249(12) . ?
C20A C8A 1.380(12) . ?
C20A H20A 0.9300 . ?
C8A C16 1.365(11) . ?
C8A H8A 0.9300 . ?
C12 C11 1.375(5) . ?
C12 H12 0.9300 . ?
C11 C10 1.322(4) . ?
C11 H11 0.9300 . ?
C19 H19 0.9300 . ?
C10 C9 1.518(4) . ?
C16 C9 1.536(4) . ?
Br1 C1 1.892(3) . ?
C21 N2 1.340(3) . ?
C21 O1 1.340(3) . ?
C21 C22 1.371(3) . ?
O1 C7 1.397(3) . ?
N1 C7 1.252(3) . ?
N1 C9 1.456(3) . ?
N2 N3 1.355(3) . ?
N2 C9 1.490(3) . ?
C24 C29 1.377(4) . ?
C24 C25 1.378(4) . ?
C24 C23 1.477(4) . ?
N3 C30 1.327(3) . ?
C22 C30 1.421(3) . ?
C22 C23 1.481(4) . ?
C4 C3 1.375(4) . ?
C4 C5 1.390(4) . ?
C4 C7 1.468(4) . ?
O2 C23 1.221(3) . ?
C31 O4 1.222(3) . ?
C31 O3 1.252(4) . ?
C31 C30 1.474(4) . ?
C1 C6 1.357(4) . ?
C1 C2 1.374(4) . ?
C3 C2 1.377(4) . ?
C3 H3 0.9300 . ?
C25 C26 1.387(4) . ?
C25 H25 0.9300 . ?
C28 C27 1.365(5) . ?
C28 C29 1.386(4) . ?
C28 H28 0.9300 . ?
C6 C5 1.384(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C26 C27 1.358(5) . ?
C26 H26 0.9300 . ?
C29 H29 0.9300 . ?
C2 H2 0.9300 . ?
C27 H27 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
O3 C32 H32A 109.5 . . ?
O3 C32 H32B 109.5 . . ?
O3 C32 H32C 109.5 . . ?
O4 C32A H32D 109.5 . . ?
O4 C32A H32E 109.5 . . ?
H32D C32A H32E 109.5 . . ?
O4 C32A H32F 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 109.5 . . ?
C14 C13 C12 117.4(9) . . ?
C14 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
C13 C14 C15 123.4(8) . . ?
C13 C14 H14 118.3 . . ?
C15 C14 H14 118.3 . . ?
C14 C15 C10 120.6(6) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C14A C13A C12 119.0(10) . . ?
C14A C13A H13A 120.5 . . ?
C12 C13A H13A 120.5 . . ?
C13A C14A C15A 122.3(9) . . ?
C13A C14A H14A 118.9 . . ?
C15A C14A H14A 118.9 . . ?
C14A C15A C10 116.6(8) . . ?
C14A C15A H15A 121.7 . . ?
C10 C15A H15A 121.7 . . ?
C18 C17 C16 125.6(10) . . ?
C18 C17 H17 117.2 . . ?
C16 C17 H17 117.2 . . ?
C19 C18 C17 119.4(13) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C8 C20 C19 118.2(7) . . ?
C8 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C16 C8 C20 121.0(8) . . ?
C16 C8 H8 119.5 . . ?
C20 C8 H8 119.5 . . ?
C16 C17A C18A 115.7(13) . . ?
C16 C17A H17A 122.1 . . ?
C18A C17A H17A 122.1 . . ?
C19 C18A C17A 122.5(17) . . ?
C19 C18A H18A 118.8 . . ?
C17A C18A H18A 118.8 . . ?
C19 C20A C8A 123.3(10) . . ?
C19 C20A H20A 118.3 . . ?
C8A C20A H20A 118.3 . . ?
C16 C8A C20A 121.0(9) . . ?
C16 C8A H8A 119.5 . . ?
C20A C8A H8A 119.5 . . ?
C13 C12 C11 119.6(7) . . ?
C13A C12 C11 117.9(6) . . ?
C13 C12 H12 120.2 . . ?
C13A C12 H12 111.2 . . ?
C11 C12 H12 120.2 . . ?
C10 C11 C12 124.2(4) . . ?
C10 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
C20A C19 C18 107.4(9) . . ?
C20A C19 C18A 117.8(11) . . ?
C18 C19 C20 119.5(9) . . ?
C18A C19 C20 110.6(11) . . ?
C20A C19 H19 119.7 . . ?
C18 C19 H19 120.2 . . ?
C18A C19 H19 121.7 . . ?
C20 C19 H19 120.2 . . ?
C11 C10 C15 111.8(4) . . ?
C11 C10 C15A 112.5(5) . . ?
C11 C10 C9 122.2(3) . . ?
C15 C10 C9 122.7(3) . . ?
C15A C10 C9 116.1(4) . . ?
C17 C16 C8A 102.1(7) . . ?
C17 C16 C8 116.3(7) . . ?
C8A C16 C17A 118.8(8) . . ?
C8 C16 C17A 114.1(8) . . ?
C17 C16 C9 125.9(5) . . ?
C8A C16 C9 123.2(5) . . ?
C8 C16 C9 117.9(4) . . ?
C17A C16 C9 118.0(7) . . ?
N2 C21 O1 121.6(2) . . ?
N2 C21 C22 109.2(2) . . ?
O1 C21 C22 129.2(2) . . ?
C21 O1 C7 115.42(18) . . ?
C7 N1 C9 124.0(2) . . ?
C21 N2 N3 111.47(19) . . ?
C21 N2 C9 123.8(2) . . ?
N3 N2 C9 124.28(18) . . ?
C29 C24 C25 119.1(3) . . ?
C29 C24 C23 119.7(3) . . ?
C25 C24 C23 121.0(2) . . ?
C30 N3 N2 104.34(19) . . ?
C21 C22 C30 102.3(2) . . ?
C21 C22 C23 126.1(2) . . ?
C30 C22 C23 130.7(2) . . ?
N1 C9 N2 107.36(18) . . ?
N1 C9 C10 109.1(2) . . ?
N2 C9 C10 109.1(2) . . ?
N1 C9 C16 108.3(2) . . ?
N2 C9 C16 109.6(2) . . ?
C10 C9 C16 113.3(2) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 C7 119.6(2) . . ?
C5 C4 C7 121.5(2) . . ?
N1 C7 O1 125.3(2) . . ?
N1 C7 C4 124.1(2) . . ?
O1 C7 C4 110.6(2) . . ?
O4 C31 O3 124.1(3) . . ?
O4 C31 C30 119.8(3) . . ?
O3 C31 C30 116.0(3) . . ?
N3 C30 C22 112.7(2) . . ?
N3 C30 C31 118.4(2) . . ?
C22 C30 C31 128.8(2) . . ?
C31 O4 C32A 118.3(6) . . ?
C6 C1 C2 121.1(3) . . ?
C6 C1 Br1 119.1(2) . . ?
C2 C1 Br1 119.8(2) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
O2 C23 C24 121.1(2) . . ?
O2 C23 C22 119.3(2) . . ?
C24 C23 C22 119.6(2) . . ?
C24 C25 C26 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27 C28 C29 120.5(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C27 C26 C25 119.5(3) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C24 C29 C28 119.7(3) . . ?
C24 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C31 O3 C32 117.1(4) . . ?
C26 C27 C28 120.5(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.867
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.047
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_psu-142-vzh-114
_database_code_depnum_ccdc_archive 'CCDC 1457144'
_audit_update_record             
;
2016-03-02 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H34 N2 O5'
_chemical_formula_sum            'C29 H34 N2 O5'
_chemical_formula_weight         490.58

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'


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

_cell_length_a                   11.6231(17)
_cell_length_b                   10.6422(16)
_cell_length_c                   21.254(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.894(13)
_cell_angle_gamma                90.00
_cell_volume                     2610.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4196
_cell_measurement_theta_min      3.6160
_cell_measurement_theta_max      28.9530


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84059
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(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  'New Xcalibur, Ruby'
_diffrn_measurement_method       'w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13368
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         29.40
_reflns_number_total             6116
_reflns_number_gt                4637
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0800P)²+0.5127P] 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         6116
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O1 O 0.01871(10) 0.56622(11) 0.13666(5) 0.0437(3) Uani 1 1 d . . .
N1 N 0.04257(11) 0.27573(12) 0.21579(6) 0.0362(3) Uani 1 1 d . . .
O4 O -0.07927(11) 0.74719(11) 0.15090(6) 0.0462(3) Uani 1 1 d . . .
N2 N -0.00191(10) 0.39323(12) 0.20296(6) 0.0331(3) Uani 1 1 d . . .
O3 O 0.14043(11) 0.04651(11) 0.17617(7) 0.0536(3) Uani 1 1 d . . .
C4 C -0.08442(14) 0.62090(15) 0.15992(7) 0.0372(4) Uani 1 1 d . . .
H4 H -0.1551 0.5863 0.1365 0.045 Uiso 1 1 calc R . .
C1 C 0.12440(13) 0.26473(15) 0.17825(7) 0.0346(3) Uani 1 1 d . . .
C13 C -0.06917(12) 0.40539(16) 0.30777(7) 0.0350(3) Uani 1 1 d . . .
C6 C -0.09222(12) 0.44790(15) 0.23843(7) 0.0319(3) Uani 1 1 d . . .
C7 C -0.21370(13) 0.40560(16) 0.20956(7) 0.0371(4) Uani 1 1 d . . .
C3 C 0.05046(13) 0.45196(15) 0.15811(7) 0.0333(3) Uani 1 1 d . . .
C5 C -0.07969(14) 0.59031(15) 0.22936(7) 0.0364(3) Uani 1 1 d . . .
H5A H -0.1417 0.6338 0.2471 0.044 Uiso 1 1 calc R . .
H5B H -0.0065 0.6186 0.2516 0.044 Uiso 1 1 calc R . .
C21 C 0.22049(14) 0.38160(17) 0.09353(8) 0.0409(4) Uani 1 1 d . . .
O5 O 0.26510(15) 0.28425(14) 0.07870(8) 0.0748(5) Uani 1 1 d . . .
C2 C 0.13580(13) 0.37234(15) 0.14017(7) 0.0344(3) Uani 1 1 d . . .
C22 C 0.25406(13) 0.50741(17) 0.06630(7) 0.0402(4) Uani 1 1 d . . .
O2 O 0.30150(12) 0.15539(14) 0.20514(9) 0.0779(5) Uani 1 1 d . . .
C19 C 0.20020(14) 0.15150(16) 0.18699(8) 0.0403(4) Uani 1 1 d . . .
C18 C -0.10376(15) 0.28607(18) 0.32443(8) 0.0449(4) Uani 1 1 d . . .
H18 H -0.1407 0.2335 0.2934 0.054 Uiso 1 1 calc R . .
C26 C -0.10683(19) 0.78422(19) 0.08558(9) 0.0546(5) Uani 1 1 d . . .
H26A H -0.1744 0.7385 0.0666 0.065 Uiso 1 1 calc R . .
H26B H -0.0425 0.7645 0.0621 0.065 Uiso 1 1 calc R . .
C14 C -0.01287(16) 0.48146(19) 0.35453(8) 0.0490(4) Uani 1 1 d . . .
H14 H 0.0125 0.5610 0.3443 0.059 Uiso 1 1 calc R . .
C12 C -0.30831(15) 0.45226(19) 0.23647(10) 0.0512(5) Uani 1 1 d . . .
H12 H -0.2962 0.5058 0.2712 0.061 Uiso 1 1 calc R . .
C24 C 0.35951(17) 0.4874(2) 0.03058(10) 0.0583(5) Uani 1 1 d . . .
H24A H 0.3413 0.4257 -0.0021 0.087 Uiso 1 1 calc R . .
H24B H 0.4238 0.4587 0.0596 0.087 Uiso 1 1 calc R . .
H24C H 0.3795 0.5653 0.0118 0.087 Uiso 1 1 calc R . .
C23 C 0.28522(16) 0.60314(19) 0.11964(9) 0.0514(5) Uani 1 1 d . . .
H23A H 0.3460 0.5698 0.1495 0.077 Uiso 1 1 calc R . .
H23B H 0.2182 0.6197 0.1407 0.077 Uiso 1 1 calc R . .
H23C H 0.3109 0.6798 0.1020 0.077 Uiso 1 1 calc R . .
C17 C -0.08425(18) 0.2444(2) 0.38614(9) 0.0558(5) Uani 1 1 d . . .
H17 H -0.1075 0.1642 0.3964 0.067 Uiso 1 1 calc R . .
C8 C -0.23347(16) 0.3268(2) 0.15832(9) 0.0519(5) Uani 1 1 d . . .
H8 H -0.1714 0.2946 0.1396 0.062 Uiso 1 1 calc R . .
C25 C 0.15330(17) 0.5531(2) 0.01877(9) 0.0582(5) Uani 1 1 d . . .
H25A H 0.1747 0.6302 -0.0003 0.087 Uiso 1 1 calc R . .
H25B H 0.0864 0.5672 0.0403 0.087 Uiso 1 1 calc R . .
H25C H 0.1356 0.4907 -0.0136 0.087 Uiso 1 1 calc R . .
C27 C -0.1304(2) 0.9221(2) 0.08255(11) 0.0624(5) Uani 1 1 d . . .
H27A H -0.0620 0.9673 0.1009 0.075 Uiso 1 1 calc R . .
H27B H -0.1931 0.9415 0.1073 0.075 Uiso 1 1 calc R . .
C16 C -0.03024(19) 0.3219(2) 0.43261(9) 0.0622(6) Uani 1 1 d . . .
H16 H -0.0184 0.2947 0.4745 0.075 Uiso 1 1 calc R . .
C10 C -0.43908(18) 0.3411(3) 0.16105(13) 0.0742(8) Uani 1 1 d . . .
H10 H -0.5143 0.3195 0.1448 0.089 Uiso 1 1 calc R . .
C11 C -0.41985(17) 0.4201(2) 0.21226(13) 0.0701(7) Uani 1 1 d . . .
H11 H -0.4823 0.4521 0.2307 0.084 Uiso 1 1 calc R . .
C15 C 0.0058(2) 0.4387(2) 0.41690(9) 0.0629(6) Uani 1 1 d . . .
H15 H 0.0432 0.4904 0.4482 0.075 Uiso 1 1 calc R . .
C9 C -0.3474(2) 0.2947(2) 0.13422(11) 0.0698(6) Uani 1 1 d . . .
H9 H -0.3603 0.2411 0.0995 0.084 Uiso 1 1 calc R . .
C20 C 0.2039(2) -0.06985(19) 0.18924(13) 0.0708(6) Uani 1 1 d . . .
H20A H 0.2658 -0.0745 0.1632 0.106 Uiso 1 1 calc R . .
H20B H 0.1525 -0.1398 0.1800 0.106 Uiso 1 1 calc R . .
H20C H 0.2353 -0.0722 0.2331 0.106 Uiso 1 1 calc R . .
C28 C -0.1633(3) 0.9654(2) 0.01440(12) 0.0790(7) Uani 1 1 d . . .
H28A H -0.1024 0.9414 -0.0107 0.095 Uiso 1 1 calc R . .
H28B H -0.2339 0.9231 -0.0031 0.095 Uiso 1 1 calc R . .
C29 C -0.1810(3) 1.1033(3) 0.00960(16) 0.1110(11) Uani 1 1 d . . .
H29A H -0.2490 1.1258 0.0286 0.166 Uiso 1 1 calc R . .
H29B H -0.1908 1.1276 -0.0342 0.166 Uiso 1 1 calc R . .
H29C H -0.1148 1.1455 0.0313 0.166 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O1 C3 1.3350(19) . ?
O1 C4 1.4704(18) . ?
N1 C1 1.3180(19) . ?
N1 N2 1.3680(18) . ?
O4 C4 1.360(2) . ?
O4 C26 1.442(2) . ?
N2 C3 1.3451(19) . ?
N2 C6 1.4828(18) . ?
O3 C19 1.321(2) . ?
O3 C20 1.451(2) . ?
C4 C5 1.506(2) . ?
C4 H4 0.9800 . ?
C1 C2 1.418(2) . ?
C1 C19 1.491(2) . ?
C13 C14 1.384(2) . ?
C13 C18 1.391(2) . ?
C13 C6 1.534(2) . ?
C6 C5 1.537(2) . ?
C6 C7 1.538(2) . ?
C7 C8 1.372(3) . ?
C7 C12 1.391(2) . ?
C3 C2 1.392(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C21 O5 1.217(2) . ?
C21 C2 1.482(2) . ?
C21 C22 1.528(2) . ?
C22 C25 1.531(3) . ?
C22 C24 1.532(2) . ?
C22 C23 1.535(3) . ?
O2 C19 1.195(2) . ?
C18 C17 1.377(2) . ?
C18 H18 0.9300 . ?
C26 C27 1.493(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C14 C15 1.394(3) . ?
C14 H14 0.9300 . ?
C12 C11 1.379(3) . ?
C12 H12 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C17 C16 1.378(3) . ?
C17 H17 0.9300 . ?
C8 C9 1.403(3) . ?
C8 H8 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C27 C28 1.524(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C16 C15 1.366(3) . ?
C16 H16 0.9300 . ?
C10 C9 1.361(4) . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C28 C29 1.484(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C3 O1 C4 116.66(11) . . ?
C1 N1 N2 104.09(12) . . ?
C4 O4 C26 113.42(14) . . ?
C3 N2 N1 111.94(12) . . ?
C3 N2 C6 125.89(13) . . ?
N1 N2 C6 122.07(12) . . ?
C19 O3 C20 116.34(15) . . ?
O4 C4 O1 106.99(12) . . ?
O4 C4 C5 110.79(14) . . ?
O1 C4 C5 107.98(12) . . ?
O4 C4 H4 110.3 . . ?
O1 C4 H4 110.3 . . ?
C5 C4 H4 110.3 . . ?
N1 C1 C2 113.43(13) . . ?
N1 C1 C19 117.06(14) . . ?
C2 C1 C19 129.02(13) . . ?
C14 C13 C18 118.53(16) . . ?
C14 C13 C6 122.03(15) . . ?
C18 C13 C6 119.43(15) . . ?
N2 C6 C13 108.67(12) . . ?
N2 C6 C5 103.86(11) . . ?
C13 C6 C5 113.77(13) . . ?
N2 C6 C7 110.75(12) . . ?
C13 C6 C7 110.07(12) . . ?
C5 C6 C7 109.56(13) . . ?
C8 C7 C12 118.65(16) . . ?
C8 C7 C6 123.64(14) . . ?
C12 C7 C6 117.70(16) . . ?
O1 C3 N2 122.35(13) . . ?
O1 C3 C2 129.62(13) . . ?
N2 C3 C2 108.01(14) . . ?
C4 C5 C6 110.08(13) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
O5 C21 C2 117.04(16) . . ?
O5 C21 C22 120.78(14) . . ?
C2 C21 C22 122.15(14) . . ?
C3 C2 C1 102.52(13) . . ?
C3 C2 C21 134.04(15) . . ?
C1 C2 C21 123.42(14) . . ?
C21 C22 C25 108.57(15) . . ?
C21 C22 C24 108.77(15) . . ?
C25 C22 C24 108.14(14) . . ?
C21 C22 C23 110.50(14) . . ?
C25 C22 C23 111.74(16) . . ?
C24 C22 C23 109.05(15) . . ?
O2 C19 O3 124.24(16) . . ?
O2 C19 C1 123.83(16) . . ?
O3 C19 C1 111.79(14) . . ?
C17 C18 C13 121.11(18) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
O4 C26 C27 109.18(17) . . ?
O4 C26 H26A 109.8 . . ?
C27 C26 H26A 109.8 . . ?
O4 C26 H26B 109.8 . . ?
C27 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
C13 C14 C15 119.89(19) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 C27 C28 111.20(19) . . ?
C26 C27 H27A 109.4 . . ?
C28 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
C28 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C15 C16 C17 119.71(18) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C29 C28 C27 112.4(2) . . ?
C29 C28 H28A 109.1 . . ?
C27 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.849
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_psu-308-vzh-129
_database_code_depnum_ccdc_archive 'CCDC 1457145'
_audit_update_record             
;
2016-03-02 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H32 Cl N3 O4'
_chemical_formula_sum            'C36 H32 Cl N3 O4'
_chemical_formula_weight         606.10

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   7.2763(12)
_cell_length_b                   10.4418(18)
_cell_length_c                   21.710(2)
_cell_angle_alpha                91.501(11)
_cell_angle_beta                 93.402(12)
_cell_angle_gamma                108.619(16)
_cell_volume                     1558.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2165
_cell_measurement_theta_min      3.4200
_cell_measurement_theta_max      26.1590


_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_min  0.75109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(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  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13259
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         29.41
_reflns_number_total             7224
_reflns_number_gt                4193
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0582P)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         7224
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.13580(17) -0.17550(13) 0.47173(5) 0.1307(4) Uani 1 1 d . . .
O1 O -0.00345(19) 0.17810(14) 0.25768(6) 0.0376(4) Uani 1 1 d . . .
O2 O -0.6531(3) -0.07898(17) 0.07988(9) 0.0795(6) Uani 1 1 d . . .
O3 O -0.5745(2) -0.23697(16) 0.12944(8) 0.0584(5) Uani 1 1 d . . .
O4 O -0.5660(2) -0.14429(19) 0.26765(8) 0.0642(5) Uani 1 1 d . . .
N1 N -0.1517(2) 0.16914(17) 0.16404(7) 0.0345(4) Uani 1 1 d . . .
N2 N -0.2987(2) 0.09841(17) 0.12236(8) 0.0368(4) Uani 1 1 d . . .
N3 N 0.2816(2) 0.36157(17) 0.24340(7) 0.0336(4) Uani 1 1 d . . .
C31 C -0.2562(3) -0.1096(2) 0.31706(10) 0.0378(5) Uani 1 1 d . . .
C29 C 0.5754(4) 0.4665(3) 0.42415(11) 0.0598(7) Uani 1 1 d . . .
H29A H 0.6542 0.4634 0.4614 0.072 Uiso 1 1 calc R . .
H29B H 0.5361 0.5467 0.4275 0.072 Uiso 1 1 calc R . .
C19 C -0.8019(4) -0.1818(3) 0.04174(14) 0.0906(11) Uani 1 1 d . . .
H19A H -0.7490 -0.2493 0.0271 0.136 Uiso 1 1 calc R . .
H19B H -0.8448 -0.1406 0.0071 0.136 Uiso 1 1 calc R . .
H19C H -0.9100 -0.2232 0.0658 0.136 Uiso 1 1 calc R . .
C12 C 0.1206(3) 0.3058(2) 0.10658(9) 0.0304(5) Uani 1 1 d . . .
C1 C -0.3935(3) -0.0082(2) 0.15377(9) 0.0332(5) Uani 1 1 d . . .
C5 C 0.0035(3) 0.3001(2) 0.16355(9) 0.0316(5) Uani 1 1 d . . .
C2 C -0.3097(3) -0.0079(2) 0.21502(9) 0.0332(5) Uani 1 1 d . . .
C17 C 0.1407(3) 0.4058(2) 0.06490(9) 0.0363(5) Uani 1 1 d . . .
H17 H 0.0856 0.4734 0.0719 0.044 Uiso 1 1 calc R . .
C30 C -0.3910(3) -0.0931(2) 0.26621(10) 0.0397(5) Uani 1 1 d . . .
C3 C -0.1531(3) 0.1093(2) 0.21723(9) 0.0313(5) Uani 1 1 d . . .
C18 C -0.5504(3) -0.1210(2) 0.12078(10) 0.0388(5) Uani 1 1 d . . .
C4 C 0.1175(3) 0.2891(2) 0.22468(9) 0.0317(5) Uani 1 1 d . . .
C20 C 0.3876(3) 0.3509(2) 0.30213(9) 0.0317(5) Uani 1 1 d . . .
C32 C -0.3189(4) -0.1315(3) 0.37646(11) 0.0562(7) Uani 1 1 d . . .
H32 H -0.4447 -0.1346 0.3840 0.067 Uiso 1 1 calc R . .
C16 C 0.2422(3) 0.4070(2) 0.01258(10) 0.0425(6) Uani 1 1 d . . .
H16 H 0.2538 0.4748 -0.0153 0.051 Uiso 1 1 calc R . .
C36 C -0.0700(3) -0.1075(2) 0.30687(11) 0.0449(6) Uani 1 1 d . . .
H36 H -0.0251 -0.0908 0.2677 0.054 Uiso 1 1 calc R . .
C15 C 0.3244(3) 0.3092(3) 0.00200(11) 0.0466(6) Uani 1 1 d . . .
H15 H 0.3925 0.3101 -0.0330 0.056 Uiso 1 1 calc R . .
C11 C 0.0470(3) 0.5438(2) 0.19207(10) 0.0436(6) Uani 1 1 d . . .
H11 H 0.1730 0.5530 0.2073 0.052 Uiso 1 1 calc R . .
C26 C 0.2716(3) 0.3469(3) 0.35886(10) 0.0469(6) Uani 1 1 d . . .
H26A H 0.1559 0.2679 0.3553 0.056 Uiso 1 1 calc R . .
H26B H 0.2311 0.4268 0.3614 0.056 Uiso 1 1 calc R . .
C6 C -0.0752(3) 0.4185(2) 0.16915(9) 0.0316(5) Uani 1 1 d . . .
C23 C 0.7531(4) 0.3487(4) 0.36338(14) 0.0843(11) Uani 1 1 d . . .
H23A H 0.8342 0.3448 0.3999 0.101 Uiso 1 1 calc R . .
H23B H 0.8287 0.3528 0.3277 0.101 Uiso 1 1 calc R . .
C8 C -0.3255(3) 0.5170(2) 0.14824(10) 0.0442(6) Uani 1 1 d . . .
H8 H -0.4520 0.5079 0.1336 0.053 Uiso 1 1 calc R . .
C14 C 0.3065(3) 0.2092(3) 0.04321(11) 0.0518(6) Uani 1 1 d . . .
H14 H 0.3630 0.1424 0.0361 0.062 Uiso 1 1 calc R . .
C13 C 0.2048(3) 0.2073(2) 0.09522(11) 0.0446(6) Uani 1 1 d . . .
H13 H 0.1931 0.1389 0.1228 0.054 Uiso 1 1 calc R . .
C27 C 0.3979(3) 0.3417(3) 0.41742(10) 0.0544(7) Uani 1 1 d . . .
H27 H 0.3220 0.3378 0.4535 0.065 Uiso 1 1 calc R . .
C24 C 0.5750(5) 0.2226(3) 0.35705(13) 0.0755(9) Uani 1 1 d . . .
H24 H 0.6163 0.1421 0.3549 0.091 Uiso 1 1 calc R . .
C21 C 0.5672(3) 0.4771(3) 0.30964(11) 0.0530(7) Uani 1 1 d . . .
H21A H 0.5271 0.5571 0.3120 0.064 Uiso 1 1 calc R . .
H21B H 0.6430 0.4827 0.2739 0.064 Uiso 1 1 calc R . .
C34 C -0.0139(4) -0.1482(3) 0.41196(13) 0.0673(8) Uani 1 1 d . . .
C7 C -0.2627(3) 0.4061(2) 0.14736(9) 0.0393(5) Uani 1 1 d . . .
H7 H -0.3465 0.3225 0.1321 0.047 Uiso 1 1 calc R . .
C22 C 0.6927(3) 0.4726(3) 0.36825(11) 0.0597(8) Uani 1 1 d . . .
H22 H 0.8081 0.5534 0.3722 0.072 Uiso 1 1 calc R . .
C9 C -0.2035(3) 0.6408(2) 0.17040(10) 0.0477(6) Uani 1 1 d . . .
H9 H -0.2469 0.7155 0.1706 0.057 Uiso 1 1 calc R . .
C10 C -0.0163(3) 0.6545(2) 0.19245(11) 0.0499(6) Uani 1 1 d . . .
H10 H 0.0669 0.7385 0.2075 0.060 Uiso 1 1 calc R . .
C25 C 0.4511(4) 0.2266(3) 0.29809(11) 0.0557(7) Uani 1 1 d . . .
H25A H 0.5262 0.2296 0.2624 0.067 Uiso 1 1 calc R . .
H25B H 0.3381 0.1459 0.2935 0.067 Uiso 1 1 calc R . .
C35 C 0.0504(4) -0.1298(3) 0.35365(13) 0.0590(7) Uani 1 1 d . . .
H35 H 0.1736 -0.1323 0.3459 0.071 Uiso 1 1 calc R . .
C28 C 0.4564(4) 0.2176(3) 0.41275(13) 0.0743(9) Uani 1 1 d . . .
H28A H 0.3414 0.1381 0.4087 0.089 Uiso 1 1 calc R . .
H28B H 0.5329 0.2115 0.4500 0.089 Uiso 1 1 calc R . .
C33 C -0.1966(5) -0.1483(3) 0.42385(13) 0.0729(9) Uani 1 1 d . . .
H33 H -0.2375 -0.1597 0.4637 0.087 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Cl1 C34 1.732(3) . ?
O1 C3 1.352(2) . ?
O1 C4 1.449(2) . ?
O2 C18 1.300(3) . ?
O2 C19 1.454(3) . ?
O3 C18 1.189(3) . ?
O4 C30 1.216(2) . ?
N1 C3 1.326(2) . ?
N1 N2 1.362(2) . ?
N1 C5 1.470(2) . ?
N2 C1 1.336(2) . ?
N3 C4 1.230(2) . ?
N3 C20 1.476(2) . ?
C31 C36 1.379(3) . ?
C31 C32 1.393(3) . ?
C31 C30 1.484(3) . ?
C29 C27 1.510(3) . ?
C29 C22 1.516(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C12 C17 1.378(3) . ?
C12 C13 1.379(3) . ?
C12 C5 1.535(3) . ?
C1 C2 1.429(3) . ?
C1 C18 1.485(3) . ?
C5 C6 1.525(3) . ?
C5 C4 1.549(3) . ?
C2 C3 1.378(3) . ?
C2 C30 1.473(3) . ?
C17 C16 1.389(3) . ?
C17 H17 0.9300 . ?
C20 C25 1.512(3) . ?
C20 C26 1.528(3) . ?
C20 C21 1.529(3) . ?
C32 C33 1.372(4) . ?
C32 H32 0.9300 . ?
C16 C15 1.359(3) . ?
C16 H16 0.9300 . ?
C36 C35 1.375(3) . ?
C36 H36 0.9300 . ?
C15 C14 1.372(3) . ?
C15 H15 0.9300 . ?
C11 C10 1.374(3) . ?
C11 C6 1.386(3) . ?
C11 H11 0.9300 . ?
C26 C27 1.537(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C6 C7 1.381(3) . ?
C23 C22 1.496(4) . ?
C23 C24 1.521(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C8 C9 1.369(3) . ?
C8 C7 1.375(3) . ?
C8 H8 0.9300 . ?
C14 C13 1.384(3) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C27 C28 1.490(4) . ?
C27 H27 0.9800 . ?
C24 C28 1.519(4) . ?
C24 C25 1.530(3) . ?
C24 H24 0.9800 . ?
C21 C22 1.532(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C34 C33 1.369(4) . ?
C34 C35 1.373(4) . ?
C7 H7 0.9300 . ?
C22 H22 0.9800 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C35 H35 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C4 106.13(15) . . ?
C18 O2 C19 117.0(2) . . ?
C3 N1 N2 113.09(16) . . ?
C3 N1 C5 113.17(16) . . ?
N2 N1 C5 133.69(17) . . ?
C1 N2 N1 102.47(16) . . ?
C4 N3 C20 126.43(18) . . ?
C36 C31 C32 118.6(2) . . ?
C36 C31 C30 121.58(19) . . ?
C32 C31 C30 119.8(2) . . ?
C27 C29 C22 109.20(19) . . ?
C27 C29 H29A 109.8 . . ?
C22 C29 H29A 109.8 . . ?
C27 C29 H29B 109.8 . . ?
C22 C29 H29B 109.8 . . ?
H29A C29 H29B 108.3 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C12 C13 118.27(18) . . ?
C17 C12 C5 121.71(18) . . ?
C13 C12 C5 120.00(19) . . ?
N2 C1 C2 113.76(17) . . ?
N2 C1 C18 119.01(19) . . ?
C2 C1 C18 126.57(19) . . ?
N1 C5 C6 111.87(15) . . ?
N1 C5 C12 110.53(15) . . ?
C6 C5 C12 112.57(16) . . ?
N1 C5 C4 97.82(15) . . ?
C6 C5 C4 109.98(15) . . ?
C12 C5 C4 113.23(15) . . ?
C3 C2 C1 101.36(17) . . ?
C3 C2 C30 128.46(19) . . ?
C1 C2 C30 129.03(18) . . ?
C12 C17 C16 120.9(2) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
O4 C30 C2 120.3(2) . . ?
O4 C30 C31 121.0(2) . . ?
C2 C30 C31 118.73(18) . . ?
N1 C3 O1 112.73(17) . . ?
N1 C3 C2 109.30(18) . . ?
O1 C3 C2 137.96(19) . . ?
O3 C18 O2 123.9(2) . . ?
O3 C18 C1 123.5(2) . . ?
O2 C18 C1 112.5(2) . . ?
N3 C4 O1 124.66(19) . . ?
N3 C4 C5 127.04(18) . . ?
O1 C4 C5 108.29(15) . . ?
N3 C20 C25 109.31(16) . . ?
N3 C20 C26 113.96(16) . . ?
C25 C20 C26 109.87(19) . . ?
N3 C20 C21 106.49(17) . . ?
C25 C20 C21 109.28(18) . . ?
C26 C20 C21 107.81(17) . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C35 C36 C31 121.1(2) . . ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C10 C11 C6 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C20 C26 C27 109.62(17) . . ?
C20 C26 H26A 109.7 . . ?
C27 C26 H26A 109.7 . . ?
C20 C26 H26B 109.7 . . ?
C27 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
C7 C6 C11 119.0(2) . . ?
C7 C6 C5 121.06(18) . . ?
C11 C6 C5 119.71(17) . . ?
C22 C23 C24 110.2(2) . . ?
C22 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C28 C27 C29 110.4(2) . . ?
C28 C27 C26 108.8(2) . . ?
C29 C27 C26 110.0(2) . . ?
C28 C27 H27 109.2 . . ?
C29 C27 H27 109.2 . . ?
C26 C27 H27 109.2 . . ?
C28 C24 C23 109.3(2) . . ?
C28 C24 C25 109.6(2) . . ?
C23 C24 C25 109.5(3) . . ?
C28 C24 H24 109.5 . . ?
C23 C24 H24 109.5 . . ?
C25 C24 H24 109.5 . . ?
C20 C21 C22 110.5(2) . . ?
C20 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C33 C34 C35 121.3(3) . . ?
C33 C34 Cl1 118.9(2) . . ?
C35 C34 Cl1 119.8(2) . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C23 C22 C29 109.6(2) . . ?
C23 C22 C21 108.5(2) . . ?
C29 C22 C21 109.5(2) . . ?
C23 C22 H22 109.7 . . ?
C29 C22 H22 109.7 . . ?
C21 C22 H22 109.7 . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C20 C25 C24 108.93(18) . . ?
C20 C25 H25A 109.9 . . ?
C24 C25 H25A 109.9 . . ?
C20 C25 H25B 109.9 . . ?
C24 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
C34 C35 C36 119.0(2) . . ?
C34 C35 H35 120.5 . . ?
C36 C35 H35 120.5 . . ?
C27 C28 C24 109.8(2) . . ?
C27 C28 H28A 109.7 . . ?
C24 C28 H28A 109.7 . . ?
C27 C28 H28B 109.7 . . ?
C24 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
C34 C33 C32 119.4(2) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C1 1.1(2) . . . . ?
C5 N1 N2 C1 -176.04(19) . . . . ?
N1 N2 C1 C2 -0.3(2) . . . . ?
N1 N2 C1 C18 -171.58(17) . . . . ?
C3 N1 C5 C6 -104.64(19) . . . . ?
N2 N1 C5 C6 72.5(2) . . . . ?
C3 N1 C5 C12 129.08(18) . . . . ?
N2 N1 C5 C12 -53.8(3) . . . . ?
C3 N1 C5 C4 10.62(19) . . . . ?
N2 N1 C5 C4 -172.26(19) . . . . ?
C17 C12 C5 N1 123.1(2) . . . . ?
C13 C12 C5 N1 -55.2(2) . . . . ?
C17 C12 C5 C6 -2.8(3) . . . . ?
C13 C12 C5 C6 178.93(17) . . . . ?
C17 C12 C5 C4 -128.3(2) . . . . ?
C13 C12 C5 C4 53.4(2) . . . . ?
N2 C1 C2 C3 -0.5(2) . . . . ?
C18 C1 C2 C3 169.99(19) . . . . ?
N2 C1 C2 C30 167.9(2) . . . . ?
C18 C1 C2 C30 -21.6(3) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
C5 C12 C17 C16 -177.98(18) . . . . ?
C3 C2 C30 O4 141.3(2) . . . . ?
C1 C2 C30 O4 -24.1(3) . . . . ?
C3 C2 C30 C31 -35.9(3) . . . . ?
C1 C2 C30 C31 158.7(2) . . . . ?
C36 C31 C30 O4 151.2(2) . . . . ?
C32 C31 C30 O4 -27.0(3) . . . . ?
C36 C31 C30 C2 -31.6(3) . . . . ?
C32 C31 C30 C2 150.2(2) . . . . ?
N2 N1 C3 O1 178.15(15) . . . . ?
C5 N1 C3 O1 -4.1(2) . . . . ?
N2 N1 C3 C2 -1.5(2) . . . . ?
C5 N1 C3 C2 176.26(15) . . . . ?
C4 O1 C3 N1 -5.3(2) . . . . ?
C4 O1 C3 C2 174.2(2) . . . . ?
C1 C2 C3 N1 1.1(2) . . . . ?
C30 C2 C3 N1 -167.3(2) . . . . ?
C1 C2 C3 O1 -178.4(2) . . . . ?
C30 C2 C3 O1 13.2(4) . . . . ?
C19 O2 C18 O3 -1.8(4) . . . . ?
C19 O2 C18 C1 175.7(2) . . . . ?
N2 C1 C18 O3 139.8(2) . . . . ?
C2 C1 C18 O3 -30.2(3) . . . . ?
N2 C1 C18 O2 -37.7(3) . . . . ?
C2 C1 C18 O2 152.3(2) . . . . ?
C20 N3 C4 O1 0.0(3) . . . . ?
C20 N3 C4 C5 179.27(16) . . . . ?
C3 O1 C4 N3 -168.58(19) . . . . ?
C3 O1 C4 C5 12.05(18) . . . . ?
N1 C5 C4 N3 167.39(19) . . . . ?
C6 C5 C4 N3 -75.9(2) . . . . ?
C12 C5 C4 N3 51.0(3) . . . . ?
N1 C5 C4 O1 -13.26(17) . . . . ?
C6 C5 C4 O1 103.48(16) . . . . ?
C12 C5 C4 O1 -129.62(16) . . . . ?
C4 N3 C20 C25 72.0(2) . . . . ?
C4 N3 C20 C26 -51.3(3) . . . . ?
C4 N3 C20 C21 -170.06(19) . . . . ?
C36 C31 C32 C33 1.0(4) . . . . ?
C30 C31 C32 C33 179.3(2) . . . . ?
C12 C17 C16 C15 -0.4(3) . . . . ?
C32 C31 C36 C35 1.6(3) . . . . ?
C30 C31 C36 C35 -176.7(2) . . . . ?
C17 C16 C15 C14 0.1(3) . . . . ?
N3 C20 C26 C27 -177.66(18) . . . . ?
C25 C20 C26 C27 59.3(2) . . . . ?
C21 C20 C26 C27 -59.7(2) . . . . ?
C10 C11 C6 C7 -0.8(3) . . . . ?
C10 C11 C6 C5 174.29(19) . . . . ?
N1 C5 C6 C7 -28.9(3) . . . . ?
C12 C5 C6 C7 96.3(2) . . . . ?
C4 C5 C6 C7 -136.46(19) . . . . ?
N1 C5 C6 C11 156.13(18) . . . . ?
C12 C5 C6 C11 -78.7(2) . . . . ?
C4 C5 C6 C11 48.6(2) . . . . ?
C16 C15 C14 C13 0.2(4) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
C5 C12 C13 C14 178.33(19) . . . . ?
C15 C14 C13 C12 -0.2(4) . . . . ?
C22 C29 C27 C28 59.9(3) . . . . ?
C22 C29 C27 C26 -60.1(3) . . . . ?
C20 C26 C27 C28 -60.0(3) . . . . ?
C20 C26 C27 C29 61.0(3) . . . . ?
C22 C23 C24 C28 -58.8(3) . . . . ?
C22 C23 C24 C25 61.3(3) . . . . ?
N3 C20 C21 C22 -177.49(18) . . . . ?
C25 C20 C21 C22 -59.5(2) . . . . ?
C26 C20 C21 C22 59.8(2) . . . . ?
C9 C8 C7 C6 0.2(3) . . . . ?
C11 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C7 C8 -174.64(18) . . . . ?
C24 C23 C22 C29 59.6(3) . . . . ?
C24 C23 C22 C21 -60.0(3) . . . . ?
C27 C29 C22 C23 -59.6(3) . . . . ?
C27 C29 C22 C21 59.4(3) . . . . ?
C20 C21 C22 C23 59.4(3) . . . . ?
C20 C21 C22 C29 -60.2(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C6 C11 C10 C9 0.6(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
N3 C20 C25 C24 175.4(2) . . . . ?
C26 C20 C25 C24 -58.8(3) . . . . ?
C21 C20 C25 C24 59.2(3) . . . . ?
C28 C24 C25 C20 59.7(3) . . . . ?
C23 C24 C25 C20 -60.2(3) . . . . ?
C33 C34 C35 C36 1.7(4) . . . . ?
Cl1 C34 C35 C36 -179.7(2) . . . . ?
C31 C36 C35 C34 -3.0(4) . . . . ?
C29 C27 C28 C24 -59.6(3) . . . . ?
C26 C27 C28 C24 61.1(3) . . . . ?
C23 C24 C28 C27 58.4(3) . . . . ?
C25 C24 C28 C27 -61.6(3) . . . . ?
C35 C34 C33 C32 0.9(5) . . . . ?
Cl1 C34 C33 C32 -177.8(2) . . . . ?
C31 C32 C33 C34 -2.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.841
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.048
