# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ss046a
_database_code_depnum_ccdc_archive 'CCDC 1437744'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H34 N2 O10'
_chemical_formula_weight         822.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   11.9899(9)
_cell_length_b                   12.8443(13)
_cell_length_c                   13.7345(9)
_cell_angle_alpha                106.461(7)
_cell_angle_beta                 90.280(6)
_cell_angle_gamma                95.846(7)
_cell_volume                     2016.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3115
_cell_measurement_theta_min      3.3350
_cell_measurement_theta_max      69.0540

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_T_max  0.8590
_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_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 16.0309
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14085
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         71.36
_reflns_number_total             7670
_reflns_number_gt                4616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1996P)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    RIDING'
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7670
_refine_ls_number_parameters     560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0947
_refine_ls_wR_factor_ref         0.3265
_refine_ls_wR_factor_gt          0.2736
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.1748(4) 0.3525(3) 0.0400(2) 0.0919(11) Uani 1 1 d . . .
O2 O 0.1548(3) 0.2029(3) 0.0795(3) 0.0889(11) Uani 1 1 d . . .
O3 O 0.0114(3) 0.5390(2) 0.3569(2) 0.0690(8) Uani 1 1 d . . .
O4 O -0.0539(2) 0.4002(2) 0.4123(2) 0.0631(7) Uani 1 1 d . . .
O5 O 0.2102(2) 0.2286(2) 0.2934(2) 0.0562(7) Uani 1 1 d . . .
O6 O 0.2707(4) 0.1836(3) 0.5839(3) 0.1093(15) Uani 1 1 d . . .
O7 O 0.2891(4) 0.3214(3) 0.5271(2) 0.0920(11) Uani 1 1 d . . .
O8 O 0.4936(3) 0.5381(3) 0.8344(3) 0.0805(9) Uani 1 1 d . . .
O9 O 0.5290(2) 0.4075(3) 0.9014(2) 0.0712(8) Uani 1 1 d . . .
O10 O 0.2210(2) 0.2367(2) 0.8003(2) 0.0585(7) Uani 1 1 d . . .
N1 N 0.1915(3) 0.2970(3) 0.0958(2) 0.0636(9) Uani 1 1 d . . .
N2 N 0.2574(3) 0.2767(3) 0.5905(3) 0.0655(9) Uani 1 1 d . . .
C1 C 0.2634(3) 0.3535(3) 0.1929(3) 0.0566(9) Uani 1 1 d . . .
H1 H 0.3325 0.3890 0.1735 0.068 Uiso 1 1 calc R . .
C2 C 0.1996(3) 0.4426(3) 0.2616(3) 0.0554(9) Uani 1 1 d . . .
H2 H 0.1571 0.4739 0.2177 0.066 Uiso 1 1 calc R . .
C3 C 0.2816(3) 0.5335(3) 0.3272(3) 0.0580(9) Uani 1 1 d . . .
C4 C 0.3122(4) 0.6241(4) 0.2956(4) 0.0740(12) Uani 1 1 d . . .
H4 H 0.2804 0.6300 0.2357 0.089 Uiso 1 1 calc R . .
C5 C 0.3890(5) 0.7060(4) 0.3510(5) 0.0885(15) Uani 1 1 d . . .
H5 H 0.4085 0.7672 0.3287 0.106 Uiso 1 1 calc R . .
C6 C 0.4370(5) 0.6987(4) 0.4389(5) 0.0940(17) Uani 1 1 d . . .
H6 H 0.4884 0.7548 0.4769 0.113 Uiso 1 1 calc R . .
C7 C 0.4089(5) 0.6080(5) 0.4705(4) 0.0910(16) Uani 1 1 d . . .
H7 H 0.4427 0.6016 0.5293 0.109 Uiso 1 1 calc R . .
C8 C 0.3310(4) 0.5261(4) 0.4157(4) 0.0750(13) Uani 1 1 d . . .
H8 H 0.3115 0.4652 0.4384 0.090 Uiso 1 1 calc R . .
C9 C 0.2951(3) 0.2716(3) 0.2435(3) 0.0527(8) Uani 1 1 d . . .
C10 C 0.3972(3) 0.2406(3) 0.2404(3) 0.0573(9) Uani 1 1 d . . .
H10 H 0.4472 0.2739 0.2040 0.069 Uiso 1 1 calc R . .
C11 C 0.4454(4) 0.1623(3) 0.2846(3) 0.0576(9) Uani 1 1 d . . .
C12 C 0.5570(4) 0.1465(4) 0.2668(4) 0.0758(13) Uani 1 1 d . . .
H12 H 0.5985 0.1865 0.2300 0.091 Uiso 1 1 calc R . .
C13 C 0.6073(5) 0.0724(5) 0.3031(4) 0.0900(16) Uani 1 1 d . . .
H13 H 0.6823 0.0633 0.2905 0.108 Uiso 1 1 calc R . .
C14 C 0.5489(5) 0.0121(4) 0.3571(4) 0.0900(17) Uani 1 1 d . . .
H14 H 0.5832 -0.0384 0.3806 0.108 Uiso 1 1 calc R . .
C15 C 0.4387(5) 0.0273(4) 0.3761(4) 0.0821(14) Uani 1 1 d . . .
H15 H 0.3980 -0.0136 0.4126 0.098 Uiso 1 1 calc R . .
C16 C 0.3870(4) 0.1022(3) 0.3418(3) 0.0670(11) Uani 1 1 d . . .
H16 H 0.3128 0.1127 0.3570 0.080 Uiso 1 1 calc R . .
C17 C 0.1239(3) 0.2882(3) 0.3282(3) 0.0495(8) Uani 1 1 d . . .
C18 C 0.1170(3) 0.3889(3) 0.3185(3) 0.0522(8) Uani 1 1 d . . .
C19 C 0.0240(3) 0.4488(3) 0.3618(3) 0.0553(9) Uani 1 1 d . . .
C20 C -0.0493(3) 0.2959(3) 0.4172(3) 0.0580(9) Uani 1 1 d . . .
C21 C 0.0374(3) 0.2356(3) 0.3771(3) 0.0555(9) Uani 1 1 d . . .
C22 C 0.0339(4) 0.1276(4) 0.3812(3) 0.0646(10) Uani 1 1 d . . .
H22 H 0.0910 0.0856 0.3536 0.078 Uiso 1 1 calc R . .
C23 C -0.0539(4) 0.0837(4) 0.4259(4) 0.0747(12) Uani 1 1 d . . .
H23 H -0.0566 0.0117 0.4280 0.090 Uiso 1 1 calc R . .
C24 C -0.1384(4) 0.1466(4) 0.4680(4) 0.0797(13) Uani 1 1 d . . .
H24 H -0.1972 0.1166 0.4988 0.096 Uiso 1 1 calc R . .
C25 C -0.1364(4) 0.2525(4) 0.4649(4) 0.0716(12) Uani 1 1 d . . .
H25 H -0.1927 0.2947 0.4943 0.086 Uiso 1 1 calc R . .
C26 C 0.1978(3) 0.3440(3) 0.6807(3) 0.0586(9) Uani 1 1 d . . .
H26 H 0.1375 0.3761 0.6549 0.070 Uiso 1 1 calc R . .
C27 C 0.2818(3) 0.4370(3) 0.7443(3) 0.0584(9) Uani 1 1 d . . .
H27 H 0.3302 0.4643 0.6975 0.070 Uiso 1 1 calc R . .
C28 C 0.2219(4) 0.5310(3) 0.8068(3) 0.0592(9) Uani 1 1 d . . .
C29 C 0.2211(4) 0.6256(3) 0.7776(4) 0.0725(12) Uani 1 1 d . . .
H29 H 0.2585 0.6318 0.7200 0.087 Uiso 1 1 calc R . .
C30 C 0.1658(5) 0.7105(4) 0.8327(5) 0.0900(16) Uani 1 1 d . . .
H30 H 0.1668 0.7740 0.8127 0.108 Uiso 1 1 calc R . .
C31 C 0.1090(5) 0.7023(4) 0.9172(5) 0.0912(17) Uani 1 1 d . . .
H31 H 0.0710 0.7595 0.9540 0.109 Uiso 1 1 calc R . .
C32 C 0.1089(5) 0.6102(4) 0.9463(4) 0.0873(15) Uani 1 1 d . . .
H32 H 0.0706 0.6048 1.0037 0.105 Uiso 1 1 calc R . .
C33 C 0.1645(4) 0.5243(4) 0.8927(4) 0.0745(12) Uani 1 1 d . . .
H33 H 0.1636 0.4617 0.9141 0.089 Uiso 1 1 calc R . .
C34 C 0.1472(3) 0.2717(3) 0.7396(3) 0.0562(9) Uani 1 1 d . . .
C35 C 0.0390(3) 0.2395(3) 0.7353(3) 0.0584(9) Uani 1 1 d . . .
H35 H -0.0030 0.2669 0.6929 0.070 Uiso 1 1 calc R . .
C36 C -0.0273(4) 0.1684(3) 0.7854(3) 0.0606(10) Uani 1 1 d . . .
C37 C -0.1438(4) 0.1636(4) 0.7789(4) 0.0755(12) Uani 1 1 d . . .
H37 H -0.1765 0.2056 0.7438 0.091 Uiso 1 1 calc R . .
C38 C -0.2115(5) 0.0982(4) 0.8233(4) 0.0895(15) Uani 1 1 d . . .
H38 H -0.2889 0.0990 0.8205 0.107 Uiso 1 1 calc R . .
C39 C -0.1662(5) 0.0322(4) 0.8713(4) 0.0908(16) Uani 1 1 d . . .
H39 H -0.2123 -0.0135 0.8996 0.109 Uiso 1 1 calc R . .
C40 C -0.0521(5) 0.0337(4) 0.8774(4) 0.0855(15) Uani 1 1 d . . .
H40 H -0.0209 -0.0115 0.9099 0.103 Uiso 1 1 calc R . .
C41 C 0.0179(4) 0.1016(4) 0.8361(3) 0.0726(12) Uani 1 1 d . . .
H41 H 0.0953 0.1025 0.8421 0.087 Uiso 1 1 calc R . .
C42 C 0.4605(4) 0.4510(4) 0.8469(3) 0.0636(10) Uani 1 1 d . . .
C43 C 0.3537(3) 0.3907(3) 0.8076(3) 0.0539(9) Uani 1 1 d . . .
C44 C 0.3217(3) 0.2967(3) 0.8299(3) 0.0539(9) Uani 1 1 d . . .
C45 C 0.3943(3) 0.2518(3) 0.8881(3) 0.0571(9) Uani 1 1 d . . .
C46 C 0.4985(4) 0.3093(4) 0.9201(3) 0.0623(10) Uani 1 1 d . . .
C47 C 0.3666(4) 0.1554(4) 0.9143(3) 0.0687(11) Uani 1 1 d . . .
H47 H 0.2966 0.1161 0.8954 0.082 Uiso 1 1 calc R . .
C48 C 0.4433(5) 0.1182(4) 0.9682(4) 0.0822(14) Uani 1 1 d . . .
H48 H 0.4246 0.0538 0.9856 0.099 Uiso 1 1 calc R . .
C49 C 0.5468(5) 0.1753(4) 0.9964(4) 0.0823(14) Uani 1 1 d . . .
H49 H 0.5984 0.1484 1.0312 0.099 Uiso 1 1 calc R . .
C50 C 0.5747(4) 0.2710(4) 0.9740(4) 0.0780(13) Uani 1 1 d . . .
H50 H 0.6443 0.3104 0.9948 0.094 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.213(4) . ?
O2 N1 1.201(5) . ?
O3 C19 1.204(4) . ?
O4 C20 1.367(5) . ?
O4 C19 1.369(5) . ?
O5 C17 1.358(4) . ?
O5 C9 1.385(4) . ?
O6 N2 1.201(5) . ?
O7 N2 1.214(4) . ?
O8 C42 1.208(5) . ?
O9 C42 1.368(5) . ?
O9 C46 1.371(5) . ?
O10 C44 1.359(5) . ?
O10 C34 1.402(4) . ?
N1 C1 1.538(5) . ?
N2 C26 1.523(5) . ?
C1 C9 1.491(5) . ?
C1 C2 1.536(5) . ?
C1 H1 0.9800 . ?
C2 C18 1.497(5) . ?
C2 C3 1.517(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.371(6) . ?
C3 C8 1.380(6) . ?
C4 C5 1.370(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.323(5) . ?
C10 C11 1.476(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(6) . ?
C11 C16 1.393(6) . ?
C12 C13 1.379(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.349(5) . ?
C17 C21 1.450(5) . ?
C18 C19 1.453(5) . ?
C20 C21 1.383(6) . ?
C20 C25 1.387(6) . ?
C21 C22 1.401(5) . ?
C22 C23 1.372(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(6) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C34 1.484(5) . ?
C26 C27 1.535(6) . ?
C26 H26 0.9800 . ?
C27 C43 1.498(5) . ?
C27 C28 1.518(6) . ?
C27 H27 0.9800 . ?
C28 C29 1.384(5) . ?
C28 C33 1.387(6) . ?
C29 C30 1.373(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.372(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.351(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.378(7) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C35 1.317(6) . ?
C35 C36 1.467(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.393(6) . ?
C36 C41 1.395(6) . ?
C37 C38 1.376(7) . ?
C37 H37 0.9300 . ?
C38 C39 1.363(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.368(8) . ?
C39 H39 0.9300 . ?
C40 C41 1.387(7) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 C43 1.444(6) . ?
C43 C44 1.347(5) . ?
C44 C45 1.445(5) . ?
C45 C46 1.386(6) . ?
C45 C47 1.394(6) . ?
C46 C50 1.384(6) . ?
C47 C48 1.380(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.370(8) . ?
C48 H48 0.9300 . ?
C49 C50 1.360(7) . ?
C49 H49 0.9300 . ?
C50 H50 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
C20 O4 C19 121.7(3) . . ?
C17 O5 C9 118.9(3) . . ?
C42 O9 C46 121.8(3) . . ?
C44 O10 C34 118.5(3) . . ?
O2 N1 O1 124.0(4) . . ?
O2 N1 C1 119.5(3) . . ?
O1 N1 C1 116.5(4) . . ?
O6 N2 O7 122.8(4) . . ?
O6 N2 C26 120.2(3) . . ?
O7 N2 C26 117.0(3) . . ?
C9 C1 C2 113.4(3) . . ?
C9 C1 N1 110.5(3) . . ?
C2 C1 N1 108.8(3) . . ?
C9 C1 H1 108.0 . . ?
C2 C1 H1 108.0 . . ?
N1 C1 H1 108.0 . . ?
C18 C2 C3 115.3(3) . . ?
C18 C2 C1 107.9(3) . . ?
C3 C2 C1 110.2(3) . . ?
C18 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C4 C3 C8 118.4(4) . . ?
C4 C3 C2 119.2(4) . . ?
C8 C3 C2 122.3(4) . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 119.4(5) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 120.4(5) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C3 120.5(5) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C10 C9 O5 121.6(3) . . ?
C10 C9 C1 122.6(3) . . ?
O5 C9 C1 115.8(3) . . ?
C9 C10 C11 131.2(4) . . ?
C9 C10 H10 114.4 . . ?
C11 C10 H10 114.4 . . ?
C12 C11 C16 117.7(4) . . ?
C12 C11 C10 117.4(4) . . ?
C16 C11 C10 125.0(4) . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 118.7(5) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C16 121.1(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 120.4(5) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C18 C17 O5 123.5(3) . . ?
C18 C17 C21 121.3(3) . . ?
O5 C17 C21 115.2(3) . . ?
C17 C18 C19 119.8(4) . . ?
C17 C18 C2 123.1(3) . . ?
C19 C18 C2 117.1(3) . . ?
O3 C19 O4 117.8(4) . . ?
O3 C19 C18 124.1(4) . . ?
O4 C19 C18 118.1(3) . . ?
O4 C20 C21 122.2(4) . . ?
O4 C20 C25 116.7(4) . . ?
C21 C20 C25 121.0(4) . . ?
C20 C21 C22 118.9(4) . . ?
C20 C21 C17 116.7(3) . . ?
C22 C21 C17 124.3(4) . . ?
C23 C22 C21 120.0(4) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.0(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.9(4) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C20 119.1(4) . . ?
C24 C25 H25 120.5 . . ?
C20 C25 H25 120.5 . . ?
C34 C26 N2 109.5(3) . . ?
C34 C26 C27 113.0(3) . . ?
N2 C26 C27 108.9(3) . . ?
C34 C26 H26 108.5 . . ?
N2 C26 H26 108.5 . . ?
C27 C26 H26 108.5 . . ?
C43 C27 C28 113.1(3) . . ?
C43 C27 C26 108.2(3) . . ?
C28 C27 C26 111.2(3) . . ?
C43 C27 H27 108.1 . . ?
C28 C27 H27 108.1 . . ?
C26 C27 H27 108.1 . . ?
C29 C28 C33 118.0(4) . . ?
C29 C28 C27 120.3(4) . . ?
C33 C28 C27 121.7(4) . . ?
C30 C29 C28 120.8(5) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C31 C30 C29 120.4(5) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 119.4(5) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C31 C32 C33 121.3(5) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C32 C33 C28 120.1(5) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?
C35 C34 O10 120.5(3) . . ?
C35 C34 C26 122.9(3) . . ?
O10 C34 C26 116.6(3) . . ?
C34 C35 C36 131.7(4) . . ?
C34 C35 H35 114.2 . . ?
C36 C35 H35 114.2 . . ?
C37 C36 C41 117.2(4) . . ?
C37 C36 C35 118.2(4) . . ?
C41 C36 C35 124.5(4) . . ?
C38 C37 C36 121.5(5) . . ?
C38 C37 H37 119.3 . . ?
C36 C37 H37 119.3 . . ?
C39 C38 C37 120.6(5) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 119.2(5) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C39 C40 C41 121.1(5) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 H40 119.4 . . ?
C40 C41 C36 120.3(5) . . ?
C40 C41 H41 119.9 . . ?
C36 C41 H41 119.9 . . ?
O8 C42 O9 117.5(4) . . ?
O8 C42 C43 123.9(4) . . ?
O9 C42 C43 118.6(4) . . ?
C44 C43 C42 119.5(4) . . ?
C44 C43 C27 122.5(4) . . ?
C42 C43 C27 118.0(3) . . ?
C43 C44 O10 123.9(3) . . ?
C43 C44 C45 121.4(4) . . ?
O10 C44 C45 114.7(3) . . ?
C46 C45 C47 118.2(4) . . ?
C46 C45 C44 117.3(4) . . ?
C47 C45 C44 124.5(4) . . ?
O9 C46 C50 117.5(4) . . ?
O9 C46 C45 121.2(4) . . ?
C50 C46 C45 121.2(4) . . ?
C48 C47 C45 119.9(5) . . ?
C48 C47 H47 120.0 . . ?
C45 C47 H47 120.0 . . ?
C49 C48 C47 120.5(5) . . ?
C49 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C50 C49 C48 120.6(4) . . ?
C50 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
C49 C50 C46 119.5(5) . . ?
C49 C50 H50 120.3 . . ?
C46 C50 H50 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
O2 N1 C1 C9 11.4(5) . . . . ?
O1 N1 C1 C9 -169.2(4) . . . . ?
O2 N1 C1 C2 -113.6(4) . . . . ?
O1 N1 C1 C2 65.7(5) . . . . ?
C9 C1 C2 C18 -41.8(4) . . . . ?
N1 C1 C2 C18 81.6(4) . . . . ?
C9 C1 C2 C3 84.9(4) . . . . ?
N1 C1 C2 C3 -151.8(3) . . . . ?
C18 C2 C3 C4 -142.2(4) . . . . ?
C1 C2 C3 C4 95.4(4) . . . . ?
C18 C2 C3 C8 40.9(5) . . . . ?
C1 C2 C3 C8 -81.4(5) . . . . ?
C8 C3 C4 C5 -0.8(7) . . . . ?
C2 C3 C4 C5 -177.7(4) . . . . ?
C3 C4 C5 C6 0.3(8) . . . . ?
C4 C5 C6 C7 0.9(9) . . . . ?
C5 C6 C7 C8 -1.6(9) . . . . ?
C6 C7 C8 C3 1.1(8) . . . . ?
C4 C3 C8 C7 0.1(7) . . . . ?
C2 C3 C8 C7 176.9(5) . . . . ?
C17 O5 C9 C10 155.1(4) . . . . ?
C17 O5 C9 C1 -25.6(5) . . . . ?
C2 C1 C9 C10 -132.3(4) . . . . ?
N1 C1 C9 C10 105.2(4) . . . . ?
C2 C1 C9 O5 48.3(4) . . . . ?
N1 C1 C9 O5 -74.1(4) . . . . ?
O5 C9 C10 C11 -0.9(7) . . . . ?
C1 C9 C10 C11 179.8(4) . . . . ?
C9 C10 C11 C12 179.4(5) . . . . ?
C9 C10 C11 C16 0.2(7) . . . . ?
C16 C11 C12 C13 1.2(7) . . . . ?
C10 C11 C12 C13 -178.1(4) . . . . ?
C11 C12 C13 C14 0.2(8) . . . . ?
C12 C13 C14 C15 -0.8(8) . . . . ?
C13 C14 C15 C16 -0.2(8) . . . . ?
C14 C15 C16 C11 1.7(7) . . . . ?
C12 C11 C16 C15 -2.2(6) . . . . ?
C10 C11 C16 C15 177.1(4) . . . . ?
C9 O5 C17 C18 -1.3(5) . . . . ?
C9 O5 C17 C21 178.4(3) . . . . ?
O5 C17 C18 C19 -177.4(3) . . . . ?
C21 C17 C18 C19 2.9(5) . . . . ?
O5 C17 C18 C2 4.6(6) . . . . ?
C21 C17 C18 C2 -175.1(3) . . . . ?
C3 C2 C18 C17 -106.0(4) . . . . ?
C1 C2 C18 C17 17.6(5) . . . . ?
C3 C2 C18 C19 76.0(4) . . . . ?
C1 C2 C18 C19 -160.4(3) . . . . ?
C20 O4 C19 O3 176.7(3) . . . . ?
C20 O4 C19 C18 -3.9(5) . . . . ?
C17 C18 C19 O3 179.8(4) . . . . ?
C2 C18 C19 O3 -2.1(6) . . . . ?
C17 C18 C19 O4 0.5(5) . . . . ?
C2 C18 C19 O4 178.6(3) . . . . ?
C19 O4 C20 C21 4.0(6) . . . . ?
C19 O4 C20 C25 -176.1(4) . . . . ?
O4 C20 C21 C22 -177.3(3) . . . . ?
C25 C20 C21 C22 2.8(6) . . . . ?
O4 C20 C21 C17 -0.5(5) . . . . ?
C25 C20 C21 C17 179.6(4) . . . . ?
C18 C17 C21 C20 -2.9(5) . . . . ?
O5 C17 C21 C20 177.3(3) . . . . ?
C18 C17 C21 C22 173.7(4) . . . . ?
O5 C17 C21 C22 -6.0(5) . . . . ?
C20 C21 C22 C23 -1.0(6) . . . . ?
C17 C21 C22 C23 -177.5(4) . . . . ?
C21 C22 C23 C24 -0.7(7) . . . . ?
C22 C23 C24 C25 0.6(8) . . . . ?
C23 C24 C25 C20 1.1(7) . . . . ?
O4 C20 C25 C24 177.2(4) . . . . ?
C21 C20 C25 C24 -2.9(6) . . . . ?
O6 N2 C26 C34 -9.8(6) . . . . ?
O7 N2 C26 C34 169.7(4) . . . . ?
O6 N2 C26 C27 114.2(5) . . . . ?
O7 N2 C26 C27 -66.3(5) . . . . ?
C34 C26 C27 C43 43.4(4) . . . . ?
N2 C26 C27 C43 -78.5(4) . . . . ?
C34 C26 C27 C28 -81.4(4) . . . . ?
N2 C26 C27 C28 156.7(3) . . . . ?
C43 C27 C28 C29 133.9(4) . . . . ?
C26 C27 C28 C29 -104.2(4) . . . . ?
C43 C27 C28 C33 -47.6(6) . . . . ?
C26 C27 C28 C33 74.3(5) . . . . ?
C33 C28 C29 C30 0.5(7) . . . . ?
C27 C28 C29 C30 179.0(4) . . . . ?
C28 C29 C30 C31 -0.8(8) . . . . ?
C29 C30 C31 C32 0.7(8) . . . . ?
C30 C31 C32 C33 -0.2(8) . . . . ?
C31 C32 C33 C28 -0.1(8) . . . . ?
C29 C28 C33 C32 0.0(7) . . . . ?
C27 C28 C33 C32 -178.5(5) . . . . ?
C44 O10 C34 C35 -158.4(4) . . . . ?
C44 O10 C34 C26 22.5(5) . . . . ?
N2 C26 C34 C35 -104.1(5) . . . . ?
C27 C26 C34 C35 134.4(4) . . . . ?
N2 C26 C34 O10 75.0(4) . . . . ?
C27 C26 C34 O10 -46.5(5) . . . . ?
O10 C34 C35 C36 0.2(7) . . . . ?
C26 C34 C35 C36 179.2(4) . . . . ?
C34 C35 C36 C37 169.5(5) . . . . ?
C34 C35 C36 C41 -13.1(7) . . . . ?
C41 C36 C37 C38 1.9(7) . . . . ?
C35 C36 C37 C38 179.5(4) . . . . ?
C36 C37 C38 C39 -2.9(8) . . . . ?
C37 C38 C39 C40 1.8(8) . . . . ?
C38 C39 C40 C41 0.3(8) . . . . ?
C39 C40 C41 C36 -1.2(8) . . . . ?
C37 C36 C41 C40 0.1(7) . . . . ?
C35 C36 C41 C40 -177.3(4) . . . . ?
C46 O9 C42 O8 179.7(4) . . . . ?
C46 O9 C42 C43 -0.6(6) . . . . ?
O8 C42 C43 C44 -176.7(4) . . . . ?
O9 C42 C43 C44 3.6(6) . . . . ?
O8 C42 C43 C27 2.3(6) . . . . ?
O9 C42 C43 C27 -177.4(3) . . . . ?
C28 C27 C43 C44 102.2(4) . . . . ?
C26 C27 C43 C44 -21.4(5) . . . . ?
C28 C27 C43 C42 -76.8(5) . . . . ?
C26 C27 C43 C42 159.6(3) . . . . ?
C42 C43 C44 O10 177.0(4) . . . . ?
C27 C43 C44 O10 -2.0(6) . . . . ?
C42 C43 C44 C45 -3.2(6) . . . . ?
C27 C43 C44 C45 177.8(3) . . . . ?
C34 O10 C44 C43 2.6(6) . . . . ?
C34 O10 C44 C45 -177.2(3) . . . . ?
C43 C44 C45 C46 -0.1(6) . . . . ?
O10 C44 C45 C46 179.7(3) . . . . ?
C43 C44 C45 C47 179.8(4) . . . . ?
O10 C44 C45 C47 -0.4(6) . . . . ?
C42 O9 C46 C50 178.6(4) . . . . ?
C42 O9 C46 C45 -2.9(6) . . . . ?
C47 C45 C46 O9 -176.7(4) . . . . ?
C44 C45 C46 O9 3.2(6) . . . . ?
C47 C45 C46 C50 1.7(6) . . . . ?
C44 C45 C46 C50 -178.4(4) . . . . ?
C46 C45 C47 C48 -1.7(7) . . . . ?
C44 C45 C47 C48 178.5(4) . . . . ?
C45 C47 C48 C49 0.0(8) . . . . ?
C47 C48 C49 C50 1.7(8) . . . . ?
C48 C49 C50 C46 -1.6(8) . . . . ?
O9 C46 C50 C49 178.4(4) . . . . ?
C45 C46 C50 C49 -0.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        71.36
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.103
####################################################################### 
# 
# 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_ss049
_database_code_depnum_ccdc_archive 'CCDC 1437745'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 N O5'
_chemical_formula_weight         411.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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   P21

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

_cell_length_a                   9.1585(3)
_cell_length_b                   15.4867(4)
_cell_length_c                   15.0435(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.598(3)
_cell_angle_gamma                90.00
_cell_volume                     2033.84(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6357
_cell_measurement_theta_min      3.8590
_cell_measurement_theta_max      27.9480

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16952
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6580
_reflns_number_gt                4820
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.5138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_number_reflns         6580
_refine_ls_number_parameters     559
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.901
_refine_ls_shift/su_mean         0.211

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
09 O -0.0978(5) 0.7702(4) 0.5928(3) 0.0752(17) Uani 1 1 d . . .
06 O 0.1025(6) 0.7761(4) 0.2996(4) 0.0748(15) Uani 1 1 d . . .
07 O -0.1384(6) 0.7863(4) 0.2861(3) 0.0698(13) Uani 1 1 d . . .
08 O 0.2520(5) 0.6472(3) 0.4548(3) 0.0527(11) Uani 1 1 d . . .
010 O 0.1469(5) 0.7892(4) 0.6590(3) 0.0643(13) Uani 1 1 d . . .
N2 N -0.0159(6) 0.7470(4) 0.3084(3) 0.0514(14) Uani 1 1 d . . .
C26 C -0.0147(7) 0.6583(4) 0.3542(4) 0.0428(14) Uani 1 1 d . . .
H26 H -0.0882 0.6210 0.3098 0.051 Uiso 1 1 calc R . .
C27 C -0.0681(6) 0.6689(4) 0.4407(4) 0.0415(14) Uani 1 1 d . . .
H27 H -0.1522 0.7108 0.4260 0.050 Uiso 1 1 calc R . .
C28 C 0.0634(7) 0.7061(4) 0.5175(4) 0.0437(14) Uani 1 1 d . . .
C29 C 0.0282(8) 0.7568(5) 0.5893(4) 0.0520(16) Uani 1 1 d . . .
C30 C 0.2998(8) 0.7785(5) 0.6633(4) 0.0564(17) Uani 1 1 d . . .
C31 C 0.4067(9) 0.8141(7) 0.7334(5) 0.087(3) Uani 1 1 d . . .
H31 H 0.3779 0.8446 0.7787 0.104 Uiso 1 1 calc R . .
C32 C 0.5601(10) 0.8070(8) 0.7407(6) 0.089(3) Uani 1 1 d . . .
H32 H 0.6344 0.8349 0.7882 0.107 Uiso 1 1 calc R . .
C33 C 0.6004(8) 0.7564(7) 0.6745(5) 0.076(2) Uani 1 1 d . . .
H33 H 0.7034 0.7482 0.6800 0.091 Uiso 1 1 calc R . .
C34 C 0.4909(7) 0.7191(6) 0.6021(5) 0.063(2) Uani 1 1 d . . .
H34 H 0.5195 0.6876 0.5574 0.075 Uiso 1 1 calc R . .
C35 C 0.3353(7) 0.7285(5) 0.5951(4) 0.0487(15) Uani 1 1 d . . .
C36 C 0.2100(7) 0.6938(4) 0.5209(4) 0.0404(14) Uani 1 1 d . . .
C37 C 0.1413(7) 0.6170(4) 0.3767(4) 0.0436(15) Uani 1 1 d . . .
C38 C 0.1773(7) 0.5548(5) 0.3283(4) 0.0502(16) Uani 1 1 d . . .
H38 H 0.2755 0.5318 0.3502 0.060 Uiso 1 1 calc R . .
C39 C 0.0741(7) 0.5188(4) 0.2421(4) 0.0448(15) Uani 1 1 d . . .
C40 C 0.0372(11) 0.4320(5) 0.2361(6) 0.073(2) Uani 1 1 d . . .
H40 H 0.0818 0.3962 0.2867 0.087 Uiso 1 1 calc R . .
C41 C -0.0634(12) 0.3974(6) 0.1575(6) 0.097(3) Uani 1 1 d . . .
H41 H -0.0883 0.3391 0.1553 0.116 Uiso 1 1 calc R . .
C42 C -0.1265(10) 0.4491(7) 0.0829(6) 0.093(3) Uani 1 1 d . . .
H42 H -0.1965 0.4255 0.0302 0.111 Uiso 1 1 calc R . .
C43 C -0.0905(9) 0.5344(7) 0.0827(5) 0.073(2) Uani 1 1 d . . .
H43 H -0.1343 0.5686 0.0307 0.088 Uiso 1 1 calc R . .
C44 C 0.0129(7) 0.5692(5) 0.1620(4) 0.0522(16) Uani 1 1 d . . .
H44 H 0.0421 0.6267 0.1619 0.063 Uiso 1 1 calc R . .
C45 C -0.1266(6) 0.5853(4) 0.4682(4) 0.0444(15) Uani 1 1 d . . .
C46 C -0.2832(8) 0.5739(6) 0.4476(5) 0.069(2) Uani 1 1 d . . .
H46 H -0.3503 0.6165 0.4157 0.082 Uiso 1 1 calc R . .
C47 C -0.3396(8) 0.4983(6) 0.4750(6) 0.081(2) Uani 1 1 d . . .
H47 H -0.4449 0.4908 0.4614 0.097 Uiso 1 1 calc R . .
C48 C -0.2428(10) 0.4349(6) 0.5217(6) 0.076(2) Uani 1 1 d . . .
H48 H -0.2812 0.3846 0.5401 0.091 Uiso 1 1 calc R . .
C49 C -0.0850(9) 0.4469(6) 0.5414(5) 0.066(2) Uani 1 1 d . . .
H49 H -0.0172 0.4045 0.5729 0.079 Uiso 1 1 calc R . .
C50 C -0.0313(9) 0.5208(5) 0.5143(5) 0.0605(19) Uani 1 1 d . . .
H50 H 0.0739 0.5279 0.5275 0.073 Uiso 1 1 calc R . .
O1 O 0.6344(6) 0.5919(4) 0.2144(4) 0.0818(16) Uani 1 1 d . . .
O2 O 0.3988(6) 0.6041(4) 0.2016(5) 0.0878(18) Uani 1 1 d . . .
O3 O 0.2440(5) 0.7283(3) 0.0445(3) 0.0509(11) Uani 1 1 d . . .
O4 O 0.6012(6) 0.6053(4) -0.0922(3) 0.0712(16) Uani 1 1 d . . .
O5 O 0.3509(5) 0.5877(4) -0.1600(3) 0.0713(15) Uani 1 1 d . . .
N1 N 0.5153(6) 0.6307(4) 0.1902(3) 0.0488(13) Uani 1 1 d . . .
C1 C 0.5133(6) 0.7190(4) 0.1462(4) 0.0414(14) Uani 1 1 d . . .
H1 H 0.5873 0.7561 0.1905 0.050 Uiso 1 1 calc R . .
C2 C 0.5668(7) 0.7065(4) 0.0585(4) 0.0402(14) Uani 1 1 d . . .
H2 H 0.6495 0.6637 0.0735 0.048 Uiso 1 1 calc R . .
C3 C 0.4353(7) 0.6701(4) -0.0168(4) 0.0408(14) Uani 1 1 d . . .
C4 C 0.4720(8) 0.6214(5) -0.0890(4) 0.0543(17) Uani 1 1 d . . .
C5 C 0.2037(8) 0.6014(6) -0.1604(4) 0.0601(19) Uani 1 1 d . . .
C6 C 0.0885(9) 0.5598(8) -0.2342(5) 0.087(3) Uani 1 1 d . . .
H6 H 0.1140 0.5249 -0.2776 0.104 Uiso 1 1 calc R . .
C7 C -0.0594(10) 0.5735(9) -0.2378(6) 0.099(4) Uani 1 1 d . . .
H7 H -0.1354 0.5509 -0.2884 0.119 Uiso 1 1 calc R . .
C8 C -0.1039(8) 0.6179(7) -0.1727(5) 0.084(3) Uani 1 1 d . . .
H8 H -0.2067 0.6215 -0.1758 0.101 Uiso 1 1 calc R . .
C9 C 0.0088(7) 0.6578(6) -0.1013(4) 0.0584(19) Uani 1 1 d . . .
H9 H -0.0193 0.6917 -0.0581 0.070 Uiso 1 1 calc R . .
C10 C 0.1622(7) 0.6477(5) -0.0936(4) 0.0480(16) Uani 1 1 d . . .
C11 C 0.2886(7) 0.6828(4) -0.0196(4) 0.0447(15) Uani 1 1 d . . .
C12 C 0.3607(6) 0.7587(4) 0.1250(4) 0.0423(14) Uani 1 1 d . . .
C13 C 0.3205(7) 0.8229(4) 0.1721(4) 0.0469(15) Uani 1 1 d . . .
H13 H 0.2229 0.8463 0.1485 0.056 Uiso 1 1 calc R . .
C14 C 0.4244(7) 0.8588(5) 0.2607(4) 0.0466(16) Uani 1 1 d . . .
C15 C 0.4657(9) 0.9443(5) 0.2657(6) 0.068(2) Uani 1 1 d . . .
H15 H 0.4243 0.9812 0.2156 0.082 Uiso 1 1 calc R . .
C16 C 0.5718(9) 0.9748(5) 0.3481(6) 0.082(2) Uani 1 1 d . . .
H16 H 0.6007 1.0326 0.3518 0.099 Uiso 1 1 calc R . .
C17 C 0.6335(9) 0.9223(6) 0.4225(5) 0.067(2) Uani 1 1 d . . .
H17 H 0.7044 0.9434 0.4763 0.081 Uiso 1 1 calc R . .
C18 C 0.5883(8) 0.8375(5) 0.4160(5) 0.0579(18) Uani 1 1 d . . .
H18 H 0.6272 0.8010 0.4667 0.069 Uiso 1 1 calc R . .
C19 C 0.4865(7) 0.8057(5) 0.3358(4) 0.0545(16) Uani 1 1 d . . .
H19 H 0.4593 0.7477 0.3323 0.065 Uiso 1 1 calc R . .
C20 C 0.6299(6) 0.7907(4) 0.0312(4) 0.0416(14) Uani 1 1 d . . .
C21 C 0.5304(8) 0.8558(5) -0.0160(5) 0.0549(18) Uani 1 1 d . . .
H21 H 0.4249 0.8488 -0.0307 0.066 Uiso 1 1 calc R . .
C22 C 0.5921(10) 0.9318(5) -0.0409(6) 0.073(2) Uani 1 1 d . . .
H22 H 0.5263 0.9756 -0.0712 0.088 Uiso 1 1 calc R . .
C23 C 0.7428(11) 0.9426(6) -0.0220(5) 0.074(2) Uani 1 1 d . . .
H23 H 0.7807 0.9926 -0.0414 0.089 Uiso 1 1 calc R . .
C24 C 0.8412(10) 0.8809(7) 0.0256(6) 0.093(3) Uani 1 1 d . . .
H24 H 0.9464 0.8894 0.0408 0.112 Uiso 1 1 calc R . .
C25 C 0.7844(8) 0.8053(6) 0.0512(5) 0.062(2) Uani 1 1 d . . .
H25 H 0.8527 0.7632 0.0829 0.074 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
09 C29 1.189(7) . ?
06 N2 1.217(6) . ?
07 N2 1.230(7) . ?
08 C36 1.374(7) . ?
08 C37 1.381(7) . ?
010 C29 1.358(8) . ?
010 C30 1.392(7) . ?
N2 C26 1.536(8) . ?
C26 C37 1.508(8) . ?
C26 C27 1.531(8) . ?
C26 H26 0.9800 . ?
C27 C45 1.505(9) . ?
C27 C28 1.509(8) . ?
C27 H27 0.9800 . ?
C28 C36 1.342(8) . ?
C28 C29 1.447(8) . ?
C30 C31 1.323(10) . ?
C30 C35 1.401(9) . ?
C31 C32 1.380(11) . ?
C31 H31 0.9300 . ?
C32 C33 1.402(12) . ?
C32 H32 0.9300 . ?
C33 C34 1.366(10) . ?
C33 H33 0.9300 . ?
C34 C35 1.404(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.441(8) . ?
C37 C38 1.308(9) . ?
C38 C39 1.464(9) . ?
C38 H38 0.9300 . ?
C39 C40 1.383(11) . ?
C39 C44 1.403(9) . ?
C40 C41 1.369(12) . ?
C40 H40 0.9300 . ?
C41 C42 1.358(15) . ?
C41 H41 0.9300 . ?
C42 C43 1.361(15) . ?
C42 H42 0.9300 . ?
C43 C44 1.388(10) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 C50 1.369(10) . ?
C45 C46 1.384(8) . ?
C46 C47 1.392(11) . ?
C46 H46 0.9300 . ?
C47 C48 1.367(13) . ?
C47 H47 0.9300 . ?
C48 C49 1.397(10) . ?
C48 H48 0.9300 . ?
C49 C50 1.356(11) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
O1 N1 1.201(7) . ?
O2 N1 1.203(6) . ?
O3 C11 1.355(7) . ?
O3 C12 1.431(7) . ?
O4 C4 1.225(8) . ?
O5 C5 1.363(7) . ?
O5 C4 1.387(8) . ?
N1 C1 1.516(9) . ?
C1 C12 1.471(8) . ?
C1 C2 1.552(7) . ?
C1 H1 0.9800 . ?
C2 C3 1.492(8) . ?
C2 C20 1.532(9) . ?
C2 H2 0.9800 . ?
C3 C11 1.346(8) . ?
C3 C4 1.444(9) . ?
C5 C10 1.378(9) . ?
C5 C6 1.433(9) . ?
C6 C7 1.355(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.357(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.448(8) . ?
C12 C13 1.335(9) . ?
C13 C14 1.491(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(11) . ?
C14 C19 1.373(10) . ?
C15 C16 1.406(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.361(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.374(8) . ?
C20 C21 1.399(9) . ?
C21 C22 1.405(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.333(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(14) . ?
C23 H23 0.9300 . ?
C24 C25 1.381(12) . ?
C24 H24 0.9300 . ?
C25 H25 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
C36 08 C37 120.0(5) . . ?
C29 010 C30 123.5(5) . . ?
06 N2 07 123.9(6) . . ?
06 N2 C26 119.6(5) . . ?
07 N2 C26 116.5(5) . . ?
C37 C26 C27 112.3(5) . . ?
C37 C26 N2 111.0(5) . . ?
C27 C26 N2 109.0(5) . . ?
C37 C26 H26 108.2 . . ?
C27 C26 H26 108.2 . . ?
N2 C26 H26 108.1 . . ?
C45 C27 C28 112.7(5) . . ?
C45 C27 C26 111.9(5) . . ?
C28 C27 C26 107.8(5) . . ?
C45 C27 H27 108.0 . . ?
C28 C27 H27 108.0 . . ?
C26 C27 H27 108.2 . . ?
C36 C28 C29 119.7(5) . . ?
C36 C28 C27 122.1(5) . . ?
C29 C28 C27 118.2(5) . . ?
09 C29 010 117.5(6) . . ?
09 C29 C28 124.4(6) . . ?
010 C29 C28 118.0(5) . . ?
C31 C30 010 118.7(6) . . ?
C31 C30 C35 122.3(7) . . ?
010 C30 C35 119.0(6) . . ?
C30 C31 C32 121.4(7) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C31 C32 C33 117.9(7) . . ?
C31 C32 H32 120.9 . . ?
C33 C32 H32 121.2 . . ?
C34 C33 C32 121.0(7) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C33 C34 C35 120.0(7) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C30 C35 C34 117.2(6) . . ?
C30 C35 C36 117.8(6) . . ?
C34 C35 C36 124.9(6) . . ?
C28 C36 08 122.9(5) . . ?
C28 C36 C35 122.0(5) . . ?
08 C36 C35 115.1(5) . . ?
C38 C37 08 118.6(6) . . ?
C38 C37 C26 124.7(6) . . ?
08 C37 C26 116.7(5) . . ?
C37 C38 C39 124.7(6) . . ?
C37 C38 H38 117.7 . . ?
C39 C38 H38 117.6 . . ?
C40 C39 C44 117.3(6) . . ?
C40 C39 C38 120.5(6) . . ?
C44 C39 C38 122.2(6) . . ?
C41 C40 C39 121.6(8) . . ?
C41 C40 H40 119.1 . . ?
C39 C40 H40 119.3 . . ?
C42 C41 C40 119.4(8) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.4 . . ?
C41 C42 C43 122.0(8) . . ?
C41 C42 H42 118.9 . . ?
C43 C42 H42 119.0 . . ?
C42 C43 C44 118.6(8) . . ?
C42 C43 H43 120.6 . . ?
C44 C43 H43 120.8 . . ?
C43 C44 C39 120.9(7) . . ?
C43 C44 H44 119.6 . . ?
C39 C44 H44 119.5 . . ?
C50 C45 C46 118.6(7) . . ?
C50 C45 C27 122.8(6) . . ?
C46 C45 C27 118.6(6) . . ?
C45 C46 C47 119.6(8) . . ?
C45 C46 H46 120.1 . . ?
C47 C46 H46 120.3 . . ?
C48 C47 C46 121.0(7) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.3 . . ?
C47 C48 C49 118.8(8) . . ?
C47 C48 H48 120.4 . . ?
C49 C48 H48 120.7 . . ?
C50 C49 C48 119.7(8) . . ?
C50 C49 H49 120.2 . . ?
C48 C49 H49 120.1 . . ?
C49 C50 C45 122.3(7) . . ?
C49 C50 H50 118.9 . . ?
C45 C50 H50 118.8 . . ?
C11 O3 C12 117.7(4) . . ?
C5 O5 C4 120.3(5) . . ?
O1 N1 O2 123.3(6) . . ?
O1 N1 C1 118.2(5) . . ?
O2 N1 C1 118.4(6) . . ?
C12 C1 N1 110.9(5) . . ?
C12 C1 C2 113.0(4) . . ?
N1 C1 C2 107.1(5) . . ?
C12 C1 H1 108.5 . . ?
N1 C1 H1 108.7 . . ?
C2 C1 H1 108.6 . . ?
C3 C2 C20 113.7(5) . . ?
C3 C2 C1 107.6(5) . . ?
C20 C2 C1 111.3(5) . . ?
C3 C2 H2 108.1 . . ?
C20 C2 H2 108.0 . . ?
C1 C2 H2 107.9 . . ?
C11 C3 C4 120.6(5) . . ?
C11 C3 C2 122.5(5) . . ?
C4 C3 C2 116.9(5) . . ?
O4 C4 O5 116.8(6) . . ?
O4 C4 C3 125.6(6) . . ?
O5 C4 C3 117.5(6) . . ?
O5 C5 C10 124.7(6) . . ?
O5 C5 C6 115.4(6) . . ?
C10 C5 C6 119.8(6) . . ?
C7 C6 C5 117.0(8) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C6 C7 C8 124.4(7) . . ?
C6 C7 H7 118.0 . . ?
C8 C7 H7 117.6 . . ?
C7 C8 C9 117.9(7) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
C10 C9 C8 120.9(7) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.5 . . ?
C5 C10 C9 119.7(6) . . ?
C5 C10 C11 115.0(6) . . ?
C9 C10 C11 125.3(6) . . ?
C3 C11 O3 124.5(5) . . ?
C3 C11 C10 121.9(5) . . ?
O3 C11 C10 113.5(5) . . ?
C13 C12 O3 116.0(5) . . ?
C13 C12 C1 126.3(5) . . ?
O3 C12 C1 117.6(5) . . ?
C12 C13 C14 123.2(6) . . ?
C12 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C15 C14 C19 119.6(7) . . ?
C15 C14 C13 120.0(6) . . ?
C19 C14 C13 120.4(7) . . ?
C14 C15 C16 118.6(7) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 C15 121.9(8) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 118.2(7) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C19 121.0(7) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C18 120.7(7) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.6 . . ?
C25 C20 C21 117.5(7) . . ?
C25 C20 C2 121.9(6) . . ?
C21 C20 C2 120.6(5) . . ?
C20 C21 C22 119.1(7) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 121.5(8) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 120.1(8) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 119.8(8) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 120.3 . . ?
C20 C25 C24 121.9(8) . . ?
C20 C25 H25 119.1 . . ?
C24 C25 H25 118.9 . . ?

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
06 N2 C26 C37 -3.8(7) . . . . ?
07 N2 C26 C37 179.2(5) . . . . ?
06 N2 C26 C27 120.3(6) . . . . ?
07 N2 C26 C27 -56.7(7) . . . . ?
C37 C26 C27 C45 -78.2(6) . . . . ?
N2 C26 C27 C45 158.5(5) . . . . ?
C37 C26 C27 C28 46.4(7) . . . . ?
N2 C26 C27 C28 -77.0(6) . . . . ?
C45 C27 C28 C36 97.1(7) . . . . ?
C26 C27 C28 C36 -26.9(8) . . . . ?
C45 C27 C28 C29 -82.9(7) . . . . ?
C26 C27 C28 C29 153.0(6) . . . . ?
C30 010 C29 09 -179.8(7) . . . . ?
C30 010 C29 C28 2.1(11) . . . . ?
C36 C28 C29 09 -178.9(7) . . . . ?
C27 C28 C29 09 1.2(10) . . . . ?
C36 C28 C29 010 -1.0(10) . . . . ?
C27 C28 C29 010 179.1(6) . . . . ?
C29 010 C30 C31 178.7(8) . . . . ?
C29 010 C30 C35 -3.1(11) . . . . ?
010 C30 C31 C32 -178.9(9) . . . . ?
C35 C30 C31 C32 3.0(15) . . . . ?
C30 C31 C32 C33 -3.7(17) . . . . ?
C31 C32 C33 C34 3.4(16) . . . . ?
C32 C33 C34 C35 -2.4(14) . . . . ?
C31 C30 C35 C34 -1.8(11) . . . . ?
010 C30 C35 C34 -179.8(7) . . . . ?
C31 C30 C35 C36 -179.1(8) . . . . ?
010 C30 C35 C36 2.9(10) . . . . ?
C33 C34 C35 C30 1.5(11) . . . . ?
C33 C34 C35 C36 178.6(7) . . . . ?
C29 C28 C36 08 -179.3(6) . . . . ?
C27 C28 C36 08 0.6(9) . . . . ?
C29 C28 C36 C35 0.9(9) . . . . ?
C27 C28 C36 C35 -179.1(6) . . . . ?
C37 08 C36 C28 5.5(9) . . . . ?
C37 08 C36 C35 -174.7(6) . . . . ?
C30 C35 C36 C28 -1.9(9) . . . . ?
C34 C35 C36 C28 -178.9(7) . . . . ?
C30 C35 C36 08 178.3(6) . . . . ?
C34 C35 C36 08 1.3(10) . . . . ?
C36 08 C37 C38 -161.9(6) . . . . ?
C36 08 C37 C26 17.4(8) . . . . ?
C27 C26 C37 C38 134.7(6) . . . . ?
N2 C26 C37 C38 -103.1(7) . . . . ?
C27 C26 C37 08 -44.6(8) . . . . ?
N2 C26 C37 08 77.7(6) . . . . ?
08 C37 C38 C39 -177.4(6) . . . . ?
C26 C37 C38 C39 3.4(10) . . . . ?
C37 C38 C39 C40 -121.1(8) . . . . ?
C37 C38 C39 C44 61.1(9) . . . . ?
C44 C39 C40 C41 -4.5(12) . . . . ?
C38 C39 C40 C41 177.6(7) . . . . ?
C39 C40 C41 C42 1.3(14) . . . . ?
C40 C41 C42 C43 1.4(14) . . . . ?
C41 C42 C43 C44 -0.6(13) . . . . ?
C42 C43 C44 C39 -2.8(11) . . . . ?
C40 C39 C44 C43 5.3(10) . . . . ?
C38 C39 C44 C43 -176.8(6) . . . . ?
C28 C27 C45 C50 -44.2(8) . . . . ?
C26 C27 C45 C50 77.6(7) . . . . ?
C28 C27 C45 C46 134.6(6) . . . . ?
C26 C27 C45 C46 -103.7(7) . . . . ?
C50 C45 C46 C47 0.8(11) . . . . ?
C27 C45 C46 C47 -178.0(6) . . . . ?
C45 C46 C47 C48 -0.3(13) . . . . ?
C46 C47 C48 C49 -0.2(13) . . . . ?
C47 C48 C49 C50 0.2(12) . . . . ?
C48 C49 C50 C45 0.4(12) . . . . ?
C46 C45 C50 C49 -0.9(11) . . . . ?
C27 C45 C50 C49 177.9(6) . . . . ?
O1 N1 C1 C12 -177.4(5) . . . . ?
O2 N1 C1 C12 0.5(7) . . . . ?
O1 N1 C1 C2 58.9(7) . . . . ?
O2 N1 C1 C2 -123.2(6) . . . . ?
C12 C1 C2 C3 -45.0(7) . . . . ?
N1 C1 C2 C3 77.4(6) . . . . ?
C12 C1 C2 C20 80.2(6) . . . . ?
N1 C1 C2 C20 -157.4(5) . . . . ?
C20 C2 C3 C11 -97.8(7) . . . . ?
C1 C2 C3 C11 25.9(8) . . . . ?
C20 C2 C3 C4 80.8(7) . . . . ?
C1 C2 C3 C4 -155.4(6) . . . . ?
C5 O5 C4 O4 178.8(7) . . . . ?
C5 O5 C4 C3 0.4(11) . . . . ?
C11 C3 C4 O4 -179.0(7) . . . . ?
C2 C3 C4 O4 2.3(10) . . . . ?
C11 C3 C4 O5 -0.8(10) . . . . ?
C2 C3 C4 O5 -179.5(6) . . . . ?
C4 O5 C5 C10 -0.1(12) . . . . ?
C4 O5 C5 C6 -176.8(7) . . . . ?
O5 C5 C6 C7 -178.6(9) . . . . ?
C10 C5 C6 C7 4.4(14) . . . . ?
C5 C6 C7 C8 -5.4(18) . . . . ?
C6 C7 C8 C9 5.3(18) . . . . ?
C7 C8 C9 C10 -4.2(14) . . . . ?
O5 C5 C10 C9 179.7(8) . . . . ?
C6 C5 C10 C9 -3.7(12) . . . . ?
O5 C5 C10 C11 0.1(11) . . . . ?
C6 C5 C10 C11 176.7(7) . . . . ?
C8 C9 C10 C5 3.6(11) . . . . ?
C8 C9 C10 C11 -176.8(7) . . . . ?
C4 C3 C11 O3 -179.2(6) . . . . ?
C2 C3 C11 O3 -0.7(10) . . . . ?
C4 C3 C11 C10 0.9(10) . . . . ?
C2 C3 C11 C10 179.4(6) . . . . ?
C12 O3 C11 C3 -5.7(9) . . . . ?
C12 O3 C11 C10 174.3(6) . . . . ?
C5 C10 C11 C3 -0.5(10) . . . . ?
C9 C10 C11 C3 179.9(7) . . . . ?
C5 C10 C11 O3 179.6(6) . . . . ?
C9 C10 C11 O3 0.0(10) . . . . ?
C11 O3 C12 C13 161.1(6) . . . . ?
C11 O3 C12 C1 -17.0(8) . . . . ?
N1 C1 C12 C13 105.1(7) . . . . ?
C2 C1 C12 C13 -134.6(7) . . . . ?
N1 C1 C12 O3 -77.0(6) . . . . ?
C2 C1 C12 O3 43.2(8) . . . . ?
O3 C12 C13 C14 176.1(6) . . . . ?
C1 C12 C13 C14 -5.9(11) . . . . ?
C12 C13 C14 C15 119.6(8) . . . . ?
C12 C13 C14 C19 -56.6(9) . . . . ?
C19 C14 C15 C16 0.4(11) . . . . ?
C13 C14 C15 C16 -175.8(6) . . . . ?
C14 C15 C16 C17 -0.3(13) . . . . ?
C15 C16 C17 C18 -0.7(13) . . . . ?
C16 C17 C18 C19 1.6(12) . . . . ?
C15 C14 C19 C18 0.6(10) . . . . ?
C13 C14 C19 C18 176.7(6) . . . . ?
C17 C18 C19 C14 -1.6(10) . . . . ?
C3 C2 C20 C25 -135.8(7) . . . . ?
C1 C2 C20 C25 102.5(7) . . . . ?
C3 C2 C20 C21 43.8(8) . . . . ?
C1 C2 C20 C21 -78.0(7) . . . . ?
C25 C20 C21 C22 0.3(10) . . . . ?
C2 C20 C21 C22 -179.3(6) . . . . ?
C20 C21 C22 C23 1.2(12) . . . . ?
C21 C22 C23 C24 -2.6(13) . . . . ?
C22 C23 C24 C25 2.4(13) . . . . ?
C21 C20 C25 C24 -0.4(11) . . . . ?
C2 C20 C25 C24 179.2(7) . . . . ?
C23 C24 C25 C20 -1.0(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_ss053
_database_code_depnum_ccdc_archive 'CCDC 1437746'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 O3'
_chemical_formula_weight         368.41

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'
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   P2(1)/c

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                   9.2495(10)
_cell_length_b                   8.8594(7)
_cell_length_c                   26.022(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.322(12)
_cell_angle_gamma                90.00
_cell_volume                     1927.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4057
_cell_measurement_theta_min      3.3520
_cell_measurement_theta_max      28.4920

_exptl_crystal_description       NIDDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17000
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3391
_reflns_number_gt                2340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1401P)²+0.3737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3391
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.2580
_refine_ls_wR_factor_gt          0.2078
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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 0.8007(3) 0.3481(3) 0.23919(10) 0.0822(8) Uani 1 1 d . . .
O2 O 0.7473(3) 0.5563(3) 0.27394(10) 0.0793(7) Uani 1 1 d . . .
O3 O 0.8435(2) 0.8205(2) 0.16219(8) 0.0580(6) Uani 1 1 d . . .
C1 C 0.7871(4) 0.4837(4) 0.23472(13) 0.0648(8) Uani 1 1 d . . .
C2 C 0.8125(3) 0.5746(3) 0.19314(12) 0.0537(7) Uani 1 1 d . . .
C3 C 0.8434(3) 0.4918(3) 0.14763(12) 0.0562(7) Uani 1 1 d . . .
H3 H 0.9440 0.4359 0.1661 0.067 Uiso 1 1 calc R . .
C4 C 0.8615(4) 0.6090(3) 0.10650(13) 0.0594(8) Uani 1 1 d . . .
H4A H 0.9243 0.5651 0.0885 0.071 Uiso 1 1 calc R . .
H4B H 0.7566 0.6332 0.0769 0.071 Uiso 1 1 calc R . .
C5 C 0.9408(3) 0.7511(3) 0.13659(13) 0.0540(7) Uani 1 1 d . . .
H5 H 1.0463 0.7262 0.1667 0.065 Uiso 1 1 calc R . .
C6 C 0.8071(3) 0.7270(3) 0.19599(12) 0.0527(7) Uani 1 1 d . . .
C7 C 0.7572(3) 0.8022(4) 0.23534(12) 0.0544(7) Uani 1 1 d . . .
C8 C 0.7363(4) 0.9577(4) 0.23742(13) 0.0627(8) Uani 1 1 d . . .
H8 H 0.7571 1.0208 0.2128 0.075 Uiso 1 1 calc R . .
C9 C 0.6854(4) 1.0187(4) 0.27548(15) 0.0732(9) Uani 1 1 d . . .
H9 H 0.6696 1.1222 0.2761 0.088 Uiso 1 1 calc R . .
C10 C 0.6579(5) 0.9242(5) 0.31303(17) 0.0888(12) Uani 1 1 d . . .
H10 H 0.6245 0.9656 0.3390 0.107 Uiso 1 1 calc R . .
C11 C 0.6788(5) 0.7720(5) 0.31250(17) 0.0893(12) Uani 1 1 d . . .
H11 H 0.6609 0.7099 0.3380 0.107 Uiso 1 1 calc R . .
C12 C 0.7274(4) 0.7112(4) 0.27320(14) 0.0672(9) Uani 1 1 d . . .
C13 C 0.7102(3) 0.3803(3) 0.11597(12) 0.0527(7) Uani 1 1 d . . .
C14 C 0.7382(4) 0.2262(3) 0.11722(13) 0.0584(8) Uani 1 1 d . . .
H14 H 0.8415 0.1894 0.1373 0.070 Uiso 1 1 calc R . .
C15 C 0.6137(4) 0.1262(4) 0.08891(14) 0.0658(9) Uani 1 1 d . . .
H15 H 0.6343 0.0231 0.0905 0.079 Uiso 1 1 calc R . .
C16 C 0.4609(4) 0.1777(4) 0.05872(14) 0.0666(8) Uani 1 1 d . . .
H16 H 0.3782 0.1102 0.0395 0.080 Uiso 1 1 calc R . .
C17 C 0.4303(4) 0.3310(4) 0.05697(14) 0.0673(9) Uani 1 1 d . . .
H17 H 0.3266 0.3669 0.0369 0.081 Uiso 1 1 calc R . .
C18 C 0.5546(4) 0.4306(4) 0.08515(13) 0.0617(8) Uani 1 1 d . . .
H18 H 0.5333 0.5335 0.0834 0.074 Uiso 1 1 calc R . .
C19 C 0.9595(4) 0.8742(3) 0.09896(14) 0.0623(8) Uani 1 1 d . . .
H19A H 0.8563 0.8935 0.0675 0.075 Uiso 1 1 calc R . .
H19B H 0.9943 0.9665 0.1209 0.075 Uiso 1 1 calc R . .
C20 C 1.0780(3) 0.8325(3) 0.07565(13) 0.0559(7) Uani 1 1 d . . .
C21 C 1.0270(4) 0.7966(4) 0.01856(15) 0.0724(9) Uani 1 1 d . . .
H21 H 0.9183 0.7969 -0.0055 0.087 Uiso 1 1 calc R . .
C22 C 1.1361(5) 0.7606(4) -0.00291(17) 0.0839(11) Uani 1 1 d . . .
H22 H 1.1000 0.7353 -0.0411 0.101 Uiso 1 1 calc R . .
C23 C 1.2965(5) 0.7619(4) 0.03161(18) 0.0807(11) Uani 1 1 d . . .
H23 H 1.3697 0.7387 0.0170 0.097 Uiso 1 1 calc R . .
C24 C 1.3487(4) 0.7976(4) 0.08798(17) 0.0762(10) Uani 1 1 d . . .
H24 H 1.4577 0.7976 0.1117 0.091 Uiso 1 1 calc R . .
C25 C 1.2405(4) 0.8337(4) 0.11002(14) 0.0628(8) Uani 1 1 d . . .
H25 H 1.2777 0.8589 0.1482 0.075 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.208(4) . ?
O2 C12 1.383(4) . ?
O2 C1 1.383(4) . ?
O3 C6 1.352(3) . ?
O3 C5 1.465(3) . ?
C1 C2 1.446(4) . ?
C2 C6 1.354(4) . ?
C2 C3 1.520(4) . ?
C3 C13 1.518(4) . ?
C3 C4 1.551(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.498(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C19 1.524(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.452(4) . ?
C7 C12 1.389(4) . ?
C7 C8 1.395(5) . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(5) . ?
C11 H11 0.9300 . ?
C13 C14 1.387(4) . ?
C13 C18 1.388(4) . ?
C14 C15 1.388(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.508(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.382(4) . ?
C20 C21 1.390(4) . ?
C21 C22 1.383(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.367(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.387(4) . ?
C24 H24 0.9300 . ?
C25 H25 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
C12 O2 C1 121.8(2) . . ?
C6 O3 C5 114.3(2) . . ?
O1 C1 O2 116.2(3) . . ?
O1 C1 C2 125.6(3) . . ?
O2 C1 C2 118.2(3) . . ?
C6 C2 C1 119.5(3) . . ?
C6 C2 C3 123.2(3) . . ?
C1 C2 C3 117.3(3) . . ?
C13 C3 C2 111.0(2) . . ?
C13 C3 C4 111.3(2) . . ?
C2 C3 C4 109.0(2) . . ?
C13 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
C5 C4 C3 112.0(2) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O3 C5 C4 109.4(2) . . ?
O3 C5 C19 104.6(2) . . ?
C4 C5 C19 115.5(3) . . ?
O3 C5 H5 109.1 . . ?
C4 C5 H5 109.1 . . ?
C19 C5 H5 109.1 . . ?
O3 C6 C2 123.4(3) . . ?
O3 C6 C7 114.8(3) . . ?
C2 C6 C7 121.8(3) . . ?
C12 C7 C8 118.2(3) . . ?
C12 C7 C6 116.9(3) . . ?
C8 C7 C6 124.8(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 118.9(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
O2 C12 C7 121.4(3) . . ?
O2 C12 C11 117.2(3) . . ?
C7 C12 C11 121.4(3) . . ?
C14 C13 C18 117.8(3) . . ?
C14 C13 C3 121.9(3) . . ?
C18 C13 C3 120.3(3) . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 121.5(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C20 C19 C5 112.7(2) . . ?
C20 C19 H19A 109.1 . . ?
C5 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C5 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C25 C20 C21 118.1(3) . . ?
C25 C20 C19 121.0(3) . . ?
C21 C20 C19 120.9(3) . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 120.5(4) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.4(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 120.5(3) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?

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
C12 O2 C1 O1 -179.7(3) . . . . ?
C12 O2 C1 C2 1.7(4) . . . . ?
O1 C1 C2 C6 -174.2(3) . . . . ?
O2 C1 C2 C6 4.3(4) . . . . ?
O1 C1 C2 C3 6.2(5) . . . . ?
O2 C1 C2 C3 -175.4(3) . . . . ?
C6 C2 C3 C13 -124.5(3) . . . . ?
C1 C2 C3 C13 55.1(3) . . . . ?
C6 C2 C3 C4 -1.5(4) . . . . ?
C1 C2 C3 C4 178.1(2) . . . . ?
C13 C3 C4 C5 157.3(2) . . . . ?
C2 C3 C4 C5 34.5(3) . . . . ?
C6 O3 C5 C4 53.3(3) . . . . ?
C6 O3 C5 C19 177.6(2) . . . . ?
C3 C4 C5 O3 -60.9(3) . . . . ?
C3 C4 C5 C19 -178.5(2) . . . . ?
C5 O3 C6 C2 -20.3(4) . . . . ?
C5 O3 C6 C7 161.2(2) . . . . ?
C1 C2 C6 O3 173.8(3) . . . . ?
C3 C2 C6 O3 -6.5(4) . . . . ?
C1 C2 C6 C7 -7.7(4) . . . . ?
C3 C2 C6 C7 171.9(2) . . . . ?
O3 C6 C7 C12 -176.4(3) . . . . ?
C2 C6 C7 C12 5.0(4) . . . . ?
O3 C6 C7 C8 4.1(4) . . . . ?
C2 C6 C7 C8 -174.5(3) . . . . ?
C12 C7 C8 C9 -0.9(4) . . . . ?
C6 C7 C8 C9 178.6(3) . . . . ?
C7 C8 C9 C10 1.4(5) . . . . ?
C8 C9 C10 C11 -0.6(6) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C1 O2 C12 C7 -4.4(5) . . . . ?
C1 O2 C12 C11 176.5(3) . . . . ?
C8 C7 C12 O2 -179.3(3) . . . . ?
C6 C7 C12 O2 1.1(4) . . . . ?
C8 C7 C12 C11 -0.3(5) . . . . ?
C6 C7 C12 C11 -179.9(3) . . . . ?
C10 C11 C12 O2 -179.9(4) . . . . ?
C10 C11 C12 C7 1.0(6) . . . . ?
C2 C3 C13 C14 -117.2(3) . . . . ?
C4 C3 C13 C14 121.1(3) . . . . ?
C2 C3 C13 C18 61.9(3) . . . . ?
C4 C3 C13 C18 -59.7(3) . . . . ?
C18 C13 C14 C15 -0.6(4) . . . . ?
C3 C13 C14 C15 178.6(3) . . . . ?
C13 C14 C15 C16 0.6(5) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C16 C17 C18 C13 -0.8(5) . . . . ?
C14 C13 C18 C17 0.7(4) . . . . ?
C3 C13 C18 C17 -178.5(3) . . . . ?
O3 C5 C19 C20 171.1(2) . . . . ?
C4 C5 C19 C20 -68.6(4) . . . . ?
C5 C19 C20 C25 -74.0(4) . . . . ?
C5 C19 C20 C21 108.1(3) . . . . ?
C25 C20 C21 C22 1.1(5) . . . . ?
C19 C20 C21 C22 179.1(3) . . . . ?
C20 C21 C22 C23 -1.0(6) . . . . ?
C21 C22 C23 C24 0.7(6) . . . . ?
C22 C23 C24 C25 -0.6(6) . . . . ?
C21 C20 C25 C24 -1.0(5) . . . . ?
C19 C20 C25 C24 -179.0(3) . . . . ?
C23 C24 C25 C20 0.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.110
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1437747'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 F N O4'
_chemical_formula_weight         379.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.3205(3)
_cell_length_b                   26.2500(10)
_cell_length_c                   8.5535(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.859(4)
_cell_angle_gamma                90
_cell_volume                     1834.74(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5843
_cell_measurement_theta_min      3.8960
_cell_measurement_theta_max      30.7720

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_T_min  0.50860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            14087
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.104
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3218
_reflns_number_gt                2623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1331P)²+0.4890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3218
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.2293
_refine_ls_wR_factor_gt          0.1934
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5843(3) 0.64122(8) 0.0221(2) 0.0725(6) Uani 1 1 d . . . . .
O1 O -0.1096(3) 0.28386(10) 0.1561(3) 0.0790(8) Uani 1 1 d . . . . .
O2 O 0.1341(2) 0.44324(7) 0.10148(19) 0.0458(5) Uani 1 1 d . . . . .
O3 O -0.1825(3) 0.41837(10) 0.4213(4) 0.0889(9) Uani 1 1 d . . . . .
O4 O -0.1179(3) 0.48590(10) 0.3135(3) 0.0717(7) Uani 1 1 d . . . . .
C1 C -0.0709(4) 0.31715(11) 0.0713(3) 0.0485(7) Uani 1 1 d . . . . .
C2 C -0.1227(5) 0.31521(13) -0.1064(4) 0.0645(9) Uani 1 1 d . . . . .
H2A H -0.1280 0.2799 -0.1404 0.077 Uiso 1 1 calc R U . . .
H2B H -0.2318 0.3295 -0.1356 0.077 Uiso 1 1 calc R U . . .
C3 C -0.0114(5) 0.34319(14) -0.1917(4) 0.0684(9) Uani 1 1 d . . . . .
H3A H -0.0593 0.3441 -0.3042 0.082 Uiso 1 1 calc R U . . .
H3B H 0.0913 0.3248 -0.1800 0.082 Uiso 1 1 calc R U . . .
C4 C 0.0232(4) 0.39761(11) -0.1320(3) 0.0462(7) Uani 1 1 d . . . . .
H4A H 0.1164 0.4110 -0.1719 0.055 Uiso 1 1 calc R U . . .
H4B H -0.0707 0.4190 -0.1717 0.055 Uiso 1 1 calc R U . . .
C5 C 0.0583(3) 0.39867(9) 0.0458(3) 0.0368(6) Uani 1 1 d . . . . .
C6 C 0.1725(3) 0.45293(9) 0.2642(3) 0.0385(6) Uani 1 1 d . . . . .
C7 C 0.0866(3) 0.42125(10) 0.3679(3) 0.0385(6) Uani 1 1 d . . . . .
H7 H 0.1484 0.4234 0.4772 0.046 Uiso 1 1 calc R U . . .
C8 C 0.0695(3) 0.36478(9) 0.3205(3) 0.0362(6) Uani 1 1 d . . . . .
H8 H -0.0204 0.3504 0.3657 0.043 Uiso 1 1 calc R U . . .
C9 C 0.0224(3) 0.36172(9) 0.1414(3) 0.0363(6) Uani 1 1 d . . . . .
C10 C 0.2243(3) 0.33478(9) 0.3869(3) 0.0386(6) Uani 1 1 d . . . . .
C11 C 0.2143(4) 0.29484(11) 0.4917(3) 0.0535(7) Uani 1 1 d . . . . .
H11 H 0.1146 0.2869 0.5196 0.064 Uiso 1 1 calc R U . . .
C12 C 0.3529(5) 0.26690(13) 0.5545(4) 0.0730(10) Uani 1 1 d . . . . .
H12 H 0.3455 0.2405 0.6253 0.088 Uiso 1 1 calc R U . . .
C13 C 0.5009(5) 0.27780(14) 0.5133(5) 0.0739(11) Uani 1 1 d . . . . .
H13 H 0.5934 0.2590 0.5560 0.089 Uiso 1 1 calc R U . . .
C14 C 0.5111(4) 0.31687(13) 0.4080(4) 0.0645(9) Uani 1 1 d . . . . .
H14 H 0.6108 0.3243 0.3789 0.077 Uiso 1 1 calc R U . . .
C15 C 0.3736(3) 0.34511(11) 0.3454(3) 0.0472(7) Uani 1 1 d . . . . .
H15 H 0.3818 0.3714 0.2744 0.057 Uiso 1 1 calc R U . . .
C16 C 0.2737(3) 0.49091(9) 0.3184(3) 0.0389(6) Uani 1 1 d . . . . .
H16 H 0.2949 0.4946 0.4285 0.047 Uiso 1 1 calc R U . . .
C17 C 0.3574(3) 0.52803(9) 0.2331(3) 0.0377(6) Uani 1 1 d . . . . .
C18 C 0.4535(3) 0.56487(10) 0.3239(3) 0.0440(6) Uani 1 1 d . . . . .
H18 H 0.4657 0.5638 0.4342 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5313(3) 0.60304(11) 0.2545(4) 0.0500(7) Uani 1 1 d . . . . .
H19 H 0.5951 0.6274 0.3162 0.060 Uiso 1 1 calc R U . . .
C20 C 0.5111(3) 0.60357(11) 0.0918(4) 0.0473(7) Uani 1 1 d . . . . .
C21 C 0.4171(3) 0.56857(11) -0.0037(3) 0.0493(7) Uani 1 1 d . . . . .
H21 H 0.4053 0.5703 -0.1139 0.059 Uiso 1 1 calc R U . . .
C22 C 0.3402(3) 0.53059(11) 0.0673(3) 0.0458(7) Uani 1 1 d . . . . .
H22 H 0.2763 0.5065 0.0041 0.055 Uiso 1 1 calc R U . . .
N1 N -0.0865(3) 0.44353(9) 0.3652(3) 0.0468(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C20 1.356(3) . ?
O1 C1 1.217(4) . ?
O2 C5 1.372(3) . ?
O2 C6 1.392(3) . ?
O3 N1 1.204(3) . ?
O4 N1 1.207(3) . ?
C1 C9 1.468(4) . ?
C1 C2 1.501(4) . ?
C2 C3 1.478(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.526(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.494(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C9 1.338(4) . ?
C6 C16 1.330(4) . ?
C6 C7 1.492(3) . ?
C7 C8 1.536(3) . ?
C7 N1 1.551(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.511(3) . ?
C8 C10 1.525(4) . ?
C8 H8 0.9800 . ?
C10 C15 1.382(4) . ?
C10 C11 1.392(4) . ?
C11 C12 1.386(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.469(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.394(4) . ?
C17 C22 1.400(4) . ?
C18 C19 1.386(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(4) . ?
C21 C22 1.385(4) . ?
C21 H21 0.9300 . ?
C22 H22 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
C5 O2 C6 120.47(19) . . ?
O1 C1 C9 120.5(3) . . ?
O1 C1 C2 121.4(3) . . ?
C9 C1 C2 118.0(2) . . ?
C3 C2 C1 113.3(3) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 113.3(3) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 110.3(2) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C9 C5 O2 123.2(2) . . ?
C9 C5 C4 125.8(2) . . ?
O2 C5 C4 111.0(2) . . ?
C16 C6 O2 119.7(2) . . ?
C16 C6 C7 123.6(2) . . ?
O2 C6 C7 116.6(2) . . ?
C6 C7 C8 114.3(2) . . ?
C6 C7 N1 109.2(2) . . ?
C8 C7 N1 108.7(2) . . ?
C6 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
N1 C7 H7 108.2 . . ?
C9 C8 C10 112.93(19) . . ?
C9 C8 C7 108.19(19) . . ?
C10 C8 C7 111.7(2) . . ?
C9 C8 H8 107.9 . . ?
C10 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
C5 C9 C1 119.4(2) . . ?
C5 C9 C8 122.4(2) . . ?
C1 C9 C8 118.2(2) . . ?
C15 C10 C11 118.6(3) . . ?
C15 C10 C8 122.7(2) . . ?
C11 C10 C8 118.7(2) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.9(3) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C6 C16 C17 130.7(2) . . ?
C6 C16 H16 114.7 . . ?
C17 C16 H16 114.7 . . ?
C18 C17 C22 118.0(2) . . ?
C18 C17 C16 117.3(2) . . ?
C22 C17 C16 124.6(2) . . ?
C19 C18 C17 121.9(2) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C20 C19 C18 117.7(3) . . ?
C20 C19 H19 121.2 . . ?
C18 C19 H19 121.2 . . ?
F1 C20 C19 118.3(3) . . ?
F1 C20 C21 118.6(3) . . ?
C19 C20 C21 123.0(3) . . ?
C20 C21 C22 118.7(3) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C21 C22 C17 120.7(2) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
O3 N1 O4 122.5(3) . . ?
O3 N1 C7 118.1(2) . . ?
O4 N1 C7 119.3(2) . . ?

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
O1 C1 C2 C3 -154.2(3) . . . . ?
C9 C1 C2 C3 28.5(4) . . . . ?
C1 C2 C3 C4 -51.3(4) . . . . ?
C2 C3 C4 C5 44.9(4) . . . . ?
C6 O2 C5 C9 -2.5(4) . . . . ?
C6 O2 C5 C4 177.6(2) . . . . ?
C3 C4 C5 C9 -17.2(4) . . . . ?
C3 C4 C5 O2 162.7(3) . . . . ?
C5 O2 C6 C16 166.7(2) . . . . ?
C5 O2 C6 C7 -17.2(3) . . . . ?
C16 C6 C7 C8 -143.2(2) . . . . ?
O2 C6 C7 C8 40.8(3) . . . . ?
C16 C6 C7 N1 94.8(3) . . . . ?
O2 C6 C7 N1 -81.1(3) . . . . ?
C6 C7 C8 C9 -42.3(3) . . . . ?
N1 C7 C8 C9 79.9(2) . . . . ?
C6 C7 C8 C10 82.6(3) . . . . ?
N1 C7 C8 C10 -155.17(19) . . . . ?
O2 C5 C9 C1 175.0(2) . . . . ?
C4 C5 C9 C1 -5.1(4) . . . . ?
O2 C5 C9 C8 -2.9(4) . . . . ?
C4 C5 C9 C8 177.0(2) . . . . ?
O1 C1 C9 C5 -177.6(3) . . . . ?
C2 C1 C9 C5 -0.2(4) . . . . ?
O1 C1 C9 C8 0.4(4) . . . . ?
C2 C1 C9 C8 177.8(2) . . . . ?
C10 C8 C9 C5 -99.1(3) . . . . ?
C7 C8 C9 C5 25.1(3) . . . . ?
C10 C8 C9 C1 83.0(3) . . . . ?
C7 C8 C9 C1 -152.8(2) . . . . ?
C9 C8 C10 C15 60.0(3) . . . . ?
C7 C8 C10 C15 -62.2(3) . . . . ?
C9 C8 C10 C11 -118.9(3) . . . . ?
C7 C8 C10 C11 118.9(2) . . . . ?
C15 C10 C11 C12 1.2(4) . . . . ?
C8 C10 C11 C12 -179.8(3) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C11 C10 C15 C14 -0.9(4) . . . . ?
C8 C10 C15 C14 -179.8(2) . . . . ?
C13 C14 C15 C10 0.0(5) . . . . ?
O2 C6 C16 C17 1.2(4) . . . . ?
C7 C6 C16 C17 -174.7(2) . . . . ?
C6 C16 C17 C18 178.1(3) . . . . ?
C6 C16 C17 C22 1.8(4) . . . . ?
C22 C17 C18 C19 -0.3(4) . . . . ?
C16 C17 C18 C19 -176.9(2) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 F1 178.9(3) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
F1 C20 C21 C22 -179.0(3) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C17 0.2(4) . . . . ?
C18 C17 C22 C21 0.3(4) . . . . ?
C16 C17 C22 C21 176.6(2) . . . . ?
C6 C7 N1 O3 168.3(3) . . . . ?
C8 C7 N1 O3 43.0(3) . . . . ?
C6 C7 N1 O4 -14.7(3) . . . . ?
C8 C7 N1 O4 -140.0(3) . . . . ?

_refine_diff_density_max         0.618
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.173

