# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_spiro
_audit_block_doi                 10.5517/cc13888x
_database_code_depnum_ccdc_archive 'CCDC 1020838'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetlet.2014.12.088 2015
_audit_update_record             
;
2014-08-24 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        quinoline
_chemical_name_common            'quinoline fused isoxazole'
_chemical_melting_point          340
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 F N5 O3'
_chemical_formula_weight         417.40

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

_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                   13.3119(5)
_cell_length_b                   10.7033(4)
_cell_length_c                   13.8141(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.8261(12)
_cell_angle_gamma                90
_cell_volume                     1967.25(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5199
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.91

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14836
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.408
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3469
_reflns_number_gt                2750
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.6326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3469
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C -0.10316(13) 0.1159(2) -0.20037(13) 0.0452(5) Uani 1 1 d . . . . .
H1 H -0.1357 0.0488 -0.2304 0.054 Uiso 1 1 calc R U . . .
C2 C -0.14066(14) 0.2325(2) -0.21218(14) 0.0511(5) Uani 1 1 d . . . . .
H2 H -0.1983 0.2460 -0.2506 0.061 Uiso 1 1 calc R U . . .
C3 C -0.09197(13) 0.33208(19) -0.16613(13) 0.0444(5) Uani 1 1 d . . . . .
C4 C -0.00656(12) 0.32005(17) -0.11190(12) 0.0375(4) Uani 1 1 d . . . . .
H4 H 0.0237 0.3895 -0.0829 0.045 Uiso 1 1 calc R U . . .
C5 C 0.03628(12) 0.19960(15) -0.09985(10) 0.0293(4) Uani 1 1 d . . . . .
C6 C 0.12816(11) 0.18127(15) -0.04617(10) 0.0272(4) Uani 1 1 d . . . . .
C7 C 0.16130(11) 0.05869(15) -0.04051(10) 0.0285(4) Uani 1 1 d . . . . .
C8 C 0.24750(12) -0.00742(16) -0.00028(11) 0.0333(4) Uani 1 1 d . . . . .
C9 C 0.10120(12) -0.03622(15) -0.08104(11) 0.0318(4) Uani 1 1 d . . . . .
C10 C -0.01481(12) 0.09508(17) -0.14267(11) 0.0335(4) Uani 1 1 d . . . . .
C11 C 0.18646(11) 0.28469(14) -0.00099(10) 0.0272(3) Uani 1 1 d . . . . .
C12 C 0.23094(12) 0.37396(15) -0.06155(10) 0.0295(4) Uani 1 1 d . . . . .
C13 C 0.32453(12) 0.45638(16) 0.08015(11) 0.0352(4) Uani 1 1 d . . . . .
C14 C 0.20714(11) 0.28592(15) 0.09843(10) 0.0277(4) Uani 1 1 d . . . . .
C15 C 0.34124(17) 0.5588(2) -0.07414(14) 0.0565(6) Uani 1 1 d . . . . .
H15A H 0.3279 0.6388 -0.0458 0.085 Uiso 1 1 calc R U . . .
H15B H 0.3131 0.5563 -0.1390 0.085 Uiso 1 1 calc R U . . .
H15C H 0.4125 0.5458 -0.0756 0.085 Uiso 1 1 calc R U . . .
C16 C 0.30415(15) 0.36752(19) 0.23971(11) 0.0471(5) Uani 1 1 d . . . . .
H16A H 0.2450 0.3844 0.2755 0.071 Uiso 1 1 calc R U . . .
H16B H 0.3535 0.4311 0.2532 0.071 Uiso 1 1 calc R U . . .
H16C H 0.3310 0.2876 0.2585 0.071 Uiso 1 1 calc R U . . .
C17 C 0.33985(12) 0.04275(17) 0.04787(12) 0.0367(4) Uani 1 1 d . . . . .
C18 C 0.39704(13) 0.13002(18) 0.00045(14) 0.0454(5) Uani 1 1 d . . . . .
H18 H 0.3769 0.1565 -0.0613 0.054 Uiso 1 1 calc R U . . .
C19 C 0.48320(15) 0.1782(2) 0.04341(17) 0.0609(6) Uani 1 1 d . . . . .
H19 H 0.5218 0.2355 0.0102 0.073 Uiso 1 1 calc R U . . .
C20 C 0.51207(16) 0.1418(3) 0.13481(18) 0.0718(7) Uani 1 1 d . . . . .
H20 H 0.5696 0.1756 0.1643 0.086 Uiso 1 1 calc R U . . .
C21 C 0.45675(17) 0.0559(3) 0.18301(16) 0.0757(8) Uani 1 1 d . . . . .
H21 H 0.4768 0.0315 0.2453 0.091 Uiso 1 1 calc R U . . .
C22 C 0.37062(15) 0.0047(2) 0.13950(14) 0.0594(6) Uani 1 1 d . . . . .
H22 H 0.3338 -0.0550 0.1721 0.071 Uiso 1 1 calc R U . . .
N1 N 0.23825(11) -0.12774(14) -0.01345(11) 0.0444(4) Uani 1 1 d . . . . .
N2 N 0.29572(11) 0.46038(13) -0.01620(9) 0.0351(3) Uani 1 1 d . . . . .
N3 N 0.27816(10) 0.36672(13) 0.13604(9) 0.0308(3) Uani 1 1 d . . . . .
N4 N 0.16085(11) 0.21113(14) 0.15960(10) 0.0362(4) Uani 1 1 d . . . . .
N5 N 0.01627(10) -0.02614(13) -0.13010(9) 0.0359(3) Uani 1 1 d . . . . .
O2 O 0.14449(9) -0.14949(11) -0.06414(9) 0.0441(3) Uani 1 1 d . . . . .
O3 O 0.21766(9) 0.38003(11) -0.15062(7) 0.0399(3) Uani 1 1 d . . . . .
O4 O 0.38625(10) 0.52817(13) 0.11492(9) 0.0548(4) Uani 1 1 d . . . . .
F1 F -0.13321(9) 0.44750(12) -0.17755(9) 0.0666(4) Uani 1 1 d . . . . .
H1N H 0.1808(13) 0.2028(17) 0.2196(14) 0.043(5) Uiso 1 1 d . . . . .
H2N H 0.1085(15) 0.1637(19) 0.1380(14) 0.051(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.352(3) . ?
C1 C10 1.417(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.391(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.348(2) . ?
C3 F1 1.359(2) . ?
C4 C5 1.417(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.424(2) . ?
C5 C10 1.428(2) . ?
C6 C7 1.386(2) . ?
C6 C11 1.479(2) . ?
C7 C9 1.399(2) . ?
C7 C8 1.444(2) . ?
C8 N1 1.306(2) . ?
C8 C17 1.480(2) . ?
C9 N5 1.304(2) . ?
C9 O2 1.359(2) . ?
C10 N5 1.371(2) . ?
C11 C14 1.392(2) . ?
C11 C12 1.413(2) . ?
C12 O3 1.2392(17) . ?
C12 N2 1.399(2) . ?
C13 O4 1.213(2) . ?
C13 N2 1.374(2) . ?
C13 N3 1.389(2) . ?
C14 N4 1.330(2) . ?
C14 N3 1.3713(19) . ?
C15 N2 1.466(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N3 1.4626(19) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.379(2) . ?
C17 C18 1.383(3) . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 O2 1.4306(18) . ?
N4 H1N 0.867(19) . ?
N4 H2N 0.90(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 120.66(17) . . ?
C2 C1 H1 119.7 . . ?
C10 C1 H1 119.7 . . ?
C1 C2 C3 119.15(16) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 F1 118.81(18) . . ?
C4 C3 C2 123.63(18) . . ?
F1 C3 C2 117.56(16) . . ?
C3 C4 C5 118.77(17) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.49(15) . . ?
C4 C5 C10 118.66(14) . . ?
C6 C5 C10 119.85(15) . . ?
C7 C6 C5 115.25(14) . . ?
C7 C6 C11 121.55(13) . . ?
C5 C6 C11 123.19(14) . . ?
C6 C7 C9 119.21(14) . . ?
C6 C7 C8 137.16(14) . . ?
C9 C7 C8 103.62(14) . . ?
N1 C8 C7 111.06(15) . . ?
N1 C8 C17 119.59(15) . . ?
C7 C8 C17 129.32(15) . . ?
N5 C9 O2 121.25(14) . . ?
N5 C9 C7 128.56(16) . . ?
O2 C9 C7 110.18(14) . . ?
N5 C10 C1 117.51(15) . . ?
N5 C10 C5 123.45(14) . . ?
C1 C10 C5 119.03(16) . . ?
C14 C11 C12 120.30(14) . . ?
C14 C11 C6 120.54(13) . . ?
C12 C11 C6 118.73(13) . . ?
O3 C12 N2 118.45(14) . . ?
O3 C12 C11 125.06(14) . . ?
N2 C12 C11 116.49(13) . . ?
O4 C13 N2 121.91(15) . . ?
O4 C13 N3 121.68(14) . . ?
N2 C13 N3 116.41(13) . . ?
N4 C14 N3 117.83(13) . . ?
N4 C14 C11 122.70(14) . . ?
N3 C14 C11 119.47(14) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 118.82(17) . . ?
C22 C17 C8 121.57(17) . . ?
C18 C17 C8 119.61(15) . . ?
C19 C18 C17 120.87(19) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.8(2) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C8 N1 O2 107.79(13) . . ?
C13 N2 C12 124.21(13) . . ?
C13 N2 C15 116.35(14) . . ?
C12 N2 C15 119.36(13) . . ?
C14 N3 C13 122.58(12) . . ?
C14 N3 C16 120.89(13) . . ?
C13 N3 C16 116.41(13) . . ?
C14 N4 H1N 122.4(12) . . ?
C14 N4 H2N 119.7(12) . . ?
H1N N4 H2N 117.8(17) . . ?
C9 N5 C10 113.40(14) . . ?
C9 O2 N1 107.30(12) . . ?

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
C10 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C1 C2 C3 F1 -178.33(17) . . . . ?
F1 C3 C4 C5 179.86(15) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 177.86(15) . . . . ?
C3 C4 C5 C10 -2.3(2) . . . . ?
C4 C5 C6 C7 -179.87(14) . . . . ?
C10 C5 C6 C7 0.3(2) . . . . ?
C4 C5 C6 C11 -1.2(2) . . . . ?
C10 C5 C6 C11 178.97(13) . . . . ?
C5 C6 C7 C9 -4.0(2) . . . . ?
C11 C6 C7 C9 177.35(13) . . . . ?
C5 C6 C7 C8 177.01(17) . . . . ?
C11 C6 C7 C8 -1.7(3) . . . . ?
C6 C7 C8 N1 177.73(17) . . . . ?
C9 C7 C8 N1 -1.40(18) . . . . ?
C6 C7 C8 C17 -4.3(3) . . . . ?
C9 C7 C8 C17 176.54(16) . . . . ?
C6 C7 C9 N5 3.8(2) . . . . ?
C8 C7 C9 N5 -176.89(16) . . . . ?
C6 C7 C9 O2 -177.24(13) . . . . ?
C8 C7 C9 O2 2.08(16) . . . . ?
C2 C1 C10 N5 176.95(16) . . . . ?
C2 C1 C10 C5 -2.2(3) . . . . ?
C4 C5 C10 N5 -175.45(15) . . . . ?
C6 C5 C10 N5 4.4(2) . . . . ?
C4 C5 C10 C1 3.7(2) . . . . ?
C6 C5 C10 C1 -176.49(14) . . . . ?
C7 C6 C11 C14 -60.2(2) . . . . ?
C5 C6 C11 C14 121.26(16) . . . . ?
C7 C6 C11 C12 112.32(17) . . . . ?
C5 C6 C11 C12 -66.3(2) . . . . ?
C14 C11 C12 O3 179.59(15) . . . . ?
C6 C11 C12 O3 7.1(2) . . . . ?
C14 C11 C12 N2 0.4(2) . . . . ?
C6 C11 C12 N2 -172.07(14) . . . . ?
C12 C11 C14 N4 174.09(15) . . . . ?
C6 C11 C14 N4 -13.6(2) . . . . ?
C12 C11 C14 N3 -6.1(2) . . . . ?
C6 C11 C14 N3 166.25(14) . . . . ?
N1 C8 C17 C22 -57.5(2) . . . . ?
C7 C8 C17 C22 124.7(2) . . . . ?
N1 C8 C17 C18 122.57(19) . . . . ?
C7 C8 C17 C18 -55.2(2) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
C8 C17 C18 C19 -179.98(17) . . . . ?
C17 C18 C19 C20 -1.3(3) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C18 C17 C22 C21 1.2(3) . . . . ?
C8 C17 C22 C21 -178.73(19) . . . . ?
C20 C21 C22 C17 -1.3(4) . . . . ?
C7 C8 N1 O2 0.22(18) . . . . ?
C17 C8 N1 O2 -177.95(13) . . . . ?
O4 C13 N2 C12 174.81(17) . . . . ?
N3 C13 N2 C12 -6.0(2) . . . . ?
O4 C13 N2 C15 -1.9(3) . . . . ?
N3 C13 N2 C15 177.25(16) . . . . ?
O3 C12 N2 C13 -173.36(15) . . . . ?
C11 C12 N2 C13 5.9(2) . . . . ?
O3 C12 N2 C15 3.3(2) . . . . ?
C11 C12 N2 C15 -177.51(16) . . . . ?
N4 C14 N3 C13 -174.12(15) . . . . ?
C11 C14 N3 C13 6.1(2) . . . . ?
N4 C14 N3 C16 1.9(2) . . . . ?
C11 C14 N3 C16 -177.93(15) . . . . ?
O4 C13 N3 C14 179.02(16) . . . . ?
N2 C13 N3 C14 -0.1(2) . . . . ?
O4 C13 N3 C16 2.8(2) . . . . ?
N2 C13 N3 C16 -176.32(15) . . . . ?
O2 C9 N5 C10 -178.14(14) . . . . ?
C7 C9 N5 C10 0.7(2) . . . . ?
C1 C10 N5 C9 176.10(14) . . . . ?
C5 C10 N5 C9 -4.8(2) . . . . ?
N5 C9 O2 N1 177.03(14) . . . . ?
C7 C9 O2 N1 -2.02(17) . . . . ?
C8 N1 O2 C9 1.10(17) . . . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMSO-D6, DMF'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1035535'
_audit_update_record             
;
2014-11-22 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        spiro
_chemical_name_common            ?
_chemical_melting_point          254-256
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H22 N4 O4.50 S0.50'
_chemical_formula_weight         526.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   24.9048(6)
_cell_length_b                   9.4980(2)
_cell_length_c                   22.2694(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.7230(10)
_cell_angle_gamma                90
_cell_volume                     4926.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    12338
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      28.43

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             2192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7418
_exptl_absorpt_correction_T_max  0.8451
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker smart apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46298
_diffrn_reflns_av_unetI/netI     0.1589
_diffrn_reflns_av_R_equivalents  0.1036
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.748
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12338
_reflns_number_gt                4043
_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       'APEXII (Bruker, 2004)'
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-97 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0909P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         12338
_refine_ls_number_parameters     846
_refine_ls_number_restraints     284
_refine_ls_R_factor_all          0.2374
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.1511
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      1.013
_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
C1 C 0.98261(16) 0.3326(4) 0.32909(19) 0.0509(10) Uani 1 1 d . . . . .
C2 C 0.99866(18) 0.4674(4) 0.3519(2) 0.0638(12) Uani 1 1 d . . . . .
H2 H 1.0212 0.4816 0.3947 0.077 Uiso 1 1 calc R U . . .
C3 C 0.9808(2) 0.5820(4) 0.3102(2) 0.0724(13) Uani 1 1 d . . . . .
H3 H 0.9909 0.6730 0.3254 0.087 Uiso 1 1 calc R U . . .
C4 C 0.94861(19) 0.5603(5) 0.2471(2) 0.0681(12) Uani 1 1 d . . . . .
H4 H 0.9368 0.6368 0.2195 0.082 Uiso 1 1 calc R U . . .
C5 C 0.93357(17) 0.4272(5) 0.2240(2) 0.0654(12) Uani 1 1 d . . . . .
H5 H 0.9122 0.4139 0.1808 0.079 Uiso 1 1 calc R U . . .
C6 C 0.94973(16) 0.3123(4) 0.26444(19) 0.0563(11) Uani 1 1 d . . . . .
H6 H 0.9388 0.2220 0.2487 0.068 Uiso 1 1 calc R U . . .
C7 C 1.00638(16) 0.2112(4) 0.37223(17) 0.0463(9) Uani 1 1 d . . . . .
C8 C 0.98027(14) 0.0875(4) 0.38608(16) 0.0382(8) Uani 1 1 d . . . . .
C9 C 1.02609(15) 0.0157(4) 0.42516(17) 0.0425(9) Uani 1 1 d . . . . .
C10 C 0.97337(15) -0.1717(4) 0.43881(16) 0.0404(9) Uani 1 1 d . . . . .
C11 C 0.92580(18) -0.3798(4) 0.45779(19) 0.0529(10) Uani 1 1 d . . . . .
C12 C 0.87076(17) -0.1754(4) 0.39897(18) 0.0482(10) Uani 1 1 d . . . . .
C13 C 0.92351(15) -0.1074(3) 0.40369(16) 0.0395(9) Uani 1 1 d . . . . .
C14 C 0.92025(13) 0.0328(3) 0.36832(16) 0.0376(9) Uani 1 1 d . . . . .
C15 C 0.88768(15) 0.0187(3) 0.29684(17) 0.0405(9) Uani 1 1 d . . . . .
C16 C 0.89960(16) -0.0609(4) 0.25141(18) 0.0490(10) Uani 1 1 d . . . . .
H16 H 0.9326 -0.1160 0.2629 0.059 Uiso 1 1 calc R U . . .
C17 C 0.86192(18) -0.0580(4) 0.18851(19) 0.0602(11) Uani 1 1 d . . . . .
H17 H 0.8694 -0.1116 0.1574 0.072 Uiso 1 1 calc R U . . .
C18 C 0.81321(18) 0.0247(5) 0.1721(2) 0.0656(12) Uani 1 1 d . . . . .
H18 H 0.7880 0.0257 0.1297 0.079 Uiso 1 1 calc R U . . .
C19 C 0.80119(16) 0.1061(4) 0.21726(18) 0.0565(11) Uani 1 1 d . . . . .
H19 H 0.7684 0.1617 0.2058 0.068 Uiso 1 1 calc R U . . .
C20 C 0.83915(14) 0.1026(4) 0.27974(18) 0.0438(9) Uani 1 1 d . . . . .
C21 C 0.83732(12) 0.1776(3) 0.33328(14) 0.0226(7) Uani 1 1 d . . . . .
C22 C 0.88063(15) 0.1385(3) 0.3861(2) 0.0440(9) Uani 1 1 d . . . . .
C23 C 0.78918(15) 0.2626(4) 0.33480(19) 0.0539(10) Uani 1 1 d . . . . .
H23A H 0.7940 0.2806 0.3793 0.065 Uiso 1 1 calc R U . . .
H23B H 0.7542 0.2083 0.3161 0.065 Uiso 1 1 calc R U . . .
C24 C 0.78165(16) 0.4022(4) 0.30011(19) 0.0482(10) Uani 1 1 d D . . . .
C25 C 0.8245(7) 0.476(2) 0.2926(10) 0.081(5) Uani 0.66(2) 1 d D U P A 1
H25 H 0.8616 0.4397 0.3100 0.098 Uiso 0.66(2) 1 calc R U P A 1
C26 C 0.8163(6) 0.6041(19) 0.2599(8) 0.087(4) Uani 0.66(2) 1 d D U P A 1
H26 H 0.8476 0.6481 0.2544 0.105 Uiso 0.66(2) 1 calc R U P A 1
C27 C 0.7647(6) 0.665(2) 0.2365(9) 0.085(4) Uani 0.66(2) 1 d D U P A 1
H27 H 0.7599 0.7546 0.2183 0.101 Uiso 0.66(2) 1 calc R U P A 1
C28 C 0.7175(4) 0.5864(11) 0.2407(8) 0.089(4) Uani 0.66(2) 1 d D U P A 1
H28 H 0.6802 0.6205 0.2221 0.107 Uiso 0.66(2) 1 calc R U P A 1
C29 C 0.7273(3) 0.4605(11) 0.2722(7) 0.081(3) Uani 0.66(2) 1 d D U P A 1
H29 H 0.6961 0.4112 0.2752 0.097 Uiso 0.66(2) 1 calc R U P A 1
C25' C 0.8178(13) 0.456(4) 0.274(2) 0.080(9) Uani 0.34(2) 1 d D U P A 2
H25' H 0.8519 0.4092 0.2786 0.096 Uiso 0.34(2) 1 calc R U P A 2
C26' C 0.8042(15) 0.582(4) 0.2392(18) 0.099(8) Uani 0.34(2) 1 d D U P A 2
H26' H 0.8284 0.6216 0.2202 0.118 Uiso 0.34(2) 1 calc R U P A 2
C27' C 0.7543(17) 0.642(4) 0.235(2) 0.102(8) Uani 0.34(2) 1 d D U P A 2
H27' H 0.7357 0.7014 0.2006 0.122 Uiso 0.34(2) 1 calc R U P A 2
C28' C 0.7296(13) 0.615(2) 0.2824(19) 0.116(7) Uani 0.34(2) 1 d D U P A 2
H28' H 0.7086 0.6826 0.2949 0.139 Uiso 0.34(2) 1 calc R U P A 2
C29' C 0.7385(11) 0.483(2) 0.3086(17) 0.098(8) Uani 0.34(2) 1 d D U P A 2
H29' H 0.7165 0.4492 0.3315 0.117 Uiso 0.34(2) 1 calc R U P A 2
C30 C 0.30242(17) 0.1698(4) -0.0276(2) 0.0576(11) Uani 1 1 d . . . . .
C31 C 0.24777(18) 0.2247(4) -0.0400(2) 0.0623(11) Uani 1 1 d . . . . .
H31 H 0.2373 0.3086 -0.0627 0.075 Uiso 1 1 calc R U . . .
C32 C 0.20864(18) 0.1548(5) -0.0187(2) 0.0705(13) Uani 1 1 d . . . . .
H32 H 0.1722 0.1924 -0.0270 0.085 Uiso 1 1 calc R U . . .
C33 C 0.2238(2) 0.0307(5) 0.0145(2) 0.0785(14) Uani 1 1 d . . . . .
H33 H 0.1976 -0.0154 0.0288 0.094 Uiso 1 1 calc R U . . .
C34 C 0.2772(2) -0.0256(5) 0.0267(3) 0.0922(16) Uani 1 1 d . . . . .
H34 H 0.2870 -0.1105 0.0487 0.111 Uiso 1 1 calc R U . . .
C35 C 0.3168(2) 0.0439(5) 0.0062(2) 0.0794(14) Uani 1 1 d . . . . .
H35 H 0.3532 0.0059 0.0153 0.095 Uiso 1 1 calc R U . . .
C36 C 0.34292(17) 0.2317(4) -0.0547(2) 0.0562(11) Uani 1 1 d . . . . .
C37 C 0.36992(15) 0.3666(4) -0.04711(18) 0.0483(10) Uani 1 1 d . . . . .
C38 C 0.40334(17) 0.3564(4) -0.0824(2) 0.0541(10) Uani 1 1 d . . . . .
C39 C 0.44345(15) 0.5754(4) -0.05574(18) 0.0481(10) Uani 1 1 d . . . . .
C40 C 0.48917(17) 0.8027(4) -0.0356(2) 0.0544(10) Uani 1 1 d . . . . .
C41 C 0.42231(16) 0.7305(4) 0.0176(2) 0.0484(10) Uani 1 1 d . . . . .
C42 C 0.41279(15) 0.6004(4) -0.01713(17) 0.0452(9) Uani 1 1 d . . . . .
C43 C 0.36822(14) 0.4981(4) -0.00959(17) 0.0445(9) Uani 1 1 d . . . . .
C44 C 0.30787(15) 0.5572(4) -0.02835(19) 0.0490(10) Uani 1 1 d . . . . .
C45 C 0.27211(17) 0.6126(4) -0.0849(2) 0.0629(11) Uani 1 1 d . . . . .
H45 H 0.2845 0.6262 -0.1193 0.075 Uiso 1 1 calc R U . . .
C46 C 0.21676(18) 0.6481(5) -0.0897(2) 0.0727(13) Uani 1 1 d . . . . .
H46 H 0.1918 0.6855 -0.1280 0.087 Uiso 1 1 calc R U . . .
C47 C 0.19773(18) 0.6295(5) -0.0395(2) 0.0716(13) Uani 1 1 d . . . . .
H47 H 0.1606 0.6564 -0.0441 0.086 Uiso 1 1 calc R U . . .
C48 C 0.23292(17) 0.5716(4) 0.0177(2) 0.0596(11) Uani 1 1 d . . . . .
H48 H 0.2201 0.5570 0.0516 0.072 Uiso 1 1 calc R U . . .
C49 C 0.28842(16) 0.5359(4) 0.02247(19) 0.0517(10) Uani 1 1 d . . . . .
C50 C 0.33125(13) 0.4712(3) 0.07390(15) 0.0306(8) Uani 1 1 d . . . . .
C51 C 0.37973(18) 0.4555(4) 0.06111(19) 0.0513(10) Uani 1 1 d . . . . .
C52 C 0.32387(17) 0.4198(4) 0.13149(19) 0.0647(12) Uani 1 1 d D . . . .
H52A H 0.3490 0.3395 0.1472 0.078 Uiso 1 1 calc R U . B 1
H52B H 0.2847 0.3870 0.1205 0.078 Uiso 1 1 calc R U . B 1
C53 C 0.3358(9) 0.524(2) 0.1839(7) 0.060(5) Uani 0.39(4) 1 d DG U P C 1
C54 C 0.3181(11) 0.4806(15) 0.2335(11) 0.072(4) Uani 0.39(4) 1 d G U P C 1
H54 H 0.2941 0.4027 0.2280 0.087 Uiso 0.39(4) 1 calc R U P C 1
C55 C 0.3361(10) 0.554(2) 0.2914(7) 0.083(5) Uani 0.39(4) 1 d G U P C 1
H55 H 0.3242 0.5245 0.3246 0.100 Uiso 0.39(4) 1 calc R U P C 1
C56 C 0.3718(7) 0.670(3) 0.2996(7) 0.085(6) Uani 0.39(4) 1 d G U P C 1
H56 H 0.3839 0.7187 0.3383 0.102 Uiso 0.39(4) 1 calc R U P C 1
C57 C 0.3896(8) 0.713(3) 0.2499(12) 0.081(5) Uani 0.39(4) 1 d G U P C 1
H57 H 0.4135 0.7911 0.2554 0.097 Uiso 0.39(4) 1 calc R U P C 1
C58 C 0.3716(9) 0.640(2) 0.1921(8) 0.071(5) Uani 0.39(4) 1 d G U P C 1
H58 H 0.3834 0.6693 0.1589 0.085 Uiso 0.39(4) 1 calc R U P C 1
C53' C 0.3435(6) 0.5213(11) 0.1881(5) 0.058(3) Uani 0.61(4) 1 d DG U P C 2
C54' C 0.3386(9) 0.4889(9) 0.2468(6) 0.074(4) Uani 0.61(4) 1 d G U P C 2
H54' H 0.3249 0.4011 0.2532 0.089 Uiso 0.61(4) 1 calc R U P C 2
C55' C 0.3543(8) 0.5875(15) 0.2961(4) 0.089(4) Uani 0.61(4) 1 d G U P C 2
H55' H 0.3510 0.5658 0.3354 0.106 Uiso 0.61(4) 1 calc R U P C 2
C56' C 0.3747(5) 0.7187(17) 0.2867(6) 0.102(4) Uani 0.61(4) 1 d G U P C 2
H56A H 0.3852 0.7847 0.3196 0.123 Uiso 0.61(4) 1 calc R U P C 2
C57' C 0.3796(7) 0.7512(14) 0.2279(9) 0.095(4) Uani 0.61(4) 1 d G U P C 2
H57' H 0.3933 0.8389 0.2216 0.114 Uiso 0.61(4) 1 calc R U P C 2
C58' C 0.3639(7) 0.6525(13) 0.1787(6) 0.077(4) Uani 0.61(4) 1 d G U P C 2
H58' H 0.3672 0.6742 0.1394 0.092 Uiso 0.61(4) 1 calc R U P C 2
N1 N 1.06267(14) 0.2137(3) 0.40214(16) 0.0583(9) Uani 1 1 d . . . . .
N2 N 1.02663(13) -0.1156(3) 0.45083(15) 0.0486(8) Uani 1 1 d D . . . .
N3 N 0.97442(14) -0.3024(3) 0.46617(15) 0.0471(8) Uani 1 1 d D . . . .
N4 N 0.87634(15) -0.3108(3) 0.42500(16) 0.0563(9) Uani 1 1 d D . . . .
N5 N 0.35900(16) 0.1498(4) -0.09296(19) 0.0762(11) Uani 1 1 d . . . . .
N6 N 0.44111(14) 0.4523(4) -0.08963(18) 0.0570(9) Uani 1 1 d D . . . .
N7 N 0.48117(14) 0.6722(3) -0.06356(16) 0.0519(8) Uani 1 1 d D . . . .
N8 N 0.45861(14) 0.8262(4) 0.00315(17) 0.0557(9) Uani 1 1 d D . . . .
O1 O 1.07607(10) 0.0827(3) 0.43747(12) 0.0538(7) Uani 1 1 d . . . . .
O2 O 0.92737(12) -0.4995(3) 0.47870(14) 0.0684(8) Uani 1 1 d . . . . .
O3 O 0.82288(11) -0.1232(3) 0.37438(13) 0.0617(8) Uani 1 1 d . . . . .
O4 O 0.88763(10) 0.1825(2) 0.44072(12) 0.0506(7) Uani 1 1 d . . . . .
O5 O 0.39918(12) 0.2311(3) -0.11149(14) 0.0736(9) Uani 1 1 d . . . . .
O6 O 0.52192(12) 0.8882(3) -0.04522(14) 0.0689(8) Uani 1 1 d . . . . .
O7 O 0.39991(11) 0.7611(3) 0.05710(14) 0.0624(8) Uani 1 1 d . . . . .
O8 O 0.42502(11) 0.4063(3) 0.09896(13) 0.0586(7) Uani 1 1 d . . . . .
S1 S 0.42870(12) 0.3498(3) -0.25790(12) 0.0877(12) Uani 0.603(5) 1 d D U P D 1
O9 O 0.4557(10) 0.459(2) -0.2043(7) 0.107(5) Uani 0.603(5) 1 d D U P D 1
C59 C 0.4771(9) 0.2017(13) -0.2251(10) 0.154(7) Uani 0.603(5) 1 d D U P D 1
H59A H 0.5130 0.2362 -0.1957 0.231 Uiso 0.603(5) 1 calc R U P D 1
H59B H 0.4836 0.1519 -0.2594 0.231 Uiso 0.603(5) 1 calc R U P D 1
H59C H 0.4601 0.1393 -0.2029 0.231 Uiso 0.603(5) 1 calc R U P D 1
C60 C 0.4597(6) 0.3944(19) -0.3179(6) 0.153(6) Uani 0.603(5) 1 d D U P D 1
H60A H 0.4617 0.4950 -0.3210 0.230 Uiso 0.603(5) 1 calc R U P D 1
H60B H 0.4361 0.3567 -0.3587 0.230 Uiso 0.603(5) 1 calc R U P D 1
H60C H 0.4976 0.3553 -0.3058 0.230 Uiso 0.603(5) 1 calc R U P D 1
S1' S 0.4766(3) 0.4012(6) -0.2461(3) 0.134(2) Uani 0.397(5) 1 d D U P D 2
O9' O 0.4419(15) 0.471(3) -0.2085(11) 0.095(6) Uani 0.397(5) 1 d D U P D 2
C59' C 0.4568(12) 0.2180(15) -0.2383(13) 0.127(7) Uani 0.397(5) 1 d D U P D 2
H59D H 0.4185 0.2150 -0.2375 0.190 Uiso 0.397(5) 1 calc R U P D 2
H59E H 0.4830 0.1789 -0.1992 0.190 Uiso 0.397(5) 1 calc R U P D 2
H59F H 0.4584 0.1643 -0.2741 0.190 Uiso 0.397(5) 1 calc R U P D 2
C60' C 0.4246(8) 0.421(2) -0.3276(6) 0.132(7) Uani 0.397(5) 1 d D U P D 2
H60D H 0.3879 0.3865 -0.3291 0.198 Uiso 0.397(5) 1 calc R U P D 2
H60E H 0.4372 0.3672 -0.3568 0.198 Uiso 0.397(5) 1 calc R U P D 2
H60F H 0.4215 0.5181 -0.3396 0.198 Uiso 0.397(5) 1 calc R U P D 2
H2A H 1.0591(12) -0.142(4) 0.4847(14) 0.082(14) Uiso 1 1 d D . . . .
H8 H 0.4621(16) 0.921(5) 0.0173(19) 0.078(14) Uiso 1 1 d . . . . .
H3A H 1.0075(10) -0.343(3) 0.4846(15) 0.046(11) Uiso 1 1 d D . . . .
H7 H 0.5074(13) 0.643(4) -0.0786(18) 0.077(14) Uiso 1 1 d D . . . .
H6A H 0.442(2) 0.463(6) -0.1292(13) 0.13(2) Uiso 1 1 d D . . . .
H4A H 0.8439(11) -0.352(4) 0.4211(19) 0.074(14) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(5) . ?
C1 C6 1.395(5) . ?
C1 C7 1.484(5) . ?
C2 C3 1.398(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.322(4) . ?
C7 C8 1.429(5) . ?
C8 C9 1.350(4) . ?
C8 C14 1.498(4) . ?
C9 O1 1.337(4) . ?
C9 N2 1.370(4) . ?
C10 C13 1.356(4) . ?
C10 N2 1.365(4) . ?
C10 N3 1.379(4) . ?
C11 O2 1.224(4) . ?
C11 N4 1.358(5) . ?
C11 N3 1.371(5) . ?
C12 O3 1.227(4) . ?
C12 N4 1.397(5) . ?
C12 C13 1.434(5) . ?
C13 C14 1.534(5) . ?
C14 C15 1.515(5) . ?
C14 C22 1.555(5) . ?
C15 C16 1.377(5) . ?
C15 C20 1.384(4) . ?
C16 C17 1.383(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.403(4) . ?
C21 C22 1.337(4) . ?
C21 C23 1.456(4) . ?
C22 O4 1.238(4) . ?
C23 C24 1.512(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.335(8) . ?
C24 C25' 1.335(10) . ?
C24 C29' 1.388(9) . ?
C24 C29 1.388(7) . ?
C25 C26 1.398(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.337(9) . ?
C26 H26 0.9300 . ?
C27 C28 1.425(14) . ?
C27 H27 0.9300 . ?
C28 C29 1.365(9) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C25' C26' 1.402(10) . ?
C25' H25' 0.9300 . ?
C26' C27' 1.339(11) . ?
C26' H26' 0.9300 . ?
C27' C28' 1.425(16) . ?
C27' H27' 0.9300 . ?
C28' C29' 1.362(11) . ?
C28' H28' 0.9300 . ?
C29' H29' 0.9300 . ?
C30 C31 1.391(5) . ?
C30 C35 1.391(5) . ?
C30 C36 1.470(5) . ?
C31 C32 1.393(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.371(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.370(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.390(6) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 N5 1.316(5) . ?
C36 C37 1.429(5) . ?
C37 C38 1.335(5) . ?
C37 C43 1.512(5) . ?
C38 O5 1.341(4) . ?
C38 N6 1.359(5) . ?
C39 C42 1.357(5) . ?
C39 N7 1.369(5) . ?
C39 N6 1.382(5) . ?
C40 O6 1.222(4) . ?
C40 N8 1.356(5) . ?
C40 N7 1.369(5) . ?
C41 O7 1.232(4) . ?
C41 N8 1.398(5) . ?
C41 C42 1.432(5) . ?
C42 C43 1.528(5) . ?
C43 C44 1.518(5) . ?
C43 C51 1.551(5) . ?
C44 C45 1.366(5) . ?
C44 C49 1.395(5) . ?
C45 C46 1.386(5) . ?
C45 H45 0.9300 . ?
C46 C47 1.371(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.379(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.390(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.401(5) . ?
C50 C51 1.343(5) . ?
C50 C52 1.444(5) . ?
C51 O8 1.236(4) . ?
C52 C53 1.477(8) . ?
C52 C53' 1.524(7) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C53 C54 1.3900 . ?
C53 C58 1.3900 . ?
C54 C55 1.3900 . ?
C54 H54 0.9300 . ?
C55 C56 1.3900 . ?
C55 H55 0.9300 . ?
C56 C57 1.3900 . ?
C56 H56 0.9300 . ?
C57 C58 1.3900 . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
C53' C54' 1.3900 . ?
C53' C58' 1.3900 . ?
C54' C55' 1.3900 . ?
C54' H54' 0.9300 . ?
C55' C56' 1.3900 . ?
C55' H55' 0.9300 . ?
C56' C57' 1.3900 . ?
C56' H56A 0.9300 . ?
C57' C58' 1.3900 . ?
C57' H57' 0.9300 . ?
C58' H58' 0.9300 . ?
N1 O1 1.446(4) . ?
N2 H2A 0.923(18) . ?
N3 H3A 0.869(18) . ?
N4 H4A 0.872(18) . ?
N5 O5 1.435(4) . ?
N6 H6A 0.894(19) . ?
N7 H7 0.878(19) . ?
N8 H8 0.95(4) . ?
S1 O9 1.547(16) . ?
S1 C60 1.814(10) . ?
S1 C59 1.828(12) . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
S1' O9' 1.552(16) . ?
S1' C60' 1.828(12) . ?
S1' C59' 1.833(14) . ?
C59' H59D 0.9600 . ?
C59' H59E 0.9600 . ?
C59' H59F 0.9600 . ?
C60' H60D 0.9600 . ?
C60' H60E 0.9600 . ?
C60' H60F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.7(4) . . ?
C2 C1 C7 119.0(4) . . ?
C6 C1 C7 120.9(3) . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 112.8(3) . . ?
N1 C7 C1 114.9(3) . . ?
C8 C7 C1 132.2(3) . . ?
C9 C8 C7 102.1(3) . . ?
C9 C8 C14 122.2(3) . . ?
C7 C8 C14 135.8(3) . . ?
O1 C9 C8 113.9(3) . . ?
O1 C9 N2 118.5(3) . . ?
C8 C9 N2 127.6(3) . . ?
C13 C10 N2 124.4(3) . . ?
C13 C10 N3 122.0(3) . . ?
N2 C10 N3 113.5(3) . . ?
O2 C11 N4 123.6(4) . . ?
O2 C11 N3 122.6(4) . . ?
N4 C11 N3 113.8(4) . . ?
O3 C12 N4 119.7(3) . . ?
O3 C12 C13 124.8(3) . . ?
N4 C12 C13 115.5(3) . . ?
C10 C13 C12 117.9(3) . . ?
C10 C13 C14 123.9(3) . . ?
C12 C13 C14 118.2(3) . . ?
C8 C14 C15 114.9(3) . . ?
C8 C14 C13 107.4(3) . . ?
C15 C14 C13 112.0(3) . . ?
C8 C14 C22 111.9(3) . . ?
C15 C14 C22 100.0(3) . . ?
C13 C14 C22 110.6(3) . . ?
C16 C15 C20 120.6(3) . . ?
C16 C15 C14 130.2(3) . . ?
C20 C15 C14 109.2(3) . . ?
C15 C16 C17 119.2(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 121.4(4) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 118.2(4) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 H19 120.9 . . ?
C19 C20 C15 120.8(4) . . ?
C19 C20 C21 128.9(3) . . ?
C15 C20 C21 110.2(3) . . ?
C22 C21 C20 110.4(3) . . ?
C22 C21 C23 123.2(3) . . ?
C20 C21 C23 125.2(3) . . ?
O4 C22 C21 124.1(3) . . ?
O4 C22 C14 126.0(3) . . ?
C21 C22 C14 110.0(3) . . ?
C21 C23 C24 115.4(3) . . ?
C21 C23 H23A 108.4 . . ?
C24 C23 H23A 108.4 . . ?
C21 C23 H23B 108.4 . . ?
C24 C23 H23B 108.4 . . ?
H23A C23 H23B 107.5 . . ?
C25' C24 C29' 122(2) . . ?
C25 C24 C29 115.6(11) . . ?
C25 C24 C23 124.2(10) . . ?
C25' C24 C23 125.1(18) . . ?
C29' C24 C23 112.3(9) . . ?
C29 C24 C23 120.2(5) . . ?
C24 C25 C26 123.0(16) . . ?
C24 C25 H25 118.5 . . ?
C26 C25 H25 118.5 . . ?
C27 C26 C25 121.7(16) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C28 116.7(14) . . ?
C26 C27 H27 121.7 . . ?
C28 C27 H27 121.7 . . ?
C29 C28 C27 119.5(10) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C28 C29 C24 123.3(8) . . ?
C28 C29 H29 118.4 . . ?
C24 C29 H29 118.4 . . ?
C24 C25' C26' 120(3) . . ?
C24 C25' H25' 120.1 . . ?
C26' C25' H25' 120.1 . . ?
C27' C26' C25' 116(4) . . ?
C27' C26' H26' 121.9 . . ?
C25' C26' H26' 121.9 . . ?
C26' C27' C28' 120(3) . . ?
C26' C27' H27' 119.9 . . ?
C28' C27' H27' 119.9 . . ?
C29' C28' C27' 116(2) . . ?
C29' C28' H28' 122.1 . . ?
C27' C28' H28' 122.1 . . ?
C28' C29' C24 117.9(16) . . ?
C28' C29' H29' 121.0 . . ?
C24 C29' H29' 121.0 . . ?
C31 C30 C35 118.4(4) . . ?
C31 C30 C36 122.3(4) . . ?
C35 C30 C36 118.9(4) . . ?
C30 C31 C32 120.5(4) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C33 C32 C31 120.1(4) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.3(4) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.1(5) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C34 C35 C30 120.6(4) . . ?
C34 C35 H35 119.7 . . ?
C30 C35 H35 119.7 . . ?
N5 C36 C37 111.6(4) . . ?
N5 C36 C30 116.1(4) . . ?
C37 C36 C30 132.3(4) . . ?
C38 C37 C36 103.3(3) . . ?
C38 C37 C43 122.1(3) . . ?
C36 C37 C43 134.6(4) . . ?
C37 C38 O5 113.0(4) . . ?
C37 C38 N6 128.5(4) . . ?
O5 C38 N6 118.4(4) . . ?
C42 C39 N7 121.9(3) . . ?
C42 C39 N6 124.7(4) . . ?
N7 C39 N6 113.4(3) . . ?
O6 C40 N8 124.2(4) . . ?
O6 C40 N7 121.3(4) . . ?
N8 C40 N7 114.5(4) . . ?
O7 C41 N8 120.3(4) . . ?
O7 C41 C42 124.0(3) . . ?
N8 C41 C42 115.7(4) . . ?
C39 C42 C41 118.0(3) . . ?
C39 C42 C43 123.5(3) . . ?
C41 C42 C43 118.5(3) . . ?
C37 C43 C44 111.8(3) . . ?
C37 C43 C42 107.5(3) . . ?
C44 C43 C42 115.0(3) . . ?
C37 C43 C51 108.3(3) . . ?
C44 C43 C51 100.7(3) . . ?
C42 C43 C51 113.4(3) . . ?
C45 C44 C49 120.3(4) . . ?
C45 C44 C43 131.0(4) . . ?
C49 C44 C43 108.5(3) . . ?
C44 C45 C46 118.1(4) . . ?
C44 C45 H45 121.0 . . ?
C46 C45 H45 121.0 . . ?
C47 C46 C45 121.9(4) . . ?
C47 C46 H46 119.1 . . ?
C45 C46 H46 119.1 . . ?
C46 C47 C48 120.9(4) . . ?
C46 C47 H47 119.6 . . ?
C48 C47 H47 119.6 . . ?
C47 C48 C49 117.3(4) . . ?
C47 C48 H48 121.4 . . ?
C49 C48 H48 121.4 . . ?
C48 C49 C44 121.6(4) . . ?
C48 C49 C50 128.2(4) . . ?
C44 C49 C50 110.1(3) . . ?
C51 C50 C49 110.9(3) . . ?
C51 C50 C52 123.9(3) . . ?
C49 C50 C52 125.1(3) . . ?
O8 C51 C50 124.7(4) . . ?
O8 C51 C43 125.9(4) . . ?
C50 C51 C43 109.2(3) . . ?
C50 C52 C53 115.0(9) . . ?
C50 C52 C53' 114.7(6) . . ?
C50 C52 H52A 108.5 . . ?
C53 C52 H52A 108.5 . . ?
C50 C52 H52B 108.5 . . ?
C53 C52 H52B 108.5 . . ?
H52A C52 H52B 107.5 . . ?
C54 C53 C58 120.0 . . ?
C54 C53 C52 113.4(15) . . ?
C58 C53 C52 125.2(14) . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C54 C55 C56 120.0 . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C57 C56 C55 120.0 . . ?
C57 C56 H56 120.0 . . ?
C55 C56 H56 120.0 . . ?
C56 C57 C58 120.0 . . ?
C56 C57 H57 120.0 . . ?
C58 C57 H57 120.0 . . ?
C57 C58 C53 120.0 . . ?
C57 C58 H58 120.0 . . ?
C53 C58 H58 120.0 . . ?
C54' C53' C58' 120.0 . . ?
C54' C53' C52 122.0(8) . . ?
C58' C53' C52 118.0(8) . . ?
C53' C54' C55' 120.0 . . ?
C53' C54' H54' 120.0 . . ?
C55' C54' H54' 120.0 . . ?
C56' C55' C54' 120.0 . . ?
C56' C55' H55' 120.0 . . ?
C54' C55' H55' 120.0 . . ?
C57' C56' C55' 120.0 . . ?
C57' C56' H56A 120.0 . . ?
C55' C56' H56A 120.0 . . ?
C56' C57' C58' 120.0 . . ?
C56' C57' H57' 120.0 . . ?
C58' C57' H57' 120.0 . . ?
C57' C58' C53' 120.0 . . ?
C57' C58' H58' 120.0 . . ?
C53' C58' H58' 120.0 . . ?
C7 N1 O1 105.0(3) . . ?
C10 N2 C9 114.1(3) . . ?
C10 N2 H2A 124(3) . . ?
C9 N2 H2A 117(3) . . ?
C11 N3 C10 123.0(3) . . ?
C11 N3 H3A 118(2) . . ?
C10 N3 H3A 118(2) . . ?
C11 N4 C12 127.3(4) . . ?
C11 N4 H4A 118(3) . . ?
C12 N4 H4A 115(3) . . ?
C36 N5 O5 105.7(3) . . ?
C38 N6 C39 113.5(3) . . ?
C38 N6 H6A 117(4) . . ?
C39 N6 H6A 115(4) . . ?
C39 N7 C40 123.1(4) . . ?
C39 N7 H7 118(3) . . ?
C40 N7 H7 117(3) . . ?
C40 N8 C41 126.4(4) . . ?
C40 N8 H8 111(3) . . ?
C41 N8 H8 122(3) . . ?
C9 O1 N1 106.2(3) . . ?
C38 O5 N5 106.3(3) . . ?
O9 S1 C60 103.2(10) . . ?
O9 S1 C59 99.4(10) . . ?
C60 S1 C59 94.7(7) . . ?
S1 C59 H59A 109.5 . . ?
S1 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
S1 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
S1 C60 H60A 109.5 . . ?
S1 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
S1 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
O9' S1' C60' 99.1(14) . . ?
O9' S1' C59' 97.7(17) . . ?
C60' S1' C59' 94.0(7) . . ?
S1' C59' H59D 109.5 . . ?
S1' C59' H59E 109.5 . . ?
H59D C59' H59E 109.5 . . ?
S1' C59' H59F 109.5 . . ?
H59D C59' H59F 109.5 . . ?
H59E C59' H59F 109.5 . . ?
S1' C60' H60D 109.5 . . ?
S1' C60' H60E 109.5 . . ?
H60D C60' H60E 109.5 . . ?
S1' C60' H60F 109.5 . . ?
H60D C60' H60F 109.5 . . ?
H60E C60' H60F 109.5 . . ?

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
C6 C1 C2 C3 1.2(6) . . . . ?
C7 C1 C2 C3 174.2(4) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 1.3(7) . . . . ?
C4 C5 C6 C1 -1.2(6) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
C7 C1 C6 C5 -172.9(4) . . . . ?
C2 C1 C7 N1 -48.8(5) . . . . ?
C6 C1 C7 N1 124.1(4) . . . . ?
C2 C1 C7 C8 134.1(4) . . . . ?
C6 C1 C7 C8 -53.0(6) . . . . ?
N1 C7 C8 C9 -1.7(4) . . . . ?
C1 C7 C8 C9 175.5(4) . . . . ?
N1 C7 C8 C14 177.5(4) . . . . ?
C1 C7 C8 C14 -5.4(7) . . . . ?
C7 C8 C9 O1 1.5(4) . . . . ?
C14 C8 C9 O1 -177.8(3) . . . . ?
C7 C8 C9 N2 -176.4(3) . . . . ?
C14 C8 C9 N2 4.3(6) . . . . ?
N2 C10 C13 C12 -175.8(3) . . . . ?
N3 C10 C13 C12 4.0(5) . . . . ?
N2 C10 C13 C14 4.8(5) . . . . ?
N3 C10 C13 C14 -175.4(3) . . . . ?
O3 C12 C13 C10 172.4(4) . . . . ?
N4 C12 C13 C10 -7.5(5) . . . . ?
O3 C12 C13 C14 -8.1(6) . . . . ?
N4 C12 C13 C14 172.0(3) . . . . ?
C9 C8 C14 C15 -123.6(3) . . . . ?
C7 C8 C14 C15 57.4(5) . . . . ?
C9 C8 C14 C13 1.7(4) . . . . ?
C7 C8 C14 C13 -177.3(4) . . . . ?
C9 C8 C14 C22 123.3(4) . . . . ?
C7 C8 C14 C22 -55.7(5) . . . . ?
C10 C13 C14 C8 -5.9(4) . . . . ?
C12 C13 C14 C8 174.7(3) . . . . ?
C10 C13 C14 C15 121.1(4) . . . . ?
C12 C13 C14 C15 -58.3(4) . . . . ?
C10 C13 C14 C22 -128.3(3) . . . . ?
C12 C13 C14 C22 52.3(4) . . . . ?
C8 C14 C15 C16 60.4(5) . . . . ?
C13 C14 C15 C16 -62.5(5) . . . . ?
C22 C14 C15 C16 -179.7(4) . . . . ?
C8 C14 C15 C20 -119.9(3) . . . . ?
C13 C14 C15 C20 117.2(3) . . . . ?
C22 C14 C15 C20 0.0(3) . . . . ?
C20 C15 C16 C17 -1.1(5) . . . . ?
C14 C15 C16 C17 178.5(3) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C17 C18 C19 C20 -0.2(6) . . . . ?
C18 C19 C20 C15 -0.6(6) . . . . ?
C18 C19 C20 C21 178.1(4) . . . . ?
C16 C15 C20 C19 1.3(5) . . . . ?
C14 C15 C20 C19 -178.4(3) . . . . ?
C16 C15 C20 C21 -177.7(3) . . . . ?
C14 C15 C20 C21 2.6(4) . . . . ?
C19 C20 C21 C22 176.6(4) . . . . ?
C15 C20 C21 C22 -4.6(4) . . . . ?
C19 C20 C21 C23 8.9(6) . . . . ?
C15 C20 C21 C23 -172.2(3) . . . . ?
C20 C21 C22 O4 -176.2(3) . . . . ?
C23 C21 C22 O4 -8.2(5) . . . . ?
C20 C21 C22 C14 4.5(4) . . . . ?
C23 C21 C22 C14 172.5(3) . . . . ?
C8 C14 C22 O4 -59.9(4) . . . . ?
C15 C14 C22 O4 178.0(3) . . . . ?
C13 C14 C22 O4 59.8(4) . . . . ?
C8 C14 C22 C21 119.4(3) . . . . ?
C15 C14 C22 C21 -2.7(3) . . . . ?
C13 C14 C22 C21 -120.9(3) . . . . ?
C22 C21 C23 C24 119.6(4) . . . . ?
C20 C21 C23 C24 -74.2(4) . . . . ?
C21 C23 C24 C25 -28.7(13) . . . . ?
C21 C23 C24 C25' -6(2) . . . . ?
C21 C23 C24 C29' -174.2(18) . . . . ?
C21 C23 C24 C29 149.8(8) . . . . ?
C25' C24 C25 C26 80(8) . . . . ?
C29' C24 C25 C26 -36(2) . . . . ?
C29 C24 C25 C26 1(2) . . . . ?
C23 C24 C25 C26 179.6(10) . . . . ?
C24 C25 C26 C27 3(2) . . . . ?
C25 C26 C27 C28 -6(2) . . . . ?
C26 C27 C28 C29 5(2) . . . . ?
C27 C28 C29 C24 -1.1(17) . . . . ?
C25 C24 C29 C28 -1.9(15) . . . . ?
C25' C24 C29 C28 -22(2) . . . . ?
C29' C24 C29 C28 95(2) . . . . ?
C23 C24 C29 C28 179.4(8) . . . . ?
C25 C24 C25' C26' -91(9) . . . . ?
C29' C24 C25' C26' -17(4) . . . . ?
C29 C24 C25' C26' 18(3) . . . . ?
C23 C24 C25' C26' 175.7(19) . . . . ?
C24 C25' C26' C27' 0(5) . . . . ?
C25' C26' C27' C28' 25(5) . . . . ?
C26' C27' C28' C29' -34(5) . . . . ?
C27' C28' C29' C24 16(4) . . . . ?
C25 C24 C29' C28' 28(3) . . . . ?
C25' C24 C29' C28' 8(3) . . . . ?
C29 C24 C29' C28' -72(2) . . . . ?
C23 C24 C29' C28' 176.7(16) . . . . ?
C35 C30 C31 C32 0.2(6) . . . . ?
C36 C30 C31 C32 173.5(4) . . . . ?
C30 C31 C32 C33 -0.3(6) . . . . ?
C31 C32 C33 C34 -0.3(7) . . . . ?
C32 C33 C34 C35 1.0(8) . . . . ?
C33 C34 C35 C30 -1.0(8) . . . . ?
C31 C30 C35 C34 0.4(7) . . . . ?
C36 C30 C35 C34 -173.1(4) . . . . ?
C31 C30 C36 N5 -118.2(4) . . . . ?
C35 C30 C36 N5 55.1(5) . . . . ?
C31 C30 C36 C37 62.9(6) . . . . ?
C35 C30 C36 C37 -123.9(5) . . . . ?
N5 C36 C37 C38 -1.1(5) . . . . ?
C30 C36 C37 C38 177.9(4) . . . . ?
N5 C36 C37 C43 -179.3(4) . . . . ?
C30 C36 C37 C43 -0.3(7) . . . . ?
C36 C37 C38 O5 0.9(4) . . . . ?
C43 C37 C38 O5 179.4(3) . . . . ?
C36 C37 C38 N6 -176.2(4) . . . . ?
C43 C37 C38 N6 2.3(7) . . . . ?
N7 C39 C42 C41 -2.1(5) . . . . ?
N6 C39 C42 C41 176.6(3) . . . . ?
N7 C39 C42 C43 177.0(3) . . . . ?
N6 C39 C42 C43 -4.3(6) . . . . ?
O7 C41 C42 C39 -175.2(4) . . . . ?
N8 C41 C42 C39 6.2(5) . . . . ?
O7 C41 C42 C43 5.7(5) . . . . ?
N8 C41 C42 C43 -173.0(3) . . . . ?
C38 C37 C43 C44 123.2(4) . . . . ?
C36 C37 C43 C44 -58.9(5) . . . . ?
C38 C37 C43 C42 -3.9(5) . . . . ?
C36 C37 C43 C42 174.0(4) . . . . ?
C38 C37 C43 C51 -126.8(4) . . . . ?
C36 C37 C43 C51 51.1(5) . . . . ?
C39 C42 C43 C37 4.9(5) . . . . ?
C41 C42 C43 C37 -176.0(3) . . . . ?
C39 C42 C43 C44 -120.3(4) . . . . ?
C41 C42 C43 C44 58.8(4) . . . . ?
C39 C42 C43 C51 124.6(4) . . . . ?
C41 C42 C43 C51 -56.3(4) . . . . ?
C37 C43 C44 C45 -64.8(5) . . . . ?
C42 C43 C44 C45 58.2(5) . . . . ?
C51 C43 C44 C45 -179.6(4) . . . . ?
C37 C43 C44 C49 109.7(3) . . . . ?
C42 C43 C44 C49 -127.4(3) . . . . ?
C51 C43 C44 C49 -5.2(4) . . . . ?
C49 C44 C45 C46 0.8(6) . . . . ?
C43 C44 C45 C46 174.7(4) . . . . ?
C44 C45 C46 C47 0.3(7) . . . . ?
C45 C46 C47 C48 -1.4(7) . . . . ?
C46 C47 C48 C49 1.3(6) . . . . ?
C47 C48 C49 C44 -0.2(6) . . . . ?
C47 C48 C49 C50 -177.3(4) . . . . ?
C45 C44 C49 C48 -0.9(6) . . . . ?
C43 C44 C49 C48 -176.0(3) . . . . ?
C45 C44 C49 C50 176.7(3) . . . . ?
C43 C44 C49 C50 1.6(4) . . . . ?
C48 C49 C50 C51 -179.1(4) . . . . ?
C44 C49 C50 C51 3.5(4) . . . . ?
C48 C49 C50 C52 4.5(6) . . . . ?
C44 C49 C50 C52 -172.9(3) . . . . ?
C49 C50 C51 O8 177.2(3) . . . . ?
C52 C50 C51 O8 -6.3(6) . . . . ?
C49 C50 C51 C43 -7.0(4) . . . . ?
C52 C50 C51 C43 169.5(3) . . . . ?
C37 C43 C51 O8 65.6(5) . . . . ?
C44 C43 C51 O8 -176.9(3) . . . . ?
C42 C43 C51 O8 -53.6(5) . . . . ?
C37 C43 C51 C50 -110.1(3) . . . . ?
C44 C43 C51 C50 7.3(4) . . . . ?
C42 C43 C51 C50 130.7(3) . . . . ?
C51 C50 C52 C53 94.7(10) . . . . ?
C49 C50 C52 C53 -89.3(10) . . . . ?
C51 C50 C52 C53' 87.3(7) . . . . ?
C49 C50 C52 C53' -96.7(7) . . . . ?
C50 C52 C53 C54 168.5(8) . . . . ?
C53' C52 C53 C54 -103(12) . . . . ?
C50 C52 C53 C58 -24.8(19) . . . . ?
C53' C52 C53 C58 64(11) . . . . ?
C58 C53 C54 C55 0.0 . . . . ?
C52 C53 C54 C55 167.4(16) . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C54 C55 C56 C57 0.0 . . . . ?
C55 C56 C57 C58 0.0 . . . . ?
C56 C57 C58 C53 0.0 . . . . ?
C54 C53 C58 C57 0.0 . . . . ?
C52 C53 C58 C57 -165.9(19) . . . . ?
C50 C52 C53' C54' 179.1(7) . . . . ?
C53 C52 C53' C54' 85(12) . . . . ?
C50 C52 C53' C58' 2.4(12) . . . . ?
C53 C52 C53' C58' -92(12) . . . . ?
C58' C53' C54' C55' 0.0 . . . . ?
C52 C53' C54' C55' -176.6(11) . . . . ?
C53' C54' C55' C56' 0.0 . . . . ?
C54' C55' C56' C57' 0.0 . . . . ?
C55' C56' C57' C58' 0.0 . . . . ?
C56' C57' C58' C53' 0.0 . . . . ?
C54' C53' C58' C57' 0.0 . . . . ?
C52 C53' C58' C57' 176.8(11) . . . . ?
C8 C7 N1 O1 1.2(4) . . . . ?
C1 C7 N1 O1 -176.4(3) . . . . ?
C13 C10 N2 C9 1.3(5) . . . . ?
N3 C10 N2 C9 -178.5(3) . . . . ?
O1 C9 N2 C10 176.2(3) . . . . ?
C8 C9 N2 C10 -6.0(5) . . . . ?
O2 C11 N3 C10 175.1(4) . . . . ?
N4 C11 N3 C10 -5.6(5) . . . . ?
C13 C10 N3 C11 2.9(5) . . . . ?
N2 C10 N3 C11 -177.2(3) . . . . ?
O2 C11 N4 C12 -179.2(4) . . . . ?
N3 C11 N4 C12 1.5(6) . . . . ?
O3 C12 N4 C11 -174.9(4) . . . . ?
C13 C12 N4 C11 5.0(6) . . . . ?
C37 C36 N5 O5 0.8(4) . . . . ?
C30 C36 N5 O5 -178.3(3) . . . . ?
C37 C38 N6 C39 -0.7(6) . . . . ?
O5 C38 N6 C39 -177.7(3) . . . . ?
C42 C39 N6 C38 1.7(6) . . . . ?
N7 C39 N6 C38 -179.5(3) . . . . ?
C42 C39 N7 C40 -2.8(6) . . . . ?
N6 C39 N7 C40 178.4(3) . . . . ?
O6 C40 N7 C39 -177.7(4) . . . . ?
N8 C40 N7 C39 3.0(5) . . . . ?
O6 C40 N8 C41 -177.5(4) . . . . ?
N7 C40 N8 C41 1.8(6) . . . . ?
O7 C41 N8 C40 174.9(4) . . . . ?
C42 C41 N8 C40 -6.4(6) . . . . ?
C8 C9 O1 N1 -0.8(4) . . . . ?
N2 C9 O1 N1 177.3(3) . . . . ?
C7 N1 O1 C9 -0.3(4) . . . . ?
C37 C38 O5 N5 -0.5(4) . . . . ?
N6 C38 O5 N5 177.0(4) . . . . ?
C36 N5 O5 C38 -0.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C60 H60B O8 0.96 2.65 3.347(18) 129.8 4_565
C59' H59F S1' 0.96 2.92 3.51(2) 120.7 2_644
N2 H2A O4 0.923(18) 1.76(2) 2.673(4) 168(4) 3_756
N8 H8 O6 0.95(4) 1.91(4) 2.855(4) 173(4) 3_675
N3 H3A O2 0.869(18) 2.15(2) 2.984(4) 162(3) 3_746
N7 H7 O8 0.878(19) 1.95(2) 2.818(4) 170(4) 3_665
N6 H6A S1 0.894(19) 2.97(3) 3.777(4) 151(4) .
N6 H6A O9 0.894(19) 1.82(3) 2.705(16) 168(5) .
N6 H6A O9' 0.894(19) 1.77(3) 2.66(2) 176(5) .
C60 H60B O8 0.96 2.65 3.347(18) 129.8 4_565
C59' H59F S1' 0.96 2.92 3.51(2) 120.7 2_644
N2 H2A O4 0.923(18) 1.76(2) 2.673(4) 168(4) 3_756
N8 H8 O6 0.95(4) 1.91(4) 2.855(4) 173(4) 3_675
N3 H3A O2 0.869(18) 2.15(2) 2.984(4) 162(3) 3_746
N7 H7 O8 0.878(19) 1.95(2) 2.818(4) 170(4) 3_665
N6 H6A S1 0.894(19) 2.97(3) 3.777(4) 151(4) .
N6 H6A O9 0.894(19) 1.82(3) 2.705(16) 168(5) .
N6 H6A O9' 0.894(19) 1.77(3) 2.66(2) 176(5) .

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.053

_shelxl_version_number           2012-9



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMSO-D6'
