# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Nicholas Westwood'
_publ_contact_author_email       NJW3@ST-ANDREWS.AC.UK

_publ_section_title              
;
Synthesis and Biological Evaluation of Functionalised
Tetrahydro-b-carboline Analogues as Inhibitors of Toxoplasma gondii Invasion.
;
loop_
_publ_author_name
'Nicholas Westwood'
'Jeralyn D. Haraldsen'
'Jonathan J. Hollick'
'Gu Liu'
'Stephen Patterson'
;
A.Slawin
;
'Jeffrey G. A. Walton'
'Gary E. Ward'

# Attachment '7b1.cif'

data_7b
_database_code_depnum_ccdc_archive 'CCDC 719462'

# start Validation Reply Form

_vrf_PLAT029_7b                  
;
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.94
RESPONSE: Poor crystal quality. Limited data.
;

# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H23 N3 O3'
_chemical_formula_sum            'C23 H23 N3 O3'
_chemical_formula_weight         389.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.9563(12)
_cell_length_b                   8.4315(12)
_cell_length_c                   28.798(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1931.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2759
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      51.55

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9299
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21966
_diffrn_reflns_av_R_equivalents  0.2426
_diffrn_reflns_av_sigmaI/netI    0.1079
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         5.47
_diffrn_reflns_theta_max         67.44
_reflns_number_total             3196
_reflns_number_gt                2422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+3.4687P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3196
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.1033
_refine_ls_wR_factor_ref         0.2500
_refine_ls_wR_factor_gt          0.2259
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3467(7) 0.4641(7) 0.03079(18) 0.0379(14) Uani 1 1 d . . .
H1N H 0.2345 0.4488 0.0441 0.07(3) Uiso 1 1 calc R . .
C2 C 0.4958(8) 0.4150(8) 0.0506(2) 0.0319(15) Uani 1 1 d . . .
C3 C 0.5044(8) 0.3463(8) 0.0986(2) 0.0337(15) Uani 1 1 d . . .
H3A H 0.4304 0.2506 0.1002 0.040 Uiso 1 1 calc R . .
N4 N 0.6817(7) 0.2971(6) 0.10453(17) 0.0332(13) Uani 1 1 d . . .
C5 C 0.7362(9) 0.1905(8) 0.1358(2) 0.0344(16) Uani 1 1 d . . .
O5 O 0.6526(6) 0.1014(5) 0.15985(15) 0.0394(12) Uani 1 1 d . . .
N6 N 0.9139(7) 0.1977(7) 0.13622(19) 0.0348(13) Uani 1 1 d . . .
C7 C 0.9694(9) 0.3095(8) 0.1054(2) 0.0341(16) Uani 1 1 d . . .
O7 O 1.1156(6) 0.3325(6) 0.09539(17) 0.0452(13) Uani 1 1 d . . .
C8 C 0.8157(8) 0.3955(8) 0.0863(2) 0.0312(14) Uani 1 1 d . . .
H8A H 0.8086 0.5022 0.1014 0.037 Uiso 1 1 calc R . .
C9 C 0.8060(8) 0.4172(8) 0.0345(2) 0.0322(15) Uani 1 1 d . . .
H9A H 0.8803 0.5051 0.0245 0.039 Uiso 1 1 calc R . .
H9B H 0.8421 0.3191 0.0184 0.039 Uiso 1 1 calc R . .
C10 C 0.6283(9) 0.4541(8) 0.0229(2) 0.0326(15) Uani 1 1 d . . .
C11 C 0.5599(9) 0.5355(9) -0.0170(2) 0.0378(16) Uani 1 1 d . . .
C12 C 0.6289(10) 0.6129(9) -0.0552(2) 0.0441(18) Uani 1 1 d . . .
H12A H 0.7473 0.6168 -0.0593 0.053 Uiso 1 1 calc R . .
C13 C 0.5233(10) 0.6844(9) -0.0873(2) 0.0412(18) Uani 1 1 d . . .
H13A H 0.5694 0.7376 -0.1135 0.049 Uiso 1 1 calc R . .
C14 C 0.3499(11) 0.6784(8) -0.0813(2) 0.0449(19) Uani 1 1 d . . .
H14A H 0.2792 0.7260 -0.1039 0.054 Uiso 1 1 calc R . .
C15 C 0.2780(10) 0.6052(9) -0.0434(2) 0.0417(18) Uani 1 1 d . . .
H15A H 0.1593 0.6015 -0.0401 0.050 Uiso 1 1 calc R . .
C16 C 0.3813(9) 0.5375(8) -0.0105(2) 0.0336(16) Uani 1 1 d . . .
C17 C 0.4539(8) 0.4625(8) 0.1366(2) 0.0300(14) Uani 1 1 d . . .
C18 C 0.4102(9) 0.4040(9) 0.1802(2) 0.0377(17) Uani 1 1 d . . .
H18A H 0.4014 0.2927 0.1848 0.045 Uiso 1 1 calc R . .
C19 C 0.3797(8) 0.5053(8) 0.2168(2) 0.0319(15) Uani 1 1 d . . .
O19 O 0.3363(7) 0.4375(6) 0.25824(16) 0.0503(14) Uani 1 1 d . . .
H19O H 0.3499 0.5152 0.2833 0.07(3) Uiso 1 1 calc R . .
C20 C 0.3891(9) 0.6678(9) 0.2097(2) 0.0426(18) Uani 1 1 d . . .
H20A H 0.3684 0.7384 0.2348 0.051 Uiso 1 1 calc R . .
C21 C 0.4282(9) 0.7273(9) 0.1665(2) 0.0429(19) Uani 1 1 d . . .
H21A H 0.4328 0.8387 0.1618 0.052 Uiso 1 1 calc R . .
C22 C 0.4604(9) 0.6260(8) 0.1303(2) 0.0383(17) Uani 1 1 d . . .
H22A H 0.4875 0.6680 0.1006 0.046 Uiso 1 1 calc R . .
C23 C 1.0191(9) 0.0995(9) 0.1659(2) 0.0397(17) Uani 1 1 d . . .
H23A H 1.1324 0.0915 0.1519 0.048 Uiso 1 1 calc R . .
H23B H 0.9709 -0.0087 0.1672 0.048 Uiso 1 1 calc R . .
C24 C 1.0356(10) 0.1616(9) 0.2140(2) 0.0409(17) Uani 1 1 d . . .
H24A H 0.9229 0.1672 0.2285 0.049 Uiso 1 1 calc R . .
H24B H 1.0821 0.2705 0.2130 0.049 Uiso 1 1 calc R . .
C25 C 1.1500(10) 0.0568(9) 0.2437(2) 0.0438(18) Uani 1 1 d . . .
H25A H 1.1189 -0.0556 0.2387 0.053 Uiso 1 1 calc R . .
H25B H 1.2675 0.0707 0.2332 0.053 Uiso 1 1 calc R . .
C26 C 1.1403(11) 0.0929(11) 0.2951(2) 0.054(2) Uani 1 1 d . . .
H26A H 1.2155 0.0215 0.3121 0.081 Uiso 1 1 calc R . .
H26B H 1.0247 0.0777 0.3060 0.081 Uiso 1 1 calc R . .
H26C H 1.1744 0.2031 0.3005 0.081 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.028(3) 0.048(3) 0.038(3) 0.006(3) -0.002(2) 0.002(3)
C2 0.028(4) 0.031(3) 0.037(4) -0.003(3) 0.001(3) 0.006(3)
C3 0.032(4) 0.033(4) 0.037(4) 0.002(3) 0.002(3) 0.001(3)
N4 0.030(3) 0.038(3) 0.031(3) 0.006(2) 0.007(2) -0.004(3)
C5 0.048(5) 0.027(4) 0.029(3) 0.001(3) 0.005(3) -0.008(3)
O5 0.044(3) 0.038(3) 0.037(2) 0.009(2) 0.004(2) -0.006(3)
N6 0.027(4) 0.035(3) 0.042(3) 0.000(3) 0.002(2) -0.002(3)
C7 0.027(4) 0.042(4) 0.033(3) -0.004(3) 0.002(3) -0.003(3)
O7 0.033(3) 0.050(3) 0.052(3) 0.010(2) -0.002(2) -0.003(2)
C8 0.025(4) 0.031(3) 0.038(3) -0.004(3) 0.006(3) -0.006(3)
C9 0.025(4) 0.031(4) 0.041(4) 0.002(3) 0.002(3) 0.002(3)
C10 0.035(4) 0.028(3) 0.035(3) -0.004(3) 0.000(3) -0.009(3)
C11 0.044(5) 0.036(4) 0.032(3) -0.003(3) -0.006(3) -0.003(4)
C12 0.047(5) 0.041(4) 0.044(4) -0.003(3) 0.004(3) -0.004(3)
C13 0.051(5) 0.037(4) 0.035(4) 0.007(3) -0.004(3) 0.010(4)
C14 0.064(6) 0.036(4) 0.035(4) 0.003(3) -0.012(3) 0.013(4)
C15 0.042(5) 0.048(5) 0.036(4) 0.003(3) -0.003(3) 0.004(4)
C16 0.044(5) 0.025(3) 0.032(3) 0.001(3) -0.002(3) 0.002(3)
C17 0.022(3) 0.025(3) 0.043(4) 0.006(3) -0.010(3) -0.003(3)
C18 0.040(4) 0.044(4) 0.030(3) 0.007(3) -0.001(3) 0.000(3)
C19 0.022(4) 0.034(4) 0.040(3) 0.006(3) -0.004(3) -0.002(3)
O19 0.060(4) 0.047(3) 0.044(3) -0.003(3) 0.003(3) 0.005(3)
C20 0.037(4) 0.050(5) 0.041(4) -0.010(3) 0.002(3) -0.001(3)
C21 0.043(5) 0.038(4) 0.047(4) -0.009(3) -0.002(3) 0.011(4)
C22 0.034(4) 0.039(4) 0.041(4) 0.010(3) -0.001(3) 0.002(3)
C23 0.032(4) 0.043(4) 0.044(4) -0.002(3) 0.006(3) 0.006(3)
C24 0.039(4) 0.037(4) 0.047(4) -0.001(3) 0.003(3) 0.000(3)
C25 0.046(5) 0.040(4) 0.045(4) 0.009(3) -0.003(3) -0.004(4)
C26 0.048(5) 0.065(5) 0.049(4) 0.010(4) -0.004(4) -0.011(4)

_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
N1 C16 1.369(8) . ?
N1 C2 1.379(8) . ?
N1 H1N 0.9800 . ?
C2 C10 1.362(9) . ?
C2 C3 1.500(9) . ?
C3 N4 1.481(9) . ?
C3 C17 1.523(9) . ?
C3 H3A 1.0000 . ?
N4 C5 1.345(8) . ?
N4 C8 1.449(8) . ?
C5 O5 1.219(7) . ?
C5 N6 1.415(9) . ?
N6 C7 1.369(9) . ?
N6 C23 1.455(9) . ?
C7 O7 1.214(8) . ?
C7 C8 1.523(10) . ?
C8 C9 1.507(9) . ?
C8 H8A 1.0000 . ?
C9 C10 1.485(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.445(9) . ?
C11 C12 1.392(10) . ?
C11 C16 1.434(10) . ?
C12 C13 1.388(10) . ?
C12 H12A 0.9500 . ?
C13 C14 1.391(11) . ?
C13 H13A 0.9500 . ?
C14 C15 1.377(10) . ?
C14 H14A 0.9500 . ?
C15 C16 1.378(9) . ?
C15 H15A 0.9500 . ?
C17 C18 1.392(9) . ?
C17 C22 1.392(9) . ?
C18 C19 1.379(9) . ?
C18 H18A 0.9500 . ?
C19 O19 1.366(8) . ?
C19 C20 1.387(10) . ?
O19 H19O 0.9800 . ?
C20 C21 1.378(10) . ?
C20 H20A 0.9500 . ?
C21 C22 1.371(10) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
C23 C24 1.488(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.530(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.513(10) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C2 108.8(6) . . ?
C16 N1 H1N 125.6 . . ?
C2 N1 H1N 125.6 . . ?
C10 C2 N1 110.6(6) . . ?
C10 C2 C3 126.6(6) . . ?
N1 C2 C3 122.4(6) . . ?
N4 C3 C2 105.0(5) . . ?
N4 C3 C17 110.4(5) . . ?
C2 C3 C17 113.7(5) . . ?
N4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C17 C3 H3A 109.2 . . ?
C5 N4 C8 112.8(5) . . ?
C5 N4 C3 124.9(5) . . ?
C8 N4 C3 119.9(5) . . ?
O5 C5 N4 128.1(7) . . ?
O5 C5 N6 124.5(6) . . ?
N4 C5 N6 107.4(6) . . ?
C7 N6 C5 110.3(6) . . ?
C7 N6 C23 126.0(6) . . ?
C5 N6 C23 123.7(6) . . ?
O7 C7 N6 125.0(7) . . ?
O7 C7 C8 127.5(6) . . ?
N6 C7 C8 107.6(6) . . ?
N4 C8 C9 113.0(5) . . ?
N4 C8 C7 100.8(5) . . ?
C9 C8 C7 117.1(5) . . ?
N4 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C10 C9 C8 107.2(5) . . ?
C10 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C2 C10 C11 106.8(6) . . ?
C2 C10 C9 123.8(6) . . ?
C11 C10 C9 129.5(6) . . ?
C12 C11 C16 119.2(7) . . ?
C12 C11 C10 134.7(7) . . ?
C16 C11 C10 106.0(6) . . ?
C13 C12 C11 119.5(7) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 120.1(7) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C15 C14 C13 121.8(7) . . ?
C15 C14 H14A 119.1 . . ?
C13 C14 H14A 119.1 . . ?
C14 C15 C16 118.8(7) . . ?
C14 C15 H15A 120.6 . . ?
C16 C15 H15A 120.6 . . ?
N1 C16 C15 131.7(7) . . ?
N1 C16 C11 107.9(6) . . ?
C15 C16 C11 120.4(6) . . ?
C18 C17 C22 118.5(6) . . ?
C18 C17 C3 119.1(6) . . ?
C22 C17 C3 122.3(6) . . ?
C19 C18 C17 121.0(7) . . ?
C19 C18 H18A 119.5 . . ?
C17 C18 H18A 119.5 . . ?
O19 C19 C18 116.9(6) . . ?
O19 C19 C20 123.8(6) . . ?
C18 C19 C20 119.3(6) . . ?
C19 O19 H19O 109.5 . . ?
C21 C20 C19 120.3(7) . . ?
C21 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C22 C21 C20 120.2(7) . . ?
C22 C21 H21A 119.9 . . ?
C20 C21 H21A 119.9 . . ?
C21 C22 C17 120.7(7) . . ?
C21 C22 H22A 119.6 . . ?
C17 C22 H22A 119.6 . . ?
N6 C23 C24 113.5(6) . . ?
N6 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
N6 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C25 111.7(6) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 107.9 . . ?
C26 C25 C24 113.6(7) . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C16 N1 C2 C10 -0.3(8) . . . . ?
C16 N1 C2 C3 173.1(6) . . . . ?
C10 C2 C3 N4 -12.6(9) . . . . ?
N1 C2 C3 N4 175.1(6) . . . . ?
C10 C2 C3 C17 108.2(8) . . . . ?
N1 C2 C3 C17 -64.1(8) . . . . ?
C2 C3 N4 C5 -159.6(6) . . . . ?
C17 C3 N4 C5 77.5(7) . . . . ?
C2 C3 N4 C8 39.1(7) . . . . ?
C17 C3 N4 C8 -83.8(7) . . . . ?
C8 N4 C5 O5 173.2(6) . . . . ?
C3 N4 C5 O5 10.8(10) . . . . ?
C8 N4 C5 N6 -7.2(7) . . . . ?
C3 N4 C5 N6 -169.7(6) . . . . ?
O5 C5 N6 C7 180.0(6) . . . . ?
N4 C5 N6 C7 0.4(8) . . . . ?
O5 C5 N6 C23 -0.5(11) . . . . ?
N4 C5 N6 C23 179.9(5) . . . . ?
C5 N6 C7 O7 -173.5(7) . . . . ?
C23 N6 C7 O7 7.1(11) . . . . ?
C5 N6 C7 C8 6.0(7) . . . . ?
C23 N6 C7 C8 -173.5(6) . . . . ?
C5 N4 C8 C9 136.0(6) . . . . ?
C3 N4 C8 C9 -60.6(7) . . . . ?
C5 N4 C8 C7 10.3(6) . . . . ?
C3 N4 C8 C7 173.6(5) . . . . ?
O7 C7 C8 N4 170.0(7) . . . . ?
N6 C7 C8 N4 -9.5(6) . . . . ?
O7 C7 C8 C9 47.0(10) . . . . ?
N6 C7 C8 C9 -132.5(6) . . . . ?
N4 C8 C9 C10 45.7(7) . . . . ?
C7 C8 C9 C10 162.1(6) . . . . ?
N1 C2 C10 C11 0.8(7) . . . . ?
C3 C2 C10 C11 -172.3(7) . . . . ?
N1 C2 C10 C9 -179.8(6) . . . . ?
C3 C2 C10 C9 7.1(11) . . . . ?
C8 C9 C10 C2 -22.5(9) . . . . ?
C8 C9 C10 C11 156.7(7) . . . . ?
C2 C10 C11 C12 174.7(8) . . . . ?
C9 C10 C11 C12 -4.7(13) . . . . ?
C2 C10 C11 C16 -0.9(8) . . . . ?
C9 C10 C11 C16 179.7(7) . . . . ?
C16 C11 C12 C13 -2.8(11) . . . . ?
C10 C11 C12 C13 -178.0(8) . . . . ?
C11 C12 C13 C14 0.0(11) . . . . ?
C12 C13 C14 C15 1.3(12) . . . . ?
C13 C14 C15 C16 0.6(11) . . . . ?
C2 N1 C16 C15 179.3(7) . . . . ?
C2 N1 C16 C11 -0.3(8) . . . . ?
C14 C15 C16 N1 177.0(7) . . . . ?
C14 C15 C16 C11 -3.5(10) . . . . ?
C12 C11 C16 N1 -175.7(6) . . . . ?
C10 C11 C16 N1 0.7(8) . . . . ?
C12 C11 C16 C15 4.7(11) . . . . ?
C10 C11 C16 C15 -178.9(6) . . . . ?
N4 C3 C17 C18 -80.5(7) . . . . ?
C2 C3 C17 C18 161.9(6) . . . . ?
N4 C3 C17 C22 95.2(7) . . . . ?
C2 C3 C17 C22 -22.5(9) . . . . ?
C22 C17 C18 C19 -2.2(10) . . . . ?
C3 C17 C18 C19 173.6(6) . . . . ?
C17 C18 C19 O19 179.5(6) . . . . ?
C17 C18 C19 C20 1.4(10) . . . . ?
O19 C19 C20 C21 -177.8(6) . . . . ?
C18 C19 C20 C21 0.1(11) . . . . ?
C19 C20 C21 C22 -0.9(11) . . . . ?
C20 C21 C22 C17 0.1(11) . . . . ?
C18 C17 C22 C21 1.4(11) . . . . ?
C3 C17 C22 C21 -174.3(6) . . . . ?
C7 N6 C23 C24 97.7(8) . . . . ?
C5 N6 C23 C24 -81.7(8) . . . . ?
N6 C23 C24 C25 -178.8(6) . . . . ?
C23 C24 C25 C26 -167.1(6) . . . . ?

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
N1 H1N O7 0.98 2.01 2.841(7) 141.3 1_455
O19 H19O O5 0.98 1.79 2.735(7) 160.4 3_655

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.936
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.079