# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Bernhard Witulski'
_publ_contact_author_email       BERNHARD.WITULSKI@ENSICAEN.FR

_publ_section_title              
;
First total synthesis of antiostatin A1
a potent carbazole-based naturally occuring antioxidant
;
loop_
_publ_author_name
'Bernhard Witulski'
'Carole Alayrac'
'Dieter Schollmeyer'

# Attachment 'ca403.cif'

data_ca403
_database_code_depnum_ccdc_archive 'CCDC 709652'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        ?

_chemical_name_common            'Antiostatin A1'

_chemical_formula_moiety         'C20 H24 N2 O2'

_chemical_formula_sum            'C20 H24 N2 O2'

_chemical_compound_source        synthetic

_exptl_crystal_recrystallization_method 'ethyl acetate and pentane'

_chemical_melting_point          490

_exptl_crystal_description       needle

_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      193(2)

_chemical_formula_weight         324.41

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 21/n'

_symmetry_int_tables_number      14

_chemical_absolute_configuration ?

_symmetry_space_group_name_Hall  '-P 2yn'

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   4.9084(2)

_cell_length_b                   24.3209(12)

_cell_length_c                   14.3390(8)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.069(3)

_cell_angle_gamma                90.00

_cell_volume                     1711.74(15)

_cell_formula_units_Z            4

_cell_measurement_temperature    193(2)

_cell_measurement_reflns_used    2220

_cell_measurement_theta_min      2.1

_cell_measurement_theta_max      23.6

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.16

_exptl_crystal_size_min          0.05

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.259

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             696

_exptl_absorpt_coefficient_mu    0.082

_exptl_absorpt_correction_type   none

#_exptl_absorpt_correction_T_min 0.9799

#_exptl_absorpt_correction_T_max 0.9959

#_exptl_absorpt_process_details 'Corinc (Dr\"ager, 1971)'

_exptl_special_details           
;

?

;

_diffrn_radiation_probe          ?

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71069

_diffrn_source                   'sealed Tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'SMART CCD'

_diffrn_measurement_device       '\k-geometry diffractometer'

_diffrn_measurement_method       'CCD scan'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            18097

_diffrn_reflns_av_R_equivalents  0.1027

_diffrn_reflns_av_sigmaI/netI    0.1144

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       6

_diffrn_reflns_limit_k_min       -31

_diffrn_reflns_limit_k_max       31

_diffrn_reflns_limit_l_min       -18

_diffrn_reflns_limit_l_max       18

_diffrn_reflns_theta_min         1.42

_diffrn_reflns_theta_max         27.90

_reflns_number_total             4085

_reflns_number_gt                2250

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 V2.0 (Bruker, 2006)'

_computing_cell_refinement       'APEX2 V2.0 (Bruker, 2006)'

_computing_data_reduction        'APEX2 V2.0 (Bruker, 2006)'

_computing_structure_solution    'SIR-97 (Altomare, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    ?

_computing_publication_material  ?

_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.

;

_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^)+(0.0500P)^2^+0.0000P] 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         4085

_refine_ls_number_parameters     220

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.1064

_refine_ls_R_factor_gt           0.0477

_refine_ls_wR_factor_ref         0.1120

_refine_ls_wR_factor_obs         0.0979

_refine_ls_goodness_of_fit_ref   0.860

_refine_ls_restrained_S_all      0.865

_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

N1 N 0.6915(4) 0.28081(8) 0.29098(14) 0.0276(5) Uani 1 1 d . . .
H1 H 0.6871 0.2476 0.3402 0.033 Uiso 1 1 d R . .
C2 C 0.8282(5) 0.28042(9) 0.20667(16) 0.0253(5) Uani 1 1 d . . .
C3 C 1.0300(5) 0.24341(9) 0.17765(16) 0.0271(6) Uani 1 1 d . . .
C4 C 1.1385(5) 0.25155(9) 0.08877(16) 0.0269(6) Uani 1 1 d . . .
C5 C 1.0475(5) 0.29594(9) 0.03315(15) 0.0239(5) Uani 1 1 d . . .
C6 C 0.8525(5) 0.33301(9) 0.06445(16) 0.0236(5) Uani 1 1 d . . .
C7 C 0.7402(5) 0.32545(9) 0.15296(16) 0.0242(5) Uani 1 1 d . . .
C8 C 0.5403(5) 0.35452(9) 0.20834(17) 0.0257(5) Uani 1 1 d . . .
C9 C 0.3793(5) 0.40193(10) 0.19562(17) 0.0319(6) Uani 1 1 d . . .
H9 H 0.3932 0.4229 0.1400 0.038 Uiso 1 1 calc R . .
C10 C 0.1999(6) 0.41746(11) 0.26581(18) 0.0387(7) Uani 1 1 d . . .
H10 H 0.0913 0.4495 0.2580 0.046 Uiso 1 1 calc R . .
C11 C 0.1773(6) 0.38678(11) 0.3474(2) 0.0394(7) Uani 1 1 d . . .
H11 H 0.0507 0.3980 0.3938 0.047 Uiso 1 1 calc R . .
C12 C 0.3335(5) 0.34066(10) 0.36265(17) 0.0330(6) Uani 1 1 d . . .
H12 H 0.3188 0.3202 0.4188 0.040 Uiso 1 1 calc R . .
C13 C 0.5138(5) 0.32517(10) 0.29259(16) 0.0267(5) Uani 1 1 d . . .
C14 C 1.1208(5) 0.19917(9) 0.24504(18) 0.0334(6) Uani 1 1 d . . .
H14A H 1.1336 0.2155 0.3082 0.040 Uiso 1 1 calc R . .
H14B H 1.3058 0.1869 0.2271 0.040 Uiso 1 1 calc R . .
C15 C 0.9351(5) 0.14878(10) 0.24978(19) 0.0378(7) Uani 1 1 d . . .
H15A H 0.9916 0.1260 0.3037 0.045 Uiso 1 1 calc R . .
H15B H 0.7466 0.1614 0.2616 0.045 Uiso 1 1 calc R . .
C16 C 0.9335(6) 0.11318(11) 0.1645(2) 0.0460(8) Uani 1 1 d . . .
H16A H 1.1225 0.1018 0.1500 0.055 Uiso 1 1 calc R . .
H16B H 0.8642 0.1348 0.1109 0.055 Uiso 1 1 calc R . .
C17 C 0.7579(7) 0.06219(12) 0.1769(2) 0.0638(9) Uani 1 1 d D . .
H17A H 0.8201 0.0420 0.2329 0.077 Uiso 1 1 calc R . .
H17B H 0.5670 0.0737 0.1876 0.077 Uiso 1 1 calc R . .
C18 C 0.7670(11) 0.02393(16) 0.0938(3) 0.125(2) Uani 1 1 d D . .
H18A H 0.6560 0.0392 0.0432 0.187 Uiso 1 1 calc R . .
H18B H 0.6951 -0.0121 0.1117 0.187 Uiso 1 1 calc R . .
H18C H 0.9558 0.0199 0.0727 0.187 Uiso 1 1 calc R . .
C19 C 1.3598(5) 0.21477(10) 0.04902(18) 0.0320(6) Uani 1 1 d . . .
H19A H 1.4392 0.1926 0.0992 0.048 Uiso 1 1 calc R . .
H19B H 1.5021 0.2375 0.0206 0.048 Uiso 1 1 calc R . .
H19C H 1.2810 0.1905 0.0016 0.048 Uiso 1 1 calc R . .
O20 O 1.1567(3) 0.30033(6) -0.05550(11) 0.0316(4) Uani 1 1 d . . .
H20 H 1.1916 0.3421 -0.0605 0.047 Uiso 1 1 d R . .
N21 N 0.7595(4) 0.37770(7) 0.00832(13) 0.0255(5) Uani 1 1 d . . .
H21 H 0.5913 0.3942 0.0118 0.031 Uiso 1 1 d R . .
C22 C 0.9181(5) 0.41383(9) -0.03782(16) 0.0274(6) Uani 1 1 d . . .
O23 O 1.1701(3) 0.40856(6) -0.04138(12) 0.0318(4) Uani 1 1 d . . .
C24 C 0.7766(5) 0.46041(9) -0.08634(18) 0.0343(7) Uani 1 1 d . . .
H24A H 0.8338 0.4953 -0.0585 0.052 Uiso 1 1 calc R . .
H24B H 0.5790 0.4562 -0.0796 0.052 Uiso 1 1 calc R . .
H24C H 0.8245 0.4601 -0.1527 0.052 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 0.0308(12) 0.0275(11) 0.0244(11) 0.0048(9) 0.0046(10) 0.0016(10)
C2 0.0259(13) 0.0274(13) 0.0227(13) -0.0005(10) 0.0018(12) -0.0029(11)
C3 0.0254(13) 0.0254(13) 0.0306(15) -0.0023(11) -0.0029(12) -0.0011(11)
C4 0.0219(13) 0.0272(13) 0.0316(15) -0.0037(11) 0.0010(12) -0.0014(11)
C5 0.0251(13) 0.0260(12) 0.0206(13) -0.0044(10) 0.0034(12) -0.0018(11)
C6 0.0248(12) 0.0241(13) 0.0218(12) 0.0005(10) -0.0034(11) -0.0028(11)
C7 0.0239(12) 0.0247(12) 0.0239(13) -0.0017(11) -0.0027(11) -0.0007(11)
C8 0.0235(12) 0.0299(13) 0.0236(12) -0.0024(11) -0.0010(11) -0.0024(11)
C9 0.0341(15) 0.0325(14) 0.0291(14) 0.0020(11) 0.0028(12) 0.0037(12)
C10 0.0433(17) 0.0386(15) 0.0341(15) -0.0030(12) 0.0071(14) 0.0134(14)
C11 0.0379(15) 0.0440(16) 0.0364(15) -0.0069(13) 0.0112(14) 0.0051(14)
C12 0.0355(14) 0.0381(15) 0.0253(14) -0.0001(11) 0.0048(13) -0.0025(13)
C13 0.0243(13) 0.0298(13) 0.0260(13) -0.0009(11) 0.0018(12) -0.0043(11)
C14 0.0322(14) 0.0323(14) 0.0357(15) 0.0025(12) -0.0020(13) 0.0042(12)
C15 0.0318(14) 0.0324(14) 0.0492(17) 0.0104(13) 0.0003(14) 0.0058(13)
C16 0.0411(16) 0.0355(16) 0.061(2) -0.0029(14) 0.0016(16) 0.0022(13)
C17 0.066(2) 0.055(2) 0.070(2) -0.0018(17) -0.0090(19) -0.0141(18)
C18 0.208(6) 0.092(3) 0.075(3) -0.013(2) 0.007(3) -0.069(4)
C19 0.0270(13) 0.0339(14) 0.0350(15) -0.0040(12) 0.0001(13) 0.0039(12)
O20 0.0376(10) 0.0322(9) 0.0251(9) -0.0031(8) 0.0100(9) 0.0004(8)
N21 0.0259(11) 0.0254(10) 0.0251(11) 0.0036(9) 0.0011(9) 0.0028(9)
C22 0.0315(15) 0.0288(14) 0.0217(13) -0.0040(11) 0.0006(12) -0.0030(12)
O23 0.0248(10) 0.0336(10) 0.0372(10) -0.0003(8) 0.0033(9) -0.0035(8)
C24 0.0345(15) 0.0301(14) 0.0385(16) 0.0051(12) 0.0004(13) -0.0009(12)

_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 C2 1.383(3) . ?
N1 C13 1.387(3) . ?
C2 C3 1.402(3) . ?
C2 C7 1.406(3) . ?
C3 C4 1.396(3) . ?
C3 C14 1.513(3) . ?
C4 C5 1.414(3) . ?
C4 C19 1.519(3) . ?
C5 O20 1.384(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.397(3) . ?
C6 N21 1.427(3) . ?
C7 C8 1.447(3) . ?
C8 C13 1.409(3) . ?
C8 C9 1.410(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.393(4) . ?
C11 C12 1.376(3) . ?
C12 C13 1.392(3) . ?
C14 C15 1.529(3) . ?
C15 C16 1.498(4) . ?
C16 C17 1.521(4) . ?
C17 C18 1.512(3) . ?
N21 C22 1.348(3) . ?
C22 O23 1.245(3) . ?
C22 C24 1.499(3) . ?
O20 H20 1.0300 . no
N1 H1 1.0700 . no
N21 H21 0.9200 . no
C9 H9 0.9500 . no
C10 H10 0.9500 . no
C11 H11 0.9500 . no
C12 H12 0.9500 . no
C14 H14A 0.9900 . no
C14 H14B 0.9900 . no
C15 H15A 0.9900 . no
C15 H15B 0.9900 . no
C16 H16A 0.9900 . no
C16 H16B 0.9900 . no
C17 H17A 0.9900 . no
C17 H17B 0.9900 . no
C18 H18A 0.9800 . no
C18 H18B 0.9800 . no
C18 H18C 0.9800 . no
C19 H19A 0.9800 . no
C19 H19B 0.9800 . no
C19 H19C 0.9800 . no
C24 H24A 0.9800 . no
C24 H24B 0.9800 . no
C24 H24C 0.9800 . no

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 N1 C13 108.99(19) . . ?
N1 C2 C3 127.4(2) . . ?
N1 C2 C7 108.9(2) . . ?
C3 C2 C7 123.6(2) . . ?
C4 C3 C2 116.8(2) . . ?
C4 C3 C14 124.9(2) . . ?
C2 C3 C14 118.3(2) . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 C19 122.2(2) . . ?
C5 C4 C19 117.6(2) . . ?
O20 C5 C6 120.9(2) . . ?
O20 C5 C4 117.0(2) . . ?
C6 C5 C4 122.0(2) . . ?
C5 C6 C7 118.7(2) . . ?
C5 C6 N21 122.2(2) . . ?
C7 C6 N21 119.1(2) . . ?
C6 C7 C2 118.6(2) . . ?
C6 C7 C8 134.7(2) . . ?
C2 C7 C8 106.7(2) . . ?
C13 C8 C9 118.2(2) . . ?
C13 C8 C7 106.6(2) . . ?
C9 C8 C7 135.1(2) . . ?
C10 C9 C8 118.9(2) . . ?
C9 C10 C11 120.9(2) . . ?
C12 C11 C10 121.7(2) . . ?
C11 C12 C13 117.5(2) . . ?
N1 C13 C12 128.5(2) . . ?
N1 C13 C8 108.7(2) . . ?
C12 C13 C8 122.8(2) . . ?
C3 C14 C15 115.0(2) . . ?
C16 C15 C14 115.4(2) . . ?
C15 C16 C17 112.2(2) . . ?
C18 C17 C16 113.1(3) . . ?
C22 N21 C6 126.0(2) . . ?
O23 C22 N21 121.8(2) . . ?
O23 C22 C24 121.2(2) . . ?
N21 C22 C24 116.9(2) . . ?
C5 O20 H20 102.00 . . no
C13 N1 H1 124.00 . . no
C2 N1 H1 125.00 . . no
C6 N21 H21 126.00 . . no
C22 N21 H21 105.00 . . no
C8 C9 H9 120.00 . . no
C10 C9 H9 121.00 . . no
C9 C10 H10 120.00 . . no
C11 C10 H10 120.00 . . no
C10 C11 H11 119.00 . . no
C12 C11 H11 119.00 . . no
C11 C12 H12 121.00 . . no
C13 C12 H12 121.00 . . no
C3 C14 H14A 108.00 . . no
C3 C14 H14B 109.00 . . no
C15 C14 H14A 109.00 . . no
C15 C14 H14B 108.00 . . no
H14A C14 H14B 108.00 . . no
C14 C15 H15A 108.00 . . no
C14 C15 H15B 108.00 . . no
C16 C15 H15A 108.00 . . no
C16 C15 H15B 108.00 . . no
H15A C15 H15B 108.00 . . no
C15 C16 H16A 109.00 . . no
C15 C16 H16B 109.00 . . no
C17 C16 H16A 109.00 . . no
C17 C16 H16B 109.00 . . no
H16A C16 H16B 108.00 . . no
C16 C17 H17A 109.00 . . no
C16 C17 H17B 109.00 . . no
C18 C17 H17A 109.00 . . no
C18 C17 H17B 109.00 . . no
H17A C17 H17B 108.00 . . no
C17 C18 H18A 109.00 . . no
C17 C18 H18B 109.00 . . no
C17 C18 H18C 109.00 . . no
H18A C18 H18B 109.00 . . no
H18A C18 H18C 110.00 . . no
H18B C18 H18C 109.00 . . no
C4 C19 H19A 109.00 . . no
C4 C19 H19B 110.00 . . no
C4 C19 H19C 109.00 . . no
H19A C19 H19B 109.00 . . no
H19A C19 H19C 110.00 . . no
H19B C19 H19C 109.00 . . no
C22 C24 H24A 109.00 . . no
C22 C24 H24B 109.00 . . no
C22 C24 H24C 109.00 . . no
H24A C24 H24B 109.00 . . no
H24A C24 H24C 109.00 . . no
H24B C24 H24C 109.00 . . no

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

C13 N1 C2 C3 178.3(2) . . . . ?
C13 N1 C2 C7 0.5(3) . . . . ?
N1 C2 C3 C4 -180.0(2) . . . . ?
C7 C2 C3 C4 -2.5(3) . . . . ?
N1 C2 C3 C14 -2.0(3) . . . . ?
C7 C2 C3 C14 175.5(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C14 C3 C4 C5 -176.9(2) . . . . ?
C2 C3 C4 C19 179.5(2) . . . . ?
C14 C3 C4 C19 1.6(4) . . . . ?
C3 C4 C5 O20 -177.7(2) . . . . ?
C19 C4 C5 O20 3.7(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C19 C4 C5 C6 -177.8(2) . . . . ?
O20 C5 C6 C7 177.3(2) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
O20 C5 C6 N21 -1.3(3) . . . . ?
C4 C5 C6 N21 -179.7(2) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
N21 C6 C7 C2 178.3(2) . . . . ?
C5 C6 C7 C8 179.5(2) . . . . ?
N21 C6 C7 C8 -1.9(4) . . . . ?
N1 C2 C7 C6 -179.9(2) . . . . ?
C3 C2 C7 C6 2.2(3) . . . . ?
N1 C2 C7 C8 0.2(3) . . . . ?
C3 C2 C7 C8 -177.7(2) . . . . ?
C6 C7 C8 C13 179.3(3) . . . . ?
C2 C7 C8 C13 -0.9(3) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C2 C7 C8 C9 179.7(3) . . . . ?
C13 C8 C9 C10 -0.6(4) . . . . ?
C7 C8 C9 C10 178.7(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C2 N1 C13 C12 178.7(2) . . . . ?
C2 N1 C13 C8 -1.1(3) . . . . ?
C11 C12 C13 N1 -180.0(2) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C9 C8 C13 N1 -179.3(2) . . . . ?
C7 C8 C13 N1 1.2(3) . . . . ?
C9 C8 C13 C12 0.9(4) . . . . ?
C7 C8 C13 C12 -178.6(2) . . . . ?
C4 C3 C14 C15 -100.9(3) . . . . ?
C2 C3 C14 C15 81.3(3) . . . . ?
C3 C14 C15 C16 69.0(3) . . . . ?
C14 C15 C16 C17 176.5(2) . . . . ?
C15 C16 C17 C18 -176.5(3) . . . . ?
C5 C6 N21 C22 -49.2(3) . . . . ?
C7 C6 N21 C22 132.2(2) . . . . ?
C6 N21 C22 O23 5.9(4) . . . . ?
C6 N21 C22 C24 -175.2(2) . . . . ?

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 H1 O20 1.07 1.90 2.961(2) 168.6 4_566
O20 H20 O23 1.03 1.64 2.641(2) 161.0 .
N21 H21 O23 0.92 2.23 3.072(3) 151.9 1_455

_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        27.90

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.257

_refine_diff_density_min         -0.248

_refine_diff_density_rms         0.048

_vrf_PLAT220_ca403               
;

PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.30 Ratio

RESPONSE: Structure contains disorderd atoms

;

_vrf_PLAT222_ca403               
;

PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 6.03 Ratio

RESPONSE: Structure contains disorderd atoms

;