# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               'Chemical Science'
_journal_coden_cambridge         1475
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       hiroto@apchem.nagoya-u.ac.jp
_publ_contact_author_name        'Hiroshi Shinokubo'
loop_
_publ_author_name
S.Nakamura
S.Hiroto
H.Shinokubo

data_11419sna
_database_code_depnum_ccdc_archive 'CCDC 836157'
#TrackingRef '6401_web_deposit_cif_file_0_SatoruHiroto_1311299632.11419sna.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H46 Br2 N4 O2'
_chemical_formula_weight         870.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I4(1)/acd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z'
'x, -y, -z+1/2'
'y+1/4, x+3/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1'
'y+3/4, x+5/4, -z+5/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z'
'-x, y, z-1/2'
'-y-1/4, -x-3/4, z-3/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/4, -x-1/4, z-1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   23.2637(17)
_cell_length_b                   23.2637(17)
_cell_length_c                   62.003(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     33556(6)
_cell_formula_units_Z            32
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6880
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      21.52

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             14336
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5886
_exptl_absorpt_correction_T_max  0.9076
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            82951
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -73
_diffrn_reflns_limit_l_max       73
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7392
_reflns_number_gt                4741
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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.
;

_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^)+(0.0541P)^2^+251.7233P] 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         7392
_refine_ls_number_parameters     555
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.2003
_refine_ls_wR_factor_gt          0.1763
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9038(4) 0.4451(4) 0.16705(14) 0.069(2) Uani 0.789(3) 1 d P A 1
Br1 Br 0.97335(4) 0.40640(4) 0.039428(15) 0.0612(4) Uani 0.789(3) 1 d P A 1
O2 O 0.9678(12) 0.3900(12) 0.0523(5) 0.092(9) Uani 0.211(3) 1 d PDU A 2
Br2 Br 0.8967(2) 0.4613(2) 0.17773(8) 0.0642(15) Uani 0.211(3) 1 d P A 2
O1B O 0.6987(4) 0.2390(4) 0.16781(16) 0.062(2) Uani 0.669(3) 1 d P B 1
Br1B Br 0.72707(5) 0.16268(5) 0.04123(2) 0.0585(5) Uani 0.669(3) 1 d P B 1
O2B O 0.7477(8) 0.1811(7) 0.0528(3) 0.078(5) Uani 0.331(3) 1 d PD B 3
Br2B Br 0.68692(11) 0.24597(11) 0.18042(6) 0.0645(10) Uani 0.331(3) 1 d P B 3
C1 C 0.9760(2) 0.3771(2) 0.15436(10) 0.0374(14) Uani 1 1 d . A .
C2 C 0.9292(3) 0.4227(2) 0.15366(10) 0.0402(14) Uani 1 1 d . . .
C3 C 0.9195(3) 0.4328(3) 0.13088(10) 0.0448(15) Uani 1 1 d . A .
C4 C 0.8825(3) 0.4695(3) 0.12066(11) 0.0524(17) Uani 1 1 d . . .
H4 H 0.8579 0.4938 0.1288 0.063 Uiso 1 1 calc R A .
C5 C 0.8813(3) 0.4708(3) 0.09814(12) 0.0560(18) Uani 1 1 d . A .
C6 C 0.9179(3) 0.4346(3) 0.08745(11) 0.0486(16) Uani 1 1 d . . .
H6 H 0.9163 0.4348 0.0721 0.058 Uiso 1 1 calc R A .
C7 C 0.9582(2) 0.3965(2) 0.09733(9) 0.0329(12) Uani 1 1 d . A .
C8 C 0.9571(2) 0.3963(2) 0.11993(10) 0.0370(13) Uani 1 1 d . . .
C9 C 0.9951(2) 0.3621(2) 0.08396(8) 0.0318(12) Uani 1 1 d . . .
C10 C 1.0026(3) 0.3605(2) 0.06149(8) 0.0367(13) Uani 1 1 d D A .
C11 C 1.0433(2) 0.3187(2) 0.05630(9) 0.0364(13) Uani 1 1 d . . .
C12 C 1.0660(3) 0.2994(3) 0.03667(10) 0.0511(17) Uani 1 1 d . A .
H12 H 1.0537 0.3163 0.0235 0.061 Uiso 1 1 calc R . .
C13 C 1.1067(3) 0.2555(3) 0.03640(10) 0.0499(16) Uani 1 1 d . . .
C14 C 1.1244(3) 0.2328(3) 0.05595(10) 0.0463(15) Uani 1 1 d . A .
H14 H 1.1526 0.2032 0.0557 0.056 Uiso 1 1 calc R . .
C15 C 1.1034(2) 0.2509(2) 0.07626(9) 0.0348(13) Uani 1 1 d . . .
C16 C 1.0616(2) 0.2943(2) 0.07578(8) 0.0296(12) Uani 1 1 d . A .
C17 C 0.8402(3) 0.5112(3) 0.08606(12) 0.067(2) Uani 1 1 d . . .
C18 C 0.7787(4) 0.4993(4) 0.09273(15) 0.102(3) Uani 1 1 d . A .
H18A H 0.7685 0.4598 0.0887 0.153 Uiso 1 1 calc R . .
H18B H 0.7529 0.5262 0.0854 0.153 Uiso 1 1 calc R . .
H18C H 0.7750 0.5040 0.1084 0.153 Uiso 1 1 calc R . .
C19 C 0.8555(4) 0.5742(3) 0.09185(15) 0.093(3) Uani 1 1 d . A .
H19A H 0.8549 0.5790 0.1076 0.140 Uiso 1 1 calc R . .
H19B H 0.8273 0.6002 0.0853 0.140 Uiso 1 1 calc R . .
H19C H 0.8939 0.5833 0.0864 0.140 Uiso 1 1 calc R . .
C20 C 0.8439(4) 0.5033(5) 0.06158(13) 0.106(4) Uani 1 1 d . A .
H20A H 0.8821 0.5149 0.0565 0.159 Uiso 1 1 calc R . .
H20B H 0.8146 0.5270 0.0546 0.159 Uiso 1 1 calc R . .
H20C H 0.8375 0.4627 0.0580 0.159 Uiso 1 1 calc R . .
C21 C 1.1311(4) 0.2339(4) 0.01506(12) 0.071(2) Uani 1 1 d . A .
C22 C 1.0809(4) 0.2114(4) 0.00134(13) 0.098(3) Uani 1 1 d . . .
H22A H 1.0946 0.2031 -0.0133 0.146 Uiso 1 1 calc R A .
H22B H 1.0506 0.2406 0.0007 0.146 Uiso 1 1 calc R . .
H22C H 1.0656 0.1762 0.0078 0.146 Uiso 1 1 calc R . .
C23 C 1.1753(4) 0.1876(4) 0.01791(15) 0.108(3) Uani 1 1 d . . .
H23A H 1.2088 0.2034 0.0254 0.161 Uiso 1 1 calc R A .
H23B H 1.1871 0.1731 0.0037 0.161 Uiso 1 1 calc R . .
H23C H 1.1589 0.1561 0.0264 0.161 Uiso 1 1 calc R . .
C24 C 1.1584(5) 0.2845(4) 0.00278(15) 0.125(4) Uani 1 1 d . . .
H24A H 1.1901 0.3004 0.0113 0.187 Uiso 1 1 calc R A .
H24B H 1.1293 0.3143 0.0004 0.187 Uiso 1 1 calc R . .
H24C H 1.1730 0.2709 -0.0111 0.187 Uiso 1 1 calc R . .
C1B C 0.7688(2) 0.1687(2) 0.15521(11) 0.0435(15) Uani 1 1 d . B .
C2B C 0.7239(3) 0.2149(3) 0.15471(12) 0.0522(18) Uani 1 1 d . . .
C3B C 0.7140(3) 0.2269(3) 0.13201(12) 0.0517(17) Uani 1 1 d . B .
C4B C 0.6764(3) 0.2627(3) 0.12235(15) 0.071(2) Uani 1 1 d . . .
H4B H 0.6516 0.2862 0.1307 0.085 Uiso 1 1 calc R B .
C5B C 0.6747(3) 0.2649(4) 0.09967(15) 0.075(2) Uani 1 1 d . B .
C6B C 0.7131(3) 0.2306(3) 0.08854(12) 0.0609(19) Uani 1 1 d . . .
H6B H 0.7134 0.2330 0.0732 0.073 Uiso 1 1 calc R B .
C7B C 0.7518(3) 0.1921(2) 0.09856(11) 0.0429(15) Uani 1 1 d . B .
C8B C 0.7518(3) 0.1911(2) 0.12059(11) 0.0440(15) Uani 1 1 d . . .
C9B C 0.7850(2) 0.1538(2) 0.08472(10) 0.0395(14) Uani 1 1 d . . .
C10B C 0.7793(3) 0.1427(3) 0.06248(10) 0.0459(16) Uani 1 1 d D B .
C11B C 0.8198(3) 0.0990(3) 0.05692(10) 0.0479(16) Uani 1 1 d . . .
C12B C 0.8315(4) 0.0703(4) 0.03772(12) 0.074(2) Uani 1 1 d . B .
H12B H 0.8113 0.0800 0.0249 0.089 Uiso 1 1 calc R . .
C13B C 0.8726(4) 0.0277(4) 0.03738(14) 0.080(2) Uani 1 1 d . . .
C14B C 0.7639(3) 0.1502(4) 0.19393(12) 0.068(2) Uani 1 1 d . B .
H14B H 0.7343 0.1783 0.1944 0.081 Uiso 1 1 calc R . .
C15B C 0.7908(3) 0.1398(3) 0.17398(11) 0.0464(16) Uani 1 1 d . . .
C16B C 0.8485(2) 0.0848(2) 0.07601(9) 0.0383(14) Uani 1 1 d . B .
C17B C 0.6310(5) 0.3038(6) 0.0881(2) 0.129(4) Uani 1 1 d U . .
C18B C 0.5753(5) 0.2953(6) 0.0957(3) 0.186(6) Uani 1 1 d U B .
H18D H 0.5632 0.2558 0.0926 0.279 Uiso 1 1 calc R . .
H18E H 0.5491 0.3222 0.0885 0.279 Uiso 1 1 calc R . .
H18F H 0.5744 0.3018 0.1113 0.279 Uiso 1 1 calc R . .
C19B C 0.6497(5) 0.3671(5) 0.0910(2) 0.151(5) Uani 1 1 d U B .
H19D H 0.6224 0.3923 0.0835 0.227 Uiso 1 1 calc R . .
H19E H 0.6882 0.3724 0.0848 0.227 Uiso 1 1 calc R . .
H19F H 0.6504 0.3766 0.1063 0.227 Uiso 1 1 calc R . .
C20B C 0.6346(7) 0.2977(6) 0.0636(2) 0.191(6) Uani 1 1 d U B .
H20D H 0.6224 0.2590 0.0594 0.286 Uiso 1 1 calc R . .
H20E H 0.6743 0.3042 0.0589 0.286 Uiso 1 1 calc R . .
H20F H 0.6093 0.3262 0.0568 0.286 Uiso 1 1 calc R . .
C21B C 0.8835(7) -0.0045(6) 0.01618(18) 0.150(4) Uani 1 1 d U B .
C22B C 0.8298(7) -0.0353(7) 0.0095(2) 0.216(7) Uani 1 1 d U . .
H22D H 0.8372 -0.0572 -0.0037 0.324 Uiso 1 1 calc R B .
H22E H 0.7992 -0.0072 0.0068 0.324 Uiso 1 1 calc R . .
H22F H 0.8178 -0.0616 0.0210 0.324 Uiso 1 1 calc R . .
C23B C 0.9335(7) -0.0479(5) 0.01843(17) 0.167(5) Uani 1 1 d U . .
H23D H 0.9669 -0.0286 0.0248 0.250 Uiso 1 1 calc R B .
H23E H 0.9438 -0.0627 0.0042 0.250 Uiso 1 1 calc R . .
H23F H 0.9216 -0.0797 0.0277 0.250 Uiso 1 1 calc R . .
C24B C 0.9019(6) 0.0398(6) -0.00149(17) 0.165(5) Uani 1 1 d U . .
H24D H 0.9230 0.0199 -0.0130 0.248 Uiso 1 1 calc R B .
H24E H 0.9267 0.0692 0.0050 0.248 Uiso 1 1 calc R . .
H24F H 0.8676 0.0581 -0.0076 0.248 Uiso 1 1 calc R . .
N2 N 0.99038(18) 0.36271(18) 0.13477(7) 0.0349(11) Uani 1 1 d . A .
H2 H 1.0162 0.3367 0.1312 0.042 Uiso 0.211(3) 1 calc PR . .
N3 N 1.03200(18) 0.32134(18) 0.09228(7) 0.0306(10) Uani 1 1 d . A .
H3 H 1.0361 0.3136 0.1061 0.037 Uiso 0.789(3) 1 calc PR . .
N1B N 0.78488(19) 0.1564(2) 0.13516(8) 0.0390(12) Uani 1 1 d . B .
H1B H 0.8113 0.1312 0.1314 0.047 Uiso 0.331(3) 1 calc PR . .
N2B N 0.82689(18) 0.11834(19) 0.09258(7) 0.0336(11) Uani 1 1 d . B .
H2B H 0.8384 0.1170 0.1061 0.040 Uiso 0.669(3) 1 calc PR . .

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
O1 0.086(6) 0.069(5) 0.051(5) -0.011(4) 0.008(4) 0.035(4)
Br1 0.0764(7) 0.0669(7) 0.0402(5) 0.0171(4) -0.0055(4) 0.0256(5)
O2 0.104(12) 0.092(12) 0.080(12) 0.007(9) 0.000(9) 0.000(9)
Br2 0.064(3) 0.064(3) 0.064(3) -0.002(2) 0.001(2) 0.027(2)
O1B 0.067(6) 0.070(6) 0.049(5) -0.005(5) 0.021(4) 0.016(4)
Br1B 0.0684(8) 0.0618(8) 0.0453(7) 0.0072(6) -0.0182(6) 0.0122(6)
O2B 0.095(13) 0.084(13) 0.054(10) -0.032(10) -0.004(10) -0.001(11)
Br2B 0.0529(16) 0.0611(16) 0.079(2) -0.0178(15) 0.0093(14) 0.0087(11)
C1 0.033(3) 0.028(3) 0.051(4) 0.000(3) 0.009(3) 0.002(3)
C2 0.045(4) 0.031(3) 0.045(4) -0.003(3) 0.019(3) 0.009(3)
C3 0.040(4) 0.035(3) 0.060(4) 0.003(3) 0.011(3) 0.010(3)
C4 0.053(4) 0.043(4) 0.061(4) 0.007(3) 0.009(3) 0.022(3)
C5 0.047(4) 0.050(4) 0.071(5) 0.009(4) 0.003(3) 0.023(3)
C6 0.042(4) 0.051(4) 0.053(4) 0.006(3) 0.001(3) 0.011(3)
C7 0.027(3) 0.025(3) 0.046(3) 0.005(2) 0.001(2) 0.000(2)
C8 0.029(3) 0.022(3) 0.060(4) -0.001(3) 0.001(3) 0.003(2)
C9 0.028(3) 0.028(3) 0.039(3) 0.006(2) -0.004(2) -0.002(2)
C10 0.039(3) 0.039(3) 0.032(3) 0.006(3) -0.008(3) -0.001(3)
C11 0.038(3) 0.037(3) 0.033(3) -0.002(3) 0.003(3) -0.008(3)
C12 0.057(4) 0.059(4) 0.038(3) -0.006(3) 0.004(3) -0.012(4)
C13 0.049(4) 0.049(4) 0.051(4) -0.010(3) 0.017(3) -0.012(3)
C14 0.039(3) 0.046(4) 0.054(4) -0.013(3) 0.007(3) -0.005(3)
C15 0.024(3) 0.033(3) 0.048(3) -0.007(3) 0.008(2) -0.004(2)
C16 0.027(3) 0.030(3) 0.032(3) 0.001(2) -0.001(2) -0.007(2)
C17 0.059(5) 0.073(5) 0.070(5) 0.017(4) 0.003(4) 0.037(4)
C18 0.072(6) 0.112(7) 0.122(8) 0.041(6) -0.016(6) 0.044(6)
C19 0.104(7) 0.065(6) 0.110(7) 0.023(5) -0.001(6) 0.044(5)
C20 0.118(8) 0.130(8) 0.069(6) 0.026(6) -0.007(5) 0.074(7)
C21 0.074(5) 0.080(6) 0.059(4) -0.031(4) 0.030(4) -0.011(4)
C22 0.097(7) 0.137(9) 0.058(5) -0.043(5) 0.018(5) -0.023(6)
C23 0.101(7) 0.133(9) 0.089(7) -0.040(6) 0.037(6) 0.025(7)
C24 0.158(10) 0.142(9) 0.075(6) -0.032(6) 0.074(7) -0.060(8)
C1B 0.029(3) 0.034(3) 0.068(4) -0.006(3) 0.002(3) -0.007(3)
C2B 0.042(4) 0.042(4) 0.072(5) -0.023(4) 0.023(4) -0.009(3)
C3B 0.041(4) 0.038(4) 0.076(5) -0.009(3) 0.013(3) -0.004(3)
C4B 0.046(4) 0.057(5) 0.109(7) -0.014(5) 0.011(4) 0.017(4)
C5B 0.065(5) 0.071(6) 0.090(6) -0.005(5) -0.019(5) 0.023(4)
C6B 0.057(4) 0.053(4) 0.074(5) -0.006(4) -0.007(4) 0.011(4)
C7B 0.035(3) 0.031(3) 0.063(4) 0.005(3) 0.005(3) -0.006(3)
C8B 0.033(3) 0.029(3) 0.070(4) 0.000(3) 0.007(3) -0.001(3)
C9B 0.031(3) 0.036(3) 0.052(4) 0.011(3) 0.001(3) -0.003(3)
C10B 0.033(3) 0.063(4) 0.042(4) 0.013(3) -0.007(3) -0.005(3)
C11B 0.046(4) 0.057(4) 0.041(4) -0.007(3) 0.005(3) -0.013(3)
C12B 0.080(6) 0.098(7) 0.043(4) -0.007(4) -0.004(4) -0.029(5)
C13B 0.095(7) 0.077(6) 0.066(6) -0.024(5) 0.020(5) -0.003(5)
C14B 0.056(5) 0.089(6) 0.058(5) -0.021(4) 0.015(4) -0.007(4)
C15B 0.037(4) 0.041(4) 0.061(4) -0.017(3) 0.013(3) -0.007(3)
C16B 0.035(3) 0.038(3) 0.043(3) -0.007(3) 0.000(3) -0.015(3)
C17B 0.112(7) 0.133(8) 0.144(8) 0.002(7) -0.021(7) 0.090(7)
C18B 0.084(8) 0.199(12) 0.276(14) 0.100(11) -0.021(9) 0.044(9)
C19B 0.152(10) 0.127(9) 0.175(11) 0.041(9) -0.037(8) 0.079(8)
C20B 0.211(12) 0.206(12) 0.154(11) -0.016(10) -0.071(10) 0.138(10)
C21B 0.229(12) 0.150(9) 0.070(6) -0.062(6) 0.024(7) -0.008(9)
C22B 0.262(16) 0.229(14) 0.157(11) -0.149(10) 0.008(11) -0.044(12)
C23B 0.258(14) 0.142(10) 0.100(8) -0.068(7) 0.068(9) 0.034(10)
C24B 0.255(14) 0.182(12) 0.058(6) -0.041(7) 0.035(8) 0.019(11)
N2 0.029(2) 0.024(2) 0.052(3) 0.003(2) 0.002(2) 0.005(2)
N3 0.029(2) 0.032(2) 0.031(2) 0.0021(19) -0.0038(19) 0.000(2)
N1B 0.032(3) 0.033(3) 0.052(3) -0.003(2) 0.006(2) -0.004(2)
N2B 0.029(2) 0.033(3) 0.039(3) -0.002(2) 0.002(2) -0.004(2)

_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 C2 1.145(10) . ?
Br1 C10 1.863(5) . ?
O2 C10 1.206(18) . ?
Br2 C2 1.898(7) . ?
O1B C2B 1.149(11) . ?
Br1B C10B 1.852(6) . ?
O2B C10B 1.304(15) . ?
Br2B C2B 1.951(7) . ?
C1 N2 1.304(7) . ?
C1 C15 1.443(8) 15_534 ?
C1 C2 1.520(8) . ?
C2 C3 1.450(8) . ?
C3 C4 1.367(8) . ?
C3 C8 1.396(8) . ?
C4 C5 1.397(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(9) . ?
C5 C17 1.535(9) . ?
C6 C7 1.430(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(8) . ?
C7 C9 1.437(7) . ?
C8 N2 1.434(7) . ?
C9 N3 1.378(6) . ?
C9 C10 1.404(7) . ?
C10 C11 1.395(8) . ?
C11 C12 1.401(8) . ?
C11 C16 1.402(7) . ?
C12 C13 1.393(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(9) . ?
C13 C21 1.524(9) . ?
C14 C15 1.415(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.402(7) . ?
C15 C1 1.443(8) 15_534 ?
C16 N3 1.385(7) . ?
C17 C18 1.515(11) . ?
C17 C20 1.531(11) . ?
C17 C19 1.550(11) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.499(12) . ?
C21 C22 1.537(11) . ?
C21 C24 1.538(11) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C1B N1B 1.329(8) . ?
C1B C15B 1.438(9) . ?
C1B C2B 1.499(9) . ?
C2B C3B 1.453(10) . ?
C3B C4B 1.348(10) . ?
C3B C8B 1.402(8) . ?
C4B C5B 1.408(11) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.383(10) . ?
C5B C17B 1.540(12) . ?
C6B C7B 1.414(9) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.366(9) . ?
C7B C9B 1.459(8) . ?
C8B N1B 1.435(8) . ?
C9B N2B 1.366(7) . ?
C9B C10B 1.408(8) . ?
C10B C11B 1.428(9) . ?
C11B C12B 1.393(9) . ?
C11B C16B 1.399(8) . ?
C12B C13B 1.376(12) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.364(11) 15_534 ?
C13B C21B 1.533(12) . ?
C14B C13B 1.364(11) 15_534 ?
C14B C15B 1.407(9) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.404(8) 15_534 ?
C16B N2B 1.384(7) . ?
C16B C15B 1.404(8) 15_534 ?
C17B C18B 1.393(16) . ?
C17B C20B 1.528(16) . ?
C17B C19B 1.546(17) . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B C22B 1.500(19) . ?
C21B C23B 1.546(19) . ?
C21B C24B 1.564(17) . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
N2 H2 0.8800 . ?
N3 H3 0.8800 . ?
N1B H1B 0.8800 . ?
N2B H2B 0.8800 . ?

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
N2 C1 C15 125.1(5) . 15_534 ?
N2 C1 C2 109.7(5) . . ?
C15 C1 C2 125.3(5) 15_534 . ?
O1 C2 C3 123.5(6) . . ?
O1 C2 C1 131.8(6) . . ?
C3 C2 C1 104.7(5) . . ?
O1 C2 Br2 7.7(5) . . ?
C3 C2 Br2 128.8(4) . . ?
C1 C2 Br2 126.3(5) . . ?
C4 C3 C8 123.2(6) . . ?
C4 C3 C2 130.7(6) . . ?
C8 C3 C2 106.1(5) . . ?
C3 C4 C5 119.4(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 117.2(6) . . ?
C6 C5 C17 121.8(6) . . ?
C4 C5 C17 121.0(6) . . ?
C5 C6 C7 125.6(6) . . ?
C5 C6 H6 117.2 . . ?
C7 C6 H6 117.2 . . ?
C8 C7 C6 114.7(5) . . ?
C8 C7 C9 125.9(5) . . ?
C6 C7 C9 119.4(5) . . ?
C3 C8 C7 119.8(5) . . ?
C3 C8 N2 111.0(5) . . ?
C7 C8 N2 129.3(5) . . ?
N3 C9 C10 106.1(5) . . ?
N3 C9 C7 122.6(5) . . ?
C10 C9 C7 131.3(5) . . ?
O2 C10 C11 138.0(17) . . ?
O2 C10 C9 111.9(18) . . ?
C11 C10 C9 109.3(5) . . ?
O2 C10 Br1 23.2(17) . . ?
C11 C10 Br1 118.5(4) . . ?
C9 C10 Br1 132.0(4) . . ?
C10 C11 C12 132.9(6) . . ?
C10 C11 C16 106.9(5) . . ?
C12 C11 C16 120.2(5) . . ?
C13 C12 C11 120.2(6) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 118.1(6) . . ?
C14 C13 C21 121.6(6) . . ?
C12 C13 C21 120.3(6) . . ?
C13 C14 C15 124.3(6) . . ?
C13 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C16 C15 C14 115.8(5) . . ?
C16 C15 C1 124.8(5) . 15_534 ?
C14 C15 C1 119.3(5) . 15_534 ?
N3 C16 C11 107.5(4) . . ?
N3 C16 C15 131.1(5) . . ?
C11 C16 C15 121.5(5) . . ?
C18 C17 C20 107.6(8) . . ?
C18 C17 C5 110.0(6) . . ?
C20 C17 C5 112.0(6) . . ?
C18 C17 C19 109.1(7) . . ?
C20 C17 C19 109.4(7) . . ?
C5 C17 C19 108.9(7) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C21 C13 112.9(7) . . ?
C23 C21 C22 110.0(7) . . ?
C13 C21 C22 108.0(6) . . ?
C23 C21 C24 109.0(8) . . ?
C13 C21 C24 109.4(6) . . ?
C22 C21 C24 107.4(8) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1B C1B C15B 123.8(5) . . ?
N1B C1B C2B 109.3(6) . . ?
C15B C1B C2B 126.8(6) . . ?
O1B C2B C3B 120.7(7) . . ?
O1B C2B C1B 133.8(8) . . ?
C3B C2B C1B 105.6(5) . . ?
O1B C2B Br2B 10.1(5) . . ?
C3B C2B Br2B 130.5(5) . . ?
C1B C2B Br2B 123.8(5) . . ?
C4B C3B C8B 123.3(7) . . ?
C4B C3B C2B 130.7(7) . . ?
C8B C3B C2B 106.0(6) . . ?
C3B C4B C5B 119.0(7) . . ?
C3B C4B H4B 120.5 . . ?
C5B C4B H4B 120.5 . . ?
C6B C5B C4B 117.3(7) . . ?
C6B C5B C17B 122.2(8) . . ?
C4B C5B C17B 120.5(8) . . ?
C5B C6B C7B 123.9(7) . . ?
C5B C6B H6B 118.0 . . ?
C7B C6B H6B 118.0 . . ?
C8B C7B C6B 116.7(6) . . ?
C8B C7B C9B 125.3(6) . . ?
C6B C7B C9B 117.8(6) . . ?
C7B C8B C3B 119.7(6) . . ?
C7B C8B N1B 129.7(5) . . ?
C3B C8B N1B 110.6(6) . . ?
N2B C9B C10B 107.9(5) . . ?
N2B C9B C7B 122.4(5) . . ?
C10B C9B C7B 129.6(6) . . ?
O2B C10B C9B 112.4(10) . . ?
O2B C10B C11B 138.3(9) . . ?
C9B C10B C11B 107.7(5) . . ?
O2B C10B Br1B 29.5(8) . . ?
C9B C10B Br1B 135.4(5) . . ?
C11B C10B Br1B 116.0(5) . . ?
C12B C11B C16B 121.1(7) . . ?
C12B C11B C10B 132.7(7) . . ?
C16B C11B C10B 106.2(5) . . ?
C13B C12B C11B 119.7(7) . . ?
C13B C12B H12B 120.2 . . ?
C11B C12B H12B 120.2 . . ?
C14B C13B C12B 118.9(7) 15_534 . ?
C14B C13B C21B 122.4(10) 15_534 . ?
C12B C13B C21B 118.7(10) . . ?
C13B C14B C15B 124.2(8) 15_534 . ?
C13B C14B H14B 117.9 15_534 . ?
C15B C14B H14B 117.9 . . ?
C16B C15B C14B 116.2(7) 15_534 . ?
C16B C15B C1B 125.4(5) 15_534 . ?
C14B C15B C1B 118.2(6) . . ?
N2B C16B C11B 108.8(5) . . ?
N2B C16B C15B 131.2(5) . 15_534 ?
C11B C16B C15B 120.0(6) . 15_534 ?
C18B C17B C20B 112.0(13) . . ?
C18B C17B C5B 111.8(11) . . ?
C20B C17B C5B 112.0(9) . . ?
C18B C17B C19B 111.0(11) . . ?
C20B C17B C19B 100.8(12) . . ?
C5B C17B C19B 108.6(10) . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C17B C19B H19D 109.5 . . ?
C17B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C17B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C17B C20B H20D 109.5 . . ?
C17B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C17B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C22B C21B C13B 109.4(11) . . ?
C22B C21B C23B 109.9(12) . . ?
C13B C21B C23B 111.5(11) . . ?
C22B C21B C24B 110.4(13) . . ?
C13B C21B C24B 109.0(10) . . ?
C23B C21B C24B 106.7(12) . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C21B C23B H23D 109.5 . . ?
C21B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C21B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C21B C24B H24D 109.5 . . ?
C21B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C21B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C1 N2 C8 108.6(4) . . ?
C1 N2 H2 125.7 . . ?
C8 N2 H2 125.7 . . ?
C9 N3 C16 110.2(4) . . ?
C9 N3 H3 124.9 . . ?
C16 N3 H3 124.9 . . ?
C1B N1B C8B 108.5(5) . . ?
C1B N1B H1B 125.8 . . ?
C8B N1B H1B 125.8 . . ?
C9B N2B C16B 109.5(5) . . ?
C9B N2B H2B 125.2 . . ?
C16B N2B H2B 125.2 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.075

# Attachment '6402_web_deposit_cif_file_1_SatoruHiroto_1311299632.0902NAK.cif'

data_0902nak
_database_code_depnum_ccdc_archive 'CCDC 836158'
#TrackingRef '6402_web_deposit_cif_file_1_SatoruHiroto_1311299632.0902NAK.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H52 N4 O2'
_chemical_formula_weight         789.00

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           Tetragonal
_symmetry_space_group_name_H-M   I-4c2

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

_cell_length_a                   17.198(4)
_cell_length_b                   17.198(4)
_cell_length_c                   15.807(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4675(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    861
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      19.92

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9865
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6057
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1885
_reflns_number_gt                1330
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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.
;

_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^)+(0.1325P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(5)
_refine_ls_number_reflns         1885
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.2068
_refine_ls_wR_factor_gt          0.1881
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.3241(3) 0.0425(3) 0.2424(3) 0.0566(12) Uani 1 1 d . . .
C2 C 0.2782(3) 0.0948(3) 0.2815(3) 0.0633(14) Uani 1 1 d . . .
H2 H 0.2241 0.0897 0.2921 0.076 Uiso 1 1 calc R . .
C3 C 0.3267(3) 0.1605(3) 0.3046(3) 0.0601(13) Uani 1 1 d . . .
C4 C 0.3139(2) 0.2303(3) 0.3457(3) 0.0658(15) Uani 1 1 d . . .
H4 H 0.2627 0.2429 0.3636 0.079 Uiso 1 1 calc R . .
C5 C 0.3732(2) 0.2822(3) 0.3614(3) 0.0574(13) Uani 1 1 d . . .
C6 C 0.4481(2) 0.2625(3) 0.3331(3) 0.0632(14) Uani 1 1 d . . .
H6 H 0.4895 0.2977 0.3438 0.076 Uiso 1 1 calc R . .
C7 C 0.4648(2) 0.1929(3) 0.2895(3) 0.0531(12) Uani 1 1 d . . .
C8 C 0.4015(2) 0.1433(3) 0.2778(3) 0.0518(11) Uani 1 1 d . . .
C9 C 0.3605(3) 0.3575(3) 0.4114(3) 0.0633(14) Uani 1 1 d . . .
C10 C 0.3901(4) 0.3448(4) 0.4998(5) 0.120(3) Uani 1 1 d . . .
H10A H 0.3853 0.3932 0.5321 0.180 Uiso 1 1 calc R . .
H10B H 0.4449 0.3290 0.4976 0.180 Uiso 1 1 calc R . .
H10C H 0.3595 0.3039 0.5272 0.180 Uiso 1 1 calc R . .
C11 C 0.2759(3) 0.3811(3) 0.4172(5) 0.088(2) Uani 1 1 d . . .
H11A H 0.2552 0.3895 0.3602 0.131 Uiso 1 1 calc R . .
H11B H 0.2715 0.4293 0.4499 0.131 Uiso 1 1 calc R . .
H11C H 0.2462 0.3399 0.4452 0.131 Uiso 1 1 calc R . .
C12 C 0.4044(5) 0.4251(4) 0.3716(7) 0.137(4) Uani 1 1 d . . .
H12A H 0.3805 0.4384 0.3172 0.206 Uiso 1 1 calc R . .
H12B H 0.4587 0.4102 0.3627 0.206 Uiso 1 1 calc R . .
H12C H 0.4021 0.4702 0.4094 0.206 Uiso 1 1 calc R . .
N1 N 0.3993(2) 0.0695(2) 0.2395(2) 0.0560(10) Uani 1 1 d . . .
H1 H 0.4392 0.0448 0.2174 0.067 Uiso 1 1 calc R . .
O1 O 0.4758(2) -0.0125(3) 0.1087(3) 0.0310(12) Uani 0.50 1 d P . .
C20 C 0.5251(8) 0.1290(6) 0.0308(8) 0.061(3) Uani 0.50 1 d P A 2
C15 C 0.5573(5) 0.0516(4) 0.0560(4) 0.0404(18) Uani 0.50 1 d P . .
C23 C 0.5224(7) 0.1321(6) -0.0161(8) 0.056(3) Uani 0.50 1 d P A 1

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
C1 0.054(3) 0.060(3) 0.056(3) -0.015(2) -0.021(2) 0.001(2)
C2 0.048(2) 0.063(3) 0.079(3) -0.021(3) -0.021(2) -0.003(2)
C3 0.051(3) 0.065(3) 0.064(3) -0.029(2) -0.010(2) 0.001(2)
C4 0.043(2) 0.082(4) 0.073(4) -0.031(3) -0.002(2) -0.001(2)
C5 0.041(2) 0.069(3) 0.062(3) -0.036(3) -0.002(2) 0.002(2)
C6 0.043(2) 0.074(3) 0.073(3) -0.033(3) 0.002(2) -0.005(2)
C7 0.046(2) 0.065(3) 0.049(3) -0.021(2) 0.007(2) 0.0016(19)
C8 0.053(2) 0.060(3) 0.043(2) -0.022(2) -0.006(2) 0.001(2)
C9 0.045(3) 0.070(3) 0.075(3) -0.039(3) -0.003(2) 0.009(2)
C10 0.129(6) 0.121(6) 0.111(5) -0.086(5) -0.054(5) 0.058(4)
C11 0.062(3) 0.074(3) 0.127(6) -0.040(4) -0.015(3) 0.020(3)
C12 0.140(6) 0.075(4) 0.196(9) -0.069(5) 0.088(7) -0.039(4)
N1 0.057(2) 0.060(2) 0.051(2) -0.025(2) -0.0098(17) 0.0043(18)
O1 0.028(3) 0.039(3) 0.027(2) -0.001(2) -0.0015(19) -0.001(2)
C20 0.117(9) 0.034(5) 0.031(6) 0.001(6) -0.018(7) 0.006(5)
C15 0.059(5) 0.046(5) 0.016(4) -0.001(3) -0.004(4) -0.019(4)
C23 0.113(9) 0.028(5) 0.026(6) -0.007(5) 0.003(6) -0.013(5)

_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 1.347(6) . ?
C1 N1 1.375(6) . ?
C1 C7 1.458(6) 12_545 ?
C2 C3 1.450(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(6) . ?
C3 C8 1.387(6) . ?
C4 C5 1.377(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(6) . ?
C5 C9 1.532(6) . ?
C6 C7 1.411(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(6) . ?
C7 C1 1.458(6) 11 ?
C8 N1 1.406(5) . ?
C9 C10 1.503(9) . ?
C9 C11 1.514(7) . ?
C9 C12 1.521(9) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 H1 0.8800 . ?
O1 O1 0.936(8) 2_655 ?
O1 C15 1.213(7) 2_655 ?
C20 C15 1.496(14) . ?
C20 C15 1.900(14) 15_544 ?
C15 O1 1.213(7) 2_655 ?
C15 C23 1.518(14) 15_544 ?
C15 C15 1.776(13) 15_544 ?
C15 C23 1.892(15) . ?
C15 C20 1.900(15) 15_544 ?
C23 C15 1.518(14) 15_544 ?

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 N1 109.9(4) . . ?
C2 C1 C7 130.9(4) . 12_545 ?
N1 C1 C7 119.1(4) . 12_545 ?
C1 C2 C3 107.4(4) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
C4 C3 C8 118.5(4) . . ?
C4 C3 C2 134.7(4) . . ?
C8 C3 C2 106.9(4) . . ?
C5 C4 C3 121.9(4) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 C9 122.3(4) . . ?
C6 C5 C9 119.9(4) . . ?
C5 C6 C7 123.1(4) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C8 C7 C6 115.2(4) . . ?
C8 C7 C1 123.1(4) . 11 ?
C6 C7 C1 121.7(4) . 11 ?
C3 C8 C7 123.6(4) . . ?
C3 C8 N1 107.4(4) . . ?
C7 C8 N1 129.1(4) . . ?
C10 C9 C11 108.0(5) . . ?
C10 C9 C12 109.1(6) . . ?
C11 C9 C12 107.2(5) . . ?
C10 C9 C5 108.0(4) . . ?
C11 C9 C5 113.3(4) . . ?
C12 C9 C5 111.2(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C8 108.5(3) . . ?
C1 N1 H1 125.8 . . ?
C8 N1 H1 125.8 . . ?
O1 O1 C15 132.2(5) 2_655 2_655 ?
C15 C20 C15 61.7(6) . 15_544 ?
O1 C15 C20 120.1(8) 2_655 . ?
O1 C15 C23 120.0(8) 2_655 15_544 ?
C20 C15 C23 119.9(6) . 15_544 ?
O1 C15 C15 133.6(4) 2_655 15_544 ?
C20 C15 C15 70.4(7) . 15_544 ?
C23 C15 C15 69.6(7) 15_544 15_544 ?
O1 C15 C23 132.1(7) 2_655 . ?
C20 C15 C23 21.6(5) . . ?
C23 C15 C23 105.1(8) 15_544 . ?
C15 C15 C23 48.8(5) 15_544 . ?
O1 C15 C20 131.9(7) 2_655 15_544 ?
C20 C15 C20 105.1(8) . 15_544 ?
C23 C15 C20 21.7(5) 15_544 15_544 ?
C15 C15 C20 47.9(5) 15_544 15_544 ?
C23 C15 C20 86.9(4) . 15_544 ?
C15 C23 C15 61.6(6) 15_544 . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.052