# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Geoff Zhang'
_publ_contact_author_email       GEOFF.GZ.ZHANG@ABBOTT.COM

_publ_section_title              
;
Chiral Co-Crystal Solid Solution: Structures,
Melting Point Phase Diagram, and Chiral Enrichment of
(Ibuprofen)2(4,4-Dipyridyl)
;
loop_
_publ_author_name
'Geoff Zhang'
'Shuang Chen'
'Rodger F Henry'
'Ian Marsden'
'Hanmi Xi'

# Attachment 'x489n_SS-1to1.cif'

data_x489n
_database_code_depnum_ccdc_archive 'CCDC 734643'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N O2'
_chemical_formula_weight         280.33

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           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.721(3)
_cell_length_b                   11.617(5)
_cell_length_c                   24.595(11)
_cell_angle_alpha                93.910(8)
_cell_angle_beta                 90.624(8)
_cell_angle_gamma                103.852(8)
_cell_volume                     1582.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17733
_diffrn_reflns_av_R_equivalents  0.1307
_diffrn_reflns_av_sigmaI/netI    0.1281
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         0.83
_diffrn_reflns_theta_max         28.09
_reflns_number_total             13760
_reflns_number_gt                5889
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1965P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_number_reflns         13760
_refine_ls_number_parameters     863
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1779
_refine_ls_R_factor_gt           0.1060
_refine_ls_wR_factor_ref         0.3283
_refine_ls_wR_factor_gt          0.2748
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          3.602
_refine_ls_shift/su_mean         0.120

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
C70 C 0.9725(11) 0.9787(5) 1.0186(3) 0.0422(15) Uani 1 1 d . B .
C55 C -0.0782(11) 0.5752(5) 1.0569(3) 0.0419(15) Uani 1 1 d . . .
O1 O -0.5404(9) 0.9382(5) 1.1534(2) 0.0666(15) Uani 1 1 d . . .
O2 O -0.2285(9) 0.9168(4) 1.2011(2) 0.0599(14) Uani 1 1 d . . .
C1 C -0.4080(14) 0.9597(6) 1.1947(3) 0.0521(18) Uani 1 1 d . . .
C2 C -0.4318(17) 1.0467(8) 1.2419(4) 0.064(2) Uani 1 1 d . . .
H2 H -0.269(16) 1.094(8) 1.252(3) 0.077 Uiso 1 1 calc . . .
C3 C -0.5762(17) 1.1303(8) 1.2287(4) 0.080(3) Uani 1 1 d . . .
H3A H -0.5865 1.1813 1.2606 0.120 Uiso 1 1 calc R . .
H3B H -0.7351 1.0868 1.2168 0.120 Uiso 1 1 calc R . .
H3C H -0.5016 1.1775 1.2002 0.120 Uiso 1 1 calc R . .
C4 C -0.5268(13) 0.9757(5) 1.2908(3) 0.0504(17) Uani 1 1 d . . .
C5 C -0.3846(14) 0.9743(6) 1.3346(3) 0.0585(19) Uani 1 1 d . . .
H5 H -0.2238 1.0154 1.3344 0.070 Uiso 1 1 calc R . .
C6 C -0.4678(16) 0.9144(8) 1.3798(3) 0.067(2) Uani 1 1 d . . .
H6 H -0.3612 0.9137 1.4085 0.081 Uiso 1 1 calc R . .
C7 C -0.7004(16) 0.8571(7) 1.3829(3) 0.0581(19) Uani 1 1 d . . .
C8 C -0.8527(13) 0.8536(6) 1.3382(4) 0.065(2) Uani 1 1 d . . .
H8 H -1.0120 0.8104 1.3385 0.078 Uiso 1 1 calc R . .
C9 C -0.7666(17) 0.9154(7) 1.2923(4) 0.069(2) Uani 1 1 d . . .
H9 H -0.8707 0.9156 1.2630 0.083 Uiso 1 1 calc R . .
C10 C -0.800(2) 0.7959(7) 1.4336(4) 0.083(3) Uani 1 1 d . A .
H10A H -0.9585 0.8093 1.4404 0.099 Uiso 1 1 calc R . .
H10B H -0.6958 0.8303 1.4648 0.099 Uiso 1 1 calc R . .
C11 C -0.818(3) 0.6579(14) 1.4264(7) 0.135(5) Uiso 1 1 d . . .
C12 C -0.919(6) 0.608(3) 1.4886(12) 0.131(9) Uiso 0.576(10) 1 d P A 1
C13 C -0.735(6) 0.631(3) 1.4955(11) 0.174(10) Uiso 0.576(10) 1 d P A 1
C12' C -0.639(7) 0.613(3) 1.4042(15) 0.128(11) Uiso 0.424(10) 1 d P A 2
C13' C -1.001(5) 0.584(2) 1.4651(13) 0.100(8) Uiso 0.424(10) 1 d P A 2
C13A C -0.562(4) 0.6384(19) 1.4248(8) 0.185(9) Uiso 1 1 d . A .
C12A C -0.878(7) 0.596(4) 1.3904(14) 0.40(2) Uiso 1 1 d . A .
O3 O 0.4604(10) 1.4480(5) 1.1550(2) 0.0654(15) Uani 1 1 d . . .
O4 O 0.7854(8) 1.4274(4) 1.19910(19) 0.0496(12) Uani 1 1 d . . .
C14 C 0.5972(12) 1.4683(6) 1.1957(3) 0.0495(17) Uani 1 1 d . . .
C15 C 0.5637(18) 1.5349(7) 1.2480(4) 0.065(2) Uani 1 1 d . . .
H15 H 0.723(16) 1.582(7) 1.261(4) 0.078 Uiso 1 1 calc . . .
C16 C 0.4071(17) 1.6218(7) 1.2380(4) 0.078(3) Uani 1 1 d . . .
H16A H 0.2436 1.5782 1.2306 0.117 Uiso 1 1 calc R . .
H16B H 0.4656 1.6662 1.2074 0.117 Uiso 1 1 calc R . .
H16C H 0.4140 1.6754 1.2698 0.117 Uiso 1 1 calc R . .
C17 C 0.4740(13) 1.4472(6) 1.2904(3) 0.0498(17) Uani 1 1 d . . .
C18 C 0.6366(14) 1.4295(7) 1.3262(3) 0.063(2) Uani 1 1 d . . .
H18 H 0.7943 1.4752 1.3268 0.075 Uiso 1 1 calc R . .
C19 C 0.5654(14) 1.3395(7) 1.3634(3) 0.063(2) Uani 1 1 d . . .
H19 H 0.6800 1.3225 1.3866 0.076 Uiso 1 1 calc R . .
C20 C 0.3351(15) 1.2792(6) 1.3652(3) 0.0562(19) Uani 1 1 d . A .
C21 C 0.1704(13) 1.3030(8) 1.3288(4) 0.067(2) Uani 1 1 d . . .
H21 H 0.0094 1.2625 1.3298 0.080 Uiso 1 1 calc R . .
C22 C 0.2403(14) 1.3847(7) 1.2914(3) 0.061(2) Uani 1 1 d . . .
H22 H 0.1279 1.3979 1.2665 0.074 Uiso 1 1 calc R . .
C23 C 0.263(2) 1.1813(8) 1.4055(3) 0.077(3) Uani 1 1 d . . .
H23A H 0.1030 1.1345 1.3948 0.092 Uiso 1 1 calc R A 1
H23B H 0.3718 1.1290 1.4009 0.092 Uiso 1 1 calc R A 1
C24 C 0.261(3) 1.2175(13) 1.4646(6) 0.063(3) Uiso 0.576(10) 1 d P A 1
C25 C 0.391(3) 1.3187(18) 1.4908(8) 0.104(6) Uiso 0.576(10) 1 d P A 1
C26 C 0.109(7) 1.098(3) 1.4916(12) 0.171(11) Uiso 0.576(10) 1 d P A 1
C24' C 0.160(5) 1.256(2) 1.4603(10) 0.081(6) Uiso 0.424(10) 1 d P A 2
C25' C 0.027(7) 1.261(3) 1.4727(14) 0.114(9) Uiso 0.424(10) 1 d P A 2
C26' C 0.257(3) 1.1118(15) 1.4995(7) 0.056(4) Uiso 0.424(10) 1 d P A 2
C25A C 0.140(18) 1.245(7) 1.481(3) 0.82(7) Uiso 1 1 d . . .
O5 O 0.1403(11) 0.1419(5) 0.8731(2) 0.0679(16) Uani 1 1 d . B .
O6 O 0.4458(11) 0.1201(5) 0.9237(2) 0.0667(15) Uani 1 1 d . B .
C27 C 0.3354(16) 0.1002(6) 0.8832(3) 0.059(2) Uani 1 1 d . . .
C28 C 0.460(3) 0.0368(13) 0.8391(6) 0.048(4) Uani 0.477(12) 1 d P B 1
H28 H 0.62(2) 0.033(11) 0.851(5) 0.057 Uiso 0.48 1 calc P B 1
C29 C 0.291(4) -0.0853(11) 0.8330(6) 0.068(5) Uani 0.477(12) 1 d P B 1
H29A H 0.3509 -0.1343 0.8062 0.103 Uiso 0.477(12) 1 calc PR B 1
H29B H 0.1342 -0.0787 0.8216 0.103 Uiso 0.477(12) 1 calc PR B 1
H29C H 0.2808 -0.1206 0.8673 0.103 Uiso 0.477(12) 1 calc PR B 1
C28' C 0.326(3) 0.0069(9) 0.8340(5) 0.032(3) Uani 0.523(12) 1 d P B 2
H28' H 0.16(2) -0.037(11) 0.823(5) 0.039 Uiso 0.52 1 calc P B 2
C29' C 0.492(3) -0.0731(9) 0.8495(5) 0.043(4) Uani 0.523(12) 1 d P B 2
H29D H 0.4309 -0.1139 0.8809 0.064 Uiso 0.523(12) 1 calc PR B 2
H29E H 0.6513 -0.0251 0.8576 0.064 Uiso 0.523(12) 1 calc PR B 2
H29F H 0.4959 -0.1301 0.8196 0.064 Uiso 0.523(12) 1 calc PR B 2
C30 C 0.466(2) 0.0898(8) 0.7867(3) 0.078(3) Uani 1 1 d . . .
C31 C 0.3007(18) 0.0901(8) 0.7450(4) 0.079(3) Uani 1 1 d . B .
H31 H 0.1389 0.0531 0.7483 0.095 Uiso 1 1 calc R . .
C32 C 0.3789(18) 0.1455(7) 0.6988(3) 0.072(2) Uani 1 1 d . . .
H32 H 0.2697 0.1410 0.6700 0.087 Uiso 1 1 calc R B .
C33 C 0.6224(18) 0.2099(7) 0.6935(3) 0.069(2) Uani 1 1 d . A .
C34 C 0.7713(19) 0.2094(9) 0.7360(4) 0.084(3) Uani 1 1 d . . .
H34 H 0.9311 0.2515 0.7347 0.101 Uiso 1 1 calc R B .
C35 C 0.697(2) 0.1490(8) 0.7815(4) 0.078(3) Uani 1 1 d . B .
H35 H 0.8084 0.1490 0.8093 0.094 Uiso 1 1 calc R . .
C36 C 0.705(2) 0.2730(8) 0.6438(4) 0.087(3) Uani 1 1 d . . .
H36A H 0.8533 0.2538 0.6323 0.105 Uiso 1 1 calc R A 1
H36B H 0.5850 0.2440 0.6147 0.105 Uiso 1 1 calc R A 1
C37 C 0.744(4) 0.4009(9) 0.6518(5) 0.077(5) Uani 0.576(10) 1 d P A 1
C38 C 0.580(6) 0.4459(13) 0.6666(7) 0.182(15) Uani 0.576(10) 1 d P A 1
C39 C 0.803(9) 0.427(3) 0.586(2) 0.29(3) Uani 0.576(10) 1 d P A 1
C37' C 0.556(6) 0.391(3) 0.6381(13) 0.164(19) Uani 0.424(10) 1 d P A 2
C38' C 0.914(6) 0.461(2) 0.6039(10) 0.133(15) Uani 0.424(10) 1 d P A 2
O7 O 1.1225(10) 0.6304(5) 0.8750(2) 0.0638(14) Uani 1 1 d . B .
O8 O 1.4416(10) 0.6085(5) 0.9212(2) 0.0631(14) Uani 1 1 d . B .
C40 C 1.3238(16) 0.5934(6) 0.8814(3) 0.058(2) Uani 1 1 d . . .
C41 C 1.444(3) 0.5340(16) 0.8327(7) 0.053(4) Uani 0.523(12) 1 d P B 1
H41 H 1.61(2) 0.528(11) 0.843(5) 0.064 Uiso 0.52 1 calc P B 1
C42 C 1.288(4) 0.4198(10) 0.8177(6) 0.089(6) Uani 0.523(12) 1 d P B 1
H42A H 1.3438 0.3864 0.7849 0.134 Uiso 0.523(12) 1 calc PR B 1
H42B H 1.1275 0.4283 0.8114 0.134 Uiso 0.523(12) 1 calc PR B 1
H42C H 1.2889 0.3682 0.8465 0.134 Uiso 0.523(12) 1 calc PR B 1
C41' C 1.329(2) 0.5124(13) 0.8281(7) 0.033(3) Uani 0.477(12) 1 d P B 2
H41' H 1.17(2) 0.465(13) 0.816(6) 0.040 Uiso 0.48 1 calc P B 2
C42' C 1.513(3) 0.4350(11) 0.8349(6) 0.048(4) Uani 0.477(12) 1 d P B 2
H42D H 1.6675 0.4854 0.8462 0.071 Uiso 0.477(12) 1 calc PR B 2
H42E H 1.5279 0.3924 0.8008 0.071 Uiso 0.477(12) 1 calc PR B 2
H42F H 1.4588 0.3795 0.8619 0.071 Uiso 0.477(12) 1 calc PR B 2
C43 C 1.448(2) 0.6108(7) 0.7861(3) 0.070(2) Uani 1 1 d . . .
C44 C 1.2854(19) 0.6330(9) 0.7490(4) 0.080(3) Uani 1 1 d . B .
H44 H 1.1259 0.5905 0.7504 0.096 Uiso 1 1 calc R . .
C45 C 1.342(2) 0.7124(9) 0.7110(3) 0.083(3) Uani 1 1 d . . .
H45 H 1.2238 0.7205 0.6864 0.099 Uiso 1 1 calc R B .
C46 C 1.5769(18) 0.7831(7) 0.7078(3) 0.065(2) Uani 1 1 d . B .
C47 C 1.744(2) 0.7648(7) 0.7441(3) 0.078(3) Uani 1 1 d . . .
H47 H 1.9011 0.8104 0.7437 0.094 Uiso 1 1 calc R B .
C48 C 1.679(2) 0.6758(9) 0.7830(3) 0.079(3) Uani 1 1 d . B .
H48 H 1.7975 0.6626 0.8063 0.095 Uiso 1 1 calc R . .
C49 C 1.640(2) 0.8740(8) 0.6684(4) 0.087(3) Uani 1 1 d . . .
H49A H 1.5090 0.9136 0.6664 0.104 Uiso 1 1 calc R B .
H49B H 1.7811 0.9329 0.6826 0.104 Uiso 1 1 calc R . .
C50 C 1.688(4) 0.8342(10) 0.6133(4) 0.160(8) Uani 1 1 d . A .
C51 C 1.841(5) 0.9231(14) 0.5804(6) 0.147(12) Uani 0.576(10) 1 d P A 1
H51A H 1.7409 0.9565 0.5577 0.221 Uiso 0.576(10) 1 calc PR A 1
H51B H 1.9417 0.8854 0.5580 0.221 Uiso 0.576(10) 1 calc PR A 1
H51C H 1.9402 0.9850 0.6042 0.221 Uiso 0.576(10) 1 calc PR A 1
C52 C 1.590(6) 0.7317(16) 0.5859(6) 0.160(13) Uani 0.576(10) 1 d P A 1
H52A H 1.5739 0.6684 0.6097 0.240 Uiso 0.576(10) 1 calc PR A 1
H52B H 1.6900 0.7189 0.5562 0.240 Uiso 0.576(10) 1 calc PR A 1
H52C H 1.4333 0.7336 0.5719 0.240 Uiso 0.576(10) 1 calc PR A 1
C51' C 1.623(5) 0.947(3) 0.5738(11) 0.113(10) Uani 0.424(10) 1 d P A 2
H51D H 1.4542 0.9445 0.5755 0.170 Uiso 0.424(10) 1 calc PR A 2
H51E H 1.6639 0.9328 0.5366 0.170 Uiso 0.424(10) 1 calc PR A 2
H51F H 1.7150 1.0232 0.5881 0.170 Uiso 0.424(10) 1 calc PR A 2
C52' C 1.885(5) 0.789(3) 0.6061(11) 0.125(12) Uani 0.424(10) 1 d P A 2
H52D H 1.8639 0.7380 0.5731 0.187 Uiso 0.424(10) 1 calc PR A 2
H52E H 1.9043 0.7437 0.6365 0.187 Uiso 0.424(10) 1 calc PR A 2
H52F H 2.0256 0.8526 0.6038 0.187 Uiso 0.424(10) 1 calc PR A 2
N1 N -0.1675(9) 0.7524(5) 1.1291(2) 0.0474(14) Uani 1 1 d . . .
N2 N 0.0708(11) 0.3029(5) 0.9457(2) 0.0513(15) Uani 1 1 d . . .
C53 C -0.3034(12) 0.7163(6) 1.0832(3) 0.0503(17) Uani 1 1 d . . .
H53 H -0.4319 0.7501 1.0766 0.060 Uiso 1 1 calc R . .
C54 C -0.2605(11) 0.6335(6) 1.0465(2) 0.0423(15) Uani 1 1 d . . .
H54 H -0.3517 0.6147 1.0142 0.051 Uiso 1 1 calc R . .
C56 C 0.0566(11) 0.6098(6) 1.1052(3) 0.0454(16) Uani 1 1 d . . .
H56 H 0.1781 0.5733 1.1144 0.054 Uiso 1 1 calc R . .
C57 C 0.0062(12) 0.6984(6) 1.1386(3) 0.0480(16) Uani 1 1 d . . .
H57 H 0.1003 0.7227 1.1702 0.058 Uiso 1 1 calc R . .
C58 C -0.1040(14) 0.3553(6) 0.9346(3) 0.0546(18) Uani 1 1 d . B .
H58 H -0.1960 0.3308 0.9026 0.066 Uiso 1 1 calc R . .
C59 C -0.1547(13) 0.4463(6) 0.9693(3) 0.0511(17) Uani 1 1 d . . .
H59 H -0.2748 0.4833 0.9597 0.061 Uiso 1 1 calc R B .
C60 C -0.0267(11) 0.4811(5) 1.0179(3) 0.0389(14) Uani 1 1 d . B .
C61 C 0.1557(12) 0.4263(5) 1.0290(3) 0.0478(17) Uani 1 1 d . . .
H61 H 0.2525 0.4495 1.0604 0.057 Uiso 1 1 calc R B .
C62 C 0.1932(11) 0.3340(5) 0.9919(3) 0.0456(16) Uani 1 1 d . B .
H62 H 0.3096 0.2940 1.0006 0.055 Uiso 1 1 calc R . .
N3 N 0.8438(9) 1.2647(5) 1.1247(2) 0.0472(14) Uani 1 1 d . . .
N4 N 1.0561(11) 0.7942(5) 0.9501(2) 0.0538(15) Uani 1 1 d . . .
C63 C 0.7079(12) 1.2242(6) 1.0801(3) 0.0510(18) Uani 1 1 d . . .
H63 H 0.5806 1.2583 1.0729 0.061 Uiso 1 1 calc R . .
C64 C 0.7430(12) 1.1359(6) 1.0441(2) 0.0474(16) Uani 1 1 d . . .
H64 H 0.6480 1.1146 1.0124 0.057 Uiso 1 1 calc R . .
C65 C 0.9242(11) 1.0770(6) 1.0554(3) 0.0427(15) Uani 1 1 d . . .
C66 C 1.0622(11) 1.1142(6) 1.1034(3) 0.0485(17) Uani 1 1 d . . .
H66 H 1.1806 1.0766 1.1135 0.058 Uiso 1 1 calc R . .
C67 C 1.0166(14) 1.2094(7) 1.1357(3) 0.0544(18) Uani 1 1 d . . .
H67 H 1.1129 1.2362 1.1669 0.065 Uiso 1 1 calc R . .
C68 C 0.8861(14) 0.8475(6) 0.9386(3) 0.0558(19) Uani 1 1 d . B .
H68 H 0.7925 0.8220 0.9069 0.067 Uiso 1 1 calc R . .
C69 C 0.8412(14) 0.9387(6) 0.9711(3) 0.0542(18) Uani 1 1 d . . .
H69 H 0.7199 0.9745 0.9610 0.065 Uiso 1 1 calc R B .
C71 C 1.1507(11) 0.9246(5) 1.0308(3) 0.0479(17) Uani 1 1 d . . .
H71 H 1.2480 0.9503 1.0620 0.057 Uiso 1 1 calc R B .
C72 C 1.1867(12) 0.8290(6) 0.9957(3) 0.0503(18) Uani 1 1 d . B .
H72 H 1.3041 0.7899 1.0049 0.060 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C70 C71 1.360(9) . ?
C70 C69 1.373(9) . ?
C70 C65 1.490(5) . ?
C55 C56 1.390(9) . ?
C55 C54 1.403(9) . ?
C55 C60 1.490(5) . ?
C55 C65 7.134(9) . ?
O1 C1 1.234(9) . ?
O1 N1 3.409(8) . ?
O2 C1 1.257(9) . ?
C1 C2 1.516(11) . ?
C2 C3 1.467(12) . ?
C2 C4 1.535(11) . ?
C4 C5 1.346(10) . ?
C4 C9 1.385(12) . ?
C5 C6 1.379(11) . ?
C6 C7 1.344(11) . ?
C7 C8 1.387(11) . ?
C7 C10 1.526(11) . ?
C8 C9 1.409(12) . ?
C10 C11 1.579(17) . ?
C11 C12A 1.10(4) . ?
C11 C12' 1.36(4) . ?
C11 C13A 1.54(3) . ?
C11 C13' 1.56(3) . ?
C11 C12 1.73(3) . ?
C11 C13 1.83(3) . ?
C12 C13 1.03(3) . ?
C13 C13A 2.01(3) . ?
C12' C13A 0.67(4) . ?
C12' C12A 1.37(5) . ?
C13' C12A 1.98(4) . ?
C13A C12A 1.93(4) . ?
O3 C14 1.238(8) . ?
O3 N3 3.458(8) . ?
O4 C14 1.281(8) . ?
C14 C15 1.494(11) . ?
C15 C17 1.514(11) . ?
C15 C16 1.531(11) . ?
C17 C18 1.335(11) . ?
C17 C22 1.362(11) . ?
C18 C19 1.426(11) . ?
C19 C20 1.339(11) . ?
C20 C21 1.381(11) . ?
C20 C23 1.545(11) . ?
C21 C22 1.360(12) . ?
C23 C24 1.485(16) . ?
C23 C24' 1.73(3) . ?
C24 C25A 0.91(10) . ?
C24 C25 1.35(2) . ?
C24 C26 1.64(3) . ?
C25 C25A 1.49(10) . ?
C26 C25A 1.71(8) . ?
C24' C25A 0.54(9) . ?
C24' C25' 0.84(4) . ?
C25' C25A 0.75(12) . ?
C26' C25A 1.90(9) . ?
O5 C27 1.346(10) . ?
O6 C27 1.154(9) . ?
O6 N2 3.384(8) . ?
C27 C28 1.545(14) . ?
C27 C28' 1.560(14) . ?
C28 C30 1.464(16) . ?
C28 C29 1.51(2) . ?
C28' C29' 1.538(18) . ?
C28' C30 1.650(16) . ?
C30 C35 1.347(14) . ?
C30 C31 1.387(13) . ?
C31 C32 1.370(12) . ?
C32 C33 1.427(12) . ?
C33 C34 1.343(13) . ?
C33 C36 1.490(12) . ?
C34 C35 1.379(13) . ?
C36 C37 1.448(14) . ?
C36 C37' 1.79(4) . ?
C37 C38 1.23(3) . ?
C37 C39 1.70(4) . ?
O7 C40 1.333(10) . ?
O8 C40 1.161(9) . ?
O8 N4 3.483(9) . ?
C40 C41' 1.566(17) . ?
C40 C41 1.587(18) . ?
C41 C42 1.43(2) . ?
C41 C43 1.497(17) . ?
C41' C42' 1.55(2) . ?
C41' C43 1.625(18) . ?
C43 C48 1.361(14) . ?
C43 C44 1.377(13) . ?
C44 C45 1.345(13) . ?
C45 C46 1.402(13) . ?
C46 C47 1.362(12) . ?
C46 C49 1.466(12) . ?
C47 C48 1.443(12) . ?
C49 C50 1.453(15) . ?
C50 C52 1.32(2) . ?
C50 C52' 1.36(3) . ?
C50 C51 1.478(16) . ?
C50 C51' 1.79(3) . ?
N1 C57 1.323(9) . ?
N1 C53 1.347(9) . ?
N2 C62 1.309(9) . ?
N2 C58 1.324(9) . ?
C53 C54 1.340(10) . ?
C56 C57 1.360(10) . ?
C58 C59 1.401(10) . ?
C59 C60 1.378(9) . ?
C60 C61 1.380(9) . ?
C61 C62 1.418(9) . ?
N3 C63 1.329(9) . ?
N3 C67 1.336(9) . ?
N4 C68 1.311(10) . ?
N4 C72 1.325(9) . ?
C63 C64 1.360(11) . ?
C64 C65 1.406(9) . ?
C65 C66 1.396(9) . ?
C66 C67 1.394(10) . ?
C68 C69 1.358(11) . ?
C71 C72 1.416(10) . ?

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
C71 C70 C69 117.1(7) . . ?
C71 C70 C65 120.9(5) . . ?
C69 C70 C65 122.0(5) . . ?
C56 C55 C54 117.2(6) . . ?
C56 C55 C60 120.7(5) . . ?
C54 C55 C60 122.0(5) . . ?
C56 C55 C65 62.7(4) . . ?
C54 C55 C65 97.9(4) . . ?
C60 C55 C65 107.1(2) . . ?
C1 O1 N1 78.0(4) . . ?
O1 C1 O2 123.7(7) . . ?
O1 C1 C2 124.3(7) . . ?
O2 C1 C2 111.9(7) . . ?
C3 C2 C1 114.0(7) . . ?
C3 C2 C4 112.6(7) . . ?
C1 C2 C4 108.4(7) . . ?
C5 C4 C9 117.7(7) . . ?
C5 C4 C2 121.6(7) . . ?
C9 C4 C2 120.7(7) . . ?
C4 C5 C6 122.7(8) . . ?
C7 C6 C5 121.0(8) . . ?
C6 C7 C8 118.4(7) . . ?
C6 C7 C10 122.1(8) . . ?
C8 C7 C10 119.5(8) . . ?
C7 C8 C9 120.2(8) . . ?
C4 C9 C8 120.0(7) . . ?
C7 C10 C11 111.2(9) . . ?
C12A C11 C12' 67(3) . . ?
C12A C11 C13A 92(3) . . ?
C12' C11 C13A 25.7(18) . . ?
C12A C11 C13' 94(3) . . ?
C12' C11 C13' 121(2) . . ?
C13A C11 C13' 118.2(17) . . ?
C12A C11 C10 129(3) . . ?
C12' C11 C10 122(2) . . ?
C13A C11 C10 108.4(13) . . ?
C13' C11 C10 113.7(16) . . ?
C12A C11 C12 116(3) . . ?
C12' C11 C12 116(2) . . ?
C13A C11 C12 103.2(16) . . ?
C13' C11 C12 25.1(13) . . ?
C10 C11 C12 103.8(14) . . ?
C12A C11 C13 131(3) . . ?
C12' C11 C13 92(2) . . ?
C13A C11 C13 72.6(13) . . ?
C13' C11 C13 57.3(15) . . ?
C10 C11 C13 100.3(13) . . ?
C12 C11 C13 33.6(11) . . ?
C13 C12 C11 78(2) . . ?
C12 C13 C11 68(2) . . ?
C12 C13 C13A 111(3) . . ?
C11 C13 C13A 47.0(10) . . ?
C13A C12' C12A 139(6) . . ?
C13A C12' C11 92(5) . . ?
C12A C12' C11 47(2) . . ?
C11 C13' C12A 33.7(13) . . ?
C12' C13A C11 62(4) . . ?
C12' C13A C12A 28(4) . . ?
C11 C13A C12A 34.8(14) . . ?
C12' C13A C13 110(5) . . ?
C11 C13A C13 60.4(13) . . ?
C12A C13A C13 85.8(17) . . ?
C11 C12A C12' 66(3) . . ?
C11 C12A C13A 53(2) . . ?
C12' C12A C13A 13.1(19) . . ?
C11 C12A C13' 52(2) . . ?
C12' C12A C13' 97(3) . . ?
C13A C12A C13' 85.8(17) . . ?
C14 O3 N3 78.1(4) . . ?
O3 C14 O4 122.9(7) . . ?
O3 C14 C15 126.7(7) . . ?
O4 C14 C15 110.3(6) . . ?
C14 C15 C17 109.2(6) . . ?
C14 C15 C16 110.0(7) . . ?
C17 C15 C16 115.5(8) . . ?
C18 C17 C22 120.4(7) . . ?
C18 C17 C15 117.1(7) . . ?
C22 C17 C15 122.5(8) . . ?
C17 C18 C19 119.1(7) . . ?
C20 C19 C18 120.6(7) . . ?
C19 C20 C21 118.5(7) . . ?
C19 C20 C23 119.6(7) . . ?
C21 C20 C23 121.8(8) . . ?
C22 C21 C20 120.9(7) . . ?
C21 C22 C17 120.4(7) . . ?
C24 C23 C20 118.5(9) . . ?
C24 C23 C24' 28.2(8) . . ?
C20 C23 C24' 102.5(9) . . ?
C25A C24 C25 80(5) . . ?
C25A C24 C23 124(5) . . ?
C25 C24 C23 127.0(13) . . ?
C25A C24 C26 78(5) . . ?
C25 C24 C26 127.6(17) . . ?
C23 C24 C26 104.4(14) . . ?
C24 C25 C25A 37(4) . . ?
C24 C26 C25A 32(3) . . ?
C25A C24' C25' 61(10) . . ?
C25A C24' C23 133(10) . . ?
C25' C24' C23 138(3) . . ?
C25A C25' C24' 39(7) . . ?
C24' C25A C25' 79(10) . . ?
C24' C25A C24 62(10) . . ?
C25' C25A C24 138(10) . . ?
C24' C25A C25 82(10) . . ?
C25' C25A C25 131(9) . . ?
C24 C25A C25 63(6) . . ?
C24' C25A C26 114(10) . . ?
C25' C25A C26 115(9) . . ?
C24 C25A C26 70(5) . . ?
C25 C25A C26 114(6) . . ?
C24' C25A C26' 112(10) . . ?
C25' C25A C26' 142(9) . . ?
C24 C25A C26' 53(5) . . ?
C25 C25A C26' 88(5) . . ?
C26 C25A C26' 26.2(18) . . ?
C27 O6 N2 80.3(5) . . ?
O6 C27 O5 123.9(7) . . ?
O6 C27 C28 111.8(10) . . ?
O5 C27 C28 123.7(9) . . ?
O6 C27 C28' 132.8(8) . . ?
O5 C27 C28' 102.2(8) . . ?
C28 C27 C28' 28.6(6) . . ?
C30 C28 C29 108.1(15) . . ?
C30 C28 C27 112.3(9) . . ?
C29 C28 C27 101.5(11) . . ?
C29' C28' C27 106.8(9) . . ?
C29' C28' C30 106.3(11) . . ?
C27 C28' C30 102.2(7) . . ?
C35 C30 C31 118.8(8) . . ?
C35 C30 C28 105.1(11) . . ?
C31 C30 C28 136.2(12) . . ?
C35 C30 C28' 132.8(9) . . ?
C31 C30 C28' 108.4(10) . . ?
C28 C30 C28' 27.7(7) . . ?
C32 C31 C30 119.2(9) . . ?
C31 C32 C33 122.2(9) . . ?
C34 C33 C32 115.5(8) . . ?
C34 C33 C36 122.6(10) . . ?
C32 C33 C36 121.9(9) . . ?
C33 C34 C35 122.6(10) . . ?
C30 C35 C34 121.5(9) . . ?
C37 C36 C33 113.6(8) . . ?
C37 C36 C37' 38.0(10) . . ?
C33 C36 C37' 109.3(13) . . ?
C38 C37 C36 120.3(18) . . ?
C38 C37 C39 109(2) . . ?
C36 C37 C39 95.6(17) . . ?
C40 O8 N4 78.6(5) . . ?
O8 C40 O7 125.1(7) . . ?
O8 C40 C41' 130.8(9) . . ?
O7 C40 C41' 103.4(8) . . ?
O8 C40 C41 111.8(10) . . ?
O7 C40 C41 122.9(8) . . ?
C41' C40 C41 23.8(6) . . ?
C42 C41 C43 108.4(14) . . ?
C42 C41 C40 107.5(13) . . ?
C43 C41 C40 106.1(10) . . ?
C42' C41' C40 110.4(11) . . ?
C42' C41' C43 105.8(11) . . ?
C40 C41' C43 101.1(9) . . ?
C48 C43 C44 115.9(8) . . ?
C48 C43 C41 106.8(10) . . ?
C44 C43 C41 137.3(12) . . ?
C48 C43 C41' 130.4(9) . . ?
C44 C43 C41' 113.7(10) . . ?
C41 C43 C41' 23.6(7) . . ?
C45 C44 C43 124.1(10) . . ?
C44 C45 C46 121.3(9) . . ?
C47 C46 C45 116.5(8) . . ?
C47 C46 C49 121.4(9) . . ?
C45 C46 C49 122.1(9) . . ?
C46 C47 C48 120.9(9) . . ?
C43 C48 C47 121.2(9) . . ?
C50 C49 C46 117.1(8) . . ?
C52 C50 C52' 79.4(18) . . ?
C52 C50 C49 128.2(12) . . ?
C52' C50 C49 117.6(18) . . ?
C52 C50 C51 114.3(12) . . ?
C52' C50 C51 78(2) . . ?
C49 C50 C51 117.0(10) . . ?
C52 C50 C51' 105.9(16) . . ?
C52' C50 C51' 124(2) . . ?
C49 C50 C51' 102.7(16) . . ?
C51 C50 C51' 47.8(14) . . ?
C57 N1 C53 117.3(6) . . ?
C57 N1 O1 157.9(5) . . ?
C53 N1 O1 84.7(4) . . ?
C62 N2 C58 118.7(6) . . ?
C62 N2 O6 84.2(4) . . ?
C58 N2 O6 157.1(5) . . ?
C54 C53 N1 122.5(7) . . ?
C53 C54 C55 120.1(6) . . ?
C57 C56 C55 118.3(6) . . ?
N1 C57 C56 124.5(6) . . ?
N2 C58 C59 122.2(7) . . ?
C60 C59 C58 120.0(6) . . ?
C59 C60 C61 117.3(6) . . ?
C59 C60 C55 122.0(4) . . ?
C61 C60 C55 120.7(5) . . ?
C60 C61 C62 119.0(6) . . ?
N2 C62 C61 122.7(6) . . ?
C63 N3 C67 116.6(6) . . ?
C63 N3 O3 87.6(4) . . ?
C67 N3 O3 154.9(5) . . ?
C68 N4 C72 118.8(6) . . ?
C68 N4 O8 154.6(5) . . ?
C72 N4 O8 86.1(4) . . ?
N3 C63 C64 124.3(7) . . ?
C63 C64 C65 119.4(6) . . ?
C66 C65 C64 117.4(6) . . ?
C66 C65 C70 119.8(5) . . ?
C64 C65 C70 122.8(4) . . ?
C66 C65 C55 118.6(4) . . ?
C64 C65 C55 82.5(4) . . ?
C70 C65 C55 71.1(2) . . ?
C67 C66 C65 117.9(6) . . ?
N3 C67 C66 124.3(6) . . ?
N4 C68 C69 122.6(7) . . ?
C68 C69 C70 120.9(7) . . ?
C70 C71 C72 119.4(6) . . ?
N4 C72 C71 121.2(6) . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        28.09
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.119

# Attachment 'x506r_SS-1to3.cif'

data_x506r
_database_code_depnum_ccdc_archive 'CCDC 734644'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N O2'
_chemical_formula_weight         280.33

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           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.702(3)
_cell_length_b                   11.600(7)
_cell_length_c                   24.523(14)
_cell_angle_alpha                93.589(13)
_cell_angle_beta                 90.734(12)
_cell_angle_gamma                103.756(11)
_cell_volume                     1571.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18678
_diffrn_reflns_av_R_equivalents  0.2415
_diffrn_reflns_av_sigmaI/netI    0.2076
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         0.83
_diffrn_reflns_theta_max         28.36
_reflns_number_total             14253
_reflns_number_gt                6512
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(4)
_refine_ls_number_reflns         14253
_refine_ls_number_parameters     797
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2764
_refine_ls_R_factor_gt           0.2123
_refine_ls_wR_factor_ref         0.5365
_refine_ls_wR_factor_gt          0.4897
_refine_ls_goodness_of_fit_ref   1.536
_refine_ls_restrained_S_all      1.536
_refine_ls_shift/su_max          6.084
_refine_ls_shift/su_mean         0.126

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 0.2707(12) 0.8633(5) 1.1619(3) 0.0420(15) Uani 1 1 d . . .
O2 O -0.0553(12) 0.8892(7) 1.1176(3) 0.0513(18) Uani 1 1 d . . .
C1 C 0.072(2) 0.9062(8) 1.1567(4) 0.046(2) Uani 1 1 d . . .
C2 C 0.039(2) 0.9772(10) 1.2095(4) 0.048(3) Uani 1 1 d . . .
H2 H 0.20(2) 1.026(11) 1.221(5) 0.058 Uiso 1 1 calc . . .
C3 C -0.121(2) 1.0606(10) 1.1984(5) 0.067(3) Uani 1 1 d . . .
H3A H -0.2873 1.0169 1.1966 0.101 Uiso 1 1 calc R . .
H3B H -0.0799 1.0955 1.1643 0.101 Uiso 1 1 calc R . .
H3C H -0.0987 1.1223 1.2273 0.101 Uiso 1 1 calc R . .
C4 C -0.0437(17) 0.8931(9) 1.2522(3) 0.039(2) Uani 1 1 d . . .
C5 C 0.116(2) 0.8745(12) 1.2893(5) 0.063(3) Uani 1 1 d . . .
H5 H 0.2740 0.9198 1.2904 0.075 Uiso 1 1 calc R . .
C6 C 0.044(2) 0.7874(15) 1.3260(5) 0.073(4) Uani 1 1 d . . .
H6 H 0.1586 0.7769 1.3514 0.088 Uiso 1 1 calc R . .
C7 C -0.1871(19) 0.7148(9) 1.3275(4) 0.048(2) Uani 1 1 d . . .
C8 C -0.355(2) 0.7449(11) 1.2912(5) 0.060(3) Uani 1 1 d . . .
H8 H -0.5177 0.7076 1.2928 0.072 Uiso 1 1 calc R . .
C9 C -0.2801(18) 0.8288(9) 1.2536(4) 0.042(2) Uani 1 1 d . . .
H9 H -0.3925 0.8423 1.2284 0.051 Uiso 1 1 calc R . .
C10 C -0.267(3) 0.6199(12) 1.3677(4) 0.067(3) Uani 1 1 d . . .
H10A H -0.4259 0.5727 1.3557 0.080 Uiso 1 1 calc R . .
H10B H -0.1576 0.5676 1.3656 0.080 Uiso 1 1 calc R . .
C11 C -0.281(5) 0.6604(13) 1.4259(6) 0.125(9) Uani 1 1 d . . .
H11 H -0.12(4) 0.710(17) 1.437(8) 0.151 Uiso 1 1 calc . . .
C12 C -0.321(6) 0.5534(18) 1.4606(6) 0.232(17) Uani 1 1 d . . .
H12A H -0.4913 0.5220 1.4645 0.348 Uiso 1 1 calc R . .
H12B H -0.2455 0.5774 1.4961 0.348 Uiso 1 1 calc R . .
H12C H -0.2520 0.4933 1.4432 0.348 Uiso 1 1 calc R . .
C13 C -0.402(13) 0.727(5) 1.414(4) 0.53(10) Uani 0.50 1 d P . .
H13A H -0.5317 0.6856 1.3893 0.794 Uiso 0.50 1 calc PR . .
H13B H -0.3040 0.7926 1.3962 0.794 Uiso 0.50 1 calc PR . .
H13C H -0.4677 0.7566 1.4462 0.794 Uiso 0.50 1 calc PR . .
O3 O 0.2608(13) 1.3541(6) 1.1640(3) 0.0489(17) Uani 1 1 d . . .
O4 O -0.0560(13) 1.3795(6) 1.1160(3) 0.0502(17) Uani 1 1 d . . .
C14 C 0.0736(17) 1.4014(7) 1.1567(4) 0.039(2) Uani 1 1 d . . .
C15 C 0.055(2) 1.4858(8) 1.2030(4) 0.044(2) Uani 1 1 d . . .
H15 H 0.22(2) 1.533(10) 1.213(4) 0.053 Uiso 1 1 calc . . .
C16 C -0.100(2) 1.5702(9) 1.1918(5) 0.067(3) Uani 1 1 d . . .
H16A H -0.2612 1.5259 1.1823 0.100 Uiso 1 1 calc R . .
H16B H -0.0349 1.6169 1.1621 0.100 Uiso 1 1 calc R . .
H16C H -0.1018 1.6219 1.2238 0.100 Uiso 1 1 calc R . .
C17 C -0.0411(18) 1.4127(7) 1.2528(4) 0.039(2) Uani 1 1 d . . .
C18 C 0.110(2) 1.4129(10) 1.2947(5) 0.052(2) Uani 1 1 d . . .
H18 H 0.2706 1.4545 1.2934 0.063 Uiso 1 1 calc R . .
C19 C 0.031(2) 1.3530(9) 1.3390(5) 0.054(3) Uani 1 1 d . . .
H19 H 0.1412 1.3525 1.3672 0.065 Uiso 1 1 calc R . .
C20 C -0.206(3) 1.2926(10) 1.3438(6) 0.067(3) Uani 1 1 d . . .
C21 C -0.369(2) 1.2902(9) 1.2999(5) 0.057(3) Uani 1 1 d . . .
H21 H -0.5289 1.2481 1.3012 0.068 Uiso 1 1 calc R . .
C22 C -0.286(2) 1.3510(9) 1.2551(4) 0.051(3) Uani 1 1 d . . .
H22 H -0.3922 1.3517 1.2260 0.061 Uiso 1 1 calc R . .
C23 C -0.312(3) 1.2287(14) 1.3954(6) 0.082(4) Uiso 1 1 d . . .
C24 C -0.335(4) 1.087(2) 1.3785(9) 0.126(6) Uiso 1 1 d . . .
C25 C -0.096(6) 1.080(3) 1.3850(12) 0.172(10) Uiso 1 1 d . . .
C26 C -0.291(8) 1.063(4) 1.4600(17) 0.117(12) Uiso 0.50 1 d P . .
C26' C -0.484(5) 1.037(2) 1.4369(10) 0.067(6) Uiso 0.50 1 d P . .
O5 O 0.6407(16) 0.5805(7) 0.8348(3) 0.061(2) Uani 1 1 d . A .
O6 O 0.9429(17) 0.5644(7) 0.8875(4) 0.069(2) Uani 1 1 d . A .
C27 C 0.833(2) 0.5452(9) 0.8447(4) 0.051(3) Uani 1 1 d . . .
C28 C 0.853(8) 0.485(5) 0.7948(17) 0.14(3) Uani 0.35(3) 1 d P A 1
H28 H 0.69(13) 0.45(6) 0.78(3) 0.172 Uiso 0.35 1 calc P A 1
C29 C 0.996(7) 0.369(3) 0.8107(10) 0.054(10) Uani 0.35(3) 1 d P A 1
H29A H 0.8987 0.3185 0.8358 0.081 Uiso 0.35(3) 1 calc PR A 1
H29B H 1.1525 0.4027 0.8271 0.081 Uiso 0.35(3) 1 calc PR A 1
H29C H 1.0117 0.3221 0.7778 0.081 Uiso 0.35(3) 1 calc PR A 1
C28' C 0.942(5) 0.4757(14) 0.7982(7) 0.071(8) Uani 0.65(3) 1 d P A 2
H28' H 1.10(4) 0.47(2) 0.811(8) 0.085 Uiso 0.65 1 calc P A 2
C29' C 0.795(6) 0.3594(13) 0.7924(9) 0.090(9) Uani 0.65(3) 1 d P A 2
H29D H 0.8712 0.3104 0.7692 0.135 Uiso 0.65(3) 1 calc PR A 2
H29E H 0.6411 0.3610 0.7765 0.135 Uiso 0.65(3) 1 calc PR A 2
H29F H 0.7720 0.3275 0.8277 0.135 Uiso 0.65(3) 1 calc PR A 2
C30 C 0.973(3) 0.5444(14) 0.7487(5) 0.075(4) Uani 1 1 d . . .
C31 C 0.806(3) 0.5399(11) 0.7074(6) 0.070(4) Uani 1 1 d . A .
H31 H 0.6466 0.4993 0.7122 0.084 Uiso 1 1 calc R . .
C32 C 0.863(3) 0.5925(16) 0.6596(6) 0.087(5) Uani 1 1 d . . .
H32 H 0.7469 0.5872 0.6320 0.105 Uiso 1 1 calc R A .
C33 C 1.100(2) 0.6539(11) 0.6531(4) 0.060(3) Uani 1 1 d . A .
C34 C 1.253(3) 0.6680(19) 0.6940(6) 0.114(7) Uani 1 1 d . . .
H34 H 1.4024 0.7212 0.6919 0.137 Uiso 1 1 calc R A .
C35 C 1.201(3) 0.6066(16) 0.7408(6) 0.095(5) Uani 1 1 d . A .
H35 H 1.3227 0.6082 0.7666 0.113 Uiso 1 1 calc R . .
C36 C 1.166(3) 0.7086(15) 0.6010(7) 0.093(5) Uiso 1 1 d . . .
C37 C 1.125(4) 0.829(2) 0.5942(9) 0.094(7) Uiso 0.77(3) 1 d P A 1
C37' C 1.356(11) 0.753(5) 0.557(2) 0.08(2) Uiso 0.23(3) 1 d P A 2
C38 C 1.061(7) 0.876(3) 0.6251(15) 0.218(15) Uiso 1 1 d . . .
C39 C 1.145(6) 0.887(3) 0.5451(13) 0.172(11) Uiso 1 1 d . A .
O7 O 0.6300(16) 0.0721(7) 0.8358(3) 0.063(2) Uani 1 1 d . A .
O8 O 0.9386(17) 0.0573(7) 0.8857(4) 0.066(2) Uani 1 1 d . A .
C40 C 0.819(2) 0.0383(8) 0.8428(4) 0.046(2) Uani 1 1 d . . .
C41 C 0.824(5) -0.0421(18) 0.7910(11) 0.027(6) Uani 0.35(3) 1 d P A 1
H41 H 0.66(5) -0.09(3) 0.777(11) 0.032 Uiso 0.35 1 calc P A 1
C42 C 0.990(6) -0.122(2) 0.7997(14) 0.056(10) Uani 0.35(3) 1 d P A 1
H42A H 0.9028 -0.1930 0.8154 0.084 Uiso 0.35(3) 1 calc PR A 1
H42B H 1.1214 -0.0818 0.8240 0.084 Uiso 0.35(3) 1 calc PR A 1
H42C H 1.0524 -0.1432 0.7653 0.084 Uiso 0.35(3) 1 calc PR A 1
C41' C 0.949(4) -0.0135(15) 0.7981(8) 0.051(5) Uani 0.65(3) 1 d P A 2
H41' H 1.11(3) -0.018(15) 0.811(7) 0.061 Uiso 0.65 1 calc P A 2
C42' C 0.786(6) -0.1408(14) 0.7815(10) 0.096(10) Uani 0.65(3) 1 d P A 2
H42D H 0.8005 -0.1596 0.7432 0.144 Uiso 0.65(3) 1 calc PR A 2
H42E H 0.6205 -0.1422 0.7890 0.144 Uiso 0.65(3) 1 calc PR A 2
H42F H 0.8371 -0.1985 0.8022 0.144 Uiso 0.65(3) 1 calc PR A 2
C43 C 0.968(3) 0.0635(9) 0.7484(4) 0.056(3) Uani 1 1 d . . .
C44 C 0.795(3) 0.0712(12) 0.7110(5) 0.071(4) Uani 1 1 d . A .
H44 H 0.6422 0.0208 0.7125 0.086 Uiso 1 1 calc R . .
C45 C 0.840(3) 0.1535(14) 0.6701(6) 0.084(4) Uani 1 1 d . . .
H45 H 0.7191 0.1638 0.6465 0.101 Uiso 1 1 calc R A .
C46 C 1.079(3) 0.2182(16) 0.6676(6) 0.096(5) Uani 1 1 d . A .
C47 C 1.248(3) 0.2146(13) 0.7034(5) 0.075(4) Uani 1 1 d . . .
H47 H 1.3992 0.2667 0.7022 0.090 Uiso 1 1 calc R A .
C48 C 1.202(3) 0.1336(12) 0.7430(5) 0.070(4) Uani 1 1 d . A .
H48 H 1.3266 0.1254 0.7662 0.084 Uiso 1 1 calc R . .
C49 C 1.109(3) 0.3253(12) 0.6262(7) 0.100(5) Uani 1 1 d . . .
H49A H 0.9648 0.3555 0.6259 0.120 Uiso 1 1 calc R A .
H49B H 1.2452 0.3901 0.6382 0.120 Uiso 1 1 calc R . .
C50 C 1.146(3) 0.2819(17) 0.5761(6) 0.096(5) Uani 1 1 d . A .
H50 H 1.00(3) 0.218(15) 0.565(6) 0.116 Uiso 1 1 calc . . .
C51 C 1.145(4) 0.3931(16) 0.5402(9) 0.119(7) Uani 1 1 d . . .
H51A H 1.2759 0.4029 0.5154 0.178 Uiso 1 1 calc R A .
H51B H 1.1637 0.4639 0.5639 0.178 Uiso 1 1 calc R . .
H51C H 0.9947 0.3788 0.5199 0.178 Uiso 1 1 calc R . .
C52 C 1.359(4) 0.243(2) 0.5610(6) 0.138(9) Uani 1 1 d . . .
H52A H 1.4033 0.1976 0.5893 0.208 Uiso 1 1 calc R A .
H52B H 1.4897 0.3106 0.5562 0.208 Uiso 1 1 calc R . .
H52C H 1.3275 0.1938 0.5274 0.208 Uiso 1 1 calc R . .
N1 N 0.3212(15) 0.7013(8) 1.0867(3) 0.047(2) Uani 1 1 d . . .
N2 N 0.5455(15) 0.2352(6) 0.9101(3) 0.0429(18) Uani 1 1 d . . .
C53 C 0.496(2) 0.6462(9) 1.0975(4) 0.052(3) Uani 1 1 d . . .
H53 H 0.5924 0.6725 1.1288 0.063 Uiso 1 1 calc R . .
C54 C 0.5430(18) 0.5516(9) 1.0648(4) 0.043(2) Uani 1 1 d . . .
H54 H 0.6654 0.5156 1.0744 0.051 Uiso 1 1 calc R . .
C55 C 0.4037(16) 0.5130(8) 1.0178(3) 0.0354(19) Uani 1 1 d . . .
C56 C 0.2198(17) 0.5701(8) 1.0076(4) 0.042(2) Uani 1 1 d . . .
H56 H 0.1199 0.5472 0.9766 0.050 Uiso 1 1 calc R . .
C57 C 0.1863(19) 0.6594(9) 1.0431(4) 0.047(2) Uani 1 1 d . . .
H57 H 0.0579 0.6932 1.0357 0.056 Uiso 1 1 calc R . .
C58 C 0.3750(19) 0.2890(9) 0.8988(4) 0.046(2) Uani 1 1 d . A .
H58 H 0.2816 0.2643 0.8670 0.055 Uiso 1 1 calc R . .
C59 C 0.3282(19) 0.3795(9) 0.9317(4) 0.047(2) Uani 1 1 d . . .
H59 H 0.2089 0.4166 0.9210 0.056 Uiso 1 1 calc R A .
C60 C 0.4537(15) 0.4171(7) 0.9803(4) 0.0332(19) Uani 1 1 d . A .
C61 C 0.6334(19) 0.3578(9) 0.9925(4) 0.048(2) Uani 1 1 d . . .
H61 H 0.7258 0.3786 1.0247 0.058 Uiso 1 1 calc R A .
C62 C 0.6732(17) 0.2664(7) 0.9556(4) 0.037(2) Uani 1 1 d . A .
H62 H 0.7929 0.2275 0.9639 0.045 Uiso 1 1 calc R . .
N3 N 0.3168(14) 1.1911(6) 1.0893(3) 0.0413(18) Uani 1 1 d . . .
N4 N 0.5516(16) 0.7392(7) 0.9068(3) 0.0440(19) Uani 1 1 d . . .
C63 C 0.4874(18) 1.1387(7) 1.1007(4) 0.040(2) Uani 1 1 d . . .
H63 H 0.5761 1.1617 1.1333 0.048 Uiso 1 1 calc R . .
C64 C 0.5437(18) 1.0485(8) 1.0657(4) 0.042(2) Uani 1 1 d . . .
H64 H 0.6689 1.0140 1.0750 0.050 Uiso 1 1 calc R . .
C65 C 0.4116(15) 1.0117(6) 1.0176(3) 0.0291(18) Uani 1 1 d . . .
C66 C 0.2258(18) 1.0685(8) 1.0076(4) 0.041(2) Uani 1 1 d . . .
H66 H 0.1311 1.0471 0.9758 0.049 Uiso 1 1 calc R . .
C67 C 0.1800(16) 1.1565(8) 1.0445(4) 0.0359(19) Uani 1 1 d . . .
H67 H 0.0524 1.1912 1.0375 0.043 Uiso 1 1 calc R . .
C68 C 0.6751(19) 0.7718(8) 0.9539(4) 0.045(2) Uani 1 1 d . A .
H68 H 0.7943 0.7327 0.9622 0.054 Uiso 1 1 calc R . .
C69 C 0.6394(17) 0.8583(8) 0.9905(4) 0.037(2) Uani 1 1 d . . .
H69 H 0.7326 0.8779 1.0227 0.045 Uiso 1 1 calc R A .
C70 C 0.4626(18) 0.9157(8) 0.9790(4) 0.042(2) Uani 1 1 d . A .
C71 C 0.3335(17) 0.8854(7) 0.9309(3) 0.037(2) Uani 1 1 d . . .
H71 H 0.2160 0.9245 0.9212 0.044 Uiso 1 1 calc R A .
C72 C 0.3808(18) 0.7973(9) 0.8979(4) 0.048(2) Uani 1 1 d . A .
H72 H 0.2863 0.7750 0.8661 0.058 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.350(12) . ?
O2 C1 1.173(12) . ?
O2 N1 3.463(11) . ?
C1 C2 1.528(14) . ?
C2 C4 1.480(13) . ?
C2 C3 1.514(15) . ?
C4 C5 1.341(14) . ?
C4 C9 1.379(14) . ?
C5 C6 1.387(17) . ?
C6 C7 1.387(18) . ?
C7 C8 1.415(14) . ?
C7 C10 1.518(15) . ?
C8 C9 1.380(15) . ?
C10 C11 1.483(19) . ?
C11 C13 1.20(3) . ?
C11 C12 1.523(19) . ?
O3 C14 1.326(11) . ?
O4 C14 1.210(12) . ?
O4 N3 3.434(10) . ?
C14 C15 1.475(13) . ?
C15 C16 1.501(14) . ?
C15 C17 1.561(11) . ?
C17 C18 1.331(14) . ?
C17 C22 1.415(15) . ?
C18 C19 1.350(15) . ?
C19 C20 1.378(17) . ?
C20 C21 1.408(17) . ?
C20 C23 1.562(19) . ?
C21 C22 1.369(16) . ?
C23 C24 1.64(3) . ?
C24 C25 1.40(3) . ?
C24 C26' 1.73(3) . ?
C26 C26' 1.19(4) . ?
O5 C27 1.281(14) . ?
O6 C27 1.198(13) . ?
O6 N4 3.372(11) . ?
C27 C28 1.39(4) . ?
C27 C28' 1.576(15) . ?
C28 C30 1.45(5) . ?
C28 C29 1.79(5) . ?
C28' C29' 1.41(3) . ?
C28' C30 1.48(2) . ?
C30 C35 1.35(2) . ?
C30 C31 1.374(19) . ?
C31 C32 1.363(19) . ?
C32 C33 1.38(2) . ?
C33 C34 1.299(18) . ?
C33 C36 1.48(2) . ?
C34 C35 1.39(2) . ?
C36 C37 1.49(3) . ?
C36 C37' 1.56(7) . ?
C37 C38 1.02(4) . ?
C37 C39 1.41(3) . ?
C38 C39 2.03(5) . ?
O7 C40 1.243(13) . ?
O8 C40 1.227(13) . ?
O8 N2 3.423(12) . ?
C40 C41' 1.51(2) . ?
C40 C41 1.53(3) . ?
C41 C42 1.50(3) . ?
C41 C43 1.72(3) . ?
C41' C43 1.545(17) . ?
C41' C42' 1.57(3) . ?
C43 C44 1.358(17) . ?
C43 C48 1.402(19) . ?
C44 C45 1.411(18) . ?
C45 C46 1.40(2) . ?
C46 C47 1.305(19) . ?
C46 C49 1.63(2) . ?
C47 C48 1.377(17) . ?
C49 C50 1.33(2) . ?
C50 C52 1.44(2) . ?
C50 C51 1.61(2) . ?
N1 C57 1.307(13) . ?
N1 C53 1.338(13) . ?
N2 C62 1.308(12) . ?
N2 C58 1.309(12) . ?
C53 C54 1.398(13) . ?
C54 C55 1.379(12) . ?
C55 C56 1.395(12) . ?
C55 C60 1.481(9) . ?
C56 C57 1.360(15) . ?
C58 C59 1.362(14) . ?
C59 C60 1.373(13) . ?
C60 C61 1.402(14) . ?
C61 C62 1.413(14) . ?
N3 C63 1.299(12) . ?
N3 C67 1.325(12) . ?
N4 C68 1.329(13) . ?
N4 C72 1.333(12) . ?
C63 C64 1.410(13) . ?
C64 C65 1.381(12) . ?
C65 C66 1.400(11) . ?
C65 C70 1.500(9) . ?
C66 C67 1.394(13) . ?
C68 C69 1.358(13) . ?
C69 C70 1.370(13) . ?
C70 C71 1.364(12) . ?
C71 C72 1.343(13) . ?

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
C1 O2 N1 78.7(6) . . ?
O2 C1 O1 124.2(9) . . ?
O2 C1 C2 126.3(10) . . ?
O1 C1 C2 109.4(9) . . ?
C4 C2 C3 115.7(10) . . ?
C4 C2 C1 108.7(9) . . ?
C3 C2 C1 109.9(9) . . ?
C5 C4 C9 118.5(9) . . ?
C5 C4 C2 119.8(10) . . ?
C9 C4 C2 121.6(9) . . ?
C4 C5 C6 119.9(12) . . ?
C5 C6 C7 124.4(10) . . ?
C6 C7 C8 113.7(10) . . ?
C6 C7 C10 124.7(10) . . ?
C8 C7 C10 121.2(11) . . ?
C9 C8 C7 121.1(11) . . ?
C8 C9 C4 121.8(9) . . ?
C11 C10 C7 117.4(11) . . ?
C13 C11 C10 91(4) . . ?
C13 C11 C12 134(6) . . ?
C10 C11 C12 109.2(14) . . ?
C14 O4 N3 79.7(6) . . ?
O4 C14 O3 123.1(9) . . ?
O4 C14 C15 126.1(9) . . ?
O3 C14 C15 110.8(9) . . ?
C14 C15 C16 114.8(9) . . ?
C14 C15 C17 108.2(7) . . ?
C16 C15 C17 110.3(9) . . ?
C18 C17 C22 119.9(8) . . ?
C18 C17 C15 118.8(10) . . ?
C22 C17 C15 121.3(9) . . ?
C17 C18 C19 120.3(11) . . ?
C18 C19 C20 122.4(11) . . ?
C19 C20 C21 118.3(11) . . ?
C19 C20 C23 125.0(12) . . ?
C21 C20 C23 116.8(12) . . ?
C22 C21 C20 118.7(11) . . ?
C21 C22 C17 120.4(10) . . ?
C20 C23 C24 104.1(13) . . ?
C25 C24 C23 101(2) . . ?
C25 C24 C26' 107.1(19) . . ?
C23 C24 C26' 95.1(15) . . ?
C26 C26' C24 87(3) . . ?
C27 O6 N4 79.2(6) . . ?
O6 C27 O5 124.2(10) . . ?
O6 C27 C28 135.9(16) . . ?
O5 C27 C28 99.9(15) . . ?
O6 C27 C28' 116.0(14) . . ?
O5 C27 C28' 119.8(13) . . ?
C28 C27 C28' 20.1(16) . . ?
C27 C28 C30 123(4) . . ?
C27 C28 C29 105(2) . . ?
C30 C28 C29 108.7(17) . . ?
C29' C28' C30 117(2) . . ?
C29' C28' C27 107.0(16) . . ?
C30 C28' C27 109.4(9) . . ?
C35 C30 C31 116.9(13) . . ?
C35 C30 C28 134(2) . . ?
C31 C30 C28 109(2) . . ?
C35 C30 C28' 115.1(17) . . ?
C31 C30 C28' 127.4(18) . . ?
C28 C30 C28' 21.5(12) . . ?
C32 C31 C30 122.6(14) . . ?
C31 C32 C33 118.3(13) . . ?
C34 C33 C32 119.1(12) . . ?
C34 C33 C36 121.8(15) . . ?
C32 C33 C36 118.9(13) . . ?
C33 C34 C35 122.2(16) . . ?
C30 C35 C34 119.9(15) . . ?
C33 C36 C37 117.9(16) . . ?
C33 C36 C37' 151(3) . . ?
C37 C36 C37' 80(3) . . ?
C38 C37 C39 112(3) . . ?
C38 C37 C36 122(3) . . ?
C39 C37 C36 125(2) . . ?
C37 C38 C39 40(2) . . ?
C37 C39 C38 27.9(15) . . ?
C40 O8 N2 79.1(6) . . ?
O8 C40 O7 123.7(10) . . ?
O8 C40 C41' 111.1(13) . . ?
O7 C40 C41' 124.5(12) . . ?
O8 C40 C41 132.9(13) . . ?
O7 C40 C41 102.7(13) . . ?
C41' C40 C41 27.5(9) . . ?
C42 C41 C40 110.3(19) . . ?
C42 C41 C43 107(2) . . ?
C40 C41 C43 99.5(12) . . ?
C40 C41' C43 109.3(11) . . ?
C40 C41' C42' 105.8(17) . . ?
C43 C41' C42' 109.1(18) . . ?
C44 C43 C48 118.1(10) . . ?
C44 C43 C41' 129.7(15) . . ?
C48 C43 C41' 112.2(13) . . ?
C44 C43 C41 104.9(13) . . ?
C48 C43 C41 136.9(13) . . ?
C41' C43 C41 24.8(8) . . ?
C43 C44 C45 122.1(13) . . ?
C46 C45 C44 115.4(13) . . ?
C47 C46 C45 123.7(12) . . ?
C47 C46 C49 121.8(15) . . ?
C45 C46 C49 112.4(14) . . ?
C46 C47 C48 120.0(15) . . ?
C47 C48 C43 120.0(13) . . ?
C50 C49 C46 108.3(14) . . ?
C49 C50 C52 124.1(17) . . ?
C49 C50 C51 101.8(17) . . ?
C52 C50 C51 105.6(16) . . ?
C57 N1 C53 115.7(9) . . ?
C57 N1 O2 89.0(6) . . ?
C53 N1 O2 154.6(6) . . ?
C62 N2 C58 119.2(8) . . ?
C62 N2 O8 83.4(5) . . ?
C58 N2 O8 157.0(6) . . ?
N1 C53 C54 124.2(10) . . ?
C55 C54 C53 118.5(9) . . ?
C54 C55 C56 116.5(8) . . ?
C54 C55 C60 120.7(7) . . ?
C56 C55 C60 122.9(7) . . ?
C57 C56 C55 120.1(9) . . ?
N1 C57 C56 124.9(9) . . ?
N2 C58 C59 123.0(9) . . ?
C58 C59 C60 121.3(9) . . ?
C59 C60 C61 115.4(9) . . ?
C59 C60 C55 122.9(7) . . ?
C61 C60 C55 121.7(7) . . ?
C60 C61 C62 119.6(9) . . ?
N2 C62 C61 121.5(9) . . ?
C63 N3 C67 120.0(8) . . ?
C63 N3 O4 154.9(7) . . ?
C67 N3 O4 84.8(5) . . ?
C68 N4 C72 114.6(8) . . ?
C68 N4 O6 83.3(5) . . ?
C72 N4 O6 161.8(6) . . ?
N3 C63 C64 122.8(9) . . ?
C65 C64 C63 119.5(8) . . ?
C64 C65 C66 115.7(8) . . ?
C64 C65 C70 121.8(6) . . ?
C66 C65 C70 122.5(7) . . ?
C67 C66 C65 121.4(9) . . ?
N3 C67 C66 120.5(8) . . ?
N4 C68 C69 124.6(9) . . ?
C68 C69 C70 118.3(9) . . ?
C71 C70 C69 118.8(8) . . ?
C71 C70 C65 119.8(7) . . ?
C69 C70 C65 121.4(7) . . ?
C72 C71 C70 118.1(8) . . ?
N4 C72 C71 125.6(9) . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         1.451
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.229

# Attachment 'x516t_S-enantiomorph.cif'

data_x516t
_database_code_depnum_ccdc_archive 'CCDC 734645'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N O2'
_chemical_formula_weight         284.37

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   P21

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

_cell_length_a                   5.725(2)
_cell_length_b                   48.556(19)
_cell_length_c                   11.522(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.316(8)
_cell_angle_gamma                90.00
_cell_volume                     3117(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30560
_diffrn_reflns_av_R_equivalents  0.2406
_diffrn_reflns_av_sigmaI/netI    0.2831
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -61
_diffrn_reflns_limit_k_max       64
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         28.17
_reflns_number_total             14623
_reflns_number_gt                5298
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1206P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0000(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5(3)
_refine_ls_number_reflns         14623
_refine_ls_number_parameters     795
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2585
_refine_ls_R_factor_gt           0.1314
_refine_ls_wR_factor_ref         0.3532
_refine_ls_wR_factor_gt          0.2787
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          7.432
_refine_ls_shift/su_mean         0.056

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 0.9282(10) 0.16462(13) 0.2560(6) 0.0552(17) Uani 1 1 d . . .
H1 H 0.9139 0.1778 0.2981 0.083 Uiso 1 1 calc R . .
O2 O 1.2380(10) 0.18812(12) 0.2251(6) 0.0498(16) Uani 1 1 d . . .
C1 C 1.1136(14) 0.16846(16) 0.2089(7) 0.0332(18) Uani 1 1 d . . .
C2 C 1.1443(16) 0.14416(16) 0.1300(7) 0.039(2) Uani 1 1 d . . .
H2 H 0.985(15) 0.1389(15) 0.083(8) 0.047 Uiso 1 1 calc . . .
C3 C 1.2956(16) 0.15217(18) 0.0456(8) 0.047(2) Uani 1 1 d . . .
H3A H 1.2296 0.1683 0.0023 0.070 Uiso 1 1 calc R . .
H3B H 1.2982 0.1374 -0.0093 0.070 Uiso 1 1 calc R . .
H3C H 1.4562 0.1560 0.0897 0.070 Uiso 1 1 calc R . .
C4 C 1.2490(14) 0.11950(15) 0.2102(7) 0.0343(18) Uani 1 1 d . . .
C5 C 1.1123(15) 0.09700(18) 0.2167(8) 0.046(2) Uani 1 1 d . . .
H5 H 0.9521 0.0966 0.1758 0.055 Uiso 1 1 calc R . .
C6 C 1.2136(17) 0.0746(2) 0.2850(9) 0.053(2) Uani 1 1 d . . .
H6 H 1.1180 0.0593 0.2902 0.063 Uiso 1 1 calc R . .
C7 C 1.4469(16) 0.07420(18) 0.3443(7) 0.045(2) Uani 1 1 d . . .
C8 C 1.5822(16) 0.0973(2) 0.3376(8) 0.054(2) Uani 1 1 d . . .
H8 H 1.7420 0.0979 0.3790 0.065 Uiso 1 1 calc R . .
C9 C 1.4818(14) 0.11979(18) 0.2693(7) 0.040(2) Uani 1 1 d . . .
H9 H 1.5758 0.1352 0.2643 0.047 Uiso 1 1 calc R . .
C10 C 1.554(2) 0.0495(2) 0.4136(9) 0.066(3) Uani 1 1 d . . .
H10A H 1.7125 0.0464 0.3999 0.079 Uiso 1 1 calc R . .
H10B H 1.4559 0.0335 0.3843 0.079 Uiso 1 1 calc R . .
C11 C 1.574(3) 0.0523(2) 0.5487(12) 0.079(4) Uani 1 1 d . . .
H11 H 1.67(2) 0.069(2) 0.577(11) 0.094 Uiso 1 1 calc . . .
C12 C 1.343(3) 0.0554(3) 0.5802(11) 0.106(5) Uani 1 1 d . . .
H12A H 1.2410 0.0403 0.5484 0.159 Uiso 1 1 calc R . .
H12B H 1.2700 0.0724 0.5475 0.159 Uiso 1 1 calc R . .
H12C H 1.3674 0.0558 0.6654 0.159 Uiso 1 1 calc R . .
C13 C 1.707(3) 0.0263(3) 0.6118(13) 0.123(5) Uani 1 1 d . . .
H13A H 1.7912 0.0311 0.6914 0.185 Uiso 1 1 calc R . .
H13B H 1.8203 0.0199 0.5679 0.185 Uiso 1 1 calc R . .
H13C H 1.5930 0.0120 0.6149 0.185 Uiso 1 1 calc R . .
O3 O 0.9112(10) 0.16499(11) -0.2595(5) 0.0424(14) Uani 1 1 d . . .
H3O H 0.8940 0.1794 -0.2249 0.064 Uiso 1 1 calc R . .
O4 O 1.2369(10) 0.18623(12) -0.2875(6) 0.0503(15) Uani 1 1 d . . .
C14 C 1.1067(13) 0.16662(18) -0.3012(8) 0.041(2) Uani 1 1 d . . .
C15 C 1.1422(18) 0.14018(17) -0.3651(8) 0.044(2) Uani 1 1 d . . .
H15 H 0.986(16) 0.1338(17) -0.412(9) 0.053 Uiso 1 1 calc . . .
C16 C 1.3073(17) 0.1450(2) -0.4481(8) 0.057(3) Uani 1 1 d . . .
H16A H 1.2330 0.1575 -0.5100 0.086 Uiso 1 1 calc R . .
H16B H 1.3379 0.1278 -0.4829 0.086 Uiso 1 1 calc R . .
H16C H 1.4559 0.1526 -0.4040 0.086 Uiso 1 1 calc R . .
C17 C 1.2403(14) 0.11912(16) -0.2664(7) 0.0373(19) Uani 1 1 d . . .
C18 C 1.0857(16) 0.10069(17) -0.2325(10) 0.052(2) Uani 1 1 d . . .
H18 H 0.9239 0.1011 -0.2709 0.062 Uiso 1 1 calc R . .
C19 C 1.1624(17) 0.08198(18) -0.1451(9) 0.052(2) Uani 1 1 d . . .
H19 H 1.0544 0.0693 -0.1270 0.062 Uiso 1 1 calc R . .
C20 C 1.3952(18) 0.08148(18) -0.0833(8) 0.050(2) Uani 1 1 d . . .
C21 C 1.5564(16) 0.10028(18) -0.1171(8) 0.046(2) Uani 1 1 d . . .
H21 H 1.7179 0.1002 -0.0782 0.055 Uiso 1 1 calc R . .
C22 C 1.4743(15) 0.11854(18) -0.2071(9) 0.045(2) Uani 1 1 d . . .
H22 H 1.5813 0.1309 -0.2283 0.054 Uiso 1 1 calc R . .
C23 C 1.489(2) 0.0614(2) 0.0172(9) 0.062(3) Uani 1 1 d . . .
H23A H 1.6173 0.0704 0.0743 0.074 Uiso 1 1 calc R . .
H23B H 1.3606 0.0578 0.0574 0.074 Uiso 1 1 calc R . .
C24 C 1.581(3) 0.0344(3) -0.0164(13) 0.083(4) Uani 1 1 d . . .
H24 H 1.70(2) 0.038(2) -0.066(12) 0.100 Uiso 1 1 calc . . .
C25 C 1.370(3) 0.0174(3) -0.0892(15) 0.127(6) Uani 1 1 d . . .
H25A H 1.2737 0.0107 -0.0373 0.191 Uiso 1 1 calc R . .
H25B H 1.4317 0.0021 -0.1258 0.191 Uiso 1 1 calc R . .
H25C H 1.2740 0.0288 -0.1498 0.191 Uiso 1 1 calc R . .
C26 C 1.706(3) 0.0190(3) 0.0927(13) 0.115(5) Uani 1 1 d . . .
H26A H 1.8499 0.0286 0.1306 0.172 Uiso 1 1 calc R . .
H26B H 1.7473 0.0008 0.0704 0.172 Uiso 1 1 calc R . .
H26C H 1.6024 0.0175 0.1469 0.172 Uiso 1 1 calc R . .
O5 O 0.5025(9) 0.33164(11) 0.9832(5) 0.0440(14) Uani 1 1 d . . .
H5A H 0.5509 0.3175 0.9576 0.066 Uiso 1 1 calc R . .
O6 O 0.2081(10) 0.30425(12) 1.0071(6) 0.0494(16) Uani 1 1 d . . .
C27 C 0.3009(14) 0.32647(17) 1.0156(6) 0.0320(18) Uani 1 1 d . . .
C28 C 0.1908(16) 0.35132(17) 1.0659(7) 0.039(2) Uani 1 1 d . . .
H28 H 0.039(14) 0.3455(15) 1.084(8) 0.047 Uiso 1 1 calc . . .
C29 C 0.356(2) 0.3607(2) 1.1804(8) 0.069(3) Uani 1 1 d . . .
H29A H 0.3690 0.3466 1.2396 0.104 Uiso 1 1 calc R . .
H29B H 0.2935 0.3772 1.2080 0.104 Uiso 1 1 calc R . .
H29C H 0.5125 0.3645 1.1665 0.104 Uiso 1 1 calc R . .
C30 C 0.1350(15) 0.37316(15) 0.9678(6) 0.0330(18) Uani 1 1 d . . .
C31 C 0.3032(16) 0.39155(17) 0.9483(8) 0.046(2) Uani 1 1 d . . .
H31 H 0.4569 0.3908 0.9973 0.055 Uiso 1 1 calc R . .
C32 C 0.2550(14) 0.41094(17) 0.8600(8) 0.041(2) Uani 1 1 d . . .
H32 H 0.3744 0.4231 0.8502 0.049 Uiso 1 1 calc R . .
C33 C 0.0245(16) 0.41251(16) 0.7839(8) 0.043(2) Uani 1 1 d . . .
C34 C -0.1447(15) 0.39445(16) 0.8057(8) 0.041(2) Uani 1 1 d . . .
H34 H -0.2999 0.3952 0.7584 0.049 Uiso 1 1 calc R . .
C35 C -0.0897(15) 0.37498(16) 0.8972(8) 0.039(2) Uani 1 1 d . . .
H35 H -0.2088 0.3631 0.9099 0.047 Uiso 1 1 calc R . .
C36 C -0.0263(18) 0.43254(17) 0.6830(7) 0.050(2) Uani 1 1 d . . .
H36A H 0.0992 0.4309 0.6394 0.060 Uiso 1 1 calc R . .
H36B H -0.1763 0.4274 0.6291 0.060 Uiso 1 1 calc R . .
C37 C -0.0431(19) 0.4617(2) 0.7165(9) 0.058(3) Uani 1 1 d . . .
H37 H 0.102(17) 0.4662(18) 0.777(9) 0.070 Uiso 1 1 calc . . .
C38 C -0.052(3) 0.4809(2) 0.6108(11) 0.103(5) Uani 1 1 d . . .
H38A H 0.0914 0.4785 0.5818 0.155 Uiso 1 1 calc R . .
H38B H -0.0624 0.4996 0.6356 0.155 Uiso 1 1 calc R . .
H38C H -0.1894 0.4765 0.5485 0.155 Uiso 1 1 calc R . .
C39 C -0.255(2) 0.4685(2) 0.7671(10) 0.077(3) Uani 1 1 d . . .
H39A H -0.4001 0.4661 0.7066 0.115 Uiso 1 1 calc R . .
H39B H -0.2434 0.4872 0.7945 0.115 Uiso 1 1 calc R . .
H39C H -0.2576 0.4564 0.8327 0.115 Uiso 1 1 calc R . .
O7 O 0.4686(10) 0.33027(11) 0.4624(5) 0.0460(15) Uani 1 1 d . . .
H7 H 0.5261 0.3172 0.4333 0.069 Uiso 1 1 calc R . .
O8 O 0.2130(12) 0.29878(13) 0.4941(6) 0.0571(18) Uani 1 1 d . . .
C40 C 0.2792(15) 0.32202(18) 0.4987(7) 0.038(2) Uani 1 1 d . . .
C41 C 0.1513(16) 0.34416(18) 0.5565(8) 0.042(2) Uani 1 1 d . . .
H41 H -0.012(15) 0.3376(15) 0.554(8) 0.051 Uiso 1 1 calc . . .
C42 C 0.2832(19) 0.34669(19) 0.6859(7) 0.057(3) Uani 1 1 d . . .
H42A H 0.4463 0.3521 0.6903 0.086 Uiso 1 1 calc R . .
H42B H 0.2811 0.3293 0.7249 0.086 Uiso 1 1 calc R . .
H42C H 0.2059 0.3603 0.7244 0.086 Uiso 1 1 calc R . .
C43 C 0.1310(14) 0.37163(17) 0.4882(7) 0.040(2) Uani 1 1 d . . .
C44 C 0.3172(16) 0.38926(19) 0.4975(8) 0.045(2) Uani 1 1 d . . .
H44 H 0.4675 0.3844 0.5432 0.054 Uiso 1 1 calc R . .
C45 C 0.2879(15) 0.41374(18) 0.4415(7) 0.044(2) Uani 1 1 d . . .
H45 H 0.4199 0.4253 0.4496 0.053 Uiso 1 1 calc R . .
C46 C 0.0727(15) 0.42230(16) 0.3732(8) 0.041(2) Uani 1 1 d . . .
C47 C -0.1161(17) 0.40408(19) 0.3659(9) 0.051(2) Uani 1 1 d . . .
H47 H -0.2672 0.4091 0.3216 0.062 Uiso 1 1 calc R . .
C48 C -0.0881(15) 0.37873(18) 0.4220(8) 0.044(2) Uani 1 1 d . . .
H48 H -0.2175 0.3668 0.4145 0.053 Uiso 1 1 calc R . .
C49 C 0.035(2) 0.4497(2) 0.3123(8) 0.064(3) Uani 1 1 d . B .
H49A H 0.1490 0.4625 0.3587 0.077 Uiso 1 1 calc R . .
H49B H -0.1243 0.4561 0.3144 0.077 Uiso 1 1 calc R . .
C50 C 0.059(2) 0.4510(3) 0.1846(10) 0.092(5) Uani 1 1 d . . .
H50 H 0.00(2) 0.470(2) 0.160(13) 0.110 Uiso 1 1 calc . A 1
C51 C 0.265(4) 0.4519(6) 0.1736(15) 0.246(19) Uani 0.95(3) 1 d P B 1
H51A H 0.3724 0.4533 0.2508 0.369 Uiso 0.95(3) 1 calc PR B 1
H51B H 0.2855 0.4677 0.1266 0.369 Uiso 0.95(3) 1 calc PR B 1
H51C H 0.3007 0.4354 0.1346 0.369 Uiso 0.95(3) 1 calc PR B 1
C52 C -0.112(2) 0.4330(2) 0.0998(9) 0.080(3) Uani 1 1 d . B .
H52A H -0.0516 0.4298 0.0298 0.120 Uiso 1 1 calc R . .
H52B H -0.2656 0.4418 0.0776 0.120 Uiso 1 1 calc R . .
H52C H -0.1286 0.4157 0.1376 0.120 Uiso 1 1 calc R . .
N1 N 0.8585(12) 0.20178(15) 0.4086(6) 0.0425(17) Uani 1 1 d . . .
N2 N 0.6109(11) 0.29361(13) 0.8394(6) 0.0382(16) Uani 1 1 d . . .
C53 C 0.6848(14) 0.19648(17) 0.4638(7) 0.0381(19) Uani 1 1 d . . .
H53 H 0.5962 0.1804 0.4447 0.046 Uiso 1 1 calc R . .
C54 C 0.6292(14) 0.21406(17) 0.5494(7) 0.042(2) Uani 1 1 d . . .
H54 H 0.5065 0.2098 0.5870 0.050 Uiso 1 1 calc R . .
C55 C 0.7596(13) 0.23771(16) 0.5767(7) 0.0324(18) Uani 1 1 d . . .
C56 C 0.9423(12) 0.24298(17) 0.5224(8) 0.042(2) Uani 1 1 d . . .
H56 H 1.0364 0.2587 0.5406 0.051 Uiso 1 1 calc R . .
C57 C 0.9835(16) 0.22398(18) 0.4385(9) 0.049(2) Uani 1 1 d . . .
H57 H 1.1089 0.2275 0.4016 0.059 Uiso 1 1 calc R . .
C58 C 0.4912(15) 0.27044(16) 0.8143(8) 0.042(2) Uani 1 1 d . . .
H58 H 0.3750 0.2664 0.8564 0.050 Uiso 1 1 calc R . .
C59 C 0.5262(13) 0.25168(16) 0.7299(7) 0.0344(19) Uani 1 1 d . . .
H59 H 0.4354 0.2356 0.7153 0.041 Uiso 1 1 calc R . .
C60 C 0.7022(14) 0.25749(14) 0.6670(7) 0.0311(17) Uani 1 1 d . . .
C61 C 0.8241(15) 0.28137(17) 0.6934(8) 0.043(2) Uani 1 1 d . . .
H61 H 0.9424 0.2860 0.6534 0.051 Uiso 1 1 calc R . .
C62 C 0.7762(14) 0.29907(18) 0.7788(8) 0.043(2) Uani 1 1 d . . .
H62 H 0.8628 0.3154 0.7943 0.052 Uiso 1 1 calc R . .
N3 N 0.8589(11) 0.20274(13) -0.1069(6) 0.0344(15) Uani 1 1 d . . .
N4 N 0.6085(14) 0.29395(14) 0.3224(6) 0.0436(18) Uani 1 1 d . . .
C63 C 0.6834(14) 0.19731(17) -0.0525(7) 0.039(2) Uani 1 1 d . . .
H63 H 0.5886 0.1818 -0.0745 0.047 Uiso 1 1 calc R . .
C64 C 0.6381(15) 0.21448(17) 0.0372(7) 0.041(2) Uani 1 1 d . . .
H64 H 0.5149 0.2101 0.0743 0.049 Uiso 1 1 calc R . .
C65 C 0.7731(13) 0.23782(17) 0.0714(6) 0.0317(18) Uani 1 1 d . . .
C66 C 0.9538(14) 0.24262(17) 0.0114(7) 0.040(2) Uani 1 1 d . . .
H66 H 1.0489 0.2583 0.0291 0.047 Uiso 1 1 calc R . .
C67 C 0.9939(14) 0.22462(16) -0.0735(8) 0.038(2) Uani 1 1 d . . .
H67 H 1.1215 0.2280 -0.1090 0.046 Uiso 1 1 calc R . .
C68 C 0.5015(13) 0.27031(18) 0.3033(6) 0.0365(19) Uani 1 1 d . . .
H68 H 0.3879 0.2661 0.3467 0.044 Uiso 1 1 calc R . .
C69 C 0.5446(14) 0.25115(16) 0.2236(7) 0.0340(18) Uani 1 1 d . . .
H69 H 0.4621 0.2345 0.2131 0.041 Uiso 1 1 calc R . .
C70 C 0.7141(13) 0.25723(16) 0.1593(7) 0.0342(18) Uani 1 1 d . . .
C71 C 0.8258(14) 0.28256(15) 0.1786(7) 0.0326(18) Uani 1 1 d . . .
H71 H 0.9367 0.2878 0.1352 0.039 Uiso 1 1 calc R . .
C72 C 0.7711(15) 0.30010(18) 0.2635(7) 0.042(2) Uani 1 1 d . . .
H72 H 0.8525 0.3168 0.2789 0.050 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.312(9) . ?
O2 C1 1.180(8) . ?
O2 N1 3.427(9) . ?
C1 C2 1.524(11) . ?
C2 C3 1.495(11) . ?
C2 C4 1.546(11) . ?
C4 C9 1.350(11) . ?
C4 C5 1.356(11) . ?
C5 C6 1.390(12) . ?
C6 C7 1.353(12) . ?
C7 C8 1.377(12) . ?
C7 C10 1.491(13) . ?
C8 C9 1.389(12) . ?
C10 C11 1.540(16) . ?
C11 C12 1.452(17) . ?
C11 C13 1.566(16) . ?
O3 C14 1.318(9) . ?
O4 C14 1.197(9) . ?
O4 N3 3.425(8) . ?
C14 C15 1.517(12) . ?
C15 C16 1.509(12) . ?
C15 C17 1.537(12) . ?
C17 C22 1.357(12) . ?
C17 C18 1.377(11) . ?
C18 C19 1.352(13) . ?
C19 C20 1.359(13) . ?
C20 C21 1.415(12) . ?
C20 C23 1.513(13) . ?
C21 C22 1.363(13) . ?
C23 C24 1.500(16) . ?
C24 C26 1.496(17) . ?
C24 C25 1.540(18) . ?
O5 C27 1.317(9) . ?
O6 C27 1.197(9) . ?
O6 N2 3.372(9) . ?
C27 C28 1.535(11) . ?
C28 C29 1.507(12) . ?
C28 C30 1.529(10) . ?
C30 C35 1.358(11) . ?
C30 C31 1.369(11) . ?
C31 C32 1.367(12) . ?
C32 C33 1.408(12) . ?
C33 C34 1.372(11) . ?
C33 C36 1.492(11) . ?
C34 C35 1.397(11) . ?
C36 C37 1.478(13) . ?
C37 C39 1.499(13) . ?
C37 C38 1.524(13) . ?
O7 C40 1.312(9) . ?
O8 C40 1.187(9) . ?
O8 N4 3.340(9) . ?
C40 C41 1.537(12) . ?
C41 C42 1.512(12) . ?
C41 C43 1.539(12) . ?
C43 C44 1.352(11) . ?
C43 C48 1.354(11) . ?
C44 C45 1.344(12) . ?
C45 C46 1.365(12) . ?
C46 C47 1.384(12) . ?
C46 C49 1.495(13) . ?
C47 C48 1.383(12) . ?
C49 C50 1.511(15) . ?
C50 C51 1.22(2) . ?
C50 C52 1.497(15) . ?
N1 C57 1.296(11) . ?
N1 C53 1.323(10) . ?
N2 C58 1.314(10) . ?
N2 C62 1.326(11) . ?
C53 C54 1.396(11) . ?
C54 C55 1.366(11) . ?
C55 C56 1.361(11) . ?
C55 C60 1.507(10) . ?
C56 C57 1.395(12) . ?
C58 C59 1.380(11) . ?
C59 C60 1.399(11) . ?
C60 C61 1.352(11) . ?
C61 C62 1.380(12) . ?
N3 C67 1.318(10) . ?
N3 C63 1.327(10) . ?
N4 C68 1.296(10) . ?
N4 C72 1.307(10) . ?
C63 C64 1.397(11) . ?
C64 C65 1.377(11) . ?
C65 C66 1.390(10) . ?
C65 C70 1.478(10) . ?
C66 C67 1.369(11) . ?
C68 C69 1.369(11) . ?
C69 C70 1.382(11) . ?
C70 C71 1.381(10) . ?
C71 C72 1.386(11) . ?

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
C1 O2 N1 79.0(5) . . ?
O2 C1 O1 124.5(7) . . ?
O2 C1 C2 124.9(7) . . ?
O1 C1 C2 110.6(7) . . ?
C3 C2 C1 110.5(7) . . ?
C3 C2 C4 112.8(7) . . ?
C1 C2 C4 109.0(7) . . ?
C9 C4 C5 119.7(8) . . ?
C9 C4 C2 119.7(7) . . ?
C5 C4 C2 120.5(7) . . ?
C4 C5 C6 119.5(8) . . ?
C7 C6 C5 122.1(9) . . ?
C6 C7 C8 117.6(9) . . ?
C6 C7 C10 121.1(9) . . ?
C8 C7 C10 121.3(9) . . ?
C7 C8 C9 120.5(9) . . ?
C4 C9 C8 120.6(8) . . ?
C7 C10 C11 113.3(8) . . ?
C12 C11 C10 113.7(12) . . ?
C12 C11 C13 110.1(11) . . ?
C10 C11 C13 108.3(10) . . ?
C14 O4 N3 78.7(5) . . ?
O4 C14 O3 123.7(8) . . ?
O4 C14 C15 126.0(8) . . ?
O3 C14 C15 110.3(7) . . ?
C16 C15 C14 110.6(7) . . ?
C16 C15 C17 113.3(8) . . ?
C14 C15 C17 105.7(7) . . ?
C22 C17 C18 117.9(8) . . ?
C22 C17 C15 122.5(8) . . ?
C18 C17 C15 119.5(8) . . ?
C19 C18 C17 121.9(9) . . ?
C18 C19 C20 120.9(9) . . ?
C19 C20 C21 117.9(8) . . ?
C19 C20 C23 123.0(9) . . ?
C21 C20 C23 119.2(9) . . ?
C22 C21 C20 119.8(8) . . ?
C17 C22 C21 121.6(8) . . ?
C24 C23 C20 116.7(9) . . ?
C26 C24 C23 110.5(12) . . ?
C26 C24 C25 110.7(11) . . ?
C23 C24 C25 109.4(11) . . ?
C27 O6 N2 80.6(5) . . ?
O6 C27 O5 123.4(7) . . ?
O6 C27 C28 121.8(7) . . ?
O5 C27 C28 114.9(7) . . ?
C29 C28 C30 114.8(7) . . ?
C29 C28 C27 109.8(7) . . ?
C30 C28 C27 107.5(6) . . ?
C35 C30 C31 117.7(7) . . ?
C35 C30 C28 119.7(7) . . ?
C31 C30 C28 122.6(8) . . ?
C32 C31 C30 122.8(8) . . ?
C31 C32 C33 120.0(8) . . ?
C34 C33 C32 116.8(8) . . ?
C34 C33 C36 122.7(8) . . ?
C32 C33 C36 120.5(8) . . ?
C33 C34 C35 121.7(8) . . ?
C30 C35 C34 120.9(8) . . ?
C37 C36 C33 115.7(7) . . ?
C36 C37 C39 114.7(9) . . ?
C36 C37 C38 111.6(9) . . ?
C39 C37 C38 107.3(9) . . ?
C40 O8 N4 80.8(5) . . ?
O8 C40 O7 123.7(8) . . ?
O8 C40 C41 120.4(8) . . ?
O7 C40 C41 115.8(7) . . ?
C42 C41 C40 107.7(7) . . ?
C42 C41 C43 113.3(7) . . ?
C40 C41 C43 111.8(7) . . ?
C44 C43 C48 119.6(8) . . ?
C44 C43 C41 122.9(8) . . ?
C48 C43 C41 117.4(7) . . ?
C45 C44 C43 120.8(9) . . ?
C44 C45 C46 122.8(8) . . ?
C45 C46 C47 115.4(8) . . ?
C45 C46 C49 123.7(8) . . ?
C47 C46 C49 120.9(9) . . ?
C48 C47 C46 122.4(9) . . ?
C43 C48 C47 118.9(8) . . ?
C46 C49 C50 117.4(10) . . ?
C51 C50 C52 117.3(16) . . ?
C51 C50 C49 114.3(13) . . ?
C52 C50 C49 114.7(9) . . ?
C57 N1 C53 117.7(8) . . ?
C57 N1 O2 86.3(5) . . ?
C53 N1 O2 155.8(6) . . ?
C58 N2 C62 117.1(8) . . ?
C58 N2 O6 82.3(5) . . ?
C62 N2 O6 159.5(6) . . ?
N1 C53 C54 122.7(8) . . ?
C55 C54 C53 118.4(8) . . ?
C56 C55 C54 119.3(7) . . ?
C56 C55 C60 120.7(7) . . ?
C54 C55 C60 120.0(7) . . ?
C55 C56 C57 117.7(8) . . ?
N1 C57 C56 124.2(8) . . ?
N2 C58 C59 124.5(8) . . ?
C58 C59 C60 118.1(7) . . ?
C61 C60 C59 116.9(7) . . ?
C61 C60 C55 121.2(7) . . ?
C59 C60 C55 121.8(7) . . ?
C60 C61 C62 121.1(8) . . ?
N2 C62 C61 122.3(8) . . ?
C67 N3 C63 118.6(7) . . ?
C67 N3 O4 87.5(5) . . ?
C63 N3 O4 153.3(6) . . ?
C68 N4 C72 118.6(7) . . ?
C68 N4 O8 78.7(5) . . ?
C72 N4 O8 162.3(6) . . ?
N3 C63 C64 121.3(8) . . ?
C65 C64 C63 121.0(7) . . ?
C64 C65 C66 115.4(7) . . ?
C64 C65 C70 121.3(6) . . ?
C66 C65 C70 123.2(7) . . ?
C67 C66 C65 121.0(8) . . ?
N3 C67 C66 122.6(8) . . ?
N4 C68 C69 124.4(7) . . ?
C68 C69 C70 118.2(8) . . ?
C71 C70 C69 117.4(7) . . ?
C71 C70 C65 120.5(7) . . ?
C69 C70 C65 122.1(7) . . ?
C70 C71 C72 119.3(7) . . ?
N4 C72 C71 122.0(8) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.17
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.089


# Attachment 's-isomer_final.cif'

data_CAs-1
_database_code_depnum_ccdc_archive 'CCDC 750022'
#TrackingRef 's-isomer_final.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H18 O2), C10 H8 N2'
_chemical_formula_sum            'C36 H44 N2 O4'
_chemical_formula_weight         568.73
_chemical_absolute_configuration syn

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   P21

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

_cell_length_a                   5.7654(4)
_cell_length_b                   48.700(3)
_cell_length_c                   11.5146(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.6840(10)
_cell_angle_gamma                90.00
_cell_volume                     3141.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9602
_cell_measurement_theta_min      2.4725
_cell_measurement_theta_max      28.111

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   'Apex2 v2.1-4 (Bruker, 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'APEXII CCD'
_diffrn_measurement_method       omega
_diffrn_standards_number         0
_diffrn_reflns_number            37480
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -62
_diffrn_reflns_limit_k_max       62
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         28.36
_reflns_number_total             14433
_reflns_number_gt                13524
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Apex2 v2.1-4 (Bruker, 2007)'
_computing_cell_refinement       'Apex2 v2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Apex2 v2.1-4 (Bruker, 2007)'
_computing_structure_solution    'SHELXTL 6.3.1'
_computing_structure_refinement  'SHELXTL 6.3.1'
_computing_publication_material  'SHELXTL 6.3.1'
_computing_molecular_graphics    'ORTEP-3 for Windows v2.01'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. The disordered isobutyl
group in restrained with DFIX disances taken from a survey of isobutyl
groups from the CCDB. The methyl-methine and
methylene-methine distances were restrained to 1.52 angstroms. The
methyl-methyl distance was restrained to 2.49 angstrons. The
methyl-methylene distance was restrained to 2.51 angstroms. Additionally
the methylene carbon of the disordered isobutyl group was represented as two
atoms with their positions and ADPs constrined with EXYZ and EADP cards.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.6327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         14433
_refine_ls_number_parameters     815
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_restrained_S_all      0.886
_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 0.2603(2) 0.32766(2) 0.77610(11) 0.0254(3) Uani 1 1 d . . .
O2 O 0.5740(2) 0.30407(3) 0.74702(11) 0.0238(2) Uani 1 1 d . . .
H2O H 0.578(4) 0.3173(5) 0.691(2) 0.037(6) Uiso 1 1 d . . .
C1 C 0.3883(3) 0.30773(3) 0.79422(13) 0.0160(3) Uani 1 1 d . . .
C2 C 0.3554(3) 0.28342(3) 0.87290(14) 0.0178(3) Uani 1 1 d . . .
H2 H 0.5133 0.2780 0.9202 0.021 Uiso 1 1 calc R . .
C3 C 0.2033(3) 0.29148(3) 0.95943(15) 0.0230(3) Uani 1 1 d . . .
H3A H 0.2747 0.3069 1.0064 0.034 Uiso 1 1 calc R . .
H3B H 0.1937 0.2763 1.0112 0.034 Uiso 1 1 calc R . .
H3C H 0.0458 0.2963 0.9151 0.034 Uiso 1 1 calc R . .
C4 C 0.2503(3) 0.25908(3) 0.79450(13) 0.0176(3) Uani 1 1 d . . .
C5 C 0.3895(3) 0.23634(3) 0.78396(15) 0.0227(3) Uani 1 1 d . . .
H5 H 0.5503 0.2363 0.8230 0.027 Uiso 1 1 calc R . .
C6 C 0.2935(3) 0.21368(3) 0.71642(16) 0.0249(3) Uani 1 1 d . . .
H6 H 0.3909 0.1988 0.7109 0.030 Uiso 1 1 calc R . .
C7 C 0.0531(3) 0.21294(3) 0.65679(15) 0.0235(3) Uani 1 1 d . . .
C8 C -0.0855(3) 0.23610(4) 0.66475(15) 0.0237(3) Uani 1 1 d . . .
H8 H -0.2453 0.2364 0.6238 0.028 Uiso 1 1 calc R . .
C9 C 0.0106(3) 0.25876(3) 0.73266(15) 0.0216(3) Uani 1 1 d . . .
H9 H -0.0857 0.2739 0.7370 0.026 Uiso 1 1 calc R . .
C10 C -0.0552(3) 0.18830(4) 0.58368(17) 0.0288(4) Uani 1 1 d . . .
H10A H -0.2134 0.1851 0.5965 0.035 Uiso 1 1 calc R . .
H10B H 0.0410 0.1723 0.6125 0.035 Uiso 1 1 calc R . .
C11 C -0.0749(4) 0.19122(4) 0.44949(17) 0.0342(4) Uani 1 1 d . . .
H11 H -0.1698 0.2076 0.4210 0.041 Uiso 1 1 calc R . .
C12 C 0.1675(4) 0.19451(4) 0.42271(19) 0.0423(5) Uani 1 1 d . . .
H12A H 0.2633 0.1786 0.4505 0.063 Uiso 1 1 calc R . .
H12B H 0.2442 0.2106 0.4625 0.063 Uiso 1 1 calc R . .
H12C H 0.1493 0.1964 0.3380 0.063 Uiso 1 1 calc R . .
C13 C -0.2044(5) 0.16617(6) 0.3838(2) 0.0518(6) Uani 1 1 d . . .
H13A H -0.1099 0.1500 0.4078 0.078 Uiso 1 1 calc R . .
H13B H -0.2280 0.1687 0.2991 0.078 Uiso 1 1 calc R . .
H13C H -0.3564 0.1641 0.4033 0.078 Uiso 1 1 calc R . .
O3 O 0.2667(2) 0.32530(2) 1.29027(11) 0.0245(3) Uani 1 1 d . . .
O4 O 0.5934(2) 0.30408(2) 1.26237(11) 0.0201(2) Uani 1 1 d . . .
H4O H 0.591(4) 0.3176(5) 1.216(2) 0.036(6) Uiso 1 1 d . . .
C14 C 0.3992(3) 0.30571(3) 1.30453(13) 0.0170(3) Uani 1 1 d . . .
C15 C 0.3595(3) 0.27918(3) 1.36826(14) 0.0193(3) Uani 1 1 d . . .
H15 H 0.5145 0.2728 1.4155 0.023 Uiso 1 1 calc R . .
C16 C 0.1953(3) 0.28375(4) 1.45299(16) 0.0273(4) Uani 1 1 d . . .
H16A H 0.2682 0.2965 1.5142 0.041 Uiso 1 1 calc R . .
H16B H 0.1692 0.2666 1.4890 0.041 Uiso 1 1 calc R . .
H16C H 0.0452 0.2910 1.4090 0.041 Uiso 1 1 calc R . .
C17 C 0.2663(3) 0.25805(3) 1.27086(14) 0.0185(3) Uani 1 1 d . . .
C18 C 0.4220(3) 0.23983(3) 1.23480(15) 0.0217(3) Uani 1 1 d . . .
H18 H 0.5829 0.2400 1.2736 0.026 Uiso 1 1 calc R . .
C19 C 0.3407(3) 0.22143(3) 1.14180(16) 0.0240(3) Uani 1 1 d . . .
H19 H 0.4485 0.2095 1.1193 0.029 Uiso 1 1 calc R . .
C20 C 0.1013(3) 0.22044(3) 1.08164(15) 0.0224(3) Uani 1 1 d . . .
C21 C -0.0545(3) 0.23860(3) 1.11824(15) 0.0216(3) Uani 1 1 d . . .
H21 H -0.2157 0.2383 1.0799 0.026 Uiso 1 1 calc R . .
C22 C 0.0255(3) 0.25720(3) 1.21072(15) 0.0202(3) Uani 1 1 d . . .
H22 H -0.0822 0.2692 1.2327 0.024 Uiso 1 1 calc R . .
C23 C 0.0102(4) 0.20046(4) 0.98081(16) 0.0295(4) Uani 1 1 d . . .
H23A H 0.1362 0.1970 0.9399 0.035 Uiso 1 1 calc R . .
H23B H -0.1217 0.2089 0.9239 0.035 Uiso 1 1 calc R . .
C24 C -0.0736(4) 0.17295(4) 1.0210(2) 0.0402(5) Uani 1 1 d . . .
H24 H -0.1809 0.1767 1.0737 0.048 Uiso 1 1 calc R . .
C25 C -0.2128(6) 0.15701(6) 0.9122(3) 0.0707(10) Uani 1 1 d . . .
H25A H -0.3524 0.1672 0.8739 0.106 Uiso 1 1 calc R . .
H25B H -0.2597 0.1395 0.9374 0.106 Uiso 1 1 calc R . .
H25C H -0.1136 0.1543 0.8569 0.106 Uiso 1 1 calc R . .
C26 C 0.1376(6) 0.15602(5) 1.0908(3) 0.0707(10) Uani 1 1 d . . .
H26A H 0.2387 0.1511 1.0388 0.106 Uiso 1 1 calc R . .
H26B H 0.0793 0.1397 1.1210 0.106 Uiso 1 1 calc R . .
H26C H 0.2271 0.1667 1.1563 0.106 Uiso 1 1 calc R . .
O5 O 1.2915(2) 0.44348(2) -0.00675(12) 0.0272(3) Uani 1 1 d . . .
O6 O 0.9978(2) 0.47132(2) 0.01466(11) 0.0204(2) Uani 1 1 d . . .
H6O H 0.954(5) 0.4560(6) 0.050(2) 0.048(7) Uiso 1 1 d . . .
C27 C 1.1996(3) 0.46607(3) -0.01649(13) 0.0170(3) Uani 1 1 d . . .
C28 C 1.3088(3) 0.49089(3) -0.06387(14) 0.0204(3) Uani 1 1 d . . .
H28 H 1.4596 0.4849 -0.0811 0.025 Uiso 1 1 calc R . .
C29 C 1.1462(4) 0.50079(4) -0.18160(15) 0.0326(4) Uani 1 1 d . . .
H29A H 0.9948 0.5063 -0.1681 0.049 Uiso 1 1 calc R . .
H29B H 1.1228 0.4862 -0.2391 0.049 Uiso 1 1 calc R . .
H29C H 1.2191 0.5161 -0.2114 0.049 Uiso 1 1 calc R . .
C30 C 1.3677(3) 0.51302(3) 0.03189(13) 0.0168(3) Uani 1 1 d . . .
C31 C 1.1968(3) 0.53149(3) 0.05197(14) 0.0187(3) Uani 1 1 d . . .
H31 H 1.0428 0.5309 0.0037 0.022 Uiso 1 1 calc R . .
C32 C 1.2534(3) 0.55083(3) 0.14333(14) 0.0195(3) Uani 1 1 d . . .
H32 H 1.1369 0.5631 0.1548 0.023 Uiso 1 1 calc R . .
C33 C 1.4831(3) 0.55217(3) 0.21823(13) 0.0189(3) Uani 1 1 d . . .
C34 C 1.6541(3) 0.53424(3) 0.19584(14) 0.0202(3) Uani 1 1 d . . .
H34 H 1.8092 0.5352 0.2427 0.024 Uiso 1 1 calc R . .
C35 C 1.5979(3) 0.51477(3) 0.10409(14) 0.0190(3) Uani 1 1 d . . .
H35 H 1.7156 0.5029 0.0912 0.023 Uiso 1 1 calc R . .
C36 C 1.5370(3) 0.57219(3) 0.32128(14) 0.0248(3) Uani 1 1 d . . .
H36A H 1.6890 0.5673 0.3738 0.030 Uiso 1 1 calc R . .
H36B H 1.4157 0.5703 0.3665 0.030 Uiso 1 1 calc R . .
C37 C 1.5473(3) 0.60240(3) 0.28496(15) 0.0248(3) Uani 1 1 d . . .
H37 H 1.4036 0.6063 0.2223 0.030 Uiso 1 1 calc R . .
C38 C 1.5460(4) 0.62122(4) 0.3909(2) 0.0416(5) Uani 1 1 d . . .
H38A H 1.4027 0.6182 0.4178 0.062 Uiso 1 1 calc R . .
H38B H 1.5523 0.6400 0.3667 0.062 Uiso 1 1 calc R . .
H38C H 1.6823 0.6173 0.4547 0.062 Uiso 1 1 calc R . .
C39 C 1.7627(4) 0.60834(4) 0.2346(2) 0.0424(5) Uani 1 1 d . . .
H39A H 1.9061 0.6057 0.2958 0.064 Uiso 1 1 calc R . .
H39B H 1.7558 0.6270 0.2069 0.064 Uiso 1 1 calc R . .
H39C H 1.7626 0.5961 0.1691 0.064 Uiso 1 1 calc R . .
O7 O 1.2841(2) 0.43762(3) 0.50603(13) 0.0324(3) Uani 1 1 d . . .
O8 O 1.0297(2) 0.46991(2) 0.53478(11) 0.0226(2) Uani 1 1 d . . .
H8O H 0.975(6) 0.4544(7) 0.583(3) 0.067(9) Uiso 1 1 d . . .
C40 C 1.2187(3) 0.46135(3) 0.49931(13) 0.0177(3) Uani 1 1 d . . .
C41 C 1.3487(3) 0.48339(3) 0.44584(14) 0.0179(3) Uani 1 1 d . . .
H41 H 1.5114 0.4767 0.4516 0.021 Uiso 1 1 calc R . .
C42 C 1.2273(3) 0.48585(4) 0.31202(14) 0.0264(4) Uani 1 1 d . . .
H42A H 1.0632 0.4910 0.3029 0.040 Uiso 1 1 calc R . .
H42B H 1.2353 0.4685 0.2735 0.040 Uiso 1 1 calc R . .
H42C H 1.3076 0.4996 0.2762 0.040 Uiso 1 1 calc R . .
C43 C 1.3694(3) 0.51075(3) 0.51072(13) 0.0175(3) Uani 1 1 d . A .
C44 C 1.1767(3) 0.52851(3) 0.50210(14) 0.0209(3) Uani 1 1 d . . .
H44 H 1.0264 0.5234 0.4578 0.025 Uiso 1 1 calc R . .
C45 C 1.2069(3) 0.55387(4) 0.55907(15) 0.0239(3) Uani 1 1 d . A .
H45 H 1.0761 0.5655 0.5516 0.029 Uiso 1 1 calc R . .
C46 C 1.4279(3) 0.56235(3) 0.62697(14) 0.0234(3) Uani 1 1 d . . .
C47 C 1.6194(3) 0.54450(3) 0.63624(15) 0.0223(3) Uani 1 1 d . A .
H47 H 1.7691 0.5496 0.6815 0.027 Uiso 1 1 calc R . .
C48 C 1.5911(3) 0.51906(3) 0.57878(15) 0.0203(3) Uani 1 1 d . . .
H48 H 1.7222 0.5075 0.5861 0.024 Uiso 1 1 calc R A .
C49 C 1.4601(5) 0.59017(4) 0.68843(16) 0.0401(5) Uani 0.659(6) 1 d PD A 1
H49A H 1.6144 0.5972 0.6826 0.048 Uiso 0.659(6) 1 calc PR A 1
H49B H 1.3405 0.6024 0.6418 0.048 Uiso 0.659(6) 1 calc PR A 1
C50 C 1.4473(7) 0.59294(7) 0.8168(3) 0.0278(8) Uani 0.659(6) 1 d PD A 1
H50 H 1.4817 0.6120 0.8421 0.033 Uiso 0.659(6) 1 calc PR A 1
C51 C 1.1915(5) 0.58614(6) 0.8222(3) 0.0333(8) Uani 0.659(6) 1 d PD A 1
H51A H 1.1582 0.5673 0.8007 0.050 Uiso 0.659(6) 1 calc PR A 1
H51B H 1.0827 0.5977 0.7674 0.050 Uiso 0.659(6) 1 calc PR A 1
H51C H 1.1727 0.5892 0.9019 0.050 Uiso 0.659(6) 1 calc PR A 1
C52 C 1.6216(15) 0.5741(2) 0.9012(7) 0.045(3) Uani 0.659(6) 1 d PD A 1
H52A H 1.5966 0.5757 0.9805 0.068 Uiso 0.659(6) 1 calc PR A 1
H52B H 1.7823 0.5794 0.9019 0.068 Uiso 0.659(6) 1 calc PR A 1
H52C H 1.5954 0.5555 0.8745 0.068 Uiso 0.659(6) 1 calc PR A 1
C49' C 1.4601(5) 0.59017(4) 0.68843(16) 0.0401(5) Uani 0.341(6) 1 d PD A 2
H49C H 1.3609 0.6041 0.6404 0.048 Uiso 0.341(6) 1 calc PR A 2
H49D H 1.6255 0.5961 0.7059 0.048 Uiso 0.341(6) 1 calc PR A 2
C50' C 1.3721(11) 0.58363(13) 0.8118(4) 0.0219(13) Uani 0.341(6) 1 d PD A 2
H50' H 1.2379 0.5707 0.7964 0.026 Uiso 0.341(6) 1 calc PR A 2
C51' C 1.591(3) 0.5713(4) 0.8990(9) 0.029(3) Uani 0.341(6) 1 d PD A 2
H51D H 1.5603 0.5701 0.9773 0.043 Uiso 0.341(6) 1 calc PR A 2
H51E H 1.7271 0.5828 0.9018 0.043 Uiso 0.341(6) 1 calc PR A 2
H51F H 1.6214 0.5533 0.8724 0.043 Uiso 0.341(6) 1 calc PR A 2
C52' C 1.3056(12) 0.61021(12) 0.8634(5) 0.0386(17) Uani 0.341(6) 1 d PD A 2
H52D H 1.2710 0.6067 0.9396 0.058 Uiso 0.341(6) 1 calc PR A 2
H52E H 1.1673 0.6179 0.8101 0.058 Uiso 0.341(6) 1 calc PR A 2
H52F H 1.4362 0.6229 0.8732 0.058 Uiso 0.341(6) 1 calc PR A 2
N1 N 0.6415(2) 0.34068(3) 0.59194(12) 0.0195(3) Uani 1 1 d . . .
N2 N 0.8884(2) 0.43309(3) 0.15815(12) 0.0194(3) Uani 1 1 d . . .
C53 C 0.8196(3) 0.33560(3) 0.53839(14) 0.0205(3) Uani 1 1 d . . .
H53 H 0.9102 0.3198 0.5597 0.025 Uiso 1 1 calc R . .
C54 C 0.8756(3) 0.35277(3) 0.45272(14) 0.0188(3) Uani 1 1 d . . .
H54 H 0.9993 0.3483 0.4169 0.023 Uiso 1 1 calc R . .
C55 C 0.7437(3) 0.37683(3) 0.42108(13) 0.0155(3) Uani 1 1 d . . .
C56 C 0.5571(3) 0.38194(3) 0.47693(14) 0.0191(3) Uani 1 1 d . . .
H56 H 0.4635 0.3976 0.4582 0.023 Uiso 1 1 calc R . .
C57 C 0.5136(3) 0.36335(3) 0.56052(15) 0.0208(3) Uani 1 1 d . . .
H57 H 0.3883 0.3669 0.5965 0.025 Uiso 1 1 calc R . .
C58 C 1.0119(3) 0.40963(3) 0.18419(14) 0.0181(3) Uani 1 1 d . . .
H58 H 1.1294 0.4057 0.1435 0.022 Uiso 1 1 calc R . .
C59 C 0.9736(3) 0.39088(3) 0.26879(13) 0.0173(3) Uani 1 1 d . . .
H59 H 1.0632 0.3748 0.2834 0.021 Uiso 1 1 calc R . .
C60 C 0.7981(3) 0.39644(3) 0.33182(13) 0.0154(3) Uani 1 1 d . . .
C61 C 0.6755(3) 0.42134(3) 0.30651(14) 0.0197(3) Uani 1 1 d . . .
H61 H 0.5615 0.4263 0.3479 0.024 Uiso 1 1 calc R . .
C62 C 0.7243(3) 0.43857(3) 0.21974(15) 0.0211(3) Uani 1 1 d . . .
H62 H 0.6384 0.4548 0.2034 0.025 Uiso 1 1 calc R . .
N3 N 0.6415(2) 0.34201(3) 1.10720(12) 0.0184(3) Uani 1 1 d . . .
N4 N 0.8911(3) 0.43354(3) 0.67283(12) 0.0203(3) Uani 1 1 d . . .
C63 C 0.8175(3) 0.33688(3) 1.05257(15) 0.0205(3) Uani 1 1 d . . .
H63 H 0.9115 0.3214 1.0753 0.025 Uiso 1 1 calc R . .
C64 C 0.8667(3) 0.35357(3) 0.96361(14) 0.0187(3) Uani 1 1 d . . .
H64 H 0.9898 0.3491 0.9273 0.022 Uiso 1 1 calc R . .
C65 C 0.7290(3) 0.37711(3) 0.92932(13) 0.0155(3) Uani 1 1 d . . .
C66 C 0.5425(3) 0.38213(3) 0.98507(14) 0.0179(3) Uani 1 1 d . . .
H66 H 0.4442 0.3974 0.9638 0.022 Uiso 1 1 calc R . .
C67 C 0.5056(3) 0.36415(3) 1.07252(15) 0.0190(3) Uani 1 1 d . . .
H67 H 0.3805 0.3677 1.1087 0.023 Uiso 1 1 calc R . .
C68 C 1.0009(3) 0.40915(3) 0.69313(14) 0.0193(3) Uani 1 1 d . . .
H68 H 1.1145 0.4047 0.6507 0.023 Uiso 1 1 calc R . .
C69 C 0.9535(3) 0.39020(3) 0.77431(14) 0.0181(3) Uani 1 1 d . . .
H69 H 1.0330 0.3734 0.7853 0.022 Uiso 1 1 calc R . .
C70 C 0.7844(3) 0.39659(3) 0.83945(13) 0.0155(3) Uani 1 1 d . . .
C71 C 0.6732(3) 0.42213(3) 0.81910(14) 0.0192(3) Uani 1 1 d . . .
H71 H 0.5613 0.4273 0.8613 0.023 Uiso 1 1 calc R . .
C72 C 0.7308(3) 0.43967(3) 0.73550(15) 0.0212(3) Uani 1 1 d . . .
H72 H 0.6539 0.4566 0.7224 0.025 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2068(19) . ?
O2 C1 1.3227(19) . ?
O2 H2O 0.91(3) . ?
C1 C2 1.529(2) . ?
C2 C3 1.526(2) . ?
C2 C4 1.526(2) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.390(2) . ?
C4 C9 1.397(2) . ?
C5 C6 1.388(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(2) . ?
C7 C10 1.513(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.529(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.509(3) . ?
C11 C13 1.533(3) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O3 C14 1.209(2) . ?
O4 C14 1.3242(19) . ?
O4 H4O 0.85(3) . ?
C14 C15 1.529(2) . ?
C15 C17 1.524(2) . ?
C15 C16 1.528(2) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.393(2) . ?
C17 C22 1.398(2) . ?
C18 C19 1.390(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.395(2) . ?
C20 C23 1.511(2) . ?
C21 C22 1.391(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.533(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.530(3) . ?
C24 C26 1.531(3) . ?
C24 H24 0.9800 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O5 C27 1.2142(19) . ?
O6 C27 1.3210(19) . ?
O6 H6O 0.91(3) . ?
C27 C28 1.522(2) . ?
C28 C30 1.522(2) . ?
C28 C29 1.532(2) . ?
C28 H28 0.9800 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C35 1.392(2) . ?
C30 C31 1.393(2) . ?
C31 C32 1.392(2) . ?
C31 H31 0.9300 . ?
C32 C33 1.400(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.386(2) . ?
C33 C36 1.510(2) . ?
C34 C35 1.399(2) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.535(2) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C39 1.518(3) . ?
C37 C38 1.527(2) . ?
C37 H37 0.9800 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
O7 C40 1.213(2) . ?
O8 C40 1.3185(19) . ?
O8 H8O 1.03(3) . ?
C40 C41 1.520(2) . ?
C41 C43 1.518(2) . ?
C41 C42 1.539(2) . ?
C41 H41 0.9800 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C48 1.392(2) . ?
C43 C44 1.393(2) . ?
C44 C45 1.390(2) . ?
C44 H44 0.9300 . ?
C45 C46 1.391(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.389(2) . ?
C46 C49 1.520(2) . ?
C47 C48 1.396(2) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 C50 1.504(3) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C52 1.527(5) . ?
C50 C51 1.527(5) . ?
C50 H50 0.9800 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C50' C52' 1.510(6) . ?
C50' C51' 1.535(8) . ?
C50' H50' 0.9800 . ?
C51' H51D 0.9600 . ?
C51' H51E 0.9600 . ?
C51' H51F 0.9600 . ?
C52' H52D 0.9600 . ?
C52' H52E 0.9600 . ?
C52' H52F 0.9600 . ?
N1 C57 1.330(2) . ?
N1 C53 1.340(2) . ?
N2 C62 1.336(2) . ?
N2 C58 1.342(2) . ?
C53 C54 1.388(2) . ?
C53 H53 0.9300 . ?
C54 C55 1.397(2) . ?
C54 H54 0.9300 . ?
C55 C56 1.400(2) . ?
C55 C60 1.490(2) . ?
C56 C57 1.387(2) . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C58 C59 1.391(2) . ?
C58 H58 0.9300 . ?
C59 C60 1.404(2) . ?
C59 H59 0.9300 . ?
C60 C61 1.399(2) . ?
C61 C62 1.384(2) . ?
C61 H61 0.9300 . ?
C62 H62 0.9300 . ?
N3 C67 1.337(2) . ?
N3 C63 1.338(2) . ?
N4 C72 1.334(2) . ?
N4 C68 1.340(2) . ?
C63 C64 1.388(2) . ?
C63 H63 0.9300 . ?
C64 C65 1.398(2) . ?
C64 H64 0.9300 . ?
C65 C66 1.398(2) . ?
C65 C70 1.493(2) . ?
C66 C67 1.388(2) . ?
C66 H66 0.9300 . ?
C67 H67 0.9300 . ?
C68 C69 1.386(2) . ?
C68 H68 0.9300 . ?
C69 C70 1.399(2) . ?
C69 H69 0.9300 . ?
C70 C71 1.393(2) . ?
C71 C72 1.385(2) . ?
C71 H71 0.9300 . ?
C72 H72 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2O 110.4(16) . . ?
O1 C1 O2 123.95(14) . . ?
O1 C1 C2 124.64(14) . . ?
O2 C1 C2 111.41(12) . . ?
C3 C2 C4 112.14(13) . . ?
C3 C2 C1 111.03(13) . . ?
C4 C2 C1 109.77(12) . . ?
C3 C2 H2 107.9 . . ?
C4 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 117.95(14) . . ?
C5 C4 C2 120.94(14) . . ?
C9 C4 C2 121.10(13) . . ?
C6 C5 C4 121.38(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.00(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 117.64(15) . . ?
C6 C7 C10 121.73(15) . . ?
C8 C7 C10 120.61(16) . . ?
C9 C8 C7 121.31(16) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C4 120.68(15) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C7 C10 C11 114.25(15) . . ?
C7 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C7 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 111.43(17) . . ?
C12 C11 C13 110.48(17) . . ?
C10 C11 C13 109.63(18) . . ?
C12 C11 H11 108.4 . . ?
C10 C11 H11 108.4 . . ?
C13 C11 H11 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 O4 H4O 107.1(17) . . ?
O3 C14 O4 124.02(14) . . ?
O3 C14 C15 124.79(14) . . ?
O4 C14 C15 111.15(13) . . ?
C17 C15 C16 113.84(14) . . ?
C17 C15 C14 106.52(12) . . ?
C16 C15 C14 111.66(13) . . ?
C17 C15 H15 108.2 . . ?
C16 C15 H15 108.2 . . ?
C14 C15 H15 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 117.90(15) . . ?
C18 C17 C15 120.64(14) . . ?
C22 C17 C15 121.38(14) . . ?
C19 C18 C17 121.11(15) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 121.32(15) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 117.50(15) . . ?
C19 C20 C23 121.91(15) . . ?
C21 C20 C23 120.59(16) . . ?
C22 C21 C20 121.57(15) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C17 120.60(14) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C20 C23 C24 114.07(15) . . ?
C20 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
C20 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C25 C24 C26 110.75(19) . . ?
C25 C24 C23 109.7(2) . . ?
C26 C24 C23 111.1(2) . . ?
C25 C24 H24 108.4 . . ?
C26 C24 H24 108.4 . . ?
C23 C24 H24 108.4 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C27 O6 H6O 108.3(17) . . ?
O5 C27 O6 122.90(14) . . ?
O5 C27 C28 122.95(14) . . ?
O6 C27 C28 114.14(13) . . ?
C30 C28 C27 110.07(12) . . ?
C30 C28 C29 113.76(14) . . ?
C27 C28 C29 110.40(14) . . ?
C30 C28 H28 107.4 . . ?
C27 C28 H28 107.4 . . ?
C29 C28 H28 107.4 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C35 C30 C31 118.26(14) . . ?
C35 C30 C28 119.59(14) . . ?
C31 C30 C28 122.14(14) . . ?
C32 C31 C30 120.90(14) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 121.03(14) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C34 C33 C32 117.80(14) . . ?
C34 C33 C36 121.99(15) . . ?
C32 C33 C36 120.19(14) . . ?
C33 C34 C35 121.32(15) . . ?
C33 C34 H34 119.3 . . ?
C35 C34 H34 119.3 . . ?
C30 C35 C34 120.64(14) . . ?
C30 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C33 C36 C37 114.77(13) . . ?
C33 C36 H36A 108.6 . . ?
C37 C36 H36A 108.6 . . ?
C33 C36 H36B 108.6 . . ?
C37 C36 H36B 108.6 . . ?
H36A C36 H36B 107.6 . . ?
C39 C37 C38 110.48(16) . . ?
C39 C37 C36 112.01(16) . . ?
C38 C37 C36 110.49(15) . . ?
C39 C37 H37 107.9 . . ?
C38 C37 H37 107.9 . . ?
C36 C37 H37 107.9 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C40 O8 H8O 108.4(18) . . ?
O7 C40 O8 123.29(15) . . ?
O7 C40 C41 121.54(14) . . ?
O8 C40 C41 115.15(13) . . ?
C43 C41 C40 114.15(12) . . ?
C43 C41 C42 112.86(13) . . ?
C40 C41 C42 108.02(13) . . ?
C43 C41 H41 107.1 . . ?
C40 C41 H41 107.1 . . ?
C42 C41 H41 107.1 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C48 C43 C44 118.04(15) . . ?
C48 C43 C41 119.15(14) . . ?
C44 C43 C41 122.78(14) . . ?
C45 C44 C43 120.61(16) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C44 C45 C46 121.69(15) . . ?
C44 C45 H45 119.2 . . ?
C46 C45 H45 119.2 . . ?
C47 C46 C45 117.59(15) . . ?
C47 C46 C49 120.98(17) . . ?
C45 C46 C49 121.42(16) . . ?
C46 C47 C48 121.14(16) . . ?
C46 C47 H47 119.4 . . ?
C48 C47 H47 119.4 . . ?
C43 C48 C47 120.92(15) . . ?
C43 C48 H48 119.5 . . ?
C47 C48 H48 119.5 . . ?
C50 C49 C46 120.6(2) . . ?
C50 C49 H49A 107.2 . . ?
C46 C49 H49A 107.2 . . ?
C50 C49 H49B 107.2 . . ?
C46 C49 H49B 107.2 . . ?
H49A C49 H49B 106.8 . . ?
C49 C50 C52 113.2(4) . . ?
C49 C50 C51 107.0(3) . . ?
C52 C50 C51 109.9(5) . . ?
C49 C50 H50 108.9 . . ?
C52 C50 H50 108.9 . . ?
C51 C50 H50 108.9 . . ?
C52' C50' C51' 108.9(7) . . ?
C52' C50' H50' 111.0 . . ?
C51' C50' H50' 111.0 . . ?
C50' C51' H51D 109.5 . . ?
C50' C51' H51E 109.5 . . ?
H51D C51' H51E 109.5 . . ?
C50' C51' H51F 109.5 . . ?
H51D C51' H51F 109.5 . . ?
H51E C51' H51F 109.5 . . ?
C50' C52' H52D 109.5 . . ?
C50' C52' H52E 109.5 . . ?
H52D C52' H52E 109.5 . . ?
C50' C52' H52F 109.5 . . ?
H52D C52' H52F 109.5 . . ?
H52E C52' H52F 109.5 . . ?
C57 N1 C53 117.65(14) . . ?
C62 N2 C58 117.16(14) . . ?
N1 C53 C54 123.26(15) . . ?
N1 C53 H53 118.4 . . ?
C54 C53 H53 118.4 . . ?
C53 C54 C55 119.10(14) . . ?
C53 C54 H54 120.5 . . ?
C55 C54 H54 120.5 . . ?
C54 C55 C56 117.34(14) . . ?
C54 C55 C60 121.78(14) . . ?
C56 C55 C60 120.88(13) . . ?
C57 C56 C55 119.19(14) . . ?
C57 C56 H56 120.4 . . ?
C55 C56 H56 120.4 . . ?
N1 C57 C56 123.44(15) . . ?
N1 C57 H57 118.3 . . ?
C56 C57 H57 118.3 . . ?
N2 C58 C59 123.48(14) . . ?
N2 C58 H58 118.3 . . ?
C59 C58 H58 118.3 . . ?
C58 C59 C60 119.26(14) . . ?
C58 C59 H59 120.4 . . ?
C60 C59 H59 120.4 . . ?
C61 C60 C59 116.74(14) . . ?
C61 C60 C55 121.38(13) . . ?
C59 C60 C55 121.88(13) . . ?
C62 C61 C60 119.80(15) . . ?
C62 C61 H61 120.1 . . ?
C60 C61 H61 120.1 . . ?
N2 C62 C61 123.52(15) . . ?
N2 C62 H62 118.2 . . ?
C61 C62 H62 118.2 . . ?
C67 N3 C63 117.78(14) . . ?
C72 N4 C68 117.59(14) . . ?
N3 C63 C64 123.22(15) . . ?
N3 C63 H63 118.4 . . ?
C64 C63 H63 118.4 . . ?
C63 C64 C65 119.13(14) . . ?
C63 C64 H64 120.4 . . ?
C65 C64 H64 120.4 . . ?
C64 C65 C66 117.47(14) . . ?
C64 C65 C70 121.10(14) . . ?
C66 C65 C70 121.41(13) . . ?
C67 C66 C65 119.29(14) . . ?
C67 C66 H66 120.4 . . ?
C65 C66 H66 120.4 . . ?
N3 C67 C66 123.08(14) . . ?
N3 C67 H67 118.5 . . ?
C66 C67 H67 118.5 . . ?
N4 C68 C69 123.19(15) . . ?
N4 C68 H68 118.4 . . ?
C69 C68 H68 118.4 . . ?
C68 C69 C70 119.16(14) . . ?
C68 C69 H69 120.4 . . ?
C70 C69 H69 120.4 . . ?
C71 C70 C69 117.37(14) . . ?
C71 C70 C65 121.22(13) . . ?
C69 C70 C65 121.39(13) . . ?
C72 C71 C70 119.41(15) . . ?
C72 C71 H71 120.3 . . ?
C70 C71 H71 120.3 . . ?
N4 C72 C71 123.28(15) . . ?
N4 C72 H72 118.4 . . ?
C71 C72 H72 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -20.4(2) . . . . ?
O2 C1 C2 C3 160.29(13) . . . . ?
O1 C1 C2 C4 104.16(17) . . . . ?
O2 C1 C2 C4 -75.15(16) . . . . ?
C3 C2 C4 C5 -129.09(16) . . . . ?
C1 C2 C4 C5 107.00(16) . . . . ?
C3 C2 C4 C9 49.89(19) . . . . ?
C1 C2 C4 C9 -74.02(18) . . . . ?
C9 C4 C5 C6 -1.4(2) . . . . ?
C2 C4 C5 C6 177.60(15) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 1.8(2) . . . . ?
C5 C6 C7 C10 -179.42(16) . . . . ?
C6 C7 C8 C9 -1.9(2) . . . . ?
C10 C7 C8 C9 179.24(15) . . . . ?
C7 C8 C9 C4 0.5(3) . . . . ?
C5 C4 C9 C8 1.2(2) . . . . ?
C2 C4 C9 C8 -177.78(14) . . . . ?
C6 C7 C10 C11 -97.9(2) . . . . ?
C8 C7 C10 C11 80.8(2) . . . . ?
C7 C10 C11 C12 61.8(2) . . . . ?
C7 C10 C11 C13 -175.57(17) . . . . ?
O3 C14 C15 C17 102.44(17) . . . . ?
O4 C14 C15 C17 -75.02(16) . . . . ?
O3 C14 C15 C16 -22.4(2) . . . . ?
O4 C14 C15 C16 160.13(14) . . . . ?
C16 C15 C17 C18 -141.63(15) . . . . ?
C14 C15 C17 C18 94.87(17) . . . . ?
C16 C15 C17 C22 41.7(2) . . . . ?
C14 C15 C17 C22 -81.76(17) . . . . ?
C22 C17 C18 C19 0.1(2) . . . . ?
C15 C17 C18 C19 -176.60(14) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C18 C19 C20 C23 -179.70(15) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C23 C20 C21 C22 -179.88(15) . . . . ?
C20 C21 C22 C17 -0.6(2) . . . . ?
C18 C17 C22 C21 0.3(2) . . . . ?
C15 C17 C22 C21 176.99(14) . . . . ?
C19 C20 C23 C24 90.8(2) . . . . ?
C21 C20 C23 C24 -88.8(2) . . . . ?
C20 C23 C24 C25 167.23(19) . . . . ?
C20 C23 C24 C26 -69.9(2) . . . . ?
O5 C27 C28 C30 -118.02(17) . . . . ?
O6 C27 C28 C30 61.10(17) . . . . ?
O5 C27 C28 C29 115.57(18) . . . . ?
O6 C27 C28 C29 -65.31(17) . . . . ?
C27 C28 C30 C35 95.73(17) . . . . ?
C29 C28 C30 C35 -139.77(16) . . . . ?
C27 C28 C30 C31 -82.90(18) . . . . ?
C29 C28 C30 C31 41.6(2) . . . . ?
C35 C30 C31 C32 -1.2(2) . . . . ?
C28 C30 C31 C32 177.43(14) . . . . ?
C30 C31 C32 C33 -0.5(2) . . . . ?
C31 C32 C33 C34 2.1(2) . . . . ?
C31 C32 C33 C36 -176.42(14) . . . . ?
C32 C33 C34 C35 -2.1(2) . . . . ?
C36 C33 C34 C35 176.40(14) . . . . ?
C31 C30 C35 C34 1.2(2) . . . . ?
C28 C30 C35 C34 -177.45(14) . . . . ?
C33 C34 C35 C30 0.5(2) . . . . ?
C34 C33 C36 C37 109.44(18) . . . . ?
C32 C33 C36 C37 -72.1(2) . . . . ?
C33 C36 C37 C39 -69.2(2) . . . . ?
C33 C36 C37 C38 167.20(16) . . . . ?
O7 C40 C41 C43 -140.95(16) . . . . ?
O8 C40 C41 C43 40.38(19) . . . . ?
O7 C40 C41 C42 92.63(19) . . . . ?
O8 C40 C41 C42 -86.04(16) . . . . ?
C40 C41 C43 C48 108.53(16) . . . . ?
C42 C41 C43 C48 -127.62(16) . . . . ?
C40 C41 C43 C44 -73.68(19) . . . . ?
C42 C41 C43 C44 50.2(2) . . . . ?
C48 C43 C44 C45 0.6(2) . . . . ?
C41 C43 C44 C45 -177.18(14) . . . . ?
C43 C44 C45 C46 -0.5(2) . . . . ?
C44 C45 C46 C47 0.0(2) . . . . ?
C44 C45 C46 C49 179.63(15) . . . . ?
C45 C46 C47 C48 0.4(2) . . . . ?
C49 C46 C47 C48 -179.25(15) . . . . ?
C44 C43 C48 C47 -0.3(2) . . . . ?
C41 C43 C48 C47 177.65(14) . . . . ?
C46 C47 C48 C43 -0.3(2) . . . . ?
C47 C46 C49 C50 -85.5(3) . . . . ?
C45 C46 C49 C50 94.9(3) . . . . ?
C46 C49 C50 C52 55.4(6) . . . . ?
C46 C49 C50 C51 -65.9(3) . . . . ?
C57 N1 C53 C54 0.0(2) . . . . ?
N1 C53 C54 C55 1.0(2) . . . . ?
C53 C54 C55 C56 -1.2(2) . . . . ?
C53 C54 C55 C60 178.62(14) . . . . ?
C54 C55 C56 C57 0.6(2) . . . . ?
C60 C55 C56 C57 -179.30(14) . . . . ?
C53 N1 C57 C56 -0.8(2) . . . . ?
C55 C56 C57 N1 0.5(2) . . . . ?
C62 N2 C58 C59 1.5(2) . . . . ?
N2 C58 C59 C60 -0.4(2) . . . . ?
C58 C59 C60 C61 -1.5(2) . . . . ?
C58 C59 C60 C55 178.25(13) . . . . ?
C58 C59 C60 C70 -129.57(12) . . . . ?
C54 C55 C60 C61 -175.72(15) . . . . ?
C56 C55 C60 C61 4.1(2) . . . . ?
C54 C55 C60 C59 4.5(2) . . . . ?
C56 C55 C60 C59 -175.64(14) . . . . ?
C59 C60 C61 C62 2.3(2) . . . . ?
C55 C60 C61 C62 -177.51(14) . . . . ?
C58 N2 C62 C61 -0.7(2) . . . . ?
C60 C61 C62 N2 -1.2(2) . . . . ?
C67 N3 C63 C64 0.9(2) . . . . ?
N3 C63 C64 C65 0.7(2) . . . . ?
C63 C64 C65 C66 -1.8(2) . . . . ?
C63 C64 C65 C70 176.24(14) . . . . ?
C64 C65 C66 C67 1.3(2) . . . . ?
C70 C65 C66 C67 -176.71(14) . . . . ?
C63 N3 C67 C66 -1.4(2) . . . . ?
C65 C66 C67 N3 0.3(2) . . . . ?
C72 N4 C68 C69 0.8(2) . . . . ?
N4 C68 C69 C70 -0.4(2) . . . . ?
C68 C69 C70 C71 -0.4(2) . . . . ?
C68 C69 C70 C65 -179.07(14) . . . . ?
C64 C65 C70 C71 -169.58(14) . . . . ?
C66 C65 C70 C71 8.4(2) . . . . ?
C64 C65 C70 C69 9.0(2) . . . . ?
C66 C65 C70 C69 -173.03(14) . . . . ?
C69 C70 C71 C72 0.9(2) . . . . ?
C65 C70 C71 C72 179.57(14) . . . . ?
C60 C70 C71 C72 -33.16(14) . . . . ?
C68 N4 C72 C71 -0.2(2) . . . . ?
C70 C71 C72 N4 -0.6(3) . . . . ?

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
O8 H8O N4 1.03(3) 1.61(3) 2.6273(17) 172(3) .
O6 H6O N2 0.91(3) 1.78(3) 2.6622(18) 162(3) .
O4 H4O N3 0.85(3) 1.80(3) 2.6298(17) 166(2) .
O2 H2O N1 0.91(3) 1.72(3) 2.6167(18) 169(2) .

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.052

# Attachment 'solid_solution_final.cif'

data_CSS-1
_database_code_depnum_ccdc_archive 'CCDC 750023'
#TrackingRef 'solid_solution_final.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H18 O2), C10 H8 N2'
_chemical_formula_sum            'C36 H44 N2 O4'
_chemical_formula_weight         568.73
_chemical_absolute_configuration syn

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           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.7162(12)
_cell_length_b                   11.563(3)
_cell_length_c                   24.621(5)
_cell_angle_alpha                94.133(5)
_cell_angle_beta                 90.210(3)
_cell_angle_gamma                104.275(3)
_cell_volume                     1572.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4084
_cell_measurement_theta_min      2.973
_cell_measurement_theta_max      24.301

_exptl_crystal_description       'irregular plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'APEXII CCD'
_diffrn_measurement_method       omega
_diffrn_standards_number         0
_diffrn_reflns_number            14332
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         24.31
_reflns_number_total             10097
_reflns_number_gt                6344
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Apex2 v2.1-4 (Bruker, 2007)'
_computing_cell_refinement       'Apex2 v2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Apex2 v2.1-4 (Bruker, 2007)'
_computing_structure_solution    'SHELXTL 6.3.1'
_computing_structure_refinement  'SHELXTL 6.3.1'
_computing_publication_material  'SHELXTL 6.3.1'
_computing_molecular_graphics    'ORTEP-3 for Windows v2.01'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. The disordered isobutyl
groups are restrained with DFIX disances taken from a survey of isobutyl
groups from the CCDB. The methyl-methine and
methylene-methine distances were restrained to 1.52 angstroms. The
methyl-methyl distance was restrained to 2.49 angstrons. The
methyl-methylene disance was restrained to 2.51 angstroms. Additionally
the methylene carbon of the isobutyl groups was each represented as two
atoms with their positions and ADPs constrined with EXYZ and EADP cards.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.6685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    isor
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10097
_refine_ls_number_parameters     910
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1673
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.878
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001

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 0.3302(6) 0.9693(3) 0.95979(14) 0.0288(8) Uani 1 1 d . . .
O2 O 0.6491(6) 0.9485(3) 1.00696(14) 0.0301(8) Uani 1 1 d . . .
H2O H 0.6556 0.9003 0.9812 0.045 Uiso 1 1 calc R . .
C1 C 0.4620(9) 0.9937(4) 1.0000(2) 0.0211(11) Uani 1 1 d . . .
C2 C 0.4410(9) 1.0813(5) 1.0482(2) 0.0266(12) Uani 1 1 d . . .
H2 H 0.6030 1.1302 1.0585 0.032 Uiso 1 1 calc R . .
C3 C 0.2856(10) 1.1635(5) 1.0329(2) 0.0367(14) Uani 1 1 d . . .
H3A H 0.2749 1.2178 1.0636 0.055 Uiso 1 1 calc R . .
H3B H 0.1268 1.1167 1.0222 0.055 Uiso 1 1 calc R . .
H3C H 0.3567 1.2081 1.0031 0.055 Uiso 1 1 calc R . .
C4 C 0.3404(9) 1.0084(4) 1.0959(2) 0.0244(11) Uani 1 1 d . A .
C5 C 0.4921(10) 1.0102(4) 1.1397(2) 0.0294(12) Uani 1 1 d . . .
H5 H 0.6532 1.0522 1.1390 0.035 Uiso 1 1 calc R . .
C6 C 0.4027(10) 0.9481(4) 1.1858(2) 0.0342(13) Uani 1 1 d . A .
H6 H 0.5080 0.9478 1.2146 0.041 Uiso 1 1 calc R . .
C7 C 0.1619(10) 0.8878(5) 1.1890(2) 0.0341(13) Uani 1 1 d . . .
C8 C 0.0143(10) 0.8858(5) 1.1436(2) 0.0349(13) Uani 1 1 d . A .
H8 H -0.1456 0.8418 1.1433 0.042 Uiso 1 1 calc R . .
C9 C 0.1003(10) 0.9479(5) 1.0990(2) 0.0303(12) Uani 1 1 d . . .
H9 H -0.0055 0.9490 1.0703 0.036 Uiso 1 1 calc R A .
C10 C 0.0614(12) 0.8244(4) 1.2381(3) 0.0529(16) Uani 0.720(11) 1 d PD A 1
H10A H -0.0913 0.8429 1.2468 0.064 Uiso 0.720(11) 1 calc PR A 1
H10B H 0.1715 0.8540 1.2689 0.064 Uiso 0.720(11) 1 calc PR A 1
C11 C 0.0219(17) 0.6894(6) 1.2298(3) 0.069(3) Uani 0.720(11) 1 d PD A 1
H11 H -0.0709 0.6600 1.1959 0.083 Uiso 0.720(11) 1 calc PR A 1
C12 C 0.271(2) 0.6635(8) 1.2255(5) 0.099(5) Uani 0.720(11) 1 d PD A 1
H12A H 0.2546 0.5787 1.2240 0.149 Uiso 0.720(11) 1 calc PR A 1
H12B H 0.3693 0.7012 1.2567 0.149 Uiso 0.720(11) 1 calc PR A 1
H12C H 0.3468 0.6945 1.1930 0.149 Uiso 0.720(11) 1 calc PR A 1
C13 C -0.114(2) 0.6289(8) 1.2776(5) 0.104(5) Uani 0.720(11) 1 d PD A 1
H13A H -0.2750 0.6405 1.2778 0.156 Uiso 0.720(11) 1 calc PR A 1
H13B H -0.0314 0.6634 1.3111 0.156 Uiso 0.720(11) 1 calc PR A 1
H13C H -0.1222 0.5448 1.2738 0.156 Uiso 0.720(11) 1 calc PR A 1
C10' C 0.0614(12) 0.8244(4) 1.2381(3) 0.0529(16) Uani 0.280(11) 1 d PD A 2
H10C H -0.1108 0.7927 1.2316 0.064 Uiso 0.280(11) 1 calc PR A 2
H10D H 0.0810 0.8839 1.2687 0.064 Uiso 0.280(11) 1 calc PR A 2
C11' C 0.163(3) 0.7233(11) 1.2555(5) 0.054(6) Uiso 0.280(11) 1 d PD A 2
H11' H 0.3369 0.7547 1.2622 0.065 Uiso 0.280(11) 1 calc PR A 2
C12' C 0.052(4) 0.6731(15) 1.3076(5) 0.060(7) Uani 0.280(11) 1 d PD A 2
H12D H 0.0969 0.6000 1.3130 0.089 Uiso 0.280(11) 1 calc PR A 2
H12E H -0.1206 0.6575 1.3046 0.089 Uiso 0.280(11) 1 calc PR A 2
H12F H 0.1098 0.7301 1.3379 0.089 Uiso 0.280(11) 1 calc PR A 2
C13' C 0.127(4) 0.6249(13) 1.2098(6) 0.062(8) Uiso 0.280(11) 1 d PD A 2
H13D H 0.1869 0.6587 1.1766 0.094 Uiso 0.280(11) 1 calc PR A 2
H13E H -0.0423 0.5868 1.2052 0.094 Uiso 0.280(11) 1 calc PR A 2
H13F H 0.2125 0.5669 1.2187 0.094 Uiso 0.280(11) 1 calc PR A 2
O3 O 0.3318(6) 0.4803(3) 0.96124(14) 0.0305(9) Uani 1 1 d . . .
O4 O 0.6583(6) 0.4592(3) 1.00558(14) 0.0279(8) Uani 1 1 d . . .
H4O H 0.6745 0.4197 0.9774 0.042 Uiso 1 1 calc R . .
C14 C 0.4643(9) 0.4998(4) 1.0011(2) 0.0225(11) Uani 1 1 d . . .
C15 C 0.4326(10) 0.5735(5) 1.0534(2) 0.0321(13) Uani 1 1 d . . .
H15 H 0.5913 0.6232 1.0657 0.038 Uiso 1 1 calc R . .
C16 C 0.2679(10) 0.6549(5) 1.0442(3) 0.0393(15) Uani 1 1 d . . .
H16A H 0.2425 0.6955 1.0782 0.059 Uiso 1 1 calc R . .
H16B H 0.1157 0.6081 1.0292 0.059 Uiso 1 1 calc R . .
H16C H 0.3409 0.7127 1.0192 0.059 Uiso 1 1 calc R . .
C17 C 0.3403(9) 0.4848(4) 1.0957(2) 0.0269(12) Uani 1 1 d . B .
C18 C 0.5065(10) 0.4621(5) 1.1329(2) 0.0350(13) Uani 1 1 d . . .
H18 H 0.6677 0.5041 1.1327 0.042 Uiso 1 1 calc R . .
C19 C 0.4289(10) 0.3759(6) 1.1703(2) 0.0415(15) Uani 1 1 d . B .
H19 H 0.5422 0.3627 1.1947 0.050 Uiso 1 1 calc R . .
C20 C 0.1948(10) 0.3098(5) 1.1729(2) 0.0295(12) Uani 1 1 d . . .
C21 C 0.0297(10) 0.3365(5) 1.1356(2) 0.0378(14) Uani 1 1 d . B .
H21 H -0.1322 0.2959 1.1363 0.045 Uiso 1 1 calc R . .
C22 C 0.1019(10) 0.4207(5) 1.0983(2) 0.0326(13) Uani 1 1 d . . .
H22 H -0.0120 0.4348 1.0742 0.039 Uiso 1 1 calc R B .
C23 C 0.1229(10) 0.2145(5) 1.21179(17) 0.0385(14) Uani 0.634(10) 1 d PD B 1
H23A H 0.2296 0.1613 1.2066 0.046 Uiso 0.634(10) 1 calc PR B 1
H23B H -0.0387 0.1681 1.2014 0.046 Uiso 0.634(10) 1 calc PR B 1
C24 C 0.1236(15) 0.2506(7) 1.2714(3) 0.033(2) Uani 0.634(10) 1 d PD B 1
H24 H 0.2768 0.3088 1.2810 0.040 Uiso 0.634(10) 1 calc PR B 1
C25 C -0.081(2) 0.3119(11) 1.2824(4) 0.096(5) Uani 0.634(10) 1 d PD B 1
H25A H -0.2329 0.2555 1.2745 0.144 Uiso 0.634(10) 1 calc PR B 1
H25B H -0.0640 0.3775 1.2598 0.144 Uiso 0.634(10) 1 calc PR B 1
H25C H -0.0738 0.3412 1.3200 0.144 Uiso 0.634(10) 1 calc PR B 1
C26 C 0.1000(18) 0.1464(8) 1.3068(3) 0.052(3) Uani 0.634(10) 1 d PD B 1
H26A H 0.2296 0.1085 1.2996 0.078 Uiso 0.634(10) 1 calc PR B 1
H26B H -0.0516 0.0895 1.2989 0.078 Uiso 0.634(10) 1 calc PR B 1
H26C H 0.1072 0.1752 1.3445 0.078 Uiso 0.634(10) 1 calc PR B 1
C23' C 0.1229(10) 0.2145(5) 1.21179(17) 0.0385(14) Uani 0.366(10) 1 d PD B 2
H23C H 0.2605 0.1840 1.2211 0.046 Uiso 0.366(10) 1 calc PR B 2
H23D H -0.0029 0.1486 1.1956 0.046 Uiso 0.366(10) 1 calc PR B 2
C24' C 0.029(2) 0.2720(10) 1.2635(4) 0.038(5) Uiso 0.366(10) 1 d PD B 2
H24' H -0.0884 0.3149 1.2521 0.045 Uiso 0.366(10) 1 calc PR B 2
C25' C -0.098(3) 0.1740(12) 1.2992(5) 0.056(5) Uani 0.366(10) 1 d PD B 2
H25D H -0.1915 0.2065 1.3258 0.084 Uiso 0.366(10) 1 calc PR B 2
H25E H 0.0205 0.1435 1.3175 0.084 Uiso 0.366(10) 1 calc PR B 2
H25F H -0.2022 0.1103 1.2770 0.084 Uiso 0.366(10) 1 calc PR B 2
C26' C 0.229(3) 0.3598(10) 1.2960(4) 0.056(6) Uani 0.366(10) 1 d PD B 2
H26D H 0.2807 0.4313 1.2771 0.084 Uiso 0.366(10) 1 calc PR B 2
H26E H 0.3633 0.3246 1.3003 0.084 Uiso 0.366(10) 1 calc PR B 2
H26F H 0.1716 0.3793 1.3312 0.084 Uiso 0.366(10) 1 calc PR B 2
O5 O 1.3233(7) 0.1460(4) 0.73058(17) 0.0429(10) Uani 1 1 d . C .
O6 O 1.0214(7) 0.1636(3) 0.67796(15) 0.0405(10) Uani 1 1 d . C .
H6O H 1.0003 0.2098 0.7033 0.061 Uiso 1 1 calc R . .
C27 C 1.2099(12) 0.1244(5) 0.6887(2) 0.0428(16) Uani 1 1 d . . .
C28 C 1.220(2) 0.0349(10) 0.6387(5) 0.020(3) Uani 0.491(9) 1 d P C 1
H28 H 1.0570 -0.0110 0.6275 0.024 Uiso 0.491(9) 1 calc PR C 1
C29 C 1.374(2) -0.0483(9) 0.6539(4) 0.034(3) Uani 0.491(9) 1 d P C 1
H29A H 1.3072 -0.0892 0.6850 0.050 Uiso 0.491(9) 1 calc PR C 1
H29B H 1.5355 -0.0025 0.6624 0.050 Uiso 0.491(9) 1 calc PR C 1
H29C H 1.3751 -0.1057 0.6238 0.050 Uiso 0.491(9) 1 calc PR C 1
C28' C 1.348(2) 0.0632(10) 0.6456(4) 0.030(3) Uani 0.509(9) 1 d P C 2
H28' H 1.5099 0.0609 0.6579 0.036 Uiso 0.509(9) 1 calc PR C 2
C29' C 1.170(2) -0.0616(8) 0.6374(4) 0.051(3) Uani 0.509(9) 1 d P C 2
H29D H 1.2279 -0.1092 0.6095 0.076 Uiso 0.509(9) 1 calc PR C 2
H29E H 1.0139 -0.0529 0.6267 0.076 Uiso 0.509(9) 1 calc PR C 2
H29F H 1.1576 -0.1003 0.6708 0.076 Uiso 0.509(9) 1 calc PR C 2
C30 C 1.3431(14) 0.1151(6) 0.5912(2) 0.0524(18) Uani 1 1 d . . .
C31 C 1.1794(11) 0.1171(6) 0.5504(3) 0.0544(18) Uani 1 1 d . C .
H31 H 1.0178 0.0789 0.5546 0.065 Uiso 1 1 calc R . .
C32 C 1.2452(11) 0.1726(6) 0.5048(3) 0.0502(16) Uani 1 1 d . . .
H32 H 1.1293 0.1690 0.4777 0.060 Uiso 1 1 calc R C .
C33 C 1.4812(11) 0.2349(6) 0.4970(2) 0.0462(15) Uani 1 1 d . C .
C34 C 1.6456(13) 0.2381(7) 0.5384(3) 0.0597(18) Uani 1 1 d . . .
H34 H 1.8057 0.2796 0.5349 0.072 Uiso 1 1 calc R C .
C35 C 1.5758(14) 0.1809(7) 0.5846(3) 0.065(2) Uani 1 1 d . C .
H35 H 1.6892 0.1867 0.6125 0.077 Uiso 1 1 calc R . .
C36 C 1.5549(14) 0.2973(5) 0.4451(2) 0.072(2) Uani 0.640(9) 1 d PD C 1
H36A H 1.7046 0.2810 0.4323 0.086 Uiso 0.640(9) 1 calc PR C 1
H36B H 1.4314 0.2671 0.4170 0.086 Uiso 0.640(9) 1 calc PR C 1
C37 C 1.588(2) 0.4316(7) 0.4567(5) 0.079(5) Uani 0.640(9) 1 d PD C 1
H37 H 1.6790 0.4592 0.4910 0.095 Uiso 0.640(9) 1 calc PR C 1
C38 C 1.3374(19) 0.4546(9) 0.4605(5) 0.088(5) Uani 0.640(9) 1 d PD C 1
H38A H 1.2473 0.4236 0.4274 0.132 Uiso 0.640(9) 1 calc PR C 1
H38B H 1.3516 0.5391 0.4659 0.132 Uiso 0.640(9) 1 calc PR C 1
H38C H 1.2551 0.4155 0.4907 0.132 Uiso 0.640(9) 1 calc PR C 1
C39 C 1.723(2) 0.4960(9) 0.4093(5) 0.082(4) Uani 0.640(9) 1 d PD C 1
H39A H 1.6166 0.4829 0.3779 0.124 Uiso 0.640(9) 1 calc PR C 1
H39B H 1.8606 0.4652 0.4008 0.124 Uiso 0.640(9) 1 calc PR C 1
H39C H 1.7748 0.5803 0.4194 0.124 Uiso 0.640(9) 1 calc PR C 1
C36' C 1.5549(14) 0.2973(5) 0.4451(2) 0.072(2) Uani 0.360(9) 1 d PD C 2
H36C H 1.4837 0.2442 0.4139 0.086 Uiso 0.360(9) 1 calc PR C 2
H36D H 1.7290 0.3146 0.4421 0.086 Uiso 0.360(9) 1 calc PR C 2
C37' C 1.473(3) 0.4147(9) 0.4445(5) 0.046(5) Uani 0.360(9) 1 d PD C 2
H37' H 1.3088 0.4001 0.4583 0.055 Uiso 0.360(9) 1 calc PR C 2
C38' C 1.473(4) 0.4639(11) 0.3897(4) 0.086(8) Uani 0.360(9) 1 d PD C 2
H38D H 1.6206 0.4610 0.3717 0.128 Uiso 0.360(9) 1 calc PR C 2
H38E H 1.4607 0.5452 0.3942 0.128 Uiso 0.360(9) 1 calc PR C 2
H38F H 1.3384 0.4167 0.3681 0.128 Uiso 0.360(9) 1 calc PR C 2
C39' C 1.639(2) 0.5055(8) 0.4845(4) 0.036(3) Uani 0.360(9) 1 d PD C 2
H39D H 1.6034 0.5821 0.4831 0.053 Uiso 0.360(9) 1 calc PR C 2
H39E H 1.8043 0.5119 0.4750 0.053 Uiso 0.360(9) 1 calc PR C 2
H39F H 1.6142 0.4798 0.5207 0.053 Uiso 0.360(9) 1 calc PR C 2
O7 O 1.3208(7) -0.3652(3) 0.72768(16) 0.0417(10) Uani 1 1 d . C .
O8 O 1.0024(7) -0.3468(3) 0.67979(14) 0.0354(9) Uani 1 1 d . C .
H8A H 0.9919 -0.2982 0.7050 0.053 Uiso 1 1 calc R . .
C40 C 1.1999(11) -0.3831(5) 0.6862(2) 0.0362(14) Uani 1 1 d . . .
C41 C 1.219(2) -0.4607(11) 0.6326(5) 0.020(3) Uiso 0.491(9) 1 d P C 1
H41 H 1.0585 -0.5078 0.6199 0.025 Uiso 0.491(9) 1 calc PR C 1
C42 C 1.383(2) -0.5407(10) 0.6412(5) 0.039(3) Uani 0.491(9) 1 d P C 1
H42A H 1.3255 -0.5895 0.6707 0.058 Uiso 0.491(9) 1 calc PR C 1
H42B H 1.5431 -0.4929 0.6499 0.058 Uiso 0.491(9) 1 calc PR C 1
H42C H 1.3853 -0.5911 0.6086 0.058 Uiso 0.491(9) 1 calc PR C 1
C41' C 1.334(2) -0.4345(9) 0.6386(4) 0.033(3) Uani 0.509(9) 1 d P C 2
H41' H 1.4970 -0.4397 0.6489 0.040 Uiso 0.509(9) 1 calc PR C 2
C42' C 1.1604(19) -0.5585(7) 0.6211(4) 0.047(3) Uani 0.509(9) 1 d P C 2
H42D H 1.2277 -0.5964 0.5912 0.070 Uiso 0.509(9) 1 calc PR C 2
H42E H 1.0066 -0.5473 0.6102 0.070 Uiso 0.509(9) 1 calc PR C 2
H42F H 1.1398 -0.6081 0.6513 0.070 Uiso 0.509(9) 1 calc PR C 2
C43 C 1.3295(13) -0.3613(5) 0.5907(2) 0.0453(16) Uani 1 1 d . . .
C44 C 1.1663(12) -0.3455(7) 0.5549(3) 0.063(2) Uani 1 1 d . C .
H44 H 1.0098 -0.3932 0.5559 0.076 Uiso 1 1 calc R . .
C45 C 1.2163(12) -0.2634(7) 0.5169(3) 0.0559(18) Uani 1 1 d . . .
H45 H 1.0946 -0.2557 0.4933 0.067 Uiso 1 1 calc R C .
C46 C 1.4470(11) -0.1915(5) 0.5132(2) 0.0412(15) Uani 1 1 d . C .
C47 C 1.6184(13) -0.2112(6) 0.5486(2) 0.0552(18) Uani 1 1 d . . .
H47 H 1.7783 -0.1683 0.5462 0.066 Uiso 1 1 calc R C .
C48 C 1.5572(14) -0.2934(7) 0.5875(3) 0.060(2) Uani 1 1 d . C .
H48 H 1.6752 -0.3022 0.6119 0.072 Uiso 1 1 calc R . .
C49 C 1.5019(13) -0.0961(6) 0.4718(2) 0.067(2) Uani 0.518(12) 1 d PD C 1
H49A H 1.3735 -0.0546 0.4741 0.080 Uiso 0.518(12) 1 calc PR C 1
H49B H 1.6489 -0.0382 0.4845 0.080 Uiso 0.518(12) 1 calc PR C 1
C50 C 1.533(3) -0.1282(13) 0.4115(4) 0.073(7) Uani 0.518(12) 1 d PD C 1
H50 H 1.4060 -0.1994 0.3995 0.087 Uiso 0.518(12) 1 calc PR C 1
C51 C 1.514(3) -0.0260(14) 0.3777(5) 0.066(5) Uani 0.518(12) 1 d PD C 1
H51A H 1.6253 0.0463 0.3921 0.099 Uiso 0.518(12) 1 calc PR C 1
H51B H 1.3527 -0.0157 0.3790 0.099 Uiso 0.518(12) 1 calc PR C 1
H51C H 1.5529 -0.0440 0.3407 0.099 Uiso 0.518(12) 1 calc PR C 1
C52 C 1.777(2) -0.1568(13) 0.4053(4) 0.063(4) Uani 0.518(12) 1 d PD C 1
H52A H 1.7978 -0.1804 0.3678 0.094 Uiso 0.518(12) 1 calc PR C 1
H52B H 1.7845 -0.2209 0.4273 0.094 Uiso 0.518(12) 1 calc PR C 1
H52C H 1.9019 -0.0872 0.4167 0.094 Uiso 0.518(12) 1 calc PR C 1
C49' C 1.5019(13) -0.0961(6) 0.4718(2) 0.067(2) Uani 0.482(12) 1 d PD C 2
H49C H 1.3561 -0.0710 0.4641 0.080 Uiso 0.482(12) 1 calc PR C 2
H49D H 1.6215 -0.0267 0.4875 0.080 Uiso 0.482(12) 1 calc PR C 2
C50' C 1.596(3) -0.1427(12) 0.4188(4) 0.085(10) Uani 0.482(12) 1 d PD C 2
H50' H 1.7301 -0.1764 0.4288 0.102 Uiso 0.482(12) 1 calc PR C 2
C51' C 1.416(3) -0.2410(11) 0.3873(4) 0.083(6) Uani 0.482(12) 1 d PD C 2
H51D H 1.2878 -0.2099 0.3737 0.125 Uiso 0.482(12) 1 calc PR C 2
H51E H 1.3504 -0.3035 0.4107 0.125 Uiso 0.482(12) 1 calc PR C 2
H51F H 1.4937 -0.2727 0.3573 0.125 Uiso 0.482(12) 1 calc PR C 2
C52' C 1.700(5) -0.0410(14) 0.3833(5) 0.146(13) Uani 0.482(12) 1 d PD C 2
H52D H 1.7440 -0.0731 0.3489 0.220 Uiso 0.482(12) 1 calc PR C 2
H52E H 1.8410 0.0111 0.4011 0.220 Uiso 0.482(12) 1 calc PR C 2
H52F H 1.5819 0.0033 0.3776 0.220 Uiso 0.482(12) 1 calc PR C 2
N1 N 0.6996(7) 0.7797(3) 0.93358(16) 0.0208(9) Uani 1 1 d . . .
N2 N 0.9394(7) 0.3234(4) 0.75027(17) 0.0283(10) Uani 1 1 d . . .
C53 C 0.5701(9) 0.7423(4) 0.8881(2) 0.0248(12) Uani 1 1 d . . .
H53 H 0.4456 0.7778 0.8805 0.030 Uiso 1 1 calc R . .
C54 C 0.6092(8) 0.6546(4) 0.8518(2) 0.0224(11) Uani 1 1 d . . .
H54 H 0.5124 0.6314 0.8205 0.027 Uiso 1 1 calc R . .
C55 C 0.7942(8) 0.6001(4) 0.86182(19) 0.0208(11) Uani 1 1 d . . .
C56 C 0.9280(8) 0.6377(4) 0.91010(19) 0.0232(11) Uani 1 1 d . . .
H56 H 1.0506 0.6024 0.9196 0.028 Uiso 1 1 calc R . .
C57 C 0.8750(9) 0.7285(4) 0.9436(2) 0.0245(11) Uani 1 1 d . . .
H57 H 0.9687 0.7548 0.9752 0.029 Uiso 1 1 calc R . .
C58 C 0.7686(9) 0.3810(4) 0.7395(2) 0.0264(12) Uani 1 1 d . C .
H58 H 0.6812 0.3599 0.7069 0.032 Uiso 1 1 calc R . .
C59 C 0.7168(8) 0.4691(4) 0.7742(2) 0.0242(11) Uani 1 1 d . . .
H59 H 0.5943 0.5048 0.7651 0.029 Uiso 1 1 calc R C .
C60 C 0.8470(8) 0.5056(4) 0.82313(19) 0.0196(11) Uani 1 1 d . C .
C61 C 1.0271(8) 0.4467(4) 0.8342(2) 0.0201(11) Uani 1 1 d . . .
H61 H 1.1180 0.4668 0.8664 0.024 Uiso 1 1 calc R C .
C62 C 1.0699(8) 0.3576(4) 0.79661(19) 0.0230(11) Uani 1 1 d . C .
H62 H 1.1929 0.3210 0.8041 0.028 Uiso 1 1 calc R . .
N3 N 0.7099(7) 0.2910(4) 0.92992(17) 0.0234(10) Uani 1 1 d . . .
N4 N 0.9279(7) -0.1848(4) 0.75421(17) 0.0306(11) Uani 1 1 d . . .
C63 C 0.5783(9) 0.2495(4) 0.8851(2) 0.0261(12) Uani 1 1 d . . .
H63 H 0.4537 0.2845 0.8770 0.031 Uiso 1 1 calc R . .
C64 C 0.6134(8) 0.1588(4) 0.8502(2) 0.0234(11) Uani 1 1 d . . .
H64 H 0.5156 0.1340 0.8192 0.028 Uiso 1 1 calc R . .
C65 C 0.7946(8) 0.1041(5) 0.8613(2) 0.0254(12) Uani 1 1 d . . .
C66 C 0.9324(9) 0.1421(4) 0.90891(19) 0.0257(12) Uani 1 1 d . . .
H66 H 1.0512 0.1051 0.9191 0.031 Uiso 1 1 calc R . .
C67 C 0.8842(9) 0.2393(5) 0.9412(2) 0.0293(12) Uani 1 1 d . . .
H67 H 0.9807 0.2685 0.9721 0.035 Uiso 1 1 calc R . .
C68 C 0.7597(9) -0.1268(5) 0.7432(2) 0.0312(13) Uani 1 1 d . C .
H68 H 0.6696 -0.1497 0.7110 0.037 Uiso 1 1 calc R . .
C69 C 0.7128(8) -0.0368(4) 0.7761(2) 0.0269(12) Uani 1 1 d . . .
H69 H 0.5896 -0.0023 0.7663 0.032 Uiso 1 1 calc R C .
C70 C 0.8440(8) 0.0054(4) 0.82428(19) 0.0209(11) Uani 1 1 d . C .
C71 C 1.0248(9) -0.0536(4) 0.8363(2) 0.0264(12) Uani 1 1 d . . .
H71 H 1.1192 -0.0304 0.8679 0.032 Uiso 1 1 calc R C .
C72 C 1.0623(9) -0.1470(4) 0.8006(2) 0.0259(12) Uani 1 1 d . C .
H72 H 1.1832 -0.1844 0.8090 0.031 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.216(6) . ?
O2 C1 1.316(6) . ?
O2 H2O 0.8200 . ?
C1 C2 1.529(7) . ?
C2 C3 1.517(7) . ?
C2 C4 1.527(7) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.376(7) . ?
C4 C9 1.383(7) . ?
C5 C6 1.415(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(7) . ?
C7 C10 1.502(8) . ?
C8 C9 1.381(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.519(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.528(7) . ?
C11 C12 1.530(8) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11' C13' 1.517(10) . ?
C11' C12' 1.521(10) . ?
C11' H11' 0.9800 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
O3 C14 1.212(6) . ?
O4 C14 1.314(6) . ?
O4 H4O 0.8200 . ?
C14 C15 1.528(7) . ?
C15 C16 1.513(7) . ?
C15 C17 1.519(8) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.386(8) . ?
C17 C18 1.400(7) . ?
C18 C19 1.398(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.417(7) . ?
C20 C23 1.494(7) . ?
C21 C22 1.376(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.496(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C26 1.519(7) . ?
C24 C25 1.523(8) . ?
C24 H24 0.9800 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C24' C26' 1.511(9) . ?
C24' C25' 1.526(9) . ?
C24' H24' 0.9800 . ?
C25' H25D 0.9600 . ?
C25' H25E 0.9600 . ?
C25' H25F 0.9600 . ?
C26' H26D 0.9600 . ?
C26' H26E 0.9600 . ?
C26' H26F 0.9600 . ?
O5 C27 1.194(7) . ?
O6 C27 1.301(7) . ?
O6 H6O 0.8200 . ?
C27 C28' 1.555(11) . ?
C27 C28 1.559(13) . ?
C28 C29 1.516(18) . ?
C28 C30 1.603(14) . ?
C28 H28 0.9800 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C28' C30 1.511(11) . ?
C28' C29' 1.547(17) . ?
C28' H28' 0.9800 . ?
C29' H29D 0.9600 . ?
C29' H29E 0.9600 . ?
C29' H29F 0.9600 . ?
C30 C31 1.375(9) . ?
C30 C35 1.376(10) . ?
C31 C32 1.343(9) . ?
C31 H31 0.9300 . ?
C32 C33 1.385(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.376(8) . ?
C33 C36 1.522(8) . ?
C34 C35 1.369(10) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.524(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.522(9) . ?
C37 C39 1.537(9) . ?
C37 H37 0.9800 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C37' C38' 1.502(9) . ?
C37' C39' 1.525(9) . ?
C37' H37' 0.9800 . ?
C38' H38D 0.9600 . ?
C38' H38E 0.9600 . ?
C38' H38F 0.9600 . ?
C39' H39D 0.9600 . ?
C39' H39E 0.9600 . ?
C39' H39F 0.9600 . ?
O7 C40 1.207(6) . ?
O8 C40 1.310(7) . ?
O8 H8A 0.8200 . ?
C40 C41 1.560(13) . ?
C40 C41' 1.565(11) . ?
C41 C42 1.495(17) . ?
C41 C43 1.613(13) . ?
C41 H41 0.9800 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C41' C43 1.504(11) . ?
C41' C42' 1.560(14) . ?
C41' H41' 0.9800 . ?
C42' H42D 0.9600 . ?
C42' H42E 0.9600 . ?
C42' H42F 0.9600 . ?
C43 C44 1.336(9) . ?
C43 C48 1.350(9) . ?
C44 C45 1.362(9) . ?
C44 H44 0.9300 . ?
C45 C46 1.382(9) . ?
C45 H45 0.9300 . ?
C46 C47 1.379(8) . ?
C46 C49 1.532(8) . ?
C47 C48 1.384(9) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 C50 1.527(9) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C52 1.515(10) . ?
C50 C51 1.517(9) . ?
C50 H50 0.9800 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C50' C51' 1.498(9) . ?
C50' C52' 1.518(9) . ?
C50' H50' 0.9800 . ?
C51' H51D 0.9600 . ?
C51' H51E 0.9600 . ?
C51' H51F 0.9600 . ?
C52' H52D 0.9600 . ?
C52' H52E 0.9600 . ?
C52' H52F 0.9600 . ?
N1 C57 1.315(6) . ?
N1 C53 1.325(6) . ?
N2 C62 1.341(6) . ?
N2 C58 1.345(6) . ?
C53 C54 1.364(7) . ?
C53 H53 0.9300 . ?
C54 C55 1.388(7) . ?
C54 H54 0.9300 . ?
C55 C56 1.393(6) . ?
C55 C60 1.486(4) . ?
C56 C57 1.382(7) . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C58 C59 1.372(7) . ?
C58 H58 0.9300 . ?
C59 C60 1.396(6) . ?
C59 H59 0.9300 . ?
C60 C61 1.402(6) . ?
C61 C62 1.403(7) . ?
C61 H61 0.9300 . ?
C62 H62 0.9300 . ?
N3 C67 1.320(6) . ?
N3 C63 1.324(6) . ?
N4 C68 1.338(7) . ?
N4 C72 1.357(6) . ?
C63 C64 1.361(7) . ?
C63 H63 0.9300 . ?
C64 C65 1.376(7) . ?
C64 H64 0.9300 . ?
C65 C66 1.392(6) . ?
C65 C70 1.491(4) . ?
C66 C67 1.413(7) . ?
C66 H66 0.9300 . ?
C67 H67 0.9300 . ?
C68 C69 1.352(7) . ?
C68 H68 0.9300 . ?
C69 C70 1.391(6) . ?
C69 H69 0.9300 . ?
C70 C71 1.413(7) . ?
C71 C72 1.401(7) . ?
C71 H71 0.9300 . ?
C72 H72 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2O 109.5 . . ?
O1 C1 O2 123.4(5) . . ?
O1 C1 C2 125.9(4) . . ?
O2 C1 C2 110.7(4) . . ?
C3 C2 C4 112.4(4) . . ?
C3 C2 C1 110.8(4) . . ?
C4 C2 C1 107.9(4) . . ?
C3 C2 H2 108.5 . . ?
C4 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 118.5(5) . . ?
C5 C4 C2 118.3(5) . . ?
C9 C4 C2 123.1(5) . . ?
C4 C5 C6 119.9(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 121.7(5) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 116.9(5) . . ?
C6 C7 C10 122.6(5) . . ?
C8 C7 C10 120.5(6) . . ?
C9 C8 C7 121.4(5) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C4 121.4(5) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C7 C10 C11 113.0(5) . . ?
C7 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C7 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C13 110.5(6) . . ?
C10 C11 C12 107.1(6) . . ?
C13 C11 C12 110.7(6) . . ?
C10 C11 H11 109.5 . . ?
C13 C11 H11 109.5 . . ?
C12 C11 H11 109.5 . . ?
C13' C11' C12' 110.3(9) . . ?
C13' C11' H11' 108.0 . . ?
C12' C11' H11' 108.0 . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C11' C13' H13D 109.5 . . ?
C11' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C11' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C14 O4 H4O 109.5 . . ?
O3 C14 O4 124.2(5) . . ?
O3 C14 C15 125.9(4) . . ?
O4 C14 C15 109.9(4) . . ?
C16 C15 C17 113.2(5) . . ?
C16 C15 C14 111.6(4) . . ?
C17 C15 C14 106.6(4) . . ?
C16 C15 H15 108.4 . . ?
C17 C15 H15 108.4 . . ?
C14 C15 H15 108.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 117.7(5) . . ?
C22 C17 C15 123.8(5) . . ?
C18 C17 C15 118.5(5) . . ?
C19 C18 C17 119.7(5) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 123.6(5) . . ?
C20 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?
C19 C20 C21 115.4(5) . . ?
C19 C20 C23 121.6(5) . . ?
C21 C20 C23 122.9(5) . . ?
C22 C21 C20 122.0(5) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C17 121.6(5) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
C20 C23 C24 118.8(5) . . ?
C20 C23 H23A 107.6 . . ?
C24 C23 H23A 107.6 . . ?
C20 C23 H23B 107.6 . . ?
C24 C23 H23B 107.6 . . ?
H23A C23 H23B 107.0 . . ?
C23 C24 C26 113.1(6) . . ?
C23 C24 C25 108.8(6) . . ?
C26 C24 C25 110.2(6) . . ?
C23 C24 H24 108.2 . . ?
C26 C24 H24 108.2 . . ?
C25 C24 H24 108.2 . . ?
C26' C24' C25' 109.7(8) . . ?
C26' C24' H24' 108.4 . . ?
C25' C24' H24' 108.4 . . ?
C24' C25' H25D 109.5 . . ?
C24' C25' H25E 109.5 . . ?
H25D C25' H25E 109.5 . . ?
C24' C25' H25F 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 109.5 . . ?
C24' C26' H26D 109.5 . . ?
C24' C26' H26E 109.5 . . ?
H26D C26' H26E 109.5 . . ?
C24' C26' H26F 109.5 . . ?
H26D C26' H26F 109.5 . . ?
H26E C26' H26F 109.5 . . ?
C27 O6 H6O 109.5 . . ?
O5 C27 O6 124.8(5) . . ?
O5 C27 C28' 109.6(7) . . ?
O6 C27 C28' 124.7(6) . . ?
O5 C27 C28 131.2(7) . . ?
O6 C27 C28 103.5(7) . . ?
C28' C27 C28 27.4(4) . . ?
C29 C28 C27 109.1(8) . . ?
C29 C28 C30 110.4(10) . . ?
C27 C28 C30 106.0(7) . . ?
C29 C28 H28 110.4 . . ?
C27 C28 H28 110.4 . . ?
C30 C28 H28 110.4 . . ?
C30 C28' C29' 103.9(9) . . ?
C30 C28' C27 110.8(7) . . ?
C29' C28' C27 99.9(8) . . ?
C30 C28' H28' 113.7 . . ?
C29' C28' H28' 113.7 . . ?
C27 C28' H28' 113.7 . . ?
C28' C29' H29D 109.5 . . ?
C28' C29' H29E 109.5 . . ?
H29D C29' H29E 109.5 . . ?
C28' C29' H29F 109.5 . . ?
H29D C29' H29F 109.5 . . ?
H29E C29' H29F 109.5 . . ?
C31 C30 C35 116.3(6) . . ?
C31 C30 C28' 138.9(8) . . ?
C35 C30 C28' 104.8(7) . . ?
C31 C30 C28 111.7(8) . . ?
C35 C30 C28 131.9(7) . . ?
C28' C30 C28 27.2(4) . . ?
C32 C31 C30 122.1(6) . . ?
C32 C31 H31 118.9 . . ?
C30 C31 H31 118.9 . . ?
C31 C32 C33 121.7(6) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C34 C33 C32 117.0(6) . . ?
C34 C33 C36 121.6(6) . . ?
C32 C33 C36 121.5(6) . . ?
C35 C34 C33 120.6(7) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C30 122.1(7) . . ?
C34 C35 H35 119.0 . . ?
C30 C35 H35 119.0 . . ?
C37 C36 C33 109.4(6) . . ?
C37 C36 H36A 109.8 . . ?
C33 C36 H36A 109.8 . . ?
C37 C36 H36B 109.8 . . ?
C33 C36 H36B 109.8 . . ?
H36A C36 H36B 108.2 . . ?
C38 C37 C36 107.3(7) . . ?
C38 C37 C39 109.8(8) . . ?
C36 C37 C39 108.8(7) . . ?
C38 C37 H37 110.3 . . ?
C36 C37 H37 110.3 . . ?
C39 C37 H37 110.3 . . ?
C38' C37' C39' 110.4(8) . . ?
C38' C37' H37' 108.0 . . ?
C39' C37' H37' 108.0 . . ?
C37' C38' H38D 109.5 . . ?
C37' C38' H38E 109.5 . . ?
H38D C38' H38E 109.5 . . ?
C37' C38' H38F 109.5 . . ?
H38D C38' H38F 109.5 . . ?
H38E C38' H38F 109.5 . . ?
C37' C39' H39D 109.5 . . ?
C37' C39' H39E 109.5 . . ?
H39D C39' H39E 109.5 . . ?
C37' C39' H39F 109.5 . . ?
H39D C39' H39F 109.5 . . ?
H39E C39' H39F 109.5 . . ?
C40 O8 H8A 109.5 . . ?
O7 C40 O8 124.4(5) . . ?
O7 C40 C41 130.5(7) . . ?
O8 C40 C41 104.9(6) . . ?
O7 C40 C41' 110.6(6) . . ?
O8 C40 C41' 124.2(6) . . ?
C41 C40 C41' 24.6(5) . . ?
C42 C41 C40 110.4(9) . . ?
C42 C41 C43 111.7(9) . . ?
C40 C41 C43 102.7(7) . . ?
C42 C41 H41 110.6 . . ?
C40 C41 H41 110.6 . . ?
C43 C41 H41 110.6 . . ?
C43 C41' C42' 104.4(8) . . ?
C43 C41' C40 107.7(7) . . ?
C42' C41' C40 103.7(8) . . ?
C43 C41' H41' 113.4 . . ?
C42' C41' H41' 113.4 . . ?
C40 C41' H41' 113.4 . . ?
C41' C42' H42D 109.5 . . ?
C41' C42' H42E 109.5 . . ?
H42D C42' H42E 109.5 . . ?
C41' C42' H42F 109.5 . . ?
H42D C42' H42F 109.5 . . ?
H42E C42' H42F 109.5 . . ?
C44 C43 C48 117.1(6) . . ?
C44 C43 C41' 137.5(8) . . ?
C48 C43 C41' 105.3(7) . . ?
C44 C43 C41 113.3(8) . . ?
C48 C43 C41 129.6(7) . . ?
C41' C43 C41 24.3(5) . . ?
C43 C44 C45 123.7(7) . . ?
C43 C44 H44 118.1 . . ?
C45 C44 H44 118.1 . . ?
C44 C45 C46 120.3(6) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C47 C46 C45 116.2(6) . . ?
C47 C46 C49 123.4(6) . . ?
C45 C46 C49 120.5(6) . . ?
C46 C47 C48 121.3(7) . . ?
C46 C47 H47 119.4 . . ?
C48 C47 H47 119.4 . . ?
C43 C48 C47 121.3(6) . . ?
C43 C48 H48 119.3 . . ?
C47 C48 H48 119.3 . . ?
C50 C49 C46 121.8(7) . . ?
C50 C49 H49A 106.9 . . ?
C46 C49 H49A 106.9 . . ?
C50 C49 H49B 106.9 . . ?
C46 C49 H49B 106.9 . . ?
H49A C49 H49B 106.7 . . ?
C52 C50 C51 111.1(9) . . ?
C52 C50 C49 107.8(8) . . ?
C51 C50 C49 110.8(8) . . ?
C52 C50 H50 109.0 . . ?
C51 C50 H50 109.0 . . ?
C49 C50 H50 109.0 . . ?
C51' C50' C52' 111.0(9) . . ?
C51' C50' H50' 106.6 . . ?
C52' C50' H50' 106.6 . . ?
C50' C51' H51D 109.5 . . ?
C50' C51' H51E 109.5 . . ?
H51D C51' H51E 109.5 . . ?
C50' C51' H51F 109.5 . . ?
H51D C51' H51F 109.5 . . ?
H51E C51' H51F 109.5 . . ?
C50' C52' H52D 109.5 . . ?
C50' C52' H52E 109.5 . . ?
H52D C52' H52E 109.5 . . ?
C50' C52' H52F 109.5 . . ?
H52D C52' H52F 109.5 . . ?
H52E C52' H52F 109.5 . . ?
C57 N1 C53 117.3(4) . . ?
C62 N2 C58 117.6(4) . . ?
N1 C53 C54 123.7(4) . . ?
N1 C53 H53 118.2 . . ?
C54 C53 H53 118.2 . . ?
C53 C54 C55 119.6(5) . . ?
C53 C54 H54 120.2 . . ?
C55 C54 H54 120.2 . . ?
C54 C55 C56 116.9(5) . . ?
C54 C55 C60 121.7(4) . . ?
C56 C55 C60 121.4(3) . . ?
C57 C56 C55 118.7(4) . . ?
C57 C56 H56 120.7 . . ?
C55 C56 H56 120.7 . . ?
N1 C57 C56 123.8(5) . . ?
N1 C57 H57 118.1 . . ?
C56 C57 H57 118.1 . . ?
N2 C58 C59 123.5(5) . . ?
N2 C58 H58 118.3 . . ?
C59 C58 H58 118.3 . . ?
C58 C59 C60 120.3(4) . . ?
C58 C59 H59 119.9 . . ?
C60 C59 H59 119.9 . . ?
C59 C60 C61 116.4(5) . . ?
C59 C60 C55 121.7(3) . . ?
C61 C60 C55 121.9(3) . . ?
C59 C60 C70 84.0(3) . . ?
C62 C61 C60 120.0(5) . . ?
C62 C61 H61 120.0 . . ?
C60 C61 H61 120.0 . . ?
N2 C62 C61 122.2(5) . . ?
N2 C62 H62 118.9 . . ?
C61 C62 H62 118.9 . . ?
C67 N3 C63 117.1(4) . . ?
C68 N4 C72 116.9(5) . . ?
N3 C63 C64 124.3(4) . . ?
N3 C63 H63 117.9 . . ?
C64 C63 H63 117.9 . . ?
C63 C64 C65 119.5(5) . . ?
C63 C64 H64 120.3 . . ?
C65 C64 H64 120.3 . . ?
C64 C65 C66 118.2(5) . . ?
C64 C65 C70 122.0(4) . . ?
C66 C65 C70 119.8(4) . . ?
C65 C66 C67 117.3(5) . . ?
C65 C66 H66 121.4 . . ?
C67 C66 H66 121.4 . . ?
N3 C67 C66 123.6(5) . . ?
N3 C67 H67 118.2 . . ?
C66 C67 H67 118.2 . . ?
N4 C68 C69 124.0(5) . . ?
N4 C68 H68 118.0 . . ?
C69 C68 H68 118.0 . . ?
C68 C69 C70 121.7(5) . . ?
C68 C69 H69 119.1 . . ?
C70 C69 H69 119.1 . . ?
C69 C70 C71 115.2(5) . . ?
C69 C70 C65 122.6(4) . . ?
C71 C70 C65 122.2(3) . . ?
C72 C71 C70 120.1(5) . . ?
C72 C71 H71 119.9 . . ?
C70 C71 H71 119.9 . . ?
N4 C72 C71 122.1(5) . . ?
N4 C72 H72 119.0 . . ?
C71 C72 H72 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -17.6(7) . . . . ?
O2 C1 C2 C3 160.8(4) . . . . ?
O1 C1 C2 C4 105.8(6) . . . . ?
O2 C1 C2 C4 -75.7(5) . . . . ?
C3 C2 C4 C5 -128.0(5) . . . . ?
C1 C2 C4 C5 109.5(5) . . . . ?
C3 C2 C4 C9 47.2(7) . . . . ?
C1 C2 C4 C9 -75.3(6) . . . . ?
C9 C4 C5 C6 1.8(7) . . . . ?
C2 C4 C5 C6 177.2(5) . . . . ?
C4 C5 C6 C7 -2.1(8) . . . . ?
C5 C6 C7 C8 3.2(8) . . . . ?
C5 C6 C7 C10 -178.2(5) . . . . ?
C6 C7 C8 C9 -4.2(8) . . . . ?
C10 C7 C8 C9 177.1(5) . . . . ?
C7 C8 C9 C4 4.2(8) . . . . ?
C5 C4 C9 C8 -2.8(7) . . . . ?
C2 C4 C9 C8 -178.0(5) . . . . ?
C6 C7 C10 C11 -103.1(7) . . . . ?
C8 C7 C10 C11 75.5(7) . . . . ?
C7 C10 C11 C13 -171.6(8) . . . . ?
C7 C10 C11 C12 67.8(9) . . . . ?
O3 C14 C15 C16 -19.4(8) . . . . ?
O4 C14 C15 C16 160.9(4) . . . . ?
O3 C14 C15 C17 104.6(6) . . . . ?
O4 C14 C15 C17 -75.1(5) . . . . ?
C16 C15 C17 C22 43.8(7) . . . . ?
C14 C15 C17 C22 -79.3(6) . . . . ?
C16 C15 C17 C18 -139.2(5) . . . . ?
C14 C15 C17 C18 97.8(6) . . . . ?
C22 C17 C18 C19 0.8(8) . . . . ?
C15 C17 C18 C19 -176.4(5) . . . . ?
C17 C18 C19 C20 0.4(9) . . . . ?
C18 C19 C20 C21 -1.7(9) . . . . ?
C18 C19 C20 C23 177.0(5) . . . . ?
C19 C20 C21 C22 1.8(8) . . . . ?
C23 C20 C21 C22 -176.8(5) . . . . ?
C20 C21 C22 C17 -0.7(8) . . . . ?
C18 C17 C22 C21 -0.6(8) . . . . ?
C15 C17 C22 C21 176.4(5) . . . . ?
C19 C20 C23 C24 70.0(8) . . . . ?
C21 C20 C23 C24 -111.4(7) . . . . ?
C20 C23 C24 C26 -167.7(6) . . . . ?
C20 C23 C24 C25 69.5(9) . . . . ?
O5 C27 C28 C29 11.5(15) . . . . ?
O6 C27 C28 C29 -160.7(9) . . . . ?
C28' C27 C28 C29 55.4(13) . . . . ?
O5 C27 C28 C30 -107.4(9) . . . . ?
O6 C27 C28 C30 80.4(8) . . . . ?
C28' C27 C28 C30 -63.5(13) . . . . ?
O5 C27 C28' C30 -136.3(8) . . . . ?
O6 C27 C28' C30 33.2(12) . . . . ?
C28 C27 C28' C30 77.4(15) . . . . ?
O5 C27 C28' C29' 114.7(8) . . . . ?
O6 C27 C28' C29' -75.9(9) . . . . ?
C28 C27 C28' C29' -31.7(12) . . . . ?
C29' C28' C30 C31 38.0(12) . . . . ?
C27 C28' C30 C31 -68.5(13) . . . . ?
C29' C28' C30 C35 -144.6(7) . . . . ?
C27 C28' C30 C35 108.9(8) . . . . ?
C29' C28' C30 C28 33.5(13) . . . . ?
C27 C28' C30 C28 -72.9(13) . . . . ?
C29 C28 C30 C31 133.1(8) . . . . ?
C27 C28 C30 C31 -108.9(8) . . . . ?
C29 C28 C30 C35 -47.6(12) . . . . ?
C27 C28 C30 C35 70.3(11) . . . . ?
C29 C28 C30 C28' -50.0(14) . . . . ?
C27 C28 C30 C28' 67.9(12) . . . . ?
C35 C30 C31 C32 4.9(10) . . . . ?
C28' C30 C31 C32 -177.9(8) . . . . ?
C28 C30 C31 C32 -175.7(7) . . . . ?
C30 C31 C32 C33 -2.5(11) . . . . ?
C31 C32 C33 C34 -0.3(10) . . . . ?
C31 C32 C33 C36 179.8(6) . . . . ?
C32 C33 C34 C35 0.5(10) . . . . ?
C36 C33 C34 C35 -179.7(6) . . . . ?
C33 C34 C35 C30 2.1(11) . . . . ?
C31 C30 C35 C34 -4.7(10) . . . . ?
C28' C30 C35 C34 177.2(7) . . . . ?
C28 C30 C35 C34 176.1(8) . . . . ?
C34 C33 C36 C37 -75.8(9) . . . . ?
C32 C33 C36 C37 104.0(8) . . . . ?
C33 C36 C37 C38 -75.5(10) . . . . ?
C33 C36 C37 C39 165.7(8) . . . . ?
O7 C40 C41 C42 13.3(13) . . . . ?
O8 C40 C41 C42 -160.7(8) . . . . ?
C41' C40 C41 C42 54.7(14) . . . . ?
O7 C40 C41 C43 -106.0(8) . . . . ?
O8 C40 C41 C43 80.0(8) . . . . ?
C41' C40 C41 C43 -64.5(14) . . . . ?
O7 C40 C41' C43 -129.8(7) . . . . ?
O8 C40 C41' C43 40.1(11) . . . . ?
C41 C40 C41' C43 82.7(16) . . . . ?
O7 C40 C41' C42' 119.9(7) . . . . ?
O8 C40 C41' C42' -70.2(8) . . . . ?
C41 C40 C41' C42' -27.5(13) . . . . ?
C42' C41' C43 C44 39.5(13) . . . . ?
C40 C41' C43 C44 -70.2(12) . . . . ?
C42' C41' C43 C48 -143.2(7) . . . . ?
C40 C41' C43 C48 107.0(8) . . . . ?
C42' C41' C43 C41 34.0(13) . . . . ?
C40 C41' C43 C41 -75.7(16) . . . . ?
C42 C41 C43 C44 137.3(9) . . . . ?
C40 C41 C43 C44 -104.4(8) . . . . ?
C42 C41 C43 C48 -43.3(13) . . . . ?
C40 C41 C43 C48 75.0(10) . . . . ?
C42 C41 C43 C41' -46.8(13) . . . . ?
C40 C41 C43 C41' 71.6(15) . . . . ?
C48 C43 C44 C45 -1.8(11) . . . . ?
C41' C43 C44 C45 175.2(8) . . . . ?
C41 C43 C44 C45 177.6(8) . . . . ?
C43 C44 C45 C46 0.9(11) . . . . ?
C44 C45 C46 C47 2.0(10) . . . . ?
C44 C45 C46 C49 -177.9(6) . . . . ?
C45 C46 C47 C48 -3.8(9) . . . . ?
C49 C46 C47 C48 176.0(6) . . . . ?
C44 C43 C48 C47 -0.1(10) . . . . ?
C41' C43 C48 C47 -178.0(7) . . . . ?
C41 C43 C48 C47 -179.4(7) . . . . ?
C46 C47 C48 C43 2.9(10) . . . . ?
C47 C46 C49 C50 102.4(9) . . . . ?
C45 C46 C49 C50 -77.8(9) . . . . ?
C46 C49 C50 C52 -74.4(12) . . . . ?
C46 C49 C50 C51 163.8(9) . . . . ?
C57 N1 C53 C54 0.0(7) . . . . ?
N1 C53 C54 C55 -0.3(8) . . . . ?
C53 C54 C55 C56 1.4(7) . . . . ?
C53 C54 C55 C60 -178.9(4) . . . . ?
C54 C55 C56 C57 -2.2(7) . . . . ?
C60 C55 C56 C57 178.1(4) . . . . ?
C53 N1 C57 C56 -1.0(7) . . . . ?
C55 C56 C57 N1 2.1(8) . . . . ?
C62 N2 C58 C59 -2.3(8) . . . . ?
N2 C58 C59 C60 1.4(8) . . . . ?
C58 C59 C60 C61 -0.6(7) . . . . ?
C58 C59 C60 C55 -179.5(4) . . . . ?
C58 C59 C60 C70 -36.0(4) . . . . ?
C54 C55 C60 C59 1.6(5) . . . . ?
C56 C55 C60 C59 -178.7(6) . . . . ?
C54 C55 C60 C61 -177.2(6) . . . . ?
C56 C55 C60 C61 2.4(5) . . . . ?
C59 C60 C61 C62 0.7(7) . . . . ?
C55 C60 C61 C62 179.7(4) . . . . ?
C58 N2 C62 C61 2.5(7) . . . . ?
C60 C61 C62 N2 -1.8(7) . . . . ?
C67 N3 C63 C64 -0.7(8) . . . . ?
N3 C63 C64 C65 0.6(8) . . . . ?
C63 C64 C65 C66 1.6(7) . . . . ?
C63 C64 C65 C70 -179.2(4) . . . . ?
C64 C65 C66 C67 -3.4(7) . . . . ?
C70 C65 C66 C67 177.4(4) . . . . ?
C63 N3 C67 C66 -1.3(8) . . . . ?
C65 C66 C67 N3 3.4(8) . . . . ?
C72 N4 C68 C69 -2.1(8) . . . . ?
N4 C68 C69 C70 2.0(9) . . . . ?
C68 C69 C70 C71 -1.0(7) . . . . ?
C68 C69 C70 C65 -179.7(4) . . . . ?
C64 C65 C70 C69 0.7(5) . . . . ?
C66 C65 C70 C69 179.9(6) . . . . ?
C64 C65 C70 C71 -178.0(6) . . . . ?
C66 C65 C70 C71 1.3(5) . . . . ?
C69 C70 C71 C72 0.3(7) . . . . ?
C65 C70 C71 C72 179.1(4) . . . . ?
C68 N4 C72 C71 1.4(7) . . . . ?
C70 C71 C72 N4 -0.6(7) . . . . ?

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
O8 H8A N4 0.82 1.83 2.637(6) 170.3 .
O6 H6O N2 0.82 1.79 2.600(5) 170.9 .
O4 H4O N3 0.82 1.88 2.665(5) 160.7 .
O2 H2O N1 0.82 1.82 2.633(5) 168.8 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.31
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053


