# Electronic Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2012
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
#######################################################################
data_zhang-2
_database_code_depnum_ccdc_archive 'CCDC 890802'
#TrackingRef '12462_web_deposit_cif_file_0_JerryPJasinski_1341625892.Zhang-2-jpj.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(3aS,3cS,6aR,7S,9S,9aR)-methyl 2,5-diethyl-7,9-di(furan-2-yl)-
1,3,4,6-tetraoxododecahydro-1H-dipyrrolo[3,4-a:3',4'-f]
pyrrolizine-3b-carboxylate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C25 H25 N3 O8'
_chemical_formula_sum 'C25 H25 N3 O8'
_chemical_formula_weight 495.48
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 10.8016(4)
_cell_length_b 23.0207(5)
_cell_length_c 9.9117(3)
_cell_angle_alpha 90.0
_cell_angle_beta 111.566(4)
_cell_angle_gamma 90.0
_cell_volume 2292.11(13)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 4165
_cell_measurement_theta_min 3.8372
_cell_measurement_theta_max 71.3483
_exptl_crystal_description needle
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.04
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.436
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1040
_exptl_absorpt_coefficient_mu 0.910
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.83712
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details
;
Oxford Diffraction, (2010), CrysAlisPro, Agilent Technologies.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 16.1500
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 11211
_diffrn_reflns_av_R_equivalents 0.0335
_diffrn_reflns_av_sigmaI/netI 0.0417
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -28
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 3.84
_diffrn_reflns_theta_max 71.48
_reflns_number_total 4254
_reflns_number_gt 3402
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_cell_refinement 'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2010)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Bruker, 2000)'
_computing_publication_material 'SHELXTL (Bruker, 2000)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0852P)^2^+0.9234P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4254
_refine_ls_number_parameters 328
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0756
_refine_ls_R_factor_gt 0.0537
_refine_ls_wR_factor_ref 0.1588
_refine_ls_wR_factor_gt 0.1484
_refine_ls_goodness_of_fit_ref 1.067
_refine_ls_restrained_S_all 1.067
_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 0.35755(18) 0.88300(8) 0.61085(18) 0.0438(5) Uani 1 1 d . . .
O2 O 0.15294(17) 0.87193(7) 0.61657(17) 0.0377(4) Uani 1 1 d . . .
O3 O 0.18396(19) 0.99783(7) 0.59138(18) 0.0422(5) Uani 1 1 d . . .
O4 O 0.07031(17) 1.06882(7) 0.13437(17) 0.0351(4) Uani 1 1 d . . .
O5 O -0.15310(17) 0.86000(8) 0.22748(19) 0.0412(4) Uani 1 1 d . . .
O6 O 0.09695(19) 0.78395(7) -0.01075(19) 0.0424(4) Uani 1 1 d . . .
O7 O 0.24167(16) 0.99037(7) 0.00365(17) 0.0340(4) Uani 1 1 d . . .
O8 O 0.39203(19) 0.77305(8) 0.1818(2) 0.0480(5) Uani 1 1 d . . .
N1 N 0.1405(2) 1.04494(8) 0.3752(2) 0.0315(4) Uani 1 1 d . . .
N2 N 0.25270(18) 0.90037(8) 0.31049(19) 0.0274(4) Uani 1 1 d . . .
N3 N -0.0512(2) 0.82126(8) 0.0818(2) 0.0317(4) Uani 1 1 d . . .
C1 C 0.1818(2) 0.93515(9) 0.1778(2) 0.0265(5) Uani 1 1 d . . .
H1 H 0.1423 0.9088 0.0953 0.032 Uiso 1 1 calc R . .
C2 C 0.0678(2) 0.96764(9) 0.2099(2) 0.0274(5) Uani 1 1 d . . .
H2 H -0.0197 0.9589 0.1362 0.033 Uiso 1 1 calc R . .
C3 C 0.0906(2) 1.03258(10) 0.2286(2) 0.0294(5) Uani 1 1 d . . .
C4 C 0.1427(2) 0.99722(10) 0.4608(2) 0.0307(5) Uani 1 1 d . . .
C5 C 0.0776(2) 0.94661(9) 0.3600(2) 0.0284(5) Uani 1 1 d . . .
H5 H -0.0109 0.9384 0.3613 0.034 Uiso 1 1 calc R . .
C6 C 0.1621(2) 0.89144(10) 0.3888(2) 0.0289(5) Uani 1 1 d . . .
C7 C 0.0825(2) 0.83394(10) 0.3265(2) 0.0309(5) Uani 1 1 d . . .
H7 H 0.0779 0.8097 0.4059 0.037 Uiso 1 1 calc R . .
C8 C -0.0547(2) 0.84133(10) 0.2114(3) 0.0317(5) Uani 1 1 d . . .
C9 C 0.0725(2) 0.80130(9) 0.0917(3) 0.0331(5) Uani 1 1 d . . .
C10 C 0.1645(2) 0.80337(10) 0.2502(2) 0.0328(5) Uani 1 1 d . . .
H10 H 0.1873 0.7639 0.2882 0.039 Uiso 1 1 calc R . .
C11 C 0.2923(2) 0.84086(10) 0.2891(2) 0.0318(5) Uani 1 1 d . . .
H11 H 0.3501 0.8277 0.3858 0.038 Uiso 1 1 calc R . .
C12 C 0.2392(2) 0.88228(10) 0.5518(2) 0.0323(5) Uani 1 1 d . . .
C13 C 0.2098(3) 0.86846(13) 0.7730(3) 0.0481(7) Uani 1 1 d . . .
H13A H 0.2774 0.8390 0.8016 0.072 Uiso 1 1 calc R . .
H13B H 0.1413 0.8588 0.8094 0.072 Uiso 1 1 calc R . .
H13C H 0.2484 0.9052 0.8120 0.072 Uiso 1 1 calc R . .
C14 C 0.1866(3) 1.10271(10) 0.4363(3) 0.0366(6) Uani 1 1 d . . .
H14A H 0.1715 1.1071 0.5264 0.044 Uiso 1 1 calc R . .
H14B H 0.1348 1.1322 0.3693 0.044 Uiso 1 1 calc R . .
C15 C 0.3316(3) 1.11187(12) 0.4647(4) 0.0599(9) Uani 1 1 d . . .
H15A H 0.3830 1.0821 0.5287 0.090 Uiso 1 1 calc R . .
H15B H 0.3587 1.1492 0.5088 0.090 Uiso 1 1 calc R . .
H15C H 0.3459 1.1102 0.3747 0.090 Uiso 1 1 calc R . .
C16 C -0.1703(3) 0.81674(11) -0.0508(3) 0.0383(6) Uani 1 1 d . . .
H16A H -0.1458 0.8211 -0.1350 0.046 Uiso 1 1 calc R . .
H16B H -0.2322 0.8476 -0.0526 0.046 Uiso 1 1 calc R . .
C17 C -0.2370(3) 0.75794(12) -0.0564(3) 0.0493(7) Uani 1 1 d . . .
H17A H -0.1777 0.7276 -0.0612 0.074 Uiso 1 1 calc R . .
H17B H -0.3175 0.7562 -0.1407 0.074 Uiso 1 1 calc R . .
H17C H -0.2577 0.7530 0.0292 0.074 Uiso 1 1 calc R . .
C18 C 0.2759(2) 0.97526(9) 0.1462(2) 0.0285(5) Uani 1 1 d . . .
C19 C 0.3861(2) 1.00409(10) 0.2283(3) 0.0356(5) Uani 1 1 d . . .
H19 H 0.4292 1.0015 0.3284 0.043 Uiso 1 1 calc R . .
C20 C 0.4240(3) 1.03952(11) 0.1314(3) 0.0431(6) Uani 1 1 d . . .
H20 H 0.4968 1.0644 0.1563 0.052 Uiso 1 1 calc R . .
C21 C 0.3352(3) 1.03005(11) -0.0011(3) 0.0420(6) Uani 1 1 d . . .
H21 H 0.3362 1.0477 -0.0850 0.050 Uiso 1 1 calc R . .
C22 C 0.3711(2) 0.83111(11) 0.1952(3) 0.0345(5) Uani 1 1 d . . .
C23 C 0.4372(3) 0.86161(13) 0.1289(3) 0.0480(7) Uani 1 1 d . . .
H23 H 0.4411 0.9019 0.1239 0.058 Uiso 1 1 calc R . .
C24 C 0.5007(3) 0.82092(14) 0.0673(3) 0.0529(7) Uani 1 1 d . . .
H24 H 0.5532 0.8294 0.0136 0.064 Uiso 1 1 calc R . .
C25 C 0.4705(3) 0.76877(14) 0.1014(3) 0.0492(7) Uani 1 1 d . . .
H25 H 0.4988 0.7340 0.0744 0.059 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0448(11) 0.0507(12) 0.0317(9) -0.0004(8) 0.0090(8) 0.0004(8)
O2 0.0534(10) 0.0350(10) 0.0265(9) 0.0023(7) 0.0167(7) -0.0024(7)
O3 0.0703(12) 0.0275(9) 0.0294(10) -0.0037(7) 0.0189(8) -0.0002(8)
O4 0.0469(10) 0.0219(8) 0.0360(9) 0.0050(7) 0.0145(7) 0.0029(7)
O5 0.0432(10) 0.0391(10) 0.0449(10) -0.0088(8) 0.0205(8) -0.0033(8)
O6 0.0595(11) 0.0329(10) 0.0413(10) -0.0129(8) 0.0263(8) -0.0063(8)
O7 0.0421(9) 0.0311(9) 0.0315(9) 0.0047(7) 0.0169(7) -0.0001(7)
O8 0.0504(11) 0.0316(10) 0.0650(13) -0.0073(9) 0.0248(9) 0.0072(8)
N1 0.0449(11) 0.0197(10) 0.0318(10) -0.0030(7) 0.0164(8) -0.0002(8)
N2 0.0366(10) 0.0201(9) 0.0263(10) 0.0012(7) 0.0125(8) 0.0031(7)
N3 0.0435(11) 0.0218(10) 0.0307(10) -0.0024(7) 0.0146(8) -0.0052(8)
C1 0.0343(11) 0.0182(11) 0.0256(11) -0.0010(8) 0.0094(8) 0.0004(8)
C2 0.0332(11) 0.0190(11) 0.0299(12) 0.0000(8) 0.0115(9) 0.0000(8)
C3 0.0328(11) 0.0231(12) 0.0331(12) 0.0008(9) 0.0131(9) 0.0017(9)
C4 0.0426(13) 0.0223(12) 0.0313(13) -0.0022(9) 0.0183(10) 0.0011(9)
C5 0.0361(12) 0.0205(11) 0.0309(12) -0.0008(8) 0.0149(9) -0.0007(9)
C6 0.0378(12) 0.0222(11) 0.0283(12) -0.0009(8) 0.0140(9) -0.0012(9)
C7 0.0443(13) 0.0210(11) 0.0296(12) 0.0023(9) 0.0162(10) -0.0003(9)
C8 0.0449(13) 0.0189(11) 0.0345(13) -0.0015(9) 0.0184(10) -0.0060(9)
C9 0.0495(14) 0.0169(11) 0.0371(13) -0.0038(9) 0.0208(11) -0.0063(9)
C10 0.0465(13) 0.0195(11) 0.0355(13) 0.0032(9) 0.0186(10) 0.0032(9)
C11 0.0410(12) 0.0238(12) 0.0295(12) 0.0037(9) 0.0116(9) 0.0048(9)
C12 0.0487(14) 0.0207(11) 0.0293(12) 0.0001(9) 0.0163(10) 0.0010(9)
C13 0.0730(19) 0.0463(16) 0.0274(13) 0.0012(11) 0.0214(12) -0.0070(13)
C14 0.0554(15) 0.0192(12) 0.0368(13) -0.0056(9) 0.0188(11) -0.0015(10)
C15 0.0555(17) 0.0293(15) 0.088(2) -0.0211(15) 0.0182(16) -0.0052(12)
C16 0.0473(14) 0.0310(13) 0.0338(13) -0.0041(10) 0.0117(10) -0.0056(10)
C17 0.0521(16) 0.0340(15) 0.0564(17) -0.0094(12) 0.0136(13) -0.0114(12)
C18 0.0383(12) 0.0195(11) 0.0301(11) 0.0014(8) 0.0155(9) 0.0038(9)
C19 0.0401(13) 0.0285(13) 0.0372(13) -0.0036(9) 0.0129(10) 0.0001(10)
C20 0.0430(14) 0.0322(14) 0.0595(17) -0.0013(12) 0.0253(12) -0.0076(11)
C21 0.0498(15) 0.0333(14) 0.0529(16) 0.0108(11) 0.0306(13) -0.0011(11)
C22 0.0372(12) 0.0306(13) 0.0321(12) -0.0036(9) 0.0086(9) 0.0068(9)
C23 0.0562(17) 0.0371(15) 0.0604(18) 0.0026(12) 0.0326(14) 0.0099(12)
C24 0.0568(17) 0.058(2) 0.0544(18) 0.0026(14) 0.0327(14) 0.0173(14)
C25 0.0410(14) 0.0531(19) 0.0516(17) -0.0188(13) 0.0146(12) 0.0119(12)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.195(3) . ?
O2 C12 1.333(3) . ?
O2 C13 1.445(3) . ?
O3 C4 1.204(3) . ?
O4 C3 1.211(3) . ?
O5 C8 1.210(3) . ?
O6 C9 1.207(3) . ?
O7 C18 1.368(3) . ?
O7 C21 1.376(3) . ?
O8 C25 1.364(3) . ?
O8 C22 1.370(3) . ?
N1 C3 1.381(3) . ?
N1 C4 1.383(3) . ?
N1 C14 1.470(3) . ?
N2 C6 1.470(3) . ?
N2 C11 1.474(3) . ?
N2 C1 1.489(3) . ?
N3 C8 1.380(3) . ?
N3 C9 1.382(3) . ?
N3 C16 1.466(3) . ?
C1 C18 1.489(3) . ?
C1 C2 1.571(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.515(3) . ?
C2 C5 1.530(3) . ?
C2 H2 0.9800 . ?
C4 C5 1.528(3) . ?
C5 C6 1.528(3) . ?
C5 H5 0.9800 . ?
C6 C12 1.535(3) . ?
C6 C7 1.575(3) . ?
C7 C8 1.512(3) . ?
C7 C10 1.531(3) . ?
C7 H7 0.9800 . ?
C9 C10 1.520(3) . ?
C10 C11 1.552(3) . ?
C10 H10 0.9800 . ?
C11 C22 1.491(3) . ?
C11 H11 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.502(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.525(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.345(3) . ?
C19 C20 1.430(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.329(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.334(4) . ?
C23 C24 1.424(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.320(4) . ?
C24 H24 0.9300 . ?
C25 H25 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
C12 O2 C13 115.5(2) . . ?
C18 O7 C21 106.31(19) . . ?
C25 O8 C22 106.7(2) . . ?
C3 N1 C4 113.22(18) . . ?
C3 N1 C14 124.19(19) . . ?
C4 N1 C14 122.60(19) . . ?
C6 N2 C11 103.36(17) . . ?
C6 N2 C1 108.41(17) . . ?
C11 N2 C1 117.06(17) . . ?
C8 N3 C9 113.7(2) . . ?
C8 N3 C16 122.9(2) . . ?
C9 N3 C16 123.2(2) . . ?
C18 C1 N2 110.49(17) . . ?
C18 C1 C2 113.21(17) . . ?
N2 C1 C2 105.30(17) . . ?
C18 C1 H1 109.2 . . ?
N2 C1 H1 109.2 . . ?
C2 C1 H1 109.2 . . ?
C3 C2 C5 104.11(17) . . ?
C3 C2 C1 112.96(18) . . ?
C5 C2 C1 105.48(17) . . ?
C3 C2 H2 111.3 . . ?
C5 C2 H2 111.3 . . ?
C1 C2 H2 111.3 . . ?
O4 C3 N1 124.0(2) . . ?
O4 C3 C2 127.6(2) . . ?
N1 C3 C2 108.34(18) . . ?
O3 C4 N1 124.5(2) . . ?
O3 C4 C5 127.7(2) . . ?
N1 C4 C5 107.69(19) . . ?
C4 C5 C6 114.30(18) . . ?
C4 C5 C2 104.21(17) . . ?
C6 C5 C2 105.56(17) . . ?
C4 C5 H5 110.8 . . ?
C6 C5 H5 110.8 . . ?
C2 C5 H5 110.8 . . ?
N2 C6 C5 104.63(17) . . ?
N2 C6 C12 111.48(18) . . ?
C5 C6 C12 111.50(18) . . ?
N2 C6 C7 106.49(17) . . ?
C5 C6 C7 114.99(18) . . ?
C12 C6 C7 107.67(18) . . ?
C8 C7 C10 105.28(18) . . ?
C8 C7 C6 116.33(18) . . ?
C10 C7 C6 104.39(18) . . ?
C8 C7 H7 110.2 . . ?
C10 C7 H7 110.2 . . ?
C6 C7 H7 110.2 . . ?
O5 C8 N3 124.6(2) . . ?
O5 C8 C7 127.3(2) . . ?
N3 C8 C7 108.1(2) . . ?
O6 C9 N3 123.7(2) . . ?
O6 C9 C10 128.2(2) . . ?
N3 C9 C10 108.11(19) . . ?
C9 C10 C7 104.38(19) . . ?
C9 C10 C11 117.26(19) . . ?
C7 C10 C11 104.18(18) . . ?
C9 C10 H10 110.2 . . ?
C7 C10 H10 110.2 . . ?
C11 C10 H10 110.2 . . ?
N2 C11 C22 119.5(2) . . ?
N2 C11 C10 105.88(18) . . ?
C22 C11 C10 114.92(19) . . ?
N2 C11 H11 105.1 . . ?
C22 C11 H11 105.1 . . ?
C10 C11 H11 105.1 . . ?
O1 C12 O2 125.3(2) . . ?
O1 C12 C6 125.6(2) . . ?
O2 C12 C6 109.08(19) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 112.1(2) . . ?
N1 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 110.0(2) . . ?
N3 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
N3 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 O7 110.1(2) . . ?
C19 C18 C1 134.4(2) . . ?
O7 C18 C1 115.38(19) . . ?
C18 C19 C20 106.4(2) . . ?
C18 C19 H19 126.8 . . ?
C20 C19 H19 126.8 . . ?
C21 C20 C19 106.8(2) . . ?
C21 C20 H20 126.6 . . ?
C19 C20 H20 126.6 . . ?
C20 C21 O7 110.3(2) . . ?
C20 C21 H21 124.8 . . ?
O7 C21 H21 124.8 . . ?
C23 C22 O8 109.2(2) . . ?
C23 C22 C11 139.5(2) . . ?
O8 C22 C11 111.1(2) . . ?
C22 C23 C24 107.1(3) . . ?
C22 C23 H23 126.4 . . ?
C24 C23 H23 126.4 . . ?
C25 C24 C23 106.6(3) . . ?
C25 C24 H24 126.7 . . ?
C23 C24 H24 126.7 . . ?
C24 C25 O8 110.4(2) . . ?
C24 C25 H25 124.8 . . ?
O8 C25 H25 124.8 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 C1 C18 144.71(17) . . . . ?
C11 N2 C1 C18 -99.0(2) . . . . ?
C6 N2 C1 C2 22.1(2) . . . . ?
C11 N2 C1 C2 138.46(18) . . . . ?
C18 C1 C2 C3 -10.2(3) . . . . ?
N2 C1 C2 C3 110.57(19) . . . . ?
C18 C1 C2 C5 -123.31(19) . . . . ?
N2 C1 C2 C5 -2.5(2) . . . . ?
C4 N1 C3 O4 174.0(2) . . . . ?
C14 N1 C3 O4 -5.7(4) . . . . ?
C4 N1 C3 C2 -6.1(3) . . . . ?
C14 N1 C3 C2 174.1(2) . . . . ?
C5 C2 C3 O4 -166.6(2) . . . . ?
C1 C2 C3 O4 79.5(3) . . . . ?
C5 C2 C3 N1 13.6(2) . . . . ?
C1 C2 C3 N1 -100.3(2) . . . . ?
C3 N1 C4 O3 178.8(2) . . . . ?
C14 N1 C4 O3 -1.4(4) . . . . ?
C3 N1 C4 C5 -4.2(3) . . . . ?
C14 N1 C4 C5 175.5(2) . . . . ?
O3 C4 C5 C6 -56.0(3) . . . . ?
N1 C4 C5 C6 127.1(2) . . . . ?
O3 C4 C5 C2 -170.7(2) . . . . ?
N1 C4 C5 C2 12.4(2) . . . . ?
C3 C2 C5 C4 -15.3(2) . . . . ?
C1 C2 C5 C4 103.86(18) . . . . ?
C3 C2 C5 C6 -136.03(18) . . . . ?
C1 C2 C5 C6 -16.9(2) . . . . ?
C11 N2 C6 C5 -157.90(17) . . . . ?
C1 N2 C6 C5 -33.0(2) . . . . ?
C11 N2 C6 C12 81.5(2) . . . . ?
C1 N2 C6 C12 -153.67(17) . . . . ?
C11 N2 C6 C7 -35.7(2) . . . . ?
C1 N2 C6 C7 89.16(19) . . . . ?
C4 C5 C6 N2 -83.5(2) . . . . ?
C2 C5 C6 N2 30.5(2) . . . . ?
C4 C5 C6 C12 37.2(3) . . . . ?
C2 C5 C6 C12 151.09(19) . . . . ?
C4 C5 C6 C7 160.10(19) . . . . ?
C2 C5 C6 C7 -86.0(2) . . . . ?
N2 C6 C7 C8 -97.9(2) . . . . ?
C5 C6 C7 C8 17.5(3) . . . . ?
C12 C6 C7 C8 142.4(2) . . . . ?
N2 C6 C7 C10 17.6(2) . . . . ?
C5 C6 C7 C10 132.97(19) . . . . ?
C12 C6 C7 C10 -102.1(2) . . . . ?
C9 N3 C8 O5 -179.0(2) . . . . ?
C16 N3 C8 O5 -4.2(3) . . . . ?
C9 N3 C8 C7 -0.7(2) . . . . ?
C16 N3 C8 C7 174.07(19) . . . . ?
C10 C7 C8 O5 174.6(2) . . . . ?
C6 C7 C8 O5 -70.4(3) . . . . ?
C10 C7 C8 N3 -3.6(2) . . . . ?
C6 C7 C8 N3 111.4(2) . . . . ?
C8 N3 C9 O6 -177.3(2) . . . . ?
C16 N3 C9 O6 7.9(3) . . . . ?
C8 N3 C9 C10 4.8(3) . . . . ?
C16 N3 C9 C10 -169.94(19) . . . . ?
O6 C9 C10 C7 175.5(2) . . . . ?
N3 C9 C10 C7 -6.7(2) . . . . ?
O6 C9 C10 C11 60.9(3) . . . . ?
N3 C9 C10 C11 -121.3(2) . . . . ?
C8 C7 C10 C9 6.1(2) . . . . ?
C6 C7 C10 C9 -116.92(19) . . . . ?
C8 C7 C10 C11 129.63(18) . . . . ?
C6 C7 C10 C11 6.6(2) . . . . ?
C6 N2 C11 C22 171.90(19) . . . . ?
C1 N2 C11 C22 52.8(3) . . . . ?
C6 N2 C11 C10 40.3(2) . . . . ?
C1 N2 C11 C10 -78.8(2) . . . . ?
C9 C10 C11 N2 85.9(2) . . . . ?
C7 C10 C11 N2 -28.8(2) . . . . ?
C9 C10 C11 C22 -48.3(3) . . . . ?
C7 C10 C11 C22 -163.02(19) . . . . ?
C13 O2 C12 O1 7.8(3) . . . . ?
C13 O2 C12 C6 -173.74(19) . . . . ?
N2 C6 C12 O1 1.1(3) . . . . ?
C5 C6 C12 O1 -115.4(3) . . . . ?
C7 C6 C12 O1 117.6(3) . . . . ?
N2 C6 C12 O2 -177.36(18) . . . . ?
C5 C6 C12 O2 66.1(2) . . . . ?
C7 C6 C12 O2 -60.9(2) . . . . ?
C3 N1 C14 C15 -89.4(3) . . . . ?
C4 N1 C14 C15 90.9(3) . . . . ?
C8 N3 C16 C17 -87.9(3) . . . . ?
C9 N3 C16 C17 86.4(3) . . . . ?
C21 O7 C18 C19 0.1(2) . . . . ?
C21 O7 C18 C1 176.12(19) . . . . ?
N2 C1 C18 C19 -32.0(3) . . . . ?
C2 C1 C18 C19 85.8(3) . . . . ?
N2 C1 C18 O7 153.21(18) . . . . ?
C2 C1 C18 O7 -89.0(2) . . . . ?
O7 C18 C19 C20 -0.1(3) . . . . ?
C1 C18 C19 C20 -175.1(2) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 O7 -0.1(3) . . . . ?
C18 O7 C21 C20 0.0(3) . . . . ?
C25 O8 C22 C23 -1.6(3) . . . . ?
C25 O8 C22 C11 -176.73(19) . . . . ?
N2 C11 C22 C23 10.5(5) . . . . ?
C10 C11 C22 C23 138.1(3) . . . . ?
N2 C11 C22 O8 -176.59(19) . . . . ?
C10 C11 C22 O8 -49.0(3) . . . . ?
O8 C22 C23 C24 1.4(3) . . . . ?
C11 C22 C23 C24 174.4(3) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C23 C24 C25 O8 -0.3(3) . . . . ?
C22 O8 C25 C24 1.2(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
C2 H2 O4 0.98 2.61 3.291(3) 126.7 3_575
C2 H2 O7 0.98 2.57 3.375(3) 139.6 3_575
C5 H5 O3 0.98 2.55 3.295(3) 132.5 3_576
C7 H7 O6 0.98 2.29 3.131(3) 143.1 4_576
C20 H20 O1 0.93 2.57 3.293(3) 135.1 3_676
_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full 67.50
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max 0.316
_refine_diff_density_min -0.281
_refine_diff_density_rms 0.060
data_zang-4
_database_code_depnum_ccdc_archive 'CCDC 890803'
#TrackingRef '12463_web_deposit_cif_file_1_JerryPJasinski_1341625892.Zang-4-jpj-3.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C27 H26 N4 O8 S, C H2 Cl2'
_chemical_formula_sum 'C28 H28 Cl2 N4 O8 S'
_chemical_formula_weight 651.50
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 11.5934(4)
_cell_length_b 23.9267(7)
_cell_length_c 12.5474(5)
_cell_angle_alpha 90.00
_cell_angle_beta 116.043(4)
_cell_angle_gamma 90.00
_cell_volume 3127.15(21)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 7050
_cell_measurement_theta_min 3.6916
_cell_measurement_theta_max 71.3802
_exptl_crystal_description rod
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.384
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1352
_exptl_absorpt_coefficient_mu 2.956
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.59701
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_process_details
;
Oxford Diffraction (2010),
CrysAlisPro, Agilent Technologies
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 1.5418
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 16.1500
_diffrn_reflns_number 20917
_diffrn_reflns_av_R_equivalents 0.0365
_diffrn_reflns_av_sigmaI/netI 0.0302
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -29
_diffrn_reflns_limit_k_max 29
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 3.69
_diffrn_reflns_theta_max 71.51
_reflns_number_total 6023
_reflns_number_gt 5127
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_cell_refinement 'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2010)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Bruker, 2000)'
_computing_publication_material 'SHELXTL (Bruker, 2000)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+2.4122P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 6023
_refine_ls_number_parameters 391
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0608
_refine_ls_R_factor_gt 0.0526
_refine_ls_wR_factor_ref 0.1510
_refine_ls_wR_factor_gt 0.1436
_refine_ls_goodness_of_fit_ref 1.045
_refine_ls_restrained_S_all 1.045
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.28131(9) 0.37289(4) 0.22252(9) 0.0725(3) Uani 1 1 d . . .
Cl2 Cl 0.03138(10) 0.42058(4) 0.07170(14) 0.1029(5) Uani 1 1 d . . .
S1 S 0.57710(7) 0.06484(3) 0.04501(7) 0.0525(2) Uani 1 1 d . . .
O1 O 0.4269(3) -0.13108(8) 0.3667(2) 0.0656(7) Uani 1 1 d . . .
O2 O 0.2845(4) -0.12471(9) 0.1879(3) 0.0918(10) Uani 1 1 d . . .
O3 O 0.81368(15) 0.21615(7) 0.28181(16) 0.0375(4) Uani 1 1 d . . .
O4 O 0.52357(15) 0.28778(7) 0.39551(14) 0.0334(4) Uani 1 1 d . . .
O5 O 0.19522(14) 0.18042(6) -0.00700(13) 0.0297(3) Uani 1 1 d . . .
O6 O 0.26121(15) 0.26815(7) -0.01121(14) 0.0318(4) Uani 1 1 d . . .
O7 O 0.08644(14) 0.23229(7) 0.13698(14) 0.0332(4) Uani 1 1 d . . .
O8 O 0.26101(16) 0.08732(7) 0.39057(16) 0.0375(4) Uani 1 1 d . . .
N1 N 0.3668(3) -0.10430(9) 0.2762(3) 0.0550(7) Uani 1 1 d . . .
N2 N 0.68616(16) 0.24796(7) 0.36581(15) 0.0248(4) Uani 1 1 d . . .
N3 N 0.42391(16) 0.15612(7) 0.17301(14) 0.0199(3) Uani 1 1 d . . .
N4 N 0.14762(17) 0.15240(8) 0.24935(16) 0.0265(4) Uani 1 1 d . . .
C1 C 0.52234(19) 0.16229(8) 0.12814(18) 0.0228(4) Uani 1 1 d . . .
H1 H 0.4743 0.1632 0.0415 0.027 Uiso 1 1 calc R . .
C2 C 0.5809(2) 0.22246(8) 0.16489(18) 0.0234(4) Uani 1 1 d . . .
H2 H 0.5854 0.2411 0.0973 0.028 Uiso 1 1 calc R . .
C3 C 0.7085(2) 0.22718(9) 0.2734(2) 0.0261(4) Uani 1 1 d . . .
C4 C 0.5619(2) 0.26525(8) 0.33040(18) 0.0239(4) Uani 1 1 d . . .
C5 C 0.48574(19) 0.25322(8) 0.19897(17) 0.0219(4) Uani 1 1 d . . .
H5 H 0.4568 0.2881 0.1540 0.026 Uiso 1 1 calc R . .
C6 C 0.37130(19) 0.21208(8) 0.16743(17) 0.0197(4) Uani 1 1 d . . .
C7 C 0.31248(19) 0.21165(8) 0.25651(17) 0.0207(4) Uani 1 1 d . . .
H7 H 0.3343 0.2463 0.3029 0.025 Uiso 1 1 calc R . .
C8 C 0.16931(19) 0.20144(9) 0.20395(18) 0.0241(4) Uani 1 1 d . . .
C9 C 0.2588(2) 0.12777(9) 0.33208(19) 0.0264(4) Uani 1 1 d . . .
C10 C 0.37336(19) 0.16128(8) 0.33820(17) 0.0214(4) Uani 1 1 d . . .
H10 H 0.4253 0.1741 0.4196 0.026 Uiso 1 1 calc R . .
C11 C 0.46080(19) 0.13096(8) 0.29042(17) 0.0205(4) Uani 1 1 d . . .
H11 H 0.5510 0.1397 0.3420 0.025 Uiso 1 1 calc R . .
C12 C 0.4431(2) 0.06819(8) 0.28094(19) 0.0242(4) Uani 1 1 d . . .
C13 C 0.5253(2) 0.03366(10) 0.3716(2) 0.0308(5) Uani 1 1 d . . .
H13 H 0.5965 0.0490 0.4344 0.037 Uiso 1 1 calc R . .
C14 C 0.5028(3) -0.02309(10) 0.3697(2) 0.0371(6) Uani 1 1 d . . .
H14 H 0.5576 -0.0462 0.4304 0.045 Uiso 1 1 calc R . .
C15 C 0.3967(3) -0.04443(9) 0.2753(2) 0.0384(6) Uani 1 1 d . . .
C16 C 0.3160(3) -0.01205(10) 0.1813(2) 0.0392(6) Uani 1 1 d . . .
H16 H 0.2472 -0.0279 0.1172 0.047 Uiso 1 1 calc R . .
C17 C 0.3401(2) 0.04468(9) 0.1846(2) 0.0307(5) Uani 1 1 d . . .
H17 H 0.2870 0.0673 0.1219 0.037 Uiso 1 1 calc R . .
C18 C 0.6114(2) 0.11325(9) 0.1549(2) 0.0273(5) Uani 1 1 d . . .
C19 C 0.7180(2) 0.09597(9) 0.2633(2) 0.0302(5) Uani 1 1 d . . .
H19 H 0.7533 0.1162 0.3336 0.036 Uiso 1 1 calc R . .
C20 C 0.7606(3) 0.04226(12) 0.2445(3) 0.0507(7) Uani 1 1 d . . .
H20 H 0.8286 0.0233 0.3036 0.061 Uiso 1 1 calc R . .
C21 C 0.6944(3) 0.02149(12) 0.1345(4) 0.0581(9) Uani 1 1 d . . .
H21 H 0.7114 -0.0130 0.1105 0.070 Uiso 1 1 calc R . .
C22 C 0.0180(2) 0.13145(11) 0.2198(2) 0.0368(5) Uani 1 1 d . . .
H22A H -0.0379 0.1627 0.2140 0.044 Uiso 1 1 calc R . .
H22B H 0.0211 0.1071 0.2828 0.044 Uiso 1 1 calc R . .
C23 C -0.0362(3) 0.09992(15) 0.1048(3) 0.0608(9) Uani 1 1 d . . .
H23A H -0.0344 0.1232 0.0433 0.091 Uiso 1 1 calc R . .
H23B H -0.1233 0.0894 0.0848 0.091 Uiso 1 1 calc R . .
H23C H 0.0142 0.0670 0.1129 0.091 Uiso 1 1 calc R . .
C24 C 0.27072(19) 0.22437(9) 0.03954(18) 0.0230(4) Uani 1 1 d . . .
C25 C 0.0866(2) 0.18956(12) -0.1213(2) 0.0396(6) Uani 1 1 d . . .
H25A H 0.0369 0.2206 -0.1158 0.059 Uiso 1 1 calc R . .
H25B H 0.0339 0.1566 -0.1441 0.059 Uiso 1 1 calc R . .
H25C H 0.1169 0.1975 -0.1796 0.059 Uiso 1 1 calc R . .
C26 C 0.7876(2) 0.25585(10) 0.4863(2) 0.0329(5) Uani 1 1 d . . .
H26A H 0.7635 0.2858 0.5246 0.039 Uiso 1 1 calc R . .
H26B H 0.8664 0.2666 0.4827 0.039 Uiso 1 1 calc R . .
C27 C 0.8105(3) 0.20332(11) 0.5588(2) 0.0406(6) Uani 1 1 d . . .
H27A H 0.7326 0.1927 0.5628 0.061 Uiso 1 1 calc R . .
H27B H 0.8765 0.2099 0.6375 0.061 Uiso 1 1 calc R . .
H27C H 0.8369 0.1739 0.5224 0.061 Uiso 1 1 calc R . .
C28 C 0.1456(4) 0.37065(15) 0.0838(3) 0.0636(9) Uani 1 1 d . . .
H28A H 0.1724 0.3767 0.0216 0.076 Uiso 1 1 calc R . .
H28B H 0.1070 0.3338 0.0723 0.076 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0674(5) 0.0660(5) 0.0808(6) 0.0073(4) 0.0294(5) 0.0077(4)
Cl2 0.0568(5) 0.0503(5) 0.1701(13) -0.0222(6) 0.0210(6) 0.0029(4)
S1 0.0493(4) 0.0407(4) 0.0682(5) -0.0229(3) 0.0265(4) -0.0013(3)
O1 0.0898(17) 0.0279(10) 0.0950(18) 0.0252(11) 0.0552(15) 0.0169(10)
O2 0.153(3) 0.0279(11) 0.0834(19) -0.0110(11) 0.042(2) -0.0232(14)
O3 0.0227(8) 0.0451(10) 0.0467(10) -0.0078(8) 0.0172(7) -0.0034(7)
O4 0.0270(8) 0.0441(9) 0.0287(8) -0.0130(7) 0.0119(7) -0.0033(7)
O5 0.0260(8) 0.0307(8) 0.0218(7) -0.0002(6) 0.0009(6) -0.0039(6)
O6 0.0307(8) 0.0317(8) 0.0265(8) 0.0096(6) 0.0065(7) 0.0018(6)
O7 0.0210(7) 0.0382(9) 0.0357(9) 0.0081(7) 0.0082(7) 0.0074(6)
O8 0.0378(9) 0.0338(9) 0.0481(10) 0.0147(7) 0.0255(8) 0.0045(7)
N1 0.089(2) 0.0213(11) 0.0713(18) 0.0006(11) 0.0505(17) 0.0019(12)
N2 0.0190(8) 0.0294(9) 0.0235(9) -0.0030(7) 0.0070(7) -0.0038(7)
N3 0.0197(8) 0.0204(8) 0.0192(8) 0.0022(6) 0.0081(7) 0.0017(6)
N4 0.0212(9) 0.0300(9) 0.0286(9) -0.0004(7) 0.0112(7) -0.0018(7)
C1 0.0232(10) 0.0241(10) 0.0218(10) -0.0011(8) 0.0107(8) -0.0017(8)
C2 0.0255(11) 0.0236(10) 0.0230(10) 0.0003(8) 0.0124(9) -0.0024(8)
C3 0.0229(11) 0.0246(10) 0.0315(11) -0.0024(8) 0.0126(9) -0.0042(8)
C4 0.0221(10) 0.0224(10) 0.0254(10) -0.0015(8) 0.0088(8) -0.0035(8)
C5 0.0219(10) 0.0207(9) 0.0221(10) 0.0013(7) 0.0087(8) -0.0008(8)
C6 0.0194(9) 0.0191(9) 0.0185(9) 0.0013(7) 0.0065(8) 0.0003(7)
C7 0.0200(10) 0.0201(9) 0.0202(9) 0.0002(7) 0.0073(8) 0.0009(7)
C8 0.0214(10) 0.0290(10) 0.0220(10) -0.0019(8) 0.0097(8) 0.0013(8)
C9 0.0275(11) 0.0259(10) 0.0281(11) 0.0017(8) 0.0144(9) 0.0025(8)
C10 0.0210(10) 0.0235(9) 0.0186(9) 0.0007(7) 0.0077(8) 0.0025(8)
C11 0.0173(9) 0.0230(10) 0.0188(9) 0.0013(7) 0.0057(8) 0.0012(7)
C12 0.0263(10) 0.0233(10) 0.0253(10) 0.0039(8) 0.0134(9) 0.0049(8)
C13 0.0312(11) 0.0302(11) 0.0312(12) 0.0067(9) 0.0140(10) 0.0066(9)
C14 0.0455(14) 0.0291(12) 0.0431(14) 0.0139(10) 0.0253(12) 0.0148(10)
C15 0.0605(16) 0.0191(11) 0.0471(14) 0.0020(10) 0.0341(13) 0.0047(10)
C16 0.0542(16) 0.0287(12) 0.0348(13) -0.0055(10) 0.0197(12) -0.0054(11)
C17 0.0370(12) 0.0242(11) 0.0281(11) 0.0026(8) 0.0117(10) 0.0016(9)
C18 0.0272(11) 0.0244(10) 0.0353(12) -0.0030(9) 0.0182(9) -0.0022(8)
C19 0.0292(11) 0.0221(10) 0.0511(14) 0.0045(9) 0.0286(11) 0.0048(8)
C20 0.0364(14) 0.0386(15) 0.083(2) 0.0172(14) 0.0310(15) 0.0114(12)
C21 0.0500(17) 0.0307(13) 0.103(3) -0.0135(15) 0.0417(18) 0.0015(12)
C22 0.0231(11) 0.0444(14) 0.0439(14) 0.0023(11) 0.0156(10) -0.0069(10)
C23 0.0425(16) 0.074(2) 0.062(2) -0.0182(16) 0.0192(15) -0.0304(15)
C24 0.0214(10) 0.0253(10) 0.0225(10) 0.0016(8) 0.0097(8) 0.0037(8)
C25 0.0301(12) 0.0496(15) 0.0243(11) 0.0009(10) -0.0017(10) -0.0027(11)
C26 0.0193(10) 0.0439(13) 0.0275(11) -0.0068(10) 0.0030(9) -0.0066(9)
C27 0.0342(13) 0.0484(15) 0.0288(12) 0.0004(10) 0.0044(10) 0.0068(11)
C28 0.078(2) 0.0557(19) 0.067(2) 0.0065(16) 0.0405(19) 0.0126(17)
_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
Cl1 C28 1.762(4) . ?
Cl2 C28 1.740(4) . ?
S1 C21 1.687(3) . ?
S1 C18 1.708(2) . ?
O1 N1 1.221(4) . ?
O2 N1 1.204(4) . ?
O3 C3 1.206(3) . ?
O4 C4 1.214(3) . ?
O5 C24 1.328(3) . ?
O5 C25 1.451(3) . ?
O6 C24 1.206(3) . ?
O7 C8 1.210(3) . ?
O8 C9 1.208(3) . ?
N1 C15 1.475(3) . ?
N2 C4 1.372(3) . ?
N2 C3 1.387(3) . ?
N2 C26 1.464(3) . ?
N3 C6 1.460(2) . ?
N3 C11 1.470(2) . ?
N3 C1 1.485(3) . ?
N4 C8 1.375(3) . ?
N4 C9 1.382(3) . ?
N4 C22 1.469(3) . ?
C1 C18 1.501(3) . ?
C1 C2 1.572(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.512(3) . ?
C2 C5 1.535(3) . ?
C2 H2 0.9800 . ?
C4 C5 1.518(3) . ?
C5 C6 1.557(3) . ?
C5 H5 0.9800 . ?
C6 C24 1.542(3) . ?
C6 C7 1.544(3) . ?
C7 C8 1.513(3) . ?
C7 C10 1.538(3) . ?
C7 H7 0.9800 . ?
C9 C10 1.524(3) . ?
C10 C11 1.564(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.514(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.390(3) . ?
C12 C17 1.392(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(4) . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.439(3) . ?
C19 C20 1.433(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.345(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.499(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.505(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
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
C21 S1 C18 92.62(14) . . ?
C24 O5 C25 115.71(17) . . ?
O2 N1 O1 122.8(3) . . ?
O2 N1 C15 118.8(3) . . ?
O1 N1 C15 118.4(3) . . ?
C4 N2 C3 113.10(17) . . ?
C4 N2 C26 123.27(18) . . ?
C3 N2 C26 123.36(18) . . ?
C6 N3 C11 110.80(15) . . ?
C6 N3 C1 105.36(15) . . ?
C11 N3 C1 119.12(15) . . ?
C8 N4 C9 113.28(17) . . ?
C8 N4 C22 122.65(19) . . ?
C9 N4 C22 123.87(19) . . ?
N3 C1 C18 113.92(17) . . ?
N3 C1 C2 106.53(16) . . ?
C18 C1 C2 118.98(17) . . ?
N3 C1 H1 105.4 . . ?
C18 C1 H1 105.4 . . ?
C2 C1 H1 105.4 . . ?
C3 C2 C5 104.61(16) . . ?
C3 C2 C1 117.28(17) . . ?
C5 C2 C1 104.50(16) . . ?
C3 C2 H2 110.0 . . ?
C5 C2 H2 110.0 . . ?
C1 C2 H2 110.0 . . ?
O3 C3 N2 123.9(2) . . ?
O3 C3 C2 127.9(2) . . ?
N2 C3 C2 108.16(17) . . ?
O4 C4 N2 123.96(19) . . ?
O4 C4 C5 127.23(19) . . ?
N2 C4 C5 108.78(17) . . ?
C4 C5 C2 104.32(16) . . ?
C4 C5 C6 114.87(16) . . ?
C2 C5 C6 105.21(15) . . ?
C4 C5 H5 110.7 . . ?
C2 C5 H5 110.7 . . ?
C6 C5 H5 110.7 . . ?
N3 C6 C24 109.50(16) . . ?
N3 C6 C7 105.49(15) . . ?
C24 C6 C7 112.46(16) . . ?
N3 C6 C5 106.03(15) . . ?
C24 C6 C5 108.34(16) . . ?
C7 C6 C5 114.72(16) . . ?
C8 C7 C10 105.00(16) . . ?
C8 C7 C6 115.74(16) . . ?
C10 C7 C6 105.56(15) . . ?
C8 C7 H7 110.1 . . ?
C10 C7 H7 110.1 . . ?
C6 C7 H7 110.1 . . ?
O7 C8 N4 125.0(2) . . ?
O7 C8 C7 126.1(2) . . ?
N4 C8 C7 108.81(17) . . ?
O8 C9 N4 124.2(2) . . ?
O8 C9 C10 127.2(2) . . ?
N4 C9 C10 108.54(17) . . ?
C9 C10 C7 104.11(16) . . ?
C9 C10 C11 115.71(16) . . ?
C7 C10 C11 107.04(15) . . ?
C9 C10 H10 109.9 . . ?
C7 C10 H10 109.9 . . ?
C11 C10 H10 109.9 . . ?
N3 C11 C12 110.96(16) . . ?
N3 C11 C10 103.99(15) . . ?
C12 C11 C10 113.72(16) . . ?
N3 C11 H11 109.3 . . ?
C12 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
C13 C12 C17 119.3(2) . . ?
C13 C12 C11 120.33(19) . . ?
C17 C12 C11 120.28(18) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 118.0(2) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C16 122.8(2) . . ?
C14 C15 N1 118.5(2) . . ?
C16 C15 N1 118.6(3) . . ?
C15 C16 C17 118.3(2) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C12 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C19 C18 C1 131.06(19) . . ?
C19 C18 S1 111.52(16) . . ?
C1 C18 S1 117.14(16) . . ?
C20 C19 C18 108.5(2) . . ?
C20 C19 H19 125.8 . . ?
C18 C19 H19 125.8 . . ?
C21 C20 C19 114.7(3) . . ?
C21 C20 H20 122.7 . . ?
C19 C20 H20 122.7 . . ?
C20 C21 S1 112.7(2) . . ?
C20 C21 H21 123.7 . . ?
S1 C21 H21 123.7 . . ?
N4 C22 C23 111.4(2) . . ?
N4 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
N4 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 O5 124.47(19) . . ?
O6 C24 C6 124.56(19) . . ?
O5 C24 C6 110.97(16) . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 C27 111.40(19) . . ?
N2 C26 H26A 109.3 . . ?
C27 C26 H26A 109.3 . . ?
N2 C26 H26B 109.3 . . ?
C27 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Cl2 C28 Cl1 112.4(2) . . ?
Cl2 C28 H28A 109.1 . . ?
Cl1 C28 H28A 109.1 . . ?
Cl2 C28 H28B 109.1 . . ?
Cl1 C28 H28B 109.1 . . ?
H28A C28 H28B 107.9 . . ?
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
C6 N3 C1 C18 165.23(16) . . . . ?
C11 N3 C1 C18 40.2(2) . . . . ?
C6 N3 C1 C2 32.03(19) . . . . ?
C11 N3 C1 C2 -93.04(19) . . . . ?
N3 C1 C2 C3 99.9(2) . . . . ?
C18 C1 C2 C3 -30.5(3) . . . . ?
N3 C1 C2 C5 -15.3(2) . . . . ?
C18 C1 C2 C5 -145.70(18) . . . . ?
C4 N2 C3 O3 170.6(2) . . . . ?
C26 N2 C3 O3 -3.6(3) . . . . ?
C4 N2 C3 C2 -8.4(2) . . . . ?
C26 N2 C3 C2 177.37(18) . . . . ?
C5 C2 C3 O3 -168.6(2) . . . . ?
C1 C2 C3 O3 76.3(3) . . . . ?
C5 C2 C3 N2 10.4(2) . . . . ?
C1 C2 C3 N2 -104.8(2) . . . . ?
C3 N2 C4 O4 -175.5(2) . . . . ?
C26 N2 C4 O4 -1.3(3) . . . . ?
C3 N2 C4 C5 2.6(2) . . . . ?
C26 N2 C4 C5 176.85(18) . . . . ?
O4 C4 C5 C2 -177.8(2) . . . . ?
N2 C4 C5 C2 4.1(2) . . . . ?
O4 C4 C5 C6 -63.2(3) . . . . ?
N2 C4 C5 C6 118.71(19) . . . . ?
C3 C2 C5 C4 -8.5(2) . . . . ?
C1 C2 C5 C4 115.30(17) . . . . ?
C3 C2 C5 C6 -129.79(16) . . . . ?
C1 C2 C5 C6 -5.97(19) . . . . ?
C11 N3 C6 C24 -149.14(16) . . . . ?
C1 N3 C6 C24 80.76(18) . . . . ?
C11 N3 C6 C7 -27.90(19) . . . . ?
C1 N3 C6 C7 -158.00(15) . . . . ?
C11 N3 C6 C5 94.18(18) . . . . ?
C1 N3 C6 C5 -35.93(19) . . . . ?
C4 C5 C6 N3 -88.3(2) . . . . ?
C2 C5 C6 N3 25.8(2) . . . . ?
C4 C5 C6 C24 154.23(17) . . . . ?
C2 C5 C6 C24 -91.66(18) . . . . ?
C4 C5 C6 C7 27.7(2) . . . . ?
C2 C5 C6 C7 141.78(16) . . . . ?
N3 C6 C7 C8 -97.42(19) . . . . ?
C24 C6 C7 C8 21.9(2) . . . . ?
C5 C6 C7 C8 146.28(17) . . . . ?
N3 C6 C7 C10 18.20(19) . . . . ?
C24 C6 C7 C10 137.50(16) . . . . ?
C5 C6 C7 C10 -98.09(18) . . . . ?
C9 N4 C8 O7 -174.4(2) . . . . ?
C22 N4 C8 O7 0.5(3) . . . . ?
C9 N4 C8 C7 2.6(2) . . . . ?
C22 N4 C8 C7 177.56(19) . . . . ?
C10 C7 C8 O7 177.9(2) . . . . ?
C6 C7 C8 O7 -66.2(3) . . . . ?
C10 C7 C8 N4 0.9(2) . . . . ?
C6 C7 C8 N4 116.84(19) . . . . ?
C8 N4 C9 O8 173.1(2) . . . . ?
C22 N4 C9 O8 -1.8(4) . . . . ?
C8 N4 C9 C10 -5.0(2) . . . . ?
C22 N4 C9 C10 -179.93(19) . . . . ?
O8 C9 C10 C7 -172.9(2) . . . . ?
N4 C9 C10 C7 5.2(2) . . . . ?
O8 C9 C10 C11 70.0(3) . . . . ?
N4 C9 C10 C11 -111.96(19) . . . . ?
C8 C7 C10 C9 -3.6(2) . . . . ?
C6 C7 C10 C9 -126.35(16) . . . . ?
C8 C7 C10 C11 119.44(17) . . . . ?
C6 C7 C10 C11 -3.3(2) . . . . ?
C6 N3 C11 C12 147.96(16) . . . . ?
C1 N3 C11 C12 -89.6(2) . . . . ?
C6 N3 C11 C10 25.3(2) . . . . ?
C1 N3 C11 C10 147.73(16) . . . . ?
C9 C10 C11 N3 102.98(19) . . . . ?
C7 C10 C11 N3 -12.5(2) . . . . ?
C9 C10 C11 C12 -17.8(2) . . . . ?
C7 C10 C11 C12 -133.33(17) . . . . ?
N3 C11 C12 C13 146.99(19) . . . . ?
C10 C11 C12 C13 -96.2(2) . . . . ?
N3 C11 C12 C17 -36.7(3) . . . . ?
C10 C11 C12 C17 80.1(2) . . . . ?
C17 C12 C13 C14 -2.9(3) . . . . ?
C11 C12 C13 C14 173.5(2) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C13 C14 C15 C16 2.7(4) . . . . ?
C13 C14 C15 N1 -176.0(2) . . . . ?
O2 N1 C15 C14 -170.7(3) . . . . ?
O1 N1 C15 C14 9.2(4) . . . . ?
O2 N1 C15 C16 10.5(4) . . . . ?
O1 N1 C15 C16 -169.6(3) . . . . ?
C14 C15 C16 C17 -2.7(4) . . . . ?
N1 C15 C16 C17 176.0(2) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
C13 C12 C17 C16 2.9(3) . . . . ?
C11 C12 C17 C16 -173.5(2) . . . . ?
N3 C1 C18 C19 -75.8(3) . . . . ?
C2 C1 C18 C19 51.2(3) . . . . ?
N3 C1 C18 S1 97.63(19) . . . . ?
C2 C1 C18 S1 -135.40(17) . . . . ?
C21 S1 C18 C19 1.08(19) . . . . ?
C21 S1 C18 C1 -173.58(19) . . . . ?
C1 C18 C19 C20 172.7(2) . . . . ?
S1 C18 C19 C20 -1.0(2) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C19 C20 C21 S1 0.5(3) . . . . ?
C18 S1 C21 C20 -0.9(3) . . . . ?
C8 N4 C22 C23 83.4(3) . . . . ?
C9 N4 C22 C23 -102.2(3) . . . . ?
C25 O5 C24 O6 -7.2(3) . . . . ?
C25 O5 C24 C6 172.30(18) . . . . ?
N3 C6 C24 O6 -137.5(2) . . . . ?
C7 C6 C24 O6 105.6(2) . . . . ?
C5 C6 C24 O6 -22.3(3) . . . . ?
N3 C6 C24 O5 43.0(2) . . . . ?
C7 C6 C24 O5 -73.9(2) . . . . ?
C5 C6 C24 O5 158.23(17) . . . . ?
C4 N2 C26 C27 99.5(3) . . . . ?
C3 N2 C26 C27 -86.9(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
C1 H1 O4 0.98 2.44 3.160(3) 129.5 4_565
C2 H2 O4 0.98 2.41 3.155(3) 132.5 4_565
C5 H5 O1 0.98 2.44 3.179(3) 132.2 2_655
C14 H14 O8 0.93 2.51 3.417(3) 165.9 3_656
C22 H22A O3 0.97 2.57 3.456(3) 151.7 1_455
C26 H26B O7 0.97 2.43 3.147(3) 130.2 4_666
C28 H28A O8 0.97 2.45 3.395(4) 166.3 4_565
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full 67.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.666
_refine_diff_density_min -0.522
_refine_diff_density_rms 0.061