# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_coden_Cambridge 182
_journal_volume ?
_journal_page_first ?
_journal_year ?
loop_
_publ_author_name
'McLaughlin, Larry'
'Theile, Christopher'
_publ_contact_author_name 'Prof. Larry McLaughlin'
_publ_contact_author_email larry.mclaughlin@bc.edu
_publ_section_title
;
An Efficient Synthetic Approach to
6,5' (S) and 6,5' (R) - Cyclouridine
;
# Attachment '- Compound 9.cif'
data_C12H14N2O6
_database_code_depnum_ccdc_archive 'CCDC 870187'
#TrackingRef '- Compound 9.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_melting_point 'not measured'
_chemical_formula_moiety 'C12 H14 N2 O6'
_chemical_formula_sum 'C12 H14 N2 O6'
_chemical_formula_weight 282.25
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 C2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a 11.1949(18)
_cell_length_b 6.3676(10)
_cell_length_c 18.385(3)
_cell_angle_alpha 90.00
_cell_angle_beta 105.512(2)
_cell_angle_gamma 90.00
_cell_volume 1262.9(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 5150
_cell_measurement_theta_min 2.30
_cell_measurement_theta_max 28.19
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.13
_exptl_crystal_size_mid 0.07
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.485
_exptl_crystal_density_method none
_exptl_crystal_F_000 592
_exptl_absorpt_coefficient_mu 0.121
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9845
_exptl_absorpt_correction_T_max 0.9976
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'normal-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEX CCD'
_diffrn_measurement_method '0.3 deg wide \w exposures'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 7524
_diffrn_reflns_av_R_equivalents 0.0274
_diffrn_reflns_av_sigmaI/netI 0.0378
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 2.30
_diffrn_reflns_theta_max 28.25
_reflns_number_total 3037
_reflns_number_gt 2831
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.1903P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refxyz
_refine_ls_extinction_method none
_refine_ls_extinction_coef na
_chemical_absolute_configuration syn
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.8(8)
_refine_ls_number_reflns 3037
_refine_ls_number_parameters 223
_refine_ls_number_restraints 214
_refine_ls_R_factor_all 0.0421
_refine_ls_R_factor_gt 0.0390
_refine_ls_wR_factor_ref 0.0972
_refine_ls_wR_factor_gt 0.0952
_refine_ls_goodness_of_fit_ref 1.057
_refine_ls_restrained_S_all 1.022
_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 0.55911(9) 0.86075(19) 0.59533(6) 0.0179(2) Uani 1 1 d U . .
O2 O 0.78726(10) 0.8808(2) 0.42522(6) 0.0193(3) Uani 1 1 d U . .
O3 O 1.09167(10) 0.8133(2) 0.69223(6) 0.0183(2) Uani 1 1 d DU . .
H3O H 1.1126(18) 0.835(3) 0.6507(9) 0.022 Uiso 1 1 d D . .
O4 O 0.85000(9) 1.05789(18) 0.75838(6) 0.0168(2) Uani 1 1 d U . .
O5 O 0.94672(10) 0.7232(2) 0.87120(6) 0.0212(3) Uani 1 1 d U . .
O6 O 0.73979(10) 0.6985(2) 0.81958(6) 0.0204(3) Uani 1 1 d U . .
N1 N 0.67521(11) 0.8789(2) 0.51116(7) 0.0146(3) Uani 1 1 d DU . .
H1N H 0.6037(15) 0.866(3) 0.4751(9) 0.017 Uiso 1 1 d D . .
N2 N 0.76718(11) 0.9063(2) 0.63992(7) 0.0131(3) Uani 1 1 d U . .
C1 C 0.66077(13) 0.8806(2) 0.58269(8) 0.0134(3) Uani 1 1 d U . .
C2 C 0.78729(13) 0.8854(2) 0.49209(8) 0.0147(3) Uani 1 1 d U . .
C3 C 0.89384(14) 0.8995(3) 0.55570(9) 0.0187(3) Uani 1 1 d DU . .
H3 H 0.9739(14) 0.907(4) 0.5486(10) 0.022 Uiso 1 1 d D . .
C4 C 0.88170(13) 0.9152(3) 0.62609(9) 0.0144(3) Uani 1 1 d U . .
C5 C 0.99470(13) 0.9537(3) 0.69260(8) 0.0146(3) Uani 1 1 d DU . .
H5 H 1.0146(18) 1.101(2) 0.6862(10) 0.017 Uiso 1 1 d D . .
C6 C 0.96394(13) 0.9416(3) 0.76847(9) 0.0151(3) Uani 1 1 d DU . .
H6 H 1.0299(15) 1.005(3) 0.8087(9) 0.018 Uiso 1 1 d D . .
C7 C 0.93249(13) 0.7229(3) 0.79195(8) 0.0161(3) Uani 1 1 d DU . .
H7 H 0.9800(16) 0.613(3) 0.7765(11) 0.019 Uiso 1 1 d D . .
C8 C 0.79059(13) 0.7064(3) 0.75719(8) 0.0160(3) Uani 1 1 d DU . .
H8 H 0.7651(17) 0.591(3) 0.7218(10) 0.019 Uiso 1 1 d D . .
C9 C 0.75835(13) 0.9187(3) 0.71866(8) 0.0150(3) Uani 1 1 d DU . .
H9 H 0.6766(14) 0.967(3) 0.7171(11) 0.018 Uiso 1 1 d D . .
C10 C 0.83602(14) 0.6419(3) 0.88495(9) 0.0181(3) Uani 1 1 d U . .
C11 C 0.84296(19) 0.4056(3) 0.89353(11) 0.0287(4) Uani 1 1 d DU . .
H11A H 0.7655(17) 0.350(4) 0.9005(14) 0.043 Uiso 1 1 d D . .
H11B H 0.855(2) 0.338(4) 0.8491(11) 0.043 Uiso 1 1 d D . .
H11C H 0.9096(19) 0.371(4) 0.9380(11) 0.043 Uiso 1 1 d D . .
C12 C 0.81272(18) 0.7546(3) 0.95162(10) 0.0258(4) Uani 1 1 d DU . .
H12A H 0.810(2) 0.907(3) 0.9427(13) 0.039 Uiso 1 1 d D . .
H12B H 0.7341(16) 0.710(4) 0.9609(12) 0.039 Uiso 1 1 d D . .
H12C H 0.8749(18) 0.721(4) 0.9982(10) 0.039 Uiso 1 1 d D . .
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 0.0110(5) 0.0272(6) 0.0154(5) 0.0009(5) 0.0035(4) -0.0010(4)
O2 0.0163(5) 0.0277(6) 0.0148(5) -0.0007(5) 0.0053(4) -0.0015(5)
O3 0.0122(5) 0.0240(6) 0.0191(5) 0.0005(5) 0.0048(4) 0.0027(4)
O4 0.0136(5) 0.0193(6) 0.0169(5) -0.0050(5) 0.0033(4) -0.0017(4)
O5 0.0153(5) 0.0333(7) 0.0146(5) 0.0024(5) 0.0036(4) -0.0030(5)
O6 0.0153(5) 0.0320(7) 0.0148(5) 0.0036(5) 0.0058(4) -0.0031(5)
N1 0.0110(6) 0.0177(6) 0.0143(6) 0.0011(5) 0.0022(5) -0.0006(5)
N2 0.0108(5) 0.0162(6) 0.0128(6) 0.0016(5) 0.0037(4) 0.0005(5)
C1 0.0125(6) 0.0134(7) 0.0143(7) 0.0012(6) 0.0038(5) 0.0008(5)
C2 0.0133(7) 0.0147(7) 0.0175(7) 0.0000(6) 0.0064(6) -0.0001(6)
C3 0.0119(6) 0.0267(8) 0.0186(7) 0.0003(7) 0.0058(6) -0.0028(6)
C4 0.0103(6) 0.0164(7) 0.0161(7) 0.0010(6) 0.0028(5) -0.0011(5)
C5 0.0098(6) 0.0191(7) 0.0147(7) -0.0001(6) 0.0031(5) -0.0021(5)
C6 0.0104(6) 0.0206(8) 0.0134(7) -0.0021(6) 0.0016(5) -0.0032(6)
C7 0.0138(6) 0.0208(7) 0.0136(7) 0.0014(6) 0.0035(5) -0.0006(6)
C8 0.0136(7) 0.0201(7) 0.0149(7) 0.0000(6) 0.0050(5) -0.0036(6)
C9 0.0120(6) 0.0210(8) 0.0120(6) -0.0012(6) 0.0033(5) -0.0022(6)
C10 0.0166(7) 0.0235(8) 0.0147(7) 0.0023(6) 0.0050(6) -0.0015(6)
C11 0.0403(10) 0.0223(9) 0.0247(9) 0.0027(8) 0.0106(8) 0.0003(8)
C12 0.0291(9) 0.0319(10) 0.0184(8) -0.0011(7) 0.0099(7) 0.0013(7)
_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 1.2275(18) . ?
O2 C2 1.2297(18) . ?
O3 C5 1.4081(18) . ?
O3 H3O 0.867(14) . ?
O4 C9 1.4040(19) . ?
O4 C6 1.4433(18) . ?
O5 C7 1.4226(18) . ?
O5 C10 1.4266(19) . ?
O6 C8 1.4109(18) . ?
O6 C10 1.4291(19) . ?
N1 C1 1.3673(18) . ?
N1 C2 1.3907(18) . ?
N1 H1N 0.896(15) . ?
N2 C1 1.3721(18) . ?
N2 C4 1.3733(18) . ?
N2 C9 1.4793(18) . ?
C2 C3 1.433(2) . ?
C3 C4 1.341(2) . ?
C3 H3 0.941(14) . ?
C4 C5 1.526(2) . ?
C5 C6 1.525(2) . ?
C5 H5 0.980(15) . ?
C6 C7 1.527(2) . ?
C6 H6 0.982(14) . ?
C7 C8 1.549(2) . ?
C7 H7 0.968(15) . ?
C8 C9 1.524(2) . ?
C8 H8 0.972(15) . ?
C9 H9 0.959(14) . ?
C10 C12 1.502(2) . ?
C10 C11 1.513(3) . ?
C11 H11A 0.976(16) . ?
C11 H11B 0.965(16) . ?
C11 H11C 0.974(16) . ?
C12 H12A 0.983(17) . ?
C12 H12B 0.982(15) . ?
C12 H12C 0.973(16) . ?
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
C5 O3 H3O 107.1(14) . . ?
C9 O4 C6 103.93(12) . . ?
C7 O5 C10 108.45(11) . . ?
C8 O6 C10 108.39(11) . . ?
C1 N1 C2 126.08(13) . . ?
C1 N1 H1N 113.5(12) . . ?
C2 N1 H1N 120.3(12) . . ?
C1 N2 C4 121.67(12) . . ?
C1 N2 C9 119.03(12) . . ?
C4 N2 C9 119.27(12) . . ?
O1 C1 N1 122.38(13) . . ?
O1 C1 N2 121.72(13) . . ?
N1 C1 N2 115.90(12) . . ?
O2 C2 N1 119.48(13) . . ?
O2 C2 C3 126.53(13) . . ?
N1 C2 C3 113.98(13) . . ?
C4 C3 C2 121.03(14) . . ?
C4 C3 H3 118.5(11) . . ?
C2 C3 H3 120.4(11) . . ?
C3 C4 N2 121.08(13) . . ?
C3 C4 C5 120.61(13) . . ?
N2 C4 C5 118.25(13) . . ?
O3 C5 C6 109.58(12) . . ?
O3 C5 C4 111.66(13) . . ?
C6 C5 C4 112.53(12) . . ?
O3 C5 H5 114.1(12) . . ?
C6 C5 H5 105.8(11) . . ?
C4 C5 H5 103.0(11) . . ?
O4 C6 C5 105.33(12) . . ?
O4 C6 C7 103.97(11) . . ?
C5 C6 C7 115.49(13) . . ?
O4 C6 H6 110.3(12) . . ?
C5 C6 H6 111.1(11) . . ?
C7 C6 H6 110.2(12) . . ?
O5 C7 C6 108.51(13) . . ?
O5 C7 C8 104.13(11) . . ?
C6 C7 C8 103.53(13) . . ?
O5 C7 H7 112.4(12) . . ?
C6 C7 H7 113.1(12) . . ?
C8 C7 H7 114.4(12) . . ?
O6 C8 C9 108.21(13) . . ?
O6 C8 C7 105.00(12) . . ?
C9 C8 C7 102.74(12) . . ?
O6 C8 H8 114.1(12) . . ?
C9 C8 H8 111.6(12) . . ?
C7 C8 H8 114.4(12) . . ?
O4 C9 N2 108.16(12) . . ?
O4 C9 C8 105.61(12) . . ?
N2 C9 C8 109.77(13) . . ?
O4 C9 H9 111.8(13) . . ?
N2 C9 H9 107.5(11) . . ?
C8 C9 H9 113.8(13) . . ?
O5 C10 O6 104.76(12) . . ?
O5 C10 C12 108.66(14) . . ?
O6 C10 C12 108.02(14) . . ?
O5 C10 C11 110.89(15) . . ?
O6 C10 C11 110.16(14) . . ?
C12 C10 C11 113.91(15) . . ?
C10 C11 H11A 110.6(16) . . ?
C10 C11 H11B 111.7(16) . . ?
H11A C11 H11B 106(2) . . ?
C10 C11 H11C 108.7(17) . . ?
H11A C11 H11C 108(2) . . ?
H11B C11 H11C 111(2) . . ?
C10 C12 H12A 109.9(13) . . ?
C10 C12 H12B 111.4(15) . . ?
H12A C12 H12B 109(2) . . ?
C10 C12 H12C 112.0(15) . . ?
H12A C12 H12C 110(2) . . ?
H12B C12 H12C 104.3(19) . . ?
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
C2 N1 C1 O1 -175.17(15) . . . . ?
C2 N1 C1 N2 5.0(2) . . . . ?
C4 N2 C1 O1 175.84(15) . . . . ?
C9 N2 C1 O1 -2.4(2) . . . . ?
C4 N2 C1 N1 -4.3(2) . . . . ?
C9 N2 C1 N1 177.47(13) . . . . ?
C1 N1 C2 O2 179.24(15) . . . . ?
C1 N1 C2 C3 -1.4(2) . . . . ?
O2 C2 C3 C4 176.21(16) . . . . ?
N1 C2 C3 C4 -3.1(2) . . . . ?
C2 C3 C4 N2 3.8(3) . . . . ?
C2 C3 C4 C5 -173.40(15) . . . . ?
C1 N2 C4 C3 0.2(2) . . . . ?
C9 N2 C4 C3 178.38(15) . . . . ?
C1 N2 C4 C5 177.38(14) . . . . ?
C9 N2 C4 C5 -4.4(2) . . . . ?
C3 C4 C5 O3 -49.7(2) . . . . ?
N2 C4 C5 O3 133.06(15) . . . . ?
C3 C4 C5 C6 -173.41(16) . . . . ?
N2 C4 C5 C6 9.3(2) . . . . ?
C9 O4 C6 C5 77.98(14) . . . . ?
C9 O4 C6 C7 -43.90(14) . . . . ?
O3 C5 C6 O4 -169.24(12) . . . . ?
C4 C5 C6 O4 -44.38(16) . . . . ?
O3 C5 C6 C7 -55.16(16) . . . . ?
C4 C5 C6 C7 69.71(17) . . . . ?
C10 O5 C7 C6 128.30(13) . . . . ?
C10 O5 C7 C8 18.50(16) . . . . ?
O4 C6 C7 O5 -84.23(14) . . . . ?
C5 C6 C7 O5 160.91(12) . . . . ?
O4 C6 C7 C8 25.98(14) . . . . ?
C5 C6 C7 C8 -88.88(14) . . . . ?
C10 O6 C8 C9 -127.40(13) . . . . ?
C10 O6 C8 C7 -18.22(16) . . . . ?
O5 C7 C8 O6 -0.15(16) . . . . ?
C6 C7 C8 O6 -113.56(13) . . . . ?
O5 C7 C8 C9 112.95(13) . . . . ?
C6 C7 C8 C9 -0.46(14) . . . . ?
C6 O4 C9 N2 -73.33(14) . . . . ?
C6 O4 C9 C8 44.15(14) . . . . ?
C1 N2 C9 O4 -145.77(13) . . . . ?
C4 N2 C9 O4 35.96(19) . . . . ?
C1 N2 C9 C8 99.47(15) . . . . ?
C4 N2 C9 C8 -78.80(17) . . . . ?
O6 C8 C9 O4 84.53(14) . . . . ?
C7 C8 C9 O4 -26.18(14) . . . . ?
O6 C8 C9 N2 -159.08(11) . . . . ?
C7 C8 C9 N2 90.20(13) . . . . ?
C7 O5 C10 O6 -30.02(17) . . . . ?
C7 O5 C10 C12 -145.27(14) . . . . ?
C7 O5 C10 C11 88.80(16) . . . . ?
C8 O6 C10 O5 29.90(17) . . . . ?
C8 O6 C10 C12 145.61(14) . . . . ?
C8 O6 C10 C11 -89.40(16) . . . . ?
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
O3 H3O O2 0.867(14) 2.032(15) 2.8724(16) 163.0(19) 2_756
N1 H1N O1 0.896(15) 1.933(15) 2.8250(17) 173.0(19) 2_656
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 28.25
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max 0.379
_refine_diff_density_min -0.192
_refine_diff_density_rms 0.054
# Attachment '- compound 11R.cif'
data_(C13H14N2O8)(H2O)
_database_code_depnum_ccdc_archive 'CCDC 870188'
#TrackingRef '- compound 11R.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety '(C13 H14 N2 O8) (H2 O)'
_chemical_formula_sum 'C13 H16 N2 O9'
_chemical_formula_weight 344.28
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'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 9.549(7)
_cell_length_b 7.829(5)
_cell_length_c 10.026(7)
_cell_angle_alpha 90.00
_cell_angle_beta 108.140(7)
_cell_angle_gamma 90.00
_cell_volume 712.3(8)
_cell_formula_units_Z 2
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 2062
_cell_measurement_theta_min 2.57
_cell_measurement_theta_max 27.85
_exptl_crystal_description needle
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.04
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.605
_exptl_crystal_density_method none
_exptl_crystal_F_000 360
_exptl_absorpt_coefficient_mu 0.138
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9598
_exptl_absorpt_correction_T_max 0.9959
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'normal-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEX CCD'
_diffrn_measurement_method '0.3 deg wide \w exposures'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 6194
_diffrn_reflns_av_R_equivalents 0.0666
_diffrn_reflns_av_sigmaI/netI 0.1115
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.57
_diffrn_reflns_theta_max 27.00
_reflns_number_total 3059
_reflns_number_gt 2060
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refxyz
_refine_ls_extinction_method none
_refine_ls_extinction_coef na
_chemical_absolute_configuration syn
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -2.2(16)
_refine_ls_number_reflns 3059
_refine_ls_number_parameters 265
_refine_ls_number_restraints 32
_refine_ls_R_factor_all 0.0998
_refine_ls_R_factor_gt 0.0577
_refine_ls_wR_factor_ref 0.1178
_refine_ls_wR_factor_gt 0.1040
_refine_ls_goodness_of_fit_ref 1.000
_refine_ls_restrained_S_all 0.996
_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
O1 O 0.3531(3) 0.6709(3) 0.5090(3) 0.0219(6) Uani 1 1 d . . .
O1S O -0.3909(3) 1.3067(4) -0.0515(3) 0.0337(7) Uani 1 1 d D . .
H1SA H -0.388(5) 1.203(3) -0.030(4) 0.040 Uiso 1 1 d D . .
H1SB H -0.460(4) 1.363(6) -0.036(4) 0.040 Uiso 1 1 d D . .
O2 O 0.2833(3) 0.6773(4) 0.7026(3) 0.0375(7) Uani 1 1 d . . .
O3 O 0.2710(2) 0.3620(3) 0.5067(3) 0.0230(6) Uani 1 1 d . . .
O4 O 0.1164(3) 0.1684(4) 0.5431(3) 0.0378(7) Uani 1 1 d . . .
O5 O 0.1920(3) 0.5145(3) 0.2191(3) 0.0227(6) Uani 1 1 d . . .
O6 O -0.1019(3) 0.3561(3) 0.0734(3) 0.0235(6) Uani 1 1 d D . .
H6O H -0.198(2) 0.360(6) 0.032(4) 0.028 Uiso 1 1 d D . .
O7 O -0.3551(3) 0.9596(3) 0.0168(3) 0.0270(7) Uani 1 1 d . . .
O8 O 0.1352(3) 1.0121(3) 0.2357(3) 0.0301(7) Uani 1 1 d . . .
N1 N 0.0380(3) 0.7477(4) 0.2049(3) 0.0198(8) Uani 1 1 d . . .
N2 N -0.1097(4) 0.9830(4) 0.1208(4) 0.0223(7) Uani 1 1 d D . .
H2N H -0.112(4) 1.094(2) 0.117(4) 0.027 Uiso 1 1 d D . .
C1 C 0.1849(4) 0.6765(5) 0.2756(4) 0.0220(8) Uani 1 1 d D . .
H1 H 0.256(3) 0.760(4) 0.257(4) 0.026 Uiso 1 1 d D . .
C2 C 0.1999(4) 0.6506(5) 0.4290(4) 0.0195(8) Uani 1 1 d D . .
H2 H 0.139(3) 0.735(4) 0.458(4) 0.023 Uiso 1 1 d D . .
C3 C 0.1476(4) 0.4641(5) 0.4310(4) 0.0199(8) Uani 1 1 d D . .
H3 H 0.069(3) 0.451(5) 0.476(3) 0.024 Uiso 1 1 d D . .
C4 C 0.0993(4) 0.4143(4) 0.2774(4) 0.0200(9) Uani 1 1 d D . .
H4 H 0.118(4) 0.293(3) 0.268(4) 0.024 Uiso 1 1 d D . .
C5 C -0.0606(4) 0.4558(5) 0.1982(4) 0.0212(9) Uani 1 1 d D . .
H5 H -0.117(3) 0.420(4) 0.262(3) 0.025 Uiso 1 1 d D . .
C6 C -0.0842(4) 0.6438(5) 0.1625(4) 0.0188(8) Uani 1 1 d . . .
C7 C -0.2166(4) 0.7105(5) 0.0965(4) 0.0234(9) Uani 1 1 d D . .
H7 H -0.305(3) 0.642(4) 0.061(4) 0.028 Uiso 1 1 d D . .
C8 C -0.2366(4) 0.8879(5) 0.0730(4) 0.0227(9) Uani 1 1 d . . .
C9 C 0.0283(4) 0.9225(5) 0.1894(4) 0.0219(9) Uani 1 1 d . . .
C10 C 0.3798(4) 0.6771(5) 0.6482(4) 0.0256(9) Uani 1 1 d . . .
C11 C 0.5396(5) 0.6871(7) 0.7240(4) 0.0346(10) Uani 1 1 d D . .
H11A H 0.585(5) 0.575(3) 0.741(4) 0.052 Uiso 1 1 d D . .
H11B H 0.555(4) 0.742(4) 0.816(3) 0.052 Uiso 1 1 d D . .
H11C H 0.590(4) 0.756(4) 0.672(3) 0.052 Uiso 1 1 d D . .
C12 C 0.2396(4) 0.2146(5) 0.5585(4) 0.0253(9) Uani 1 1 d . . .
C13 C 0.3753(5) 0.1202(6) 0.6333(5) 0.0343(11) Uani 1 1 d D . .
H13A H 0.452(4) 0.201(4) 0.683(3) 0.051 Uiso 1 1 d D . .
H13B H 0.365(5) 0.033(4) 0.699(3) 0.051 Uiso 1 1 d D . .
H13C H 0.405(4) 0.066(4) 0.559(3) 0.051 Uiso 1 1 d D . .
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 0.0200(13) 0.0183(14) 0.0265(14) -0.0022(13) 0.0059(11) -0.0011(13)
O1S 0.0267(17) 0.0180(17) 0.055(2) 0.0023(15) 0.0110(15) 0.0021(14)
O2 0.0366(16) 0.043(2) 0.0375(17) 0.0015(16) 0.0189(14) -0.0014(16)
O3 0.0180(14) 0.0114(14) 0.0401(16) 0.0052(12) 0.0097(12) -0.0005(12)
O4 0.0277(16) 0.0273(16) 0.0580(19) 0.0117(16) 0.0126(14) -0.0055(15)
O5 0.0277(15) 0.0131(14) 0.0303(15) 0.0000(11) 0.0133(12) 0.0008(12)
O6 0.0210(14) 0.0135(14) 0.0344(15) -0.0040(13) 0.0063(12) -0.0010(13)
O7 0.0223(15) 0.0181(16) 0.0377(16) -0.0016(13) 0.0052(12) 0.0026(13)
O8 0.0260(17) 0.0133(15) 0.0476(18) -0.0039(13) 0.0067(13) -0.0025(13)
N1 0.0178(18) 0.0152(18) 0.0249(18) 0.0012(14) 0.0044(15) -0.0026(14)
N2 0.0235(18) 0.0075(17) 0.0343(19) 0.0002(14) 0.0068(14) -0.0003(14)
C1 0.0189(19) 0.014(2) 0.033(2) 0.0015(18) 0.0071(17) -0.0004(18)
C2 0.0154(19) 0.010(2) 0.031(2) -0.0018(16) 0.0047(17) -0.0011(16)
C3 0.0183(19) 0.015(2) 0.028(2) 0.0034(17) 0.0100(16) 0.0014(16)
C4 0.026(2) 0.0054(19) 0.031(2) 0.0035(16) 0.0133(19) -0.0006(16)
C5 0.024(2) 0.014(2) 0.024(2) 0.0014(17) 0.0069(17) 0.0004(17)
C6 0.023(2) 0.016(2) 0.0179(19) -0.0032(16) 0.0068(16) -0.0004(17)
C7 0.022(2) 0.015(2) 0.030(2) -0.0010(17) 0.0048(18) -0.0025(17)
C8 0.023(2) 0.022(2) 0.021(2) -0.0045(17) 0.0041(17) -0.0015(18)
C9 0.019(2) 0.015(2) 0.032(2) -0.0045(16) 0.0072(18) -0.0038(17)
C10 0.035(2) 0.0090(19) 0.033(2) 0.0033(19) 0.010(2) -0.0004(19)
C11 0.035(2) 0.038(3) 0.028(2) -0.002(2) 0.005(2) 0.003(2)
C12 0.028(2) 0.023(2) 0.027(2) -0.0032(18) 0.0103(19) -0.0024(19)
C13 0.036(3) 0.023(3) 0.047(3) 0.013(2) 0.017(2) 0.007(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.339(5) . ?
O1 C2 1.441(4) . ?
O1S H1SA 0.842(19) . ?
O1S H1SB 0.844(19) . ?
O2 C10 1.207(4) . ?
O3 C12 1.337(5) . ?
O3 C3 1.430(4) . ?
O4 C12 1.193(4) . ?
O5 C1 1.399(5) . ?
O5 C4 1.437(4) . ?
O6 C5 1.422(5) . ?
O6 H6O 0.883(18) . ?
O7 C8 1.231(5) . ?
O8 C9 1.206(4) . ?
N1 C6 1.377(5) . ?
N1 C9 1.377(5) . ?
N1 C1 1.470(5) . ?
N2 C9 1.367(5) . ?
N2 C8 1.375(5) . ?
N2 H2N 0.869(19) . ?
C1 C2 1.512(5) . ?
C1 H1 1.007(18) . ?
C2 C3 1.545(6) . ?
C2 H2 0.987(18) . ?
C3 C4 1.514(6) . ?
C3 H3 0.996(18) . ?
C4 C5 1.521(6) . ?
C4 H4 0.973(18) . ?
C5 C6 1.515(5) . ?
C5 H5 0.999(18) . ?
C6 C7 1.337(5) . ?
C7 C8 1.411(6) . ?
C7 H7 0.969(19) . ?
C10 C11 1.480(6) . ?
C11 H11A 0.968(18) . ?
C11 H11B 0.985(18) . ?
C11 H11C 0.973(18) . ?
C12 C13 1.478(6) . ?
C13 H13A 0.977(18) . ?
C13 H13B 0.972(18) . ?
C13 H13C 0.976(17) . ?
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
C10 O1 C2 114.5(3) . . ?
H1SA O1S H1SB 115(5) . . ?
C12 O3 C3 116.2(3) . . ?
C1 O5 C4 102.5(3) . . ?
C5 O6 H6O 111(3) . . ?
C6 N1 C9 122.1(3) . . ?
C6 N1 C1 121.0(3) . . ?
C9 N1 C1 116.9(3) . . ?
C9 N2 C8 126.5(3) . . ?
C9 N2 H2N 112(3) . . ?
C8 N2 H2N 121(3) . . ?
O5 C1 N1 107.9(3) . . ?
O5 C1 C2 106.8(3) . . ?
N1 C1 C2 108.4(3) . . ?
O5 C1 H1 113(2) . . ?
N1 C1 H1 105(2) . . ?
C2 C1 H1 115(2) . . ?
O1 C2 C1 108.1(3) . . ?
O1 C2 C3 111.9(3) . . ?
C1 C2 C3 102.2(3) . . ?
O1 C2 H2 111(2) . . ?
C1 C2 H2 110(2) . . ?
C3 C2 H2 114(2) . . ?
O3 C3 C4 109.6(3) . . ?
O3 C3 C2 108.6(3) . . ?
C4 C3 C2 103.1(3) . . ?
O3 C3 H3 108(2) . . ?
C4 C3 H3 114(2) . . ?
C2 C3 H3 113(2) . . ?
O5 C4 C3 104.0(3) . . ?
O5 C4 C5 108.4(3) . . ?
C3 C4 C5 114.5(3) . . ?
O5 C4 H4 110(2) . . ?
C3 C4 H4 110(2) . . ?
C5 C4 H4 110(2) . . ?
O6 C5 C6 110.2(3) . . ?
O6 C5 C4 107.5(3) . . ?
C6 C5 C4 112.5(3) . . ?
O6 C5 H5 111(2) . . ?
C6 C5 H5 110(2) . . ?
C4 C5 H5 105(2) . . ?
C7 C6 N1 120.2(3) . . ?
C7 C6 C5 123.0(4) . . ?
N1 C6 C5 116.8(3) . . ?
C6 C7 C8 121.6(4) . . ?
C6 C7 H7 123(2) . . ?
C8 C7 H7 115(2) . . ?
O7 C8 N2 119.8(4) . . ?
O7 C8 C7 125.6(4) . . ?
N2 C8 C7 114.6(4) . . ?
O8 C9 N2 124.0(4) . . ?
O8 C9 N1 121.0(4) . . ?
N2 C9 N1 114.9(3) . . ?
O2 C10 O1 123.1(4) . . ?
O2 C10 C11 125.3(4) . . ?
O1 C10 C11 111.6(3) . . ?
C10 C11 H11A 112(3) . . ?
C10 C11 H11B 109(2) . . ?
H11A C11 H11B 108(2) . . ?
C10 C11 H11C 111(2) . . ?
H11A C11 H11C 109(2) . . ?
H11B C11 H11C 108(2) . . ?
O4 C12 O3 122.8(4) . . ?
O4 C12 C13 126.0(4) . . ?
O3 C12 C13 111.2(3) . . ?
C12 C13 H13A 110(3) . . ?
C12 C13 H13B 116(3) . . ?
H13A C13 H13B 109(2) . . ?
C12 C13 H13C 104(2) . . ?
H13A C13 H13C 108(2) . . ?
H13B C13 H13C 109(2) . . ?
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
C4 O5 C1 N1 -72.5(3) . . . . ?
C4 O5 C1 C2 43.8(3) . . . . ?
C6 N1 C1 O5 34.2(4) . . . . ?
C9 N1 C1 O5 -148.8(3) . . . . ?
C6 N1 C1 C2 -81.1(4) . . . . ?
C9 N1 C1 C2 95.9(4) . . . . ?
C10 O1 C2 C1 170.4(3) . . . . ?
C10 O1 C2 C3 -77.9(4) . . . . ?
O5 C1 C2 O1 94.2(3) . . . . ?
N1 C1 C2 O1 -149.7(3) . . . . ?
O5 C1 C2 C3 -23.9(3) . . . . ?
N1 C1 C2 C3 92.1(3) . . . . ?
C12 O3 C3 C4 -89.4(4) . . . . ?
C12 O3 C3 C2 158.7(3) . . . . ?
O1 C2 C3 O3 -3.3(4) . . . . ?
C1 C2 C3 O3 112.1(3) . . . . ?
O1 C2 C3 C4 -119.5(3) . . . . ?
C1 C2 C3 C4 -4.1(4) . . . . ?
C1 O5 C4 C3 -45.8(3) . . . . ?
C1 O5 C4 C5 76.4(3) . . . . ?
O3 C3 C4 O5 -85.6(3) . . . . ?
C2 C3 C4 O5 29.9(4) . . . . ?
O3 C3 C4 C5 156.2(3) . . . . ?
C2 C3 C4 C5 -88.3(4) . . . . ?
O5 C4 C5 O6 82.6(3) . . . . ?
C3 C4 C5 O6 -161.8(3) . . . . ?
O5 C4 C5 C6 -38.9(4) . . . . ?
C3 C4 C5 C6 76.7(4) . . . . ?
C9 N1 C6 C7 4.1(6) . . . . ?
C1 N1 C6 C7 -179.0(3) . . . . ?
C9 N1 C6 C5 -174.2(3) . . . . ?
C1 N1 C6 C5 2.6(5) . . . . ?
O6 C5 C6 C7 61.9(5) . . . . ?
C4 C5 C6 C7 -178.1(4) . . . . ?
O6 C5 C6 N1 -119.8(3) . . . . ?
C4 C5 C6 N1 0.2(5) . . . . ?
N1 C6 C7 C8 -2.5(6) . . . . ?
C5 C6 C7 C8 175.7(4) . . . . ?
C9 N2 C8 O7 177.5(4) . . . . ?
C9 N2 C8 C7 -1.6(6) . . . . ?
C6 C7 C8 O7 -177.8(4) . . . . ?
C6 C7 C8 N2 1.2(6) . . . . ?
C8 N2 C9 O8 -176.0(4) . . . . ?
C8 N2 C9 N1 3.0(6) . . . . ?
C6 N1 C9 O8 174.9(3) . . . . ?
C1 N1 C9 O8 -2.1(6) . . . . ?
C6 N1 C9 N2 -4.2(6) . . . . ?
C1 N1 C9 N2 178.8(3) . . . . ?
C2 O1 C10 O2 -4.7(6) . . . . ?
C2 O1 C10 C11 176.4(3) . . . . ?
C3 O3 C12 O4 0.3(6) . . . . ?
C3 O3 C12 C13 179.6(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
O1S H1SA O7 0.842(19) 1.96(2) 2.797(4) 172(4) .
O1S H1SB O7 0.844(19) 1.99(2) 2.821(4) 169(5) 2_455
O6 H6O O1S 0.883(18) 1.82(2) 2.680(4) 164(5) 1_545
N2 H2N O6 0.869(19) 2.11(2) 2.964(4) 168(4) 1_565
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 27.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.240
_refine_diff_density_min -0.311
_refine_diff_density_rms 0.061