data_jac03

 

_audit_creation_method            SHELXL-97

_chemical_name_systematic

;

 ?

;

_chemical_name_common             ?

_chemical_melting_point           ?

_chemical_formula_moiety          'C18 H18 N2 O6'

_chemical_formula_sum

 'C18 H18 N2 O6'

_chemical_formula_weight          358.34

 

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    P2(1)

 

loop_

 _symmetry_equiv_pos_as_xyz

 'x, y, z'

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

 

_cell_length_a                    9.8372(4)

_cell_length_b                    7.2818(3)

_cell_length_c                    11.6037(5)

_cell_angle_alpha                 90.00

_cell_angle_beta                  108.626(2)

_cell_angle_gamma                 90.00

_cell_volume                      787.67(6)

_cell_formula_units_Z             2

_cell_measurement_temperature     100(2)

_cell_measurement_reflns_used     6587

_cell_measurement_theta_min       2.18

_cell_measurement_theta_max       27.57

 

_exptl_crystal_description        Block

_exptl_crystal_colour             Colorless

_exptl_crystal_size_max           0.37

_exptl_crystal_size_mid           0.37

_exptl_crystal_size_min           0.30

_exptl_crystal_density_meas       .

_exptl_crystal_density_diffrn     1.511

_exptl_crystal_density_method     'not measured'

_exptl_crystal_F_000              376

_exptl_absorpt_coefficient_mu     0.115

_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   0.9587

_exptl_absorpt_correction_T_max   0.9664

_exptl_absorpt_process_details    ?

 

_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   'Bruker SMART 1000'

_diffrn_measurement_method        '\w scans at 7 \f settings'

_diffrn_detector_area_resol_mean  ?

_diffrn_reflns_number             24528

_diffrn_reflns_av_R_equivalents   0.0425

_diffrn_reflns_av_sigmaI/netI     0.0456

_diffrn_reflns_limit_h_min        -18

_diffrn_reflns_limit_h_max        18

_diffrn_reflns_limit_k_min        -13

_diffrn_reflns_limit_k_max        13

_diffrn_reflns_limit_l_min        -21

_diffrn_reflns_limit_l_max        21

_diffrn_reflns_theta_min          1.85

_diffrn_reflns_theta_max          42.08

_reflns_number_total              10286

_reflns_number_gt                 8534

_reflns_threshold_expression      >2sigma(I)

 

_computing_data_collection        'Bruker SMART v5.630'

_computing_cell_refinement        'Bruker SAINT-Plus v7.66A'

_computing_data_reduction         'Bruker SAINT-Plus v7.66A'

_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics     'Bruker XP v5.1'

_computing_publication_material   'Bruker XCIF 2008'

 

_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 matrix' 
_refine_ls_weighting_scheme       Sigma
_refine_ls_weighting_details      'w=1/s^2^(Fo^2^)' 
_atom_sites_solution_primary      'Direct methods'
_atom_sites_solution_secondary    'Difference Fourier map'
_atom_sites_solution_hydrogens    'Difference Fourier map'
_refine_ls_hydrogen_treatment     Unrestrained
_chemical_absolute_configuration  ?
_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    0.1(5)

_refine_ls_number_reflns          10286

_refine_ls_number_parameters      307

_refine_ls_number_restraints      1

_refine_ls_R_factor_all           0.0564

_refine_ls_R_factor_gt            0.0456

_refine_ls_wR_factor_ref          0.0781

_refine_ls_wR_factor_gt           0.0767

_refine_ls_goodness_of_fit_ref    1.822

_refine_ls_restrained_S_all       1.822

_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 0.83477(8) -0.17835(10) 0.46974(7) 0.02014(14) Uani 1 1 d . . .

O2 O 0.60706(9) -0.03271(11) 0.93892(7) 0.02229(16) Uani 1 1 d . . .

O3 O 0.57369(12) 0.49764(12) 0.73072(8) 0.0364(2) Uani 1 1 d . . .

O4 O 0.60356(8) 0.45898(10) 0.51417(6) 0.01922(15) Uani 1 1 d . . .

O5 O 0.91073(8) 0.35639(11) 0.08850(7) 0.02182(16) Uani 1 1 d . . .

O6 O 0.94447(8) -0.17716(10) 0.29267(7) 0.01972(14) Uani 1 1 d . . .

N1 N 0.70243(8) 0.19259(10) 0.60683(7) 0.01189(14) Uani 1 1 d . . .

N2 N 0.80577(8) 0.12401(11) 0.41236(7) 0.01240(14) Uani 1 1 d . . .

C1 C 0.81263(10) -0.01534(13) 0.48941(8) 0.01342(16) Uani 1 1 d . . .

C2 C 0.80025(10) 0.03630(12) 0.61304(8) 0.01272(15) Uani 1 1 d . . .

C3 C 0.73507(11) -0.11622(13) 0.66837(9) 0.01481(17) Uani 1 1 d . . .

C4 C 0.66906(10) -0.01219(13) 0.74988(8) 0.01342(16) Uani 1 1 d . . .

C5 C 0.66652(11) -0.08968(15) 0.85308(9) 0.01714(18) Uani 1 1 d . . .

C6 C 0.55833(12) 0.14256(16) 0.94153(10) 0.0206(2) Uani 1 1 d . . .

C7 C 0.57167(13) 0.29186(16) 0.88103(10) 0.0222(2) Uani 1 1 d . . .

C8 C 0.64053(12) 0.33096(14) 0.78522(9) 0.01915(19) Uani 1 1 d . . .

C9 C 0.61760(10) 0.17231(13) 0.69302(8) 0.01261(15) Uani 1 1 d . . .

C10 C 0.68548(9) 0.32645(13) 0.52491(8) 0.01261(15) Uani 1 1 d . . .

C11 C 0.77990(9) 0.31425(13) 0.44371(8) 0.01233(15) Uani 1 1 d . . .

C12 C 0.71347(11) 0.40373(14) 0.31997(9) 0.01555(17) Uani 1 1 d . . .

C13 C 0.79161(10) 0.30805(14) 0.24404(8) 0.01403(16) Uani 1 1 d . . .

C14 C 0.83973(11) 0.40550(15) 0.16816(9) 0.01742(18) Uani 1 1 d . . .

C15 C 0.94494(11) 0.17758(16) 0.07407(9) 0.01893(19) Uani 1 1 d . . .

C16 C 0.95833(12) 0.03528(16) 0.14812(9) 0.01917(19) Uani 1 1 d . . .

C17 C 0.94503(10) 0.01596(14) 0.27300(9) 0.01487(16) Uani 1 1 d . . .

C18 C 0.80871(10) 0.10871(13) 0.28346(8) 0.01284(15) Uani 1 1 d . . .

H3 H 0.5794(18) 0.496(3) 0.6606(14) 0.051(5) Uiso 1 1 d . . .

H6 H 0.9043(14) -0.189(2) 0.3463(11) 0.032(4) Uiso 1 1 d . . .

H2 H 0.8996(11) 0.0669(14) 0.6656(9) 0.003(2) Uiso 1 1 d . . .

H3A H 0.6590(12) -0.1706(18) 0.6037(10) 0.013(3) Uiso 1 1 d . . .

H3B H 0.8040(13) -0.1983(19) 0.7104(11) 0.021(3) Uiso 1 1 d . . .

H5 H 0.7075(13) -0.2035(19) 0.8718(11) 0.022(3) Uiso 1 1 d . . .

H6A H 0.5086(14) 0.1432(17) 0.9974(13) 0.018(3) Uiso 1 1 d . . .

H7 H 0.5272(15) 0.397(2) 0.8980(12) 0.034(4) Uiso 1 1 d . . .

H8 H 0.7436(13) 0.3600(18) 0.8181(10) 0.023(3) Uiso 1 1 d . . .

H9 H 0.5163(12) 0.1697(17) 0.6458(10) 0.014(3) Uiso 1 1 d . . .

H11 H 0.8687(12) 0.3694(16) 0.4850(9) 0.010(3) Uiso 1 1 d . . .

H12A H 0.6089(12) 0.3711(16) 0.2898(10) 0.013(3) Uiso 1 1 d . . .

H12B H 0.7244(13) 0.5419(18) 0.3235(11) 0.017(3) Uiso 1 1 d . . .

H14 H 0.8278(13) 0.5295(18) 0.1621(11) 0.019(3) Uiso 1 1 d . . .

H15 H 0.9612(13) 0.1605(18) -0.0045(12) 0.022(3) Uiso 1 1 d . . .

H16 H 0.9814(11) -0.0782(17) 0.1168(9) 0.013(3) Uiso 1 1 d . . .

H17 H 1.0269(13) 0.0679(17) 0.3350(11) 0.015(3) Uiso 1 1 d . . .

H18 H 0.7275(12) 0.0325(16) 0.2409(10) 0.012(3) Uiso 1 1 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 0.0321(4) 0.0098(3) 0.0241(4) 0.0006(3) 0.0168(3) 0.0039(3)

O2 0.0327(4) 0.0205(4) 0.0204(3) 0.0028(3) 0.0179(3) 0.0009(3)

O3 0.0794(7) 0.0123(4) 0.0315(5) 0.0022(4) 0.0374(5) 0.0066(4)

O4 0.0269(4) 0.0158(3) 0.0171(3) 0.0026(3) 0.0099(3) 0.0099(3)

O5 0.0302(4) 0.0203(4) 0.0213(3) 0.0019(3) 0.0172(3) 0.0007(3)

O6 0.0285(4) 0.0124(3) 0.0235(4) 0.0012(3) 0.0156(3) 0.0043(3)

N1 0.0153(3) 0.0088(3) 0.0136(3) 0.0010(3) 0.0075(3) 0.0011(3)

N2 0.0169(3) 0.0093(3) 0.0126(3) 0.0000(3) 0.0070(3) 0.0020(3)

C1 0.0147(4) 0.0114(4) 0.0154(4) 0.0004(3) 0.0066(3) 0.0009(3)

C2 0.0142(4) 0.0114(4) 0.0140(4) 0.0011(3) 0.0066(3) 0.0009(3)

C3 0.0203(4) 0.0102(4) 0.0160(4) 0.0025(3) 0.0089(3) 0.0019(3)

C4 0.0157(4) 0.0111(4) 0.0148(4) -0.0007(3) 0.0068(3) -0.0017(3)

C5 0.0199(4) 0.0159(4) 0.0180(4) 0.0021(4) 0.0094(3) 0.0002(4)

C6 0.0266(5) 0.0206(5) 0.0184(4) -0.0018(4) 0.0127(4) -0.0010(4)

C7 0.0358(6) 0.0174(5) 0.0189(5) -0.0033(4) 0.0165(4) 0.0003(4)

C8 0.0290(5) 0.0139(4) 0.0183(4) -0.0048(4) 0.0128(4) -0.0044(4)

C9 0.0149(4) 0.0106(4) 0.0141(4) -0.0017(3) 0.0071(3) -0.0016(3)

C10 0.0155(4) 0.0111(4) 0.0115(3) -0.0013(3) 0.0046(3) 0.0001(3)

C11 0.0157(4) 0.0100(3) 0.0119(3) -0.0002(3) 0.0052(3) 0.0011(3)

C12 0.0206(4) 0.0134(4) 0.0138(4) 0.0025(3) 0.0071(3) 0.0045(3)

C13 0.0164(4) 0.0139(4) 0.0113(4) 0.0000(3) 0.0039(3) 0.0013(3)

C14 0.0231(5) 0.0149(4) 0.0152(4) 0.0007(4) 0.0076(3) 0.0012(4)

C15 0.0216(4) 0.0220(5) 0.0158(4) -0.0017(4) 0.0095(4) 0.0011(4)

C16 0.0223(5) 0.0205(5) 0.0181(4) -0.0023(4) 0.0112(4) 0.0026(4)

C17 0.0157(4) 0.0143(4) 0.0154(4) -0.0006(3) 0.0060(3) 0.0015(3)

C18 0.0152(4) 0.0123(4) 0.0113(3) -0.0009(3) 0.0047(3) 0.0001(3)

 

_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 1.2410(12) . ?

O2 C6 1.3671(14) . ?

O2 C5 1.3706(12) . ?

O3 C8 1.4282(14) . ?

O3 H3 0.834(15) . ?

O4 C10 1.2378(12) . ?

O5 C15 1.3685(13) . ?

O5 C14 1.3719(12) . ?

O6 C17 1.4250(13) . ?

O6 H6 0.842(13) . ?

N1 C10 1.3342(12) . ?

N1 C2 1.4772(11) . ?

N1 C9 1.5006(11) . ?

N2 C1 1.3399(12) . ?

N2 C11 1.4748(12) . ?

N2 C18 1.5094(11) . ?

C1 C2 1.5250(12) . ?

C2 C3 1.5231(12) . ?

C2 H2 0.998(10) . ?

C3 C4 1.5107(13) . ?

C3 H3A 0.960(11) . ?

C3 H3B 0.919(13) . ?

C4 C5 1.3312(13) . ?

C4 C9 1.5110(13) . ?

C5 H5 0.917(14) . ?

C6 C7 1.3232(15) . ?

C6 H6A 0.929(13) . ?

C7 C8 1.5024(13) . ?

C7 H7 0.935(14) . ?

C8 C9 1.5415(13) . ?

C8 H8 0.985(12) . ?

C9 H9 0.972(11) . ?

C10 C11 1.5222(12) . ?

C11 C12 1.5212(13) . ?

C11 H11 0.941(11) . ?

C12 C13 1.5118(13) . ?

C12 H12A 1.004(11) . ?

C12 H12B 1.011(13) . ?

C13 C14 1.3301(13) . ?

C13 C18 1.5151(14) . ?

C14 H14 0.910(13) . ?

C15 C16 1.3255(15) . ?

C15 H15 0.982(13) . ?

C16 C17 1.5025(13) . ?

C16 H16 0.958(12) . ?

C17 C18 1.5405(13) . ?

C17 H17 0.969(12) . ?

C18 H18 0.969(12) . ?

 

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

C6 O2 C5 122.19(8) . . ?

C8 O3 H3 104.9(13) . . ?

C15 O5 C14 121.90(8) . . ?

C17 O6 H6 104.5(11) . . ?

C10 N1 C2 121.93(7) . . ?

C10 N1 C9 125.25(7) . . ?

C2 N1 C9 112.58(7) . . ?

C1 N2 C11 121.51(7) . . ?

C1 N2 C18 126.34(8) . . ?

C11 N2 C18 111.92(7) . . ?

O1 C1 N2 125.17(8) . . ?

O1 C1 C2 118.70(8) . . ?

N2 C1 C2 116.03(8) . . ?

N1 C2 C3 103.12(7) . . ?

N1 C2 C1 112.99(7) . . ?

C3 C2 C1 112.80(8) . . ?

N1 C2 H2 110.7(6) . . ?

C3 C2 H2 111.5(6) . . ?

C1 C2 H2 105.9(6) . . ?

C4 C3 C2 102.78(7) . . ?

C4 C3 H3A 108.2(7) . . ?

C2 C3 H3A 107.4(7) . . ?

C4 C3 H3B 112.7(8) . . ?

C2 C3 H3B 111.0(8) . . ?

H3A C3 H3B 114.0(11) . . ?

C5 C4 C3 119.07(9) . . ?

C5 C4 C9 132.05(9) . . ?

C3 C4 C9 108.87(7) . . ?

C4 C5 O2 131.33(10) . . ?

C4 C5 H5 117.6(8) . . ?

O2 C5 H5 111.0(8) . . ?

C7 C6 O2 131.33(9) . . ?

C7 C6 H6A 122.0(8) . . ?

O2 C6 H6A 106.7(8) . . ?

C6 C7 C8 133.86(10) . . ?

C6 C7 H7 115.5(8) . . ?

C8 C7 H7 110.6(8) . . ?

O3 C8 C7 103.66(8) . . ?

O3 C8 C9 112.64(8) . . ?

C7 C8 C9 111.77(8) . . ?

O3 C8 H8 105.1(8) . . ?

C7 C8 H8 113.9(7) . . ?

C9 C8 H8 109.5(7) . . ?

N1 C9 C4 101.45(7) . . ?

N1 C9 C8 113.55(7) . . ?

C4 C9 C8 114.14(8) . . ?

N1 C9 H9 108.3(7) . . ?

C4 C9 H9 111.6(7) . . ?

C8 C9 H9 107.6(7) . . ?

O4 C10 N1 124.78(8) . . ?

O4 C10 C11 119.31(8) . . ?

N1 C10 C11 115.86(8) . . ?

N2 C11 C12 103.03(7) . . ?

N2 C11 C10 113.26(8) . . ?

C12 C11 C10 113.34(7) . . ?

N2 C11 H11 108.7(7) . . ?

C12 C11 H11 110.3(7) . . ?

C10 C11 H11 108.1(6) . . ?

C13 C12 C11 101.98(8) . . ?

C13 C12 H12A 110.0(7) . . ?

C11 C12 H12A 108.1(6) . . ?

C13 C12 H12B 114.5(7) . . ?

C11 C12 H12B 112.3(7) . . ?

H12A C12 H12B 109.5(10) . . ?

C14 C13 C12 119.65(9) . . ?

C14 C13 C18 133.03(9) . . ?

C12 C13 C18 107.08(8) . . ?

C13 C14 O5 132.25(10) . . ?

C13 C14 H14 121.0(8) . . ?

O5 C14 H14 106.7(8) . . ?

C16 C15 O5 129.93(9) . . ?

C16 C15 H15 119.4(8) . . ?

O5 C15 H15 110.7(8) . . ?

C15 C16 C17 132.62(10) . . ?

C15 C16 H16 114.5(7) . . ?

C17 C16 H16 112.9(7) . . ?

O6 C17 C16 104.65(8) . . ?

O6 C17 C18 111.84(8) . . ?

C16 C17 C18 112.40(8) . . ?

O6 C17 H17 108.1(7) . . ?

C16 C17 H17 111.9(7) . . ?

C18 C17 H17 107.9(7) . . ?

N2 C18 C13 101.13(7) . . ?

N2 C18 C17 113.78(7) . . ?

C13 C18 C17 114.32(7) . . ?

N2 C18 H18 105.9(7) . . ?

C13 C18 H18 113.6(7) . . ?

C17 C18 H18 107.8(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

O3 H3 O4  0.834(15) 1.809(15) 2.6365(11) 171.2(19) .

O6 H6 O1  0.842(13) 1.775(13) 2.6082(10) 169.9(15) .

 

_diffrn_measured_fraction_theta_max    0.977

_diffrn_reflns_theta_full              42.08

_diffrn_measured_fraction_theta_full   0.977

_refine_diff_density_max    0.524

_refine_diff_density_min   -0.394

_refine_diff_density_rms    0.067