 
data_2009src0683a
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C14 H17 N O8'
_chemical_formula_sum
 'C14 H17 N O8'
_chemical_formula_weight          327.29
_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   0.0000
 '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   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    'P 21 21 21'
_symmetry_space_group_name_Hall   'P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    4.75500(10)
_cell_length_b                    12.4624(3)
_cell_length_c                    24.7840(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1468.67(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     28436
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.07
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.480
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              688
_exptl_absorpt_coefficient_mu     0.123
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9758
_exptl_absorpt_correction_T_max   0.9988
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)'
 
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
 Ratio of minimum to maximum apparent transmission: 0.781152
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   66.0645
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             17643
_diffrn_reflns_av_R_equivalents   0.0617
_diffrn_reflns_av_sigmaI/netI     0.0397
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -32
_diffrn_reflns_limit_l_max        32
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1992
_reflns_number_gt                 1738
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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 > 2σ(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)+(0.0053P)²+1.7875P] 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_number_reflns          1992
_refine_ls_number_parameters      216
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0618
_refine_ls_R_factor_gt            0.0492
_refine_ls_wR_factor_ref          0.0923
_refine_ls_wR_factor_gt           0.0863
_refine_ls_goodness_of_fit_ref    1.099
_refine_ls_restrained_S_all       1.099
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.4034(7) 0.9381(2) 0.82416(11) 0.0162(7) Uani 1 1 d . . .
H1 H 0.5797 0.9595 0.8050 0.019 Uiso 1 1 calc R . .
C2 C 0.3293(7) 0.8220(2) 0.80955(11) 0.0139(6) Uani 1 1 d . . .
H2 H 0.4893 0.7747 0.8205 0.017 Uiso 1 1 calc R . .
C3 C 0.0672(7) 0.7867(2) 0.84001(11) 0.0135(6) Uani 1 1 d . . .
H3 H -0.0932 0.8347 0.8301 0.016 Uiso 1 1 calc R . .
C4 C 0.1261(7) 0.7972(2) 0.90010(11) 0.0153(6) Uani 1 1 d . . .
H4 H 0.2851 0.7489 0.9105 0.018 Uiso 1 1 calc R . .
C5 C 0.2043(7) 0.9144(2) 0.91212(11) 0.0168(7) Uani 1 1 d . . .
H5 H 0.0421 0.9612 0.9018 0.020 Uiso 1 1 calc R . .
C6 C 0.2785(8) 0.9365(2) 0.97060(11) 0.0198(7) Uani 1 1 d . . .
H6A H 0.3371 1.0124 0.9741 0.024 Uiso 1 1 calc R . .
H6B H 0.1083 0.9263 0.9930 0.024 Uiso 1 1 calc R . .
C7 C 0.4615(7) 0.7546(2) 0.71997(11) 0.0149(6) Uani 1 1 d . . .
C8 C 0.4055(7) 0.7668(2) 0.66027(11) 0.0151(6) Uani 1 1 d . . .
C9 C 0.2354(7) 0.6902(2) 0.63562(12) 0.0194(7) Uani 1 1 d . . .
H9 H 0.1671 0.6308 0.6558 0.023 Uiso 1 1 calc R . .
C10 C 0.1662(8) 0.7010(3) 0.58142(12) 0.0244(8) Uani 1 1 d . . .
H10 H 0.0501 0.6488 0.5645 0.029 Uiso 1 1 calc R . .
C11 C 0.2653(8) 0.7871(3) 0.55190(12) 0.0238(8) Uani 1 1 d . . .
H11 H 0.2155 0.7944 0.5150 0.029 Uiso 1 1 calc R . .
C12 C 0.4370(8) 0.8629(3) 0.57610(12) 0.0232(8) Uani 1 1 d . . .
H12 H 0.5070 0.9216 0.5556 0.028 Uiso 1 1 calc R . .
C13 C 0.5073(7) 0.8532(2) 0.63059(12) 0.0165(7) Uani 1 1 d . . .
C14 C 0.6978(8) 0.9342(2) 0.65614(12) 0.0198(7) Uani 1 1 d . . .
N1 N 0.2936(6) 0.81409(19) 0.75118(9) 0.0153(5) Uani 1 1 d D . .
O1 O 0.4457(5) 0.94607(16) 0.88088(8) 0.0164(5) Uani 1 1 d . . .
O2 O 0.1804(5) 1.00312(16) 0.80663(9) 0.0174(5) Uani 1 1 d . . .
H2A H 0.2421 1.0642 0.7986 0.026 Uiso 1 1 calc R . .
O3 O -0.0049(5) 0.67822(16) 0.82760(8) 0.0188(5) Uani 1 1 d . . .
H3A H -0.1041 0.6768 0.7996 0.028 Uiso 1 1 calc R . .
O4 O -0.1197(5) 0.76948(17) 0.93003(8) 0.0202(5) Uani 1 1 d . . .
H4A H -0.0778 0.7242 0.9538 0.030 Uiso 1 1 calc R . .
O5 O 0.4969(6) 0.86972(18) 0.99096(8) 0.0229(5) Uani 1 1 d . . .
H5A H 0.6054 0.8525 0.9657 0.034 Uiso 1 1 calc R . .
O6 O 0.6411(5) 0.69080(16) 0.73719(8) 0.0182(5) Uani 1 1 d . . .
O7 O 0.8105(5) 0.92139(17) 0.69938(9) 0.0225(5) Uani 1 1 d . . .
O8 O 0.7297(8) 1.02134(19) 0.62642(10) 0.0436(8) Uani 1 1 d . . .
H8 H 0.8272 1.0663 0.6434 0.065 Uiso 1 1 calc R . .
H1N H 0.147(7) 0.861(3) 0.7357(15) 0.052 Uiso 1 1 d D . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 O2 1.404(4) . ?
C1 O1 1.424(3) . ?
C1 C2 1.532(4) . ?
C1 H1 1.0000 . ?
C2 N1 1.460(3) . ?
C2 C3 1.522(4) . ?
C2 H2 1.0000 . ?
C3 O3 1.429(3) . ?
C3 C4 1.521(4) . ?
C3 H3 1.0000 . ?
C4 O4 1.427(4) . ?
C4 C5 1.536(4) . ?
C4 H4 1.0000 . ?
C5 O1 1.440(4) . ?
C5 C6 1.517(4) . ?
C5 H5 1.0000 . ?
C6 O5 1.423(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O6 1.243(4) . ?
C7 N1 1.336(4) . ?
C7 C8 1.511(4) . ?
C8 C13 1.390(4) . ?
C8 C9 1.393(4) . ?
C9 C10 1.390(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.497(5) . ?
C14 O7 1.209(4) . ?
C14 O8 1.321(4) . ?
N1 H1N 0.985(19) . ?
O2 H2A 0.8400 . ?
O3 H3A 0.8400 . ?
O4 H4A 0.8400 . ?
O5 H5A 0.8400 . ?
O8 H8 0.8400 . ?
 
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
O2 C1 O1 111.8(2) . . ?
O2 C1 C2 107.4(3) . . ?
O1 C1 C2 109.4(2) . . ?
O2 C1 H1 109.4 . . ?
O1 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
N1 C2 C3 112.1(3) . . ?
N1 C2 C1 108.9(2) . . ?
C3 C2 C1 110.1(2) . . ?
N1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
O3 C3 C4 109.7(2) . . ?
O3 C3 C2 111.3(2) . . ?
C4 C3 C2 108.0(2) . . ?
O3 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
O4 C4 C3 109.7(3) . . ?
O4 C4 C5 109.1(2) . . ?
C3 C4 C5 108.4(2) . . ?
O4 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
O1 C5 C6 106.2(3) . . ?
O1 C5 C4 110.4(2) . . ?
C6 C5 C4 114.4(2) . . ?
O1 C5 H5 108.5 . . ?
C6 C5 H5 108.5 . . ?
C4 C5 H5 108.5 . . ?
O5 C6 C5 113.7(3) . . ?
O5 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
O5 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O6 C7 N1 124.5(3) . . ?
O6 C7 C8 121.5(3) . . ?
N1 C7 C8 113.9(3) . . ?
C13 C8 C9 120.1(3) . . ?
C13 C8 C7 122.3(3) . . ?
C9 C8 C7 117.6(3) . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 119.7(3) . . ?
C8 C13 C14 120.6(3) . . ?
C12 C13 C14 119.7(3) . . ?
O7 C14 O8 123.5(3) . . ?
O7 C14 C13 123.6(3) . . ?
O8 C14 C13 112.8(3) . . ?
C7 N1 C2 122.8(3) . . ?
C7 N1 H1N 122(2) . . ?
C2 N1 H1N 115(2) . . ?
C1 O1 C5 113.5(2) . . ?
C1 O2 H2A 109.5 . . ?
C3 O3 H3A 109.5 . . ?
C4 O4 H4A 109.5 . . ?
C6 O5 H5A 109.5 . . ?
C14 O8 H8 109.5 . . ?
 
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
O2 H2A O6  0.84 1.89 2.715(3) 165.7 3_656
O3 H3A O6  0.84 1.97 2.807(3) 172.6 1_455
O4 H4A O5  0.84 1.84 2.674(3) 176.0 4_467
O5 H5A O4  0.84 1.89 2.677(3) 156.3 1_655
O8 H8 O3  0.84 1.78 2.614(3) 170.3 3_656
N1 H1N O7  0.985(19) 1.99(2) 2.952(3) 166(4) 1_455
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.266
_refine_diff_density_min   -0.273
_refine_diff_density_rms    0.061
