 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C5 H8 N O3, C4 H12 N'
_chemical_formula_sum
 'C9 H20 N2 O3'
_chemical_formula_weight          204.27
 
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    P21212
 
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                    18.5858(10)
_cell_length_b                    7.6490(3)
_cell_length_c                    8.0285(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1141.35(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     9155
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.189
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              448
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type    multi-scan

_exptl_absorpt_correction_T_min   0.9890
_exptl_absorpt_correction_T_max   0.9937
_exptl_absorpt_process_details    
'SADABS V2.10 (Sheldrick, 2003)' 

 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             6869
_diffrn_reflns_av_R_equivalents   0.0490
_diffrn_reflns_av_sigmaI/netI     0.0411
_diffrn_reflns_limit_h_min        -20
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.35
_diffrn_reflns_theta_max          25.21
_reflns_number_total              1217
_reflns_number_gt                 982
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0607P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.018(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1217
_refine_ls_number_parameters      138
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0520
_refine_ls_R_factor_gt            0.0385
_refine_ls_wR_factor_ref          0.0970
_refine_ls_wR_factor_gt           0.0920
_refine_ls_goodness_of_fit_ref    1.052
_refine_ls_restrained_S_all       1.052
_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
N1 N 0.00239(11) 0.2313(2) 0.3682(2) 0.0284(5) Uani 1 1 d D . .
H1N H -0.0309(11) 0.159(3) 0.338(3) 0.038(7) Uiso 1 1 d D . .
O1 O 0.06853(9) 0.3448(2) 0.5765(2) 0.0447(5) Uani 1 1 d . . .
O2 O 0.11761(9) 0.0091(2) 0.3047(2) 0.0393(5) Uani 1 1 d . . .
O3 O 0.18023(8) 0.2304(2) 0.1965(2) 0.0395(5) Uani 1 1 d . . .
C1 C -0.04561(14) 0.2187(4) 0.6464(3) 0.0443(7) Uani 1 1 d . . .
H1A H -0.0249 0.1653 0.7464 0.066 Uiso 1 1 calc R . .
H1B H -0.0778 0.1350 0.5918 0.066 Uiso 1 1 calc R . .
H1C H -0.0728 0.3234 0.6777 0.066 Uiso 1 1 calc R . .
C2 C 0.01373(13) 0.2687(3) 0.5285(3) 0.0326(6) Uani 1 1 d . . .
C3 C 0.05579(12) 0.2763(3) 0.2445(3) 0.0287(6) Uani 1 1 d . . .
H3 H 0.0706 0.4004 0.2639 0.034 Uiso 1 1 calc R . .
C4 C 0.02256(13) 0.2648(3) 0.0699(3) 0.0360(6) Uani 1 1 d . . .
H4A H 0.0089 0.1435 0.0466 0.054 Uiso 1 1 calc R . .
H4B H 0.0578 0.3040 -0.0129 0.054 Uiso 1 1 calc R . .
H4C H -0.0202 0.3394 0.0645 0.054 Uiso 1 1 calc R . .
C5 C 0.12390(12) 0.1622(3) 0.2510(3) 0.0287(6) Uani 1 1 d . . .
N2 N 0.25161(10) 0.6858(2) 0.2399(2) 0.0308(5) Uani 1 1 d . . .
C6 C 0.22205(17) 0.6725(4) 0.4115(3) 0.0499(8) Uani 1 1 d . . .
H6A H 0.1972 0.5603 0.4245 0.075 Uiso 1 1 calc R . .
H6B H 0.1880 0.7683 0.4307 0.075 Uiso 1 1 calc R . .
H6C H 0.2614 0.6800 0.4923 0.075 Uiso 1 1 calc R . .
C7 C 0.30575(15) 0.5460(3) 0.2117(4) 0.0450(7) Uani 1 1 d . . .
H7A H 0.3455 0.5598 0.2910 0.068 Uiso 1 1 calc R . .
H7B H 0.3243 0.5544 0.0978 0.068 Uiso 1 1 calc R . .
H7C H 0.2832 0.4314 0.2279 0.068 Uiso 1 1 calc R . .
C8 C 0.19195(13) 0.6692(3) 0.1176(3) 0.0359(6) Uani 1 1 d . . .
H8A H 0.1688 0.5550 0.1306 0.054 Uiso 1 1 calc R . .
H8B H 0.2112 0.6798 0.0044 0.054 Uiso 1 1 calc R . .
H8C H 0.1566 0.7620 0.1371 0.054 Uiso 1 1 calc R . .
C9 C 0.28665(14) 0.8598(3) 0.2156(4) 0.0383(6) Uani 1 1 d . . .
H9A H 0.2512 0.9527 0.2339 0.058 Uiso 1 1 calc R . .
H9B H 0.3054 0.8679 0.1018 0.058 Uiso 1 1 calc R . .
H9C H 0.3263 0.8728 0.2951 0.058 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
N1 0.0236(10) 0.0292(11) 0.0325(11) -0.0014(9) -0.0003(9) -0.0031(9)
O1 0.0348(10) 0.0530(11) 0.0462(11) -0.0047(9) -0.0108(9) -0.0080(9)
O2 0.0314(9) 0.0286(9) 0.0579(12) 0.0068(8) 0.0051(9) 0.0016(7)
O3 0.0268(9) 0.0378(10) 0.0541(12) 0.0081(8) 0.0091(9) -0.0004(8)
C1 0.0453(16) 0.0524(16) 0.0351(15) 0.0020(13) 0.0025(13) -0.0022(13)
C2 0.0303(14) 0.0301(13) 0.0375(15) -0.0005(11) -0.0031(12) 0.0009(11)
C3 0.0264(12) 0.0251(11) 0.0348(13) 0.0022(10) 0.0022(11) -0.0006(10)
C4 0.0368(14) 0.0355(14) 0.0356(13) 0.0053(12) 0.0012(12) 0.0039(11)
C5 0.0277(13) 0.0268(12) 0.0316(13) -0.0007(10) 0.0020(11) 0.0002(10)
N2 0.0284(10) 0.0276(11) 0.0364(12) 0.0016(9) -0.0008(10) 0.0029(8)
C6 0.0630(19) 0.0528(18) 0.0340(15) 0.0044(14) 0.0009(15) 0.0102(15)
C7 0.0374(15) 0.0301(14) 0.068(2) 0.0014(12) -0.0035(15) 0.0091(12)
C8 0.0342(13) 0.0356(13) 0.0379(15) -0.0005(11) -0.0036(12) -0.0010(12)
C9 0.0306(13) 0.0314(13) 0.0531(18) -0.0026(12) -0.0050(13) 0.0004(11)
 
_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
N1 C2 1.335(3) . ?
N1 C3 1.446(3) . ?
N1 H1N 0.864(17) . ?
O1 C2 1.235(3) . ?
O2 C5 1.254(3) . ?
O3 C5 1.249(3) . ?
C1 C2 1.502(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.534(3) . ?
C3 C5 1.538(3) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N2 C7 1.486(3) . ?
N2 C6 1.486(3) . ?
N2 C8 1.487(3) . ?
N2 C9 1.495(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
 
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
C2 N1 C3 120.2(2) . . ?
C2 N1 H1N 121.1(18) . . ?
C3 N1 H1N 117.0(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 122.1(2) . . ?
O1 C2 C1 121.9(2) . . ?
N1 C2 C1 115.9(2) . . ?
N1 C3 C4 109.74(18) . . ?
N1 C3 C5 113.97(18) . . ?
C4 C3 C5 109.2(2) . . ?
N1 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
C5 C3 H3 107.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O3 C5 O2 126.1(2) . . ?
O3 C5 C3 116.16(18) . . ?
O2 C5 C3 117.7(2) . . ?
C7 N2 C6 110.0(2) . . ?
C7 N2 C8 110.08(19) . . ?
C6 N2 C8 109.31(19) . . ?
C7 N2 C9 109.02(17) . . ?
C6 N2 C9 110.1(2) . . ?
C8 N2 C9 108.34(18) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
N1 H1N O2  0.864(17) 2.078(18) 2.935(3) 171(3) 2
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.156
_refine_diff_density_min   -0.162
_refine_diff_density_rms    0.038
_chemical_absolute_configuration unk
