 
data_2007may0006
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H9 N O2'
_chemical_formula_weight          175.18
 
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    P2(1)2(1)2(1)
 
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                    7.3989(3)
_cell_length_b                    11.2007(4)
_cell_length_c                    20.2402(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1677.36(11)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     15878
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut rod'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.387
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              736
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9712
_exptl_absorpt_correction_T_max   0.9903
_exptl_absorpt_process_details    
'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
The values for Tmin and Tmax are based on cell
dimensions only and were generated using the size 
command in SHELX. SADABS estimates the minimum and maximum 
transmission as 0.6259 and 0.7456, respectively. 
;
 
_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    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             15527
_diffrn_reflns_av_R_equivalents   0.0809
_diffrn_reflns_av_sigmaI/netI     0.0556
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -26
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          3.30
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2213
_reflns_number_gt                 1756
_reflns_threshold_expression      >2sigma(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, 1997)'
_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)+(0.0646P)²+0.3478P] 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        0.014(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
#_refine_ls_abs_structure_details
# 'Flack H D (1983), Acta Cryst. A39, 876-881'
#_refine_ls_abs_structure_Flack    -10(10)
_refine_ls_number_reflns          2213
_refine_ls_number_parameters      244
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0678
_refine_ls_R_factor_gt            0.0465
_refine_ls_wR_factor_ref          0.1212
_refine_ls_wR_factor_gt           0.1091
_refine_ls_goodness_of_fit_ref    1.050
_refine_ls_restrained_S_all       1.051
_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
C1 C 0.3971(4) 0.5009(3) 0.01150(13) 0.0241(6) Uani 1 1 d . . .
C2 C 0.2765(4) 0.5809(3) -0.02625(13) 0.0229(6) Uani 1 1 d . . .
C3 C 0.3535(4) 0.6770(3) -0.05886(13) 0.0237(6) Uani 1 1 d . . .
H3 H 0.4793 0.6932 -0.0562 0.028 Uiso 1 1 calc R . .
C4 C 0.2375(4) 0.7487(2) -0.09583(13) 0.0234(6) Uani 1 1 d . . .
C5 C 0.1221(4) 0.8882(3) -0.16159(14) 0.0300(7) Uani 1 1 d . . .
H5 H 0.1135 0.9555 -0.1899 0.036 Uiso 1 1 calc R . .
C6 C -0.0205(4) 0.8179(3) -0.14350(15) 0.0310(7) Uani 1 1 d . . .
H6 H -0.1430 0.8277 -0.1564 0.037 Uiso 1 1 calc R . .
C7 C 0.0506(4) 0.7266(3) -0.10132(13) 0.0250(6) Uani 1 1 d . . .
C8 C -0.0245(4) 0.6282(3) -0.06740(13) 0.0262(6) Uani 1 1 d . . .
H8 H -0.1502 0.6116 -0.0698 0.031 Uiso 1 1 calc R . .
C9 C 0.0896(4) 0.5567(3) -0.03069(13) 0.0249(6) Uani 1 1 d . . .
H9 H 0.0413 0.4898 -0.0079 0.030 Uiso 1 1 calc R . .
N1 N 0.2791(3) 0.8482(2) -0.13326(11) 0.0252(6) Uani 1 1 d . . .
O1 O 0.5662(3) 0.51819(18) 0.00845(9) 0.0294(5) Uani 1 1 d . . .
O2 O 0.3256(3) 0.4165(2) 0.04534(11) 0.0333(5) Uani 1 1 d D . .
H1O H 0.394(5) 0.363(3) 0.0651(17) 0.050 Uiso 1 1 d D . .
C10 C 0.4566(4) 0.9020(3) -0.14070(15) 0.0278(6) Uani 1 1 d . . .
H10A H 0.5184 0.8663 -0.1787 0.042 Uiso 1 1 calc R . .
H10B H 0.5279 0.8879 -0.1006 0.042 Uiso 1 1 calc R . .
H10C H 0.4435 0.9881 -0.1478 0.042 Uiso 1 1 calc R . .
C11 C 0.7162(4) 0.2795(3) 0.09504(14) 0.0253(6) Uani 1 1 d . . .
C12 C 0.8425(4) 0.1905(3) 0.12342(13) 0.0230(6) Uani 1 1 d . . .
C13 C 0.7757(4) 0.1031(3) 0.16537(13) 0.0230(6) Uani 1 1 d . . .
H13 H 0.6514 0.1000 0.1770 0.028 Uiso 1 1 calc R . .
C14 C 0.8995(4) 0.0202(2) 0.18966(13) 0.0219(6) Uani 1 1 d . . .
C15 C 1.0339(4) -0.1357(3) 0.23790(14) 0.0279(7) Uani 1 1 d . . .
H15 H 1.0507 -0.2060 0.2634 0.033 Uiso 1 1 calc R . .
C16 C 1.1672(4) -0.0780(3) 0.20401(13) 0.0282(7) Uani 1 1 d . . .
H16 H 1.2908 -0.1006 0.2017 0.034 Uiso 1 1 calc R . .
C17 C 1.0858(4) 0.0232(3) 0.17253(13) 0.0249(6) Uani 1 1 d . . .
C18 C 1.1495(4) 0.1147(3) 0.13141(14) 0.0275(7) Uani 1 1 d . . .
H18 H 1.2741 0.1201 0.1206 0.033 Uiso 1 1 calc R . .
C19 C 1.0271(4) 0.1970(3) 0.10692(13) 0.0263(6) Uani 1 1 d . . .
H19 H 1.0683 0.2588 0.0785 0.032 Uiso 1 1 calc R . .
C20 C 0.7018(4) -0.1116(3) 0.26095(15) 0.0313(7) Uani 1 1 d . . .
H20A H 0.7109 -0.1936 0.2775 0.047 Uiso 1 1 calc R . .
H20B H 0.6038 -0.1065 0.2285 0.047 Uiso 1 1 calc R . .
H20C H 0.6765 -0.0575 0.2979 0.047 Uiso 1 1 calc R . .
N2 N 0.8715(3) -0.0776(2) 0.22979(11) 0.0250(5) Uani 1 1 d . . .
O3 O 0.7833(3) 0.3604(2) 0.05798(11) 0.0348(5) Uani 1 1 d D . .
O4 O 0.5486(3) 0.2725(2) 0.10778(11) 0.0361(6) Uani 1 1 d . . .
H2O H 0.711(5) 0.410(3) 0.0388(18) 0.054 Uiso 1 1 d D . .
 
 
_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
C1 O1 1.267(4) . ?
C1 O2 1.282(4) . ?
C1 C2 1.477(4) . ?
C2 C3 1.385(4) . ?
C2 C9 1.412(4) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.383(4) . ?
C4 C7 1.409(4) . ?
C5 C6 1.366(4) . ?
C5 N1 1.371(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.432(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(4) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
N1 C10 1.453(4) . ?
O2 H1O 0.879(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O4 1.269(4) . ?
C11 O3 1.276(4) . ?
C11 C12 1.482(4) . ?
C12 C13 1.386(4) . ?
C12 C19 1.408(4) . ?
C13 C14 1.395(4) . ?
C13 H13 0.9500 . ?
C14 N2 1.379(4) . ?
C14 C17 1.421(4) . ?
C15 C16 1.365(4) . ?
C15 N2 1.376(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.433(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.402(4) . ?
C18 C19 1.384(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 N2 1.456(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O3 H2O 0.863(19) . ?
 
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
O1 C1 O2 123.1(3) . . ?
O1 C1 C2 118.6(3) . . ?
O2 C1 C2 118.3(3) . . ?
C3 C2 C9 121.4(3) . . ?
C3 C2 C1 118.0(3) . . ?
C9 C2 C1 120.5(3) . . ?
C2 C3 C4 116.7(3) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
N1 C4 C3 128.4(3) . . ?
N1 C4 C7 108.5(3) . . ?
C3 C4 C7 123.1(3) . . ?
C6 C5 N1 110.8(3) . . ?
C6 C5 H5 124.6 . . ?
N1 C5 H5 124.6 . . ?
C5 C6 C7 106.7(3) . . ?
C5 C6 H6 126.7 . . ?
C7 C6 H6 126.7 . . ?
C4 C7 C8 119.0(3) . . ?
C4 C7 C6 106.4(3) . . ?
C8 C7 C6 134.6(3) . . ?
C9 C8 C7 118.3(3) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C2 121.5(3) . . ?
C8 C9 H9 119.3 . . ?
C2 C9 H9 119.3 . . ?
C5 N1 C4 107.7(2) . . ?
C5 N1 C10 126.0(2) . . ?
C4 N1 C10 126.4(2) . . ?
C1 O2 H1O 120(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O3 122.9(3) . . ?
O4 C11 C12 119.7(3) . . ?
O3 C11 C12 117.4(3) . . ?
C13 C12 C19 121.8(3) . . ?
C13 C12 C11 119.2(3) . . ?
C19 C12 C11 119.0(3) . . ?
C12 C13 C14 116.9(3) . . ?
C12 C13 H13 121.6 . . ?
C14 C13 H13 121.6 . . ?
N2 C14 C13 129.6(3) . . ?
N2 C14 C17 107.9(2) . . ?
C13 C14 C17 122.4(3) . . ?
C16 C15 N2 110.3(3) . . ?
C16 C15 H15 124.9 . . ?
N2 C15 H15 124.9 . . ?
C15 C16 C17 107.1(3) . . ?
C15 C16 H16 126.4 . . ?
C17 C16 H16 126.4 . . ?
C18 C17 C14 119.2(3) . . ?
C18 C17 C16 134.5(3) . . ?
C14 C17 C16 106.3(3) . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C12 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C12 C19 H19 119.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 N2 C14 108.3(2) . . ?
C15 N2 C20 125.3(2) . . ?
C14 N2 C20 126.3(2) . . ?
C11 O3 H2O 118(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
O2 H1O O4  0.879(19) 1.76(2) 2.631(3) 173(4) .
O3 H2O O1  0.863(19) 1.73(2) 2.590(3) 174(4) .
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.229
_refine_diff_density_min   -0.244
_refine_diff_density_rms    0.054
