data_s94
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. P. J. Murphy
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C12 H18 N2 O2, H2 O'
_chemical_formula_sum
 'C12 H20 N2 O3'
_chemical_formula_weight          240.30
_chemical_absolute_configuration  unk 

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            Orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
_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+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 
_cell_length_a                    4.7254(3)
_cell_length_b                    9.6175(7)
_cell_length_c                    27.407(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1245.55(16)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2225
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Slab
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.36
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.281
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              520
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9676
_exptl_absorpt_correction_T_max   0.9963
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
_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.
;
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             8940
_diffrn_reflns_av_R_equivalents   0.2385
_diffrn_reflns_av_sigmaI/netI     0.1808
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -35
_diffrn_reflns_limit_l_max        32
_diffrn_reflns_theta_min          3.08
_diffrn_reflns_theta_max          27.42
_reflns_number_total              2609
_reflns_number_gt                 1722
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0858P)²+0.8981P] 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        0.046(12)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2609
_refine_ls_number_parameters      161
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.1314
_refine_ls_R_factor_gt            0.0859
_refine_ls_wR_factor_ref          0.2348
_refine_ls_wR_factor_gt           0.2001
_refine_ls_goodness_of_fit_ref    1.059
_refine_ls_restrained_S_all       1.059
_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 0.2538(10) 0.2611(5) 0.87182(17) 0.0320(10) Uani 1 1 d . . .
H1 H 0.4642 0.2499 0.8728 0.038 Uiso 1 1 calc R . .
C2 C 0.1731(17) 0.4161(5) 0.8673(2) 0.0597(17) Uani 1 1 d . . .
H2A H 0.3455 0.4731 0.8627 0.072 Uiso 1 1 calc R . .
H2B H 0.0483 0.4301 0.8387 0.072 Uiso 1 1 calc R . .
C3 C 0.034(2) 0.4558(7) 0.9097(4) 0.121(4) Uani 1 1 d . . .
H3A H -0.1437 0.5044 0.9009 0.146 Uiso 1 1 calc R . .
H3B H 0.1543 0.5220 0.9280 0.146 Uiso 1 1 calc R . .
C4 C -0.0336(9) 0.3367(5) 0.94136(16) 0.0328(10) Uani 1 1 d . . .
H4A H 0.0278 0.3539 0.9754 0.039 Uiso 1 1 calc R . .
H4B H -0.2390 0.3164 0.9411 0.039 Uiso 1 1 calc R . .
C5 C 0.1440(9) 0.0963(5) 0.94091(15) 0.0280(9) Uani 1 1 d . . .
C6 C 0.3333(9) -0.0133(5) 0.91763(16) 0.0315(10) Uani 1 1 d . . .
H6A H 0.4498 -0.0584 0.9431 0.038 Uiso 1 1 calc R . .
H6B H 0.4624 0.0316 0.8940 0.038 Uiso 1 1 calc R . .
C7 C 0.1526(10) -0.1239(5) 0.89130(16) 0.0348(10) Uani 1 1 d . . .
H7A H 0.0725 -0.1894 0.9155 0.042 Uiso 1 1 calc R . .
H7B H -0.0063 -0.0783 0.8741 0.042 Uiso 1 1 calc R . .
C8 C 0.3315(11) -0.2023(5) 0.85531(19) 0.0398(11) Uani 1 1 d . . .
H8 H 0.4744 -0.2613 0.8682 0.048 Uiso 1 1 calc R . .
C9 C 0.3077(10) -0.1965(5) 0.80715(19) 0.0404(12) Uani 1 1 d . . .
H9 H 0.4372 -0.2510 0.7888 0.049 Uiso 1 1 calc R . .
C10 C 0.0961(11) -0.1122(5) 0.77858(17) 0.0411(12) Uani 1 1 d . . .
H10A H -0.0702 -0.0931 0.7995 0.049 Uiso 1 1 calc R . .
H10B H 0.0307 -0.1674 0.7503 0.049 Uiso 1 1 calc R . .
C11 C 0.2172(10) 0.0259(5) 0.76028(17) 0.0377(11) Uani 1 1 d . . .
H11A H 0.3802 0.0067 0.7386 0.045 Uiso 1 1 calc R . .
H11B H 0.0712 0.0744 0.7407 0.045 Uiso 1 1 calc R . .
C12 C 0.1287(8) 0.1773(5) 0.83036(15) 0.0302(10) Uani 1 1 d . . .
N1 N 0.1285(8) 0.2231(4) 0.91914(12) 0.0282(8) Uani 1 1 d . . .
N2 N 0.3092(7) 0.1173(4) 0.79979(13) 0.0297(9) Uani 1 1 d . . .
H2 H 0.4913 0.1332 0.8035 0.036 Uiso 1 1 calc R . .
O1 O 0.0099(7) 0.0718(3) 0.97851(11) 0.0353(8) Uani 1 1 d . . .
O2 O -0.1315(6) 0.1675(4) 0.82602(12) 0.0486(10) Uani 1 1 d . . .
O1W O 0.0429(8) -0.1919(4) 1.01995(15) 0.0475(10) Uani 1 1 d D . .
H1WA H 0.019(11) -0.110(3) 1.010(2) 0.057 Uiso 1 1 d D . .
H1WB H 0.202(7) -0.219(5) 1.009(2) 0.057 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
C1 0.036(2) 0.034(2) 0.027(2) -0.0004(19) 0.0008(18) 0.0031(19)
C2 0.108(5) 0.032(3) 0.039(3) 0.010(2) 0.027(3) 0.014(3)
C3 0.200(10) 0.040(4) 0.124(8) 0.024(4) 0.117(8) 0.040(5)
C4 0.030(2) 0.040(2) 0.028(2) -0.011(2) 0.0034(19) 0.003(2)
C5 0.031(2) 0.034(2) 0.0182(19) -0.0010(17) -0.0057(18) 0.0017(19)
C6 0.033(2) 0.035(2) 0.027(2) 0.0041(19) -0.0029(18) 0.003(2)
C7 0.038(2) 0.041(3) 0.025(2) -0.0017(19) 0.0046(19) -0.004(2)
C8 0.044(3) 0.032(2) 0.043(3) -0.004(2) 0.006(2) -0.005(2)
C9 0.045(3) 0.037(3) 0.040(3) -0.011(2) 0.010(2) -0.007(2)
C10 0.051(3) 0.050(3) 0.023(2) -0.002(2) -0.002(2) -0.020(2)
C11 0.044(3) 0.046(3) 0.023(2) -0.002(2) -0.0008(18) -0.010(2)
C12 0.0224(18) 0.050(3) 0.018(2) 0.006(2) 0.0015(17) 0.002(2)
N1 0.0331(18) 0.0323(19) 0.0192(17) 0.0006(15) 0.0018(15) 0.0040(16)
N2 0.0225(17) 0.041(2) 0.0253(19) -0.0025(16) 0.0001(14) -0.0067(16)
O1 0.0431(17) 0.0410(18) 0.0218(16) 0.0009(14) 0.0025(14) -0.0017(15)
O2 0.0241(15) 0.091(3) 0.0304(18) -0.0007(19) -0.0012(14) 0.0003(17)
O1W 0.045(2) 0.050(2) 0.048(2) 0.0127(19) 0.0050(17) -0.0014(17)
 
_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 N1 1.472(6) . ?
C1 C12 1.513(6) . ?
C1 C2 1.544(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.390(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.472(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.467(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O1 1.233(5) . ?
C5 N1 1.360(5) . ?
C5 C6 1.522(6) . ?
C6 C7 1.543(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.502(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.326(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.507(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.531(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N2 1.461(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O2 1.239(5) . ?
C12 N2 1.327(5) . ?
N2 H2 0.8800 . ?
O1W H1WA 0.842(19) . ?
O1W H1WB 0.853(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
N1 C1 C12 111.9(3) . . ?
N1 C1 C2 102.2(4) . . ?
C12 C1 C2 110.9(4) . . ?
N1 C1 H1 110.5 . . ?
C12 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
C3 C2 C1 108.3(5) . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
C2 C3 C4 112.5(5) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C3 102.8(4) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
O1 C5 N1 120.7(4) . . ?
O1 C5 C6 121.3(4) . . ?
N1 C5 C6 118.0(4) . . ?
C5 C6 C7 110.4(3) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 110.0(4) . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 125.8(5) . . ?
C9 C8 H8 117.1 . . ?
C7 C8 H8 117.1 . . ?
C8 C9 C10 126.6(5) . . ?
C8 C9 H9 116.7 . . ?
C10 C9 H9 116.7 . . ?
C9 C10 C11 112.9(4) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C10 113.0(4) . . ?
N2 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
N2 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O2 C12 N2 123.0(4) . . ?
O2 C12 C1 120.0(4) . . ?
N2 C12 C1 117.0(4) . . ?
C5 N1 C4 120.9(3) . . ?
C5 N1 C1 126.0(4) . . ?
C4 N1 C1 113.0(3) . . ?
C12 N2 C11 122.5(3) . . ?
C12 N2 H2 118.7 . . ?
C11 N2 H2 118.7 . . ?
H1WA O1W H1WB 106(4) . . ?
 
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
N2 H2 O2  0.88 1.92 2.781(4) 167.8 1_655
O1W H1WA O1  0.842(19) 1.95(2) 2.783(5) 171(5) .
O1W H1WB O1W  0.853(19) 1.99(2) 2.833(5) 172(5) 3_547
 
_diffrn_measured_fraction_theta_max    0.963
_diffrn_reflns_theta_full              27.42
_diffrn_measured_fraction_theta_full   0.963
_refine_diff_density_max    0.344
_refine_diff_density_min   -0.377
_refine_diff_density_rms    0.081
