data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Paddy Murphy
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C22 H32 N4 O4'
_chemical_formula_sum
 'C22 H32 N4 O4'
_chemical_formula_weight          416.52
_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            Monoclinic
_symmetry_space_group_name_H-M    C2
_symmetry_space_group_name_hall  C2y
 
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                    16.7084(12)
_cell_length_b                    6.9925(5)
_cell_length_c                    11.3651(8)
_cell_angle_alpha                 90.000
_cell_angle_beta                  123.721(3)
_cell_angle_gamma                 90.000
_cell_volume                      1104.42(14)
_cell_formula_units_Z             2
_cell_measurement_temperature     153(2)
_cell_measurement_reflns_used     5159
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.253
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              448
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.9568
_exptl_absorpt_correction_T_max   0.9983
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
?
;
 
_diffrn_ambient_temperature       153(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method        'φ and ω scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  '9.091 pixels mm^1^'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             5510
_diffrn_reflns_av_R_equivalents   0.0419
_diffrn_reflns_av_sigmaI/netI     0.0413
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.93
_diffrn_reflns_theta_max          25.02
_reflns_number_total              1944
_reflns_number_gt                 1772
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO (Otwinowski and MInor, 1997)'
_computing_data_reduction         'DENZO, COLLECT, MAXUS (Mackay et al., 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0702P)²+1.1620P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.008(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1944
_refine_ls_number_parameters      138
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0512
_refine_ls_R_factor_gt            0.0444
_refine_ls_wR_factor_ref          0.1194
_refine_ls_wR_factor_gt           0.1140
_refine_ls_goodness_of_fit_ref    0.954
_refine_ls_restrained_S_all       0.953
_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
O1 O 0.65642(12) 0.1637(3) 0.13309(17) 0.0280(5) Uani 1 1 d . . .
O2 O 0.59471(12) 0.4440(3) 0.31838(17) 0.0329(5) Uani 1 1 d . . .
N2 N 0.45676(13) 0.4174(3) 0.10040(19) 0.0214(5) Uani 1 1 d . . .
H2 H 0.4154 0.3403 0.0363 0.026 Uiso 1 1 calc R . .
N1 N 0.63944(14) 0.0608(3) 0.30540(19) 0.0229(5) Uani 1 1 d . . .
C7 C 0.53935(16) 0.1262(4) 0.2269(2) 0.0231(6) Uani 1 1 d . . .
H7 H 0.5025 0.0708 0.1316 0.028 Uiso 1 1 calc R . .
C9 C 0.44179(17) 0.6140(3) 0.0785(3) 0.0227(6) Uani 1 1 d . . .
H9 H 0.4940 0.6941 0.1351 0.027 Uiso 1 1 calc R . .
C8 C 0.53466(16) 0.3444(4) 0.2197(2) 0.0223(5) Uani 1 1 d . . .
C3 C 0.69259(17) 0.0905(3) 0.2518(2) 0.0227(5) Uani 1 1 d . . .
C10 C 0.35827(17) 0.6952(4) -0.0174(3) 0.0282(6) Uani 1 1 d . . .
H10 H 0.3578 0.8274 -0.0266 0.034 Uiso 1 1 calc R . .
C4 C 0.66852(19) -0.0332(4) 0.4396(3) 0.0314(7) Uani 1 1 d . . .
H4A H 0.7300 0.0153 0.5172 0.038 Uiso 1 1 calc R . .
H4B H 0.6731 -0.1706 0.4333 0.038 Uiso 1 1 calc R . .
C6 C 0.50255(18) 0.0502(4) 0.3160(3) 0.0305(6) Uani 1 1 d . . .
H6A H 0.4609 0.1432 0.3197 0.037 Uiso 1 1 calc R . .
H6B H 0.4670 -0.0680 0.2764 0.037 Uiso 1 1 calc R . .
C2 C 0.79533(18) 0.0336(4) 0.3394(3) 0.0268(6) Uani 1 1 d . . .
H2A H 0.8209 -0.0187 0.4287 0.032 Uiso 1 1 calc R . .
C11 C 0.2653(2) 0.5930(5) -0.1114(3) 0.0489(8) Uani 1 1 d . . .
H11A H 0.2488 0.5954 -0.2069 0.073 Uiso 1 1 calc R . .
H11B H 0.2157 0.6550 -0.1073 0.073 Uiso 1 1 calc R . .
H11C H 0.2716 0.4628 -0.0806 0.073 Uiso 1 1 calc R . .
C1 C 0.85090(19) 0.0568(4) 0.2912(3) 0.0350(7) Uani 1 1 d . . .
H1A H 0.8255 0.1091 0.2019 0.042 Uiso 1 1 calc R . .
H1B H 0.9153 0.0209 0.3466 0.042 Uiso 1 1 calc R . .
C5 C 0.5901(2) 0.0174(6) 0.4584(3) 0.0518(10) Uani 1 1 d . . .
H5A H 0.5796 -0.0858 0.5054 0.062 Uiso 1 1 calc R . .
H5B H 0.6068 0.1320 0.5156 0.062 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
O1 0.0303(9) 0.0323(10) 0.0176(9) 0.0058(8) 0.0109(7) 0.0041(8)
O2 0.0262(9) 0.0327(10) 0.0224(9) -0.0074(8) 0.0026(8) -0.0004(8)
N2 0.0181(10) 0.0230(11) 0.0151(9) -0.0019(9) 0.0041(8) -0.0003(8)
N1 0.0208(10) 0.0275(11) 0.0163(10) 0.0040(9) 0.0078(9) 0.0049(9)
C7 0.0187(11) 0.0255(13) 0.0185(11) 0.0006(10) 0.0063(10) 0.0039(10)
C9 0.0250(12) 0.0213(13) 0.0223(11) -0.0010(10) 0.0134(10) -0.0011(10)
C8 0.0188(12) 0.0282(13) 0.0159(12) -0.0018(10) 0.0072(11) 0.0006(10)
C3 0.0261(12) 0.0187(12) 0.0184(12) 0.0004(10) 0.0093(10) 0.0025(10)
C10 0.0295(14) 0.0257(14) 0.0244(13) 0.0033(11) 0.0119(11) 0.0046(11)
C4 0.0279(13) 0.0417(17) 0.0222(12) 0.0119(12) 0.0124(11) 0.0070(12)
C6 0.0257(13) 0.0306(15) 0.0357(14) 0.0029(12) 0.0175(12) 0.0018(12)
C2 0.0266(13) 0.0295(14) 0.0209(12) 0.0041(11) 0.0111(11) 0.0075(11)
C11 0.0316(15) 0.0370(17) 0.0452(17) 0.0027(14) 0.0008(14) 0.0078(13)
C1 0.0302(14) 0.0428(17) 0.0339(15) 0.0071(13) 0.0189(12) 0.0080(13)
C5 0.0356(16) 0.084(3) 0.0383(16) 0.0265(18) 0.0222(14) 0.0111(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
O1 C3 1.242(3) . ?
O2 C8 1.225(3) . ?
N2 C8 1.354(3) . ?
N2 C9 1.395(4) . ?
N1 C3 1.343(3) . ?
N1 C7 1.465(3) . ?
N1 C4 1.474(3) . ?
C7 C8 1.527(4) . ?
C7 C6 1.542(4) . ?
C9 C10 1.330(3) . ?
C3 C2 1.483(3) . ?
C10 C11 1.490(4) . ?
C4 C5 1.482(4) . ?
C6 C5 1.478(4) . ?
C2 C1 1.324(4) . ?
 
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
C8 N2 C9 121.8(2) . . ?
C3 N1 C7 119.60(19) . . ?
C3 N1 C4 128.13(19) . . ?
C7 N1 C4 112.27(19) . . ?
N1 C7 C8 110.6(2) . . ?
N1 C7 C6 103.22(19) . . ?
C8 C7 C6 110.6(2) . . ?
C10 C9 N2 124.7(2) . . ?
O2 C8 N2 123.1(2) . . ?
O2 C8 C7 121.8(2) . . ?
N2 C8 C7 115.0(2) . . ?
O1 C3 N1 120.7(2) . . ?
O1 C3 C2 121.6(2) . . ?
N1 C3 C2 117.7(2) . . ?
C9 C10 C11 125.8(3) . . ?
N1 C4 C5 103.5(2) . . ?
C5 C6 C7 105.0(2) . . ?
C1 C2 C3 120.4(2) . . ?
C6 C5 C4 107.2(2) . . ?
 
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 O1  0.86 2.03 2.862(3) 163.7 2_655
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.532
_refine_diff_density_min   -0.321
_refine_diff_density_rms    0.042
