 
data_2009src0584p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H16 N2 O2'
_chemical_formula_weight          220.27
 
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   0.0016
 '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    P21/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    19.9190(15)
_cell_length_b                    4.7488(4)
_cell_length_c                    12.3797(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  95.736(5)
_cell_angle_gamma                 90.00
_cell_volume                      1165.15(17)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     28138
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.35
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.256
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              472
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9703
_exptl_absorpt_correction_T_max   0.9983
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
 ?
;
 
_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   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             11147
_diffrn_reflns_av_R_equivalents   0.0600
_diffrn_reflns_av_sigmaI/netI     0.0665
_diffrn_reflns_limit_h_min        -25
_diffrn_reflns_limit_h_max        25
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.08
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2648
_reflns_number_gt                 1784
_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     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.0132P)²+2.5740P] 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          2648
_refine_ls_number_parameters      154
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1331
_refine_ls_R_factor_gt            0.0875
_refine_ls_wR_factor_ref          0.1707
_refine_ls_wR_factor_gt           0.1486
_refine_ls_goodness_of_fit_ref    1.096
_refine_ls_restrained_S_all       1.096
_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
C3 C -0.05860(14) 0.7067(6) 0.4368(2) 0.0227(6) Uani 1 1 d . . .
C4 C -0.10188(14) 0.4942(6) 0.3792(2) 0.0224(6) Uani 1 1 d . . .
C5 C -0.07747(15) 0.3456(6) 0.2940(2) 0.0247(6) Uani 1 1 d . . .
H5 H -0.0331 0.3819 0.2757 0.030 Uiso 1 1 calc R . .
C6 C -0.11660(14) 0.1470(6) 0.2360(2) 0.0257(7) Uani 1 1 d . . .
H6 H -0.0993 0.0482 0.1780 0.031 Uiso 1 1 calc R . .
C7 C -0.18173(15) 0.0918(6) 0.2628(2) 0.0243(7) Uani 1 1 d . . .
C8 C -0.20732(15) 0.2379(7) 0.3473(2) 0.0280(7) Uani 1 1 d . . .
H8 H -0.2518 0.2021 0.3652 0.034 Uiso 1 1 calc R . .
C9 C -0.16717(14) 0.4359(7) 0.4049(2) 0.0253(7) Uani 1 1 d . . .
H9 H -0.1844 0.5340 0.4631 0.030 Uiso 1 1 calc R . .
C12 C -0.31451(16) -0.3713(7) 0.1721(3) 0.0350(8) Uani 1 1 d . . .
C13 C -0.28943(17) -0.5072(8) 0.0738(3) 0.0388(8) Uani 1 1 d . . .
H13A H -0.2864 -0.3651 0.0171 0.058 Uiso 1 1 calc R . .
H13B H -0.3209 -0.6558 0.0467 0.058 Uiso 1 1 calc R . .
H13C H -0.2447 -0.5891 0.0937 0.058 Uiso 1 1 calc R . .
C14 C -0.38217(18) -0.4618(9) 0.2045(3) 0.0474(10) Uani 1 1 d . . .
H14 H -0.3828 -0.6724 0.2048 0.071 Uiso 1 1 calc R . .
C15 C -0.3954(2) -0.3647(10) 0.3175(3) 0.0614(13) Uani 1 1 d . . .
H15A H -0.4389 -0.4393 0.3351 0.092 Uiso 1 1 calc R . .
H15B H -0.3965 -0.1584 0.3196 0.092 Uiso 1 1 calc R . .
H15C H -0.3594 -0.4337 0.3707 0.092 Uiso 1 1 calc R . .
C16 C -0.4384(2) -0.3640(12) 0.1194(4) 0.0743(15) Uani 1 1 d . . .
H16A H -0.4397 -0.1578 0.1178 0.111 Uiso 1 1 calc R . .
H16B H -0.4818 -0.4366 0.1381 0.111 Uiso 1 1 calc R . .
H16C H -0.4296 -0.4352 0.0479 0.111 Uiso 1 1 calc R . .
N10 N -0.22020(13) -0.1050(6) 0.1999(2) 0.0293(6) Uani 1 1 d D . .
N11 N -0.28218(13) -0.1813(6) 0.2303(2) 0.0324(6) Uani 1 1 d . . .
O1 O -0.00115(9) 0.7568(4) 0.41261(15) 0.0250(5) Uani 1 1 d . . .
O2 O -0.08502(10) 0.8402(5) 0.51670(16) 0.0272(5) Uani 1 1 d . . .
H2 H -0.0582 0.9656 0.5421 0.051(12) Uiso 1 1 calc R . .
H10 H -0.1973(15) -0.207(7) 0.154(2) 0.041(10) 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
C3 0.0254(15) 0.0203(15) 0.0230(14) 0.0058(12) 0.0046(12) 0.0042(12)
C4 0.0222(14) 0.0206(15) 0.0243(13) 0.0015(12) 0.0020(11) 0.0017(12)
C5 0.0246(15) 0.0243(16) 0.0261(14) 0.0019(13) 0.0073(12) 0.0017(13)
C6 0.0269(15) 0.0242(16) 0.0270(15) -0.0003(13) 0.0071(12) -0.0007(13)
C7 0.0288(16) 0.0215(16) 0.0222(14) 0.0028(12) 0.0005(12) -0.0020(13)
C8 0.0260(15) 0.0298(17) 0.0286(15) 0.0020(14) 0.0045(12) -0.0032(14)
C9 0.0251(15) 0.0261(17) 0.0253(14) 0.0011(13) 0.0059(12) 0.0021(13)
C12 0.0321(17) 0.037(2) 0.0354(17) 0.0003(16) -0.0011(14) -0.0050(15)
C13 0.043(2) 0.036(2) 0.0365(17) -0.0061(16) -0.0001(15) -0.0069(16)
C14 0.038(2) 0.054(3) 0.051(2) -0.010(2) 0.0084(17) -0.0181(18)
C15 0.049(2) 0.075(3) 0.064(3) -0.018(2) 0.022(2) -0.024(2)
C16 0.036(2) 0.107(4) 0.079(3) -0.015(3) -0.002(2) -0.018(2)
N10 0.0281(14) 0.0313(16) 0.0288(13) -0.0046(12) 0.0051(11) -0.0038(12)
N11 0.0285(14) 0.0323(16) 0.0364(14) -0.0013(13) 0.0035(11) -0.0051(12)
O1 0.0230(10) 0.0246(11) 0.0281(10) -0.0013(9) 0.0059(8) -0.0009(9)
O2 0.0277(11) 0.0247(12) 0.0302(11) -0.0049(10) 0.0072(9) -0.0035(10)
 
_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
C3 O1 1.235(3) . ?
C3 O2 1.327(3) . ?
C3 C4 1.465(4) . ?
C4 C5 1.396(4) . ?
C4 C9 1.397(4) . ?
C5 C6 1.379(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(4) . ?
C7 N10 1.396(4) . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C12 N11 1.286(4) . ?
C12 C13 1.506(5) . ?
C12 C14 1.507(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.521(5) . ?
C14 C16 1.531(6) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N10 N11 1.375(3) . ?
N10 H10 0.901(18) . ?
O2 H2 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
O1 C3 O2 122.3(3) . . ?
O1 C3 C4 121.9(3) . . ?
O2 C3 C4 115.7(2) . . ?
C5 C4 C9 118.3(3) . . ?
C5 C4 C3 118.9(3) . . ?
C9 C4 C3 122.7(3) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 N10 122.1(3) . . ?
C6 C7 N10 117.6(3) . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C4 121.3(3) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
N11 C12 C13 124.4(3) . . ?
N11 C12 C14 117.5(3) . . ?
C13 C12 C14 118.1(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 113.6(3) . . ?
C12 C14 C16 110.0(3) . . ?
C15 C14 C16 111.0(4) . . ?
C12 C14 H14 107.3 . . ?
C15 C14 H14 107.3 . . ?
C16 C14 H14 107.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N11 N10 C7 118.8(3) . . ?
N11 N10 H10 124(2) . . ?
C7 N10 H10 115(2) . . ?
C12 N11 N10 116.4(3) . . ?
C3 O2 H2 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 H2 O1  0.84 1.82 2.660(3) 175.9 3_576
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.279
_refine_diff_density_min   -0.255
_refine_diff_density_rms    0.063
