data_dout032
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H16 N2'
_chemical_formula_weight          200.28
 
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'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/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                    7.563(3)
_cell_length_b                    5.722(2)
_cell_length_c                    25.643(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.940(6)
_cell_angle_gamma                 90.00
_cell_volume                      1109.0(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     963
_cell_measurement_theta_min       2.69
_cell_measurement_theta_max       28.29
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.41
_exptl_crystal_size_mid           0.40
_exptl_crystal_size_min           0.26
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.199
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              432
_exptl_absorpt_coefficient_mu     0.072
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9709
_exptl_absorpt_correction_T_max   0.9817
_exptl_absorpt_process_details    'SADABS (Sheldrick, 2003)'
 
_exptl_special_details
;
Data collection is performed with four batch runs at
\f = 0.00 \% (600 frames), at \f = 90.00 \%
(600 frames), at \f = 180 \% (600 frames) and
at \f = 270 \% (600 frames).
Frame width = 0.30 \& in \w. Data is
merged, corrected for decay, and treated with
multi-scan absorption corrections.
;
 
_diffrn_ambient_temperature       120(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   'Bruker AXS APEX diffractometer'
_diffrn_measurement_method        \w
_diffrn_detector_area_resol_mean  836.6
_diffrn_standards_number          0
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0
_diffrn_standards_decay_%         1
_diffrn_reflns_number             14445
_diffrn_reflns_av_R_equivalents   0.0243
_diffrn_reflns_av_sigmaI/netI     0.0172
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -34
_diffrn_reflns_limit_l_max        34
_diffrn_reflns_theta_min          1.59
_diffrn_reflns_theta_max          28.32
_reflns_number_total              2755
_reflns_number_gt                 2474
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'SMART (Bruker, 2002)'
_computing_cell_refinement        'SAINT (Bruker, 2002)'
_computing_data_reduction         SAINT
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2001)'
_computing_publication_material   'SHELXTL (Sheldrick, 2001)'
 
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0996P)^2^+0.8201P] where P=(Fo^2^+2Fc^2^)/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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2755
_refine_ls_number_parameters      163
_refine_ls_number_restraints      5
_refine_ls_R_factor_all           0.0788
_refine_ls_R_factor_gt            0.0728
_refine_ls_wR_factor_ref          0.1989
_refine_ls_wR_factor_gt           0.1924
_refine_ls_goodness_of_fit_ref    1.006
_refine_ls_restrained_S_all       1.009
_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 0.3129(2) 0.4684(3) 0.06291(7) 0.0401(4) Uani 0.7745(16) 1 d P A 1
N2 N 0.4562(3) 0.4600(3) 0.08529(9) 0.0429(5) Uani 0.7745(16) 1 d P A 1
C1 C 0.5285(3) 0.6946(5) 0.09909(12) 0.0394(6) Uani 0.7745(16) 1 d P A 1
H1A H 0.6285 0.7345 0.0768 0.047 Uiso 0.7745(16) 1 calc PR A 1
H1B H 0.5702 0.6988 0.1361 0.047 Uiso 0.7745(16) 1 calc PR A 1
C2 C 0.3748(3) 0.8645(4) 0.08961(8) 0.0306(4) Uani 0.7745(16) 1 d P A 1
H2A H 0.4142 1.0056 0.0701 0.037 Uiso 0.7745(16) 1 calc PR A 1
C3 C 0.2725(3) 0.9354(4) 0.13774(8) 0.0312(4) Uani 0.7745(16) 1 d P A 1
H3A H 0.2838 0.8144 0.1653 0.037 Uiso 0.7745(16) 1 calc PR A 1
H3B H 0.3168 1.0858 0.1521 0.037 Uiso 0.7745(16) 1 calc PR A 1
C4 C 0.0828(5) 0.9580(4) 0.11821(16) 0.0372(7) Uani 0.7745(16) 1 d PD A 1
H4A H 0.0708 1.1034 0.0967 0.045 Uiso 0.7745(16) 1 calc PR A 1
C5 C 0.0624(3) 0.7397(4) 0.08108(8) 0.0316(4) Uani 0.7745(16) 1 d P A 1
H5A H 0.0351 0.5972 0.1012 0.038 Uiso 0.7745(16) 1 calc PR A 1
H5B H -0.0329 0.7654 0.0543 0.038 Uiso 0.7745(16) 1 calc PR A 1
C6 C 0.2433(3) 0.7176(4) 0.05578(8) 0.0296(4) Uani 0.7745(16) 1 d P A 1
C7 C 0.2376(4) 0.7729(6) -0.00209(10) 0.0459(6) Uani 0.7745(16) 1 d P A 1
H7A H 0.3565 0.7572 -0.0157 0.069 Uiso 0.7745(16) 1 calc PR A 1
H7B H 0.1954 0.9332 -0.0075 0.069 Uiso 0.7745(16) 1 calc PR A 1
H7C H 0.1571 0.6639 -0.0204 0.069 Uiso 0.7745(16) 1 calc PR A 1
N1' N 0.3129(2) 0.4684(3) 0.06291(7) 0.0401(4) Uani 0.2255(16) 1 d P A 2
N2' N 0.2588(10) 0.4429(12) 0.0222(3) 0.0429(5) Uani 0.2255(16) 1 d P A 2
C1' C 0.2128(12) 0.6728(18) 0.0002(4) 0.0394(6) Uani 0.2255(16) 1 d P A 2
H1'A H 0.0892 0.6729 -0.0138 0.047 Uiso 0.2255(16) 1 calc PR A 2
H1'B H 0.2921 0.7122 -0.0285 0.047 Uiso 0.2255(16) 1 calc PR A 2
C2' C 0.2347(9) 0.8483(14) 0.0441(3) 0.0306(4) Uani 0.2255(16) 1 d P A 2
H2'A H 0.2974 0.9932 0.0332 0.037 Uiso 0.2255(16) 1 calc PR A 2
C3' C 0.0619(9) 0.9027(14) 0.0726(3) 0.0312(4) Uani 0.2255(16) 1 d P A 2
H3'A H 0.0121 1.0549 0.0611 0.037 Uiso 0.2255(16) 1 calc PR A 2
H3'B H -0.0276 0.7793 0.0657 0.037 Uiso 0.2255(16) 1 calc PR A 2
C4' C 0.109(2) 0.909(2) 0.1225(6) 0.0372(7) Uani 0.2255(16) 1 d PD A 2
H4'A H 0.1777 1.0584 0.1248 0.045 Uiso 0.2255(16) 1 calc PR A 2
C5' C 0.2519(9) 0.7287(13) 0.1372(3) 0.0316(4) Uani 0.2255(16) 1 d P A 2
H5'A H 0.1998 0.5785 0.1482 0.038 Uiso 0.2255(16) 1 calc PR A 2
H5'B H 0.3343 0.7871 0.1651 0.038 Uiso 0.2255(16) 1 calc PR A 2
C6' C 0.3432(10) 0.7065(12) 0.0845(3) 0.0296(4) Uani 0.2255(16) 1 d P A 2
C7' C 0.5338(17) 0.769(2) 0.0870(4) 0.0459(6) Uani 0.2255(16) 1 d P A 2
H7'A H 0.5836 0.7479 0.0525 0.069 Uiso 0.2255(16) 1 calc PR A 2
H7'B H 0.5963 0.6671 0.1123 0.069 Uiso 0.2255(16) 1 calc PR A 2
H7'C H 0.5474 0.9320 0.0979 0.069 Uiso 0.2255(16) 1 calc PR A 2
C8 C -0.1691(3) 1.1484(3) 0.15745(7) 0.0420(4) Uani 1 1 d D A .
H8A H -0.1565 1.2647 0.1314 0.050 Uiso 1 1 calc R . .
C9 C -0.3028(2) 1.1688(3) 0.19225(8) 0.0412(4) Uani 1 1 d D . .
H9A H -0.3809 1.2987 0.1899 0.049 Uiso 1 1 calc R . .
C10 C -0.3245(2) 1.0033(4) 0.23036(7) 0.0392(4) Uani 1 1 d D . .
H10A H -0.4170 1.0182 0.2543 0.047 Uiso 1 1 calc R . .
C11 C -0.2101(3) 0.8146(4) 0.23351(7) 0.0416(4) Uani 1 1 d D . .
H11A H -0.2238 0.6991 0.2597 0.050 Uiso 1 1 calc R . .
C12 C -0.0745(2) 0.7942(3) 0.19818(8) 0.0412(4) Uani 1 1 d D A .
H12A H 0.0039 0.6646 0.2004 0.049 Uiso 1 1 calc R . .
C13 C -0.0535(2) 0.9629(3) 0.15961(7) 0.0385(4) Uani 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
N1 0.0441(9) 0.0240(7) 0.0529(9) -0.0010(6) 0.0142(7) 0.0000(6)
N2 0.0423(10) 0.0298(9) 0.0570(12) 0.0008(8) 0.0090(9) 0.0068(8)
C1 0.0278(10) 0.0364(13) 0.0539(16) -0.0036(10) 0.0012(10) 0.0068(10)
C2 0.0282(9) 0.0242(9) 0.0401(10) -0.0016(7) 0.0091(8) -0.0008(7)
C3 0.0260(9) 0.0339(10) 0.0337(9) -0.0046(8) 0.0038(7) -0.0005(7)
C4 0.0434(16) 0.0171(14) 0.0525(13) -0.0002(12) 0.0215(10) 0.0024(11)
C5 0.0272(9) 0.0367(11) 0.0309(9) -0.0032(8) 0.0012(7) -0.0019(8)
C6 0.0330(10) 0.0251(9) 0.0309(9) -0.0006(7) 0.0057(7) 0.0005(7)
C7 0.0583(16) 0.0490(15) 0.0309(11) 0.0036(11) 0.0099(10) 0.0010(13)
N1' 0.0441(9) 0.0240(7) 0.0529(9) -0.0010(6) 0.0142(7) 0.0000(6)
N2' 0.0423(10) 0.0298(9) 0.0570(12) 0.0008(8) 0.0090(9) 0.0068(8)
C1' 0.0278(10) 0.0364(13) 0.0539(16) -0.0036(10) 0.0012(10) 0.0068(10)
C2' 0.0282(9) 0.0242(9) 0.0401(10) -0.0016(7) 0.0091(8) -0.0008(7)
C3' 0.0260(9) 0.0339(10) 0.0337(9) -0.0046(8) 0.0038(7) -0.0005(7)
C4' 0.0434(16) 0.0171(14) 0.0525(13) -0.0002(12) 0.0215(10) 0.0024(11)
C5' 0.0272(9) 0.0367(11) 0.0309(9) -0.0032(8) 0.0012(7) -0.0019(8)
C6' 0.0330(10) 0.0251(9) 0.0309(9) -0.0006(7) 0.0057(7) 0.0005(7)
C7' 0.0583(16) 0.0490(15) 0.0309(11) 0.0036(11) 0.0099(10) 0.0010(13)
C8 0.0498(10) 0.0364(9) 0.0405(9) -0.0009(7) 0.0132(8) -0.0106(8)
C9 0.0395(9) 0.0358(9) 0.0487(10) -0.0042(7) 0.0064(8) 0.0012(7)
C10 0.0306(8) 0.0531(11) 0.0343(8) -0.0078(7) 0.0099(6) -0.0081(7)
C11 0.0420(9) 0.0477(10) 0.0351(9) 0.0081(7) -0.0007(7) -0.0098(8)
C12 0.0320(8) 0.0408(9) 0.0506(10) -0.0054(8) -0.0008(7) 0.0019(7)
C13 0.0345(8) 0.0421(10) 0.0396(9) -0.0121(7) 0.0120(7) -0.0112(7)
 
_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 N2 1.210(3) . ?
N1 C6 1.529(3) . ?
N2 C1 1.488(3) . ?
C1 C2 1.528(3) . ?
C2 C3 1.533(3) . ?
C2 C6 1.546(3) . ?
C3 C4 1.509(4) . ?
C4 C13 1.505(5) . ?
C4 C5 1.575(3) . ?
C5 C6 1.539(3) . ?
C6 C7 1.516(3) . ?
N2' C1' 1.469(12) . ?
C1' C2' 1.515(12) . ?
C2' C6' 1.531(11) . ?
C2' C3' 1.550(9) . ?
C3' C4' 1.316(16) . ?
C4' C5' 1.530(15) . ?
C4' C13 1.612(19) . ?
C5' C6' 1.544(10) . ?
C6' C7' 1.484(15) . ?
C8 C13 1.375(3) . ?
C8 C9 1.376(3) . ?
C9 C10 1.375(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.396(3) . ?
C12 C13 1.395(3) . ?
 
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
N2 N1 C6 113.12(16) . . ?
N1 N2 C1 113.15(18) . . ?
N2 C1 C2 105.36(19) . . ?
C1 C2 C3 116.2(2) . . ?
C1 C2 C6 102.39(18) . . ?
C3 C2 C6 105.23(16) . . ?
C4 C3 C2 104.8(2) . . ?
C13 C4 C3 115.7(3) . . ?
C13 C4 C5 112.7(2) . . ?
C3 C4 C5 101.8(2) . . ?
C6 C5 C4 104.4(2) . . ?
N1 C6 C7 108.05(19) . . ?
N1 C6 C5 109.46(16) . . ?
C7 C6 C5 113.51(19) . . ?
N1 C6 C2 103.18(16) . . ?
C7 C6 C2 115.6(2) . . ?
C5 C6 C2 106.45(16) . . ?
N2' C1' C2' 106.8(8) . . ?
C1' C2' C6' 101.2(7) . . ?
C1' C2' C3' 114.3(6) . . ?
C6' C2' C3' 103.2(6) . . ?
C4' C3' C2' 104.9(9) . . ?
C3' C4' C5' 112.8(11) . . ?
C3' C4' C13 113.0(9) . . ?
C5' C4' C13 122.0(12) . . ?
C4' C5' C6' 99.9(9) . . ?
C7' C6' C2' 113.6(7) . . ?
C7' C6' C5' 113.8(7) . . ?
C2' C6' C5' 107.6(6) . . ?
C13 C8 C9 121.32(18) . . ?
C10 C9 C8 120.69(18) . . ?
C9 C10 C11 119.33(16) . . ?
C10 C11 C12 119.89(17) . . ?
C13 C12 C11 120.42(17) . . ?
C8 C13 C12 118.35(16) . . ?
C8 C13 C4 115.85(18) . . ?
C12 C13 C4 125.77(19) . . ?
C8 C13 C4' 128.4(5) . . ?
C12 C13 C4' 113.2(5) . . ?
C4 C13 C4' 12.7(6) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C6 N1 N2 C1 -1.1(3) . . . . ?
N1 N2 C1 C2 11.5(3) . . . . ?
N2 C1 C2 C3 98.1(2) . . . . ?
N2 C1 C2 C6 -16.0(2) . . . . ?
C1 C2 C3 C4 -144.2(2) . . . . ?
C6 C2 C3 C4 -31.8(2) . . . . ?
C2 C3 C4 C13 164.24(17) . . . . ?
C2 C3 C4 C5 41.7(3) . . . . ?
C13 C4 C5 C6 -160.57(19) . . . . ?
C3 C4 C5 C6 -36.0(3) . . . . ?
N2 N1 C6 C7 113.3(2) . . . . ?
N2 N1 C6 C5 -122.6(2) . . . . ?
N2 N1 C6 C2 -9.6(2) . . . . ?
C4 C5 C6 N1 127.7(2) . . . . ?
C4 C5 C6 C7 -111.5(2) . . . . ?
C4 C5 C6 C2 16.8(2) . . . . ?
C1 C2 C6 N1 15.1(2) . . . . ?
C3 C2 C6 N1 -106.80(17) . . . . ?
C1 C2 C6 C7 -102.6(2) . . . . ?
C3 C2 C6 C7 135.5(2) . . . . ?
C1 C2 C6 C5 130.3(2) . . . . ?
C3 C2 C6 C5 8.4(2) . . . . ?
N2' C1' C2' C6' 15.5(8) . . . . ?
N2' C1' C2' C3' -94.8(8) . . . . ?
C1' C2' C3' C4' 138.0(9) . . . . ?
C6' C2' C3' C4' 29.0(9) . . . . ?
C2' C3' C4' C5' -36.4(12) . . . . ?
C2' C3' C4' C13 -179.8(7) . . . . ?
C3' C4' C5' C6' 27.7(12) . . . . ?
C13 C4' C5' C6' 167.3(6) . . . . ?
C1' C2' C6' C7' 102.6(8) . . . . ?
C3' C2' C6' C7' -138.9(7) . . . . ?
C1' C2' C6' C5' -130.5(7) . . . . ?
C3' C2' C6' C5' -12.0(7) . . . . ?
C4' C5' C6' C7' 120.3(8) . . . . ?
C4' C5' C6' C2' -6.5(8) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C9 C8 C13 C12 0.0(3) . . . . ?
C9 C8 C13 C4 178.15(19) . . . . ?
C9 C8 C13 C4' 179.8(4) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C11 C12 C13 C4 -177.91(19) . . . . ?
C11 C12 C13 C4' -179.8(3) . . . . ?
C3 C4 C13 C8 126.9(2) . . . . ?
C5 C4 C13 C8 -116.5(2) . . . . ?
C3 C4 C13 C12 -55.1(3) . . . . ?
C5 C4 C13 C12 61.5(3) . . . . ?
C3 C4 C13 C4' -47.3(15) . . . . ?
C5 C4 C13 C4' 69.3(15) . . . . ?
C3' C4' C13 C8 -55.0(10) . . . . ?
C5' C4' C13 C8 165.4(5) . . . . ?
C3' C4' C13 C12 124.7(8) . . . . ?
C5' C4' C13 C12 -14.9(8) . . . . ?
C3' C4' C13 C4 -48.4(14) . . . . ?
C5' C4' C13 C4 172(2) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.790
_refine_diff_density_min   -0.547
_refine_diff_density_rms    0.055