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# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_chem260

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 N2'
_chemical_formula_weight         252.35

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)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5299(3)
_cell_length_b                   6.0689(2)
_cell_length_c                   13.7293(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.554(2)
_cell_angle_gamma                90.00
_cell_volume                     710.46(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5079
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.86

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12394
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         28.29
_reflns_number_total             3410
_reflns_number_gt                2859
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.1144P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(2)
_refine_ls_number_reflns         3410
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   0.641
_refine_ls_restrained_S_all      0.641
_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
C10 C -0.03146(14) 0.5850(2) 0.69500(9) 0.0230(3) Uani 1 1 d . . .
C13 C -0.22466(16) 0.6708(2) 0.52799(9) 0.0247(3) Uani 1 1 d . . .
C11 C -0.09894(16) 0.7915(2) 0.67916(10) 0.0263(3) Uani 1 1 d . . .
H11 H -0.0789 0.9056 0.7252 0.032 Uiso 1 1 calc R . .
C15 C -0.05943(15) 0.4228(2) 0.62445(9) 0.0248(3) Uani 1 1 d . . .
H15 H -0.0132 0.2815 0.6330 0.030 Uiso 1 1 calc R . .
C9 C 0.06061(15) 0.5421(2) 0.78416(9) 0.0237(3) Uani 1 1 d . . .
H9 H 0.0828 0.6624 0.8266 0.028 Uiso 1 1 calc R . .
C14 C -0.15260(16) 0.4632(2) 0.54275(10) 0.0260(3) Uani 1 1 d . . .
H14 H -0.1686 0.3499 0.4957 0.031 Uiso 1 1 calc R . .
C6 C 0.37262(15) 0.2952(2) 0.88076(9) 0.0226(3) Uani 1 1 d . . .
C16 C -0.37237(18) 0.9317(3) 0.42487(11) 0.0339(3) Uani 1 1 d . . .
H16A H -0.4171 0.9997 0.4826 0.051 Uiso 1 1 calc R . .
H16B H -0.4518 0.9273 0.3720 0.051 Uiso 1 1 calc R . .
H16C H -0.2822 1.0184 0.4042 0.051 Uiso 1 1 calc R . .
C7 C 0.20087(15) 0.3360(2) 0.90179(9) 0.0237(3) Uani 1 1 d . . .
H7 H 0.1922 0.4796 0.9370 0.028 Uiso 1 1 calc R . .
C4 C 0.61225(16) 0.4342(3) 0.81296(10) 0.0316(3) Uani 1 1 d . . .
H4 H 0.6677 0.5504 0.7829 0.038 Uiso 1 1 calc R . .
C5 C 0.45679(15) 0.4632(2) 0.83703(9) 0.0270(3) Uani 1 1 d . . .
H5 H 0.4068 0.6000 0.8234 0.032 Uiso 1 1 calc R . .
C12 C -0.19402(16) 0.8351(2) 0.59853(10) 0.0275(3) Uani 1 1 d . . .
H12 H -0.2393 0.9772 0.5905 0.033 Uiso 1 1 calc R . .
C1 C 0.44882(16) 0.0979(2) 0.90156(10) 0.0289(3) Uani 1 1 d . . .
H1 H 0.3940 -0.0179 0.9324 0.035 Uiso 1 1 calc R . .
C8 C 0.12426(17) 0.1584(3) 0.96194(10) 0.0319(3) Uani 1 1 d . . .
H8A H 0.0149 0.1985 0.9729 0.048 Uiso 1 1 calc R . .
H8B H 0.1807 0.1441 1.0248 0.048 Uiso 1 1 calc R . .
H8C H 0.1277 0.0177 0.9270 0.048 Uiso 1 1 calc R . .
C17 C -0.33857(18) 0.5453(3) 0.37160(10) 0.0350(3) Uani 1 1 d . . .
H17A H -0.2368 0.5213 0.3418 0.053 Uiso 1 1 calc R . .
H17B H -0.4144 0.5978 0.3220 0.053 Uiso 1 1 calc R . .
H17C H -0.3758 0.4065 0.3992 0.053 Uiso 1 1 calc R . .
C3 C 0.68653(17) 0.2359(3) 0.83285(11) 0.0332(3) Uani 1 1 d . . .
H3 H 0.7928 0.2150 0.8159 0.040 Uiso 1 1 calc R . .
C2 C 0.60535(17) 0.0684(3) 0.87745(10) 0.0349(4) Uani 1 1 d . . .
H2 H 0.6563 -0.0674 0.8918 0.042 Uiso 1 1 calc R . .
N1 N 0.11291(12) 0.3528(2) 0.80826(8) 0.0242(2) Uani 1 1 d . . .
N2 N -0.32180(14) 0.7085(2) 0.44828(9) 0.0308(3) Uani 1 1 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
C10 0.0200(6) 0.0262(7) 0.0230(6) 0.0016(5) 0.0030(5) -0.0005(5)
C13 0.0227(6) 0.0263(7) 0.0252(6) 0.0044(5) 0.0008(5) -0.0030(5)
C11 0.0279(7) 0.0252(7) 0.0260(7) -0.0020(5) 0.0030(5) -0.0015(6)
C15 0.0233(6) 0.0240(6) 0.0272(6) 0.0001(5) 0.0007(5) 0.0016(5)
C9 0.0210(6) 0.0271(7) 0.0230(6) -0.0033(5) 0.0028(5) -0.0009(5)
C14 0.0278(7) 0.0257(7) 0.0245(6) -0.0008(5) -0.0014(5) -0.0014(6)
C6 0.0229(6) 0.0274(6) 0.0174(6) -0.0023(5) -0.0035(5) -0.0018(5)
C16 0.0372(8) 0.0346(8) 0.0298(7) 0.0061(6) -0.0018(6) 0.0094(7)
C7 0.0236(6) 0.0267(6) 0.0209(6) -0.0018(5) -0.0004(5) 0.0002(5)
C4 0.0268(7) 0.0362(8) 0.0319(7) -0.0036(7) 0.0020(6) -0.0077(6)
C5 0.0267(7) 0.0264(7) 0.0278(7) -0.0011(6) -0.0014(5) -0.0003(6)
C12 0.0292(7) 0.0233(7) 0.0299(7) 0.0035(6) 0.0026(5) 0.0025(6)
C1 0.0314(7) 0.0292(7) 0.0257(7) 0.0017(6) -0.0042(5) 0.0007(6)
C8 0.0292(7) 0.0371(8) 0.0295(7) 0.0023(6) 0.0021(5) -0.0056(6)
C17 0.0392(8) 0.0370(8) 0.0284(7) 0.0025(6) -0.0073(6) -0.0021(7)
C3 0.0234(7) 0.0448(9) 0.0314(7) -0.0084(6) -0.0011(6) 0.0035(6)
C2 0.0321(7) 0.0380(9) 0.0342(8) -0.0026(7) -0.0057(6) 0.0111(7)
N1 0.0216(5) 0.0289(6) 0.0222(5) -0.0019(5) -0.0008(4) -0.0004(5)
N2 0.0356(7) 0.0275(6) 0.0288(6) 0.0062(5) -0.0068(5) -0.0022(5)

_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
C10 C11 1.3938(19) . ?
C10 C15 1.3970(18) . ?
C10 C9 1.4597(17) . ?
C13 N2 1.3737(16) . ?
C13 C12 1.4093(19) . ?
C13 C14 1.4144(19) . ?
C11 C12 1.3800(19) . ?
C11 H11 0.9500 . ?
C15 C14 1.3789(18) . ?
C15 H15 0.9500 . ?
C9 N1 1.2729(17) . ?
C9 H9 0.9500 . ?
C14 H14 0.9500 . ?
C6 C1 1.3885(19) . ?
C6 C5 1.3922(19) . ?
C6 C7 1.5211(17) . ?
C16 N2 1.455(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C7 N1 1.4732(15) . ?
C7 C8 1.5168(19) . ?
C7 H7 1.0000 . ?
C4 C3 1.384(2) . ?
C4 C5 1.3864(19) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C12 H12 0.9500 . ?
C1 C2 1.396(2) . ?
C1 H1 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C17 N2 1.4497(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C3 C2 1.382(2) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?

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
C11 C10 C15 117.61(12) . . ?
C11 C10 C9 120.10(11) . . ?
C15 C10 C9 122.26(12) . . ?
N2 C13 C12 121.76(12) . . ?
N2 C13 C14 120.85(12) . . ?
C12 C13 C14 117.39(11) . . ?
C12 C11 C10 121.91(13) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C14 C15 C10 121.52(13) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
N1 C9 C10 123.75(12) . . ?
N1 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C15 C14 C13 120.89(12) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C1 C6 C5 118.43(12) . . ?
C1 C6 C7 123.32(12) . . ?
C5 C6 C7 118.25(12) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C7 C8 107.88(11) . . ?
N1 C7 C6 108.43(10) . . ?
C8 C7 C6 114.77(11) . . ?
N1 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C6 C7 H7 108.5 . . ?
C3 C4 C5 119.93(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.19(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C11 C12 C13 120.65(13) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C6 C1 C2 120.48(13) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C3 C4 119.65(13) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C2 C1 120.31(13) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C9 N1 C7 117.11(11) . . ?
C13 N2 C17 120.69(12) . . ?
C13 N2 C16 119.98(12) . . ?
C17 N2 C16 116.92(11) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 953131'
