# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_cd1074b
#TrackingRef '19489_web_deposit_cif_file_0_OlegLarionov_1366054366.cd1074b.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N'
_chemical_formula_sum            'C16 H17 N'
_chemical_formula_weight         223.31

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)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   7.736(4)
_cell_length_b                   8.914(4)
_cell_length_c                   9.594(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.839(6)
_cell_angle_gamma                90.00
_cell_volume                     653.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    3288
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      40.2

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;

;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1
_diffrn_reflns_number            5213
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_reduction_process 'Lp corrections applied'
_reflns_number_total             2651
_reflns_number_gt                2577
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'publCIF (Westrip, 2010)'

_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^)+(0.0370P)^2^+0.1000P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2651
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_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 0.93555(13) 0.52333(13) 0.05735(10) 0.0207(2) Uani 1 1 d . . .
C11 C 0.63970(16) 0.48992(16) -0.09908(12) 0.0198(3) Uani 1 1 d . . .
C1 C 0.80569(16) 0.42307(15) -0.02469(12) 0.0211(3) Uani 1 1 d . . .
C12 C 0.50479(17) 0.39516(16) -0.16012(13) 0.0223(3) Uani 1 1 d . . .
C9 C 0.78316(17) 0.56601(16) 0.29936(13) 0.0236(3) Uani 1 1 d . . .
C4 C 0.92859(16) 0.47251(14) 0.30799(12) 0.0209(3) Uani 1 1 d . . .
C16 C 0.61944(18) 0.64453(16) -0.11731(14) 0.0236(3) Uani 1 1 d . . .
C5 C 0.97969(19) 0.39055(17) 0.43221(14) 0.0276(3) Uani 1 1 d . . .
C3 C 1.03237(16) 0.45513(15) 0.18676(13) 0.0215(3) Uani 1 1 d . . .
C13 C 0.35504(17) 0.45401(17) -0.24116(14) 0.0259(3) Uani 1 1 d . . .
C14 C 0.33691(19) 0.60825(18) -0.26082(15) 0.0282(3) Uani 1 1 d . . .
C8 C 0.69004(19) 0.57865(18) 0.41261(14) 0.0284(3) Uani 1 1 d . . .
C2 C 0.97692(17) 0.45655(18) -0.07333(13) 0.0264(3) Uani 1 1 d . . .
C15 C 0.46869(19) 0.70331(17) -0.19761(16) 0.0286(3) Uani 1 1 d . . .
C7 C 0.74190(19) 0.49640(19) 0.53522(14) 0.0329(3) Uani 1 1 d . . .
C10 C 1.21220(18) 0.53015(19) 0.21902(15) 0.0287(3) Uani 1 1 d . . .
C6 C 0.8866(2) 0.40309(19) 0.54452(15) 0.0332(3) Uani 1 1 d . . .
H10A H 1.280(2) 0.515(3) 0.1373(19) 0.050 Uiso 1 1 d . . .
H15A H 0.459(2) 0.811(2) -0.2101(19) 0.040 Uiso 1 1 d . . .
H8A H 0.586(2) 0.644(2) 0.4049(19) 0.040 Uiso 1 1 d . . .
H3A H 1.048(2) 0.347(2) 0.1726(19) 0.040 Uiso 1 1 d . . .
H12A H 0.516(2) 0.285(2) -0.1457(19) 0.040 Uiso 1 1 d . . .
H10B H 1.279(2) 0.484(2) 0.306(2) 0.050 Uiso 1 1 d . . .
H10C H 1.202(3) 0.643(3) 0.235(2) 0.050 Uiso 1 1 d . . .
H9A H 0.746(2) 0.626(2) 0.2129(19) 0.040 Uiso 1 1 d . . .
H1A H 0.796(2) 0.319(2) 0.0138(19) 0.040 Uiso 1 1 d . . .
H2B H 1.064(2) 0.378(2) -0.0636(19) 0.040 Uiso 1 1 d . . .
H2A H 0.978(2) 0.528(2) -0.1524(18) 0.040 Uiso 1 1 d . . .
H7A H 0.676(2) 0.499(2) 0.6121(18) 0.040 Uiso 1 1 d . . .
H6A H 0.921(2) 0.345(2) 0.6288(19) 0.040 Uiso 1 1 d . . .
H13A H 0.261(2) 0.391(2) -0.2863(19) 0.040 Uiso 1 1 d . . .
H14A H 0.233(2) 0.647(2) -0.3173(19) 0.040 Uiso 1 1 d . . .
H5A H 1.082(2) 0.325(2) 0.4387(19) 0.040 Uiso 1 1 d . . .
H16A H 0.714(2) 0.705(2) -0.076(2) 0.040 Uiso 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
N1 0.0187(5) 0.0257(6) 0.0176(5) -0.0009(4) 0.0023(4) -0.0006(4)
C11 0.0203(6) 0.0252(7) 0.0148(5) 0.0013(4) 0.0058(4) 0.0013(5)
C1 0.0216(6) 0.0227(7) 0.0187(5) -0.0011(5) 0.0026(5) -0.0001(5)
C12 0.0231(7) 0.0229(7) 0.0216(6) 0.0015(5) 0.0052(5) -0.0003(5)
C9 0.0238(6) 0.0273(7) 0.0189(6) 0.0000(5) 0.0008(5) -0.0018(5)
C4 0.0218(6) 0.0214(6) 0.0184(5) -0.0023(5) -0.0005(4) -0.0050(5)
C16 0.0226(7) 0.0229(7) 0.0262(6) -0.0004(5) 0.0061(5) -0.0011(5)
C5 0.0304(7) 0.0262(8) 0.0242(6) 0.0012(5) -0.0024(5) -0.0010(6)
C3 0.0205(6) 0.0217(7) 0.0216(6) -0.0007(5) 0.0009(4) 0.0012(5)
C13 0.0191(6) 0.0321(8) 0.0262(6) 0.0009(6) 0.0022(5) -0.0014(6)
C14 0.0209(7) 0.0355(8) 0.0279(7) 0.0061(6) 0.0030(5) 0.0061(6)
C8 0.0260(7) 0.0353(8) 0.0246(6) -0.0049(6) 0.0058(5) -0.0036(6)
C2 0.0222(6) 0.0368(8) 0.0207(6) -0.0020(5) 0.0054(5) 0.0036(6)
C15 0.0293(8) 0.0235(7) 0.0338(7) 0.0051(6) 0.0071(6) 0.0051(6)
C7 0.0357(8) 0.0430(9) 0.0211(6) -0.0041(6) 0.0077(5) -0.0131(7)
C10 0.0206(6) 0.0341(9) 0.0304(7) -0.0022(6) 0.0005(5) -0.0012(6)
C6 0.0428(9) 0.0359(9) 0.0193(6) 0.0054(6) -0.0007(6) -0.0095(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 C2 1.4669(17) . ?
N1 C1 1.4780(16) . ?
N1 C3 1.4786(16) . ?
C11 C16 1.395(2) . ?
C11 C12 1.3992(19) . ?
C11 C1 1.4938(17) . ?
C1 C2 1.5004(19) . ?
C1 H1A 1.007(19) . ?
C12 C13 1.3946(19) . ?
C12 H12A 1.00(2) . ?
C9 C4 1.3923(19) . ?
C9 C8 1.3974(18) . ?
C9 H9A 0.993(19) . ?
C4 C5 1.4020(18) . ?
C4 C3 1.5193(18) . ?
C16 C15 1.397(2) . ?
C16 H16A 0.95(2) . ?
C5 C6 1.390(2) . ?
C5 H5A 0.979(19) . ?
C3 C10 1.532(2) . ?
C3 H3A 0.99(2) . ?
C13 C14 1.392(2) . ?
C13 H13A 0.970(19) . ?
C14 C15 1.391(2) . ?
C14 H14A 0.960(19) . ?
C8 C7 1.392(2) . ?
C8 H8A 0.984(19) . ?
C2 H2B 0.97(2) . ?
C2 H2A 0.992(19) . ?
C15 H15A 0.97(2) . ?
C7 C6 1.386(2) . ?
C7 H7A 0.958(17) . ?
C10 H10A 1.017(19) . ?
C10 H10B 1.00(2) . ?
C10 H10C 1.02(2) . ?
C6 H6A 0.962(18) . ?

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
C2 N1 C1 61.26(9) . . ?
C2 N1 C3 113.69(11) . . ?
C1 N1 C3 114.44(11) . . ?
C16 C11 C12 118.79(12) . . ?
C16 C11 C1 121.72(12) . . ?
C12 C11 C1 119.36(13) . . ?
N1 C1 C11 118.51(11) . . ?
N1 C1 C2 59.01(8) . . ?
C11 C1 C2 120.48(11) . . ?
N1 C1 H1A 116.6(10) . . ?
C11 C1 H1A 115.7(11) . . ?
C2 C1 H1A 114.8(11) . . ?
C13 C12 C11 120.57(13) . . ?
C13 C12 H12A 119.9(11) . . ?
C11 C12 H12A 119.5(11) . . ?
C4 C9 C8 120.69(12) . . ?
C4 C9 H9A 120.2(10) . . ?
C8 C9 H9A 119.1(10) . . ?
C9 C4 C5 118.83(12) . . ?
C9 C4 C3 122.19(11) . . ?
C5 C4 C3 118.98(12) . . ?
C11 C16 C15 120.52(13) . . ?
C11 C16 H16A 116.5(11) . . ?
C15 C16 H16A 122.9(11) . . ?
C6 C5 C4 120.34(14) . . ?
C6 C5 H5A 120.6(11) . . ?
C4 C5 H5A 119.0(11) . . ?
N1 C3 C4 109.98(10) . . ?
N1 C3 C10 108.50(11) . . ?
C4 C3 C10 111.79(11) . . ?
N1 C3 H3A 110.2(10) . . ?
C4 C3 H3A 107.3(11) . . ?
C10 C3 H3A 109.0(10) . . ?
C14 C13 C12 120.32(13) . . ?
C14 C13 H13A 117.3(11) . . ?
C12 C13 H13A 122.4(11) . . ?
C15 C14 C13 119.39(14) . . ?
C15 C14 H14A 121.3(12) . . ?
C13 C14 H14A 119.3(12) . . ?
C7 C8 C9 119.91(14) . . ?
C7 C8 H8A 120.0(11) . . ?
C9 C8 H8A 120.1(11) . . ?
N1 C2 C1 59.73(8) . . ?
N1 C2 H2B 116.9(11) . . ?
C1 C2 H2B 117.5(11) . . ?
N1 C2 H2A 114.9(11) . . ?
C1 C2 H2A 118.5(10) . . ?
H2B C2 H2A 116.9(15) . . ?
C14 C15 C16 120.37(14) . . ?
C14 C15 H15A 121.0(11) . . ?
C16 C15 H15A 118.6(11) . . ?
C6 C7 C8 119.70(13) . . ?
C6 C7 H7A 118.8(11) . . ?
C8 C7 H7A 121.5(11) . . ?
C3 C10 H10A 110.2(11) . . ?
C3 C10 H10B 108.9(11) . . ?
H10A C10 H10B 109.0(16) . . ?
C3 C10 H10C 112.0(11) . . ?
H10A C10 H10C 108.0(17) . . ?
H10B C10 H10C 108.8(17) . . ?
C7 C6 C5 120.52(13) . . ?
C7 C6 H6A 119.5(11) . . ?
C5 C6 H6A 119.9(11) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032


_database_code_depnum_ccdc_archive 'CCDC 934181'