# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_13mjd3h

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N'
_chemical_formula_weight         209.28

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7019(4)
_cell_length_b                   9.4338(5)
_cell_length_c                   10.0092(5)
_cell_angle_alpha                63.0521(8)
_cell_angle_beta                 68.8273(7)
_cell_angle_gamma                71.1657(8)
_cell_volume                     593.34(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5247
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_process_details   SADABS

_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            12294
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2959
_reflns_number_gt                2537
_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)+(0.0692P)²+0.2385P] 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_number_reflns         2959
_refine_ls_number_parameters     128
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.063
_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 1.33690(18) 0.10156(16) 1.14798(14) 0.0360(3) Uani 1 1 d . . .
C1 C 1.28570(19) 0.11235(16) 1.04844(16) 0.0300(3) Uani 1 1 d . . .
C2 C 1.22645(19) 0.12783(16) 0.92121(15) 0.0294(3) Uani 1 1 d . . .
H2 H 1.3147 0.0869 0.8460 0.035 Uiso 1 1 calc R . .
C3 C 1.04997(18) 0.19843(15) 0.90614(14) 0.0270(3) Uani 1 1 d . B .
H3 H 0.9629 0.2329 0.9860 0.032 Uiso 1 1 calc R . .
C4 C 0.98043(17) 0.22674(15) 0.77703(14) 0.0253(3) Uani 1 1 d D . .
C5 C 0.80170(19) 0.30175(17) 0.77430(15) 0.0305(3) Uani 1 1 d . B .
H5 H 0.7261 0.3358 0.8572 0.037 Uiso 1 1 calc R A 1
C6 C 0.710(2) 0.3368(18) 0.6489(17) 0.0305(5) Uani 0.555(2) 1 d PD B 1
H6A H 0.6372 0.4493 0.6193 0.037 Uiso 0.555(2) 1 calc PR B 1
H6B H 0.6203 0.2629 0.6896 0.037 Uiso 0.555(2) 1 calc PR B 1
C7 C 0.8594(3) 0.3146(3) 0.5059(3) 0.0243(4) Uani 0.555(2) 1 d PD B 1
H7 H 0.9281 0.4073 0.4520 0.029 Uiso 0.555(2) 1 calc PR B 1
C8 C 1.0029(3) 0.1592(3) 0.5535(3) 0.0318(4) Uani 0.555(2) 1 d PD B 1
H8A H 1.0969 0.1468 0.4593 0.038 Uiso 0.555(2) 1 calc PR B 1
H8B H 0.9368 0.0663 0.6073 0.038 Uiso 0.555(2) 1 calc PR B 1
C9 C 1.1071(12) 0.1546(10) 0.6597(7) 0.0321(14) Uani 0.555(2) 1 d PD B 1
H9A H 1.1631 0.0407 0.7148 0.039 Uiso 0.555(2) 1 calc PR B 1
H9B H 1.2123 0.2147 0.5958 0.039 Uiso 0.555(2) 1 calc PR B 1
C10 C 0.7647(3) 0.3182(3) 0.3920(2) 0.0246(4) Uani 0.555(2) 1 d PGD B 1
C11 C 0.7950(3) 0.4316(2) 0.2405(2) 0.0246(4) Uani 0.555(2) 1 d PGD B 1
H11 H 0.8776 0.5043 0.2061 0.029 Uiso 0.555(2) 1 calc PR B 1
C12 C 0.7046(3) 0.4385(2) 0.13947(16) 0.0246(4) Uani 0.555(2) 1 d PG B 1
H12 H 0.7253 0.5160 0.0360 0.029 Uiso 0.555(2) 1 calc PR B 1
C13 C 0.5838(3) 0.3322(3) 0.1899(2) 0.0246(4) Uani 0.555(2) 1 d PG B 1
H13 H 0.5219 0.3369 0.1208 0.029 Uiso 0.555(2) 1 calc PR B 1
C14 C 0.5535(3) 0.2188(2) 0.3413(2) 0.0246(4) Uani 0.555(2) 1 d PG B 1
H14 H 0.4709 0.1461 0.3757 0.029 Uiso 0.555(2) 1 calc PR B 1
C15 C 0.6440(3) 0.2118(2) 0.44235(15) 0.0246(4) Uani 0.555(2) 1 d PGD B 1
H15 H 0.6232 0.1343 0.5459 0.029 Uiso 0.555(2) 1 calc PR B 1
C6' C 0.717(3) 0.338(2) 0.648(2) 0.0305(5) Uani 0.445(2) 1 d PD B 2
H6C H 0.7067 0.4550 0.5822 0.037 Uiso 0.445(2) 1 calc PR B 2
H6D H 0.5869 0.3144 0.6943 0.037 Uiso 0.445(2) 1 calc PR B 2
C7' C 0.8355(4) 0.2380(4) 0.5470(3) 0.0243(4) Uani 0.445(2) 1 d PD B 2
H7' H 0.8338 0.1209 0.6136 0.029 Uiso 0.445(2) 1 calc PR B 2
C8' C 1.0399(4) 0.2631(4) 0.4968(4) 0.0318(4) Uani 0.445(2) 1 d PD B 2
H8C H 1.1193 0.2098 0.4232 0.038 Uiso 0.445(2) 1 calc PR B 2
H8D H 1.0427 0.3803 0.4434 0.038 Uiso 0.445(2) 1 calc PR B 2
C9' C 1.1190(15) 0.1918(14) 0.6377(9) 0.0321(14) Uani 0.445(2) 1 d PD B 2
H9C H 1.1580 0.0730 0.6676 0.039 Uiso 0.445(2) 1 calc PR B 2
H9D H 1.2338 0.2356 0.6090 0.039 Uiso 0.445(2) 1 calc PR B 2
C10' C 0.7503(4) 0.2831(3) 0.4133(2) 0.0268(6) Uani 0.445(2) 1 d PGD B 2
C11' C 0.8070(4) 0.4041(3) 0.2703(3) 0.0268(6) Uani 0.445(2) 1 d PGD B 2
H11' H 0.8989 0.4609 0.2549 0.032 Uiso 0.445(2) 1 calc PR B 2
C12' C 0.7293(4) 0.4421(3) 0.1499(2) 0.0268(6) Uani 0.445(2) 1 d PG B 2
H12' H 0.7680 0.5248 0.0521 0.032 Uiso 0.445(2) 1 calc PR B 2
C13' C 0.5948(4) 0.3590(3) 0.1724(2) 0.0268(6) Uani 0.445(2) 1 d PG B 2
H13' H 0.5417 0.3850 0.0901 0.032 Uiso 0.445(2) 1 calc PR B 2
C14' C 0.5381(4) 0.2380(3) 0.3154(3) 0.0268(6) Uani 0.445(2) 1 d PG B 2
H14' H 0.4462 0.1812 0.3308 0.032 Uiso 0.445(2) 1 calc PR B 2
C15' C 0.6158(4) 0.2001(3) 0.4359(2) 0.0268(6) Uani 0.445(2) 1 d PGD B 2
H15' H 0.5771 0.1173 0.5336 0.032 Uiso 0.445(2) 1 calc PR B 2


_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 C1 1.1509(17) . ?
C1 C2 1.4351(17) . ?
C2 C3 1.3365(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4570(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3331(18) . ?
C4 C9 1.504(8) . ?
C4 C9' 1.518(9) . ?
C5 C6' 1.48(3) . ?
C5 C6 1.52(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.531(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.516(3) . ?
C7 C10 1.543(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.526(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C6' C7' 1.550(8) . ?
C6' H6C 0.9900 . ?
C6' H6D 0.9900 . ?
C7' C10' 1.530(3) . ?
C7' C8' 1.533(4) . ?
C7' H7' 1.0000 . ?
C8' C9' 1.520(8) . ?
C8' H8C 0.9900 . ?
C8' H8D 0.9900 . ?
C9' H9C 0.9900 . ?
C9' H9D 0.9900 . ?
C10' C11' 1.3900 . ?
C10' C15' 1.3900 . ?
C11' C12' 1.3900 . ?
C11' H11' 0.9500 . ?
C12' C13' 1.3900 . ?
C12' H12' 0.9500 . ?
C13' C14' 1.3900 . ?
C13' H13' 0.9500 . ?
C14' C15' 1.3900 . ?
C14' H14' 0.9500 . ?
C15' H15' 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
N1 C1 C2 178.36(14) . . ?
C3 C2 C1 121.53(12) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 125.24(12) . . ?
C2 C3 H3 117.4 . . ?
C4 C3 H3 117.4 . . ?
C5 C4 C3 119.30(11) . . ?
C5 C4 C9 122.0(3) . . ?
C3 C4 C9 118.4(3) . . ?
C5 C4 C9' 120.7(4) . . ?
C3 C4 C9' 119.4(3) . . ?
C4 C5 C6' 123.9(5) . . ?
C4 C5 C6 124.9(4) . . ?
C4 C5 H5 117.5 . . ?
C6' C5 H5 118.5 . . ?
C6 C5 H5 117.5 . . ?
C5 C6 C7 111.1(11) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 110.4(7) . . ?
C8 C7 C10 111.52(19) . . ?
C6 C7 C10 110.8(8) . . ?
C8 C7 H7 108.0 . . ?
C6 C7 H7 108.0 . . ?
C10 C7 H7 108.0 . . ?
C7 C8 C9 113.2(4) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C4 C9 C8 113.0(5) . . ?
C4 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C4 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 120.0 . . ?
C11 C10 C7 119.98(16) . . ?
C15 C10 C7 119.98(16) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C5 C6' C7' 112.1(14) . . ?
C5 C6' H6C 109.2 . . ?
C7' C6' H6C 109.2 . . ?
C5 C6' H6D 109.2 . . ?
C7' C6' H6D 109.2 . . ?
H6C C6' H6D 107.9 . . ?
C10' C7' C8' 114.6(2) . . ?
C10' C7' C6' 111.2(10) . . ?
C8' C7' C6' 106.6(9) . . ?
C10' C7' H7' 108.1 . . ?
C8' C7' H7' 108.1 . . ?
C6' C7' H7' 108.1 . . ?
C9' C8' C7' 109.9(5) . . ?
C9' C8' H8C 109.7 . . ?
C7' C8' H8C 109.7 . . ?
C9' C8' H8D 109.7 . . ?
C7' C8' H8D 109.7 . . ?
H8C C8' H8D 108.2 . . ?
C4 C9' C8' 114.1(7) . . ?
C4 C9' H9C 108.7 . . ?
C8' C9' H9C 108.7 . . ?
C4 C9' H9D 108.7 . . ?
C8' C9' H9D 108.7 . . ?
H9C C9' H9D 107.6 . . ?
C11' C10' C15' 120.0 . . ?
C11' C10' C7' 120.9(2) . . ?
C15' C10' C7' 119.1(2) . . ?
C10' C11' C12' 120.0 . . ?
C10' C11' H11' 120.0 . . ?
C12' C11' H11' 120.0 . . ?
C13' C12' C11' 120.0 . . ?
C13' C12' H12' 120.0 . . ?
C11' C12' H12' 120.0 . . ?
C12' C13' C14' 120.0 . . ?
C12' C13' H13' 120.0 . . ?
C14' C13' H13' 120.0 . . ?
C13' C14' C15' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C15' C14' H14' 120.0 . . ?
C14' C15' C10' 120.0 . . ?
C14' C15' H15' 120.0 . . ?
C10' C15' H15' 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.044

_database_code_depnum_ccdc_archive 'CCDC 991982'
