# Electronic Supplementary Material (ESI) for ChemComm.
# 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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#  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_sa115m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N2'
_chemical_formula_weight         184.24

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                   7.7787(10)
_cell_length_b                   8.3955(11)
_cell_length_c                   15.691(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.859(2)
_cell_angle_gamma                90.00
_cell_volume                     1022.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5534
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         26.03
_reflns_number_total             2015
_reflns_number_gt                1225
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0773P)²+0.0000P] 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         2015
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.005
_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
C1 C -0.1858(3) 0.0134(3) 0.65198(14) 0.0581(6) Uani 1 1 d . . .
C2 C -0.2918(3) -0.1096(3) 0.67434(14) 0.0619(6) Uani 1 1 d . . .
H2 H -0.405(3) -0.088(2) 0.6934(12) 0.068(6) Uiso 1 1 d . . .
C3 C -0.2395(3) -0.2662(3) 0.67489(12) 0.0580(6) Uani 1 1 d . . .
C4 C -0.0742(3) -0.2947(3) 0.65201(15) 0.0643(6) Uani 1 1 d . . .
H4 H -0.033(3) -0.398(3) 0.6565(15) 0.091(8) Uiso 1 1 d . . .
C5 C 0.0348(3) -0.1751(3) 0.62897(14) 0.0607(6) Uani 1 1 d . . .
H5 H 0.146(3) -0.202(3) 0.6132(14) 0.075(7) Uiso 1 1 d . . .
C6 C -0.0210(2) -0.0170(2) 0.62777(12) 0.0492(5) Uani 1 1 d . . .
C7 C 0.0368(3) 0.2764(2) 0.60851(17) 0.0573(6) Uani 1 1 d . . .
H7B H -0.063(3) 0.295(2) 0.5673(12) 0.060(6) Uiso 1 1 d . . .
H7A H 0.008(2) 0.305(2) 0.6670(13) 0.066(6) Uiso 1 1 d . . .
C8 C 0.1948(3) 0.3682(3) 0.58050(19) 0.0652(6) Uani 1 1 d . . .
H8B H 0.251(3) 0.435(3) 0.6280(15) 0.090(8) Uiso 1 1 d . . .
H8A H 0.166(3) 0.445(3) 0.5317(17) 0.106(9) Uiso 1 1 d . . .
C9 C 0.3135(2) 0.2363(2) 0.55682(12) 0.0511(5) Uani 1 1 d . . .
C10 C 0.2428(2) 0.0947(3) 0.57140(13) 0.0540(5) Uani 1 1 d . . .
H10 H 0.291(2) -0.011(2) 0.5637(12) 0.064(6) Uiso 1 1 d . . .
C11 C 0.4756(3) 0.2590(2) 0.52248(13) 0.0581(6) Uani 1 1 d . . .
C12 C -0.3566(4) -0.4005(4) 0.6972(2) 0.0830(8) Uani 1 1 d . . .
H12C H -0.297(5) -0.485(5) 0.730(3) 0.169(16) Uiso 1 1 d . . .
H12B H -0.413(5) -0.449(5) 0.650(3) 0.187(17) Uiso 1 1 d . . .
H12A H -0.438(4) -0.363(5) 0.730(2) 0.145(15) Uiso 1 1 d . . .
N1 N 0.0852(2) 0.10706(18) 0.60348(10) 0.0539(5) Uani 1 1 d . . .
N2 N 0.6063(2) 0.2813(2) 0.49518(13) 0.0780(6) Uani 1 1 d . . .
H1 H -0.228(3) 0.121(3) 0.6491(13) 0.071(6) 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
C1 0.0519(12) 0.0541(14) 0.0698(14) -0.0025(11) 0.0140(9) 0.0039(10)
C2 0.0517(13) 0.0664(15) 0.0692(14) -0.0053(11) 0.0163(10) -0.0051(11)
C3 0.0627(14) 0.0606(15) 0.0511(12) -0.0005(10) 0.0075(10) -0.0124(11)
C4 0.0707(15) 0.0482(14) 0.0757(15) 0.0003(11) 0.0161(11) -0.0008(12)
C5 0.0567(14) 0.0518(13) 0.0758(15) -0.0020(11) 0.0196(11) 0.0044(11)
C6 0.0496(11) 0.0483(12) 0.0504(11) -0.0014(9) 0.0095(8) -0.0017(9)
C7 0.0569(13) 0.0459(13) 0.0699(16) 0.0020(10) 0.0115(11) 0.0047(10)
C8 0.0620(14) 0.0523(14) 0.0831(17) 0.0007(13) 0.0190(12) -0.0029(11)
C9 0.0449(11) 0.0508(12) 0.0581(12) -0.0004(9) 0.0084(8) 0.0014(9)
C10 0.0479(12) 0.0516(13) 0.0632(14) 0.0000(10) 0.0099(9) 0.0032(10)
C11 0.0515(13) 0.0543(13) 0.0687(14) 0.0068(10) 0.0054(10) -0.0005(10)
C12 0.087(2) 0.079(2) 0.083(2) 0.0099(16) 0.0145(17) -0.0275(16)
N1 0.0503(10) 0.0420(10) 0.0711(12) -0.0018(8) 0.0160(8) 0.0032(7)
N2 0.0544(12) 0.0703(14) 0.1115(16) 0.0105(11) 0.0206(10) -0.0015(9)

_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
C1 C2 1.382(3) . ?
C1 C6 1.385(3) . ?
C1 H1 0.97(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.97(2) . ?
C3 C4 1.379(3) . ?
C3 C12 1.506(3) . ?
C4 C5 1.378(3) . ?
C4 H4 0.92(3) . ?
C5 C6 1.395(3) . ?
C5 H5 0.94(2) . ?
C6 N1 1.398(2) . ?
C7 N1 1.474(3) . ?
C7 C8 1.539(3) . ?
C7 H7B 0.99(2) . ?
C7 H7A 0.99(2) . ?
C8 C9 1.505(3) . ?
C8 H8B 1.01(2) . ?
C8 H8A 1.01(3) . ?
C9 C10 1.336(3) . ?
C9 C11 1.417(3) . ?
C10 N1 1.360(2) . ?
C10 H10 0.97(2) . ?
C11 N2 1.145(2) . ?
C12 H12C 0.98(4) . ?
C12 H12B 0.93(5) . ?
C12 H12A 0.90(4) . ?

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 C1 C6 120.7(2) . . ?
C2 C1 H1 120.4(13) . . ?
C6 C1 H1 118.7(13) . . ?
C3 C2 C1 122.3(2) . . ?
C3 C2 H2 117.0(13) . . ?
C1 C2 H2 120.6(12) . . ?
C2 C3 C4 116.4(2) . . ?
C2 C3 C12 122.3(2) . . ?
C4 C3 C12 121.3(2) . . ?
C5 C4 C3 122.9(2) . . ?
C5 C4 H4 119.2(16) . . ?
C3 C4 H4 117.7(16) . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 119.2(13) . . ?
C6 C5 H5 120.8(13) . . ?
C1 C6 C5 117.64(19) . . ?
C1 C6 N1 120.80(18) . . ?
C5 C6 N1 121.56(18) . . ?
N1 C7 C8 104.86(17) . . ?
N1 C7 H7B 108.1(11) . . ?
C8 C7 H7B 110.0(11) . . ?
N1 C7 H7A 111.2(12) . . ?
C8 C7 H7A 112.0(12) . . ?
H7B C7 H7A 110.4(17) . . ?
C9 C8 C7 102.51(18) . . ?
C9 C8 H8B 110.2(13) . . ?
C7 C8 H8B 112.5(14) . . ?
C9 C8 H8A 112.9(15) . . ?
C7 C8 H8A 113.1(14) . . ?
H8B C8 H8A 106(2) . . ?
C10 C9 C11 124.86(18) . . ?
C10 C9 C8 110.26(17) . . ?
C11 C9 C8 124.87(18) . . ?
C9 C10 N1 112.77(19) . . ?
C9 C10 H10 128.6(12) . . ?
N1 C10 H10 118.6(12) . . ?
N2 C11 C9 178.3(2) . . ?
C3 C12 H12C 113(2) . . ?
C3 C12 H12B 113(2) . . ?
H12C C12 H12B 107(3) . . ?
C3 C12 H12A 109(3) . . ?
H12C C12 H12A 107(3) . . ?
H12B C12 H12A 107(3) . . ?
C10 N1 C6 127.42(17) . . ?
C10 N1 C7 109.45(17) . . ?
C6 N1 C7 123.12(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 994058'
