# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012


data_global
_journal_name_full               'New J.Chem.'
_journal_coden_cambridge         0440
_publ_contact_author_email       jeon@crpp-bordeaux.cnrs.fr
_publ_contact_author_name        'Ie-Rang Jeon'
loop_
_publ_author_name
'Parantap Sarkar'
'Ie-Rang Jeon'
'Fabien Durola'
'Harald Bock'

data_ij_l_ps3_0m
_database_code_depnum_ccdc_archive 'CCDC 856958'
#TrackingRef 'web_deposit_cif_file_0_Ie-RangJeon_1323099112.ij_l_ps3_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H32 N4'
_chemical_formula_weight         568.70

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                   9.1783(17)
_cell_length_b                   11.032(2)
_cell_length_c                   14.830(3)
_cell_angle_alpha                108.315(12)
_cell_angle_beta                 90.603(10)
_cell_angle_gamma                100.772(9)
_cell_volume                     1396.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1628
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.61

_exptl_crystal_description       'thin needle'
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ;
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_T_max  0.9920
_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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11287
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.1114
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         27.61
_reflns_number_total             6332
_reflns_number_gt                3023
_reflns_threshold_expression     >2\s(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    ?
_computing_publication_material  'WinGX (Farrugia)'

_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^ > 2\s(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^)+(0.1154P)^2^+0.0000P] 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         6332
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1629
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.2308
_refine_ls_wR_factor_gt          0.1831
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.009

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
C41 C 0.4963(3) 0.1531(3) -0.0318(2) 0.0179(7) Uani 1 1 d . . .
N2 N 0.3861(3) 0.2708(3) 0.47708(17) 0.0200(6) Uani 1 1 d . . .
N3 N 0.2330(3) 0.0838(3) -0.24442(19) 0.0256(7) Uani 1 1 d . . .
N4 N 0.6428(3) 0.1728(3) -0.01504(17) 0.0201(6) Uani 1 1 d . . .
C40 C 0.6051(3) 0.2070(3) 0.1533(2) 0.0156(6) Uani 1 1 d . . .
N6 N 0.7706(3) 0.5609(3) 0.70867(18) 0.0219(6) Uani 1 1 d . . .
C1 C 0.9910(4) 0.2697(4) -0.3936(3) 0.0367(9) Uani 1 1 d . . .
H1A H 0.9841 0.3569 -0.3566 0.055 Uiso 1 1 calc R . .
H1B H 1.0469 0.2718 -0.4476 0.055 Uiso 1 1 calc R . .
H1C H 1.0400 0.2317 -0.3550 0.055 Uiso 1 1 calc R . .
C2 C 0.8362(4) 0.1890(4) -0.4275(2) 0.0277(8) Uani 1 1 d . . .
H2A H 0.8433 0.1002 -0.4629 0.033 Uiso 1 1 calc R . .
H2B H 0.7895 0.2240 -0.4701 0.033 Uiso 1 1 calc R . .
C3 C 0.7402(3) 0.1885(3) -0.3447(2) 0.0233(7) Uani 1 1 d . . .
H3A H 0.7333 0.2775 -0.3097 0.028 Uiso 1 1 calc R . .
H3B H 0.7884 0.1548 -0.3018 0.028 Uiso 1 1 calc R . .
C4 C 0.5840(3) 0.1074(3) -0.3750(2) 0.0229(7) Uani 1 1 d . . .
H4A H 0.5371 0.1398 -0.4192 0.027 Uiso 1 1 calc R . .
H4B H 0.5912 0.0182 -0.4088 0.027 Uiso 1 1 calc R . .
C5 C 0.4848(3) 0.1079(3) -0.2940(2) 0.0210(7) Uani 1 1 d . . .
C6 C 0.5395(3) 0.1316(3) -0.2018(2) 0.0205(7) Uani 1 1 d . . .
H6 H 0.6417 0.1491 -0.1872 0.025 Uiso 1 1 calc R . .
C7 C 0.4419(3) 0.1296(3) -0.1300(2) 0.0180(7) Uani 1 1 d . . .
C8 C 0.3930(3) 0.1498(3) 0.0392(2) 0.0185(7) Uani 1 1 d . . .
C9 C 0.4503(3) 0.1684(3) 0.1330(2) 0.0167(6) Uani 1 1 d . . .
C10 C 0.3603(3) 0.1492(3) 0.2108(2) 0.0178(6) Uani 1 1 d . . .
C11 C 0.4235(3) 0.2110(3) 0.3068(2) 0.0170(6) Uani 1 1 d . . .
C12 C 0.3353(3) 0.2084(3) 0.3849(2) 0.0177(7) Uani 1 1 d . . .
C13 C 0.5227(3) 0.3447(3) 0.4948(2) 0.0174(7) Uani 1 1 d . . .
C14 C 0.5720(3) 0.4170(3) 0.5946(2) 0.0192(7) Uani 1 1 d . . .
C15 C 0.4819(3) 0.4114(3) 0.6691(2) 0.0204(7) Uani 1 1 d . . .
H15 H 0.3850 0.3633 0.6557 0.024 Uiso 1 1 calc R . .
C16 C 0.5357(3) 0.4768(3) 0.7623(2) 0.0216(7) Uani 1 1 d . . .
C17 C 0.4473(4) 0.4752(3) 0.8473(2) 0.0253(7) Uani 1 1 d . . .
H17A H 0.4703 0.5615 0.8942 0.030 Uiso 1 1 calc R . .
H17B H 0.4797 0.4156 0.8756 0.030 Uiso 1 1 calc R . .
C18 C 0.2806(3) 0.4359(3) 0.8261(2) 0.0267(8) Uani 1 1 d . . .
H18A H 0.2567 0.3488 0.7803 0.032 Uiso 1 1 calc R . .
H18B H 0.2477 0.4946 0.7971 0.032 Uiso 1 1 calc R . .
C19 C 0.1960(4) 0.4377(4) 0.9135(2) 0.0319(8) Uani 1 1 d . . .
H19A H 0.2112 0.5264 0.9567 0.038 Uiso 1 1 calc R . .
H19B H 0.2347 0.3855 0.9461 0.038 Uiso 1 1 calc R . .
C20 C 0.0307(4) 0.3852(4) 0.8879(3) 0.0428(10) Uani 1 1 d . . .
H20A H -0.0090 0.4396 0.8587 0.064 Uiso 1 1 calc R . .
H20B H -0.0187 0.3849 0.9446 0.064 Uiso 1 1 calc R . .
H20C H 0.0154 0.2980 0.8442 0.064 Uiso 1 1 calc R . .
C21 C 0.3295(3) 0.0843(3) -0.3101(2) 0.0253(7) Uani 1 1 d . . .
H21 H 0.2912 0.0677 -0.3721 0.030 Uiso 1 1 calc R . .
C22 C 0.2900(3) 0.1066(3) -0.1536(2) 0.0199(7) Uani 1 1 d . . .
C23 C 0.6984(3) 0.2007(3) 0.0754(2) 0.0179(7) Uani 1 1 d . . .
C24 C 0.7154(3) 0.4950(3) 0.6167(2) 0.0185(7) Uani 1 1 d . . .
C25 C 0.6820(3) 0.5490(3) 0.7768(2) 0.0222(7) Uani 1 1 d . . .
H25 H 0.7201 0.5921 0.8395 0.027 Uiso 1 1 calc R . .
C26 C 0.8054(3) 0.5103(3) 0.5420(2) 0.0207(7) Uani 1 1 d . . .
H26 H 0.8966 0.5681 0.5570 0.025 Uiso 1 1 calc R . .
C27 C 0.7614(3) 0.4428(3) 0.4498(2) 0.0191(7) Uani 1 1 d . . .
H27 H 0.8231 0.4560 0.4029 0.023 Uiso 1 1 calc R . .
C28 C 0.6219(3) 0.3510(3) 0.4217(2) 0.0187(7) Uani 1 1 d . . .
C29 C 0.5751(3) 0.2729(3) 0.3275(2) 0.0188(7) Uani 1 1 d . . .
C30 C 0.6725(3) 0.2479(3) 0.2484(2) 0.0182(7) Uani 1 1 d . . .
C31 C 0.8237(3) 0.2599(3) 0.2601(2) 0.0206(7) Uani 1 1 d . . .
H31 H 0.8676 0.2769 0.3208 0.025 Uiso 1 1 calc R . .
C32 C 0.9141(3) 0.2472(3) 0.1831(2) 0.0224(7) Uani 1 1 d . . .
H32 H 1.0162 0.2558 0.1933 0.027 Uiso 1 1 calc R . .
C33 C 0.8528(3) 0.2224(3) 0.0933(2) 0.0213(7) Uani 1 1 d . . .
H33 H 0.9142 0.2198 0.0435 0.026 Uiso 1 1 calc R . .
C34 C 0.1899(3) 0.1331(3) 0.3657(2) 0.0211(7) Uani 1 1 d . . .
H34 H 0.1309 0.1303 0.4159 0.025 Uiso 1 1 calc R . .
C35 C 0.1342(3) 0.0639(3) 0.2741(2) 0.0226(7) Uani 1 1 d . . .
H35 H 0.0394 0.0118 0.2628 0.027 Uiso 1 1 calc R . .
C36 C 0.2199(3) 0.0713(3) 0.1970(2) 0.0204(7) Uani 1 1 d . . .
H36 H 0.1810 0.0226 0.1354 0.025 Uiso 1 1 calc R . .
C37 C 0.2390(3) 0.1346(3) 0.0110(2) 0.0213(7) Uani 1 1 d . . .
H37 H 0.1704 0.1396 0.0571 0.026 Uiso 1 1 calc R . .
C38 C 0.1896(3) 0.1132(3) -0.0800(2) 0.0238(7) Uani 1 1 d . . .
H38 H 0.0883 0.1027 -0.0949 0.029 Uiso 1 1 calc R . .

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
C41 0.0282(17) 0.0141(16) 0.0107(15) 0.0019(14) -0.0022(12) 0.0062(12)
N2 0.0292(15) 0.0178(14) 0.0119(13) 0.0026(12) 0.0000(10) 0.0059(11)
N3 0.0334(16) 0.0266(17) 0.0151(14) 0.0057(13) -0.0036(12) 0.0040(12)
N4 0.0315(15) 0.0185(15) 0.0073(12) -0.0006(12) -0.0012(10) 0.0060(11)
C40 0.0229(16) 0.0126(16) 0.0097(14) 0.0006(13) -0.0020(12) 0.0047(11)
N6 0.0332(15) 0.0181(15) 0.0119(13) -0.0001(12) -0.0009(11) 0.0080(11)
C1 0.044(2) 0.041(2) 0.0239(19) 0.0083(19) 0.0076(16) 0.0113(17)
C2 0.045(2) 0.026(2) 0.0152(16) 0.0061(16) 0.0044(15) 0.0165(15)
C3 0.0397(19) 0.0225(18) 0.0095(15) 0.0042(15) 0.0015(13) 0.0124(14)
C4 0.0372(19) 0.0231(18) 0.0092(15) 0.0035(15) 0.0003(13) 0.0108(14)
C5 0.0341(18) 0.0146(17) 0.0104(14) -0.0013(14) -0.0017(13) 0.0052(12)
C6 0.0264(17) 0.0193(17) 0.0140(15) 0.0021(15) -0.0026(13) 0.0063(12)
C7 0.0299(17) 0.0113(16) 0.0116(15) 0.0006(14) -0.0005(12) 0.0068(12)
C8 0.0276(17) 0.0144(16) 0.0130(15) 0.0026(14) 0.0000(13) 0.0057(12)
C9 0.0267(17) 0.0140(16) 0.0082(14) -0.0004(13) -0.0010(12) 0.0079(12)
C10 0.0229(16) 0.0178(16) 0.0138(15) 0.0033(14) 0.0016(12) 0.0100(12)
C11 0.0225(16) 0.0177(17) 0.0120(15) 0.0043(14) 0.0005(12) 0.0079(12)
C12 0.0289(17) 0.0153(16) 0.0100(14) 0.0032(14) 0.0004(12) 0.0087(12)
C13 0.0252(17) 0.0173(17) 0.0110(14) 0.0043(14) 0.0008(12) 0.0079(12)
C14 0.0280(17) 0.0199(17) 0.0109(15) 0.0047(14) 0.0004(12) 0.0085(13)
C15 0.0265(17) 0.0196(17) 0.0150(15) 0.0048(15) -0.0015(12) 0.0061(12)
C16 0.0311(18) 0.0228(18) 0.0125(15) 0.0048(15) 0.0017(13) 0.0110(13)
C17 0.046(2) 0.0202(18) 0.0093(15) 0.0013(15) 0.0042(14) 0.0115(14)
C18 0.041(2) 0.0241(19) 0.0140(16) 0.0036(16) 0.0091(14) 0.0070(14)
C19 0.048(2) 0.026(2) 0.0181(17) 0.0017(17) 0.0112(15) 0.0084(16)
C20 0.051(2) 0.042(3) 0.029(2) 0.003(2) 0.0193(18) 0.0061(18)
C21 0.0353(19) 0.0249(19) 0.0135(15) 0.0046(15) -0.0029(14) 0.0037(14)
C22 0.0298(18) 0.0146(16) 0.0132(15) 0.0022(14) -0.0023(13) 0.0036(12)
C23 0.0262(17) 0.0135(16) 0.0117(15) 0.0000(14) 0.0008(12) 0.0055(12)
C24 0.0273(17) 0.0145(16) 0.0123(15) 0.0005(14) -0.0009(12) 0.0080(12)
C25 0.0377(19) 0.0143(17) 0.0111(15) -0.0035(14) -0.0017(13) 0.0104(13)
C26 0.0244(17) 0.0213(18) 0.0130(15) 0.0009(15) -0.0009(12) 0.0047(13)
C27 0.0265(17) 0.0187(17) 0.0124(15) 0.0038(14) 0.0025(12) 0.0068(12)
C28 0.0251(16) 0.0170(17) 0.0140(15) 0.0042(15) -0.0012(12) 0.0059(12)
C29 0.0299(17) 0.0164(16) 0.0110(14) 0.0044(14) -0.0003(12) 0.0071(12)
C30 0.0275(17) 0.0150(16) 0.0088(14) -0.0009(13) -0.0022(12) 0.0047(12)
C31 0.0315(18) 0.0174(17) 0.0097(14) -0.0017(14) -0.0033(13) 0.0078(13)
C32 0.0242(17) 0.0236(19) 0.0168(16) 0.0011(15) -0.0009(13) 0.0076(13)
C33 0.0284(17) 0.0227(18) 0.0106(15) 0.0005(14) 0.0032(12) 0.0081(13)
C34 0.0268(17) 0.0234(18) 0.0131(15) 0.0047(15) 0.0018(13) 0.0074(13)
C35 0.0265(17) 0.0226(18) 0.0195(17) 0.0091(16) -0.0015(13) 0.0026(13)
C36 0.0307(18) 0.0173(17) 0.0123(15) 0.0026(14) -0.0010(13) 0.0062(13)
C37 0.0275(17) 0.0236(18) 0.0155(16) 0.0086(15) 0.0037(13) 0.0080(13)
C38 0.0271(17) 0.0243(19) 0.0171(16) 0.0033(16) -0.0047(13) 0.0039(13)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C41 N4 1.329(4) . ?
C41 C8 1.429(4) . ?
C41 C7 1.461(4) . ?
N2 C13 1.335(4) . ?
N2 C12 1.355(4) . ?
N3 C21 1.324(4) . ?
N3 C22 1.369(4) . ?
N4 C23 1.350(4) . ?
C40 C9 1.406(4) . ?
C40 C30 1.433(4) . ?
C40 C23 1.436(4) . ?
N6 C25 1.327(4) . ?
N6 C24 1.368(4) . ?
C1 C2 1.515(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.520(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.520(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.515(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.378(4) . ?
C5 C21 1.405(4) . ?
C6 C7 1.402(4) . ?
C6 H6 0.9300 . ?
C7 C22 1.390(4) . ?
C8 C9 1.421(4) . ?
C8 C37 1.433(4) . ?
C9 C10 1.472(4) . ?
C10 C36 1.383(4) . ?
C10 C11 1.433(4) . ?
C11 C29 1.414(4) . ?
C11 C12 1.424(4) . ?
C12 C34 1.407(4) . ?
C13 C28 1.433(4) . ?
C13 C14 1.462(4) . ?
C14 C15 1.397(4) . ?
C14 C24 1.403(4) . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C16 C25 1.404(4) . ?
C16 C17 1.509(4) . ?
C17 C18 1.511(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.514(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.517(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9300 . ?
C22 C38 1.430(4) . ?
C23 C33 1.401(4) . ?
C24 C26 1.422(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.350(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.441(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.404(4) . ?
C29 C30 1.470(4) . ?
C30 C31 1.373(4) . ?
C31 C32 1.406(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.364(4) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C35 1.370(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.409(4) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C38 1.353(4) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?

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
N4 C41 C8 123.7(3) . . ?
N4 C41 C7 116.4(3) . . ?
C8 C41 C7 119.8(3) . . ?
C13 N2 C12 117.9(3) . . ?
C21 N3 C22 117.0(3) . . ?
C41 N4 C23 118.3(2) . . ?
C9 C40 C30 122.1(3) . . ?
C9 C40 C23 118.6(3) . . ?
C30 C40 C23 119.3(3) . . ?
C25 N6 C24 117.0(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 111.6(3) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 113.6(3) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 114.7(3) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C21 116.6(3) . . ?
C6 C5 C4 123.0(3) . . ?
C21 C5 C4 120.5(3) . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C22 C7 C6 118.5(3) . . ?
C22 C7 C41 119.9(3) . . ?
C6 C7 C41 121.6(3) . . ?
C9 C8 C41 118.0(3) . . ?
C9 C8 C37 124.9(3) . . ?
C41 C8 C37 117.0(3) . . ?
C40 C9 C8 117.7(3) . . ?
C40 C9 C10 117.1(2) . . ?
C8 C9 C10 125.1(3) . . ?
C36 C10 C11 117.6(3) . . ?
C36 C10 C9 124.0(3) . . ?
C11 C10 C9 118.3(3) . . ?
C29 C11 C12 117.8(3) . . ?
C29 C11 C10 121.7(3) . . ?
C12 C11 C10 120.5(3) . . ?
N2 C12 C34 118.2(3) . . ?
N2 C12 C11 123.3(3) . . ?
C34 C12 C11 118.5(3) . . ?
N2 C13 C28 123.0(3) . . ?
N2 C13 C14 117.0(3) . . ?
C28 C13 C14 120.0(3) . . ?
C15 C14 C24 118.5(3) . . ?
C15 C14 C13 122.5(3) . . ?
C24 C14 C13 119.0(3) . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C25 116.6(3) . . ?
C15 C16 C17 124.1(3) . . ?
C25 C16 C17 119.3(3) . . ?
C16 C17 C18 115.2(3) . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 C19 113.5(3) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 C20 111.8(3) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C5 125.4(3) . . ?
N3 C21 H21 117.3 . . ?
C5 C21 H21 117.3 . . ?
N3 C22 C7 122.4(3) . . ?
N3 C22 C38 118.4(3) . . ?
C7 C22 C38 119.1(3) . . ?
N4 C23 C33 118.4(3) . . ?
N4 C23 C40 122.5(3) . . ?
C33 C23 C40 119.1(3) . . ?
N6 C24 C14 122.0(3) . . ?
N6 C24 C26 118.3(3) . . ?
C14 C24 C26 119.7(3) . . ?
N6 C25 C16 125.5(3) . . ?
N6 C25 H25 117.2 . . ?
C16 C25 H25 117.2 . . ?
C27 C26 C24 121.5(3) . . ?
C27 C26 H26 119.2 . . ?
C24 C26 H26 119.2 . . ?
C26 C27 C28 122.0(3) . . ?
C26 C27 H27 119.0 . . ?
C28 C27 H27 119.0 . . ?
C29 C28 C13 118.5(3) . . ?
C29 C28 C27 124.2(3) . . ?
C13 C28 C27 117.1(3) . . ?
C28 C29 C11 118.0(3) . . ?
C28 C29 C30 125.0(3) . . ?
C11 C29 C30 117.0(3) . . ?
C31 C30 C40 118.1(3) . . ?
C31 C30 C29 124.0(3) . . ?
C40 C30 C29 117.9(3) . . ?
C30 C31 C32 121.9(3) . . ?
C30 C31 H31 119.0 . . ?
C32 C31 H31 119.0 . . ?
C33 C32 C31 120.3(3) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C23 120.6(3) . . ?
C32 C33 H33 119.7 . . ?
C23 C33 H33 119.7 . . ?
C35 C34 C12 120.9(3) . . ?
C35 C34 H34 119.6 . . ?
C12 C34 H34 119.6 . . ?
C34 C35 C36 120.3(3) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C10 C36 C35 121.6(3) . . ?
C10 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C38 C37 C8 122.6(3) . . ?
C38 C37 H37 118.7 . . ?
C8 C37 H37 118.7 . . ?
C37 C38 C22 121.2(3) . . ?
C37 C38 H38 119.4 . . ?
C22 C38 H38 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.881
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.078

# Attachment 'web_deposit_cif_file_1_Ie-RangJeon_1323099112.ij_p_amine_0m.cif'

data_ij_p_amine_0m
_database_code_depnum_ccdc_archive 'CCDC 856959'
#TrackingRef 'web_deposit_cif_file_1_Ie-RangJeon_1323099112.ij_p_amine_0m.cif'

_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           trigonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   18.669(5)
_cell_length_b                   18.669(5)
_cell_length_c                   16.853(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                120.000(5)
_cell_volume                     5087(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9243
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      29.08

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1944
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9861
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   sababs

_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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19088
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         29.18
_reflns_number_total             3058
_reflns_number_gt                2644
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir 97'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX (Farrugia)'

_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^ > 2\s(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^)+(0.0807P)^2^+4.9092P] 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_number_reflns         3058
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.81760(6) -0.03858(6) 0.52075(6) 0.0160(2) Uani 1 1 d . . .
C1 C 0.82065(6) -0.01032(6) 0.59771(6) 0.0141(2) Uani 1 1 d . . .
C2 C 0.68050(6) 0.07945(6) 0.58828(7) 0.0163(2) Uani 1 1 d . . .
C3 C 0.68845(7) 0.10394(7) 0.66878(7) 0.0179(2) Uani 1 1 d . . .
C4 C 0.87156(6) -0.01596(6) 0.65400(7) 0.0165(2) Uani 1 1 d . . .
H4 H 0.9029 -0.0402 0.6404 0.020 Uiso 1 1 calc R . .
C5 C 0.62918(7) 0.10073(7) 0.53446(7) 0.0197(2) Uani 1 1 d . . .
H5A H 0.6572 0.1604 0.5290 0.024 Uiso 1 1 calc R . .
H5B H 0.5768 0.0837 0.5606 0.024 Uiso 1 1 calc R . .
C6 C 0.83141(7) 0.05044(6) 0.75381(6) 0.0182(2) Uani 1 1 d . . .
H6 H 0.8347 0.0694 0.8054 0.022 Uiso 1 1 calc R . .
C7 C 0.77444(6) 0.02941(6) 0.61893(6) 0.0138(2) Uani 1 1 d . . .
C8 C 0.77977(6) 0.05856(6) 0.69752(6) 0.0152(2) Uani 1 1 d . . .
C9 C 0.87659(7) 0.01436(6) 0.73144(7) 0.0183(2) Uani 1 1 d . . .
H9 H 0.9113 0.0098 0.7682 0.022 Uiso 1 1 calc R . .
C10 C 0.61117(7) 0.06333(7) 0.45195(7) 0.0182(2) Uani 1 1 d . . .
H10A H 0.5755 0.0039 0.4560 0.022 Uiso 1 1 calc R . .
H10B H 0.6625 0.0740 0.4273 0.022 Uiso 1 1 calc R . .
C11 C 0.72338(6) 0.04117(6) 0.56434(6) 0.0151(2) Uani 1 1 d . . .
H11 H 0.7189 0.0229 0.5123 0.018 Uiso 1 1 calc R . .
C12 C 0.56953(8) 0.09881(8) 0.39959(7) 0.0237(3) Uani 1 1 d . . .
H12A H 0.5170 0.0858 0.4231 0.028 Uiso 1 1 calc R . .
H12B H 0.6040 0.1586 0.3981 0.028 Uiso 1 1 calc R . .
C13 C 0.55481(9) 0.06581(9) 0.31568(8) 0.0307(3) Uani 1 1 d . . .
H13A H 0.6061 0.0755 0.2931 0.046 Uiso 1 1 calc R . .
H13B H 0.5330 0.0935 0.2844 0.046 Uiso 1 1 calc R . .
H13C H 0.5160 0.0075 0.3162 0.046 Uiso 1 1 calc R . .
N2 N 0.73502(6) 0.09493(5) 0.72168(6) 0.0177(2) Uani 1 1 d . . .
H1C H 0.7723(10) -0.0543(9) 0.4924(9) 0.024(4) Uiso 1 1 d . . .
H1D H 0.8334(10) -0.0750(10) 0.5145(10) 0.027(4) Uiso 1 1 d . . .
H3 H 0.6579(9) 0.1299(9) 0.6871(9) 0.025(4) 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 0.0183(4) 0.0183(4) 0.0144(5) -0.0025(3) -0.0016(3) 0.0113(4)
C1 0.0139(4) 0.0123(4) 0.0137(5) 0.0012(3) 0.0013(4) 0.0049(3)
C2 0.0157(5) 0.0159(5) 0.0170(5) -0.0012(4) -0.0002(4) 0.0077(4)
C3 0.0191(5) 0.0176(5) 0.0175(5) -0.0013(4) 0.0033(4) 0.0095(4)
C4 0.0161(5) 0.0150(5) 0.0175(5) 0.0013(4) -0.0005(4) 0.0071(4)
C5 0.0204(5) 0.0204(5) 0.0225(6) -0.0041(4) -0.0033(4) 0.0133(4)
C6 0.0203(5) 0.0170(5) 0.0121(5) 0.0005(4) -0.0007(4) 0.0053(4)
C7 0.0144(4) 0.0125(4) 0.0130(5) 0.0008(3) 0.0014(3) 0.0055(4)
C8 0.0156(4) 0.0130(4) 0.0137(5) 0.0008(4) 0.0025(4) 0.0048(4)
C9 0.0182(5) 0.0173(5) 0.0156(5) 0.0022(4) -0.0039(4) 0.0061(4)
C10 0.0190(5) 0.0200(5) 0.0184(5) 0.0003(4) 0.0001(4) 0.0119(4)
C11 0.0161(5) 0.0155(4) 0.0133(5) -0.0017(4) -0.0005(4) 0.0075(4)
C12 0.0276(6) 0.0284(6) 0.0228(6) 0.0006(5) -0.0015(5) 0.0197(5)
C13 0.0365(7) 0.0460(8) 0.0213(6) 0.0005(5) -0.0028(5) 0.0293(6)
N2 0.0193(4) 0.0165(4) 0.0156(5) -0.0004(3) 0.0034(3) 0.0078(3)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 1.3906(14) . ?
N1 H1C 0.885(16) . ?
N1 H1D 0.872(17) . ?
C1 C4 1.3836(15) . ?
C1 C7 1.4360(14) . ?
C2 C11 1.3735(14) . ?
C2 C3 1.4155(16) . ?
C2 C5 1.5099(15) . ?
C3 N2 1.3135(15) . ?
C3 H3 0.965(15) . ?
C4 C9 1.4068(16) . ?
C4 H4 0.9300 . ?
C5 C10 1.5164(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.3694(16) . ?
C6 C8 1.4136(15) . ?
C6 H6 0.9300 . ?
C7 C8 1.4164(15) . ?
C7 C11 1.4187(14) . ?
C8 N2 1.3754(14) . ?
C9 H9 0.9300 . ?
C10 C12 1.5286(15) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9300 . ?
C12 C13 1.5118(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C1 N1 H1C 118.7(10) . . ?
C1 N1 H1D 116.3(11) . . ?
H1C N1 H1D 108.5(14) . . ?
C4 C1 N1 120.67(9) . . ?
C4 C1 C7 118.77(10) . . ?
N1 C1 C7 120.46(9) . . ?
C11 C2 C3 117.09(10) . . ?
C11 C2 C5 124.90(10) . . ?
C3 C2 C5 117.95(9) . . ?
N2 C3 C2 125.34(10) . . ?
N2 C3 H3 116.2(9) . . ?
C2 C3 H3 118.5(9) . . ?
C1 C4 C9 121.04(10) . . ?
C1 C4 H4 119.5 . . ?
C9 C4 H4 119.5 . . ?
C2 C5 C10 116.97(9) . . ?
C2 C5 H5A 108.1 . . ?
C10 C5 H5A 108.1 . . ?
C2 C5 H5B 108.1 . . ?
C10 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C9 C6 C8 119.27(10) . . ?
C9 C6 H6 120.4 . . ?
C8 C6 H6 120.4 . . ?
C8 C7 C11 118.07(9) . . ?
C8 C7 C1 119.11(9) . . ?
C11 C7 C1 122.83(9) . . ?
N2 C8 C7 121.55(9) . . ?
N2 C8 C6 118.00(10) . . ?
C7 C8 C6 120.46(10) . . ?
C6 C9 C4 121.31(10) . . ?
C6 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C5 C10 C12 111.93(9) . . ?
C5 C10 H10A 109.2 . . ?
C12 C10 H10A 109.2 . . ?
C5 C10 H10B 109.2 . . ?
C12 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C2 C11 C7 120.10(10) . . ?
C2 C11 H11 119.9 . . ?
C7 C11 H11 119.9 . . ?
C13 C12 C10 113.05(10) . . ?
C13 C12 H12A 109.0 . . ?
C10 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C10 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 N2 C8 117.81(10) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.18
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.094