# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                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.
#
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#  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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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_yangrl0605_twin1_hklf4
_audit_creation_date             2013-06-07
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H13 N'
_chemical_formula_sum            'C17 H13 N'
_chemical_formula_weight         231.28
_chemical_melting_point          ?
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.5135(13)
_cell_length_b                   7.3675(10)
_cell_length_c                   13.814(2)
_cell_angle_alpha                78.153(13)
_cell_angle_beta                 76.412(16)
_cell_angle_gamma                90.060(14)
_cell_volume                     629.80(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    891
_cell_measurement_temperature    297.1(3)
_cell_measurement_theta_max      26.4580
_cell_measurement_theta_min      3.8830
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4324
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.22
_diffrn_ambient_temperature      297.1(3)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   26.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   24.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700   77.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   76.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   56.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -38.0000  120.0000 70

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   61.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega   -4.00   98.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   38.0000  -60.0000 68
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0981834000
_diffrn_orient_matrix_UB_12      -0.0368101000
_diffrn_orient_matrix_UB_13      0.0056598000
_diffrn_orient_matrix_UB_21      0.0537154000
_diffrn_orient_matrix_UB_22      0.0689797000
_diffrn_orient_matrix_UB_23      -0.0422280000
_diffrn_orient_matrix_UB_31      0.0078628000
_diffrn_orient_matrix_UB_32      0.0598217000
_diffrn_orient_matrix_UB_33      0.0332254000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.5121 3435 1434
2 0.4879 3422 1434

_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2148
_reflns_number_total             4324
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1594
_refine_ls_R_factor_gt           0.0948
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1916P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2805
_refine_ls_wR_factor_ref         0.3187
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.7627(4) 0.2503(5) -0.0008(4) 0.0492(8) Uani 1 1 d . . .
C1 C 0.0532(4) 0.3319(5) 0.1947(3) 0.0415(10) Uani 1 1 d . . .
H1 H 0.0180 0.3910 0.1349 0.050 Uiso 1 1 calc R . .
C2 C -0.0836(6) 0.3335(6) 0.2865(4) 0.0571(13) Uani 1 1 d . . .
H2 H -0.2098 0.3932 0.2885 0.069 Uiso 1 1 calc R . .
C3 C -0.0352(6) 0.2483(6) 0.3747(4) 0.0627(15) Uani 1 1 d . . .
H3 H -0.1261 0.2529 0.4370 0.075 Uiso 1 1 calc R . .
C4 C 0.1500(6) 0.1544(6) 0.3718(4) 0.0561(12) Uani 1 1 d . . .
H4 H 0.1809 0.0922 0.4320 0.067 Uiso 1 1 calc R . .
C5 C 0.2883(5) 0.1534(5) 0.2793(4) 0.0482(11) Uani 1 1 d . . .
H5 H 0.4129 0.0914 0.2779 0.058 Uiso 1 1 calc R . .
C6 C 0.2439(5) 0.2435(5) 0.1886(3) 0.0387(10) Uani 1 1 d . . .
C7 C 0.3964(4) 0.2465(5) 0.0901(3) 0.0368(9) Uani 1 1 d . . .
C8 C 0.3352(4) 0.2507(6) -0.0004(4) 0.0379(7) Uani 1 1 d . . .
H8 H 0.1926 0.2520 -0.0006 0.045 Uiso 1 1 calc R . .
C9 C 0.4865(4) 0.2532(5) -0.0899(3) 0.0363(9) Uani 1 1 d . . .
C10 C 0.6971(5) 0.2504(5) -0.0847(3) 0.0441(11) Uani 1 1 d . . .
H10 H 0.7991 0.2485 -0.1442 0.053 Uiso 1 1 calc R . .
C11 C 0.6130(5) 0.2514(5) 0.0844(4) 0.0440(10) Uani 1 1 d . . .
H11 H 0.6565 0.2556 0.1434 0.053 Uiso 1 1 calc R . .
C12 C 0.4319(5) 0.2565(5) -0.1884(3) 0.0383(10) Uani 1 1 d . . .
C13 C 0.2474(5) 0.1681(5) -0.1938(3) 0.0434(11) Uani 1 1 d . . .
H13 H 0.1523 0.1102 -0.1338 0.052 Uiso 1 1 calc R . .
C14 C 0.2030(6) 0.1646(6) -0.2852(4) 0.0558(12) Uani 1 1 d . . .
H14 H 0.0804 0.1017 -0.2868 0.067 Uiso 1 1 calc R . .
C15 C 0.3398(7) 0.2544(6) -0.3762(4) 0.0597(13) Uani 1 1 d . . .
H15 H 0.3088 0.2527 -0.4384 0.072 Uiso 1 1 calc R . .
C16 C 0.5213(6) 0.3456(6) -0.3726(4) 0.0559(12) Uani 1 1 d . . .
H16 H 0.6133 0.4068 -0.4328 0.067 Uiso 1 1 calc R . .
C17 C 0.5677(5) 0.3469(5) -0.2806(3) 0.0468(11) Uani 1 1 d . . .
H17 H 0.6914 0.4088 -0.2795 0.056 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
N1 0.0292(14) 0.0595(17) 0.057(2) -0.0127(14) -0.0064(15) -0.0003(13)
C1 0.0354(16) 0.045(2) 0.042(3) -0.011(2) -0.0029(16) -0.0013(14)
C2 0.047(2) 0.059(3) 0.062(4) -0.021(3) -0.001(2) 0.0031(17)
C3 0.064(2) 0.068(3) 0.051(4) -0.025(3) 0.008(2) -0.004(2)
C4 0.071(2) 0.060(3) 0.034(3) -0.006(2) -0.008(2) -0.007(2)
C5 0.0457(19) 0.050(2) 0.048(3) -0.012(2) -0.0092(18) -0.0028(15)
C6 0.0352(16) 0.037(2) 0.042(3) -0.010(2) -0.0043(16) -0.0026(13)
C7 0.0315(16) 0.0334(19) 0.043(3) -0.0056(19) -0.0068(15) -0.0021(12)
C8 0.0283(15) 0.0383(16) 0.044(2) -0.0061(13) -0.0044(16) 0.0004(13)
C9 0.0295(15) 0.0343(19) 0.040(3) -0.0031(18) -0.0024(15) 0.0002(12)
C10 0.0315(17) 0.053(2) 0.043(3) -0.010(2) 0.0011(16) 0.0035(14)
C11 0.0371(17) 0.047(2) 0.045(3) -0.007(2) -0.0080(17) -0.0063(14)
C12 0.0375(16) 0.034(2) 0.041(3) -0.009(2) -0.0039(15) 0.0031(13)
C13 0.0352(16) 0.045(2) 0.049(3) -0.012(2) -0.0072(17) 0.0036(15)
C14 0.059(2) 0.055(3) 0.055(4) -0.016(3) -0.014(2) 0.0008(18)
C15 0.078(3) 0.066(3) 0.039(3) -0.017(3) -0.017(2) 0.010(2)
C16 0.062(2) 0.063(3) 0.035(3) -0.011(2) 0.0033(19) 0.007(2)
C17 0.0413(18) 0.051(2) 0.040(3) -0.006(2) 0.0028(16) 0.0047(15)

_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 C10 1.326(6) . ?
N1 C11 1.342(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(6) . ?
C1 C6 1.396(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.358(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(6) . ?
C6 C7 1.480(5) . ?
C7 C8 1.393(6) . ?
C7 C11 1.394(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(6) . ?
C9 C10 1.390(4) . ?
C9 C12 1.479(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.391(4) . ?
C12 C17 1.403(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(6) . ?
C17 H17 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
C10 N1 C11 116.8(2) . . ?
C2 C1 H1 119.2 . . ?
C2 C1 C6 121.6(4) . . ?
C6 C1 H1 119.2 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 122.1(4) . . ?
C5 C6 C1 117.4(4) . . ?
C5 C6 C7 120.5(3) . . ?
C8 C7 C6 123.1(3) . . ?
C8 C7 C11 116.9(4) . . ?
C11 C7 C6 119.9(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 117.3(4) . . ?
C8 C9 C12 122.8(3) . . ?
C10 C9 C12 119.9(3) . . ?
N1 C10 C9 124.6(4) . . ?
N1 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
N1 C11 C7 124.2(4) . . ?
N1 C11 H11 117.9 . . ?
C7 C11 H11 117.9 . . ?
C13 C12 C9 121.8(4) . . ?
C13 C12 C17 117.3(4) . . ?
C17 C12 C9 120.9(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.0(4) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(5) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.2(4) . . ?
C16 C17 H17 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -2.0(6) . . . . ?
C1 C6 C7 C8 -32.2(5) . . . . ?
C1 C6 C7 C11 145.6(3) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
C2 C1 C6 C7 -177.8(3) . . . . ?
C2 C3 C4 C5 2.3(6) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
C4 C5 C6 C7 178.1(3) . . . . ?
C5 C6 C7 C8 148.7(3) . . . . ?
C5 C6 C7 C11 -33.5(5) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
C6 C7 C8 C9 -180.0(3) . . . . ?
C6 C7 C11 N1 178.5(4) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C7 C8 C9 C12 179.6(3) . . . . ?
C8 C7 C11 N1 -3.5(5) . . . . ?
C8 C9 C10 N1 -1.8(5) . . . . ?
C8 C9 C12 C13 -33.0(5) . . . . ?
C8 C9 C12 C17 148.2(3) . . . . ?
C9 C12 C13 C14 -176.9(3) . . . . ?
C9 C12 C17 C16 177.9(3) . . . . ?
C10 N1 C11 C7 2.2(6) . . . . ?
C10 C9 C12 C13 146.3(3) . . . . ?
C10 C9 C12 C17 -32.5(5) . . . . ?
C11 N1 C10 C9 0.6(6) . . . . ?
C11 C7 C8 C9 2.2(6) . . . . ?
C12 C9 C10 N1 178.9(4) . . . . ?
C12 C13 C14 C15 -1.7(6) . . . . ?
C13 C12 C17 C16 -0.9(5) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C15 C16 C17 C12 -0.2(6) . . . . ?
C17 C12 C13 C14 1.9(5) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 958750'
