# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1032257'
_audit_update_record             
;
2014-11-01 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'1-(2-Cyano-phenyl)-3-piperidine-1-yl-4,5-dihydro-1H-benz[e]indene-1,2-dicarbonitrile '
_chemical_name_common            indene
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 N4'
_chemical_formula_weight         402.49

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                   9.1440(5)
_cell_length_b                   10.7523(6)
_cell_length_c                   12.0332(7)
_cell_angle_alpha                66.569(5)
_cell_angle_beta                 88.615(5)
_cell_angle_gamma                88.295(5)
_cell_volume                     1084.96(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       crystalline
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.074
_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            16477
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         29.15
_reflns_number_total             5193
_reflns_number_gt                4007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0551P)²+0.1846P] 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         5193
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.26413(13) 0.27862(11) 0.40877(10) 0.0405(3) Uani 1 1 d . . .
C9 C 0.29867(13) 0.05869(12) 0.58747(11) 0.0321(3) Uani 1 1 d . . .
C12 C 0.32734(14) 0.25862(12) 0.61210(11) 0.0337(3) Uani 1 1 d . . .
C11 C 0.29184(13) 0.20864(13) 0.52743(11) 0.0323(3) Uani 1 1 d . . .
C19 C 0.24306(14) 0.15783(12) 0.82974(11) 0.0330(3) Uani 1 1 d . . .
C4 C 0.34340(15) -0.16161(14) 0.91633(12) 0.0400(3) Uani 1 1 d . . .
H4 H 0.3433 -0.0965 0.9491 0.048 Uiso 1 1 calc R . .
C5 C 0.34156(13) -0.12126(12) 0.79079(11) 0.0323(3) Uani 1 1 d . . .
C10 C 0.33071(13) 0.01981(12) 0.70519(11) 0.0307(3) Uani 1 1 d . . .
C6 C 0.34666(14) -0.22029(13) 0.74172(13) 0.0374(3) Uani 1 1 d . . .
N2 N 0.62133(15) 0.13923(16) 0.80299(14) 0.0629(4) Uani 1 1 d . . .
C18 C 0.29199(17) 0.19006(17) 0.92257(14) 0.0501(4) Uani 1 1 d . . .
H18 H 0.3917 0.1990 0.9300 0.060 Uiso 1 1 calc R . .
C13 C 0.35022(13) 0.14305(12) 0.73519(11) 0.0318(3) Uani 1 1 d . . .
C15 C -0.00442(16) 0.16530(14) 0.90508(13) 0.0447(3) Uani 1 1 d . . .
H15 H -0.1045 0.1568 0.8988 0.054 Uiso 1 1 calc R . .
N3 N 0.3310(2) 0.49862(14) 0.60498(15) 0.0759(5) Uani 1 1 d . . .
C7 C 0.35941(18) -0.17540(14) 0.60679(13) 0.0476(4) Uani 1 1 d . . .
H7A H 0.3239 -0.2467 0.5850 0.057 Uiso 1 1 calc R . .
H7B H 0.4620 -0.1633 0.5834 0.057 Uiso 1 1 calc R . .
C14 C 0.09163(14) 0.14565(13) 0.82190(12) 0.0361(3) Uani 1 1 d . . .
C3 C 0.34534(17) -0.29744(15) 0.99214(14) 0.0490(4) Uani 1 1 d . . .
H3 H 0.3466 -0.3235 1.0757 0.059 Uiso 1 1 calc R . .
C8 C 0.27575(17) -0.04480(14) 0.53538(12) 0.0423(3) Uani 1 1 d . . .
H8A H 0.3088 -0.0095 0.4515 0.051 Uiso 1 1 calc R . .
H8B H 0.1723 -0.0631 0.5374 0.051 Uiso 1 1 calc R . .
C22 C 0.50356(15) 0.14034(14) 0.77402(13) 0.0402(3) Uani 1 1 d . . .
C24 C 0.1581(2) 0.23516(17) 0.34278(15) 0.0597(5) Uani 1 1 d . . .
H24A H 0.1355 0.1407 0.3890 0.072 Uiso 1 1 calc R . .
H24B H 0.2006 0.2430 0.2657 0.072 Uiso 1 1 calc R . .
C20 C 0.32886(17) 0.39254(14) 0.60427(13) 0.0448(3) Uani 1 1 d . . .
C17 C 0.1948(2) 0.20937(19) 1.00493(15) 0.0622(5) Uani 1 1 d . . .
H17 H 0.2304 0.2309 1.0667 0.075 Uiso 1 1 calc R . .
C16 C 0.04756(19) 0.19726(16) 0.99662(14) 0.0536(4) Uani 1 1 d . . .
H16 H -0.0168 0.2105 1.0522 0.064 Uiso 1 1 calc R . .
C21 C 0.02652(15) 0.11196(18) 0.72983(15) 0.0505(4) Uani 1 1 d . . .
C23 C 0.29601(17) 0.42278(15) 0.34757(13) 0.0478(4) Uani 1 1 d . . .
H23A H 0.3410 0.4396 0.2692 0.057 Uiso 1 1 calc R . .
H23B H 0.3653 0.4470 0.3951 0.057 Uiso 1 1 calc R . .
N4 N -0.03157(17) 0.0838(2) 0.66074(16) 0.0863(6) Uani 1 1 d . . .
C2 C 0.34722(17) -0.35603(14) 0.81973(15) 0.0487(4) Uani 1 1 d . . .
H2 H 0.3489 -0.4222 0.7881 0.058 Uiso 1 1 calc R . .
C1 C 0.34538(18) -0.39444(15) 0.94410(15) 0.0532(4) Uani 1 1 d . . .
H1 H 0.3442 -0.4859 0.9953 0.064 Uiso 1 1 calc R . .
C27 C 0.1597(2) 0.51064(17) 0.33016(18) 0.0668(5) Uani 1 1 d . . .
H27A H 0.1842 0.6051 0.2866 0.080 Uiso 1 1 calc R . .
H27B H 0.1186 0.4999 0.4085 0.080 Uiso 1 1 calc R . .
C25 C 0.0197(2) 0.31994(19) 0.32115(19) 0.0776(6) Uani 1 1 d . . .
H25A H -0.0300 0.3012 0.3981 0.093 Uiso 1 1 calc R . .
H25B H -0.0445 0.2945 0.2710 0.093 Uiso 1 1 calc R . .
C26 C 0.0480(2) 0.4711(2) 0.2596(2) 0.0828(6) Uani 1 1 d . . .
H26A H 0.0840 0.4929 0.1777 0.099 Uiso 1 1 calc R . .
H26B H -0.0427 0.5219 0.2553 0.099 Uiso 1 1 calc R . .


_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 C11 1.3493(16) . ?
N1 C23 1.4624(17) . ?
N1 C24 1.4657(18) . ?
C9 C10 1.3450(17) . ?
C9 C11 1.4816(17) . ?
C9 C8 1.5000(16) . ?
C12 C11 1.3763(17) . ?
C12 C20 1.4056(18) . ?
C12 C13 1.5224(18) . ?
C19 C18 1.3818(17) . ?
C19 C14 1.4037(18) . ?
C19 C13 1.5364(18) . ?
C4 C3 1.380(2) . ?
C4 C5 1.3964(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.4072(17) . ?
C5 C10 1.4578(17) . ?
C10 C13 1.5217(16) . ?
C6 C2 1.3862(19) . ?
C6 C7 1.501(2) . ?
N2 C22 1.1382(18) . ?
C18 C17 1.388(2) . ?
C18 H18 0.9300 . ?
C13 C22 1.4844(18) . ?
C15 C16 1.376(2) . ?
C15 C14 1.3901(19) . ?
C15 H15 0.9300 . ?
N3 C20 1.1448(18) . ?
C7 C8 1.518(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C21 1.4412(19) . ?
C3 C1 1.379(2) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C24 C25 1.503(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C17 C16 1.366(2) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C21 N4 1.1386(19) . ?
C23 C27 1.508(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C2 C1 1.385(2) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C27 C26 1.517(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C25 C26 1.522(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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
C11 N1 C23 121.56(11) . . ?
C11 N1 C24 122.95(12) . . ?
C23 N1 C24 112.26(11) . . ?
C10 C9 C11 109.95(10) . . ?
C10 C9 C8 120.55(12) . . ?
C11 C9 C8 129.50(11) . . ?
C11 C12 C20 130.62(13) . . ?
C11 C12 C13 110.40(10) . . ?
C20 C12 C13 118.56(11) . . ?
N1 C11 C12 128.15(12) . . ?
N1 C11 C9 124.14(11) . . ?
C12 C11 C9 107.59(11) . . ?
C18 C19 C14 117.51(12) . . ?
C18 C19 C13 120.97(12) . . ?
C14 C19 C13 121.45(10) . . ?
C3 C4 C5 120.47(13) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.47(12) . . ?
C4 C5 C10 123.67(11) . . ?
C6 C5 C10 116.84(11) . . ?
C9 C10 C5 123.87(11) . . ?
C9 C10 C13 110.42(11) . . ?
C5 C10 C13 125.70(11) . . ?
C2 C6 C5 118.94(13) . . ?
C2 C6 C7 122.17(12) . . ?
C5 C6 C7 118.81(12) . . ?
C19 C18 C17 121.11(14) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C22 C13 C10 107.83(10) . . ?
C22 C13 C12 110.03(10) . . ?
C10 C13 C12 101.52(9) . . ?
C22 C13 C19 110.42(10) . . ?
C10 C13 C19 116.06(10) . . ?
C12 C13 C19 110.57(10) . . ?
C16 C15 C14 120.44(14) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C6 C7 C8 114.19(11) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C15 C14 C19 120.73(12) . . ?
C15 C14 C21 116.22(12) . . ?
C19 C14 C21 123.05(12) . . ?
C1 C3 C4 120.03(14) . . ?
C1 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C9 C8 C7 110.60(11) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N2 C22 C13 179.44(18) . . ?
N1 C24 C25 111.02(14) . . ?
N1 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
N1 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
N3 C20 C12 176.05(17) . . ?
C16 C17 C18 120.97(14) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C16 C15 119.24(14) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
N4 C21 C14 176.35(16) . . ?
N1 C23 C27 111.85(12) . . ?
N1 C23 H23A 109.2 . . ?
C27 C23 H23A 109.2 . . ?
N1 C23 H23B 109.2 . . ?
C27 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C1 C2 C6 120.88(14) . . ?
C1 C2 H2 119.6 . . ?
C6 C2 H2 119.6 . . ?
C3 C1 C2 120.15(14) . . ?
C3 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C23 C27 C26 110.03(16) . . ?
C23 C27 H27A 109.7 . . ?
C26 C27 H27A 109.7 . . ?
C23 C27 H27B 109.7 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C24 C25 C26 112.53(16) . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C27 C26 C25 110.03(15) . . ?
C27 C26 H26A 109.7 . . ?
C25 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
C25 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?

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
C23 N1 C11 C12 11.9(2) . . . . ?
C24 N1 C11 C12 -146.21(15) . . . . ?
C23 N1 C11 C9 -163.64(12) . . . . ?
C24 N1 C11 C9 38.2(2) . . . . ?
C20 C12 C11 N1 8.1(2) . . . . ?
C13 C12 C11 N1 -179.68(12) . . . . ?
C20 C12 C11 C9 -175.81(14) . . . . ?
C13 C12 C11 C9 -3.55(14) . . . . ?
C10 C9 C11 N1 178.94(12) . . . . ?
C8 C9 C11 N1 -1.0(2) . . . . ?
C10 C9 C11 C12 2.62(14) . . . . ?
C8 C9 C11 C12 -177.35(13) . . . . ?
C3 C4 C5 C6 -2.1(2) . . . . ?
C3 C4 C5 C10 176.22(12) . . . . ?
C11 C9 C10 C5 178.24(11) . . . . ?
C8 C9 C10 C5 -1.80(19) . . . . ?
C11 C9 C10 C13 -0.57(14) . . . . ?
C8 C9 C10 C13 179.39(11) . . . . ?
C4 C5 C10 C9 -165.69(12) . . . . ?
C6 C5 C10 C9 12.69(18) . . . . ?
C4 C5 C10 C13 12.94(19) . . . . ?
C6 C5 C10 C13 -168.68(11) . . . . ?
C4 C5 C6 C2 2.67(19) . . . . ?
C10 C5 C6 C2 -175.78(12) . . . . ?
C4 C5 C6 C7 -174.10(12) . . . . ?
C10 C5 C6 C7 7.44(18) . . . . ?
C14 C19 C18 C17 0.1(2) . . . . ?
C13 C19 C18 C17 177.12(14) . . . . ?
C9 C10 C13 C22 -117.09(12) . . . . ?
C5 C10 C13 C22 64.13(15) . . . . ?
C9 C10 C13 C12 -1.44(13) . . . . ?
C5 C10 C13 C12 179.78(11) . . . . ?
C9 C10 C13 C19 118.49(12) . . . . ?
C5 C10 C13 C19 -60.30(16) . . . . ?
C11 C12 C13 C22 117.11(12) . . . . ?
C20 C12 C13 C22 -69.58(15) . . . . ?
C11 C12 C13 C10 3.10(13) . . . . ?
C20 C12 C13 C10 176.41(12) . . . . ?
C11 C12 C13 C19 -120.64(11) . . . . ?
C20 C12 C13 C19 52.67(15) . . . . ?
C18 C19 C13 C22 11.33(17) . . . . ?
C14 C19 C13 C22 -171.78(12) . . . . ?
C18 C19 C13 C10 134.41(13) . . . . ?
C14 C19 C13 C10 -48.70(16) . . . . ?
C18 C19 C13 C12 -110.69(14) . . . . ?
C14 C19 C13 C12 66.20(15) . . . . ?
C2 C6 C7 C8 146.98(13) . . . . ?
C5 C6 C7 C8 -36.35(18) . . . . ?
C16 C15 C14 C19 0.1(2) . . . . ?
C16 C15 C14 C21 179.73(14) . . . . ?
C18 C19 C14 C15 -0.1(2) . . . . ?
C13 C19 C14 C15 -177.10(12) . . . . ?
C18 C19 C14 C21 -179.73(14) . . . . ?
C13 C19 C14 C21 3.3(2) . . . . ?
C5 C4 C3 C1 0.0(2) . . . . ?
C10 C9 C8 C7 -26.71(18) . . . . ?
C11 C9 C8 C7 153.25(13) . . . . ?
C6 C7 C8 C9 44.19(17) . . . . ?
C10 C13 C22 N2 117(18) . . . . ?
C12 C13 C22 N2 7(18) . . . . ?
C19 C13 C22 N2 -116(18) . . . . ?
C11 N1 C24 C25 104.48(16) . . . . ?
C23 N1 C24 C25 -55.45(19) . . . . ?
C11 C12 C20 N3 169(3) . . . . ?
C13 C12 C20 N3 -3(3) . . . . ?
C19 C18 C17 C16 -0.1(3) . . . . ?
C18 C17 C16 C15 0.1(3) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C15 C14 C21 N4 -16(3) . . . . ?
C19 C14 C21 N4 164(3) . . . . ?
C11 N1 C23 C27 -102.18(16) . . . . ?
C24 N1 C23 C27 58.07(18) . . . . ?
C5 C6 C2 C1 -1.1(2) . . . . ?
C7 C6 C2 C1 175.55(14) . . . . ?
C4 C3 C1 C2 1.6(2) . . . . ?
C6 C2 C1 C3 -1.1(2) . . . . ?
N1 C23 C27 C26 -57.05(18) . . . . ?
N1 C24 C25 C26 53.5(2) . . . . ?
C23 C27 C26 C25 54.0(2) . . . . ?
C24 C25 C26 C27 -53.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ss-163g-
_database_code_depnum_ccdc_archive 'CCDC 1046947'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 N4'
_chemical_formula_weight         404.50

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                   8.972(3)
_cell_length_b                   9.172(2)
_cell_length_c                   14.034(2)
_cell_angle_alpha                90.632(16)
_cell_angle_beta                 105.367(18)
_cell_angle_gamma                104.96(2)
_cell_volume                     1072.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       crystalline
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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            13571
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_av_sigmaI/netI    0.1824
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         29.17
_reflns_number_total             5060
_reflns_number_gt                1673
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0938P)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         5060
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2752
_refine_ls_R_factor_gt           0.1020
_refine_ls_wR_factor_ref         0.3020
_refine_ls_wR_factor_gt          0.2142
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.005

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 0.1186(5) 0.2146(5) 0.8520(3) 0.0659(12) Uani 1 1 d . . .
C19 C -0.1042(5) 0.4551(6) 0.6887(3) 0.0543(13) Uani 1 1 d . . .
H19 H -0.1341 0.4774 0.6192 0.065 Uiso 1 1 calc R . .
C17 C -0.3651(5) 0.2402(6) 0.6164(3) 0.0523(12) Uani 1 1 d . . .
C18 C -0.2047(5) 0.2919(6) 0.6918(3) 0.0506(12) Uani 1 1 d . . .
C9 C -0.1584(5) 0.2025(6) 0.7594(3) 0.0515(12) Uani 1 1 d . . .
C21 C 0.0777(5) 0.4842(6) 0.7184(3) 0.0514(12) Uani 1 1 d . . .
C22 C 0.1759(6) 0.5679(6) 0.8062(3) 0.0607(14) Uani 1 1 d . . .
H22 H 0.1306 0.6100 0.8482 0.073 Uiso 1 1 calc R . .
C6 C -0.0189(6) 0.2475(5) 0.8510(3) 0.0547(13) Uani 1 1 d . . .
C26 C 0.1515(6) 0.4297(6) 0.6569(3) 0.0588(13) Uani 1 1 d . . .
N3 N -0.1909(5) 0.6484(6) 0.7853(4) 0.0904(17) Uani 1 1 d . . .
C20 C -0.1520(5) 0.5667(6) 0.7449(4) 0.0645(14) Uani 1 1 d . . .
N2 N -0.3163(6) 0.3562(6) 0.9276(3) 0.0860(16) Uani 1 1 d . . .
C7 C -0.0453(5) 0.3140(5) 0.9302(3) 0.0593(14) Uani 1 1 d . . .
H7 H 0.0379 0.3441 0.9883 0.071 Uiso 1 1 calc R . .
C2 C 0.1503(7) -0.0332(7) 0.8159(4) 0.0864(18) Uani 1 1 d . . .
H2A H 0.1718 -0.0940 0.7668 0.104 Uiso 1 1 calc R . .
H2B H 0.0497 -0.0880 0.8277 0.104 Uiso 1 1 calc R . .
C10 C -0.2641(7) 0.0435(6) 0.7571(3) 0.0762(16) Uani 1 1 d . . .
H10A H -0.2453 -0.0231 0.7100 0.091 Uiso 1 1 calc R . .
H10B H -0.2364 0.0062 0.8221 0.091 Uiso 1 1 calc R . .
C12 C -0.4809(6) 0.1196(7) 0.6354(3) 0.0655(15) Uani 1 1 d . . .
N4 N -0.0224(6) 0.2819(6) 0.4863(3) 0.0999(18) Uani 1 1 d . . .
C1 C 0.1339(6) 0.1136(6) 0.7761(3) 0.0740(16) Uani 1 1 d . . .
H1A H 0.2274 0.1614 0.7541 0.089 Uiso 1 1 calc R . .
H1B H 0.0399 0.0952 0.7194 0.089 Uiso 1 1 calc R . .
C24 C 0.4101(6) 0.5320(7) 0.7703(5) 0.0850(18) Uani 1 1 d . . .
H24 H 0.5208 0.5470 0.7889 0.102 Uiso 1 1 calc R . .
C25 C 0.3184(6) 0.4528(7) 0.6819(4) 0.0741(16) Uani 1 1 d . . .
H25 H 0.3658 0.4152 0.6393 0.089 Uiso 1 1 calc R . .
C23 C 0.3386(6) 0.5887(7) 0.8313(4) 0.0775(17) Uani 1 1 d . . .
H23 H 0.4018 0.6427 0.8911 0.093 Uiso 1 1 calc R . .
C16 C -0.4070(6) 0.3121(6) 0.5304(3) 0.0692(15) Uani 1 1 d . . .
H16 H -0.3305 0.3916 0.5158 0.083 Uiso 1 1 calc R . .
C11 C -0.4379(6) 0.0412(7) 0.7282(4) 0.0820(17) Uani 1 1 d . . .
H11A H -0.4609 0.0909 0.7818 0.098 Uiso 1 1 calc R . .
H11B H -0.5034 -0.0630 0.7175 0.098 Uiso 1 1 calc R . .
C8 C -0.1950(6) 0.3380(6) 0.9257(3) 0.0625(15) Uani 1 1 d . . .
C27 C 0.0519(6) 0.3463(7) 0.5613(4) 0.0720(16) Uani 1 1 d . . .
C15 C -0.5602(8) 0.2676(8) 0.4662(4) 0.0852(19) Uani 1 1 d . . .
H15 H -0.5853 0.3163 0.4086 0.102 Uiso 1 1 calc R . .
C4 C 0.2681(7) 0.0983(8) 0.9857(4) 0.0906(19) Uani 1 1 d . . .
H4A H 0.1725 0.0556 1.0069 0.109 Uiso 1 1 calc R . .
H4B H 0.3604 0.1172 1.0436 0.109 Uiso 1 1 calc R . .
C5 C 0.2581(7) 0.2432(7) 0.9413(4) 0.0878(19) Uani 1 1 d . . .
H5A H 0.2467 0.3133 0.9894 0.105 Uiso 1 1 calc R . .
H5B H 0.3560 0.2886 0.9232 0.105 Uiso 1 1 calc R . .
C14 C -0.6734(7) 0.1533(9) 0.4871(4) 0.089(2) Uani 1 1 d . . .
H14 H -0.7774 0.1262 0.4451 0.107 Uiso 1 1 calc R . .
C13 C -0.6360(6) 0.0769(7) 0.5700(4) 0.0833(19) Uani 1 1 d . . .
H13 H -0.7138 -0.0034 0.5828 0.100 Uiso 1 1 calc R . .
C3 C 0.2833(7) -0.0120(7) 0.9113(5) 0.0920(19) Uani 1 1 d . . .
H3A H 0.2798 -0.1089 0.9389 0.110 Uiso 1 1 calc R . .
H3B H 0.3862 0.0248 0.8973 0.110 Uiso 1 1 calc R . .


_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 C6 1.340(5) . ?
N1 C1 1.461(5) . ?
N1 C5 1.482(5) . ?
C19 C20 1.497(7) . ?
C19 C21 1.523(6) . ?
C19 C18 1.543(6) . ?
C17 C12 1.391(7) . ?
C17 C16 1.392(6) . ?
C17 C18 1.498(6) . ?
C18 C9 1.315(6) . ?
C9 C6 1.503(6) . ?
C9 C10 1.515(7) . ?
C21 C26 1.379(6) . ?
C21 C22 1.392(6) . ?
C22 C23 1.369(6) . ?
C6 C7 1.365(5) . ?
C26 C25 1.402(6) . ?
C26 C27 1.474(7) . ?
N3 C20 1.112(5) . ?
N2 C8 1.149(5) . ?
C7 C8 1.402(6) . ?
C2 C1 1.491(7) . ?
C2 C3 1.510(7) . ?
C10 C11 1.498(7) . ?
C12 C13 1.402(6) . ?
C12 C11 1.503(7) . ?
N4 C27 1.146(6) . ?
C24 C23 1.366(7) . ?
C24 C25 1.369(7) . ?
C16 C15 1.383(7) . ?
C15 C14 1.355(8) . ?
C4 C5 1.488(8) . ?
C4 C3 1.503(7) . ?
C14 C13 1.375(8) . ?

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
C6 N1 C1 123.6(4) . . ?
C6 N1 C5 123.2(4) . . ?
C1 N1 C5 111.5(4) . . ?
C20 C19 C21 110.5(4) . . ?
C20 C19 C18 111.2(4) . . ?
C21 C19 C18 117.2(4) . . ?
C12 C17 C16 118.1(4) . . ?
C12 C17 C18 118.6(4) . . ?
C16 C17 C18 123.1(5) . . ?
C9 C18 C17 120.2(5) . . ?
C9 C18 C19 122.9(4) . . ?
C17 C18 C19 116.8(4) . . ?
C18 C9 C6 126.4(5) . . ?
C18 C9 C10 119.6(4) . . ?
C6 C9 C10 113.4(4) . . ?
C26 C21 C22 117.3(4) . . ?
C26 C21 C19 120.2(4) . . ?
C22 C21 C19 122.4(4) . . ?
C23 C22 C21 120.6(4) . . ?
N1 C6 C7 124.3(4) . . ?
N1 C6 C9 119.3(4) . . ?
C7 C6 C9 116.4(4) . . ?
C21 C26 C25 122.0(4) . . ?
C21 C26 C27 118.9(4) . . ?
C25 C26 C27 119.1(4) . . ?
N3 C20 C19 178.4(5) . . ?
C6 C7 C8 121.4(4) . . ?
C1 C2 C3 112.4(5) . . ?
C11 C10 C9 110.8(4) . . ?
C17 C12 C13 119.8(5) . . ?
C17 C12 C11 118.8(4) . . ?
C13 C12 C11 121.3(5) . . ?
N1 C1 C2 110.6(4) . . ?
C23 C24 C25 119.8(5) . . ?
C24 C25 C26 118.7(5) . . ?
C24 C23 C22 121.4(5) . . ?
C15 C16 C17 121.4(6) . . ?
C10 C11 C12 111.5(4) . . ?
N2 C8 C7 176.1(5) . . ?
N4 C27 C26 178.5(6) . . ?
C14 C15 C16 119.9(6) . . ?
C5 C4 C3 110.1(5) . . ?
N1 C5 C4 109.8(5) . . ?
C15 C14 C13 120.5(6) . . ?
C14 C13 C12 120.2(6) . . ?
C4 C3 C2 111.4(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
C12 C17 C18 C9 18.6(6) . . . . ?
C16 C17 C18 C9 -164.9(4) . . . . ?
C12 C17 C18 C19 -158.3(4) . . . . ?
C16 C17 C18 C19 18.2(6) . . . . ?
C20 C19 C18 C9 -92.5(5) . . . . ?
C21 C19 C18 C9 35.9(6) . . . . ?
C20 C19 C18 C17 84.3(4) . . . . ?
C21 C19 C18 C17 -147.3(4) . . . . ?
C17 C18 C9 C6 -166.9(4) . . . . ?
C19 C18 C9 C6 9.8(7) . . . . ?
C17 C18 C9 C10 3.4(6) . . . . ?
C19 C18 C9 C10 -179.9(4) . . . . ?
C20 C19 C21 C26 -159.7(4) . . . . ?
C18 C19 C21 C26 71.6(5) . . . . ?
C20 C19 C21 C22 19.1(6) . . . . ?
C18 C19 C21 C22 -109.6(5) . . . . ?
C26 C21 C22 C23 -2.7(7) . . . . ?
C19 C21 C22 C23 178.5(5) . . . . ?
C1 N1 C6 C7 165.4(5) . . . . ?
C5 N1 C6 C7 1.7(8) . . . . ?
C1 N1 C6 C9 -11.3(7) . . . . ?
C5 N1 C6 C9 -174.9(5) . . . . ?
C18 C9 C6 N1 -101.6(5) . . . . ?
C10 C9 C6 N1 87.6(5) . . . . ?
C18 C9 C6 C7 81.5(6) . . . . ?
C10 C9 C6 C7 -89.4(5) . . . . ?
C22 C21 C26 C25 1.8(7) . . . . ?
C19 C21 C26 C25 -179.4(4) . . . . ?
C22 C21 C26 C27 -177.4(5) . . . . ?
C19 C21 C26 C27 1.4(7) . . . . ?
C21 C19 C20 N3 172(100) . . . . ?
C18 C19 C20 N3 -56(22) . . . . ?
N1 C6 C7 C8 -176.5(5) . . . . ?
C9 C6 C7 C8 0.2(7) . . . . ?
C18 C9 C10 C11 -38.3(6) . . . . ?
C6 C9 C10 C11 133.3(4) . . . . ?
C16 C17 C12 C13 -1.8(7) . . . . ?
C18 C17 C12 C13 174.8(4) . . . . ?
C16 C17 C12 C11 -179.7(4) . . . . ?
C18 C17 C12 C11 -3.0(6) . . . . ?
C6 N1 C1 C2 -107.4(5) . . . . ?
C5 N1 C1 C2 57.9(6) . . . . ?
C3 C2 C1 N1 -52.8(6) . . . . ?
C23 C24 C25 C26 -1.1(9) . . . . ?
C21 C26 C25 C24 0.1(8) . . . . ?
C27 C26 C25 C24 179.2(5) . . . . ?
C25 C24 C23 C22 0.3(9) . . . . ?
C21 C22 C23 C24 1.7(9) . . . . ?
C12 C17 C16 C15 1.3(7) . . . . ?
C18 C17 C16 C15 -175.3(4) . . . . ?
C9 C10 C11 C12 50.5(6) . . . . ?
C17 C12 C11 C10 -31.6(6) . . . . ?
C13 C12 C11 C10 150.6(5) . . . . ?
C6 C7 C8 N2 146(8) . . . . ?
C21 C26 C27 N4 164(23) . . . . ?
C25 C26 C27 N4 -15(24) . . . . ?
C17 C16 C15 C14 0.9(8) . . . . ?
C6 N1 C5 C4 104.0(5) . . . . ?
C1 N1 C5 C4 -61.4(6) . . . . ?
C3 C4 C5 N1 58.5(6) . . . . ?
C16 C15 C14 C13 -2.4(8) . . . . ?
C15 C14 C13 C12 1.8(8) . . . . ?
C17 C12 C13 C14 0.4(7) . . . . ?
C11 C12 C13 C14 178.2(5) . . . . ?
C5 C4 C3 C2 -53.8(7) . . . . ?
C1 C2 C3 C4 51.2(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.0
_diffrn_reflns_theta_full        29.17
_diffrn_measured_fraction_theta_full 1.0
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.069
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    Heat-sensitive
