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

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#
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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
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_2013816hua01_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            7-hexyl-7-monoaza[6]helicene
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 N'
_chemical_formula_sum            'C29 H26 N'
_chemical_formula_weight         388.51

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   P12(1)/c1

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                   12.919(4)
_cell_length_b                   9.577(3)
_cell_length_c                   17.878(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.149(5)
_cell_angle_gamma                90.00
_cell_volume                     2208.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1932
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      22.11

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             828
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13043
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.62
_reflns_number_total             5003
_reflns_number_gt                2630
_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)+(0.1000P)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         5003
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2466
_refine_ls_wR_factor_gt          0.2129
_refine_ls_goodness_of_fit_ref   1.233
_refine_ls_restrained_S_all      1.233
_refine_ls_shift/su_max          0.524
_refine_ls_shift/su_mean         0.064

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 0.45868(17) 0.5047(2) 0.12934(14) 0.0673(7) Uani 1 1 d . . .
C1 C 0.1965(5) 0.3830(6) 0.4012(3) 0.162(2) Uani 1 1 d . . .
H1A H 0.2486 0.4540 0.4086 0.242 Uiso 1 1 calc R . .
H1B H 0.1915 0.3307 0.4467 0.242 Uiso 1 1 calc R . .
H1C H 0.1309 0.4259 0.3879 0.242 Uiso 1 1 calc R . .
C2 C 0.2234(3) 0.2942(6) 0.3443(3) 0.1383(18) Uani 1 1 d . . .
H2 H 0.2505 0.2059 0.3543 0.166 Uiso 1 1 calc R . .
C3 C 0.2063(2) 0.3479(4) 0.2654(2) 0.0961(12) Uani 1 1 d . . .
H3A H 0.2010 0.2680 0.2321 0.115 Uiso 1 1 calc R . .
H3B H 0.1399 0.3954 0.2617 0.115 Uiso 1 1 calc R . .
C4 C 0.2864(2) 0.4454(4) 0.2367(2) 0.0874(10) Uani 1 1 d . . .
H4A H 0.2823 0.5341 0.2626 0.105 Uiso 1 1 calc R . .
H4B H 0.3548 0.4067 0.2483 0.105 Uiso 1 1 calc R . .
C5 C 0.2731(2) 0.4707(4) 0.15313(19) 0.0843(10) Uani 1 1 d . . .
H5A H 0.2052 0.5112 0.1418 0.101 Uiso 1 1 calc R . .
H5B H 0.2753 0.3816 0.1275 0.101 Uiso 1 1 calc R . .
C6 C 0.3551(2) 0.5669(4) 0.1225(2) 0.0885(10) Uani 1 1 d . . .
H6A H 0.3372 0.5865 0.0701 0.106 Uiso 1 1 calc R . .
H6B H 0.3556 0.6546 0.1495 0.106 Uiso 1 1 calc R . .
C7 C 0.5301(2) 0.5251(3) 0.18702(18) 0.0657(8) Uani 1 1 d . . .
C8 C 0.61717(19) 0.4353(3) 0.17976(14) 0.0532(6) Uani 1 1 d . . .
C9 C 0.6978(2) 0.4336(3) 0.23728(14) 0.0575(7) Uani 1 1 d . . .
C10 C 0.7955(2) 0.3599(3) 0.23517(15) 0.0585(7) Uani 1 1 d . . .
C11 C 0.85075(19) 0.3349(3) 0.16745(16) 0.0593(7) Uani 1 1 d . . .
C12 C 0.9366(2) 0.2416(3) 0.1708(2) 0.0746(9) Uani 1 1 d . . .
C13 C 0.9926(2) 0.2233(4) 0.1058(3) 0.0953(12) Uani 1 1 d . . .
H13 H 1.0471 0.1598 0.1067 0.114 Uiso 1 1 calc R . .
C14 C 0.9690(2) 0.2952(5) 0.0426(2) 0.0989(13) Uani 1 1 d . . .
H14 H 1.0070 0.2806 0.0005 0.119 Uiso 1 1 calc R . .
C15 C 0.58996(18) 0.3510(3) 0.11536(13) 0.0498(6) Uani 1 1 d . . .
C16 C 0.4915(2) 0.3969(3) 0.08530(15) 0.0571(7) Uani 1 1 d . . .
C17 C 0.4412(2) 0.3357(3) 0.02346(16) 0.0678(8) Uani 1 1 d . . .
H17 H 0.3781 0.3703 0.0039 0.081 Uiso 1 1 calc R . .
C18 C 0.4868(2) 0.2228(4) -0.00812(16) 0.0728(9) Uani 1 1 d . . .
H18 H 0.4549 0.1805 -0.0502 0.087 Uiso 1 1 calc R . .
C19 C 0.5799(2) 0.1709(3) 0.02185(15) 0.0663(8) Uani 1 1 d . . .
H19 H 0.6080 0.0917 0.0007 0.080 Uiso 1 1 calc R . .
C20 C 0.63204(19) 0.2331(3) 0.08198(14) 0.0551(7) Uani 1 1 d . . .
H20 H 0.6952 0.1971 0.1005 0.066 Uiso 1 1 calc R . .
C21 C 0.6781(3) 0.5056(3) 0.30543(17) 0.0755(9) Uani 1 1 d . . .
C22 C 0.7397(3) 0.4786(5) 0.37008(19) 0.0947(12) Uani 1 1 d . . .
H22 H 0.7278 0.5284 0.4134 0.114 Uiso 1 1 calc R . .
C23 C 0.8159(3) 0.3830(5) 0.37199(19) 0.0972(13) Uani 1 1 d . . .
H23 H 0.8487 0.3573 0.4175 0.117 Uiso 1 1 calc R . .
C24 C 0.8463(2) 0.3207(4) 0.30362(18) 0.0775(9) Uani 1 1 d . . .
C25 C 0.9303(3) 0.2250(4) 0.3040(3) 0.0987(12) Uani 1 1 d . . .
H25 H 0.9581 0.1916 0.3497 0.118 Uiso 1 1 calc R . .
C26 C 0.9704(3) 0.1816(4) 0.2411(3) 0.0942(12) Uani 1 1 d . . .
H26 H 1.0206 0.1120 0.2428 0.113 Uiso 1 1 calc R . .
C27 C 0.82904(19) 0.4098(3) 0.10118(15) 0.0611(7) Uani 1 1 d . . .
H27 H 0.7742 0.4729 0.0985 0.073 Uiso 1 1 calc R . .
C28 C 0.8880(2) 0.3914(4) 0.03966(18) 0.0804(10) Uani 1 1 d . . .
H28 H 0.8736 0.4433 -0.0036 0.096 Uiso 1 1 calc R . .
C29 C 0.5908(3) 0.5962(4) 0.3077(2) 0.0916(12) Uani 1 1 d . . .
H29 H 0.5818 0.6471 0.3512 0.110 Uiso 1 1 calc R . .
C30 C 0.5217(3) 0.6111(4) 0.2503(2) 0.0912(11) Uani 1 1 d . . .
H30 H 0.4689 0.6770 0.2519 0.109 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 C7 1.359(4) . ?
N1 C16 1.380(3) . ?
N1 C6 1.463(3) . ?
C1 C2 1.385(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.506(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.505(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.515(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.529(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C30 1.408(4) . ?
C7 C8 1.428(4) . ?
C8 C9 1.423(4) . ?
C8 C15 1.434(3) . ?
C9 C21 1.435(4) . ?
C9 C10 1.448(4) . ?
C10 C24 1.407(4) . ?
C10 C11 1.459(4) . ?
C11 C12 1.422(4) . ?
C11 C27 1.401(4) . ?
C12 C13 1.413(5) . ?
C12 C26 1.428(5) . ?
C13 C14 1.344(5) . ?
C13 H13 0.9300 . ?
C14 C28 1.393(5) . ?
C14 H14 0.9300 . ?
C15 C20 1.401(3) . ?
C15 C16 1.422(3) . ?
C16 C17 1.382(4) . ?
C17 C18 1.368(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.391(5) . ?
C21 C29 1.426(5) . ?
C22 C23 1.342(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.434(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.420(5) . ?
C25 C26 1.331(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.383(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.331(5) . ?
C29 H29 0.9300 . ?
C30 H30 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
C7 N1 C16 108.9(2) . . ?
C7 N1 C6 125.8(3) . . ?
C16 N1 C6 124.4(3) . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 116.7(5) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.7 . . ?
C4 C3 C2 117.6(4) . . ?
C4 C3 H3A 107.9 . . ?
C2 C3 H3A 108.0 . . ?
C4 C3 H3B 107.9 . . ?
C2 C3 H3B 107.9 . . ?
H3A C3 H3B 107.2 . . ?
C5 C4 C3 113.1(3) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 C6 114.0(3) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C5 111.9(2) . . ?
N1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N1 C7 C30 127.9(3) . . ?
N1 C7 C8 110.5(2) . . ?
C30 C7 C8 121.4(3) . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 C15 135.3(2) . . ?
C7 C8 C15 104.6(2) . . ?
C8 C9 C21 116.8(3) . . ?
C8 C9 C10 126.2(2) . . ?
C21 C9 C10 116.9(3) . . ?
C24 C10 C9 118.2(3) . . ?
C24 C10 C11 116.9(3) . . ?
C9 C10 C11 124.6(2) . . ?
C12 C11 C27 118.5(3) . . ?
C12 C11 C10 119.0(3) . . ?
C27 C11 C10 122.2(3) . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 C26 121.9(3) . . ?
C11 C12 C26 119.3(3) . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C28 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C28 C14 H14 119.8 . . ?
C20 C15 C16 116.6(2) . . ?
C20 C15 C8 135.4(2) . . ?
C16 C15 C8 107.7(2) . . ?
C17 C16 N1 128.9(3) . . ?
C17 C16 C15 122.9(3) . . ?
N1 C16 C15 108.2(2) . . ?
C16 C17 C18 118.1(3) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 121.8(3) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C15 C20 C19 119.9(2) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C29 120.5(3) . . ?
C22 C21 C9 119.7(3) . . ?
C29 C21 C9 119.6(3) . . ?
C23 C22 C21 122.2(3) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 119.8(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C10 C24 C25 119.8(3) . . ?
C10 C24 C23 119.6(4) . . ?
C25 C24 C23 120.6(4) . . ?
C26 C25 C24 122.0(4) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C25 C26 C12 120.3(4) . . ?
C25 C26 H26 119.9 . . ?
C12 C26 H26 119.8 . . ?
C28 C27 C11 120.9(3) . . ?
C28 C27 H27 119.5 . . ?
C11 C27 H27 119.5 . . ?
C27 C28 C14 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C14 C28 H28 120.0 . . ?
C30 C29 C21 122.8(3) . . ?
C30 C29 H29 118.6 . . ?
C21 C29 H29 118.6 . . ?
C29 C30 C7 118.6(3) . . ?
C29 C30 H30 120.7 . . ?
C7 C30 H30 120.7 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.053
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.062
;
_database_code_depnum_ccdc_archive 'CCDC 991300'
