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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p21c

_audit_creation_date             2014-06-03T15:43:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        1,6-di(1H-indol-1-yl)hexa-2,4-diyne
;
_chemical_name_common            1,6-di(1H-indol-1-yl)hexa-2,4-diyne
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
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                   14.3639(5)
_cell_length_b                   11.0764(4)
_cell_length_c                   10.2050(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.722(2)
_cell_angle_gamma                90
_cell_volume                     1604.84(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    189(2)
_cell_measurement_reflns_used    3731
_cell_measurement_theta_min      2.731
_cell_measurement_theta_max      25.254

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_T_max  0.9918

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      189(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_number            22096
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         27.33
_diffrn_reflns_theta_full        27.33
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_reflns_number_total             3573
_reflns_number_gt                2423
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0447P)²+0.4967P] where P=(Fo²+2Fc²)/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       none
_refine_ls_number_reflns         3573
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.118
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.06299(9) 0.32636(12) 0.99426(13) 0.0329(3) Uani 1 1 d . . .
N2 N 0.51150(10) 0.00921(13) 0.70821(14) 0.0385(4) Uani 1 1 d . . .
C11 C -0.04018(16) 0.51773(17) 0.66192(19) 0.0496(5) Uani 1 1 d . . .
H11 H -0.0669 0.5628 0.5863 0.06 Uiso 1 1 calc R . .
C10 C -0.09895(13) 0.45455(17) 0.73214(18) 0.0460(5) Uani 1 1 d . . .
H10 H -0.1652 0.4546 0.7048 0.055 Uiso 1 1 calc R . .
C9 C -0.05852(11) 0.38994(15) 0.84523(17) 0.0346(4) Uani 1 1 d . . .
C14 C 0.03935(11) 0.39221(14) 0.88008(15) 0.0287(3) Uani 1 1 d . . .
C1 C 0.15729(12) 0.31097(17) 1.06567(17) 0.0419(4) Uani 1 1 d . . .
H1A H 0.1538 0.2676 1.1496 0.05 Uiso 1 1 calc R . .
H1B H 0.1852 0.3914 1.0884 0.05 Uiso 1 1 calc R . .
C2 C 0.21899(12) 0.24336(16) 0.98880(16) 0.0379(4) Uani 1 1 d . . .
C3 C 0.26733(11) 0.18924(15) 0.92350(17) 0.0352(4) Uani 1 1 d . . .
C4 C 0.32003(11) 0.12247(15) 0.84692(17) 0.0345(4) Uani 1 1 d . . .
C5 C 0.36216(11) 0.06166(16) 0.77911(17) 0.0359(4) Uani 1 1 d . . .
C6 C 0.41174(12) -0.01772(17) 0.69664(19) 0.0419(4) Uani 1 1 d . . .
H6A H 0.4038 -0.1027 0.7231 0.05 Uiso 1 1 calc R . .
H6B H 0.3826 -0.0092 0.6028 0.05 Uiso 1 1 calc R . .
C22 C 0.55114(11) 0.10216(15) 0.64621(16) 0.0321(4) Uani 1 1 d . . .
C17 C 0.64832(11) 0.10328(16) 0.69274(16) 0.0355(4) Uani 1 1 d . . .
C18 C 0.70444(12) 0.19115(16) 0.64439(18) 0.0401(4) Uani 1 1 d . . .
H18 H 0.7702 0.1946 0.6754 0.048 Uiso 1 1 calc R . .
C19 C 0.66336(13) 0.27193(17) 0.55206(19) 0.0440(5) Uani 1 1 d . . .
H19 H 0.7012 0.3317 0.5191 0.053 Uiso 1 1 calc R . .
C8 C -0.09368(13) 0.31873(16) 0.94423(19) 0.0434(5) Uani 1 1 d . . .
H8 H -0.1578 0.2999 0.9477 0.052 Uiso 1 1 calc R . .
C7 C -0.01863(13) 0.28337(15) 1.03168(18) 0.0406(4) Uani 1 1 d . . .
H7 H -0.0218 0.2356 1.1082 0.049 Uiso 1 1 calc R . .
C13 C 0.09802(13) 0.45547(15) 0.80669(17) 0.0385(4) Uani 1 1 d . . .
H13 H 0.1645 0.4552 0.8315 0.046 Uiso 1 1 calc R . .
C12 C 0.05635(15) 0.51754(16) 0.69819(19) 0.0474(5) Uani 1 1 d . . .
H12 H 0.0945 0.5615 0.6465 0.057 Uiso 1 1 calc R . .
C15 C 0.58208(13) -0.04705(17) 0.79270(19) 0.0435(5) Uani 1 1 d . . .
H15 H 0.5733 -0.1139 0.8479 0.052 Uiso 1 1 calc R . .
C16 C 0.66595(13) 0.00683(17) 0.78574(18) 0.0425(4) Uani 1 1 d . . .
H16 H 0.7253 -0.0155 0.8338 0.051 Uiso 1 1 calc R . .
C20 C 0.56654(13) 0.26831(17) 0.50505(18) 0.0442(5) Uani 1 1 d . . .
H20 H 0.5402 0.325 0.44 0.053 Uiso 1 1 calc R . .
C21 C 0.50902(12) 0.18463(16) 0.55096(17) 0.0398(4) Uani 1 1 d . . .
H21 H 0.4433 0.1826 0.5195 0.048 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.372(2) . ?
N1 C14 1.373(2) . ?
N1 C1 1.448(2) . ?
N2 C15 1.376(2) . ?
N2 C22 1.376(2) . ?
N2 C6 1.451(2) . ?
C11 C10 1.378(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.95 . ?
C10 C9 1.406(3) . ?
C10 H10 0.95 . ?
C9 C14 1.397(2) . ?
C9 C8 1.433(2) . ?
C14 C13 1.398(2) . ?
C1 C2 1.474(2) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C3 1.194(2) . ?
C3 C4 1.382(2) . ?
C4 C5 1.194(2) . ?
C5 C6 1.473(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C22 C21 1.402(2) . ?
C22 C17 1.405(2) . ?
C17 C18 1.400(2) . ?
C17 C16 1.426(2) . ?
C18 C19 1.367(3) . ?
C18 H18 0.95 . ?
C19 C20 1.401(3) . ?
C19 H19 0.95 . ?
C8 C7 1.349(3) . ?
C8 H8 0.95 . ?
C7 H7 0.95 . ?
C13 C12 1.362(3) . ?
C13 H13 0.95 . ?
C12 H12 0.95 . ?
C15 C16 1.356(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C20 C21 1.371(2) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?

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 C14 107.98(14) . . ?
C7 N1 C1 126.36(15) . . ?
C14 N1 C1 125.58(14) . . ?
C15 N2 C22 108.05(14) . . ?
C15 N2 C6 125.63(15) . . ?
C22 N2 C6 126.07(15) . . ?
C10 C11 C12 121.98(18) . . ?
C10 C11 H11 119 . . ?
C12 C11 H11 119 . . ?
C11 C10 C9 118.40(18) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C14 C9 C10 118.31(16) . . ?
C14 C9 C8 106.21(15) . . ?
C10 C9 C8 135.47(17) . . ?
N1 C14 C9 108.44(14) . . ?
N1 C14 C13 129.01(15) . . ?
C9 C14 C13 122.53(15) . . ?
N1 C1 C2 112.59(14) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 178.24(18) . . ?
C2 C3 C4 177.30(18) . . ?
C5 C4 C3 177.12(18) . . ?
C4 C5 C6 177.60(18) . . ?
N2 C6 C5 112.82(14) . . ?
N2 C6 H6A 109 . . ?
C5 C6 H6A 109 . . ?
N2 C6 H6B 109 . . ?
C5 C6 H6B 109 . . ?
H6A C6 H6B 107.8 . . ?
N2 C22 C21 129.86(16) . . ?
N2 C22 C17 108.08(15) . . ?
C21 C22 C17 122.05(15) . . ?
C18 C17 C22 118.86(16) . . ?
C18 C17 C16 134.55(16) . . ?
C22 C17 C16 106.59(15) . . ?
C19 C18 C17 119.10(17) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.31(17) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C7 C8 C9 107.13(15) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
C8 C7 N1 110.24(16) . . ?
C8 C7 H7 124.9 . . ?
N1 C7 H7 124.9 . . ?
C12 C13 C14 117.53(17) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C13 C12 C11 121.23(18) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C16 C15 N2 110.11(16) . . ?
C16 C15 H15 124.9 . . ?
N2 C15 H15 124.9 . . ?
C15 C16 C17 107.16(16) . . ?
C15 C16 H16 126.4 . . ?
C17 C16 H16 126.4 . . ?
C21 C20 C19 121.37(17) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 117.28(16) . . ?
C20 C21 H21 121.4 . . ?
C22 C21 H21 121.4 . . ?

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 C11 C10 C9 1.1(3) . . . . ?
C11 C10 C9 C14 -0.5(2) . . . . ?
C11 C10 C9 C8 177.58(18) . . . . ?
C7 N1 C14 C9 -0.26(17) . . . . ?
C1 N1 C14 C9 -177.26(14) . . . . ?
C7 N1 C14 C13 178.45(16) . . . . ?
C1 N1 C14 C13 1.4(3) . . . . ?
C10 C9 C14 N1 178.49(14) . . . . ?
C8 C9 C14 N1 -0.14(17) . . . . ?
C10 C9 C14 C13 -0.3(2) . . . . ?
C8 C9 C14 C13 -178.95(15) . . . . ?
C7 N1 C1 C2 118.26(18) . . . . ?
C14 N1 C1 C2 -65.3(2) . . . . ?
N1 C1 C2 C3 19(6) . . . . ?
C1 C2 C3 C4 -70(8) . . . . ?
C2 C3 C4 C5 11(7) . . . . ?
C3 C4 C5 C6 -32(8) . . . . ?
C15 N2 C6 C5 94.6(2) . . . . ?
C22 N2 C6 C5 -79.0(2) . . . . ?
C4 C5 C6 N2 -142(5) . . . . ?
C15 N2 C22 C21 179.22(17) . . . . ?
C6 N2 C22 C21 -6.3(3) . . . . ?
C15 N2 C22 C17 0.25(18) . . . . ?
C6 N2 C22 C17 174.78(15) . . . . ?
N2 C22 C17 C18 -179.58(14) . . . . ?
C21 C22 C17 C18 1.4(2) . . . . ?
N2 C22 C17 C16 0.02(18) . . . . ?
C21 C22 C17 C16 -179.05(15) . . . . ?
C22 C17 C18 C19 -1.0(2) . . . . ?
C16 C17 C18 C19 179.56(18) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C14 C9 C8 C7 0.49(19) . . . . ?
C10 C9 C8 C7 -177.78(18) . . . . ?
C9 C8 C7 N1 -0.67(19) . . . . ?
C14 N1 C7 C8 0.59(19) . . . . ?
C1 N1 C7 C8 177.56(15) . . . . ?
N1 C14 C13 C12 -177.87(16) . . . . ?
C9 C14 C13 C12 0.7(2) . . . . ?
C14 C13 C12 C11 -0.1(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C22 N2 C15 C16 -0.4(2) . . . . ?
C6 N2 C15 C16 -174.99(16) . . . . ?
N2 C15 C16 C17 0.4(2) . . . . ?
C18 C17 C16 C15 179.22(19) . . . . ?
C22 C17 C16 C15 -0.28(19) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
N2 C22 C21 C20 -179.47(16) . . . . ?
C17 C22 C21 C20 -0.6(2) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/CH2Cl2'
_database_code_depnum_ccdc_archive 'CCDC 1027013'
