# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1499076'
_audit_update_record             
;
2016-08-14 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1,4-bis(3-(4-butylphenyl)quinoxalin-2-yl)benzene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H38 N4'
_chemical_formula_weight         598.76

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   'P2(1)/n  '

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

_cell_length_a                   5.981(4)
_cell_length_b                   14.384(4)
_cell_length_c                   19.951(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.31(3)
_cell_angle_gamma                90.00
_cell_volume                     1714.9(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1320
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      22.32

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_process_details   SADABS

_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            8379
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3006
_reflns_number_gt                1646
_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)+(0.0500P)²+0.4700P] 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     SHELXL
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3006
_refine_ls_number_parameters     209
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1596
_refine_ls_wR_factor_gt          0.1459
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.224
_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 0.3778(4) 0.92892(18) 0.16690(12) 0.0598(7) Uani 1 1 d . . .
N2 N 0.6224(4) 1.08684(17) 0.12617(12) 0.0563(7) Uani 1 1 d . . .
C1 C 0.3257(5) 1.0169(2) 0.18876(14) 0.0570(8) Uani 1 1 d . . .
C2 C 0.1424(6) 1.0299(3) 0.23103(16) 0.0732(10) Uani 1 1 d . . .
H2A H 0.0549 0.9795 0.2428 0.088 Uiso 1 1 calc R . .
C3 C 0.0951(6) 1.1173(3) 0.25442(17) 0.0813(12) Uani 1 1 d . . .
H3A H -0.0270 1.1257 0.2812 0.098 Uiso 1 1 calc R . .
C4 C 0.2278(7) 1.1942(3) 0.23856(18) 0.0818(11) Uani 1 1 d . . .
H4A H 0.1954 1.2525 0.2558 0.098 Uiso 1 1 calc R . .
C5 C 0.4046(6) 1.1835(2) 0.19785(16) 0.0722(10) Uani 1 1 d . . .
H5A H 0.4923 1.2345 0.1877 0.087 Uiso 1 1 calc R . .
C6 C 0.4549(5) 1.0949(2) 0.17111(15) 0.0568(8) Uani 1 1 d . . .
C7 C 0.6653(5) 1.0023(2) 0.10256(14) 0.0497(8) Uani 1 1 d . . .
C8 C 0.5476(5) 0.9210(2) 0.12574(14) 0.0523(8) Uani 1 1 d . . .
C9 C 0.8374(5) 0.9985(2) 0.05009(14) 0.0484(8) Uani 1 1 d . . .
C10 C 0.8290(5) 0.9345(2) -0.00330(14) 0.0524(8) Uani 1 1 d . . .
H10A H 0.7144 0.8907 -0.0063 0.063 Uiso 1 1 calc R . .
C11 C 0.9898(5) 0.9359(2) -0.05143(15) 0.0524(8) Uani 1 1 d . . .
H11A H 0.9826 0.8920 -0.0856 0.063 Uiso 1 1 calc R . .
C12 C 0.6102(5) 0.8232(2) 0.10939(14) 0.0514(8) Uani 1 1 d . . .
C13 C 0.4539(5) 0.7624(2) 0.07908(17) 0.0657(9) Uani 1 1 d . . .
H13A H 0.3114 0.7838 0.0667 0.079 Uiso 1 1 calc R . .
C14 C 0.5101(6) 0.6702(2) 0.06728(17) 0.0720(10) Uani 1 1 d . . .
H14A H 0.4044 0.6313 0.0465 0.086 Uiso 1 1 calc R . .
C15 C 0.7195(6) 0.6348(2) 0.08568(16) 0.0645(9) Uani 1 1 d . . .
C16 C 0.8744(6) 0.6957(2) 0.11547(17) 0.0692(10) Uani 1 1 d . . .
H16A H 1.0162 0.6738 0.1281 0.083 Uiso 1 1 calc R . .
C17 C 0.8232(5) 0.7885(2) 0.12688(16) 0.0624(9) Uani 1 1 d . . .
H17A H 0.9312 0.8277 0.1463 0.075 Uiso 1 1 calc R . .
C18 C 0.7804(8) 0.5330(3) 0.0749(2) 0.0968(13) Uani 1 1 d . . .
H18A H 0.6581 0.5038 0.0494 0.116 Uiso 1 1 calc R . .
H18B H 0.9107 0.5310 0.0475 0.116 Uiso 1 1 calc R . .
C19 C 0.8282(11) 0.4769(4) 0.1350(3) 0.158(2) Uani 1 1 d U . .
H19A H 0.7022 0.4839 0.1637 0.190 Uiso 1 1 calc R . .
H19B H 0.9566 0.5046 0.1586 0.190 Uiso 1 1 calc R . .
C20 C 0.8764(13) 0.3696(5) 0.1292(4) 0.194(3) Uani 1 1 d DU . .
H20A H 0.9001 0.3433 0.1737 0.233 Uiso 1 1 calc R . .
H20B H 0.7482 0.3389 0.1076 0.233 Uiso 1 1 calc R . .
C21 C 1.0567(16) 0.3552(6) 0.0936(4) 0.254(4) Uani 1 1 d DU . .
H21A H 1.0800 0.2895 0.0886 0.381 Uiso 1 1 calc R . .
H21B H 1.1851 0.3824 0.1164 0.381 Uiso 1 1 calc R . .
H21C H 1.0350 0.3832 0.0501 0.381 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 C8 1.336(3) . ?
N1 C1 1.378(4) . ?
N2 C7 1.333(3) . ?
N2 C6 1.376(4) . ?
C1 C6 1.415(4) . ?
C1 C2 1.422(4) . ?
C2 C3 1.373(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.405(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.418(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.450(4) . ?
C7 C9 1.498(4) . ?
C8 C12 1.495(4) . ?
C9 C11 1.399(4) 3_775 ?
C9 C10 1.408(4) . ?
C10 C11 1.387(4) . ?
C10 H10A 0.9300 . ?
C11 C9 1.399(4) 3_775 ?
C11 H11A 0.9300 . ?
C12 C17 1.399(4) . ?
C12 C13 1.400(4) . ?
C13 C14 1.389(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.388(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.392(4) . ?
C15 C18 1.526(5) . ?
C16 C17 1.389(4) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.464(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.575(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.331(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C8 N1 C1 117.4(3) . . ?
C7 N2 C6 117.6(3) . . ?
N1 C1 C6 121.1(3) . . ?
N1 C1 C2 119.9(3) . . ?
C6 C1 C2 119.0(3) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
N2 C6 C1 121.0(3) . . ?
N2 C6 C5 119.5(3) . . ?
C1 C6 C5 119.5(3) . . ?
N2 C7 C8 121.3(3) . . ?
N2 C7 C9 115.3(3) . . ?
C8 C7 C9 123.3(3) . . ?
N1 C8 C7 121.2(3) . . ?
N1 C8 C12 114.7(3) . . ?
C7 C8 C12 124.0(2) . . ?
C11 C9 C10 117.3(3) 3_775 . ?
C11 C9 C7 119.3(3) 3_775 . ?
C10 C9 C7 123.2(3) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C9 122.0(3) . 3_775 ?
C10 C11 H11A 119.0 . . ?
C9 C11 H11A 119.0 3_775 . ?
C17 C12 C13 118.0(3) . . ?
C17 C12 C8 121.0(3) . . ?
C13 C12 C8 120.9(3) . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C15 C14 C13 121.8(3) . . ?
C15 C14 H14A 119.1 . . ?
C13 C14 H14A 119.1 . . ?
C14 C15 C16 117.4(3) . . ?
C14 C15 C18 122.2(3) . . ?
C16 C15 C18 120.4(3) . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 H16A 119.1 . . ?
C15 C16 H16A 119.1 . . ?
C16 C17 C12 120.4(3) . . ?
C16 C17 H17A 119.8 . . ?
C12 C17 H17A 119.8 . . ?
C19 C18 C15 117.0(4) . . ?
C19 C18 H18A 108.1 . . ?
C15 C18 H18A 108.1 . . ?
C19 C18 H18B 108.1 . . ?
C15 C18 H18B 108.1 . . ?
H18A C18 H18B 107.3 . . ?
C18 C19 C20 120.7(5) . . ?
C18 C19 H19A 107.2 . . ?
C20 C19 H19A 107.2 . . ?
C18 C19 H19B 107.2 . . ?
C20 C19 H19B 107.2 . . ?
H19A C19 H19B 106.8 . . ?
C21 C20 C19 110.3(7) . . ?
C21 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C8 N1 C1 C6 -3.3(4) . . . . ?
C8 N1 C1 C2 178.1(3) . . . . ?
N1 C1 C2 C3 178.0(3) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C7 N2 C6 C1 -3.2(4) . . . . ?
C7 N2 C6 C5 179.6(3) . . . . ?
N1 C1 C6 N2 6.6(5) . . . . ?
C2 C1 C6 N2 -174.8(3) . . . . ?
N1 C1 C6 C5 -176.2(3) . . . . ?
C2 C1 C6 C5 2.4(5) . . . . ?
C4 C5 C6 N2 175.0(3) . . . . ?
C4 C5 C6 C1 -2.2(5) . . . . ?
C6 N2 C7 C8 -2.9(4) . . . . ?
C6 N2 C7 C9 175.7(3) . . . . ?
C1 N1 C8 C7 -2.8(4) . . . . ?
C1 N1 C8 C12 174.2(3) . . . . ?
N2 C7 C8 N1 6.2(4) . . . . ?
C9 C7 C8 N1 -172.3(3) . . . . ?
N2 C7 C8 C12 -170.5(3) . . . . ?
C9 C7 C8 C12 11.0(4) . . . . ?
N2 C7 C9 C11 30.5(4) . . . 3_775 ?
C8 C7 C9 C11 -150.9(3) . . . 3_775 ?
N2 C7 C9 C10 -146.2(3) . . . . ?
C8 C7 C9 C10 32.3(4) . . . . ?
C11 C9 C10 C11 1.4(5) 3_775 . . . ?
C7 C9 C10 C11 178.2(3) . . . . ?
C9 C10 C11 C9 -1.5(5) . . . 3_775 ?
N1 C8 C12 C17 -118.3(3) . . . . ?
C7 C8 C12 C17 58.6(4) . . . . ?
N1 C8 C12 C13 58.6(4) . . . . ?
C7 C8 C12 C13 -124.5(3) . . . . ?
C17 C12 C13 C14 0.3(4) . . . . ?
C8 C12 C13 C14 -176.6(3) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C13 C14 C15 C18 178.1(3) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C18 C15 C16 C17 -179.0(3) . . . . ?
C15 C16 C17 C12 1.0(5) . . . . ?
C13 C12 C17 C16 -1.3(4) . . . . ?
C8 C12 C17 C16 175.7(3) . . . . ?
C14 C15 C18 C19 -115.2(5) . . . . ?
C16 C15 C18 C19 64.0(6) . . . . ?
C15 C18 C19 C20 175.8(5) . . . . ?
C18 C19 C20 C21 60.9(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetic acid'
