# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_boxd
_database_code_depnum_ccdc_archive 'CCDC 1018246'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H34 N4 O4'
_chemical_formula_weight         490.59

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'
O O 0.0106 0.0060 '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                   8.134(6)
_cell_length_b                   8.142(7)
_cell_length_c                   10.657(12)
_cell_angle_alpha                110.13(4)
_cell_angle_beta                 93.00(4)
_cell_angle_gamma                98.55(3)
_cell_volume                     651.2(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6429
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      24.78

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             262
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9494
_exptl_absorpt_correction_T_max  0.9908
_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  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6429
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2936
_reflns_number_gt                1784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0794P)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         2936
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.002
_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
C1 C 1.42557(18) 0.4385(2) 0.49978(16) 0.0372(4) Uani 1 1 d . . .
C2 C 1.17214(19) 0.3120(2) 0.44887(16) 0.0367(4) Uani 1 1 d . . .
C3 C 1.00221(19) 0.2756(2) 0.38536(16) 0.0361(4) Uani 1 1 d . . .
C4 C 0.8793(2) 0.1504(2) 0.40545(18) 0.0430(4) Uani 1 1 d . . .
H4 H 0.9064 0.0888 0.4604 0.052 Uiso 1 1 calc R . .
C5 C 0.7189(2) 0.1178(2) 0.34458(18) 0.0456(4) Uani 1 1 d . . .
H5 H 0.6381 0.0337 0.3580 0.055 Uiso 1 1 calc R . .
C6 C 0.67684(19) 0.2099(2) 0.26299(18) 0.0424(4) Uani 1 1 d . . .
C7 C 0.7966(2) 0.3354(2) 0.24346(18) 0.0451(4) Uani 1 1 d . . .
H7 H 0.7689 0.3980 0.1894 0.054 Uiso 1 1 calc R . .
C8 C 0.95798(19) 0.3672(2) 0.30472(17) 0.0408(4) Uani 1 1 d . . .
H8 H 1.0384 0.4518 0.2915 0.049 Uiso 1 1 calc R . .
C9 C 0.4690(2) 0.2562(3) 0.11646(19) 0.0522(5) Uani 1 1 d . . .
H9A H 0.5400 0.2363 0.0442 0.063 Uiso 1 1 calc R . .
H9B H 0.4818 0.3832 0.1647 0.063 Uiso 1 1 calc R . .
C10 C 0.2893(2) 0.1796(3) 0.06050(19) 0.0504(5) Uani 1 1 d . . .
H10A H 0.2211 0.1951 0.1343 0.060 Uiso 1 1 calc R . .
H10B H 0.2793 0.0530 0.0117 0.060 Uiso 1 1 calc R . .
C11 C 0.2233(2) 0.2656(2) -0.03275(19) 0.0512(5) Uani 1 1 d . . .
H11A H 0.2356 0.3926 0.0154 0.061 Uiso 1 1 calc R . .
H11B H 0.2897 0.2476 -0.1078 0.061 Uiso 1 1 calc R . .
C12 C 0.0417(2) 0.1910(2) -0.08603(18) 0.0447(4) Uani 1 1 d . . .
H12A H 0.0304 0.0643 -0.1349 0.054 Uiso 1 1 calc R . .
H12B H -0.0236 0.2067 -0.0105 0.054 Uiso 1 1 calc R . .
C13 C -0.0302(2) 0.2747(3) -0.1772(2) 0.0532(5) Uani 1 1 d . . .
H13A H 0.0328 0.2556 -0.2543 0.064 Uiso 1 1 calc R . .
H13B H -0.0157 0.4020 -0.1293 0.064 Uiso 1 1 calc R . .
C14 C -0.2136(2) 0.2039(3) -0.2270(2) 0.0694(6) Uani 1 1 d . . .
H14A H -0.2287 0.0792 -0.2789 0.104 Uiso 1 1 calc R . .
H14B H -0.2512 0.2657 -0.2821 0.104 Uiso 1 1 calc R . .
H14C H -0.2773 0.2220 -0.1515 0.104 Uiso 1 1 calc R . .
N1 N 1.40635(17) 0.32697(19) 0.56023(16) 0.0462(4) Uani 1 1 d . . .
N2 N 1.23859(16) 0.24227(19) 0.52613(15) 0.0462(4) Uani 1 1 d . . .
O1 O 1.28471(12) 0.43888(14) 0.42632(11) 0.0381(3) Uani 1 1 d . . .
O2 O 0.51523(14) 0.16827(17) 0.20649(13) 0.0536(4) Uani 1 1 d . . .


_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
C1 N1 1.279(2) . ?
C1 O1 1.354(2) . ?
C1 C1 1.451(3) 2_866 ?
C2 N2 1.288(2) . ?
C2 O1 1.370(2) . ?
C2 C3 1.449(2) . ?
C3 C8 1.383(2) . ?
C3 C4 1.398(2) . ?
C4 C5 1.372(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 O2 1.360(2) . ?
C6 C7 1.381(3) . ?
C7 C8 1.381(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 O2 1.446(2) . ?
C9 C10 1.504(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.511(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.513(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 N2 1.402(2) . ?

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
N1 C1 O1 113.69(14) . . ?
N1 C1 C1 129.11(18) . 2_866 ?
O1 C1 C1 117.20(19) . 2_866 ?
N2 C2 O1 112.24(14) . . ?
N2 C2 C3 129.97(15) . . ?
O1 C2 C3 117.80(15) . . ?
C8 C3 C4 118.61(15) . . ?
C8 C3 C2 120.16(14) . . ?
C4 C3 C2 121.23(16) . . ?
C5 C4 C3 120.42(17) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.25(15) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
O2 C6 C7 123.97(17) . . ?
O2 C6 C5 116.12(15) . . ?
C7 C6 C5 119.92(16) . . ?
C6 C7 C8 119.53(17) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C3 121.26(15) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
O2 C9 C10 107.42(15) . . ?
O2 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O2 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 C11 112.69(16) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 112.41(15) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 114.29(15) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 114.23(16) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 N2 105.78(13) . . ?
C2 N2 N1 106.45(14) . . ?
C1 O1 C2 101.84(13) . . ?
C6 O2 C9 117.52(13) . . ?

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
N2 C2 C3 C8 -179.68(17) . . . . ?
O1 C2 C3 C8 0.2(2) . . . . ?
N2 C2 C3 C4 1.3(3) . . . . ?
O1 C2 C3 C4 -178.81(14) . . . . ?
C8 C3 C4 C5 0.9(2) . . . . ?
C2 C3 C4 C5 179.92(15) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 O2 179.72(14) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
O2 C6 C7 C8 -179.54(15) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
C4 C3 C8 C7 -0.7(3) . . . . ?
C2 C3 C8 C7 -179.76(15) . . . . ?
O2 C9 C10 C11 178.12(15) . . . . ?
C9 C10 C11 C12 -178.67(16) . . . . ?
C10 C11 C12 C13 178.99(16) . . . . ?
C11 C12 C13 C14 -178.15(17) . . . . ?
O1 C1 N1 N2 0.10(19) . . . . ?
C1 C1 N1 N2 179.9(2) 2_866 . . . ?
O1 C2 N2 N1 0.65(18) . . . . ?
C3 C2 N2 N1 -179.49(16) . . . . ?
C1 N1 N2 C2 -0.45(19) . . . . ?
N1 C1 O1 C2 0.27(18) . . . . ?
C1 C1 O1 C2 -179.53(18) 2_866 . . . ?
N2 C2 O1 C1 -0.57(17) . . . . ?
C3 C2 O1 C1 179.55(14) . . . . ?
C7 C6 O2 C9 2.6(3) . . . . ?
C5 C6 O2 C9 -177.44(16) . . . . ?
C10 C9 O2 C6 176.24(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_boxd-6
_database_code_depnum_ccdc_archive 'CCDC 1018247'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_audit_creation_date             2014-07-02
_chemical_formula_sum            'C28 H34 N4 O4'
_chemical_formula_weight         490.590
_refine_ls_R_factor_all          0.152
_symmetry_cell_setting           triclinic
_cell_length_a                   8.166(6)
_cell_length_b                   13.066(9)
_cell_length_c                   14.357(14)
_cell_angle_alpha                65.13(3)
_cell_angle_beta                 73.59(3)
_cell_angle_gamma                86.14(3)
_cell_volume                     1330.8(19)
_cell_formula_units_Z            2
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P_1
_cell_measurement_reflns_used    12872
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      25
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.621
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.079
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_measured_fraction_theta_full 0.985
_cell_measurement_temperature    293

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
C ? 1.200
H ? 1.200
N ? 1.200
O ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
C1 C -0.0130(4) 0.4471(3) 0.9979(3) 1.000 2 i ? d Uani 0.0597(9)
C2 C 0.0464(4) 0.3127(3) 0.9499(3) 1.000 2 i ? d Uani 0.0589(9)
C3 C 0.1421(2) 0.2490(2) 0.8945(2) 1.000 2 i ? d Uani 0.0580(9)
C4 C 0.0570(2) 0.1565(2) 0.9010(2) 1.000 2 i ? d Uani 0.0659(10)
H4 H -0.0571 0.1380 0.9406 1.000 2 i ? calc Uiso 0.07900
C5 C 0.1425(2) 0.0917(2) 0.8486(2) 1.000 2 i ? d Uani 0.0677(10)
H5 H 0.0856 0.0298 0.8530 1.000 2 i ? calc Uiso 0.08100
C6 C 0.3131(2) 0.1193(2) 0.7895(2) 1.000 2 i ? d Uani 0.0617(9)
C7 C 0.3981(2) 0.2118(2) 0.7829(2) 1.000 2 i ? d Uani 0.070(1)
H7 H 0.5123 0.2304 0.7434 1.000 2 i ? calc Uiso 0.08400
C8 C 0.3127(2) 0.2767(2) 0.8354(2) 1.000 2 i ? d Uani 0.0676(10)
H8 H 0.3696 0.3385 0.8310 1.000 2 i ? calc Uiso 0.08100
C9 C 0.3218(5) -0.0342(3) 0.7398(3) 1.000 2 i ? d Uani 0.0739(10)
H9A H 0.2199 -0.0111 0.7159 1.000 2 i ? calc Uiso 0.08900
H9B H 0.2875 -0.0918 0.8126 1.000 2 i ? calc Uiso 0.08900
C10 C 0.4414(5) -0.0808(3) 0.6690(3) 1.000 2 i ? d Uani 0.0753(11)
H10A H 0.5416 -0.1059 0.6944 1.000 2 i ? calc Uiso 0.09000
H10B H 0.4788 -0.0221 0.5968 1.000 2 i ? calc Uiso 0.09000
C11 C 0.3545(5) -0.1790(3) 0.6684(3) 1.000 2 i ? d Uani 0.0824(12)
H11A H 0.3092 -0.2337 0.7418 1.000 2 i ? calc Uiso 0.09900
H11B H 0.2581 -0.1514 0.6395 1.000 2 i ? calc Uiso 0.09900
C12 C 0.4622(6) -0.2381(3) 0.6070(4) 1.000 2 i ? d Uani 0.0971(14)
H12A H 0.5632 -0.2615 0.6317 1.000 2 i ? calc Uiso 0.11700
H12B H 0.4995 -0.1859 0.5320 1.000 2 i ? calc Uiso 0.11700
C13 C 0.3664(7) -0.3439(4) 0.6182(5) 1.000 2 i ? d Uani 0.147(2)
H13A H 0.3264 -0.3945 0.6935 1.000 2 i ? calc Uiso 0.17700
H13B H 0.2666 -0.3196 0.5922 1.000 2 i ? calc Uiso 0.17700
C14 C 0.4656(9) -0.4045(5) 0.5628(7) 1.000 2 i ? d Uani 0.199(3)
H14A H 0.5121 -0.3541 0.4889 1.000 2 i ? calc Uiso 0.29800
H14B H 0.3949 -0.4637 0.5683 1.000 2 i ? calc Uiso 0.29800
H14C H 0.5572 -0.4367 0.5937 1.000 2 i ? calc Uiso 0.29800
C15 C 0.4346(4) 0.0191(3) 0.0338(3) 1.000 2 i ? d Uani 0.0580(9)
C16 C 0.3224(4) 0.1271(3) 0.1070(3) 1.000 2 i ? d Uani 0.0594(9)
C17 C 0.3079(2) 0.2237(2) 0.1324(2) 1.000 2 i ? d Uani 0.0568(9)
C18 C 0.4477(2) 0.2990(2) 0.0971(2) 1.000 2 i ? d Uani 0.0642(10)
H18 H 0.5515 0.2883 0.0554 1.000 2 i ? calc Uiso 0.07700
C19 C 0.4322(2) 0.3902(2) 0.1243(2) 1.000 2 i ? d Uani 0.0701(10)
H19 H 0.5257 0.4405 0.1008 1.000 2 i ? calc Uiso 0.08400
C20 C 0.2771(3) 0.4061(2) 0.1868(2) 1.000 2 i ? d Uani 0.0642(10)
C21 C 0.1373(2) 0.3308(2) 0.2220(2) 1.000 2 i ? d Uani 0.0707(10)
H21 H 0.0335 0.3415 0.2638 1.000 2 i ? calc Uiso 0.08500
C22 C 0.1527(2) 0.2396(2) 0.1948(2) 1.000 2 i ? d Uani 0.0688(10)
H22 H 0.0592 0.1892 0.2184 1.000 2 i ? calc Uiso 0.08300
C23 C 0.1266(5) 0.5187(3) 0.2750(3) 1.000 2 i ? d Uani 0.0753(11)
H23A H 0.0907 0.4535 0.3433 1.000 2 i ? calc Uiso 0.09000
H23B H 0.0348 0.5339 0.2412 1.000 2 i ? calc Uiso 0.09000
C24 C 0.1677(5) 0.6196(3) 0.2909(3) 1.000 2 i ? d Uani 0.0811(11)
H24A H 0.2063 0.6830 0.2216 1.000 2 i ? calc Uiso 0.09700
H24B H 0.2611 0.6030 0.3235 1.000 2 i ? calc Uiso 0.09700
C25 C 0.0189(5) 0.6534(3) 0.3598(3) 1.000 2 i ? d Uani 0.0821(12)
H25A H -0.0232 0.5895 0.4284 1.000 2 i ? calc Uiso 0.09800
H25B H -0.0729 0.6741 0.3259 1.000 2 i ? calc Uiso 0.09800
C26 C 0.0701(6) 0.7529(3) 0.3775(4) 1.000 2 i ? d Uani 0.0961(13)
H26A H 0.1617 0.7312 0.4116 1.000 2 i ? calc Uiso 0.11500
H26B H 0.1146 0.8157 0.3084 1.000 2 i ? calc Uiso 0.11500
C27 C -0.0678(7) 0.7907(3) 0.4421(4) 1.000 2 i ? d Uani 0.1165(17)
H27A H -0.1120 0.7283 0.5115 1.000 2 i ? calc Uiso 0.14000
H27B H -0.1596 0.8124 0.4082 1.000 2 i ? calc Uiso 0.14000
C28 C -0.0136(8) 0.8915(4) 0.4586(5) 1.000 2 i ? d Uani 0.150(2)
H28A H 0.0728 0.8695 0.4958 1.000 2 i ? calc Uiso 0.22500
H28B H -0.1110 0.9141 0.4999 1.000 2 i ? calc Uiso 0.22500
H28C H 0.0313 0.9536 0.3903 1.000 2 i ? calc Uiso 0.22500
N1 N -0.1073(4) 0.2906(2) 1.0135(3) 1.000 2 i ? d Uani 0.0751(9)
N2 N -0.1453(3) 0.3798(2) 1.0445(2) 1.000 2 i ? d Uani 0.0742(9)
N3 N 0.2860(4) -0.0256(2) 0.0892(3) 1.000 2 i ? d Uani 0.0730(9)
N4 N 0.2087(3) 0.0460(2) 0.1383(3) 1.000 2 i ? d Uani 0.0757(9)
O1 O 0.1152(3) 0.4133(2) 0.9355(2) 1.000 2 i ? d Uani 0.0618(6)
O2 O 0.4059(3) 0.0614(2) 0.7361(2) 1.000 2 i ? d Uani 0.0766(8)
O3 O 0.4699(3) 0.1158(2) 0.0399(2) 1.000 2 i ? d Uani 0.0614(6)
O4 O 0.2772(3) 0.4974(2) 0.2089(2) 1.000 2 i ? d Uani 0.0860(8)



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . . 1.269(4) no
C1 O1 . . 1.354(4) no
C1 C1 . 2_567 1.441(6) no
C2 N1 . . 1.292(4) no
C2 O1 . . 1.375(3) no
C2 C3 . . 1.435(4) no
C3 C4 . . 1.3900 no
C3 C8 . . 1.3900 no
C4 C5 . . 1.3900 no
C4 H4 . . 0.9300 no
C5 C6 . . 1.3900 no
C5 H5 . . 0.9300 no
C6 O2 . . 1.349(3) no
C6 C7 . . 1.3900 no
C7 C8 . . 1.3900 no
C7 H7 . . 0.9300 no
C8 H8 . . 0.9300 no
C9 O2 . . 1.440(4) no
C9 C10 . . 1.496(5) no
C9 H9A . . 0.9700 no
C9 H9B . . 0.9700 no
C10 C11 . . 1.512(5) no
C10 H10A . . 0.9700 no
C10 H10B . . 0.9700 no
C11 C12 . . 1.480(5) no
C11 H11A . . 0.9700 no
C11 H11B . . 0.9700 no
C12 C13 . . 1.560(5) no
C12 H12A . . 0.9700 no
C12 H12B . . 0.9700 no
C13 C14 . . 1.412(7) no
C13 H13A . . 0.9700 no
C13 H13B . . 0.9700 no
C14 H14A . . 0.9600 no
C14 H14B . . 0.9600 no
C14 H14C . . 0.9600 no
C15 N3 . . 1.267(4) no
C15 O3 . . 1.358(4) no
C15 C15 . 2_655 1.443(6) no
C16 N4 . . 1.297(4) no
C16 O3 . . 1.357(4) no
C16 C17 . . 1.442(4) no
C17 C18 . . 1.3900 no
C17 C22 . . 1.3900 no
C18 C19 . . 1.3900 no
C18 H18 . . 0.9300 no
C19 C20 . . 1.3900 no
C19 H19 . . 0.9300 no
C20 O4 . . 1.358(3) no
C20 C21 . . 1.3900 no
C21 C22 . . 1.3900 no
C21 H21 . . 0.9300 no
C22 H22 . . 0.9300 no
C23 O4 . . 1.417(4) no
C23 C24 . . 1.504(4) no
C23 H23A . . 0.9700 no
C23 H23B . . 0.9700 no
C24 C25 . . 1.505(5) no
C24 H24A . . 0.9700 no
C24 H24B . . 0.9700 no
C25 C26 . . 1.530(5) no
C25 H25A . . 0.9700 no
C25 H25B . . 0.9700 no
C26 C27 . . 1.447(5) no
C26 H26A . . 0.9700 no
C26 H26B . . 0.9700 no
C27 C28 . . 1.545(6) no
C27 H27A . . 0.9700 no
C27 H27B . . 0.9700 no
C28 H28A . . 0.9600 no
C28 H28B . . 0.9600 no
C28 H28C . . 0.9600 no
N1 N2 . . 1.402(4) no
N3 N4 . . 1.412(4) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 O1 . . . 113.8(3) no
N2 C1 C1 . . 2_567 128.1(4) no
O1 C1 C1 . . 2_567 118.0(3) no
N1 C2 O1 . . . 111.4(3) no
N1 C2 C3 . . . 128.3(3) no
O1 C2 C3 . . . 120.2(2) no
C4 C3 C8 . . . 120.00 no
C4 C3 C2 . . . 117.25(18) no
C8 C3 C2 . . . 122.75(18) no
C5 C4 C3 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C4 C5 C6 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
O2 C6 C7 . . . 115.94(17) no
O2 C6 C5 . . . 124.06(17) no
C7 C6 C5 . . . 120.00 no
C6 C7 C8 . . . 120.00 no
C6 C7 H7 . . . 120.00 no
C8 C7 H7 . . . 120.00 no
C7 C8 C3 . . . 120.00 no
C7 C8 H8 . . . 120.00 no
C3 C8 H8 . . . 120.00 no
O2 C9 C10 . . . 109.4(3) no
O2 C9 H9A . . . 109.80 no
C10 C9 H9A . . . 109.80 no
O2 C9 H9B . . . 109.80 no
C10 C9 H9B . . . 109.80 no
H9A C9 H9B . . . 108.30 no
C9 C10 C11 . . . 110.5(3) no
C9 C10 H10A . . . 109.50 no
C11 C10 H10A . . . 109.50 no
C9 C10 H10B . . . 109.50 no
C11 C10 H10B . . . 109.50 no
H10A C10 H10B . . . 108.10 no
C12 C11 C10 . . . 116.2(3) no
C12 C11 H11A . . . 108.20 no
C10 C11 H11A . . . 108.20 no
C12 C11 H11B . . . 108.20 no
C10 C11 H11B . . . 108.20 no
H11A C11 H11B . . . 107.40 no
C11 C12 C13 . . . 112.7(4) no
C11 C12 H12A . . . 109.00 no
C13 C12 H12A . . . 109.00 no
C11 C12 H12B . . . 109.00 no
C13 C12 H12B . . . 109.00 no
H12A C12 H12B . . . 107.80 no
C14 C13 C12 . . . 114.7(5) no
C14 C13 H13A . . . 108.60 no
C12 C13 H13A . . . 108.60 no
C14 C13 H13B . . . 108.60 no
C12 C13 H13B . . . 108.60 no
H13A C13 H13B . . . 107.60 no
C13 C14 H14A . . . 109.50 no
C13 C14 H14B . . . 109.50 no
H14A C14 H14B . . . 109.50 no
C13 C14 H14C . . . 109.50 no
H14A C14 H14C . . . 109.50 no
H14B C14 H14C . . . 109.50 no
N3 C15 O3 . . . 113.9(3) no
N3 C15 C15 . . 2_655 128.3(4) no
O3 C15 C15 . . 2_655 117.8(3) no
N4 C16 O3 . . . 112.1(3) no
N4 C16 C17 . . . 128.7(3) no
O3 C16 C17 . . . 119.2(2) no
C18 C17 C22 . . . 120.00 no
C18 C17 C16 . . . 120.85(19) no
C22 C17 C16 . . . 119.14(19) no
C19 C18 C17 . . . 120.00 no
C19 C18 H18 . . . 120.00 no
C17 C18 H18 . . . 120.00 no
C20 C19 C18 . . . 120.00 no
C20 C19 H19 . . . 120.00 no
C18 C19 H19 . . . 120.00 no
O4 C20 C19 . . . 114.85(18) no
O4 C20 C21 . . . 125.15(18) no
C19 C20 C21 . . . 120.00 no
C22 C21 C20 . . . 120.00 no
C22 C21 H21 . . . 120.00 no
C20 C21 H21 . . . 120.00 no
C21 C22 C17 . . . 120.00 no
C21 C22 H22 . . . 120.00 no
C17 C22 H22 . . . 120.00 no
O4 C23 C24 . . . 107.2(3) no
O4 C23 H23A . . . 110.30 no
C24 C23 H23A . . . 110.30 no
O4 C23 H23B . . . 110.30 no
C24 C23 H23B . . . 110.30 no
H23A C23 H23B . . . 108.50 no
C23 C24 C25 . . . 113.7(3) no
C23 C24 H24A . . . 108.80 no
C25 C24 H24A . . . 108.80 no
C23 C24 H24B . . . 108.80 no
C25 C24 H24B . . . 108.80 no
H24A C24 H24B . . . 107.70 no
C24 C25 C26 . . . 111.4(3) no
C24 C25 H25A . . . 109.30 no
C26 C25 H25A . . . 109.30 no
C24 C25 H25B . . . 109.30 no
C26 C25 H25B . . . 109.30 no
H25A C25 H25B . . . 108.00 no
C27 C26 C25 . . . 114.3(4) no
C27 C26 H26A . . . 108.70 no
C25 C26 H26A . . . 108.70 no
C27 C26 H26B . . . 108.70 no
C25 C26 H26B . . . 108.70 no
H26A C26 H26B . . . 107.60 no
C26 C27 C28 . . . 113.5(4) no
C26 C27 H27A . . . 108.90 no
C28 C27 H27A . . . 108.90 no
C26 C27 H27B . . . 108.90 no
C28 C27 H27B . . . 108.90 no
H27A C27 H27B . . . 107.70 no
C27 C28 H28A . . . 109.50 no
C27 C28 H28B . . . 109.50 no
H28A C28 H28B . . . 109.50 no
C27 C28 H28C . . . 109.50 no
H28A C28 H28C . . . 109.50 no
H28B C28 H28C . . . 109.50 no
C2 N1 N2 . . . 106.7(3) no
C1 N2 N1 . . . 106.0(3) no
C15 N3 N4 . . . 105.7(3) no
C16 N4 N3 . . . 106.0(3) no
C1 O1 C2 . . . 102.1(2) no
C6 O2 C9 . . . 117.7(2) no
C16 O3 C15 . . . 102.2(2) no
C20 O4 C23 . . . 119.1(2) no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C2 C3 C4 . . . . 6.2(4) no
O1 C2 C3 C4 . . . . -171.5(2) no
N1 C2 C3 C8 . . . . -174.2(3) no
O1 C2 C3 C8 . . . . 8.2(4) no
C8 C3 C4 C5 . . . . 0.00 no
C2 C3 C4 C5 . . . . 179.6(2) no
C3 C4 C5 C6 . . . . 0.00 no
C4 C5 C6 O2 . . . . -180.0(2) no
C4 C5 C6 C7 . . . . 0.00 no
O2 C6 C7 C8 . . . . 180.0(2) no
C5 C6 C7 C8 . . . . 0.00 no
C6 C7 C8 C3 . . . . 0.00 no
C4 C3 C8 C7 . . . . 0.00 no
C2 C3 C8 C7 . . . . -179.6(2) no
O2 C9 C10 C11 . . . . -178.1(3) no
C9 C10 C11 C12 . . . . -176.1(3) no
C10 C11 C12 C13 . . . . 175.4(4) no
C11 C12 C13 C14 . . . . -178.7(5) no
N4 C16 C17 C18 . . . . 175.7(3) no
O3 C16 C17 C18 . . . . -6.0(4) no
N4 C16 C17 C22 . . . . -2.9(5) no
O3 C16 C17 C22 . . . . 175.4(2) no
C22 C17 C18 C19 . . . . 0.00 no
C16 C17 C18 C19 . . . . -178.6(2) no
C17 C18 C19 C20 . . . . 0.00 no
C18 C19 C20 O4 . . . . 179.6(2) no
C18 C19 C20 C21 . . . . 0.00 no
O4 C20 C21 C22 . . . . -179.6(2) no
C19 C20 C21 C22 . . . . 0.00 no
C20 C21 C22 C17 . . . . 0.00 no
C18 C17 C22 C21 . . . . 0.00 no
C16 C17 C22 C21 . . . . 178.6(2) no
O4 C23 C24 C25 . . . . 179.8(3) no
C23 C24 C25 C26 . . . . 177.4(3) no
C24 C25 C26 C27 . . . . 179.3(4) no
C25 C26 C27 C28 . . . . -179.8(4) no
O1 C2 N1 N2 . . . . -0.3(4) no
C3 C2 N1 N2 . . . . -178.1(3) no
O1 C1 N2 N1 . . . . 0.6(4) no
C1 C1 N2 N1 2_567 . . . 179.0(4) no
C2 N1 N2 C1 . . . . -0.2(4) no
O3 C15 N3 N4 . . . . 0.4(4) no
C15 C15 N3 N4 2_655 . . . -178.7(4) no
O3 C16 N4 N3 . . . . 0.4(4) no
C17 C16 N4 N3 . . . . 178.8(3) no
C15 N3 N4 C16 . . . . -0.5(4) no
N2 C1 O1 C2 . . . . -0.7(4) no
C1 C1 O1 C2 2_567 . . . -179.3(4) no
N1 C2 O1 C1 . . . . 0.6(4) no
C3 C2 O1 C1 . . . . 178.6(3) no
C7 C6 O2 C9 . . . . -179.2(2) no
C5 C6 O2 C9 . . . . 0.8(3) no
C10 C9 O2 C6 . . . . 175.5(3) no
N4 C16 O3 C15 . . . . -0.2(4) no
C17 C16 O3 C15 . . . . -178.8(3) no
N3 C15 O3 C16 . . . . -0.2(4) no
C15 C15 O3 C16 2_655 . . . 179.1(4) no
C19 C20 O4 C23 . . . . -177.9(3) no
C21 C20 O4 C23 . . . . 1.7(4) no
C24 C23 O4 C20 . . . . 176.5(3) no
_chemical_name_systematic        
2,2-Bis-(4-hexyloxyphenyl)-bi-1,3,4-oxadiazole
_chemical_formula_moiety         C28H34N4O4
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_preparation       Luminescent
