# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_H-2C6
_database_code_depnum_ccdc_archive 'CCDC 1507713'
_audit_update_record             
;
2016-10-01 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
1,3-bis[5-(4-(hexyloxy)phenyl)-1,3,4-oxadiazol-2-yl]benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H37 N5 O6'
_chemical_formula_sum            'C34 H37 N5 O6'
_chemical_formula_weight         611.68

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.583(2)
_cell_length_b                   10.9650(10)
_cell_length_c                   14.503(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.007(9)
_cell_angle_gamma                90
_cell_volume                     3189.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      5.50
_cell_measurement_theta_max      15.16

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CAD-4 Enraf-Nonius Diffractometer'
_diffrn_measurement_method       ω--2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3258
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         2.031
_diffrn_reflns_theta_max         25.969
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3125
_reflns_number_gt                2109
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       
;
SET4 in CAD-4 Software  (Enraf-Nonius, 1989)   
;
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2012 (Sheldrick, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1136P)²+4.2817P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3125
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.2269
_refine_ls_wR_factor_gt          0.1984
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5000 0.6934(3) 0.2500 0.0523(9) Uani 1 2 d S T P . .
O1 O 0.54255(14) 0.7452(2) 0.21813(18) 0.0700(7) Uani 1 1 d . . . . .
C1 C 0.5000 0.5589(4) 0.2500 0.0438(9) Uani 1 2 d S T P . .
C2 C 0.51978(15) 0.4983(3) 0.17709(19) 0.0457(7) Uani 1 1 d . . . . .
H2 H 0.5332 0.5413 0.1293 0.055 Uiso 1 1 calc R U . . .
C3 C 0.51911(14) 0.3718(3) 0.17722(19) 0.0436(7) Uani 1 1 d . . . . .
C4 C 0.5000 0.3080(4) 0.2500 0.0448(9) Uani 1 2 d S T P . .
H4 H 0.5000 0.2232 0.2500 0.054 Uiso 1 2 calc R U P . .
C5 C 0.53887(15) 0.3080(3) 0.09892(19) 0.0445(7) Uani 1 1 d . . . . .
N6 N 0.54809(15) 0.3555(2) 0.02234(18) 0.0587(7) Uani 1 1 d . . . . .
N7 N 0.56722(16) 0.2595(2) -0.03053(19) 0.0589(8) Uani 1 1 d . . . . .
C8 C 0.56775(15) 0.1620(3) 0.0195(2) 0.0463(7) Uani 1 1 d . . . . .
O9 O 0.55015(10) 0.18553(17) 0.10370(13) 0.0462(5) Uani 1 1 d . . . . .
C10 C 0.58615(15) 0.0398(3) -0.0025(2) 0.0459(7) Uani 1 1 d . . . . .
C11 C 0.60099(17) 0.0185(3) -0.0908(2) 0.0547(8) Uani 1 1 d . . . . .
H11 H 0.5964 0.0812 -0.1350 0.066 Uiso 1 1 calc R U . . .
C12 C 0.62236(18) -0.0946(3) -0.1125(2) 0.0577(8) Uani 1 1 d . . . . .
H12 H 0.6321 -0.1079 -0.1713 0.069 Uiso 1 1 calc R U . . .
C13 C 0.62955(16) -0.1891(3) -0.0472(2) 0.0520(8) Uani 1 1 d . . . . .
C14 C 0.61210(17) -0.1705(3) 0.0393(2) 0.0536(8) Uani 1 1 d . . . . .
H14 H 0.6148 -0.2342 0.0823 0.064 Uiso 1 1 calc R U . . .
C15 C 0.59079(16) -0.0564(3) 0.0605(2) 0.0516(8) Uani 1 1 d . . . . .
H15 H 0.5793 -0.0440 0.1182 0.062 Uiso 1 1 calc R U . . .
O16 O 0.65381(14) -0.2947(2) -0.07433(18) 0.0698(7) Uani 1 1 d . . . . .
C17 C 0.6696(2) -0.3933(3) -0.0066(3) 0.0809(12) Uani 1 1 d . . . . .
H17A H 0.6290 -0.4308 0.0034 0.097 Uiso 1 1 calc R U . . .
H17B H 0.6950 -0.3630 0.0536 0.097 Uiso 1 1 calc R U . . .
C18 C 0.7112(3) -0.4869(4) -0.0488(4) 0.0974(15) Uani 1 1 d . . . . .
H18A H 0.7500 -0.4466 -0.0619 0.117 Uiso 1 1 calc R U . . .
H18B H 0.7266 -0.5507 -0.0027 0.117 Uiso 1 1 calc R U . . .
C19 C 0.6727(3) -0.5414(4) -0.1355(4) 0.0969(14) Uani 1 1 d . . . . .
H19A H 0.6520 -0.4771 -0.1780 0.116 Uiso 1 1 calc R U . . .
H19B H 0.6375 -0.5913 -0.1206 0.116 Uiso 1 1 calc R U . . .
C20 C 0.7184(4) -0.6246(6) -0.1881(5) 0.145(3) Uani 1 1 d . . . . .
H20A H 0.6926 -0.6452 -0.2507 0.173 Uiso 1 1 calc R U . . .
H20B H 0.7565 -0.5769 -0.1958 0.173 Uiso 1 1 calc R U . . .
C21 C 0.7407(4) -0.7293(6) -0.1414(5) 0.138(2) Uani 1 1 d . . . . .
H21A H 0.7036 -0.7715 -0.1243 0.165 Uiso 1 1 calc R U . . .
H21B H 0.7730 -0.7098 -0.0836 0.165 Uiso 1 1 calc R U . . .
C22 C 0.7733(4) -0.8136(6) -0.2036(5) 0.149(3) Uani 1 1 d . . . . .
H22A H 0.7868 -0.8884 -0.1704 0.224 Uiso 1 1 calc R U . . .
H22B H 0.8116 -0.7738 -0.2172 0.224 Uiso 1 1 calc R U . . .
H22C H 0.7418 -0.8309 -0.2617 0.224 Uiso 1 1 calc R U . . .


_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 O1 1.219(3) 2_655 ?
N1 O1 1.219(3) . ?
N1 C1 1.474(5) . ?
C1 C2 1.386(3) . ?
C1 C2 1.386(3) 2_655 ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(3) . ?
C3 C5 1.467(4) . ?
C4 C3 1.394(3) 2_655 ?
C4 H4 0.9300 . ?
C5 N6 1.279(4) . ?
C5 O9 1.362(3) . ?
N6 N7 1.409(3) . ?
N7 C8 1.292(4) . ?
C8 O9 1.374(3) . ?
C8 C10 1.447(4) . ?
C10 C15 1.384(4) . ?
C10 C11 1.402(4) . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9300 . ?
C13 O16 1.354(4) . ?
C13 C14 1.396(4) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
O16 C17 1.448(4) . ?
C17 C18 1.548(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.454(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.618(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.359(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.546(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O1 N1 O1 124.5(4) 2_655 . ?
O1 N1 C1 117.77(19) 2_655 . ?
O1 N1 C1 117.76(19) . . ?
C2 C1 C2 122.6(4) . 2_655 ?
C2 C1 N1 118.68(19) . . ?
C2 C1 N1 118.68(19) 2_655 . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 C5 118.1(3) . . ?
C4 C3 C5 121.4(3) . . ?
C3 C4 C3 119.8(4) 2_655 . ?
C3 C4 H4 120.1 2_655 . ?
C3 C4 H4 120.1 . . ?
N6 C5 O9 112.9(2) . . ?
N6 C5 C3 126.9(3) . . ?
O9 C5 C3 120.3(2) . . ?
C5 N6 N7 106.5(2) . . ?
C8 N7 N6 106.3(2) . . ?
N7 C8 O9 111.9(3) . . ?
N7 C8 C10 127.8(3) . . ?
O9 C8 C10 120.3(2) . . ?
C5 O9 C8 102.5(2) . . ?
C15 C10 C11 118.6(3) . . ?
C15 C10 C8 122.9(3) . . ?
C11 C10 C8 118.5(3) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
O16 C13 C12 115.5(3) . . ?
O16 C13 C14 124.9(3) . . ?
C12 C13 C14 119.6(3) . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C13 O16 C17 118.9(3) . . ?
O16 C17 C18 106.6(3) . . ?
O16 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O16 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C19 C18 C17 111.9(4) . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 112.2(5) . . ?
C18 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 114.1(6) . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C19 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 C22 110.9(6) . . ?
C20 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O1 N1 C1 C2 146.75(19) 2_655 . . . ?
O1 N1 C1 C2 -33.26(19) . . . . ?
O1 N1 C1 C2 -33.25(19) 2_655 . . 2_655 ?
O1 N1 C1 C2 146.74(19) . . . 2_655 ?
C2 C1 C2 C3 0.5(2) 2_655 . . . ?
N1 C1 C2 C3 -179.5(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C2 C3 C5 178.8(2) . . . . ?
C2 C3 C4 C3 0.5(2) . . . 2_655 ?
C5 C3 C4 C3 -179.4(3) . . . 2_655 ?
C2 C3 C5 N6 -10.6(5) . . . . ?
C4 C3 C5 N6 169.3(3) . . . . ?
C2 C3 C5 O9 168.7(3) . . . . ?
C4 C3 C5 O9 -11.4(4) . . . . ?
O9 C5 N6 N7 0.0(4) . . . . ?
C3 C5 N6 N7 179.3(3) . . . . ?
C5 N6 N7 C8 0.1(4) . . . . ?
N6 N7 C8 O9 -0.1(4) . . . . ?
N6 N7 C8 C10 -177.9(3) . . . . ?
N6 C5 O9 C8 0.0(3) . . . . ?
C3 C5 O9 C8 -179.4(3) . . . . ?
N7 C8 O9 C5 0.1(3) . . . . ?
C10 C8 O9 C5 178.1(3) . . . . ?
N7 C8 C10 C15 173.8(3) . . . . ?
O9 C8 C10 C15 -3.8(5) . . . . ?
N7 C8 C10 C11 -5.1(5) . . . . ?
O9 C8 C10 C11 177.3(3) . . . . ?
C15 C10 C11 C12 -2.7(5) . . . . ?
C8 C10 C11 C12 176.3(3) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C11 C12 C13 O16 -177.1(3) . . . . ?
C11 C12 C13 C14 2.9(5) . . . . ?
O16 C13 C14 C15 177.0(3) . . . . ?
C12 C13 C14 C15 -3.0(5) . . . . ?
C13 C14 C15 C10 0.3(5) . . . . ?
C11 C10 C15 C14 2.5(5) . . . . ?
C8 C10 C15 C14 -176.4(3) . . . . ?
C12 C13 O16 C17 173.4(3) . . . . ?
C14 C13 O16 C17 -6.5(5) . . . . ?
C13 O16 C17 C18 -166.7(3) . . . . ?
O16 C17 C18 C19 -64.5(5) . . . . ?
C17 C18 C19 C20 171.9(4) . . . . ?
C18 C19 C20 C21 69.6(8) . . . . ?
C19 C20 C21 C22 170.3(6) . . . . ?

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.053

_shelxl_version_number           2012-9


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
