# 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 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_I
_database_code_depnum_ccdc_archive 'CCDC 968416'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            phthalonitrile
_chemical_formula_moiety         'C20 H28 N2 O S2'
_chemical_formula_sum            'C20 H28 N2 O S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         376.56

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9476(8)
_cell_length_b                   10.2758(9)
_cell_length_c                   12.1482(11)
_cell_angle_alpha                98.043(4)
_cell_angle_beta                 95.114(4)
_cell_angle_gamma                110.648(4)
_cell_volume                     1023.30(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    82
_cell_measurement_theta_min      3.8785
_cell_measurement_theta_max      21.4373
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404

_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16083
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_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.
;

_reflns_number_total             3573
_reflns_number_gt                3242
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1467
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         3573
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0697P)²+1.0481P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.379
_refine_diff_density_min         -0.421
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL V6.14 (Bruker, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3564(3) 0.5037(3) -0.1264(2) 0.0334(6) Uani d . 1 . .
C C2 0.1318(3) 0.5317(3) -0.2947(2) 0.0329(6) Uani d . 1 . .
C C3 0.2468(3) 0.5716(3) -0.0952(2) 0.0285(5) Uani d . 1 . .
C C4 0.1389(3) 0.5877(3) -0.1784(2) 0.0282(5) Uani d . 1 . .
C C5 0.0364(3) 0.6575(3) -0.1488(2) 0.0284(5) Uani d . 1 . .
H H5 -0.0354 0.6691 -0.2057 0.034 Uiso calc R 1 . .
C C6 0.0380(3) 0.7105(2) -0.0368(2) 0.0269(5) Uani d . 1 . .
C C7 0.1473(3) 0.6945(2) 0.0478(2) 0.0269(5) Uani d . 1 . .
C C8 0.2504(3) 0.6254(3) 0.0171(2) 0.0288(5) Uani d . 1 . .
H H8 0.3238 0.6149 0.0734 0.035 Uiso calc R 1 . .
C C9 0.2849(3) 0.7115(3) 0.2677(2) 0.0327(6) Uani d . 1 . .
H H9A 0.2512 0.6073 0.2514 0.039 Uiso calc R 1 . .
H H9B 0.3939 0.7536 0.2468 0.039 Uiso calc R 1 . .
C C10 0.2891(3) 0.7616(3) 0.3919(2) 0.0369(6) Uani d . 1 . .
H H10A 0.1778 0.7288 0.4103 0.044 Uiso calc R 1 . .
H H10B 0.3339 0.8663 0.4091 0.044 Uiso calc R 1 . .
C C11 0.3926(4) 0.7050(3) 0.4643(2) 0.0397(6) Uani d . 1 . .
H H11A 0.369 0.7169 0.5423 0.048 Uiso calc R 1 . .
H H11B 0.3606 0.6024 0.436 0.048 Uiso calc R 1 . .
C C12 0.5731(3) 0.7763(3) 0.4660(2) 0.0403(7) Uani d . 1 . .
H H12A 0.6085 0.8766 0.5033 0.048 Uiso calc R 1 . .
H H12B 0.5963 0.7744 0.3878 0.048 Uiso calc R 1 . .
C C13 0.6685(4) 0.7047(3) 0.5274(2) 0.0435(7) Uani d . 1 . .
H H13A 0.6305 0.6915 0.6007 0.052 Uiso calc R 1 . .
H H13B 0.6463 0.6098 0.4829 0.052 Uiso calc R 1 . .
C C14 0.8463(4) 0.7859(4) 0.5475(3) 0.0553(9) Uani d . 1 . .
H H14A 0.8853 0.8002 0.4748 0.066 Uiso calc R 1 . .
H H14B 0.87 0.88 0.5939 0.066 Uiso calc R 1 . .
C C15 -0.2107(3) 0.7923(3) -0.1216(2) 0.0315(6) Uani d . 1 . .
H H15A -0.141 0.8442 -0.1724 0.038 Uiso calc R 1 . .
H H15B -0.2694 0.6933 -0.1607 0.038 Uiso calc R 1 . .
C C16 -0.3298(3) 0.8615(3) -0.0909(2) 0.0320(6) Uani d . 1 . .
H H16A -0.2694 0.9602 -0.0518 0.038 Uiso calc R 1 . .
H H16B -0.3963 0.8102 -0.0383 0.038 Uiso calc R 1 . .
C C17 -0.4404(3) 0.8613(3) -0.1941(2) 0.0307(6) Uani d . 1 . .
H H17A -0.3735 0.9071 -0.2487 0.037 Uiso calc R 1 . .
H H17B -0.5057 0.7623 -0.2304 0.037 Uiso calc R 1 . .
C C18 -0.5527(3) 0.9383(3) -0.1650(2) 0.0306(6) Uani d . 1 . .
H H18A -0.487 1.0368 -0.1277 0.037 Uiso calc R 1 . .
H H18B -0.62 0.8918 -0.1108 0.037 Uiso calc R 1 . .
C C19 -0.6632(3) 0.9409(3) -0.2671(2) 0.0337(6) Uani d . 1 . .
H H19A -0.733 0.8426 -0.3024 0.04 Uiso calc R 1 . .
H H19B -0.5964 0.9836 -0.3229 0.04 Uiso calc R 1 . .
C C20 -0.7696(3) 1.0246(3) -0.2367(3) 0.0402(6) Uani d . 1 . .
H H20A -0.8375 0.9818 -0.1825 0.06 Uiso calc R 1 . .
H H20B -0.8384 1.0231 -0.3047 0.06 Uiso calc R 1 . .
H H20C -0.7012 1.1227 -0.2034 0.06 Uiso calc R 1 . .
N N1 0.4466(3) 0.4527(3) -0.1525(2) 0.0450(6) Uani d . 1 . .
N N2 0.1229(3) 0.4867(3) -0.3877(2) 0.0431(6) Uani d . 1 . .
O O1 0.9292(3) 0.7113(3) 0.6040(2) 0.0687(7) Uani d . 1 . .
H H1 0.9306 0.6426 0.5583 0.103 Uiso calc R 1 . .
S S1 0.14319(7) 0.76480(7) 0.18707(5) 0.0311(2) Uani d . 1 . .
S S2 -0.08891(7) 0.79684(7) 0.00744(5) 0.0323(2) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.151(4) ?
C1 C3 . 1.437(4) ?
C2 N2 . 1.143(3) ?
C2 C4 . 1.436(4) ?
C3 C8 . 1.392(4) ?
C3 C4 . 1.403(3) ?
C4 C5 . 1.392(3) ?
C5 C6 . 1.390(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.422(3) ?
C6 S2 . 1.747(2) ?
C7 C8 . 1.393(3) ?
C7 S1 . 1.753(2) ?
C8 H8 . 0.95 ?
C9 C10 . 1.517(4) ?
C9 S1 . 1.812(3) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C11 . 1.531(4) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.517(4) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.520(4) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.492(5) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 O1 . 1.437(4) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.520(3) ?
C15 S2 . 1.813(3) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C17 . 1.526(4) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C18 . 1.519(3) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 C19 . 1.525(3) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 C20 . 1.528(4) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
O1 H1 . 0.84 ?

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_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C3 . . 178.1(3) ?
N2 C2 C4 . . 178.6(3) ?
C8 C3 C4 . . 119.6(2) ?
C8 C3 C1 . . 120.4(2) ?
C4 C3 C1 . . 120.0(2) ?
C5 C4 C3 . . 120.1(2) ?
C5 C4 C2 . . 119.2(2) ?
C3 C4 C2 . . 120.6(2) ?
C6 C5 C4 . . 120.7(2) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C7 . . 119.4(2) ?
C5 C6 S2 . . 123.45(19) ?
C7 C6 S2 . . 117.17(18) ?
C8 C7 C6 . . 119.5(2) ?
C8 C7 S1 . . 123.75(19) ?
C6 C7 S1 . . 116.78(18) ?
C3 C8 C7 . . 120.7(2) ?
C3 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C10 C9 S1 . . 108.96(18) ?
C10 C9 H9A . . 109.9 ?
S1 C9 H9A . . 109.9 ?
C10 C9 H9B . . 109.9 ?
S1 C9 H9B . . 109.9 ?
H9A C9 H9B . . 108.3 ?
C9 C10 C11 . . 111.0(2) ?
C9 C10 H10A . . 109.4 ?
C11 C10 H10A . . 109.4 ?
C9 C10 H10B . . 109.4 ?
C11 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
C12 C11 C10 . . 114.5(2) ?
C12 C11 H11A . . 108.6 ?
C10 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C10 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
C11 C12 C13 . . 112.2(2) ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12B . . 109.2 ?
C13 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C14 C13 C12 . . 113.4(3) ?
C14 C13 H13A . . 108.9 ?
C12 C13 H13A . . 108.9 ?
C14 C13 H13B . . 108.9 ?
C12 C13 H13B . . 108.9 ?
H13A C13 H13B . . 107.7 ?
O1 C14 C13 . . 110.6(3) ?
O1 C14 H14A . . 109.5 ?
C13 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
C16 C15 S2 . . 107.81(17) ?
C16 C15 H15A . . 110.1 ?
S2 C15 H15A . . 110.1 ?
C16 C15 H15B . . 110.1 ?
S2 C15 H15B . . 110.1 ?
H15A C15 H15B . . 108.5 ?
C15 C16 C17 . . 112.0(2) ?
C15 C16 H16A . . 109.2 ?
C17 C16 H16A . . 109.2 ?
C15 C16 H16B . . 109.2 ?
C17 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C18 C17 C16 . . 112.4(2) ?
C18 C17 H17A . . 109.1 ?
C16 C17 H17A . . 109.1 ?
C18 C17 H17B . . 109.1 ?
C16 C17 H17B . . 109.1 ?
H17A C17 H17B . . 107.9 ?
C17 C18 C19 . . 113.4(2) ?
C17 C18 H18A . . 108.9 ?
C19 C18 H18A . . 108.9 ?
C17 C18 H18B . . 108.9 ?
C19 C18 H18B . . 108.9 ?
H18A C18 H18B . . 107.7 ?
C18 C19 C20 . . 112.5(2) ?
C18 C19 H19A . . 109.1 ?
C20 C19 H19A . . 109.1 ?
C18 C19 H19B . . 109.1 ?
C20 C19 H19B . . 109.1 ?
H19A C19 H19B . . 107.8 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C14 O1 H1 . . 109.5 ?
C7 S1 C9 . . 103.23(12) ?
C6 S2 C15 . . 104.03(12) ?

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 C1 C3 C8 . . . . -104.(9) ?
N1 C1 C3 C4 . . . . 74.(9) ?
C8 C3 C4 C5 . . . . 0.2(4) ?
C1 C3 C4 C5 . . . . -177.9(2) ?
C8 C3 C4 C2 . . . . -179.3(2) ?
C1 C3 C4 C2 . . . . 2.6(4) ?
N2 C2 C4 C5 . . . . -28.(12) ?
N2 C2 C4 C3 . . . . 151.(12) ?
C3 C4 C5 C6 . . . . -0.8(4) ?
C2 C4 C5 C6 . . . . 178.7(2) ?
C4 C5 C6 C7 . . . . 0.9(4) ?
C4 C5 C6 S2 . . . . -178.97(18) ?
C5 C6 C7 C8 . . . . -0.3(3) ?
S2 C6 C7 C8 . . . . 179.51(18) ?
C5 C6 C7 S1 . . . . 179.65(18) ?
S2 C6 C7 S1 . . . . -0.5(3) ?
C4 C3 C8 C7 . . . . 0.3(4) ?
C1 C3 C8 C7 . . . . 178.4(2) ?
C6 C7 C8 C3 . . . . -0.3(4) ?
S1 C7 C8 C3 . . . . 179.77(18) ?
S1 C9 C10 C11 . . . . 173.61(19) ?
C9 C10 C11 C12 . . . . 73.7(3) ?
C10 C11 C12 C13 . . . . -173.2(2) ?
C11 C12 C13 C14 . . . . -170.3(3) ?
C12 C13 C14 O1 . . . . -179.0(3) ?
S2 C15 C16 C17 . . . . -179.21(18) ?
C15 C16 C17 C18 . . . . -176.4(2) ?
C16 C17 C18 C19 . . . . 179.4(2) ?
C17 C18 C19 C20 . . . . -177.4(2) ?
C8 C7 S1 C9 . . . . -4.3(2) ?
C6 C7 S1 C9 . . . . 175.74(18) ?
C10 C9 S1 C7 . . . . -178.01(18) ?
C5 C6 S2 C15 . . . . 1.2(2) ?
C7 C6 S2 C15 . . . . -178.64(18) ?
C16 C15 S2 C6 . . . . 178.15(17) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N2 2_665 0.84 2.21 2.980(4) 152.0 ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
