# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 968399'
_audit_update_record             
;
2015-05-03 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            phthalonitrile
_chemical_formula_moiety         'C30 H12 N6 O3 '
_chemical_formula_sum            'C30 H12 N6 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         504.46

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   14.4563(14)
_cell_length_b                   24.746(2)
_cell_length_c                   14.626(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.294(6)
_cell_angle_gamma                90
_cell_volume                     4841.1(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    43
_cell_measurement_theta_min      3.4425
_cell_measurement_theta_max      18.4957
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       'small block'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2064

_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  1.00

_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 ?

_diffrn_reflns_number            32709
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_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             4263
_reflns_number_gt                2394
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1294
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_number_reflns         4263
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0362P)²+5.2568P] 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         0.199
_refine_diff_density_min         -0.204
_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'

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS, 2009)'
_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  
'PLATON V1.16 (Spek, 2009), 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 0.5827(2) 0.53248(14) 0.1246(2) 0.0373(8) Uani d . 1 . .
C C2 0.3861(3) 0.52405(14) 0.1233(2) 0.0421(8) Uani d . 1 . .
C C3 0.4419(2) 0.47628(11) 0.1236(2) 0.0330(7) Uani d . 1 . .
C C4 0.3984(2) 0.42615(12) 0.1230(2) 0.0347(7) Uani d . 1 . .
H H4 0.3327 0.4235 0.1227 0.042 Uiso calc R 1 . .
C C5 0.4527(2) 0.38016(12) 0.1227(2) 0.0346(7) Uani d . 1 . .
C C6 0.5495(2) 0.38391(13) 0.1260(2) 0.0390(8) Uani d . 1 . .
H H6 0.5865 0.352 0.1276 0.047 Uiso calc R 1 . .
C C7 0.5922(2) 0.43334(13) 0.1270(2) 0.0399(8) Uani d . 1 . .
H H7 0.6585 0.4355 0.1288 0.048 Uiso calc R 1 . .
C C8 0.5394(2) 0.48033(12) 0.1253(2) 0.0348(8) Uani d . 1 . .
C C9 0.1483(2) 0.53599(15) -0.3313(3) 0.0492(9) Uani d . 1 . .
C C10 0.1032(3) 0.43876(15) -0.4403(3) 0.0507(9) Uani d . 1 . .
C C11 0.1189(2) 0.43821(13) -0.3368(2) 0.0386(8) Uani d . 1 . .
C C12 0.1130(2) 0.39025(13) -0.2914(2) 0.0367(8) Uani d . 1 . .
H H12 0.1037 0.3571 -0.3265 0.044 Uiso calc R 1 . .
C C13 0.1207(2) 0.39096(12) -0.1941(2) 0.0308(7) Uani d . 1 . .
C C14 0.1350(2) 0.43900(12) -0.1418(2) 0.0351(7) Uani d . 1 . .
H H14 0.1386 0.4391 -0.0756 0.042 Uiso calc R 1 . .
C C15 0.1440(2) 0.48655(12) -0.1864(2) 0.0364(8) Uani d . 1 . .
H H15 0.1557 0.5194 -0.1501 0.044 Uiso calc R 1 . .
C C16 0.1363(2) 0.48710(13) -0.2843(2) 0.0384(8) Uani d . 1 . .
C C17 -0.1646(3) 0.33873(15) 0.1281(3) 0.0494(9) Uani d . 1 . .
C C18 -0.2596(3) 0.23916(12) 0.1228(2) 0.0397(8) Uani d . 1 . .
C C19 -0.1598(2) 0.24079(12) 0.1212(2) 0.0368(8) Uani d . 1 . .
C C20 -0.1104(3) 0.19357(13) 0.1187(2) 0.0471(9) Uani d . 1 . .
H H20 -0.1418 0.1597 0.1172 0.057 Uiso calc R 1 . .
C C21 -0.0154(3) 0.19552(13) 0.1184(2) 0.0470(9) Uani d . 1 . .
H H21 0.0188 0.1629 0.1169 0.056 Uiso calc R 1 . .
C C22 0.0305(2) 0.24465(12) 0.1201(2) 0.0370(8) Uani d . 1 . .
C C23 -0.0174(2) 0.29265(12) 0.1217(2) 0.0359(8) Uani d . 1 . .
H H23 0.0143 0.3263 0.1222 0.043 Uiso calc R 1 . .
C C24 -0.1134(2) 0.29057(12) 0.1226(2) 0.0355(8) Uani d . 1 . .
C C25 0.2597(2) 0.34127(11) -0.0150(2) 0.0318(7) Uani d . 1 . .
H H25 0.292 0.3623 -0.0485 0.038 Uiso calc R 1 . .
C C26 0.1597(2) 0.32911(11) -0.0590(2) 0.0319(7) Uani d . 1 . .
C C27 0.1111(2) 0.29763(11) -0.0130(2) 0.0349(8) Uani d . 1 . .
H H27 0.0421 0.2892 -0.0444 0.042 Uiso calc R 1 . .
C C28 0.1675(2) 0.27895(11) 0.0810(2) 0.0361(8) Uani d . 1 . .
C C29 0.2676(2) 0.29080(11) 0.1286(2) 0.0360(8) Uani d . 1 . .
H H29 0.3047 0.2779 0.1934 0.043 Uiso calc R 1 . .
C C30 0.3117(2) 0.32210(11) 0.0787(2) 0.0343(7) Uani d . 1 . .
N N1 0.6160(2) 0.57435(12) 0.1232(2) 0.0475(7) Uani d . 1 . .
N N2 0.3409(2) 0.56278(12) 0.1243(2) 0.0612(9) Uani d . 1 . .
N N3 0.1608(2) 0.57391(13) -0.3704(2) 0.0690(10) Uani d . 1 . .
N N4 0.0871(2) 0.44019(15) -0.5230(2) 0.0753(10) Uani d . 1 . .
N N5 -0.2078(3) 0.37686(13) 0.1342(3) 0.0779(11) Uani d . 1 . .
N N6 -0.3384(2) 0.23783(12) 0.1235(2) 0.0529(8) Uani d . 1 . .
O O1 0.41510(15) 0.32939(8) 0.12423(16) 0.0428(6) Uani d . 1 . .
O O2 0.10459(15) 0.34226(8) -0.15712(14) 0.0374(5) Uani d . 1 . .
O O3 0.12881(16) 0.24252(8) 0.13016(17) 0.0501(6) 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 . 1.146(4) ?
C1 C8 . 1.436(4) ?
C2 N2 . 1.163(4) ?
C2 C3 . 1.430(5) ?
C3 C4 . 1.389(4) ?
C3 C8 . 1.404(4) ?
C4 C5 . 1.384(4) ?
C4 H4 . 0.95 ?
C5 O1 . 1.373(3) ?
C5 C6 . 1.384(4) ?
C6 C7 . 1.367(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.386(4) ?
C7 H7 . 0.95 ?
C9 N3 . 1.148(4) ?
C9 C16 . 1.434(5) ?
C10 N4 . 1.141(4) ?
C10 C11 . 1.443(4) ?
C11 C12 . 1.378(4) ?
C11 C16 . 1.403(4) ?
C12 C13 . 1.385(4) ?
C12 H12 . 0.95 ?
C13 O2 . 1.377(3) ?
C13 C14 . 1.386(4) ?
C14 C15 . 1.376(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.394(4) ?
C15 H15 . 0.95 ?
C17 N5 . 1.154(4) ?
C17 C24 . 1.420(5) ?
C18 N6 . 1.145(4) ?
C18 C19 . 1.451(5) ?
C19 C20 . 1.378(4) ?
C19 C24 . 1.399(4) ?
C20 C21 . 1.376(4) ?
C20 H20 . 0.95 ?
C21 C22 . 1.380(4) ?
C21 H21 . 0.95 ?
C22 O3 . 1.374(3) ?
C22 C23 . 1.380(4) ?
C23 C24 . 1.394(4) ?
C23 H23 . 0.95 ?
C25 C30 . 1.373(4) ?
C25 C26 . 1.375(4) ?
C25 H25 . 0.95 ?
C26 C27 . 1.383(4) ?
C26 O2 . 1.390(3) ?
C27 C28 . 1.385(4) ?
C27 H27 . 0.95 ?
C28 C29 . 1.378(4) ?
C28 O3 . 1.395(3) ?
C29 C30 . 1.376(4) ?
C29 H29 . 0.95 ?
C30 O1 . 1.398(3) ?

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 C8 . . 179.1(4) ?
N2 C2 C3 . . 179.2(4) ?
C4 C3 C8 . . 120.9(3) ?
C4 C3 C2 . . 119.0(3) ?
C8 C3 C2 . . 120.2(3) ?
C5 C4 C3 . . 118.6(3) ?
C5 C4 H4 . . 120.7 ?
C3 C4 H4 . . 120.7 ?
O1 C5 C6 . . 117.5(3) ?
O1 C5 C4 . . 121.6(3) ?
C6 C5 C4 . . 120.8(3) ?
C7 C6 C5 . . 120.4(3) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C8 . . 120.5(3) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
C7 C8 C3 . . 118.8(3) ?
C7 C8 C1 . . 121.1(3) ?
C3 C8 C1 . . 120.1(3) ?
N3 C9 C16 . . 176.9(4) ?
N4 C10 C11 . . 177.2(4) ?
C12 C11 C16 . . 120.7(3) ?
C12 C11 C10 . . 119.9(3) ?
C16 C11 C10 . . 119.3(3) ?
C11 C12 C13 . . 119.2(3) ?
C11 C12 H12 . . 120.4 ?
C13 C12 H12 . . 120.4 ?
O2 C13 C12 . . 115.7(3) ?
O2 C13 C14 . . 123.1(3) ?
C12 C13 C14 . . 121.0(3) ?
C15 C14 C13 . . 119.5(3) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C14 C15 C16 . . 120.7(3) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C15 C16 C11 . . 118.8(3) ?
C15 C16 C9 . . 121.6(3) ?
C11 C16 C9 . . 119.6(3) ?
N5 C17 C24 . . 177.7(4) ?
N6 C18 C19 . . 179.6(4) ?
C20 C19 C24 . . 119.8(3) ?
C20 C19 C18 . . 120.4(3) ?
C24 C19 C18 . . 119.8(3) ?
C21 C20 C19 . . 119.9(3) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C20 C21 C22 . . 120.2(3) ?
C20 C21 H21 . . 119.9 ?
C22 C21 H21 . . 119.9 ?
O3 C22 C23 . . 122.5(3) ?
O3 C22 C21 . . 116.0(3) ?
C23 C22 C21 . . 121.2(3) ?
C22 C23 C24 . . 118.4(3) ?
C22 C23 H23 . . 120.8 ?
C24 C23 H23 . . 120.8 ?
C23 C24 C19 . . 120.4(3) ?
C23 C24 C17 . . 120.7(3) ?
C19 C24 C17 . . 118.9(3) ?
C30 C25 C26 . . 118.2(3) ?
C30 C25 H25 . . 120.9 ?
C26 C25 H25 . . 120.9 ?
C25 C26 C27 . . 122.2(3) ?
C25 C26 O2 . . 121.4(3) ?
C27 C26 O2 . . 115.9(3) ?
C26 C27 C28 . . 117.1(3) ?
C26 C27 H27 . . 121.5 ?
C28 C27 H27 . . 121.5 ?
C29 C28 C27 . . 122.7(3) ?
C29 C28 O3 . . 115.3(3) ?
C27 C28 O3 . . 121.8(3) ?
C30 C29 C28 . . 117.5(3) ?
C30 C29 H29 . . 121.3 ?
C28 C29 H29 . . 121.3 ?
C25 C30 C29 . . 122.4(3) ?
C25 C30 O1 . . 120.8(3) ?
C29 C30 O1 . . 116.5(3) ?
C5 O1 C30 . . 118.0(2) ?
C13 O2 C26 . . 119.6(2) ?
C22 O3 C28 . . 121.4(2) ?

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
N2 C2 C3 C4 . . . . 80.(30) ?
N2 C2 C3 C8 . . . . -100.(30) ?
C8 C3 C4 C5 . . . . -0.8(4) ?
C2 C3 C4 C5 . . . . 179.7(3) ?
C3 C4 C5 O1 . . . . 178.6(3) ?
C3 C4 C5 C6 . . . . 1.9(4) ?
O1 C5 C6 C7 . . . . -178.5(3) ?
C4 C5 C6 C7 . . . . -1.7(5) ?
C5 C6 C7 C8 . . . . 0.4(5) ?
C6 C7 C8 C3 . . . . 0.7(4) ?
C6 C7 C8 C1 . . . . -179.0(3) ?
C4 C3 C8 C7 . . . . -0.4(4) ?
C2 C3 C8 C7 . . . . 179.1(3) ?
C4 C3 C8 C1 . . . . 179.2(3) ?
C2 C3 C8 C1 . . . . -1.3(4) ?
N1 C1 C8 C7 . . . . 140.(20) ?
N1 C1 C8 C3 . . . . -40.(20) ?
N4 C10 C11 C12 . . . . 108.(9) ?
N4 C10 C11 C16 . . . . -69.(9) ?
C16 C11 C12 C13 . . . . 2.4(4) ?
C10 C11 C12 C13 . . . . -175.1(3) ?
C11 C12 C13 O2 . . . . 174.1(2) ?
C11 C12 C13 C14 . . . . -0.5(4) ?
O2 C13 C14 C15 . . . . -175.7(3) ?
C12 C13 C14 C15 . . . . -1.5(4) ?
C13 C14 C15 C16 . . . . 1.7(4) ?
C14 C15 C16 C11 . . . . 0.1(4) ?
C14 C15 C16 C9 . . . . -178.2(3) ?
C12 C11 C16 C15 . . . . -2.2(4) ?
C10 C11 C16 C15 . . . . 175.3(3) ?
C12 C11 C16 C9 . . . . 176.2(3) ?
C10 C11 C16 C9 . . . . -6.3(4) ?
N3 C9 C16 C15 . . . . 131.(7) ?
N3 C9 C16 C11 . . . . -47.(8) ?
N6 C18 C19 C20 . . . . -80.(50) ?
N6 C18 C19 C24 . . . . 100.(50) ?
C24 C19 C20 C21 . . . . 0.5(5) ?
C18 C19 C20 C21 . . . . -179.2(3) ?
C19 C20 C21 C22 . . . . -0.3(5) ?
C20 C21 C22 O3 . . . . 173.4(3) ?
C20 C21 C22 C23 . . . . -0.3(5) ?
O3 C22 C23 C24 . . . . -172.6(3) ?
C21 C22 C23 C24 . . . . 0.7(4) ?
C22 C23 C24 C19 . . . . -0.5(4) ?
C22 C23 C24 C17 . . . . 177.6(3) ?
C20 C19 C24 C23 . . . . -0.1(4) ?
C18 C19 C24 C23 . . . . 179.6(3) ?
C20 C19 C24 C17 . . . . -178.2(3) ?
C18 C19 C24 C17 . . . . 1.5(4) ?
N5 C17 C24 C23 . . . . -150.(11) ?
N5 C17 C24 C19 . . . . 28.(11) ?
C30 C25 C26 C27 . . . . -1.3(4) ?
C30 C25 C26 O2 . . . . -173.3(2) ?
C25 C26 C27 C28 . . . . 0.7(4) ?
O2 C26 C27 C28 . . . . 173.1(2) ?
C26 C27 C28 C29 . . . . 0.3(4) ?
C26 C27 C28 O3 . . . . -173.4(2) ?
C27 C28 C29 C30 . . . . -0.6(4) ?
O3 C28 C29 C30 . . . . 173.5(3) ?
C26 C25 C30 C29 . . . . 1.0(4) ?
C26 C25 C30 O1 . . . . 174.8(2) ?
C28 C29 C30 C25 . . . . 0.0(4) ?
C28 C29 C30 O1 . . . . -174.1(2) ?
C6 C5 O1 C30 . . . . -152.1(3) ?
C4 C5 O1 C30 . . . . 31.2(4) ?
C25 C30 O1 C5 . . . . 48.5(4) ?
C29 C30 O1 C5 . . . . -137.3(3) ?
C12 C13 O2 C26 . . . . 144.1(3) ?
C14 C13 O2 C26 . . . . -41.4(4) ?
C25 C26 O2 C13 . . . . -39.8(4) ?
C27 C26 O2 C13 . . . . 147.8(3) ?
C23 C22 O3 C28 . . . . -43.1(4) ?
C21 C22 O3 C28 . . . . 143.2(3) ?
C29 C28 O3 C22 . . . . 150.1(3) ?
C27 C28 O3 C22 . . . . -35.7(4) ?

####################################################################### 
# 
# 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 968400'
_audit_update_record             
;
2015-05-03 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            phthalonitrile
_chemical_formula_moiety         ' 	C22 H10 N4 O2 '
_chemical_formula_sum            'C22 H10 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         362.34

_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                   8.0768(5)
_cell_length_b                   8.5809(5)
_cell_length_c                   13.4764(8)
_cell_angle_alpha                74.672(3)
_cell_angle_beta                 88.214(3)
_cell_angle_gamma                77.262(3)
_cell_volume                     878.24(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    86
_cell_measurement_theta_min      3.2882
_cell_measurement_theta_max      30.3770
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.85
_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            56718
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_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             3074
_reflns_number_gt                2829
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0843
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_number_reflns         3074
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0283P)²+0.4010P] 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         0.181
_refine_diff_density_min         -0.170
_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'

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS, 2009)'
_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  
'PLATON V1.16 (Spek, 2009), 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 0.42003(18) 0.11077(18) -0.17086(11) 0.0295(3) Uani d . 1 . .
C C2 0.37024(18) 0.33854(17) -0.37656(11) 0.0294(3) Uani d . 1 . .
C C3 0.45035(16) 0.37469(17) -0.29421(10) 0.0256(3) Uani d . 1 . .
C C4 0.50339(17) 0.52314(17) -0.31341(11) 0.0290(3) Uani d . 1 . .
H H4 0.484 0.5989 -0.3797 0.035 Uiso calc R 1 . .
C C5 0.58397(18) 0.56174(17) -0.23703(11) 0.0300(3) Uani d . 1 . .
H H5 0.6185 0.6641 -0.2503 0.036 Uiso calc R 1 . .
C C6 0.61384(17) 0.45003(17) -0.14109(11) 0.0276(3) Uani d . 1 . .
C C7 0.56054(18) 0.30176(17) -0.11908(10) 0.0283(3) Uani d . 1 . .
H H7 0.5799 0.2273 -0.0524 0.034 Uiso calc R 1 . .
C C8 0.47876(16) 0.26355(16) -0.19542(10) 0.0253(3) Uani d . 1 . .
C C9 0.82597(17) 0.38630(16) -0.00945(10) 0.0258(3) Uani d . 1 . .
C C10 0.93807(18) 0.27027(17) -0.04727(10) 0.0287(3) Uani d . 1 . .
H H10 0.9203 0.2579 -0.1139 0.034 Uiso calc R 1 . .
C C11 1.07697(18) 0.17237(18) 0.01412(11) 0.0310(3) Uani d . 1 . .
H H11 1.1536 0.0907 -0.0104 0.037 Uiso calc R 1 . .
C C12 1.10599(18) 0.19147(17) 0.11055(11) 0.0298(3) Uani d . 1 . .
H H12 1.2016 0.1246 0.1522 0.036 Uiso calc R 1 . .
C C13 0.99197(17) 0.31035(17) 0.14429(10) 0.0253(3) Uani d . 1 . .
C C14 0.85124(17) 0.40803(16) 0.08654(10) 0.0256(3) Uani d . 1 . .
H H14 0.7736 0.4881 0.1119 0.031 Uiso calc R 1 . .
C C15 0.90324(18) 0.26352(18) 0.59759(11) 0.0301(3) Uani d . 1 . .
C C16 0.70435(17) 0.03198(17) 0.58682(11) 0.0284(3) Uani d . 1 . .
C C17 0.78266(16) 0.11266(16) 0.49618(10) 0.0248(3) Uani d . 1 . .
C C18 0.76303(17) 0.07590(16) 0.40344(10) 0.0263(3) Uani d . 1 . .
H H18 0.6957 -0.0004 0.4 0.032 Uiso calc R 1 . .
C C19 0.84046(17) 0.14920(16) 0.31635(10) 0.0256(3) Uani d . 1 . .
H H19 0.8266 0.1237 0.2531 0.031 Uiso calc R 1 . .
C C20 0.93906(16) 0.26090(16) 0.32196(10) 0.0228(3) Uani d . 1 . .
C C21 0.96034(17) 0.30041(16) 0.41365(10) 0.0245(3) Uani d . 1 . .
H H21 1.0275 0.3773 0.4164 0.029 Uiso calc R 1 . .
C C22 0.88245(16) 0.22640(16) 0.50082(10) 0.0244(3) Uani d . 1 . .
N N1 0.37336(19) -0.01057(17) -0.14682(10) 0.0420(3) Uani d . 1 . .
N N2 0.30892(18) 0.31635(16) -0.44590(10) 0.0392(3) Uani d . 1 . .
N N3 0.91796(19) 0.28974(18) 0.67525(10) 0.0448(3) Uani d . 1 . .
N N4 0.64178(16) -0.03333(16) 0.65849(10) 0.0379(3) Uani d . 1 . .
O O1 0.68874(13) 0.49686(12) -0.06702(8) 0.0347(3) Uani d . 1 . .
O O2 1.02213(12) 0.33703(12) 0.24001(7) 0.0291(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 . 1.1482(19) ?
C1 C8 . 1.4451(19) ?
C2 N2 . 1.1485(19) ?
C2 C3 . 1.4359(19) ?
C3 C4 . 1.3901(19) ?
C3 C8 . 1.4092(19) ?
C4 C5 . 1.382(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.382(2) ?
C5 H5 . 0.95 ?
C6 O1 . 1.3714(16) ?
C6 C7 . 1.3878(19) ?
C7 C8 . 1.3851(19) ?
C7 H7 . 0.95 ?
C9 C14 . 1.3822(19) ?
C9 C10 . 1.383(2) ?
C9 O1 . 1.3898(16) ?
C10 C11 . 1.387(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.385(2) ?
C11 H11 . 0.95 ?
C12 C13 . 1.379(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.3749(19) ?
C13 O2 . 1.4057(15) ?
C14 H14 . 0.95 ?
C15 N3 . 1.1420(19) ?
C15 C22 . 1.4448(19) ?
C16 N4 . 1.1449(18) ?
C16 C17 . 1.4385(19) ?
C17 C18 . 1.3891(19) ?
C17 C22 . 1.4101(19) ?
C18 C19 . 1.3789(19) ?
C18 H18 . 0.95 ?
C19 C20 . 1.3919(19) ?
C19 H19 . 0.95 ?
C20 O2 . 1.3646(16) ?
C20 C21 . 1.3899(18) ?
C21 C22 . 1.3838(19) ?
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C8 . . 176.95(15) ?
N2 C2 C3 . . 176.44(15) ?
C4 C3 C8 . . 119.25(12) ?
C4 C3 C2 . . 118.69(12) ?
C8 C3 C2 . . 122.05(12) ?
C5 C4 C3 . . 120.70(13) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C4 C5 C6 . . 119.36(13) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
O1 C6 C5 . . 117.02(12) ?
O1 C6 C7 . . 121.54(12) ?
C5 C6 C7 . . 121.33(12) ?
C8 C7 C6 . . 119.30(12) ?
C8 C7 H7 . . 120.3 ?
C6 C7 H7 . . 120.3 ?
C7 C8 C3 . . 120.04(12) ?
C7 C8 C1 . . 118.80(12) ?
C3 C8 C1 . . 121.15(12) ?
C14 C9 C10 . . 121.54(13) ?
C14 C9 O1 . . 115.25(12) ?
C10 C9 O1 . . 123.03(12) ?
C9 C10 C11 . . 118.57(13) ?
C9 C10 H10 . . 120.7 ?
C11 C10 H10 . . 120.7 ?
C12 C11 C10 . . 121.23(13) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C13 C12 C11 . . 118.04(13) ?
C13 C12 H12 . . 121.0 ?
C11 C12 H12 . . 121.0 ?
C14 C13 C12 . . 122.53(12) ?
C14 C13 O2 . . 118.23(12) ?
C12 C13 O2 . . 119.21(12) ?
C13 C14 C9 . . 118.06(13) ?
C13 C14 H14 . . 121.0 ?
C9 C14 H14 . . 121.0 ?
N3 C15 C22 . . 178.35(16) ?
N4 C16 C17 . . 179.35(16) ?
C18 C17 C22 . . 119.46(12) ?
C18 C17 C16 . . 119.84(12) ?
C22 C17 C16 . . 120.69(12) ?
C19 C18 C17 . . 120.61(12) ?
C19 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
C18 C19 C20 . . 119.41(12) ?
C18 C19 H19 . . 120.3 ?
C20 C19 H19 . . 120.3 ?
O2 C20 C21 . . 115.57(11) ?
O2 C20 C19 . . 123.23(12) ?
C21 C20 C19 . . 121.19(12) ?
C22 C21 C20 . . 119.15(12) ?
C22 C21 H21 . . 120.4 ?
C20 C21 H21 . . 120.4 ?
C21 C22 C17 . . 120.18(12) ?
C21 C22 C15 . . 120.58(12) ?
C17 C22 C15 . . 119.24(12) ?
C6 O1 C9 . . 118.75(11) ?
C20 O2 C13 . . 116.91(10) ?

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
N2 C2 C3 C4 . . . . 12.(3) ?
N2 C2 C3 C8 . . . . -167.(2) ?
C8 C3 C4 C5 . . . . 0.4(2) ?
C2 C3 C4 C5 . . . . -178.76(13) ?
C3 C4 C5 C6 . . . . 0.9(2) ?
C4 C5 C6 O1 . . . . -177.75(12) ?
C4 C5 C6 C7 . . . . -1.7(2) ?
O1 C6 C7 C8 . . . . 177.14(12) ?
C5 C6 C7 C8 . . . . 1.3(2) ?
C6 C7 C8 C3 . . . . 0.0(2) ?
C6 C7 C8 C1 . . . . -178.45(13) ?
C4 C3 C8 C7 . . . . -0.8(2) ?
C2 C3 C8 C7 . . . . 178.30(13) ?
C4 C3 C8 C1 . . . . 177.61(13) ?
C2 C3 C8 C1 . . . . -3.3(2) ?
N1 C1 C8 C7 . . . . 23.(3) ?
N1 C1 C8 C3 . . . . -156.(3) ?
C14 C9 C10 C11 . . . . 1.1(2) ?
O1 C9 C10 C11 . . . . 176.10(12) ?
C9 C10 C11 C12 . . . . -1.3(2) ?
C10 C11 C12 C13 . . . . 0.4(2) ?
C11 C12 C13 C14 . . . . 0.7(2) ?
C11 C12 C13 O2 . . . . -177.39(12) ?
C12 C13 C14 C9 . . . . -0.9(2) ?
O2 C13 C14 C9 . . . . 177.26(11) ?
C10 C9 C14 C13 . . . . -0.07(19) ?
O1 C9 C14 C13 . . . . -175.42(11) ?
N4 C16 C17 C18 . . . . 15.(14) ?
N4 C16 C17 C22 . . . . -163.(14) ?
C22 C17 C18 C19 . . . . 0.17(19) ?
C16 C17 C18 C19 . . . . -178.49(12) ?
C17 C18 C19 C20 . . . . 0.02(19) ?
C18 C19 C20 O2 . . . . 178.97(12) ?
C18 C19 C20 C21 . . . . -0.27(19) ?
O2 C20 C21 C22 . . . . -178.98(11) ?
C19 C20 C21 C22 . . . . 0.31(19) ?
C20 C21 C22 C17 . . . . -0.11(19) ?
C20 C21 C22 C15 . . . . 179.42(12) ?
C18 C17 C22 C21 . . . . -0.12(19) ?
C16 C17 C22 C21 . . . . 178.53(12) ?
C18 C17 C22 C15 . . . . -179.66(12) ?
C16 C17 C22 C15 . . . . -1.01(19) ?
N3 C15 C22 C21 . . . . -168.(6) ?
N3 C15 C22 C17 . . . . 11.(6) ?
C5 C6 O1 C9 . . . . -132.06(13) ?
C7 C6 O1 C9 . . . . 51.92(18) ?
C14 C9 O1 C6 . . . . -154.89(12) ?
C10 C9 O1 C6 . . . . 29.84(19) ?
C21 C20 O2 C13 . . . . -174.89(11) ?
C19 C20 O2 C13 . . . . 5.83(18) ?
C14 C13 O2 C20 . . . . 84.04(15) ?
C12 C13 O2 C20 . . . . -97.77(14) ?

####################################################################### 
# 
# 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 968401'
_audit_update_record             
;
2015-05-03 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            phthalonitrile
_chemical_formula_moiety         'C30 H26 N4 O2 '
_chemical_formula_sum            'C30 H26 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         474.55

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   10.2611(10)
_cell_length_b                   13.4117(12)
_cell_length_c                   18.9648(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.601(6)
_cell_angle_gamma                90
_cell_volume                     2556.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    116
_cell_measurement_theta_min      2.6662
_cell_measurement_theta_max      26.0213
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  1.00

_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            20121
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17

_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             4486
_reflns_number_gt                2931
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1277
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_number_reflns         4486
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0395P)²+1.4186P] 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          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.194
_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'

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS, 2009)'
_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  
'PLATON V1.16 (Spek, 2009), 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 0.2468(3) 0.49222(18) 0.73231(14) 0.0308(6) Uani d . 1 . .
C C2 0.2262(3) 0.70466(18) 0.73285(15) 0.0333(6) Uani d . 1 . .
C C3 0.2076(2) 0.64762(17) 0.79427(13) 0.0272(6) Uani d . 1 . .
C C4 0.1753(3) 0.69536(18) 0.85347(13) 0.0324(6) Uani d . 1 . .
H H4 0.1697 0.766 0.8542 0.039 Uiso calc R 1 . .
C C5 0.1513(3) 0.64068(17) 0.91127(13) 0.0298(6) Uani d . 1 . .
H H5 0.1288 0.6736 0.9515 0.036 Uiso calc R 1 . .
C C6 0.1602(2) 0.53738(17) 0.91027(12) 0.0237(6) Uani d . 1 . .
C C7 0.1941(2) 0.48810(17) 0.85231(12) 0.0248(6) Uani d . 1 . .
H H7 0.2019 0.4175 0.8525 0.03 Uiso calc R 1 . .
C C8 0.2166(2) 0.54308(17) 0.79411(12) 0.0240(6) Uani d . 1 . .
C C9 0.1413(2) 0.38506(16) 0.97002(12) 0.0242(6) Uani d . 1 . .
C C10 0.0332(2) 0.33046(17) 0.93616(12) 0.0266(6) Uani d . 1 . .
H H10 -0.0464 0.3629 0.9133 0.032 Uiso calc R 1 . .
C C11 0.0425(2) 0.22642(17) 0.93593(12) 0.0258(6) Uani d . 1 . .
C C12 0.1596(2) 0.18298(18) 0.97294(12) 0.0272(6) Uani d . 1 . .
H H12 0.1647 0.1123 0.9741 0.033 Uiso calc R 1 . .
C C13 0.2706(2) 0.23690(17) 1.00864(12) 0.0250(6) Uani d . 1 . .
C C14 0.2574(2) 0.34062(17) 1.00553(12) 0.0232(5) Uani d . 1 . .
C C15 0.3679(3) 0.6553(2) 1.26728(15) 0.0351(6) Uani d . 1 . .
C C16 0.1708(3) 0.50076(19) 1.23551(14) 0.0331(6) Uani d . 1 . .
C C17 0.2665(2) 0.51410(17) 1.19137(12) 0.0258(6) Uani d . 1 . .
C C18 0.2638(2) 0.45018(17) 1.13333(12) 0.0257(6) Uani d . 1 . .
H H18 0.1998 0.3983 1.1235 0.031 Uiso calc R 1 . .
C C19 0.3564(2) 0.46362(17) 1.09002(12) 0.0256(6) Uani d . 1 . .
C C20 0.4501(2) 0.53930(18) 1.10377(13) 0.0306(6) Uani d . 1 . .
H H20 0.5123 0.548 1.0733 0.037 Uiso calc R 1 . .
C C21 0.4530(3) 0.60144(18) 1.16142(14) 0.0333(6) Uani d . 1 . .
H H21 0.5174 0.6531 1.1707 0.04 Uiso calc R 1 . .
C C22 0.3625(2) 0.58972(18) 1.20659(13) 0.0298(6) Uani d . 1 . .
C C23 -0.0732(3) 0.16638(18) 0.89211(13) 0.0315(6) Uani d . 1 . .
C C24 -0.0477(3) 0.05497(19) 0.89481(14) 0.0386(7) Uani d . 1 . .
H H24A 0.0335 0.0408 0.8768 0.058 Uiso calc R 1 . .
H H24B -0.1231 0.0206 0.8647 0.058 Uiso calc R 1 . .
H H24C -0.0368 0.0316 0.9446 0.058 Uiso calc R 1 . .
C C25 -0.0916(3) 0.1989(2) 0.81245(14) 0.0436(7) Uani d . 1 . .
H H25A -0.1052 0.2712 0.8089 0.065 Uiso calc R 1 . .
H H25B -0.1693 0.165 0.784 0.065 Uiso calc R 1 . .
H H25C -0.0121 0.1811 0.794 0.065 Uiso calc R 1 . .
C C26 -0.2007(3) 0.1878(2) 0.91894(16) 0.0487(8) Uani d . 1 . .
H H26A -0.1905 0.1652 0.9689 0.073 Uiso calc R 1 . .
H H26B -0.275 0.1523 0.8888 0.073 Uiso calc R 1 . .
H H26C -0.2185 0.2596 0.9164 0.073 Uiso calc R 1 . .
C C27 0.3991(2) 0.18443(18) 1.04539(13) 0.0293(6) Uani d . 1 . .
C C28 0.5089(3) 0.2070(2) 1.00322(16) 0.0421(7) Uani d . 1 . .
H H28A 0.4791 0.1868 0.9529 0.063 Uiso calc R 1 . .
H H28B 0.5897 0.1701 1.0245 0.063 Uiso calc R 1 . .
H H28C 0.5281 0.2787 1.0054 0.063 Uiso calc R 1 . .
C C29 0.3808(3) 0.07116(18) 1.04702(15) 0.0379(7) Uani d . 1 . .
H H29A 0.3099 0.0552 1.0729 0.057 Uiso calc R 1 . .
H H29B 0.464 0.04 1.0715 0.057 Uiso calc R 1 . .
H H29C 0.3567 0.0458 0.9977 0.057 Uiso calc R 1 . .
C C30 0.4449(3) 0.2192(2) 1.12409(13) 0.0377(7) Uani d . 1 . .
H H30A 0.4736 0.289 1.1248 0.056 Uiso calc R 1 . .
H H30B 0.5194 0.1777 1.148 0.056 Uiso calc R 1 . .
H H30C 0.371 0.2131 1.1494 0.056 Uiso calc R 1 . .
N N1 0.2713(3) 0.45133(17) 0.68393(13) 0.0480(7) Uani d . 1 . .
N N2 0.2384(2) 0.75116(16) 0.68409(13) 0.0439(6) Uani d . 1 . .
N N3 0.3738(2) 0.70775(18) 1.31528(14) 0.0495(7) Uani d . 1 . .
N N4 0.0928(2) 0.48914(19) 1.27091(12) 0.0486(7) Uani d . 1 . .
O O1 0.13432(17) 0.48979(11) 0.96980(8) 0.0289(4) Uani d . 1 . .
O O2 0.36521(16) 0.40281(12) 1.03279(8) 0.0287(4) 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 . 1.140(3) ?
C1 C8 . 1.442(3) ?
C2 N2 . 1.143(3) ?
C2 C3 . 1.438(4) ?
C3 C4 . 1.389(3) ?
C3 C8 . 1.405(3) ?
C4 C5 . 1.381(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.389(3) ?
C5 H5 . 0.95 ?
C6 O1 . 1.369(3) ?
C6 C7 . 1.386(3) ?
C7 C8 . 1.385(3) ?
C7 H7 . 0.95 ?
C9 C10 . 1.375(3) ?
C9 C14 . 1.381(3) ?
C9 O1 . 1.406(3) ?
C10 C11 . 1.399(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.392(3) ?
C11 C23 . 1.534(3) ?
C12 C13 . 1.403(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.398(3) ?
C13 C27 . 1.533(3) ?
C14 O2 . 1.399(3) ?
C15 N3 . 1.142(3) ?
C15 C22 . 1.441(4) ?
C16 N4 . 1.154(3) ?
C16 C17 . 1.424(4) ?
C17 C18 . 1.391(3) ?
C17 C22 . 1.403(3) ?
C18 C19 . 1.387(3) ?
C18 H18 . 0.95 ?
C19 O2 . 1.375(3) ?
C19 C20 . 1.387(3) ?
C20 C21 . 1.370(3) ?
C20 H20 . 0.95 ?
C21 C22 . 1.393(3) ?
C21 H21 . 0.95 ?
C23 C24 . 1.516(3) ?
C23 C26 . 1.523(4) ?
C23 C25 . 1.547(3) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
C27 C29 . 1.532(3) ?
C27 C28 . 1.538(3) ?
C27 C30 . 1.544(3) ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?

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 C8 . . 179.3(3) ?
N2 C2 C3 . . 178.4(3) ?
C4 C3 C8 . . 119.2(2) ?
C4 C3 C2 . . 120.1(2) ?
C8 C3 C2 . . 120.6(2) ?
C5 C4 C3 . . 120.4(2) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 119.7(2) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
O1 C6 C7 . . 123.6(2) ?
O1 C6 C5 . . 115.5(2) ?
C7 C6 C5 . . 120.9(2) ?
C8 C7 C6 . . 119.1(2) ?
C8 C7 H7 . . 120.4 ?
C6 C7 H7 . . 120.4 ?
C7 C8 C3 . . 120.5(2) ?
C7 C8 C1 . . 119.6(2) ?
C3 C8 C1 . . 119.9(2) ?
C10 C9 C14 . . 122.2(2) ?
C10 C9 O1 . . 119.7(2) ?
C14 C9 O1 . . 118.1(2) ?
C9 C10 C11 . . 118.9(2) ?
C9 C10 H10 . . 120.5 ?
C11 C10 H10 . . 120.5 ?
C12 C11 C10 . . 117.9(2) ?
C12 C11 C23 . . 123.3(2) ?
C10 C11 C23 . . 118.7(2) ?
C11 C12 C13 . . 124.2(2) ?
C11 C12 H12 . . 117.9 ?
C13 C12 H12 . . 117.9 ?
C14 C13 C12 . . 115.5(2) ?
C14 C13 C27 . . 122.9(2) ?
C12 C13 C27 . . 121.6(2) ?
C9 C14 C13 . . 121.1(2) ?
C9 C14 O2 . . 117.6(2) ?
C13 C14 O2 . . 121.0(2) ?
N3 C15 C22 . . 179.1(3) ?
N4 C16 C17 . . 179.4(3) ?
C18 C17 C22 . . 120.6(2) ?
C18 C17 C16 . . 118.8(2) ?
C22 C17 C16 . . 120.6(2) ?
C19 C18 C17 . . 118.8(2) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
O2 C19 C18 . . 123.5(2) ?
O2 C19 C20 . . 115.4(2) ?
C18 C19 C20 . . 121.0(2) ?
C21 C20 C19 . . 119.9(2) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C20 C21 C22 . . 120.8(2) ?
C20 C21 H21 . . 119.6 ?
C22 C21 H21 . . 119.6 ?
C21 C22 C17 . . 118.8(2) ?
C21 C22 C15 . . 119.9(2) ?
C17 C22 C15 . . 121.2(2) ?
C24 C23 C26 . . 109.2(2) ?
C24 C23 C11 . . 112.9(2) ?
C26 C23 C11 . . 110.1(2) ?
C24 C23 C25 . . 107.3(2) ?
C26 C23 C25 . . 109.2(2) ?
C11 C23 C25 . . 108.1(2) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C23 C25 H25A . . 109.5 ?
C23 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C23 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C23 C26 H26A . . 109.5 ?
C23 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C23 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C29 C27 C13 . . 111.5(2) ?
C29 C27 C28 . . 108.2(2) ?
C13 C27 C28 . . 109.0(2) ?
C29 C27 C30 . . 107.2(2) ?
C13 C27 C30 . . 111.58(19) ?
C28 C27 C30 . . 109.3(2) ?
C27 C28 H28A . . 109.5 ?
C27 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C27 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C27 C29 H29A . . 109.5 ?
C27 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C27 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C27 C30 H30A . . 109.5 ?
C27 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C27 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
C6 O1 C9 . . 116.75(17) ?
C19 O2 C14 . . 118.21(17) ?

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
N2 C2 C3 C4 . . . . -47.(11) ?
N2 C2 C3 C8 . . . . 131.(11) ?
C8 C3 C4 C5 . . . . -0.5(4) ?
C2 C3 C4 C5 . . . . 177.0(2) ?
C3 C4 C5 C6 . . . . 0.3(4) ?
C4 C5 C6 O1 . . . . -179.8(2) ?
C4 C5 C6 C7 . . . . 0.6(4) ?
O1 C6 C7 C8 . . . . 179.1(2) ?
C5 C6 C7 C8 . . . . -1.4(4) ?
C6 C7 C8 C3 . . . . 1.2(4) ?
C6 C7 C8 C1 . . . . -177.6(2) ?
C4 C3 C8 C7 . . . . -0.2(4) ?
C2 C3 C8 C7 . . . . -177.8(2) ?
C4 C3 C8 C1 . . . . 178.5(2) ?
C2 C3 C8 C1 . . . . 0.9(4) ?
N1 C1 C8 C7 . . . . -30.(30) ?
N1 C1 C8 C3 . . . . 150.(30) ?
C14 C9 C10 C11 . . . . -1.8(3) ?
O1 C9 C10 C11 . . . . 179.02(19) ?
C9 C10 C11 C12 . . . . 2.7(3) ?
C9 C10 C11 C23 . . . . -174.3(2) ?
C10 C11 C12 C13 . . . . -2.1(3) ?
C23 C11 C12 C13 . . . . 174.8(2) ?
C11 C12 C13 C14 . . . . 0.3(3) ?
C11 C12 C13 C27 . . . . -177.0(2) ?
C10 C9 C14 C13 . . . . 0.1(3) ?
O1 C9 C14 C13 . . . . 179.22(19) ?
C10 C9 C14 O2 . . . . 174.6(2) ?
O1 C9 C14 O2 . . . . -6.3(3) ?
C12 C13 C14 C9 . . . . 0.7(3) ?
C27 C13 C14 C9 . . . . 178.0(2) ?
C12 C13 C14 O2 . . . . -173.65(19) ?
C27 C13 C14 O2 . . . . 3.7(3) ?
N4 C16 C17 C18 . . . . 10.(30) ?
N4 C16 C17 C22 . . . . -180.(100) ?
C22 C17 C18 C19 . . . . -1.1(3) ?
C16 C17 C18 C19 . . . . 179.5(2) ?
C17 C18 C19 O2 . . . . 177.8(2) ?
C17 C18 C19 C20 . . . . -0.1(4) ?
O2 C19 C20 C21 . . . . -177.4(2) ?
C18 C19 C20 C21 . . . . 0.7(4) ?
C19 C20 C21 C22 . . . . -0.1(4) ?
C20 C21 C22 C17 . . . . -1.1(4) ?
C20 C21 C22 C15 . . . . 179.5(2) ?
C18 C17 C22 C21 . . . . 1.7(3) ?
C16 C17 C22 C21 . . . . -178.9(2) ?
C18 C17 C22 C15 . . . . -178.9(2) ?
C16 C17 C22 C15 . . . . 0.5(4) ?
N3 C15 C22 C21 . . . . -10.(20) ?
N3 C15 C22 C17 . . . . 170.(20) ?
C12 C11 C23 C24 . . . . 1.3(3) ?
C10 C11 C23 C24 . . . . 178.1(2) ?
C12 C11 C23 C26 . . . . 123.6(3) ?
C10 C11 C23 C26 . . . . -59.6(3) ?
C12 C11 C23 C25 . . . . -117.2(3) ?
C10 C11 C23 C25 . . . . 59.6(3) ?
C14 C13 C27 C29 . . . . 174.4(2) ?
C12 C13 C27 C29 . . . . -8.4(3) ?
C14 C13 C27 C28 . . . . -66.2(3) ?
C12 C13 C27 C28 . . . . 111.0(2) ?
C14 C13 C27 C30 . . . . 54.6(3) ?
C12 C13 C27 C30 . . . . -128.2(2) ?
C7 C6 O1 C9 . . . . -1.1(3) ?
C5 C6 O1 C9 . . . . 179.4(2) ?
C10 C9 O1 C6 . . . . -83.5(3) ?
C14 C9 O1 C6 . . . . 97.3(2) ?
C18 C19 O2 C14 . . . . 16.5(3) ?
C20 C19 O2 C14 . . . . -165.4(2) ?
C9 C14 O2 C19 . . . . 69.2(3) ?
C13 C14 O2 C19 . . . . -116.3(2) ?

####################################################################### 
# 
# 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 
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data_I
_database_code_depnum_ccdc_archive 'CCDC 968402'
_audit_update_record             
;
2015-05-03 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            phthalonitrile
_chemical_formula_moiety         'C22 H10 N4 O2 '
_chemical_formula_sum            'C22 H10 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         362.34
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   20.9421(11)
_cell_length_b                   5.0644(3)
_cell_length_c                   32.8970(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3489.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    78
_cell_measurement_theta_min      3.7441
_cell_measurement_theta_max      19.2527
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  1.00

_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            41478
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_theta_min         1.24
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       33

_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             5552
_reflns_number_gt                4010
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0869
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_number_reflns         5552
_refine_ls_number_parameters     505
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0245P)²+1.1926P] 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         0.160
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(14)

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'

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS, 2009)'
_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  
'PLATON V1.16 (Spek, 2009), 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 0.38875(16) 0.6078(7) 0.53588(11) 0.0300(8) Uani d . 1 . .
C C2 0.31607(18) 0.4450(7) 0.46906(11) 0.0305(9) Uani d . 1 . .
C C3 0.37366(16) 0.3069(6) 0.47834(11) 0.0288(9) Uani d . 1 . .
C C4 0.41197(17) 0.3954(7) 0.51065(10) 0.0262(9) Uani d . 1 . .
C C5 0.47046(15) 0.2783(6) 0.51827(10) 0.0275(8) Uani d . 1 . .
H H5 0.4965 0.3387 0.54 0.033 Uiso calc R 1 . .
C C6 0.49052(16) 0.0719(6) 0.49375(10) 0.0279(9) Uani d . 1 . .
C C7 0.45176(16) -0.0240(6) 0.46288(10) 0.0273(8) Uani d . 1 . .
H H7 0.4652 -0.1708 0.4471 0.033 Uiso calc R 1 . .
C C8 0.39389(17) 0.0943(7) 0.45529(11) 0.0293(9) Uani d . 1 . .
H H8 0.3675 0.0294 0.434 0.035 Uiso calc R 1 . .
C C9 0.60020(16) 0.0997(7) 0.51014(10) 0.0268(8) Uani d . 1 . .
C C10 0.63537(16) 0.0282(7) 0.54376(10) 0.0323(9) Uani d . 1 . .
H H10 0.6223 -0.1152 0.5604 0.039 Uiso calc R 1 . .
C C11 0.69027(16) 0.1696(7) 0.55288(11) 0.0355(9) Uani d . 1 . .
H H11 0.7154 0.1208 0.5757 0.043 Uiso calc R 1 . .
C C12 0.70871(19) 0.3802(8) 0.52911(12) 0.0396(11) Uani d . 1 . .
H H12 0.7459 0.478 0.536 0.048 Uiso calc R 1 . .
C C13 0.67324(16) 0.4497(7) 0.49527(11) 0.0331(9) Uani d . 1 . .
H H13 0.686 0.5951 0.4789 0.04 Uiso calc R 1 . .
C C14 0.61983(17) 0.3086(7) 0.48540(11) 0.0290(9) Uani d . 1 . .
C C15 0.58628(16) 0.2087(6) 0.41848(11) 0.0280(8) Uani d . 1 . .
C C16 0.63308(15) 0.0179(7) 0.41405(10) 0.0283(8) Uani d . 1 . .
H H16 0.6653 -0.0013 0.4342 0.034 Uiso calc R 1 . .
C C17 0.63290(17) -0.1441(7) 0.38043(11) 0.0309(9) Uani d . 1 . .
H H17 0.6649 -0.2756 0.3775 0.037 Uiso calc R 1 . .
C C18 0.58622(16) -0.1164(7) 0.35076(11) 0.0284(9) Uani d . 1 . .
C C19 0.53957(15) 0.0798(7) 0.35516(11) 0.0280(9) Uani d . 1 . .
C C20 0.53935(16) 0.2415(7) 0.38936(10) 0.0294(8) Uani d . 1 . .
H H20 0.5073 0.3727 0.3927 0.035 Uiso calc R 1 . .
C C21 0.49104(18) 0.1097(7) 0.32461(11) 0.0325(9) Uani d . 1 . .
C C22 0.58709(17) -0.2892(8) 0.31621(12) 0.0325(9) Uani d . 1 . .
C C23 0.86817(19) 0.8948(8) 0.35315(12) 0.0299(10) Uani d . 1 . .
C C24 0.76943(16) 1.2850(7) 0.36088(11) 0.0330(9) Uani d . 1 . .
C C25 0.77067(17) 1.1086(7) 0.32665(11) 0.0269(9) Uani d . 1 . .
C C26 0.81849(16) 0.9197(6) 0.32244(10) 0.0274(8) Uani d . 1 . .
C C27 0.82010(16) 0.7546(7) 0.28893(10) 0.0284(8) Uani d . 1 . .
H H27 0.853 0.6271 0.2859 0.034 Uiso calc R 1 . .
C C28 0.77201(16) 0.7797(6) 0.25952(10) 0.0272(8) Uani d . 1 . .
C C29 0.72349(15) 0.9610(6) 0.26370(10) 0.0285(8) Uani d . 1 . .
H H29 0.6907 0.973 0.2439 0.034 Uiso calc R 1 . .
C C30 0.72333(18) 1.1263(7) 0.29740(11) 0.0293(9) Uani d . 1 . .
H H30 0.6903 1.2532 0.3004 0.035 Uiso calc R 1 . .
C C31 1.04251(18) 0.5693(7) 0.20386(12) 0.0355(10) Uani d . 1 . .
C C32 0.96580(17) 0.4019(7) 0.13680(11) 0.0367(9) Uani d . 1 . .
C C33 0.94416(18) 0.6121(7) 0.16348(11) 0.0304(10) Uani d . 1 . .
C C34 0.88469(17) 0.7236(7) 0.15779(10) 0.0328(9) Uani d . 1 . .
H H34 0.8574 0.6613 0.1368 0.039 Uiso calc R 1 . .
C C35 0.86520(16) 0.9268(6) 0.18291(10) 0.0288(9) Uani d . 1 . .
C C36 0.90518(17) 1.0273(7) 0.21258(11) 0.0320(9) Uani d . 1 . .
H H36 0.892 1.174 0.2285 0.038 Uiso calc R 1 . .
C C37 0.96376(17) 0.9146(7) 0.21887(11) 0.0324(9) Uani d . 1 . .
H H37 0.991 0.9811 0.2396 0.039 Uiso calc R 1 . .
C C38 0.98350(16) 0.7024(7) 0.19495(11) 0.0272(9) Uani d . 1 . .
C C39 0.73937(17) 0.6677(7) 0.19276(10) 0.0293(8) Uani d . 1 . .
C C40 0.75547(17) 0.8761(7) 0.16804(11) 0.0285(9) Uani d . 1 . .
C C41 0.71909(16) 0.9315(7) 0.13415(10) 0.0302(8) Uani d . 1 . .
H H41 0.7297 1.0772 0.1173 0.036 Uiso calc R 1 . .
C C42 0.66698(16) 0.7735(7) 0.12480(10) 0.0324(8) Uani d . 1 . .
H H42 0.6418 0.8102 0.1015 0.039 Uiso calc R 1 . .
C C43 0.65194(17) 0.5614(7) 0.14975(11) 0.0342(9) Uani d . 1 . .
H H43 0.6167 0.4513 0.1432 0.041 Uiso calc R 1 . .
C C44 0.68752(16) 0.5094(7) 0.18384(11) 0.0321(9) Uani d . 1 . .
H H44 0.6766 0.366 0.2011 0.038 Uiso calc R 1 . .
N N1 0.36764(14) 0.7747(6) 0.55505(9) 0.0423(8) Uani d . 1 . .
N N2 0.27110(14) 0.5650(6) 0.46168(10) 0.0412(9) Uani d . 1 . .
N N3 0.45240(16) 0.1322(6) 0.30032(10) 0.0432(9) Uani d . 1 . .
N N4 0.58883(14) -0.4324(7) 0.28940(10) 0.0429(9) Uani d . 1 . .
N N5 0.76635(14) 1.4318(7) 0.38750(9) 0.0450(9) Uani d . 1 . .
N N6 0.90658(16) 0.8749(7) 0.37778(11) 0.0427(9) Uani d . 1 . .
N N7 1.08844(15) 0.4558(6) 0.21130(11) 0.0471(9) Uani d . 1 . .
N N8 0.98177(14) 0.2345(7) 0.11547(10) 0.0512(9) Uani d . 1 . .
O O1 0.54783(10) -0.0563(4) 0.49927(7) 0.0321(6) Uani d . 1 . .
O O2 0.58304(10) 0.3744(4) 0.45136(7) 0.0320(6) Uani d . 1 . .
O O3 0.80604(11) 1.0429(4) 0.17826(7) 0.0322(6) Uani d . 1 . .
O O4 0.77697(11) 0.6088(5) 0.22705(7) 0.0326(6) 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 . 1.143(4) ?
C1 C4 . 1.443(5) ?
C2 N2 . 1.147(4) ?
C2 C3 . 1.427(5) ?
C3 C8 . 1.383(5) ?
C3 C4 . 1.405(5) ?
C4 C5 . 1.384(4) ?
C5 C6 . 1.386(5) ?
C5 H5 . 0.95 ?
C6 O1 . 1.377(4) ?
C6 C7 . 1.388(4) ?
C7 C8 . 1.375(5) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C9 C10 . 1.377(5) ?
C9 C14 . 1.396(5) ?
C9 O1 . 1.398(4) ?
C10 C11 . 1.387(5) ?
C10 H10 . 0.95 ?
C11 C12 . 1.378(5) ?
C11 H11 . 0.95 ?
C12 C13 . 1.384(5) ?
C12 H12 . 0.95 ?
C13 C14 . 1.366(5) ?
C13 H13 . 0.95 ?
C14 O2 . 1.400(4) ?
C15 O2 . 1.371(4) ?
C15 C20 . 1.382(4) ?
C15 C16 . 1.384(4) ?
C16 C17 . 1.377(5) ?
C16 H16 . 0.95 ?
C17 C18 . 1.389(5) ?
C17 H17 . 0.95 ?
C18 C19 . 1.401(5) ?
C18 C22 . 1.435(5) ?
C19 C20 . 1.391(5) ?
C19 C21 . 1.437(5) ?
C20 H20 . 0.95 ?
C21 N3 . 1.143(4) ?
C22 N4 . 1.142(4) ?
C23 N6 . 1.146(4) ?
C23 C26 . 1.455(5) ?
C24 N5 . 1.150(4) ?
C24 C25 . 1.437(5) ?
C25 C30 . 1.385(5) ?
C25 C26 . 1.392(5) ?
C26 C27 . 1.384(5) ?
C27 C28 . 1.402(4) ?
C27 H27 . 0.95 ?
C28 C29 . 1.377(4) ?
C28 O4 . 1.379(4) ?
C29 C30 . 1.389(5) ?
C29 H29 . 0.95 ?
C30 H30 . 0.95 ?
C31 N7 . 1.147(4) ?
C31 C38 . 1.438(5) ?
C32 N8 . 1.150(4) ?
C32 C33 . 1.452(5) ?
C33 C34 . 1.380(5) ?
C33 C38 . 1.400(5) ?
C34 C35 . 1.381(5) ?
C34 H34 . 0.95 ?
C35 O3 . 1.380(4) ?
C35 C36 . 1.383(5) ?
C36 C37 . 1.369(5) ?
C36 H36 . 0.95 ?
C37 C38 . 1.395(5) ?
C37 H37 . 0.95 ?
C39 C40 . 1.374(5) ?
C39 C44 . 1.381(5) ?
C39 O4 . 1.408(4) ?
C40 C41 . 1.379(5) ?
C40 O3 . 1.396(4) ?
C41 C42 . 1.388(4) ?
C41 H41 . 0.95 ?
C42 C43 . 1.388(5) ?
C42 H42 . 0.95 ?
C43 C44 . 1.372(5) ?
C43 H43 . 0.95 ?
C44 H44 . 0.95 ?

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 C4 . . 176.8(4) ?
N2 C2 C3 . . 177.4(4) ?
C8 C3 C4 . . 119.2(3) ?
C8 C3 C2 . . 121.5(3) ?
C4 C3 C2 . . 119.2(3) ?
C5 C4 C3 . . 120.4(3) ?
C5 C4 C1 . . 120.9(3) ?
C3 C4 C1 . . 118.7(3) ?
C4 C5 C6 . . 119.1(3) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
O1 C6 C5 . . 122.9(3) ?
O1 C6 C7 . . 116.2(3) ?
C5 C6 C7 . . 120.8(3) ?
C8 C7 C6 . . 119.7(3) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C7 C8 C3 . . 120.6(3) ?
C7 C8 H8 . . 119.7 ?
C3 C8 H8 . . 119.7 ?
C10 C9 C14 . . 120.6(3) ?
C10 C9 O1 . . 118.4(3) ?
C14 C9 O1 . . 120.7(3) ?
C9 C10 C11 . . 118.8(3) ?
C9 C10 H10 . . 120.6 ?
C11 C10 H10 . . 120.6 ?
C12 C11 C10 . . 120.6(3) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 C13 . . 120.2(4) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C14 C13 C12 . . 119.9(4) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C13 C14 C9 . . 119.9(3) ?
C13 C14 O2 . . 121.1(3) ?
C9 C14 O2 . . 119.0(3) ?
O2 C15 C20 . . 116.0(3) ?
O2 C15 C16 . . 123.1(3) ?
C20 C15 C16 . . 120.9(3) ?
C17 C16 C15 . . 119.9(3) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.4(3) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C17 C18 C19 . . 119.3(3) ?
C17 C18 C22 . . 119.1(3) ?
C19 C18 C22 . . 121.6(3) ?
C20 C19 C18 . . 120.2(3) ?
C20 C19 C21 . . 120.1(3) ?
C18 C19 C21 . . 119.7(3) ?
C15 C20 C19 . . 119.2(3) ?
C15 C20 H20 . . 120.4 ?
C19 C20 H20 . . 120.4 ?
N3 C21 C19 . . 179.7(4) ?
N4 C22 C18 . . 177.8(4) ?
N6 C23 C26 . . 178.9(4) ?
N5 C24 C25 . . 177.1(4) ?
C30 C25 C26 . . 119.4(3) ?
C30 C25 C24 . . 119.4(3) ?
C26 C25 C24 . . 121.2(3) ?
C27 C26 C25 . . 120.8(3) ?
C27 C26 C23 . . 118.9(3) ?
C25 C26 C23 . . 120.3(3) ?
C26 C27 C28 . . 118.5(3) ?
C26 C27 H27 . . 120.7 ?
C28 C27 H27 . . 120.7 ?
C29 C28 O4 . . 123.5(3) ?
C29 C28 C27 . . 121.4(3) ?
O4 C28 C27 . . 115.1(3) ?
C28 C29 C30 . . 118.9(3) ?
C28 C29 H29 . . 120.5 ?
C30 C29 H29 . . 120.5 ?
C25 C30 C29 . . 120.9(3) ?
C25 C30 H30 . . 119.5 ?
C29 C30 H30 . . 119.5 ?
N7 C31 C38 . . 177.7(4) ?
N8 C32 C33 . . 178.7(4) ?
C34 C33 C38 . . 119.8(3) ?
C34 C33 C32 . . 120.0(3) ?
C38 C33 C32 . . 120.2(3) ?
C33 C34 C35 . . 119.4(3) ?
C33 C34 H34 . . 120.3 ?
C35 C34 H34 . . 120.3 ?
O3 C35 C34 . . 121.1(3) ?
O3 C35 C36 . . 117.7(3) ?
C34 C35 C36 . . 121.2(3) ?
C37 C36 C35 . . 119.7(3) ?
C37 C36 H36 . . 120.1 ?
C35 C36 H36 . . 120.1 ?
C36 C37 C38 . . 120.1(3) ?
C36 C37 H37 . . 119.9 ?
C38 C37 H37 . . 119.9 ?
C37 C38 C33 . . 119.6(3) ?
C37 C38 C31 . . 120.1(3) ?
C33 C38 C31 . . 120.2(3) ?
C40 C39 C44 . . 120.9(3) ?
C40 C39 O4 . . 120.0(3) ?
C44 C39 O4 . . 119.1(3) ?
C39 C40 C41 . . 119.9(3) ?
C39 C40 O3 . . 120.6(3) ?
C41 C40 O3 . . 119.4(3) ?
C40 C41 C42 . . 119.8(3) ?
C40 C41 H41 . . 120.1 ?
C42 C41 H41 . . 120.1 ?
C43 C42 C41 . . 119.6(3) ?
C43 C42 H42 . . 120.2 ?
C41 C42 H42 . . 120.2 ?
C44 C43 C42 . . 120.6(3) ?
C44 C43 H43 . . 119.7 ?
C42 C43 H43 . . 119.7 ?
C43 C44 C39 . . 119.3(3) ?
C43 C44 H44 . . 120.4 ?
C39 C44 H44 . . 120.4 ?
C6 O1 C9 . . 116.8(2) ?
C15 O2 C14 . . 117.3(3) ?
C35 O3 C40 . . 116.8(2) ?
C28 O4 C39 . . 116.5(3) ?

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
N2 C2 C3 C8 . . . . -130.(9) ?
N2 C2 C3 C4 . . . . 47.(9) ?
C8 C3 C4 C5 . . . . 2.7(5) ?
C2 C3 C4 C5 . . . . -174.8(3) ?
C8 C3 C4 C1 . . . . -176.6(3) ?
C2 C3 C4 C1 . . . . 5.9(5) ?
N1 C1 C4 C5 . . . . -167.(7) ?
N1 C1 C4 C3 . . . . 12.(7) ?
C3 C4 C5 C6 . . . . -0.4(5) ?
C1 C4 C5 C6 . . . . 178.9(3) ?
C4 C5 C6 O1 . . . . -179.7(3) ?
C4 C5 C6 C7 . . . . -2.4(5) ?
O1 C6 C7 C8 . . . . -179.6(3) ?
C5 C6 C7 C8 . . . . 2.9(5) ?
C6 C7 C8 C3 . . . . -0.5(5) ?
C4 C3 C8 C7 . . . . -2.2(5) ?
C2 C3 C8 C7 . . . . 175.2(3) ?
C14 C9 C10 C11 . . . . 0.7(5) ?
O1 C9 C10 C11 . . . . 175.0(3) ?
C9 C10 C11 C12 . . . . 1.0(5) ?
C10 C11 C12 C13 . . . . -1.3(5) ?
C11 C12 C13 C14 . . . . -0.1(5) ?
C12 C13 C14 C9 . . . . 1.8(5) ?
C12 C13 C14 O2 . . . . 180.0(3) ?
C10 C9 C14 C13 . . . . -2.2(5) ?
O1 C9 C14 C13 . . . . -176.3(3) ?
C10 C9 C14 O2 . . . . 179.6(3) ?
O1 C9 C14 O2 . . . . 5.5(5) ?
O2 C15 C16 C17 . . . . 179.1(3) ?
C20 C15 C16 C17 . . . . -0.6(5) ?
C15 C16 C17 C18 . . . . 0.4(5) ?
C16 C17 C18 C19 . . . . 0.6(5) ?
C16 C17 C18 C22 . . . . -179.6(3) ?
C17 C18 C19 C20 . . . . -1.3(5) ?
C22 C18 C19 C20 . . . . 178.9(3) ?
C17 C18 C19 C21 . . . . -179.9(3) ?
C22 C18 C19 C21 . . . . 0.3(5) ?
O2 C15 C20 C19 . . . . -179.9(3) ?
C16 C15 C20 C19 . . . . -0.1(5) ?
C18 C19 C20 C15 . . . . 1.1(5) ?
C21 C19 C20 C15 . . . . 179.7(3) ?
C20 C19 C21 N3 . . . . -130.(100) ?
C18 C19 C21 N3 . . . . 50.(60) ?
C17 C18 C22 N4 . . . . 23.(12) ?
C19 C18 C22 N4 . . . . -157.(11) ?
N5 C24 C25 C30 . . . . -8.(9) ?
N5 C24 C25 C26 . . . . 173.(8) ?
C30 C25 C26 C27 . . . . 1.7(5) ?
C24 C25 C26 C27 . . . . -178.6(3) ?
C30 C25 C26 C23 . . . . -179.0(3) ?
C24 C25 C26 C23 . . . . 0.7(5) ?
N6 C23 C26 C27 . . . . -130.(20) ?
N6 C23 C26 C25 . . . . 50.(20) ?
C25 C26 C27 C28 . . . . -0.8(5) ?
C23 C26 C27 C28 . . . . 179.9(3) ?
C26 C27 C28 C29 . . . . -0.8(5) ?
C26 C27 C28 O4 . . . . 179.9(3) ?
O4 C28 C29 C30 . . . . -179.3(3) ?
C27 C28 C29 C30 . . . . 1.5(5) ?
C26 C25 C30 C29 . . . . -1.0(5) ?
C24 C25 C30 C29 . . . . 179.2(3) ?
C28 C29 C30 C25 . . . . -0.6(5) ?
N8 C32 C33 C34 . . . . -20.(19) ?
N8 C32 C33 C38 . . . . 160.(19) ?
C38 C33 C34 C35 . . . . 1.1(5) ?
C32 C33 C34 C35 . . . . -178.8(3) ?
C33 C34 C35 O3 . . . . -179.8(3) ?
C33 C34 C35 C36 . . . . 2.6(5) ?
O3 C35 C36 C37 . . . . 178.6(3) ?
C34 C35 C36 C37 . . . . -3.8(5) ?
C35 C36 C37 C38 . . . . 1.2(5) ?
C36 C37 C38 C33 . . . . 2.5(5) ?
C36 C37 C38 C31 . . . . -174.5(3) ?
C34 C33 C38 C37 . . . . -3.6(5) ?
C32 C33 C38 C37 . . . . 176.3(3) ?
C34 C33 C38 C31 . . . . 173.4(3) ?
C32 C33 C38 C31 . . . . -6.7(5) ?
N7 C31 C38 C37 . . . . 113.(11) ?
N7 C31 C38 C33 . . . . -64.(11) ?
C44 C39 C40 C41 . . . . 0.9(5) ?
O4 C39 C40 C41 . . . . 179.1(3) ?
C44 C39 C40 O3 . . . . 176.9(3) ?
O4 C39 C40 O3 . . . . -4.9(5) ?
C39 C40 C41 C42 . . . . -1.1(5) ?
O3 C40 C41 C42 . . . . -177.1(3) ?
C40 C41 C42 C43 . . . . 0.1(5) ?
C41 C42 C43 C44 . . . . 1.0(5) ?
C42 C43 C44 C39 . . . . -1.2(5) ?
C40 C39 C44 C43 . . . . 0.2(5) ?
O4 C39 C44 C43 . . . . -178.0(3) ?
C5 C6 O1 C9 . . . . -39.0(4) ?
C7 C6 O1 C9 . . . . 143.6(3) ?
C10 C9 O1 C6 . . . . 127.8(3) ?
C14 C9 O1 C6 . . . . -57.9(4) ?
C20 C15 O2 C14 . . . . 165.5(3) ?
C16 C15 O2 C14 . . . . -14.2(5) ?
C13 C14 O2 C15 . . . . 107.6(4) ?
C9 C14 O2 C15 . . . . -74.2(4) ?
C34 C35 O3 C40 . . . . 38.0(4) ?
C36 C35 O3 C40 . . . . -144.4(3) ?
C39 C40 O3 C35 . . . . 58.5(4) ?
C41 C40 O3 C35 . . . . -125.5(3) ?
C29 C28 O4 C39 . . . . 15.3(5) ?
C27 C28 O4 C39 . . . . -165.5(3) ?
C40 C39 O4 C28 . . . . 72.9(4) ?
C44 C39 O4 C28 . . . . -108.9(3) ?

####################################################################### 
# 
# 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 968403'
_audit_update_record             
;
2015-05-03 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            phthalonitrile
_chemical_formula_moiety         'C22 H10 N4 O2 '
_chemical_formula_sum            'C22 H10 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         362.34

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   13.7511(6)
_cell_length_b                   7.3953(3)
_cell_length_c                   17.5013(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.983(2)
_cell_angle_gamma                90
_cell_volume                     1778.70(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    130
_cell_measurement_theta_min      2.9640
_cell_measurement_theta_max      30.3251
_cell_measurement_temperature    148.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      148.(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            12440
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_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             1567
_reflns_number_gt                1404
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0980
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_number_reflns         1567
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0388P)²+1.7641P] 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         0.139
_refine_diff_density_min         -0.200
_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'

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS, 2009)'
_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  
'PLATON V1.16 (Spek, 2009), 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 0.89982(10) 1.10490(19) 0.53757(8) 0.0231(3) Uani d . 1 . .
C C2 0.74186(11) 1.0061(2) 0.62766(8) 0.0273(4) Uani d . 1 . .
C C3 0.73251(10) 0.99275(18) 0.54557(8) 0.0212(3) Uani d . 1 . .
C C4 0.64632(10) 0.93223(19) 0.51122(8) 0.0234(3) Uani d . 1 . .
H H4 0.5932 0.8985 0.5415 0.028 Uiso calc R 1 . .
C C5 0.63842(10) 0.92135(19) 0.43191(8) 0.0226(3) Uani d . 1 . .
C C6 0.71502(11) 0.9694(2) 0.38672(8) 0.0245(3) Uani d . 1 . .
H H6 0.7086 0.9612 0.3326 0.029 Uiso calc R 1 . .
C C7 0.80117(10) 1.02971(19) 0.42144(8) 0.0236(3) Uani d . 1 . .
H H7 0.854 1.063 0.3908 0.028 Uiso calc R 1 . .
C C8 0.81114(10) 1.04203(18) 0.50057(8) 0.0212(3) Uani d . 1 . .
C C9 0.52869(10) 0.8621(2) 0.32529(8) 0.0259(4) Uani d . 1 . .
C C10 0.51502(10) 0.6992(2) 0.28836(8) 0.0288(4) Uani d . 1 . .
H H10 0.5259 0.5886 0.3149 0.035 Uiso calc R 1 . .
C C11 0.51436(11) 1.0250(2) 0.28832(9) 0.0311(4) Uani d . 1 . .
H H11 0.524 1.1358 0.315 0.037 Uiso calc R 1 . .
N N1 0.96910(9) 1.15364(18) 0.56955(7) 0.0298(3) Uani d . 1 . .
N N2 0.75036(11) 1.0176(2) 0.69282(8) 0.0434(4) Uani d . 1 . .
O O1 0.55071(7) 0.85684(16) 0.40425(6) 0.0316(3) 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 . 1.1462(19) ?
C1 C8 . 1.438(2) ?
C2 N2 . 1.1456(19) ?
C2 C3 . 1.441(2) ?
C3 C4 . 1.385(2) ?
C3 C8 . 1.408(2) ?
C4 C5 . 1.391(2) ?
C4 H4 . 0.95 ?
C5 O1 . 1.3698(17) ?
C5 C6 . 1.385(2) ?
C6 C7 . 1.386(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.390(2) ?
C7 H7 . 0.95 ?
C9 C10 . 1.377(2) ?
C9 C11 . 1.378(2) ?
C9 O1 . 1.4049(17) ?
C10 C10 2_655 1.391(3) ?
C10 H10 . 0.95 ?
C11 C11 2_655 1.385(3) ?
C11 H11 . 0.95 ?

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 C8 . . 177.54(15) ?
N2 C2 C3 . . 179.18(17) ?
C4 C3 C8 . . 120.22(13) ?
C4 C3 C2 . . 120.03(13) ?
C8 C3 C2 . . 119.75(13) ?
C3 C4 C5 . . 119.22(13) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
O1 C5 C6 . . 124.42(12) ?
O1 C5 C4 . . 114.22(12) ?
C6 C5 C4 . . 121.35(13) ?
C5 C6 C7 . . 119.17(13) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
C6 C7 C8 . . 120.74(13) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C7 C8 C3 . . 119.30(13) ?
C7 C8 C1 . . 121.52(13) ?
C3 C8 C1 . . 119.18(12) ?
C10 C9 C11 . . 121.96(13) ?
C10 C9 O1 . . 117.29(13) ?
C11 C9 O1 . . 120.56(13) ?
C9 C10 C10 . 2_655 118.96(9) ?
C9 C10 H10 . . 120.5 ?
C10 C10 H10 2_655 . 120.5 ?
C9 C11 C11 . 2_655 119.07(9) ?
C9 C11 H11 . . 120.5 ?
C11 C11 H11 2_655 . 120.5 ?
C5 O1 C9 . . 119.67(11) ?

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
N2 C2 C3 C4 . . . . -170.(100) ?
N2 C2 C3 C8 . . . . 6.(14) ?
C8 C3 C4 C5 . . . . -0.2(2) ?
C2 C3 C4 C5 . . . . 179.60(13) ?
C3 C4 C5 O1 . . . . 178.91(13) ?
C3 C4 C5 C6 . . . . 0.1(2) ?
O1 C5 C6 C7 . . . . -178.70(13) ?
C4 C5 C6 C7 . . . . -0.1(2) ?
C5 C6 C7 C8 . . . . 0.0(2) ?
C6 C7 C8 C3 . . . . -0.1(2) ?
C6 C7 C8 C1 . . . . -179.76(13) ?
C4 C3 C8 C7 . . . . 0.2(2) ?
C2 C3 C8 C7 . . . . -179.62(13) ?
C4 C3 C8 C1 . . . . 179.85(13) ?
C2 C3 C8 C1 . . . . 0.1(2) ?
N1 C1 C8 C7 . . . . -175.(4) ?
N1 C1 C8 C3 . . . . 5.(4) ?
C11 C9 C10 C10 . . . 2_655 -0.6(3) ?
O1 C9 C10 C10 . . . 2_655 174.56(16) ?
C10 C9 C11 C11 . . . 2_655 -0.2(3) ?
O1 C9 C11 C11 . . . 2_655 -175.21(17) ?
C6 C5 O1 C9 . . . . -9.8(2) ?
C4 C5 O1 C9 . . . . 171.47(12) ?
C10 C9 O1 C5 . . . . 116.78(15) ?
C11 C9 O1 C5 . . . . -67.99(19) ?

