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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5b
_database_code_depnum_ccdc_archive 'CCDC 1486351'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2,3-dicyano-5,6-bis-4-(benzyloxy)phenyl pyrazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 N4 O2'
_chemical_formula_sum            'C32 H22 N4 O2'
_chemical_formula_weight         494.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.2968(3)
_cell_length_b                   11.2161(5)
_cell_length_c                   27.6291(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.453(3)
_cell_angle_gamma                90
_cell_volume                     2549.38(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3006
_cell_measurement_theta_min      3.470
_cell_measurement_theta_max      27.460

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;    
CrysAlisPro, Agilent Technologies, 2014
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_reflns_number            14332
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.876
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4651
_reflns_number_gt                3332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlis Pro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies, 2014)'
_computing_structure_solution    'SIR2014 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.1801P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4651
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4098(2) 0.66534(18) 0.26715(7) 0.0313(5) Uani 1 1 d . . . . .
C2 C 0.41528(19) 0.54629(16) 0.28694(6) 0.0253(4) Uani 1 1 d . . . . .
C3 C 0.37068(18) 0.42369(15) 0.35014(6) 0.0223(4) Uani 1 1 d . . . . .
C4 C 0.33224(18) 0.41817(14) 0.40068(6) 0.0207(4) Uani 1 1 d . . . . .
C5 C 0.42786(19) 0.35618(14) 0.43728(6) 0.0235(4) Uani 1 1 d . . . . .
H5 H 0.5161 0.3094 0.4293 0.028 Uiso 1 1 calc R U . . .
C6 C 0.39693(19) 0.36136(15) 0.48511(6) 0.0246(4) Uani 1 1 d . . . . .
H6 H 0.4639 0.3190 0.5098 0.030 Uiso 1 1 calc R U . . .
C7 C 0.26732(19) 0.42880(15) 0.49678(6) 0.0233(4) Uani 1 1 d . . . . .
C8 C 0.16955(19) 0.49007(15) 0.46027(6) 0.0251(4) Uani 1 1 d . . . . .
H8 H 0.0796 0.5352 0.4681 0.030 Uiso 1 1 calc R U . . .
C9 C 0.20259(19) 0.48545(15) 0.41320(6) 0.0229(4) Uani 1 1 d . . . . .
H9 H 0.1363 0.5287 0.3886 0.028 Uiso 1 1 calc R U . . .
C10 C 0.31541(19) 0.38326(16) 0.58273(6) 0.0259(4) Uani 1 1 d . . . . .
H10A H 0.4304 0.4091 0.5858 0.031 Uiso 1 1 calc R U . . .
H10B H 0.3111 0.2955 0.5788 0.031 Uiso 1 1 calc R U . . .
C11 C 0.23966(19) 0.42023(16) 0.62673(6) 0.0246(4) Uani 1 1 d . . . . .
C12 C 0.1952(2) 0.33687(17) 0.65955(6) 0.0329(5) Uani 1 1 d . . . . .
H12 H 0.2149 0.2546 0.6546 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1222(2) 0.37229(19) 0.69971(7) 0.0379(5) Uani 1 1 d . . . . .
H13 H 0.0924 0.3144 0.7220 0.046 Uiso 1 1 calc R U . . .
C14 C 0.0929(2) 0.49133(18) 0.70718(7) 0.0350(5) Uani 1 1 d . . . . .
H14 H 0.0421 0.5156 0.7345 0.042 Uiso 1 1 calc R U . . .
C15 C 0.1372(2) 0.57507(18) 0.67498(6) 0.0321(5) Uani 1 1 d . . . . .
H15 H 0.1181 0.6572 0.6803 0.039 Uiso 1 1 calc R U . . .
C16 C 0.20975(19) 0.53997(16) 0.63482(6) 0.0277(4) Uani 1 1 d . . . . .
H16 H 0.2392 0.5983 0.6126 0.033 Uiso 1 1 calc R U . . .
C17 C 0.5484(2) 0.46755(17) 0.21877(7) 0.0310(4) Uani 1 1 d . . . . .
C18 C 0.47894(19) 0.45141(17) 0.26365(6) 0.0270(4) Uani 1 1 d . . . . .
C19 C 0.41927(18) 0.32397(15) 0.32341(6) 0.0242(4) Uani 1 1 d . . . . .
C20 C 0.40766(19) 0.19995(15) 0.33989(6) 0.0244(4) Uani 1 1 d . . . . .
C21 C 0.5286(2) 0.11807(16) 0.33321(6) 0.0304(4) Uani 1 1 d . . . . .
H21 H 0.6196 0.1428 0.3181 0.036 Uiso 1 1 calc R U . . .
C22 C 0.5182(2) 0.00199(17) 0.34816(7) 0.0360(5) Uani 1 1 d . . . . .
H22 H 0.6018 -0.0530 0.3435 0.043 Uiso 1 1 calc R U . . .
C23 C 0.3857(2) -0.03503(16) 0.37013(7) 0.0315(5) Uani 1 1 d . . . . .
C24 C 0.2622(2) 0.04454(16) 0.37638(6) 0.0299(4) Uani 1 1 d . . . . .
H24 H 0.1702 0.0191 0.3909 0.036 Uiso 1 1 calc R U . . .
C25 C 0.2742(2) 0.16118(15) 0.36133(6) 0.0267(4) Uani 1 1 d . . . . .
H25 H 0.1900 0.2159 0.3657 0.032 Uiso 1 1 calc R U . . .
C26 C 0.2431(2) -0.20029(17) 0.39936(8) 0.0454(5) Uani 1 1 d . . . . .
H26A H 0.2481 -0.2882 0.3968 0.054 Uiso 1 1 calc R U . . .
H26B H 0.1497 -0.1727 0.3761 0.054 Uiso 1 1 calc R U . . .
C27 C 0.2124(2) -0.16817(16) 0.45028(8) 0.0382(5) Uani 1 1 d . . . . .
C28 C 0.3307(2) -0.11911(17) 0.48429(8) 0.0401(5) Uani 1 1 d . . . . .
H28 H 0.4344 -0.1007 0.4752 0.048 Uiso 1 1 calc R U . . .
C29 C 0.2997(3) -0.09660(19) 0.53126(8) 0.0469(6) Uani 1 1 d . . . . .
H29 H 0.3825 -0.0631 0.5542 0.056 Uiso 1 1 calc R U . . .
C30 C 0.1505(3) -0.12199(19) 0.54536(9) 0.0536(6) Uani 1 1 d . . . . .
H30 H 0.1298 -0.1065 0.5778 0.064 Uiso 1 1 calc R U . . .
C31 C 0.0313(3) -0.1703(2) 0.51165(10) 0.0626(7) Uani 1 1 d . . . . .
H31 H -0.0725 -0.1883 0.5208 0.075 Uiso 1 1 calc R U . . .
C32 C 0.0624(3) -0.1924(2) 0.46455(9) 0.0533(6) Uani 1 1 d . . . . .
H32 H -0.0210 -0.2250 0.4415 0.064 Uiso 1 1 calc R U . . .
N1 N 0.4075(2) 0.76013(16) 0.25148(6) 0.0459(5) Uani 1 1 d . . . . .
N2 N 0.60217(18) 0.48009(16) 0.18315(6) 0.0439(5) Uani 1 1 d . . . . .
N3 N 0.36347(15) 0.53308(13) 0.33041(5) 0.0242(3) Uani 1 1 d . . . . .
N4 N 0.47786(16) 0.34011(13) 0.28106(5) 0.0263(4) Uani 1 1 d . . . . .
O1 O 0.22265(13) 0.44024(11) 0.54206(4) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.38910(16) -0.15122(11) 0.38502(5) 0.0442(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.147(2) . ?
C1 C2 1.441(3) . ?
C2 N3 1.335(2) . ?
C2 C18 1.383(2) . ?
C3 N3 1.341(2) . ?
C3 C19 1.427(2) . ?
C3 C4 1.473(2) . ?
C4 C5 1.388(2) . ?
C4 C9 1.394(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 O1 1.3562(19) . ?
C7 C8 1.391(2) . ?
C8 C9 1.364(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 O1 1.4280(19) . ?
C10 C11 1.498(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.385(2) . ?
C11 C16 1.389(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N2 1.141(2) . ?
C17 C18 1.445(2) . ?
C18 N4 1.338(2) . ?
C19 N4 1.336(2) . ?
C19 C20 1.471(2) . ?
C20 C21 1.390(2) . ?
C20 C25 1.391(2) . ?
C21 C22 1.372(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 O2 1.366(2) . ?
C23 C24 1.386(2) . ?
C24 C25 1.380(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 O2 1.432(2) . ?
C26 C27 1.506(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C32 1.380(3) . ?
C27 C28 1.382(3) . ?
C28 C29 1.379(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.375(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.378(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 179.2(2) . . ?
N3 C2 C18 121.33(16) . . ?
N3 C2 C1 116.49(16) . . ?
C18 C2 C1 122.09(16) . . ?
N3 C3 C19 120.50(15) . . ?
N3 C3 C4 114.83(15) . . ?
C19 C3 C4 124.62(15) . . ?
C5 C4 C9 118.47(15) . . ?
C5 C4 C3 122.54(14) . . ?
C9 C4 C3 118.78(15) . . ?
C6 C5 C4 121.13(15) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.46(16) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
O1 C7 C6 125.39(15) . . ?
O1 C7 C8 114.75(14) . . ?
C6 C7 C8 119.86(15) . . ?
C9 C8 C7 120.13(15) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 120.94(16) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
O1 C10 C11 105.95(13) . . ?
O1 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
O1 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C12 C11 C16 118.61(16) . . ?
C12 C11 C10 121.32(16) . . ?
C16 C11 C10 120.06(16) . . ?
C11 C12 C13 120.69(18) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.05(18) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 119.82(17) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.26(18) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.57(17) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N2 C17 C18 179.5(2) . . ?
N4 C18 C2 121.97(16) . . ?
N4 C18 C17 116.58(16) . . ?
C2 C18 C17 121.45(17) . . ?
N4 C19 C3 120.42(16) . . ?
N4 C19 C20 116.44(15) . . ?
C3 C19 C20 123.15(15) . . ?
C21 C20 C25 118.56(16) . . ?
C21 C20 C19 120.42(15) . . ?
C25 C20 C19 121.01(15) . . ?
C22 C21 C20 120.80(17) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 120.04(17) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
O2 C23 C24 124.31(17) . . ?
O2 C23 C22 115.52(16) . . ?
C24 C23 C22 120.16(17) . . ?
C25 C24 C23 119.28(17) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C20 121.15(16) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?
O2 C26 C27 114.72(16) . . ?
O2 C26 H26A 108.6 . . ?
C27 C26 H26A 108.6 . . ?
O2 C26 H26B 108.6 . . ?
C27 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C32 C27 C28 118.1(2) . . ?
C32 C27 C26 119.21(19) . . ?
C28 C27 C26 122.64(18) . . ?
C29 C28 C27 120.69(19) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C30 C29 C28 120.9(2) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 118.9(2) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C30 C31 C32 120.1(2) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C27 C32 C31 121.3(2) . . ?
C27 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C2 N3 C3 117.69(15) . . ?
C19 N4 C18 117.48(15) . . ?
C7 O1 C10 119.98(12) . . ?
C23 O2 C26 117.69(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C3 C4 C5 -132.79(16) . . . . ?
C19 C3 C4 C5 44.6(2) . . . . ?
N3 C3 C4 C9 41.9(2) . . . . ?
C19 C3 C4 C9 -140.71(16) . . . . ?
C9 C4 C5 C6 -0.5(2) . . . . ?
C3 C4 C5 C6 174.20(15) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 O1 179.17(16) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
O1 C7 C8 C9 179.90(15) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C7 C8 C9 C4 1.1(3) . . . . ?
C5 C4 C9 C8 -0.3(2) . . . . ?
C3 C4 C9 C8 -175.23(15) . . . . ?
O1 C10 C11 C12 128.59(16) . . . . ?
O1 C10 C11 C16 -50.18(19) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C10 C11 C12 C13 -178.74(16) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C11 -0.5(2) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
C10 C11 C16 C15 178.93(14) . . . . ?
N3 C2 C18 N4 6.4(2) . . . . ?
C1 C2 C18 N4 -177.21(15) . . . . ?
N3 C2 C18 C17 -174.39(15) . . . . ?
C1 C2 C18 C17 2.0(2) . . . . ?
N3 C3 C19 N4 8.5(2) . . . . ?
C4 C3 C19 N4 -168.69(15) . . . . ?
N3 C3 C19 C20 -171.05(14) . . . . ?
C4 C3 C19 C20 11.7(2) . . . . ?
N4 C19 C20 C21 38.7(2) . . . . ?
C3 C19 C20 C21 -141.74(16) . . . . ?
N4 C19 C20 C25 -139.75(16) . . . . ?
C3 C19 C20 C25 39.9(2) . . . . ?
C25 C20 C21 C22 -1.1(3) . . . . ?
C19 C20 C21 C22 -179.53(16) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C21 C22 C23 O2 -178.09(16) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
O2 C23 C24 C25 177.82(16) . . . . ?
C22 C23 C24 C25 -1.2(3) . . . . ?
C23 C24 C25 C20 0.2(3) . . . . ?
C21 C20 C25 C24 0.9(3) . . . . ?
C19 C20 C25 C24 179.32(16) . . . . ?
O2 C26 C27 C32 168.44(17) . . . . ?
O2 C26 C27 C28 -14.1(3) . . . . ?
C32 C27 C28 C29 0.8(3) . . . . ?
C26 C27 C28 C29 -176.72(19) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C31 -0.2(3) . . . . ?
C29 C30 C31 C32 0.0(3) . . . . ?
C28 C27 C32 C31 -1.0(3) . . . . ?
C26 C27 C32 C31 176.6(2) . . . . ?
C30 C31 C32 C27 0.6(4) . . . . ?
C18 C2 N3 C3 -2.0(2) . . . . ?
C1 C2 N3 C3 -178.55(14) . . . . ?
C19 C3 N3 C2 -5.2(2) . . . . ?
C4 C3 N3 C2 172.32(13) . . . . ?
C3 C19 N4 C18 -4.2(2) . . . . ?
C20 C19 N4 C18 175.44(14) . . . . ?
C2 C18 N4 C19 -3.0(2) . . . . ?
C17 C18 N4 C19 177.75(14) . . . . ?
C6 C7 O1 C10 2.2(2) . . . . ?
C8 C7 O1 C10 -178.85(15) . . . . ?
C11 C10 O1 C7 176.55(14) . . . . ?
C24 C23 O2 C26 12.5(3) . . . . ?
C22 C23 O2 C26 -168.45(17) . . . . ?
C27 C26 O2 C23 -79.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O1 0.95 2.50 3.3391(19) 147.0 3_566
C22 H22 N2 0.95 2.68 3.382(2) 131.2 2_645

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5c
_database_code_depnum_ccdc_archive 'CCDC 1486352'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2,3-Dicyano-5,6-bis-4-[3,5-bis(benzyloxy)benzyloxy]phenyl pyrazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C60 H46 N4 O6, 2(C H2 Cl2)'
_chemical_formula_sum            'C62 H50 Cl4 N4 O6'
_chemical_formula_weight         1088.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   23.8249(7)
_cell_length_b                   15.5643(4)
_cell_length_c                   16.2565(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.473(3)
_cell_angle_gamma                90
_cell_volume                     5348.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5376
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      75.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             2264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.474
_shelx_estimated_absorpt_T_min   0.438
_shelx_estimated_absorpt_T_max   0.637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.210
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies, 2014
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1996
_diffrn_reflns_number            12425
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.526
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4913
_reflns_number_gt                4091
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlis Pro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies, 2014)'
_computing_structure_solution    'SIR2014 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1761P)²+4.5777P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4913
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.2487
_refine_ls_wR_factor_gt          0.2337
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.06269(15) 0.94847(18) 0.7018(2) 0.0525(7) Uani 1 1 d . . . . .
N2 N 0.04011(10) 0.73160(14) 0.70890(14) 0.0320(5) Uani 1 1 d . . . . .
O1 O 0.09305(9) 0.38053(13) 0.57670(14) 0.0399(5) Uani 1 1 d . . . . .
O2 O 0.11758(10) 0.02472(13) 0.46603(14) 0.0389(5) Uani 1 1 d . . . . .
O3 O 0.18937(9) 0.28103(12) 0.38757(13) 0.0362(5) Uani 1 1 d . . . . .
C1 C 0.04485(14) 0.88400(18) 0.71443(19) 0.0388(6) Uani 1 1 d . . . . .
C2 C 0.02130(13) 0.80434(17) 0.73150(17) 0.0330(6) Uani 1 1 d . . . . .
C3 C 0.01881(12) 0.65735(16) 0.72589(16) 0.0293(5) Uani 1 1 d . . . . .
C4 C 0.03622(13) 0.58032(16) 0.69038(17) 0.0311(5) Uani 1 1 d . . . . .
C5 C -0.00530(13) 0.51274(18) 0.64775(19) 0.0340(6) Uani 1 1 d . . . . .
H5 H -0.0459 0.5132 0.6453 0.041 Uiso 1 1 calc R U . . .
C6 C 0.01160(13) 0.44480(18) 0.60872(19) 0.0353(6) Uani 1 1 d . . . . .
H6 H -0.0174 0.3993 0.5793 0.042 Uiso 1 1 calc R U . . .
C7 C 0.07128(13) 0.44338(17) 0.61274(18) 0.0340(6) Uani 1 1 d . . . . .
C8 C 0.11356(13) 0.51030(19) 0.6560(2) 0.0400(6) Uani 1 1 d . . . . .
H8 H 0.1545 0.5092 0.6597 0.048 Uiso 1 1 calc R U . . .
C9 C 0.09599(13) 0.57796(18) 0.6936(2) 0.0372(6) Uani 1 1 d . . . . .
H9 H 0.1248 0.6238 0.7221 0.045 Uiso 1 1 calc R U . . .
C10 C 0.05364(13) 0.30755(17) 0.53427(19) 0.0351(6) Uani 1 1 d . . . . .
H10A H 0.0125 0.3261 0.4834 0.042 Uiso 1 1 calc R U . . .
H10B H 0.0457 0.2755 0.5804 0.042 Uiso 1 1 calc R U . . .
C11 C 0.08839(12) 0.25162(18) 0.49678(17) 0.0327(6) Uani 1 1 d . . . . .
C12 C 0.08387(12) 0.16251(18) 0.50013(17) 0.0332(6) Uani 1 1 d . . . . .
H12 H 0.0592 0.1366 0.5256 0.040 Uiso 1 1 calc R U . . .
C13 C 0.11643(12) 0.11236(17) 0.46515(17) 0.0329(6) Uani 1 1 d . . . . .
C14 C 0.15221(12) 0.14908(17) 0.42715(17) 0.0321(6) Uani 1 1 d . . . . .
H14 H 0.1742 0.1139 0.4037 0.038 Uiso 1 1 calc R U . . .
C15 C 0.15548(12) 0.23819(17) 0.42383(16) 0.0311(5) Uani 1 1 d . . . . .
C16 C 0.12316(13) 0.28944(17) 0.45784(17) 0.0329(6) Uani 1 1 d . . . . .
H16 H 0.1249 0.3502 0.4544 0.040 Uiso 1 1 calc R U . . .
C17 C 0.07755(14) -0.02050(19) 0.4956(2) 0.0386(6) Uani 1 1 d . . . . .
H17A H 0.0328 -0.0040 0.4572 0.046 Uiso 1 1 calc R U . . .
H17B H 0.0897 -0.0073 0.5613 0.046 Uiso 1 1 calc R U . . .
C18 C 0.08677(14) -0.11410(19) 0.4840(2) 0.0420(7) Uani 1 1 d . . . . .
C19 C 0.1221(2) -0.1659(2) 0.5596(3) 0.0587(9) Uani 1 1 d . . . . .
H19 H 0.1384 -0.1428 0.6204 0.070 Uiso 1 1 calc R U . . .
C20 C 0.1340(2) -0.2511(3) 0.5482(4) 0.0719(12) Uani 1 1 d . . . . .
H20 H 0.1580 -0.2861 0.6007 0.086 Uiso 1 1 calc R U . . .
C21 C 0.1113(2) -0.2843(2) 0.4614(4) 0.0716(13) Uani 1 1 d . . . . .
H21 H 0.1204 -0.3423 0.4535 0.086 Uiso 1 1 calc R U . . .
C22 C 0.0753(2) -0.2348(3) 0.3847(4) 0.0697(12) Uani 1 1 d . . . . .
H22 H 0.0588 -0.2590 0.3244 0.084 Uiso 1 1 calc R U . . .
C23 C 0.06313(18) -0.1492(2) 0.3960(3) 0.0558(8) Uani 1 1 d . . . . .
H23 H 0.0385 -0.1148 0.3432 0.067 Uiso 1 1 calc R U . . .
C24 C 0.22159(13) 0.23107(18) 0.35040(19) 0.0359(6) Uani 1 1 d . . . . .
H24A H 0.1909 0.1953 0.2990 0.043 Uiso 1 1 calc R U . . .
H24B H 0.2518 0.1922 0.3988 0.043 Uiso 1 1 calc R U . . .
C25 C 0.25680(13) 0.2881(2) 0.31520(18) 0.0380(6) Uani 1 1 d . . . . .
C26 C 0.29015(15) 0.2493(2) 0.2747(2) 0.0486(7) Uani 1 1 d . . . . .
H26 H 0.2900 0.1885 0.2694 0.058 Uiso 1 1 calc R U . . .
C27 C 0.32404(17) 0.2994(3) 0.2417(3) 0.0570(9) Uani 1 1 d . . . . .
H27 H 0.3466 0.2723 0.2135 0.068 Uiso 1 1 calc R U . . .
C28 C 0.32511(17) 0.3866(3) 0.2493(2) 0.0567(9) Uani 1 1 d . . . . .
H28 H 0.3485 0.4202 0.2270 0.068 Uiso 1 1 calc R U . . .
C29 C 0.29176(15) 0.4260(2) 0.2899(2) 0.0503(8) Uani 1 1 d . . . . .
H29 H 0.2918 0.4869 0.2945 0.060 Uiso 1 1 calc R U . . .
C30 C 0.25814(14) 0.3768(2) 0.3239(2) 0.0414(7) Uani 1 1 d . . . . .
H30 H 0.2362 0.4039 0.3529 0.050 Uiso 1 1 calc R U . . .
C1A C 0.2495(2) 0.5775(3) 0.4995(3) 0.0647(10) Uani 1 1 d . . . . .
H1A1 H 0.2931 0.5576 0.5177 0.078 Uiso 1 1 calc R U . . .
H1A2 H 0.2519 0.6333 0.5301 0.078 Uiso 1 1 calc R U . . .
Cl1A Cl 0.20989(5) 0.50191(6) 0.53463(7) 0.0650(3) Uani 1 1 d . . . . .
Cl2A Cl 0.20779(9) 0.58967(11) 0.37837(10) 0.1119(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.145(4) . ?
N2 C2 1.330(4) . ?
N2 C3 1.341(3) . ?
O1 C7 1.360(3) . ?
O1 C10 1.432(3) . ?
O2 C13 1.364(3) . ?
O2 C17 1.436(3) . ?
O3 C15 1.372(3) . ?
O3 C24 1.410(3) . ?
C1 C2 1.440(4) . ?
C2 C2 1.398(6) 2_556 ?
C3 C3 1.437(5) 2_556 ?
C3 C4 1.471(4) . ?
C4 C5 1.390(4) . ?
C4 C9 1.401(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(4) . ?
C8 C9 1.376(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.510(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.385(4) . ?
C11 C12 1.394(4) . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C14 C15 1.392(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.498(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C23 1.385(5) . ?
C18 C19 1.385(5) . ?
C19 C20 1.387(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.359(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(6) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.504(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.383(4) . ?
C25 C30 1.386(4) . ?
C26 C27 1.396(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.362(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.388(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C1A Cl1A 1.759(4) . ?
C1A Cl2A 1.760(5) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 C3 118.0(2) . . ?
C7 O1 C10 118.9(2) . . ?
C13 O2 C17 118.7(2) . . ?
C15 O3 C24 117.4(2) . . ?
N1 C1 C2 178.2(3) . . ?
N2 C2 C2 121.51(15) . 2_556 ?
N2 C2 C1 118.0(3) . . ?
C2 C2 C1 120.51(17) 2_556 . ?
N2 C3 C3 120.18(15) . 2_556 ?
N2 C3 C4 114.8(2) . . ?
C3 C3 C4 125.02(14) 2_556 . ?
C5 C4 C9 118.4(2) . . ?
C5 C4 C3 123.2(2) . . ?
C9 C4 C3 118.2(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
O1 C7 C6 125.1(2) . . ?
O1 C7 C8 115.1(2) . . ?
C6 C7 C8 119.8(2) . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
O1 C10 C11 107.0(2) . . ?
O1 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O1 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
C16 C11 C12 120.9(2) . . ?
C16 C11 C10 119.6(2) . . ?
C12 C11 C10 119.4(2) . . ?
C13 C12 C11 118.3(2) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
O2 C13 C14 113.8(2) . . ?
O2 C13 C12 124.6(2) . . ?
C14 C13 C12 121.6(2) . . ?
C13 C14 C15 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
O3 C15 C16 115.9(2) . . ?
O3 C15 C14 123.8(2) . . ?
C16 C15 C14 120.4(2) . . ?
C11 C16 C15 119.8(3) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
O2 C17 C18 106.0(2) . . ?
O2 C17 H17A 110.5 . . ?
C18 C17 H17A 110.5 . . ?
O2 C17 H17B 110.5 . . ?
C18 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
C23 C18 C19 118.6(3) . . ?
C23 C18 C17 120.1(3) . . ?
C19 C18 C17 121.2(3) . . ?
C18 C19 C20 121.1(4) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 119.7(4) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.7(4) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.8(4) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 120.2(4) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
O3 C24 C25 110.3(2) . . ?
O3 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
O3 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C26 C25 C30 119.5(3) . . ?
C26 C25 C24 117.8(3) . . ?
C30 C25 C24 122.7(3) . . ?
C25 C26 C27 120.0(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 119.6(3) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C28 C29 C30 120.3(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C25 C30 C29 119.8(3) . . ?
C25 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
Cl1A C1A Cl2A 109.0(3) . . ?
Cl1A C1A H1A1 109.9 . . ?
Cl2A C1A H1A1 109.9 . . ?
Cl1A C1A H1A2 109.9 . . ?
Cl2A C1A H1A2 109.9 . . ?
H1A1 C1A H1A2 108.3 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C2 C2 -2.5(4) . . . 2_556 ?
C3 N2 C2 C1 179.2(2) . . . . ?
C2 N2 C3 C3 -5.1(4) . . . 2_556 ?
C2 N2 C3 C4 174.0(2) . . . . ?
N2 C3 C4 C5 -138.6(3) . . . . ?
C3 C3 C4 C5 40.4(4) 2_556 . . . ?
N2 C3 C4 C9 36.6(3) . . . . ?
C3 C3 C4 C9 -144.4(3) 2_556 . . . ?
C9 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 C6 174.7(2) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C10 O1 C7 C6 -2.7(4) . . . . ?
C10 O1 C7 C8 177.5(2) . . . . ?
C5 C6 C7 O1 -179.7(3) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
O1 C7 C8 C9 178.9(3) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C7 C8 C9 C4 1.0(5) . . . . ?
C5 C4 C9 C8 -0.4(4) . . . . ?
C3 C4 C9 C8 -175.8(3) . . . . ?
C7 O1 C10 C11 177.2(2) . . . . ?
O1 C10 C11 C16 -37.6(3) . . . . ?
O1 C10 C11 C12 143.8(2) . . . . ?
C16 C11 C12 C13 1.4(4) . . . . ?
C10 C11 C12 C13 -180.0(2) . . . . ?
C17 O2 C13 C14 -174.2(2) . . . . ?
C17 O2 C13 C12 7.0(4) . . . . ?
C11 C12 C13 O2 178.3(2) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
O2 C13 C14 C15 -179.0(2) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C24 O3 C15 C16 -178.5(2) . . . . ?
C24 O3 C15 C14 1.1(3) . . . . ?
C13 C14 C15 O3 -179.9(2) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C12 C11 C16 C15 -1.8(4) . . . . ?
C10 C11 C16 C15 179.6(2) . . . . ?
O3 C15 C16 C11 -179.2(2) . . . . ?
C14 C15 C16 C11 1.2(4) . . . . ?
C13 O2 C17 C18 177.0(2) . . . . ?
O2 C17 C18 C23 -70.8(4) . . . . ?
O2 C17 C18 C19 105.2(3) . . . . ?
C23 C18 C19 C20 0.4(5) . . . . ?
C17 C18 C19 C20 -175.7(3) . . . . ?
C18 C19 C20 C21 0.6(6) . . . . ?
C19 C20 C21 C22 -1.6(6) . . . . ?
C20 C21 C22 C23 1.5(6) . . . . ?
C19 C18 C23 C22 -0.5(5) . . . . ?
C17 C18 C23 C22 175.6(3) . . . . ?
C21 C22 C23 C18 -0.4(6) . . . . ?
C15 O3 C24 C25 -179.2(2) . . . . ?
O3 C24 C25 C26 -178.8(2) . . . . ?
O3 C24 C25 C30 2.8(4) . . . . ?
C30 C25 C26 C27 -1.0(5) . . . . ?
C24 C25 C26 C27 -179.5(3) . . . . ?
C25 C26 C27 C28 0.4(5) . . . . ?
C26 C27 C28 C29 -0.4(5) . . . . ?
C27 C28 C29 C30 1.0(5) . . . . ?
C26 C25 C30 C29 1.5(4) . . . . ?
C24 C25 C30 C29 179.9(3) . . . . ?
C28 C29 C30 C25 -1.5(5) . . . . ?

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.105

