# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_a
_database_code_depnum_ccdc_archive 'CCDC 1497296'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1,4-Diketo-2,5-dibutyl-3,6-di(p-chlorophenyl)pyrrolo[3,4,c]pyrrole
_chemical_name_common            BDPP
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 Cl2 N2 O2'
_chemical_formula_sum            'C26 H26 Cl2 N2 O2'
_chemical_formula_weight         469.39

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '
_symmetry_space_group_name_Hall  '-C 2yc '

loop_
_symmetry_equiv_pos_as_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                   22.809(6)
_cell_length_b                   17.989(4)
_cell_length_c                   15.485(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 131.863(3)
_cell_angle_gamma                90.00
_cell_volume                     4732(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4039
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            Red

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9260
_exptl_absorpt_correction_T_max  0.9480
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?

_diffrn_reflns_number            12983
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4639
_reflns_number_gt                3270
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0505P)²+7.6172P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4639
_refine_ls_number_parameters     291
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15213(10) 0.70932(10) 0.99550(16) 0.0573(5) Uani 1 1 d . . .
O2 O -0.13891(11) 0.53510(10) 0.73270(18) 0.0620(5) Uani 1 1 d . . .
C1 C 0.05213(17) 0.30524(15) 0.9035(2) 0.0559(7) Uani 1 1 d . . .
C2 C 0.10011(17) 0.34120(16) 0.8935(3) 0.0591(7) Uani 1 1 d . . .
H2 H 0.1308 0.3141 0.8851 0.071 Uiso 1 1 calc R . .
C3 C 0.10289(16) 0.41746(15) 0.8959(2) 0.0537(7) Uani 1 1 d . . .
H3 H 0.1353 0.4420 0.8886 0.064 Uiso 1 1 calc R . .
C4 C 0.05770(14) 0.45819(14) 0.9092(2) 0.0437(6) Uani 1 1 d . . .
C5 C 0.00766(16) 0.41994(14) 0.9153(2) 0.0488(6) Uani 1 1 d . . .
H5 H -0.0246 0.4464 0.9211 0.059 Uiso 1 1 calc R . .
C6 C 0.00513(18) 0.34390(16) 0.9128(2) 0.0565(7) Uani 1 1 d . . .
H6 H -0.0283 0.3188 0.9174 0.068 Uiso 1 1 calc R . .
C7 C 0.05702(14) 0.53895(14) 0.9110(2) 0.0426(6) Uani 1 1 d . . .
C8 C -0.00594(14) 0.58520(13) 0.8583(2) 0.0419(5) Uani 1 1 d . . .
C9 C 0.01932(14) 0.65983(13) 0.8812(2) 0.0423(6) Uani 1 1 d . . .
C10 C 0.10363(14) 0.65980(14) 0.9529(2) 0.0460(6) Uani 1 1 d . . .
C11 C 0.20538(17) 0.56084(19) 1.0520(3) 0.0788(11) Uani 1 1 d . . .
H11A H 0.2131 0.5225 1.0163 0.095 Uiso 1 1 calc R . .
H11B H 0.2373 0.6031 1.0665 0.095 Uiso 1 1 calc R . .
C12 C 0.2350(2) 0.5334(2) 1.1614(4) 0.0991(12) Uani 1 1 d U . .
H12A H 0.2001 0.4946 1.1480 0.119 Uiso 1 1 calc R . .
H12B H 0.2863 0.5113 1.2023 0.119 Uiso 1 1 calc R . .
C13 C 0.2417(4) 0.5890(3) 1.2323(5) 0.1194(14) Uani 1 1 d U . .
H13A H 0.1895 0.6018 1.2015 0.143 Uiso 1 1 calc R . .
H13B H 0.2645 0.6332 1.2289 0.143 Uiso 1 1 calc R . .
C14 C 0.2950(3) 0.5641(3) 1.3658(4) 0.141(2) Uani 1 1 d U . .
H14A H 0.2713 0.5220 1.3703 0.212 Uiso 1 1 calc R . .
H14B H 0.2988 0.6045 1.4097 0.212 Uiso 1 1 calc R . .
H14C H 0.3468 0.5510 1.3968 0.212 Uiso 1 1 calc R . .
C15 C -0.09060(15) 0.58482(14) 0.7767(2) 0.0460(6) Uani 1 1 d . . .
C16 C -0.04502(14) 0.70557(14) 0.8181(2) 0.0418(5) Uani 1 1 d . . .
C17 C -0.19172(15) 0.68250(16) 0.6969(2) 0.0555(7) Uani 1 1 d . . .
H17A H -0.2282 0.6468 0.6366 0.067 Uiso 1 1 calc R . .
H17B H -0.2030 0.7307 0.6607 0.067 Uiso 1 1 calc R . .
C18 C -0.20374(16) 0.68625(18) 0.7832(3) 0.0628(8) Uani 1 1 d . . .
H18A H -0.1797 0.6429 0.8331 0.075 Uiso 1 1 calc R . .
H18B H -0.1770 0.7299 0.8316 0.075 Uiso 1 1 calc R . .
C19 C -0.28871(18) 0.6895(2) 0.7254(3) 0.0764(10) Uani 1 1 d . . .
H19A H -0.3135 0.7313 0.6723 0.092 Uiso 1 1 calc R . .
H19B H -0.3149 0.6445 0.6803 0.092 Uiso 1 1 calc R . .
C20 C -0.2995(2) 0.6972(3) 0.8095(4) 0.1078(15) Uani 1 1 d . . .
H20A H -0.2802 0.6534 0.8568 0.162 Uiso 1 1 calc R . .
H20B H -0.3545 0.7034 0.7682 0.162 Uiso 1 1 calc R . .
H20C H -0.2709 0.7398 0.8578 0.162 Uiso 1 1 calc R . .
C21 C -0.04723(14) 0.78642(14) 0.8137(2) 0.0438(6) Uani 1 1 d . . .
C22 C 0.00313(17) 0.82575(16) 0.9164(2) 0.0561(7) Uani 1 1 d . . .
H22 H 0.0369 0.8002 0.9864 0.067 Uiso 1 1 calc R . .
C23 C 0.00396(19) 0.90194(17) 0.9165(3) 0.0653(8) Uani 1 1 d . . .
H23 H 0.0372 0.9280 0.9861 0.078 Uiso 1 1 calc R . .
C24 C -0.04443(18) 0.93893(15) 0.8137(3) 0.0595(8) Uani 1 1 d . . .
C25 C -0.09323(16) 0.90167(15) 0.7101(3) 0.0552(7) Uani 1 1 d . . .
H25 H -0.1248 0.9278 0.6406 0.066 Uiso 1 1 calc R . .
C26 C -0.09518(15) 0.82540(14) 0.7100(2) 0.0486(6) Uani 1 1 d . . .
H26 H -0.1288 0.7998 0.6401 0.058 Uiso 1 1 calc R . .
Cl1 Cl 0.05094(6) 0.20941(4) 0.90421(9) 0.0882(3) Uani 1 1 d . . .
Cl2 Cl -0.04454(7) 1.03506(5) 0.81302(10) 0.0947(4) Uani 1 1 d . . .
N1 N 0.12355(12) 0.58351(11) 0.96871(19) 0.0478(5) Uani 1 1 d . . .
N2 N -0.11117(12) 0.66085(12) 0.75450(18) 0.0470(5) 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
O1 C10 1.216(3) . ?
O2 C15 1.215(3) . ?
C1 C6 1.363(4) . ?
C1 C2 1.366(4) . ?
C1 Cl1 1.724(3) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 C7 1.453(3) . ?
C5 C6 1.369(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.362(3) . ?
C7 N1 1.391(3) . ?
C8 C9 1.410(3) . ?
C8 C15 1.438(3) . ?
C9 C16 1.368(3) . ?
C9 C10 1.443(3) . ?
C10 N1 1.415(3) . ?
C11 C12 1.429(5) . ?
C11 N1 1.449(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.414(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.611(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N2 1.412(3) . ?
C16 N2 1.382(3) . ?
C16 C21 1.455(3) . ?
C17 N2 1.462(3) . ?
C17 C18 1.533(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.498(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.485(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.382(4) . ?
C21 C26 1.387(4) . ?
C22 C23 1.371(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.361(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(4) . ?
C24 Cl2 1.729(3) . ?
C25 C26 1.373(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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
C6 C1 C2 121.1(3) . . ?
C6 C1 Cl1 119.5(2) . . ?
C2 C1 Cl1 119.4(2) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 C7 123.4(2) . . ?
C5 C4 C7 118.3(2) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 N1 107.2(2) . . ?
C8 C7 C4 128.3(2) . . ?
N1 C7 C4 124.6(2) . . ?
C7 C8 C9 109.9(2) . . ?
C7 C8 C15 141.6(2) . . ?
C9 C8 C15 108.0(2) . . ?
C16 C9 C8 109.2(2) . . ?
C16 C9 C10 142.5(2) . . ?
C8 C9 C10 107.7(2) . . ?
O1 C10 N1 123.1(2) . . ?
O1 C10 C9 132.8(2) . . ?
N1 C10 C9 104.0(2) . . ?
C12 C11 N1 117.4(3) . . ?
C12 C11 H11A 107.9 . . ?
N1 C11 H11A 107.9 . . ?
C12 C11 H11B 107.9 . . ?
N1 C11 H11B 107.9 . . ?
H11A C11 H11B 107.2 . . ?
C13 C12 C11 113.4(4) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 113.4(4) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 N2 123.2(2) . . ?
O2 C15 C8 132.8(2) . . ?
N2 C15 C8 104.0(2) . . ?
C9 C16 N2 107.4(2) . . ?
C9 C16 C21 128.4(2) . . ?
N2 C16 C21 124.1(2) . . ?
N2 C17 C18 111.3(2) . . ?
N2 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
N2 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 113.1(3) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 112.7(3) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 118.8(3) . . ?
C22 C21 C16 118.8(2) . . ?
C26 C21 C16 122.3(2) . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 121.4(3) . . ?
C23 C24 Cl2 119.5(2) . . ?
C25 C24 Cl2 119.0(3) . . ?
C24 C25 C26 119.4(3) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C21 120.3(3) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C7 N1 C10 111.2(2) . . ?
C7 N1 C11 127.9(2) . . ?
C10 N1 C11 120.1(2) . . ?
C16 N2 C15 111.3(2) . . ?
C16 N2 C17 127.6(2) . . ?
C15 N2 C17 119.0(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.8(4) . . . . ?
Cl1 C1 C2 C3 -178.3(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -2.5(4) . . . . ?
C2 C3 C4 C7 -179.2(3) . . . . ?
C3 C4 C5 C6 2.5(4) . . . . ?
C7 C4 C5 C6 179.4(2) . . . . ?
C2 C1 C6 C5 -1.8(4) . . . . ?
Cl1 C1 C6 C5 178.3(2) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C3 C4 C7 C8 137.5(3) . . . . ?
C5 C4 C7 C8 -39.3(4) . . . . ?
C3 C4 C7 N1 -41.8(4) . . . . ?
C5 C4 C7 N1 141.4(3) . . . . ?
N1 C7 C8 C9 0.1(3) . . . . ?
C4 C7 C8 C9 -179.3(2) . . . . ?
N1 C7 C8 C15 170.7(3) . . . . ?
C4 C7 C8 C15 -8.7(5) . . . . ?
C7 C8 C9 C16 173.7(2) . . . . ?
C15 C8 C9 C16 -0.2(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C15 C8 C9 C10 -173.8(2) . . . . ?
C16 C9 C10 O1 10.5(6) . . . . ?
C8 C9 C10 O1 -179.6(3) . . . . ?
C16 C9 C10 N1 -170.3(3) . . . . ?
C8 C9 C10 N1 -0.3(3) . . . . ?
N1 C11 C12 C13 -69.8(5) . . . . ?
C11 C12 C13 C14 -165.0(4) . . . . ?
C7 C8 C15 O2 10.9(6) . . . . ?
C9 C8 C15 O2 -178.4(3) . . . . ?
C7 C8 C15 N2 -170.1(3) . . . . ?
C9 C8 C15 N2 0.6(3) . . . . ?
C8 C9 C16 N2 -0.3(3) . . . . ?
C10 C9 C16 N2 169.6(3) . . . . ?
C8 C9 C16 C21 -179.5(2) . . . . ?
C10 C9 C16 C21 -9.7(5) . . . . ?
N2 C17 C18 C19 -165.7(3) . . . . ?
C17 C18 C19 C20 -176.9(3) . . . . ?
C9 C16 C21 C22 -45.0(4) . . . . ?
N2 C16 C21 C22 135.9(3) . . . . ?
C9 C16 C21 C26 131.7(3) . . . . ?
N2 C16 C21 C26 -47.4(4) . . . . ?
C26 C21 C22 C23 2.3(4) . . . . ?
C16 C21 C22 C23 179.1(3) . . . . ?
C21 C22 C23 C24 -1.4(5) . . . . ?
C22 C23 C24 C25 -0.7(5) . . . . ?
C22 C23 C24 Cl2 179.3(2) . . . . ?
C23 C24 C25 C26 2.0(4) . . . . ?
Cl2 C24 C25 C26 -178.1(2) . . . . ?
C24 C25 C26 C21 -1.0(4) . . . . ?
C22 C21 C26 C25 -1.0(4) . . . . ?
C16 C21 C26 C25 -177.7(2) . . . . ?
C8 C7 N1 C10 -0.3(3) . . . . ?
C4 C7 N1 C10 179.1(2) . . . . ?
C8 C7 N1 C11 169.2(3) . . . . ?
C4 C7 N1 C11 -11.4(4) . . . . ?
O1 C10 N1 C7 179.7(2) . . . . ?
C9 C10 N1 C7 0.4(3) . . . . ?
O1 C10 N1 C11 9.3(4) . . . . ?
C9 C10 N1 C11 -170.1(3) . . . . ?
C12 C11 N1 C7 -67.2(5) . . . . ?
C12 C11 N1 C10 101.5(4) . . . . ?
C9 C16 N2 C15 0.7(3) . . . . ?
C21 C16 N2 C15 -180.0(2) . . . . ?
C9 C16 N2 C17 163.7(3) . . . . ?
C21 C16 N2 C17 -17.0(4) . . . . ?
O2 C15 N2 C16 178.3(3) . . . . ?
C8 C15 N2 C16 -0.8(3) . . . . ?
O2 C15 N2 C17 13.7(4) . . . . ?
C8 C15 N2 C17 -165.5(2) . . . . ?
C18 C17 N2 C16 -80.4(3) . . . . ?
C18 C17 N2 C15 81.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.071
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol and dichloromethane (V/V=1/1)'
####################################################################### 
# 
# 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_20160714f
_database_code_depnum_ccdc_archive 'CCDC 1497297'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1,4-diketo-2,5-di(tetradecyl)-3,6-bis-(4-chlorophenyl)pyrrolo[3,4-c]pyrrole
_chemical_name_common            TDPP
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H66 Cl2 N2 O2'
_chemical_formula_sum            'C46 H66 Cl2 N2 O2'
_chemical_formula_weight         749.91

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   21.085(4)
_cell_length_b                   4.8864(8)
_cell_length_c                   21.502(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.73(2)
_cell_angle_gamma                90.00
_cell_volume                     2028.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1987
_cell_measurement_theta_min      1.78
_cell_measurement_theta_max      65.21

_exptl_crystal_description       needle
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    1.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6513
_exptl_absorpt_correction_T_max  0.8455
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10198
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         67.03
_reflns_number_total             3537
_reflns_number_gt                2657
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0741P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3537
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.08960(11) 0.8596(5) 0.13587(11) 0.0158(5) Uani 1 1 d . . .
C2 C -0.02298(11) 0.7785(5) 0.17676(11) 0.0168(5) Uani 1 1 d . . .
H2 H 0.0004 0.8593 0.2202 0.020 Uiso 1 1 calc R . .
C3 C -0.12482(11) 0.7403(5) 0.07282(10) 0.0156(5) Uani 1 1 d . . .
H3 H -0.1712 0.7920 0.0456 0.019 Uiso 1 1 calc R . .
C4 C 0.00959(11) 0.5800(5) 0.15444(10) 0.0162(5) Uani 1 1 d . . .
H4 H 0.0550 0.5224 0.1834 0.019 Uiso 1 1 calc R . .
C5 C -0.09173(11) 0.5451(5) 0.04996(10) 0.0142(5) Uani 1 1 d . . .
H5 H -0.1158 0.4655 0.0064 0.017 Uiso 1 1 calc R . .
C6 C -0.02341(11) 0.4612(5) 0.08933(10) 0.0141(5) Uani 1 1 d . . .
C7 C 0.00824(10) 0.2553(5) 0.06098(10) 0.0128(5) Uani 1 1 d . . .
C8 C -0.02425(10) 0.0895(5) 0.00467(10) 0.0119(5) Uani 1 1 d . . .
C9 C 0.09157(10) -0.0266(5) 0.04836(10) 0.0126(5) Uani 1 1 d . . .
C10 C 0.13912(10) 0.3110(5) 0.14036(10) 0.0144(5) Uani 1 1 d . . .
H10A H 0.1271 0.5001 0.1482 0.017 Uiso 1 1 calc R . .
H10B H 0.1771 0.3223 0.1245 0.017 Uiso 1 1 calc R . .
C11 C 0.16495(10) 0.1560(5) 0.20737(10) 0.0142(5) Uani 1 1 d . . .
H11A H 0.1708 -0.0398 0.1991 0.017 Uiso 1 1 calc R . .
H11B H 0.1302 0.1691 0.2274 0.017 Uiso 1 1 calc R . .
C12 C 0.23385(10) 0.2721(5) 0.25722(10) 0.0167(5) Uani 1 1 d . . .
H12A H 0.2281 0.4701 0.2633 0.020 Uiso 1 1 calc R . .
H12B H 0.2687 0.2522 0.2375 0.020 Uiso 1 1 calc R . .
C13 C 0.26105(11) 0.1330(5) 0.32667(10) 0.0160(5) Uani 1 1 d . . .
H13A H 0.2258 0.1484 0.3460 0.019 Uiso 1 1 calc R . .
H13B H 0.2683 -0.0639 0.3209 0.019 Uiso 1 1 calc R . .
C14 C 0.32865(11) 0.2569(5) 0.37625(10) 0.0176(5) Uani 1 1 d . . .
H14A H 0.3223 0.4565 0.3791 0.021 Uiso 1 1 calc R . .
H14B H 0.3648 0.2289 0.3585 0.021 Uiso 1 1 calc R . .
C15 C 0.35376(11) 0.1340(5) 0.44769(10) 0.0171(5) Uani 1 1 d . . .
H15A H 0.3181 0.1659 0.4659 0.021 Uiso 1 1 calc R . .
H15B H 0.3590 -0.0662 0.4446 0.021 Uiso 1 1 calc R . .
C16 C 0.42217(11) 0.2530(5) 0.49692(10) 0.0172(5) Uani 1 1 d . . .
H16A H 0.4174 0.4540 0.4989 0.021 Uiso 1 1 calc R . .
H16B H 0.4583 0.2158 0.4796 0.021 Uiso 1 1 calc R . .
C17 C 0.44558(11) 0.1355(5) 0.56859(10) 0.0173(5) Uani 1 1 d . . .
H17A H 0.4089 0.1690 0.5853 0.021 Uiso 1 1 calc R . .
H17B H 0.4511 -0.0651 0.5665 0.021 Uiso 1 1 calc R . .
C18 C 0.51332(11) 0.2559(5) 0.61920(10) 0.0168(5) Uani 1 1 d . . .
H18A H 0.5082 0.4567 0.6211 0.020 Uiso 1 1 calc R . .
H18B H 0.5504 0.2199 0.6031 0.020 Uiso 1 1 calc R . .
C19 C 0.53494(11) 0.1380(5) 0.69044(10) 0.0172(5) Uani 1 1 d . . .
H19A H 0.4972 0.1702 0.7059 0.021 Uiso 1 1 calc R . .
H19B H 0.5408 -0.0624 0.6884 0.021 Uiso 1 1 calc R . .
C20 C 0.60172(11) 0.2586(5) 0.74251(10) 0.0183(5) Uani 1 1 d . . .
H20A H 0.5964 0.4595 0.7442 0.022 Uiso 1 1 calc R . .
H20B H 0.6398 0.2227 0.7278 0.022 Uiso 1 1 calc R . .
C21 C 0.62138(11) 0.1411(5) 0.81372(10) 0.0182(5) Uani 1 1 d . . .
H21A H 0.5822 0.1688 0.8273 0.022 Uiso 1 1 calc R . .
H21B H 0.6288 -0.0584 0.8123 0.022 Uiso 1 1 calc R . .
C22 C 0.68620(11) 0.2689(5) 0.86731(11) 0.0205(5) Uani 1 1 d . . .
H22A H 0.6791 0.4686 0.8689 0.025 Uiso 1 1 calc R . .
H22B H 0.7257 0.2402 0.8542 0.025 Uiso 1 1 calc R . .
C23 C 0.70410(11) 0.1478(6) 0.93788(11) 0.0239(6) Uani 1 1 d . . .
H23A H 0.6647 0.1711 0.9506 0.036 Uiso 1 1 calc R . .
H23B H 0.7447 0.2421 0.9710 0.036 Uiso 1 1 calc R . .
H23C H 0.7144 -0.0476 0.9374 0.036 Uiso 1 1 calc R . .
Cl1 Cl -0.13030(3) 1.11357(12) 0.16399(3) 0.01834(18) Uani 1 1 d . . .
N1 N 0.07843(8) 0.1849(4) 0.08675(8) 0.0122(4) Uani 1 1 d . . .
O1 O 0.14981(7) -0.1194(3) 0.06329(7) 0.0168(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 C2 1.382(3) . ?
C1 C3 1.385(3) . ?
C1 Cl1 1.749(2) . ?
C2 C4 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C5 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C6 1.413(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.468(3) . ?
C7 C8 1.387(3) . ?
C7 N1 1.398(3) . ?
C8 C8 1.420(4) 3 ?
C8 C9 1.451(3) 3 ?
C9 O1 1.224(3) . ?
C9 N1 1.418(3) . ?
C9 C8 1.451(3) 3 ?
C10 N1 1.469(3) . ?
C10 C11 1.522(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.527(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.520(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.532(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.528(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.523(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.525(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.522(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.528(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.522(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.528(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 C1 C3 120.6(2) . . ?
C2 C1 Cl1 119.87(17) . . ?
C3 C1 Cl1 119.50(17) . . ?
C4 C2 C1 120.0(2) . . ?
C4 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C5 C3 C1 119.3(2) . . ?
C5 C3 H3 120.4 . . ?
C1 C3 H3 120.4 . . ?
C2 C4 C6 121.1(2) . . ?
C2 C4 H4 119.4 . . ?
C6 C4 H4 119.4 . . ?
C3 C5 C6 121.87(19) . . ?
C3 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C4 116.9(2) . . ?
C5 C6 C7 118.46(19) . . ?
C4 C6 C7 124.59(19) . . ?
C8 C7 N1 105.94(18) . . ?
C8 C7 C6 127.96(18) . . ?
N1 C7 C6 126.10(18) . . ?
C7 C8 C8 110.6(2) . 3 ?
C7 C8 C9 142.4(2) . 3 ?
C8 C8 C9 106.9(2) 3 3 ?
O1 C9 N1 121.84(18) . . ?
O1 C9 C8 133.5(2) . 3 ?
N1 C9 C8 104.67(17) . 3 ?
N1 C10 C11 113.64(18) . . ?
N1 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 110.89(18) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 113.45(18) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 112.68(18) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 113.29(19) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 113.38(19) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 112.93(19) . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 113.89(19) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 112.78(19) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 114.01(19) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 112.91(19) . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 113.8(2) . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 C23 112.4(2) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 N1 C9 111.84(16) . . ?
C7 N1 C10 131.04(18) . . ?
C9 N1 C10 116.73(16) . . ?

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 C1 C2 C4 1.1(3) . . . . ?
Cl1 C1 C2 C4 -179.34(17) . . . . ?
C2 C1 C3 C5 -2.3(3) . . . . ?
Cl1 C1 C3 C5 178.17(17) . . . . ?
C1 C2 C4 C6 1.5(3) . . . . ?
C1 C3 C5 C6 0.8(3) . . . . ?
C3 C5 C6 C4 1.7(3) . . . . ?
C3 C5 C6 C7 -179.3(2) . . . . ?
C2 C4 C6 C5 -2.9(3) . . . . ?
C2 C4 C6 C7 178.1(2) . . . . ?
C5 C6 C7 C8 -13.3(3) . . . . ?
C4 C6 C7 C8 165.6(2) . . . . ?
C5 C6 C7 N1 167.5(2) . . . . ?
C4 C6 C7 N1 -13.5(3) . . . . ?
N1 C7 C8 C8 1.3(3) . . . 3 ?
C6 C7 C8 C8 -177.9(2) . . . 3 ?
N1 C7 C8 C9 179.2(3) . . . 3 ?
C6 C7 C8 C9 -0.1(4) . . . 3 ?
N1 C10 C11 C12 171.54(17) . . . . ?
C10 C11 C12 C13 177.50(18) . . . . ?
C11 C12 C13 C14 -178.36(19) . . . . ?
C12 C13 C14 C15 175.67(19) . . . . ?
C13 C14 C15 C16 178.69(19) . . . . ?
C14 C15 C16 C17 178.19(19) . . . . ?
C15 C16 C17 C18 -178.83(19) . . . . ?
C16 C17 C18 C19 179.23(19) . . . . ?
C17 C18 C19 C20 -178.81(19) . . . . ?
C18 C19 C20 C21 178.82(19) . . . . ?
C19 C20 C21 C22 -177.24(19) . . . . ?
C20 C21 C22 C23 179.7(2) . . . . ?
C8 C7 N1 C9 -0.8(2) . . . . ?
C6 C7 N1 C9 178.49(19) . . . . ?
C8 C7 N1 C10 171.8(2) . . . . ?
C6 C7 N1 C10 -9.0(3) . . . . ?
O1 C9 N1 C7 -179.12(19) . . . . ?
C8 C9 N1 C7 0.0(2) 3 . . . ?
O1 C9 N1 C10 7.2(3) . . . . ?
C8 C9 N1 C10 -173.74(17) 3 . . . ?
C11 C10 N1 C7 102.8(2) . . . . ?
C11 C10 N1 C9 -85.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        67.03
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.083
