# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_hag4
_database_code_depnum_ccdc_archive 'CCDC 2101458'
loop_
_audit_author_name
_audit_author_address
'Tadeusz Lis'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
2-(2,6-diisopropylphenyl)-1H-benzo[7,8]pyrido[3'',4'',5'':5',6']acenaphtho[1',2':1,2]indolizino[6,5,4,3-def]phenanthridine-1,3(2H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H32 N2 O2, 0.6(C D Cl3), 0.4(C H4 O)'
_chemical_formula_sum            'C47 H33.60 D0.60 Cl1.80 N2 O2.40'
_chemical_formula_weight         729.78

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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.004(3)
_cell_length_b                   15.289(5)
_cell_length_c                   16.218(6)
_cell_angle_alpha                69.01(5)
_cell_angle_beta                 83.97(4)
_cell_angle_gamma                86.68(4)
_cell_volume                     1842.3(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2372
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      50

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.797
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_T_min  0.61200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            21540
_diffrn_reflns_av_unetI/netI     0.1742
_diffrn_reflns_av_R_equivalents  0.1141
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.930
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             6492
_reflns_number_gt                1792
_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       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6492
_refine_ls_number_parameters     501
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.3542
_refine_ls_R_factor_gt           0.1716
_refine_ls_wR_factor_ref         0.4984
_refine_ls_wR_factor_gt          0.3934
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.002
_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 0.6987(11) 0.4474(6) 0.5377(8) 0.082(3) Uani 1 1 d . . . . .
C1 C 0.7392(13) 0.5414(8) 0.5065(10) 0.074(4) Uani 1 1 d . . . . .
C2 C 0.6501(12) 0.5804(8) 0.5647(10) 0.083(4) Uani 1 1 d . . . . .
C3 C 0.5586(12) 0.5067(7) 0.6364(10) 0.084(4) Uani 1 1 d . . . . .
C4 C 0.5921(13) 0.4229(7) 0.6198(10) 0.075(4) Uani 1 1 d . . . . .
C5 C 0.6147(13) 0.6664(7) 0.5837(10) 0.084(4) Uani 1 1 d . . . . .
C6 C 0.6540(12) 0.7623(8) 0.5440(10) 0.095(5) Uani 1 1 d . . . . .
H6 H 0.7249 0.7828 0.4901 0.114 Uiso 1 1 calc R U . . .
C7 C 0.5904(13) 0.8284(8) 0.5824(11) 0.091(5) Uani 1 1 d . . . . .
H7 H 0.6206 0.8922 0.5546 0.109 Uiso 1 1 calc R U . . .
C8 C 0.4826(13) 0.8011(7) 0.6615(11) 0.088(4) Uani 1 1 d . . . . .
C9 C 0.3212(15) 0.6708(8) 0.7805(10) 0.084(4) Uani 1 1 d . . . . .
C10 C 0.2828(13) 0.5800(8) 0.8128(9) 0.080(4) Uani 1 1 d . . . . .
H10 H 0.2051 0.5575 0.8638 0.096 Uiso 1 1 calc R U . . .
C11 C 0.3576(14) 0.5143(8) 0.7713(10) 0.095(5) Uani 1 1 d . . . . .
H11 H 0.3294 0.4500 0.7964 0.114 Uiso 1 1 calc R U . . .
C12 C 0.4659(13) 0.5442(7) 0.6979(9) 0.070(3) Uani 1 1 d . . . . .
C13 C 0.5057(14) 0.6428(7) 0.6634(10) 0.078(4) Uani 1 1 d . . . . .
C14 C 0.4379(13) 0.7060(7) 0.6998(10) 0.077(4) Uani 1 1 d . . . . .
C15 C 0.4113(14) 0.8681(8) 0.7025(10) 0.080(4) Uani 1 1 d . . . . .
C16 C 0.2476(16) 0.7402(8) 0.8157(10) 0.086(4) Uani 1 1 d . . . . .
O1 O 0.4514(8) 0.9522(5) 0.6716(6) 0.085(3) Uani 1 1 d . . . . .
O2 O 0.1425(11) 0.7194(5) 0.8826(7) 0.115(4) Uani 1 1 d . . . . .
N2 N 0.3025(10) 0.8340(5) 0.7787(7) 0.066(3) Uani 1 1 d . . . . .
C17 C 0.2272(15) 0.9005(8) 0.8156(12) 0.096(5) Uani 1 1 d . . . . .
C18 C 0.0915(13) 0.9557(8) 0.7765(11) 0.089(4) Uani 1 1 d . . . . .
C19 C 0.0206(15) 1.0192(8) 0.8153(11) 0.096(5) Uani 1 1 d . . . . .
H19 H -0.0687 1.0594 0.7884 0.115 Uiso 1 1 calc R U . . .
C20 C 0.0729(17) 1.0259(9) 0.8888(13) 0.109(6) Uani 1 1 d . . . . .
H20 H 0.0170 1.0684 0.9136 0.131 Uiso 1 1 calc R U . . .
C21 C 0.2038(16) 0.9730(9) 0.9281(11) 0.103(5) Uani 1 1 d . . . . .
H21 H 0.2429 0.9811 0.9782 0.124 Uiso 1 1 calc R U . . .
C22 C 0.2846(18) 0.9042(9) 0.8939(12) 0.100(5) Uani 1 1 d . . . . .
C23 C 0.0303(14) 0.9559(9) 0.6899(10) 0.085(4) Uani 1 1 d . . . . .
H23 H 0.0894 0.9026 0.6762 0.102 Uiso 1 1 calc R U . . .
C24 C 0.0803(16) 1.0459(11) 0.6128(13) 0.150(8) Uani 1 1 d . . . . .
H24A H 0.0228 1.0998 0.6234 0.225 Uiso 1 1 calc R U . . .
H24E H 0.0480 1.0423 0.5575 0.225 Uiso 1 1 calc R U . . .
H24F H 0.2021 1.0532 0.6082 0.225 Uiso 1 1 calc R U . . .
C25 C -0.1563(13) 0.9389(10) 0.6994(12) 0.142(7) Uani 1 1 d . . . . .
H25A H -0.1805 0.8772 0.7446 0.212 Uiso 1 1 calc R U . . .
H25B H -0.1911 0.9411 0.6425 0.212 Uiso 1 1 calc R U . . .
H25C H -0.2181 0.9874 0.7173 0.212 Uiso 1 1 calc R U . . .
C26 C 0.4299(18) 0.8460(10) 0.9376(12) 0.107(5) Uani 1 1 d . . . . .
H26 H 0.4659 0.8040 0.9035 0.128 Uiso 1 1 calc R U . . .
C27 C 0.362(3) 0.7796(13) 1.0343(16) 0.196(9) Uani 1 1 d . . . . .
H27A H 0.3136 0.8180 1.0684 0.294 Uiso 1 1 calc R U . . .
H27B H 0.4544 0.7406 1.0643 0.294 Uiso 1 1 calc R U . . .
H27C H 0.2748 0.7394 1.0297 0.294 Uiso 1 1 calc R U . . .
C28 C 0.5859(17) 0.9015(11) 0.9357(13) 0.150(7) Uani 1 1 d . . . . .
H28A H 0.6008 0.9535 0.8787 0.225 Uiso 1 1 calc R U . . .
H28B H 0.6856 0.8600 0.9431 0.225 Uiso 1 1 calc R U . . .
H28C H 0.5706 0.9264 0.9840 0.225 Uiso 1 1 calc R U . . .
C1A C 0.8452(13) 0.5775(7) 0.4264(10) 0.080(4) Uani 1 1 d . . . . .
C2A C 0.8906(14) 0.6716(8) 0.3909(10) 0.087(4) Uani 1 1 d . . . . .
H2A H 0.8490 0.7124 0.4212 0.104 Uiso 1 1 calc R U . . .
C3A C 0.9943(15) 0.7073(8) 0.3130(11) 0.100(5) Uani 1 1 d . . . . .
H3A H 1.0200 0.7720 0.2885 0.120 Uiso 1 1 calc R U . . .
C4A C 1.0597(12) 0.6451(9) 0.2720(10) 0.092(4) Uani 1 1 d . . . . .
H4A H 1.1347 0.6675 0.2199 0.110 Uiso 1 1 calc R U . . .
C5A C 1.0183(14) 0.5523(8) 0.3053(11) 0.090(4) Uani 1 1 d . . . . .
H5A H 1.0605 0.5118 0.2748 0.108 Uiso 1 1 calc R U . . .
C6A C 0.9125(13) 0.5171(8) 0.3850(9) 0.074(4) Uani 1 1 d . . . . .
C7A C 0.8684(13) 0.4167(7) 0.4200(11) 0.088(4) Uani 1 1 d . . . . .
C8A C 0.9389(13) 0.3530(7) 0.3843(10) 0.091(4) Uani 1 1 d . . . . .
H8A H 1.0181 0.3723 0.3337 0.109 Uiso 1 1 calc R U . . .
C1B C 0.5439(14) 0.3253(7) 0.6607(10) 0.078(4) Uani 1 1 d . . . . .
C2B C 0.4395(14) 0.2999(8) 0.7357(10) 0.092(4) Uani 1 1 d . . . . .
H2B H 0.4010 0.3450 0.7617 0.110 Uiso 1 1 calc R U . . .
C3B C 0.3874(14) 0.2063(9) 0.7755(12) 0.124(6) Uani 1 1 d . . . . .
H3B H 0.3161 0.1884 0.8292 0.149 Uiso 1 1 calc R U . . .
C4B C 0.4382(16) 0.1405(8) 0.7380(10) 0.088(4) Uani 1 1 d . . . . .
H4B H 0.4043 0.0773 0.7657 0.105 Uiso 1 1 calc R U . . .
C5B C 0.5395(13) 0.1682(7) 0.6591(9) 0.067(3) Uani 1 1 d . . . . .
H5B H 0.5706 0.1239 0.6311 0.080 Uiso 1 1 calc R U . . .
C6B C 0.5984(13) 0.2616(7) 0.6185(11) 0.084(4) Uani 1 1 d . . . . .
C7B C 0.7111(14) 0.2887(7) 0.5400(9) 0.071(3) Uani 1 1 d . . . . .
C8B C 0.7843(14) 0.2271(8) 0.4987(11) 0.098(5) Uani 1 1 d . . . . .
H8B H 0.7577 0.1626 0.5235 0.118 Uiso 1 1 calc R U . . .
C1C C 0.7614(13) 0.3839(7) 0.4997(10) 0.085(4) Uani 1 1 d . . . . .
C2C C 0.8924(15) 0.2579(9) 0.4237(10) 0.090(4) Uani 1 1 d . . . . .
H2C H 0.9378 0.2144 0.3973 0.108 Uiso 1 1 calc R U . . .
C1D C 0.825(2) 0.6012(12) 0.9130(13) 0.067(5) Uiso 0.6 1 d . . P A 1
D1 D 0.9328 0.6230 0.9246 0.080 Uiso 0.6 1 calc R U P A 1
Cl1 Cl 0.8415(7) 0.4789(4) 0.9321(5) 0.129(3) Uani 0.6 1 d . . P A 1
Cl2 Cl 0.7777(7) 0.6649(5) 0.8102(5) 0.131(3) Uani 0.6 1 d . . P A 1
Cl3 Cl 0.6574(14) 0.6171(6) 0.9888(7) 0.216(5) Uani 0.6 1 d . . P A 1
C1M C 1.035(8) 0.345(3) 0.899(4) 0.107(16) Uiso 0.2 1 d D . P B 2
H1M1 H 0.9139 0.3393 0.8979 0.161 Uiso 0.2 1 d R U P B 2
H1M2 H 1.0859 0.3757 0.8384 0.161 Uiso 0.2 1 d R U P B 2
H1M3 H 1.0532 0.3829 0.9349 0.161 Uiso 0.2 1 d R U P B 2
O1M O 1.076(6) 0.251(3) 0.950(3) 0.124(16) Uiso 0.2 1 d D . P B 2
H1M H 1.1803 0.2576 0.9424 0.186 Uiso 0.2 1 d R U P B 2
C2M C 1.108(7) 0.315(4) 0.969(5) 0.107(16) Uiso 0.2 1 d D . P C 3
H2M1 H 1.1745 0.3559 0.9167 0.161 Uiso 0.2 1 d R U P C 3
H2M2 H 1.0646 0.2634 0.9565 0.161 Uiso 0.2 1 d R U P C 3
H2M3 H 1.1801 0.2898 1.0185 0.161 Uiso 0.2 1 d R U P C 3
O2M O 0.985(7) 0.388(4) 0.952(4) 0.17(2) Uiso 0.2 1 d D . P C 3
H2M H 0.9587 0.4025 0.9968 0.249 Uiso 0.2 1 d R U P C 3


_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 C1C 1.372(13) . ?
N1 C1 1.389(13) . ?
N1 C4 1.442(14) . ?
C1 C2 1.401(15) . ?
C1 C1A 1.422(17) . ?
C2 C5 1.461(14) . ?
C2 C3 1.462(16) . ?
C3 C4 1.407(14) . ?
C3 C12 1.443(15) . ?
C4 C1B 1.456(14) . ?
C5 C6 1.415(14) . ?
C5 C13 1.423(16) . ?
C6 C7 1.411(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.411(17) . ?
C7 H7 0.9500 . ?
C8 C14 1.412(14) . ?
C8 C15 1.468(15) . ?
C9 C10 1.339(14) . ?
C9 C16 1.446(16) . ?
C9 C14 1.473(17) . ?
C10 C11 1.467(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.347(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.449(14) . ?
C13 C14 1.364(14) . ?
C15 O1 1.249(12) . ?
C15 N2 1.387(14) . ?
C16 O2 1.256(13) . ?
C16 N2 1.417(14) . ?
N2 C17 1.429(14) . ?
C17 C18 1.396(17) . ?
C17 C22 1.415(19) . ?
C18 C19 1.400(16) . ?
C18 C23 1.533(17) . ?
C19 C20 1.343(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.353(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.448(17) . ?
C21 H21 0.9500 . ?
C22 C26 1.500(18) . ?
C23 C25 1.513(15) . ?
C23 C24 1.530(18) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24E 0.9800 . ?
C24 H24F 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C28 1.542(18) . ?
C26 C27 1.59(2) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C1A C6A 1.380(14) . ?
C1A C2A 1.400(14) . ?
C2A C3A 1.386(17) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.394(15) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.373(15) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.415(16) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.482(15) . ?
C7A C8A 1.370(15) . ?
C7A C1C 1.417(18) . ?
C8A C2C 1.416(15) . ?
C8A H8A 0.9500 . ?
C1B C2B 1.346(16) . ?
C1B C6B 1.405(15) . ?
C2B C3B 1.411(16) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.374(17) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.381(15) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.426(14) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.424(16) . ?
C7B C8B 1.410(15) . ?
C7B C1C 1.427(14) . ?
C8B C2C 1.365(17) . ?
C8B H8B 0.9500 . ?
C2C H2C 0.9500 . ?
C1D Cl2 1.67(2) . ?
C1D Cl1 1.781(17) . ?
C1D Cl3 1.792(18) . ?
C1D D1 1.0000 . ?
C1M O1M 1.419(5) . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9801 . ?
C1M H1M3 0.9800 . ?
O1M H1M 0.8400 . ?
C2M O2M 1.421(5) . ?
C2M H2M1 0.9801 . ?
C2M H2M2 0.9800 . ?
C2M H2M3 0.9800 . ?
O2M H2M 0.8400 . ?

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
C1C N1 C1 124.8(12) . . ?
C1C N1 C4 123.9(10) . . ?
C1 N1 C4 111.1(10) . . ?
N1 C1 C2 106.4(11) . . ?
N1 C1 C1A 118.7(11) . . ?
C2 C1 C1A 134.9(10) . . ?
C1 C2 C5 144.7(12) . . ?
C1 C2 C3 109.3(10) . . ?
C5 C2 C3 105.9(11) . . ?
C4 C3 C12 142.2(12) . . ?
C4 C3 C2 106.9(11) . . ?
C12 C3 C2 110.8(9) . . ?
C3 C4 N1 106.1(10) . . ?
C3 C4 C1B 137.2(13) . . ?
N1 C4 C1B 116.6(10) . . ?
C6 C5 C13 115.1(10) . . ?
C6 C5 C2 137.7(13) . . ?
C13 C5 C2 107.2(10) . . ?
C7 C6 C5 121.5(13) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C6 121.0(11) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C14 117.8(12) . . ?
C7 C8 C15 122.5(11) . . ?
C14 C8 C15 119.6(14) . . ?
C10 C9 C16 124.7(14) . . ?
C10 C9 C14 119.1(11) . . ?
C16 C9 C14 116.1(11) . . ?
C9 C10 C11 121.6(12) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.6(11) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C3 138.5(10) . . ?
C11 C12 C13 117.2(11) . . ?
C3 C12 C13 104.3(11) . . ?
C14 C13 C5 124.3(11) . . ?
C14 C13 C12 123.8(13) . . ?
C5 C13 C12 111.8(11) . . ?
C13 C14 C8 120.2(13) . . ?
C13 C14 C9 117.6(10) . . ?
C8 C14 C9 122.2(11) . . ?
O1 C15 N2 121.0(10) . . ?
O1 C15 C8 121.3(13) . . ?
N2 C15 C8 117.6(11) . . ?
O2 C16 N2 117.6(11) . . ?
O2 C16 C9 122.1(12) . . ?
N2 C16 C9 120.1(12) . . ?
C15 N2 C16 124.0(10) . . ?
C15 N2 C17 117.2(9) . . ?
C16 N2 C17 118.4(10) . . ?
C18 C17 C22 121.8(13) . . ?
C18 C17 N2 118.8(14) . . ?
C22 C17 N2 119.2(13) . . ?
C17 C18 C19 116.8(14) . . ?
C17 C18 C23 123.1(12) . . ?
C19 C18 C23 119.8(12) . . ?
C20 C19 C18 123.1(14) . . ?
C20 C19 H19 118.4 . . ?
C18 C19 H19 118.4 . . ?
C19 C20 C21 121.1(14) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 120.1(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 116.8(14) . . ?
C17 C22 C26 123.2(13) . . ?
C21 C22 C26 119.8(14) . . ?
C25 C23 C24 112.3(11) . . ?
C25 C23 C18 111.9(12) . . ?
C24 C23 C18 110.9(11) . . ?
C25 C23 H23 107.2 . . ?
C24 C23 H23 107.2 . . ?
C18 C23 H23 107.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24E 109.5 . . ?
H24A C24 H24E 109.5 . . ?
C23 C24 H24F 109.5 . . ?
H24A C24 H24F 109.5 . . ?
H24E C24 H24F 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 . . ?
C22 C26 C28 115.1(12) . . ?
C22 C26 C27 107.9(14) . . ?
C28 C26 C27 114.0(14) . . ?
C22 C26 H26 106.4 . . ?
C28 C26 H26 106.4 . . ?
C27 C26 H26 106.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C6A C1A C2A 118.9(13) . . ?
C6A C1A C1 119.2(11) . . ?
C2A C1A C1 121.8(11) . . ?
C3A C2A C1A 122.2(12) . . ?
C3A C2A H2A 118.9 . . ?
C1A C2A H2A 118.9 . . ?
C2A C3A C4A 117.7(12) . . ?
C2A C3A H3A 121.1 . . ?
C4A C3A H3A 121.1 . . ?
C5A C4A C3A 121.6(13) . . ?
C5A C4A H4A 119.2 . . ?
C3A C4A H4A 119.2 . . ?
C4A C5A C6A 119.9(12) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A H5A 120.1 . . ?
C1A C6A C5A 119.6(11) . . ?
C1A C6A C7A 121.0(12) . . ?
C5A C6A C7A 119.3(11) . . ?
C8A C7A C1C 118.6(11) . . ?
C8A C7A C6A 123.2(13) . . ?
C1C C7A C6A 117.9(11) . . ?
C7A C8A C2C 119.3(13) . . ?
C7A C8A H8A 120.4 . . ?
C2C C8A H8A 120.4 . . ?
C2B C1B C6B 121.8(11) . . ?
C2B C1B C4 118.7(11) . . ?
C6B C1B C4 119.5(13) . . ?
C1B C2B C3B 119.8(12) . . ?
C1B C2B H2B 120.1 . . ?
C3B C2B H2B 120.1 . . ?
C4B C3B C2B 121.1(15) . . ?
C4B C3B H3B 119.5 . . ?
C2B C3B H3B 119.5 . . ?
C3B C4B C5B 118.6(12) . . ?
C3B C4B H4B 120.7 . . ?
C5B C4B H4B 120.7 . . ?
C4B C5B C6B 121.7(11) . . ?
C4B C5B H5B 119.2 . . ?
C6B C5B H5B 119.2 . . ?
C1B C6B C7B 121.3(11) . . ?
C1B C6B C5B 117.0(13) . . ?
C7B C6B C5B 121.7(10) . . ?
C8B C7B C6B 124.7(11) . . ?
C8B C7B C1C 115.5(12) . . ?
C6B C7B C1C 119.8(11) . . ?
C2C C8B C7B 121.6(11) . . ?
C2C C8B H8B 119.2 . . ?
C7B C8B H8B 119.2 . . ?
N1 C1C C7A 118.3(10) . . ?
N1 C1C C7B 118.7(12) . . ?
C7A C1C C7B 123.0(11) . . ?
C8B C2C C8A 121.9(12) . . ?
C8B C2C H2C 119.1 . . ?
C8A C2C H2C 119.1 . . ?
Cl2 C1D Cl1 112.7(11) . . ?
Cl2 C1D Cl3 107.7(10) . . ?
Cl1 C1D Cl3 106.9(9) . . ?
Cl2 C1D D1 109.8 . . ?
Cl1 C1D D1 109.8 . . ?
Cl3 C1D D1 109.8 . . ?
O1M C1M H1M1 99.3 . . ?
O1M C1M H1M2 121.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 106.9 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
C1M O1M H1M 95.8 . . ?
O2M C2M H2M1 86.5 . . ?
O2M C2M H2M2 107.7 . . ?
H2M1 C2M H2M2 109.5 . . ?
O2M C2M H2M3 131.0 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?
C2M O2M H2M 110.2 . . ?

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
C1C N1 C1 C2 -179.4(10) . . . . ?
C4 N1 C1 C2 -4.0(13) . . . . ?
C1C N1 C1 C1A 4.0(17) . . . . ?
C4 N1 C1 C1A 179.4(10) . . . . ?
N1 C1 C2 C5 -179.3(16) . . . . ?
C1A C1 C2 C5 -3(3) . . . . ?
N1 C1 C2 C3 2.9(13) . . . . ?
C1A C1 C2 C3 178.8(12) . . . . ?
C1 C2 C3 C4 -0.9(13) . . . . ?
C5 C2 C3 C4 -179.5(9) . . . . ?
C1 C2 C3 C12 179.7(9) . . . . ?
C5 C2 C3 C12 1.1(13) . . . . ?
C12 C3 C4 N1 177.6(14) . . . . ?
C2 C3 C4 N1 -1.5(12) . . . . ?
C12 C3 C4 C1B 0(3) . . . . ?
C2 C3 C4 C1B -178.9(13) . . . . ?
C1C N1 C4 C3 178.9(10) . . . . ?
C1 N1 C4 C3 3.4(13) . . . . ?
C1C N1 C4 C1B -3.1(16) . . . . ?
C1 N1 C4 C1B -178.5(9) . . . . ?
C1 C2 C5 C6 5(3) . . . . ?
C3 C2 C5 C6 -177.7(14) . . . . ?
C1 C2 C5 C13 -178.2(16) . . . . ?
C3 C2 C5 C13 -0.4(13) . . . . ?
C13 C5 C6 C7 0.9(17) . . . . ?
C2 C5 C6 C7 178.1(13) . . . . ?
C5 C6 C7 C8 -1.1(18) . . . . ?
C6 C7 C8 C14 -1.2(17) . . . . ?
C6 C7 C8 C15 -178.8(11) . . . . ?
C16 C9 C10 C11 177.4(12) . . . . ?
C14 C9 C10 C11 1.7(19) . . . . ?
C9 C10 C11 C12 -1.1(19) . . . . ?
C10 C11 C12 C3 -176.7(13) . . . . ?
C10 C11 C12 C13 0.8(18) . . . . ?
C4 C3 C12 C11 -3(3) . . . . ?
C2 C3 C12 C11 176.4(14) . . . . ?
C4 C3 C12 C13 179.6(15) . . . . ?
C2 C3 C12 C13 -1.3(12) . . . . ?
C6 C5 C13 C14 1.6(18) . . . . ?
C2 C5 C13 C14 -176.4(11) . . . . ?
C6 C5 C13 C12 177.6(10) . . . . ?
C2 C5 C13 C12 -0.4(13) . . . . ?
C11 C12 C13 C14 -1.2(18) . . . . ?
C3 C12 C13 C14 177.1(11) . . . . ?
C11 C12 C13 C5 -177.2(11) . . . . ?
C3 C12 C13 C5 1.1(13) . . . . ?
C5 C13 C14 C8 -4.0(18) . . . . ?
C12 C13 C14 C8 -179.5(11) . . . . ?
C5 C13 C14 C9 177.3(11) . . . . ?
C12 C13 C14 C9 1.8(17) . . . . ?
C7 C8 C14 C13 3.6(17) . . . . ?
C15 C8 C14 C13 -178.7(11) . . . . ?
C7 C8 C14 C9 -177.7(11) . . . . ?
C15 C8 C14 C9 -0.1(18) . . . . ?
C10 C9 C14 C13 -2.0(17) . . . . ?
C16 C9 C14 C13 -178.1(11) . . . . ?
C10 C9 C14 C8 179.3(11) . . . . ?
C16 C9 C14 C8 3.2(18) . . . . ?
C7 C8 C15 O1 -4.3(18) . . . . ?
C14 C8 C15 O1 178.2(11) . . . . ?
C7 C8 C15 N2 178.0(10) . . . . ?
C14 C8 C15 N2 0.5(17) . . . . ?
C10 C9 C16 O2 2(2) . . . . ?
C14 C9 C16 O2 177.9(12) . . . . ?
C10 C9 C16 N2 177.4(12) . . . . ?
C14 C9 C16 N2 -6.8(18) . . . . ?
O1 C15 N2 C16 177.9(11) . . . . ?
C8 C15 N2 C16 -4.4(17) . . . . ?
O1 C15 N2 C17 5.4(17) . . . . ?
C8 C15 N2 C17 -176.9(11) . . . . ?
O2 C16 N2 C15 -176.6(11) . . . . ?
C9 C16 N2 C15 7.8(18) . . . . ?
O2 C16 N2 C17 -4.2(18) . . . . ?
C9 C16 N2 C17 -179.8(12) . . . . ?
C15 N2 C17 C18 78.3(13) . . . . ?
C16 N2 C17 C18 -94.6(14) . . . . ?
C15 N2 C17 C22 -105.9(14) . . . . ?
C16 N2 C17 C22 81.2(14) . . . . ?
C22 C17 C18 C19 3.6(18) . . . . ?
N2 C17 C18 C19 179.4(10) . . . . ?
C22 C17 C18 C23 177.7(12) . . . . ?
N2 C17 C18 C23 -6.5(17) . . . . ?
C17 C18 C19 C20 -2.7(19) . . . . ?
C23 C18 C19 C20 -177.0(12) . . . . ?
C18 C19 C20 C21 3(2) . . . . ?
C19 C20 C21 C22 -3(2) . . . . ?
C18 C17 C22 C21 -4.4(18) . . . . ?
N2 C17 C22 C21 179.9(10) . . . . ?
C18 C17 C22 C26 -179.9(12) . . . . ?
N2 C17 C22 C26 4.3(19) . . . . ?
C20 C21 C22 C17 4.1(18) . . . . ?
C20 C21 C22 C26 179.9(13) . . . . ?
C17 C18 C23 C25 127.8(12) . . . . ?
C19 C18 C23 C25 -58.3(15) . . . . ?
C17 C18 C23 C24 -106.1(13) . . . . ?
C19 C18 C23 C24 67.9(14) . . . . ?
C17 C22 C26 C28 113.2(15) . . . . ?
C21 C22 C26 C28 -62.2(19) . . . . ?
C17 C22 C26 C27 -118.2(15) . . . . ?
C21 C22 C26 C27 66.3(15) . . . . ?
N1 C1 C1A C6A -3.8(16) . . . . ?
C2 C1 C1A C6A -179.2(12) . . . . ?
N1 C1 C1A C2A 179.8(11) . . . . ?
C2 C1 C1A C2A 4(2) . . . . ?
C6A C1A C2A C3A 3.3(19) . . . . ?
C1 C1A C2A C3A 179.7(12) . . . . ?
C1A C2A C3A C4A -2.8(19) . . . . ?
C2A C3A C4A C5A 2.5(19) . . . . ?
C3A C4A C5A C6A -2.7(19) . . . . ?
C2A C1A C6A C5A -3.4(17) . . . . ?
C1 C1A C6A C5A -179.9(11) . . . . ?
C2A C1A C6A C7A 179.9(11) . . . . ?
C1 C1A C6A C7A 3.4(17) . . . . ?
C4A C5A C6A C1A 3.1(18) . . . . ?
C4A C5A C6A C7A 179.9(11) . . . . ?
C1A C6A C7A C8A -176.2(11) . . . . ?
C5A C6A C7A C8A 7.1(19) . . . . ?
C1A C6A C7A C1C -2.9(17) . . . . ?
C5A C6A C7A C1C -179.6(10) . . . . ?
C1C C7A C8A C2C 5.1(18) . . . . ?
C6A C7A C8A C2C 178.3(11) . . . . ?
C3 C4 C1B C2B 0(2) . . . . ?
N1 C4 C1B C2B -177.6(10) . . . . ?
C3 C4 C1B C6B 175.7(13) . . . . ?
N1 C4 C1B C6B -1.5(16) . . . . ?
C6B C1B C2B C3B 2.5(19) . . . . ?
C4 C1B C2B C3B 178.5(11) . . . . ?
C1B C2B C3B C4B -2(2) . . . . ?
C2B C3B C4B C5B -1.1(19) . . . . ?
C3B C4B C5B C6B 3.1(18) . . . . ?
C2B C1B C6B C7B -178.9(11) . . . . ?
C4 C1B C6B C7B 5.1(17) . . . . ?
C2B C1B C6B C5B -0.6(18) . . . . ?
C4 C1B C6B C5B -176.6(10) . . . . ?
C4B C5B C6B C1B -2.2(17) . . . . ?
C4B C5B C6B C7B 176.1(11) . . . . ?
C1B C6B C7B C8B 173.5(11) . . . . ?
C5B C6B C7B C8B -4.7(18) . . . . ?
C1B C6B C7B C1C -4.4(17) . . . . ?
C5B C6B C7B C1C 177.4(10) . . . . ?
C6B C7B C8B C2C -179.6(11) . . . . ?
C1C C7B C8B C2C -1.6(18) . . . . ?
C1 N1 C1C C7A -3.5(17) . . . . ?
C4 N1 C1C C7A -178.4(10) . . . . ?
C1 N1 C1C C7B 178.8(10) . . . . ?
C4 N1 C1C C7B 3.9(16) . . . . ?
C8A C7A C1C N1 176.4(10) . . . . ?
C6A C7A C1C N1 2.8(16) . . . . ?
C8A C7A C1C C7B -6.0(18) . . . . ?
C6A C7A C1C C7B -179.6(11) . . . . ?
C8B C7B C1C N1 -178.3(10) . . . . ?
C6B C7B C1C N1 -0.2(16) . . . . ?
C8B C7B C1C C7A 4.1(17) . . . . ?
C6B C7B C1C C7A -177.8(11) . . . . ?
C7B C8B C2C C8A 1.0(19) . . . . ?
C7A C8A C2C C8B -2.7(19) . . . . ?

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
C1D D1 O2 1.00 2.19 3.096(19) 150.6 1_655
O2M H2M O2 0.84 2.28 2.72(6) 113.7 2_667

_refine_diff_density_max         0.644
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.118

_shelxl_version_number           2013-2

# start Validation Reply Form
_vrf_PLAT026_hag4                
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        28% Check 
RESPONSE:The crystal was a very thin plate with dimensions 
0.12 x 0.01 x 0.01 giving a weak diffraction. 
Different kinds of crystals also from other solvents were measured
to obtain the best data. 
The data presented is the best that could be obtained.
;
_vrf_PLAT084_hag4                
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.50 Report
RESPONSE: The crystal was a very thin plate with dimensions 
0.12 x 0.01 x 0.01 giving a weak diffraction. 
Different kinds of crystals also from other solvents were measured
to obtain the best data. 
The data presented is the best that could be obtained.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/methanol'
