# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
#TrackingRef 'CCDC11_9.txt'

_publ_contact_author             
# Name and address of author for correspondence
;
Prof. Dr. Walter Frank
Anorganische Chemie und Strukturchemie, Lehrstuhl II
Heinrich-Heine-Universit\"at D\"usseldorf
Universit\"atsstr. 1
40225 D\"usseldorf
Germany
;
_publ_contact_author_email       wfrank@uni-duesseldorf.de
_publ_contact_author_fax         '+49 211 81 14146'
_publ_contact_author_phone       '+49 211 81 13135'

_publ_section_title              
;
Blue-luminescent 5-(3-indolyl)oxazoles via microwave-assisted
three-component coupling-cycloisomerization-Fischer indole
synthesis
;

loop_
_publ_author_name
_publ_author_address

O.Grotkopp
; Organische Chemie und Makromolekulare Chemie, Lehrstuhl I
Heinrich-Heine-Universit\"at D\"usseldorf
Universit\"atsstr. 1
40225 D\"usseldorf
Germany
;
A.Ahmad
; Organische Chemie und Makromolekulare Chemie, Lehrstuhl I
Heinrich-Heine-Universit\"at D\"usseldorf
Universit\"atsstr. 1
40225 D\"usseldorf
Germany
;
W.Frank
; Anorganische Chemie und Strukturchemie, Lehrstuhl II
Heinrich-Heine-Universit\"at D\"usseldorf
Universit\"atsstr. 1
40225 D\"usseldorf
Germany
;
T.J.J.Muller
; Anorganische Chemie und Strukturchemie, Lehrstuhl II
Heinrich-Heine-Universit\"at D\"usseldorf
Universit\"atsstr. 1
40225 D\"usseldorf
Germany
;

data_opus901a
_database_code_depnum_ccdc_archive 'CCDC 834591'
#TrackingRef 'CCDC11_9.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 Cl3 N2 O'
_chemical_formula_sum            'C24 H15 Cl3 N2 O'
_chemical_formula_weight         453.73

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   'P 21/c'

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                   7.5836(5)
_cell_length_b                   16.6354(15)
_cell_length_c                   16.7866(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.485(8)
_cell_angle_gamma                90.00
_cell_volume                     2099.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    3074
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.45

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(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  'Stoe IPDS'
_diffrn_measurement_method       \f-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8681
_diffrn_reflns_av_R_equivalents  0.0968
_diffrn_reflns_av_sigmaI/netI    0.2897
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3606
_reflns_number_gt                1006
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'EXPOSE (Stoe & Cie, 1996)'
_computing_cell_refinement       'CELL (Stoe & Cie, 1996)'
_computing_data_reduction        'INTEGRATE (Stoe & Cie, 1996)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3606
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1556
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0501
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.19414(16) 0.64723(7) 0.05358(8) 0.0700(4) Uani 1 1 d . . .
Cl2 Cl 1.05237(14) 0.06980(8) 0.16768(8) 0.0745(4) Uani 1 1 d . . .
Cl3 Cl 0.6050(2) 0.06662(9) -0.18346(10) 0.1126(6) Uani 1 1 d . . .
O1 O 0.1362(3) 0.33054(17) 0.15176(18) 0.0533(8) Uani 1 1 d . . .
N1 N 0.3059(4) 0.3382(2) -0.0967(3) 0.0462(9) Uani 1 1 d . . .
H1 H 0.3203 0.3242 -0.1447 0.09(2) Uiso 1 1 calc R . .
N2 N 0.2814(4) 0.2451(2) 0.2381(2) 0.0475(10) Uani 1 1 d . . .
C1 C 0.2886(4) 0.3310(2) 0.0352(3) 0.0401(11) Uani 1 1 d . . .
C3 C 0.3088(5) 0.2864(3) -0.0322(3) 0.0429(11) Uani 1 1 d . . .
C4 C 0.2762(5) 0.4160(3) -0.0725(3) 0.0414(11) Uani 1 1 d . . .
C5 C 0.2667(4) 0.4142(3) 0.0106(3) 0.0413(11) Uani 1 1 d . . .
C6 C 0.2429(5) 0.4859(3) 0.0500(3) 0.0489(12) Uani 1 1 d . . .
H61 H 0.2380 0.4868 0.1051 0.059 Uiso 1 1 calc R . .
C7 C 0.2268(5) 0.5554(3) 0.0061(3) 0.0481(12) Uani 1 1 d . . .
C8 C 0.2339(5) 0.5570(3) -0.0759(3) 0.0537(12) Uani 1 1 d . . .
H81 H 0.2208 0.6053 -0.1038 0.064 Uiso 1 1 calc R . .
C9 C 0.2605(5) 0.4864(3) -0.1159(3) 0.0538(13) Uani 1 1 d . . .
H91 H 0.2677 0.4864 -0.1708 0.065 Uiso 1 1 calc R . .
C10 C 0.2792(5) 0.3020(2) 0.1165(3) 0.0407(11) Uani 1 1 d . . .
C11 C 0.3713(5) 0.2508(2) 0.1702(3) 0.0395(11) Uani 1 1 d . . .
C12 C 0.1499(5) 0.2938(3) 0.2243(3) 0.0450(12) Uani 1 1 d . . .
C13 C 0.0118(5) 0.3146(3) 0.2764(3) 0.0726(16) Uani 1 1 d . . .
H131 H 0.0183 0.2776 0.3205 0.109 Uiso 1 1 calc R . .
H132 H -0.1038 0.3115 0.2455 0.109 Uiso 1 1 calc R . .
H133 H 0.0319 0.3683 0.2967 0.109 Uiso 1 1 calc R . .
C14 C 0.5382(5) 0.2077(2) 0.1693(3) 0.0417(11) Uani 1 1 d . . .
C15 C 0.5977(5) 0.1507(3) 0.2278(3) 0.0603(13) Uani 1 1 d . . .
H151 H 0.5278 0.1399 0.2681 0.072 Uiso 1 1 calc R . .
C16 C 0.7543(6) 0.1104(3) 0.2281(3) 0.0657(15) Uani 1 1 d . . .
H161 H 0.7902 0.0737 0.2688 0.079 Uiso 1 1 calc R . .
C17 C 0.8590(5) 0.1235(3) 0.1688(3) 0.0536(13) Uani 1 1 d . . .
C18 C 0.8071(5) 0.1801(3) 0.1110(3) 0.0503(13) Uani 1 1 d . . .
H181 H 0.8791 0.1910 0.0715 0.060 Uiso 1 1 calc R . .
C19 C 0.6492(5) 0.2209(3) 0.1110(3) 0.0508(12) Uani 1 1 d . . .
H191 H 0.6158 0.2584 0.0707 0.061 Uiso 1 1 calc R . .
C20 C 0.3359(5) 0.2004(3) -0.0448(3) 0.0449(11) Uani 1 1 d . . .
C21 C 0.2444(5) 0.1432(3) -0.0083(3) 0.0503(12) Uani 1 1 d . . .
H211 H 0.1683 0.1588 0.0281 0.060 Uiso 1 1 calc R . .
C22 C 0.2632(5) 0.0643(3) -0.0242(3) 0.0641(13) Uani 1 1 d . . .
H221 H 0.1999 0.0264 0.0014 0.077 Uiso 1 1 calc R . .
C23 C 0.3749(6) 0.0388(3) -0.0780(3) 0.0722(16) Uani 1 1 d . . .
H231 H 0.3866 -0.0155 -0.0893 0.087 Uiso 1 1 calc R . .
C24 C 0.4680(5) 0.0960(3) -0.1141(3) 0.0565(13) Uani 1 1 d . . .
C25 C 0.4505(5) 0.1757(3) -0.0977(3) 0.0494(12) Uani 1 1 d . . .
H251 H 0.5159 0.2136 -0.1222 0.059 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0903(9) 0.0498(7) 0.0694(11) -0.0078(7) 0.0088(7) -0.0003(7)
Cl2 0.0691(8) 0.0825(10) 0.0738(11) 0.0135(9) 0.0163(7) 0.0302(7)
Cl3 0.1361(12) 0.0845(11) 0.1348(16) -0.0140(11) 0.0845(11) 0.0238(10)
O1 0.0525(17) 0.068(2) 0.039(2) 0.0027(18) 0.0080(15) 0.0150(15)
N1 0.053(2) 0.054(3) 0.033(3) 0.003(2) 0.0086(17) 0.0046(18)
N2 0.050(2) 0.054(2) 0.039(3) 0.0039(19) 0.008(2) 0.0102(19)
C1 0.045(2) 0.049(3) 0.028(3) 0.001(2) 0.009(2) 0.006(2)
C3 0.044(3) 0.052(3) 0.033(3) 0.004(3) 0.006(2) 0.005(2)
C4 0.047(3) 0.043(3) 0.035(4) -0.003(3) 0.008(2) 0.003(2)
C5 0.039(2) 0.045(3) 0.042(4) -0.005(2) 0.010(2) 0.006(2)
C6 0.058(3) 0.057(3) 0.031(3) 0.003(3) 0.003(2) 0.000(2)
C7 0.047(3) 0.051(3) 0.046(4) 0.004(3) 0.003(2) -0.002(2)
C8 0.062(3) 0.047(3) 0.052(4) 0.014(3) 0.004(2) 0.003(2)
C9 0.061(3) 0.056(3) 0.044(4) 0.008(3) 0.005(2) 0.000(2)
C10 0.043(3) 0.044(3) 0.037(3) 0.001(2) 0.013(2) 0.007(2)
C11 0.046(3) 0.046(3) 0.028(3) 0.003(2) 0.009(2) 0.003(2)
C12 0.054(3) 0.057(3) 0.026(3) 0.003(2) 0.010(2) 0.007(2)
C13 0.063(3) 0.105(4) 0.052(4) 0.002(3) 0.017(3) 0.019(3)
C14 0.051(3) 0.038(3) 0.036(3) 0.010(2) 0.006(2) 0.008(2)
C15 0.074(3) 0.067(3) 0.043(4) 0.012(3) 0.020(3) 0.016(3)
C16 0.084(3) 0.068(3) 0.050(4) 0.024(3) 0.026(3) 0.040(3)
C17 0.063(3) 0.054(3) 0.043(4) 0.004(3) 0.006(3) 0.008(2)
C18 0.045(3) 0.060(3) 0.049(4) 0.004(3) 0.018(2) 0.001(2)
C19 0.055(3) 0.060(3) 0.039(3) 0.009(2) 0.010(2) 0.002(2)
C20 0.046(3) 0.048(3) 0.040(3) 0.002(2) 0.005(2) 0.000(2)
C21 0.056(3) 0.046(3) 0.053(4) -0.005(3) 0.020(2) 0.004(2)
C22 0.068(3) 0.062(3) 0.067(4) -0.003(3) 0.023(3) -0.003(3)
C23 0.099(4) 0.049(3) 0.071(5) -0.005(3) 0.020(3) 0.008(3)
C24 0.062(3) 0.046(3) 0.064(4) 0.004(3) 0.019(3) 0.016(3)
C25 0.040(2) 0.048(3) 0.062(4) 0.004(3) 0.017(2) 0.007(2)

_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
Cl1 C7 1.756(5) . ?
Cl2 C17 1.719(4) . ?
Cl3 C24 1.728(4) . ?
O1 C12 1.355(5) . ?
O1 C10 1.386(4) . ?
N1 C3 1.381(5) . ?
N1 C4 1.383(5) . ?
N1 H1 0.8600 . ?
N2 C12 1.282(4) . ?
N2 C11 1.405(5) . ?
C1 C3 1.378(5) . ?
C1 C5 1.447(6) . ?
C1 C10 1.458(5) . ?
C3 C20 1.465(5) . ?
C4 C9 1.375(5) . ?
C4 C5 1.408(5) . ?
C5 C6 1.388(5) . ?
C6 C7 1.368(6) . ?
C6 H61 0.9300 . ?
C7 C8 1.384(5) . ?
C8 C9 1.381(6) . ?
C8 H81 0.9300 . ?
C9 H91 0.9300 . ?
C10 C11 1.365(5) . ?
C11 C14 1.456(5) . ?
C12 C13 1.490(5) . ?
C13 H131 0.9600 . ?
C13 H132 0.9600 . ?
C13 H133 0.9600 . ?
C14 C19 1.389(5) . ?
C14 C15 1.398(5) . ?
C15 C16 1.364(5) . ?
C15 H151 0.9300 . ?
C16 C17 1.369(6) . ?
C16 H161 0.9300 . ?
C17 C18 1.373(5) . ?
C18 C19 1.376(5) . ?
C18 H181 0.9300 . ?
C19 H191 0.9300 . ?
C20 C21 1.370(5) . ?
C20 C25 1.383(5) . ?
C21 C22 1.351(6) . ?
C21 H211 0.9300 . ?
C22 C23 1.382(6) . ?
C22 H221 0.9300 . ?
C23 C24 1.372(6) . ?
C23 H231 0.9300 . ?
C24 C25 1.365(5) . ?
C25 H251 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
C12 O1 C10 104.9(3) . . ?
C3 N1 C4 109.9(4) . . ?
C3 N1 H1 125.0 . . ?
C4 N1 H1 125.0 . . ?
C12 N2 C11 105.0(3) . . ?
C3 C1 C5 107.6(4) . . ?
C3 C1 C10 127.9(4) . . ?
C5 C1 C10 124.4(4) . . ?
C1 C3 N1 108.4(4) . . ?
C1 C3 C20 132.6(4) . . ?
N1 C3 C20 119.0(4) . . ?
C9 C4 N1 130.3(4) . . ?
C9 C4 C5 122.1(4) . . ?
N1 C4 C5 107.6(4) . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 C1 134.7(5) . . ?
C4 C5 C1 106.5(4) . . ?
C7 C6 C5 118.5(4) . . ?
C7 C6 H61 120.7 . . ?
C5 C6 H61 120.7 . . ?
C6 C7 C8 122.7(4) . . ?
C6 C7 Cl1 119.9(4) . . ?
C8 C7 Cl1 117.4(4) . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H81 120.2 . . ?
C7 C8 H81 120.2 . . ?
C4 C9 C8 118.3(4) . . ?
C4 C9 H91 120.8 . . ?
C8 C9 H91 120.8 . . ?
C11 C10 O1 107.0(4) . . ?
C11 C10 C1 137.9(4) . . ?
O1 C10 C1 115.0(3) . . ?
C10 C11 N2 108.5(3) . . ?
C10 C11 C14 132.1(4) . . ?
N2 C11 C14 119.3(4) . . ?
N2 C12 O1 114.5(3) . . ?
N2 C12 C13 129.1(4) . . ?
O1 C12 C13 116.4(4) . . ?
C12 C13 H131 109.5 . . ?
C12 C13 H132 109.5 . . ?
H131 C13 H132 109.5 . . ?
C12 C13 H133 109.5 . . ?
H131 C13 H133 109.5 . . ?
H132 C13 H133 109.5 . . ?
C19 C14 C15 115.6(4) . . ?
C19 C14 C11 122.5(4) . . ?
C15 C14 C11 121.8(4) . . ?
C16 C15 C14 122.5(4) . . ?
C16 C15 H151 118.7 . . ?
C14 C15 H151 118.7 . . ?
C17 C16 C15 120.4(4) . . ?
C17 C16 H161 119.8 . . ?
C15 C16 H161 119.8 . . ?
C16 C17 C18 118.9(4) . . ?
C16 C17 Cl2 120.1(4) . . ?
C18 C17 Cl2 121.0(4) . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H181 119.7 . . ?
C19 C18 H181 119.7 . . ?
C18 C19 C14 122.0(4) . . ?
C18 C19 H191 119.0 . . ?
C14 C19 H191 119.0 . . ?
C21 C20 C25 118.6(4) . . ?
C21 C20 C3 121.7(4) . . ?
C25 C20 C3 119.6(4) . . ?
C22 C21 C20 120.9(4) . . ?
C22 C21 H211 119.6 . . ?
C20 C21 H211 119.6 . . ?
C21 C22 C23 121.1(5) . . ?
C21 C22 H221 119.4 . . ?
C23 C22 H221 119.4 . . ?
C24 C23 C22 118.1(4) . . ?
C24 C23 H231 121.0 . . ?
C22 C23 H231 121.0 . . ?
C25 C24 C23 121.0(4) . . ?
C25 C24 Cl3 119.6(4) . . ?
C23 C24 Cl3 119.4(4) . . ?
C24 C25 C20 120.3(4) . . ?
C24 C25 H251 119.9 . . ?
C20 C25 H251 119.9 . . ?

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
C5 C1 C3 N1 1.8(4) . . . . ?
C10 C1 C3 N1 178.3(3) . . . . ?
C5 C1 C3 C20 179.9(4) . . . . ?
C10 C1 C3 C20 -3.6(7) . . . . ?
C4 N1 C3 C1 -2.5(4) . . . . ?
C4 N1 C3 C20 179.1(3) . . . . ?
C3 N1 C4 C9 -179.1(4) . . . . ?
C3 N1 C4 C5 2.3(4) . . . . ?
C9 C4 C5 C6 -0.8(6) . . . . ?
N1 C4 C5 C6 178.0(3) . . . . ?
C9 C4 C5 C1 -179.9(3) . . . . ?
N1 C4 C5 C1 -1.1(4) . . . . ?
C3 C1 C5 C6 -179.4(4) . . . . ?
C10 C1 C5 C6 3.9(7) . . . . ?
C3 C1 C5 C4 -0.4(4) . . . . ?
C10 C1 C5 C4 -177.1(3) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
C1 C5 C6 C7 179.9(4) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
C5 C6 C7 Cl1 179.3(3) . . . . ?
C6 C7 C8 C9 -0.9(6) . . . . ?
Cl1 C7 C8 C9 179.6(3) . . . . ?
N1 C4 C9 C8 -178.8(4) . . . . ?
C5 C4 C9 C8 -0.3(6) . . . . ?
C7 C8 C9 C4 1.1(6) . . . . ?
C12 O1 C10 C11 -0.8(4) . . . . ?
C12 O1 C10 C1 177.5(3) . . . . ?
C3 C1 C10 C11 48.4(7) . . . . ?
C5 C1 C10 C11 -135.6(5) . . . . ?
C3 C1 C10 O1 -129.3(4) . . . . ?
C5 C1 C10 O1 46.7(5) . . . . ?
O1 C10 C11 N2 2.2(4) . . . . ?
C1 C10 C11 N2 -175.6(4) . . . . ?
O1 C10 C11 C14 -174.9(4) . . . . ?
C1 C10 C11 C14 7.3(8) . . . . ?
C12 N2 C11 C10 -2.8(4) . . . . ?
C12 N2 C11 C14 174.8(4) . . . . ?
C11 N2 C12 O1 2.4(5) . . . . ?
C11 N2 C12 C13 -178.0(4) . . . . ?
C10 O1 C12 N2 -1.0(5) . . . . ?
C10 O1 C12 C13 179.3(4) . . . . ?
C10 C11 C14 C19 8.0(7) . . . . ?
N2 C11 C14 C19 -168.9(4) . . . . ?
C10 C11 C14 C15 -172.6(5) . . . . ?
N2 C11 C14 C15 10.5(6) . . . . ?
C19 C14 C15 C16 0.0(7) . . . . ?
C11 C14 C15 C16 -179.5(4) . . . . ?
C14 C15 C16 C17 -1.3(7) . . . . ?
C15 C16 C17 C18 2.5(7) . . . . ?
C15 C16 C17 Cl2 -177.7(3) . . . . ?
C16 C17 C18 C19 -2.3(7) . . . . ?
Cl2 C17 C18 C19 177.9(3) . . . . ?
C17 C18 C19 C14 1.0(7) . . . . ?
C15 C14 C19 C18 0.2(7) . . . . ?
C11 C14 C19 C18 179.6(4) . . . . ?
C1 C3 C20 C21 41.8(7) . . . . ?
N1 C3 C20 C21 -140.3(4) . . . . ?
C1 C3 C20 C25 -141.2(5) . . . . ?
N1 C3 C20 C25 36.7(6) . . . . ?
C25 C20 C21 C22 -1.0(7) . . . . ?
C3 C20 C21 C22 176.1(4) . . . . ?
C20 C21 C22 C23 -0.1(7) . . . . ?
C21 C22 C23 C24 0.7(7) . . . . ?
C22 C23 C24 C25 -0.2(8) . . . . ?
C22 C23 C24 Cl3 -178.5(4) . . . . ?
C23 C24 C25 C20 -0.9(7) . . . . ?
Cl3 C24 C25 C20 177.4(3) . . . . ?
C21 C20 C25 C24 1.5(7) . . . . ?
C3 C20 C25 C24 -175.6(4) . . . . ?

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
N1 H1 N2 0.86 2.27 3.084(6) 159.0 4_565

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035