#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025634.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025634
loop_
_publ_author_name
'Hai-Ming Guo'
'Pu Li'
'Hong-Ying Niu'
'Dong-Chao Wang'
'Gui-Rong Qu'
_publ_section_title
;
 Direct Synthesis of 6-Arylpurines by Reaction of 6-Chloropurines with
 Activated Aromatics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6016
_journal_page_last               6018
_journal_paper_doi               10.1021/jo1010334
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C22 H15 Cl N4 O'
_chemical_formula_sum            'C22 H15 Cl N4 O'
_chemical_formula_weight         386.83
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.588(13)
_cell_length_b                   8.804(6)
_cell_length_c                   22.536(16)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.30
_cell_measurement_theta_min      2.84
_cell_volume                     3688(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24559
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3433
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0477P)²+2.3909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                2346
_reflns_number_total             3433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1010334_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025634
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C16 C 0.0541(2) 0.1402(5) 0.9469(2) 0.0512(7) Uani 0.588(3) 1 d PU A 1
H16A H 0.0255 0.0501 0.9544 0.061 Uiso 0.588(3) 1 calc PR A 1
H16B H 0.0708 0.1778 0.9849 0.061 Uiso 0.588(3) 1 calc PR A 1
C17 C 0.11849(12) 0.0951(3) 0.91051(12) 0.0513(6) Uani 0.588(3) 1 d PGU A 1
C18 C 0.17202(15) 0.0068(4) 0.93629(12) 0.0655(8) Uani 0.588(3) 1 d PGU A 1
C19 C 0.22784(16) -0.0497(4) 0.90169(17) 0.0974(14) Uani 0.588(3) 1 d PGU A 1
H19 H 0.2637 -0.1088 0.9189 0.117 Uiso 0.588(3) 1 calc PR A 1
C20 C 0.23014(17) -0.0179(5) 0.84131(16) 0.1160(16) Uani 0.588(3) 1 d PGU A 1
H20 H 0.2675 -0.0557 0.8182 0.139 Uiso 0.588(3) 1 calc PR A 1
C21 C 0.17661(19) 0.0704(5) 0.81552(12) 0.1005(15) Uani 0.588(3) 1 d PGU A 1
H21 H 0.1781 0.0917 0.7751 0.121 Uiso 0.588(3) 1 calc PR A 1
C22 C 0.12079(15) 0.1269(4) 0.85012(12) 0.0704(10) Uani 0.588(3) 1 d PGU A 1
H22 H 0.0850 0.1860 0.8329 0.085 Uiso 0.588(3) 1 calc PR A 1
C16' C 0.0450(4) 0.1237(9) 0.9407(4) 0.0512(7) Uani 0.412(3) 1 d P A 2
H16C H 0.0169 0.0335 0.9320 0.061 Uiso 0.412(3) 1 calc PR A 2
H16D H 0.0513 0.1298 0.9834 0.061 Uiso 0.412(3) 1 calc PR A 2
C17' C 0.11766(18) 0.1123(5) 0.91088(19) 0.0513(6) Uani 0.412(3) 1 d PG A 2
C18' C 0.1712(2) 0.0366(6) 0.94219(19) 0.0655(8) Uani 0.412(3) 1 d PG A 2
C19' C 0.2404(2) 0.0276(7) 0.9191(2) 0.0974(14) Uani 0.412(3) 1 d PG A 2
H19' H 0.2762 -0.0231 0.9400 0.117 Uiso 0.412(3) 1 calc PR A 2
C20' C 0.2561(2) 0.0942(7) 0.8647(3) 0.1160(16) Uani 0.412(3) 1 d PG A 2
H20' H 0.3024 0.0881 0.8492 0.139 Uiso 0.412(3) 1 calc PR A 2
C21' C 0.2025(3) 0.1698(7) 0.8334(2) 0.1005(15) Uani 0.412(3) 1 d PG A 2
H21' H 0.2130 0.2144 0.7970 0.121 Uiso 0.412(3) 1 calc PR A 2
C22' C 0.1333(2) 0.1789(6) 0.85647(19) 0.0704(10) Uani 0.412(3) 1 d PG A 2
H22' H 0.0975 0.2295 0.8355 0.085 Uiso 0.412(3) 1 calc PR A 2
C1 C -0.22655(10) 0.8712(2) 0.84130(10) 0.0477(5) Uani 1 1 d . . .
C2 C -0.22953(11) 0.7644(2) 0.88434(11) 0.0556(6) Uani 1 1 d . . .
H2 H -0.2736 0.7385 0.9011 0.067 Uiso 1 1 calc R . .
C3 C -0.16674(11) 0.6930(2) 0.90365(11) 0.0557(6) Uani 1 1 d . . .
H3 H -0.1700 0.6187 0.9329 0.067 Uiso 1 1 calc R . .
C4 C -0.10039(10) 0.7289(2) 0.88092(9) 0.0452(5) Uani 1 1 d . . .
C5 C -0.09522(10) 0.8439(2) 0.83703(9) 0.0428(5) Uani 1 1 d . . .
C6 C -0.02929(11) 0.8876(3) 0.81012(10) 0.0550(6) Uani 1 1 d . . .
H6 H 0.0133 0.8416 0.8221 0.066 Uiso 1 1 calc R . .
C7 C -0.02757(13) 0.9955(3) 0.76711(11) 0.0721(8) Uani 1 1 d . . .
H7 H 0.0160 1.0202 0.7493 0.087 Uiso 1 1 calc R . .
C8 C -0.09036(13) 1.0698(3) 0.74932(12) 0.0800(8) Uani 1 1 d . . .
H8 H -0.0884 1.1448 0.7203 0.096 Uiso 1 1 calc R . .
C9 C -0.15427(12) 1.0323(3) 0.77448(11) 0.0643(7) Uani 1 1 d . . .
H9 H -0.1957 1.0838 0.7631 0.077 Uiso 1 1 calc R . .
C10 C -0.15890(10) 0.9172(2) 0.81732(9) 0.0462(5) Uani 1 1 d . . .
C11 C -0.03785(10) 0.6400(2) 0.90155(9) 0.0457(5) Uani 1 1 d . . .
C12 C -0.03815(10) 0.4826(2) 0.90049(9) 0.0433(5) Uani 1 1 d . A .
C13 C -0.05746(11) 0.2462(2) 0.89213(10) 0.0532(6) Uani 1 1 d . A .
H13 H -0.0789 0.1536 0.8830 0.064 Uiso 1 1 calc R . .
C14 C 0.02090(10) 0.4086(2) 0.92487(9) 0.0451(5) Uani 1 1 d . A .
C15 C 0.07380(12) 0.6241(3) 0.94502(11) 0.0651(7) Uani 1 1 d . . .
H15 H 0.1133 0.6770 0.9596 0.078 Uiso 1 1 calc R . .
Cl1 Cl 0.16330(4) -0.04187(8) 1.00954(3) 0.0812(2) Uani 1 1 d . . .
N1 N 0.02036(9) 0.7102(2) 0.92372(9) 0.0576(5) Uani 1 1 d . . .
N2 N 0.07845(9) 0.4737(2) 0.94836(9) 0.0569(5) Uani 1 1 d . . .
N3 N 0.00716(8) 0.25667(19) 0.91988(8) 0.0493(5) Uani 1 1 d . . .
N4 N -0.08701(8) 0.37642(19) 0.87938(8) 0.0503(5) Uani 1 1 d . . .
O1 O -0.28527(7) 0.93734(18) 0.81712(7) 0.0637(5) Uani 1 1 d . . .
H1 H -0.3215 0.9071 0.8342 0.096 Uiso 1 1 calc R . .
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'
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
N3 C16 C17 115.4(4) . . ?
N3 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
N3 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C22 120.0 . . ?
C18 C17 C16 119.3(2) . . ?
C22 C17 C16 120.3(2) . . ?
C17 C18 C19 120.0 . . ?
C17 C18 Cl1 118.36(16) . . ?
C19 C18 Cl1 121.44(16) . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.0 . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
N3 C16' C17' 110.1(5) . . ?
N3 C16' H16C 109.6 . . ?
C17' C16' H16C 109.6 . . ?
N3 C16' H16D 109.6 . . ?
C17' C16' H16D 109.6 . . ?
H16C C16' H16D 108.2 . . ?
C18' C17' C22' 120.0 . . ?
C18' C17' C16' 116.5(4) . . ?
C22' C17' C16' 123.5(4) . . ?
C17' C18' C19' 120.0 . . ?
C17' C18' Cl1 126.5(2) . . ?
C19' C18' Cl1 113.4(2) . . ?
C18' C19' C20' 120.0 . . ?
C18' C19' H19' 120.0 . . ?
C20' C19' H19' 120.0 . . ?
C19' C20' C21' 120.0 . . ?
C19' C20' H20' 120.0 . . ?
C21' C20' H20' 120.0 . . ?
C22' C21' C20' 120.0 . . ?
C22' C21' H21' 120.0 . . ?
C20' C21' H21' 120.0 . . ?
C21' C22' C17' 120.0 . . ?
C21' C22' H22' 120.0 . . ?
C17' C22' H22' 120.0 . . ?
C2 C1 O1 123.76(18) . . ?
C2 C1 C10 120.34(18) . . ?
O1 C1 C10 115.88(19) . . ?
C1 C2 C3 120.18(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 122.1(2) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.04(18) . . ?
C3 C4 C11 117.90(19) . . ?
C5 C4 C11 122.99(17) . . ?
C4 C5 C10 119.08(17) . . ?
C4 C5 C6 123.34(18) . . ?
C10 C5 C6 117.55(19) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 119.53(18) . . ?
C9 C10 C1 121.32(19) . . ?
C5 C10 C1 119.15(18) . . ?
N1 C11 C12 118.05(18) . . ?
N1 C11 C4 120.48(18) . . ?
C12 C11 C4 121.44(18) . . ?
C11 C12 N4 133.00(18) . . ?
C11 C12 C14 117.30(18) . . ?
N4 C12 C14 109.70(18) . . ?
N4 C13 N3 114.50(19) . . ?
N4 C13 H13 122.8 . . ?
N3 C13 H13 122.8 . . ?
N2 C14 N3 127.41(18) . . ?
N2 C14 C12 126.42(19) . . ?
N3 C14 C12 106.17(17) . . ?
N2 C15 N1 129.3(2) . . ?
N2 C15 H15 115.4 . . ?
N1 C15 H15 115.4 . . ?
C18' Cl1 C18 9.9(2) . . ?
C15 N1 C11 118.04(19) . . ?
C14 N2 C15 110.84(19) . . ?
C13 N3 C14 105.66(17) . . ?
C13 N3 C16' 121.7(3) . . ?
C14 N3 C16' 132.5(4) . . ?
C13 N3 C16 131.7(2) . . ?
C14 N3 C16 122.4(2) . . ?
C16' N3 C16 10.2(4) . . ?
C13 N4 C12 103.95(17) . . ?
C1 O1 H1 109.5 . . ?
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
C16 N3 1.477(5) . ?
C16 C17 1.504(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.3900 . ?
C17 C22 1.3900 . ?
C18 C19 1.3900 . ?
C18 Cl1 1.713(3) . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C16' N3 1.444(8) . ?
C16' C17' 1.513(8) . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?
C17' C18' 1.3900 . ?
C17' C22' 1.3900 . ?
C18' C19' 1.3900 . ?
C18' Cl1 1.674(4) . ?
C19' C20' 1.3900 . ?
C19' H19' 0.9300 . ?
C20' C21' 1.3900 . ?
C20' H20' 0.9300 . ?
C21' C22' 1.3900 . ?
C21' H21' 0.9300 . ?
C22' H22' 0.9300 . ?
C1 C2 1.352(3) . ?
C1 O1 1.352(2) . ?
C1 C10 1.427(3) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.418(3) . ?
C4 C11 1.477(3) . ?
C5 C10 1.420(3) . ?
C5 C6 1.420(3) . ?
C6 C7 1.357(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.357(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.402(3) . ?
C9 H9 0.9300 . ?
C11 N1 1.343(3) . ?
C11 C12 1.386(3) . ?
C12 N4 1.387(3) . ?
C12 C14 1.389(3) . ?
C13 N4 1.304(3) . ?
C13 N3 1.357(3) . ?
C13 H13 0.9300 . ?
C14 N2 1.324(3) . ?
C14 N3 1.367(3) . ?
C15 N2 1.329(3) . ?
C15 N1 1.339(3) . ?
C15 H15 0.9300 . ?
O1 H1 0.8200 . ?
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
O1 H1 N4 0.82 2.00 2.809(3) 168.8 8_565
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 C16 C17 C18 168.9(2) . . . . ?
N3 C16 C17 C22 -18.2(4) . . . . ?
C22 C17 C18 C19 0.0 . . . . ?
C16 C17 C18 C19 172.9(3) . . . . ?
C22 C17 C18 Cl1 -175.0(2) . . . . ?
C16 C17 C18 Cl1 -2.0(3) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
Cl1 C18 C19 C20 174.8(2) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C17 0.0 . . . . ?
C18 C17 C22 C21 0.0 . . . . ?
C16 C17 C22 C21 -172.9(3) . . . . ?
N3 C16' C17' C18' 153.0(4) . . . . ?
N3 C16' C17' C22' -23.9(7) . . . . ?
C22' C17' C18' C19' 0.0 . . . . ?
C16' C17' C18' C19' -177.0(5) . . . . ?
C22' C17' C18' Cl1 176.5(4) . . . . ?
C16' C17' C18' Cl1 -0.4(5) . . . . ?
C17' C18' C19' C20' 0.0 . . . . ?
Cl1 C18' C19' C20' -177.0(4) . . . . ?
C18' C19' C20' C21' 0.0 . . . . ?
C19' C20' C21' C22' 0.0 . . . . ?
C20' C21' C22' C17' 0.0 . . . . ?
C18' C17' C22' C21' 0.0 . . . . ?
C16' C17' C22' C21' 176.7(5) . . . . ?
O1 C1 C2 C3 174.9(2) . . . . ?
C10 C1 C2 C3 -3.1(3) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 C11 -176.2(2) . . . . ?
C3 C4 C5 C10 -0.8(3) . . . . ?
C11 C4 C5 C10 176.19(19) . . . . ?
C3 C4 C5 C6 -179.0(2) . . . . ?
C11 C4 C5 C6 -2.0(3) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 1.9(4) . . . . ?
C6 C7 C8 C9 -1.1(4) . . . . ?
C7 C8 C9 C10 -1.5(4) . . . . ?
C8 C9 C10 C5 3.3(4) . . . . ?
C8 C9 C10 C1 -176.2(2) . . . . ?
C4 C5 C10 C9 179.2(2) . . . . ?
C6 C5 C10 C9 -2.5(3) . . . . ?
C4 C5 C10 C1 -1.3(3) . . . . ?
C6 C5 C10 C1 177.05(19) . . . . ?
C2 C1 C10 C9 -177.2(2) . . . . ?
O1 C1 C10 C9 4.6(3) . . . . ?
C2 C1 C10 C5 3.2(3) . . . . ?
O1 C1 C10 C5 -174.95(18) . . . . ?
C3 C4 C11 N1 -126.6(2) . . . . ?
C5 C4 C11 N1 56.4(3) . . . . ?
C3 C4 C11 C12 51.3(3) . . . . ?
C5 C4 C11 C12 -125.7(2) . . . . ?
N1 C11 C12 N4 -177.4(2) . . . . ?
C4 C11 C12 N4 4.6(4) . . . . ?
N1 C11 C12 C14 2.6(3) . . . . ?
C4 C11 C12 C14 -175.31(18) . . . . ?
C11 C12 C14 N2 -1.2(3) . . . . ?
N4 C12 C14 N2 178.9(2) . . . . ?
C11 C12 C14 N3 178.52(18) . . . . ?
N4 C12 C14 N3 -1.4(2) . . . . ?
C17' C18' Cl1 C18 109.1(13) . . . . ?
C19' C18' Cl1 C18 -74.2(12) . . . . ?
C17 C18 Cl1 C18' -58.4(12) . . . . ?
C19 C18 Cl1 C18' 126.7(12) . . . . ?
N2 C15 N1 C11 -0.7(4) . . . . ?
C12 C11 N1 C15 -1.9(3) . . . . ?
C4 C11 N1 C15 176.1(2) . . . . ?
N3 C14 N2 C15 179.3(2) . . . . ?
C12 C14 N2 C15 -1.0(3) . . . . ?
N1 C15 N2 C14 2.1(4) . . . . ?
N4 C13 N3 C14 -0.7(3) . . . . ?
N4 C13 N3 C16' 175.7(4) . . . . ?
N4 C13 N3 C16 172.9(3) . . . . ?
N2 C14 N3 C13 -179.0(2) . . . . ?
C12 C14 N3 C13 1.3(2) . . . . ?
N2 C14 N3 C16' 5.0(6) . . . . ?
C12 C14 N3 C16' -174.7(5) . . . . ?
N2 C14 N3 C16 6.6(4) . . . . ?
C12 C14 N3 C16 -173.1(3) . . . . ?
C17' C16' N3 C13 120.1(4) . . . . ?
C17' C16' N3 C14 -64.5(7) . . . . ?
C17' C16' N3 C16 -72(3) . . . . ?
C17 C16 N3 C13 102.9(4) . . . . ?
C17 C16 N3 C14 -84.3(4) . . . . ?
C17 C16 N3 C16' 89(3) . . . . ?
N3 C13 N4 C12 -0.1(2) . . . . ?
C11 C12 N4 C13 -179.0(2) . . . . ?
C14 C12 N4 C13 1.0(2) . . . . ?
