#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221652.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221652
loop_
_publ_author_name
'Wang, Yao'
'Wan, Rong'
'Yin, Li-He'
'Han, Feng'
'Wang, Peng'
_publ_section_title
;Diethyl
 {[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylamino](4-methoxyphenyl)methyl}phosphonate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o983
_journal_paper_doi               10.1107/S1600536809012471
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C20 H22 Cl2 N3 O4 P S'
_chemical_formula_sum            'C20 H22 Cl2 N3 O4 P S'
_chemical_formula_weight         502.34
_chemical_melting_point          59365
_chemical_name_systematic
;
Diethyl {[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylamino](4-
methoxyphenyl)methyl}phosphonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.74(3)
_cell_angle_beta                 112.16(3)
_cell_angle_gamma                103.05(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7100(19)
_cell_length_b                   11.825(2)
_cell_length_c                   11.845(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1183.9(6)
_computing_cell_refinement       'CAD4 EXPRESS  (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4592
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_correction_T_min  0.8740
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.975
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0691
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0281P)²+3.5816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1572
_reflns_number_gt                2864
_reflns_number_total             4316
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ez2165.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1183.9(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2221652
_cod_database_fobs_code          2221652
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.1915(3) -0.0588(2) 0.04559(17) 0.1292(9) Uani d . 1 . .
Cl Cl2 0.60795(15) 0.19354(15) 0.51042(15) 0.0812(5) Uani d . 1 . .
S S 0.45871(13) 0.26753(10) 0.68952(11) 0.0518(3) Uani d . 1 . .
P P 0.28539(13) 0.35163(11) 1.04983(12) 0.0508(3) Uani d . 1 . .
N N1 0.4404(4) 0.3110(3) 0.9121(3) 0.0524(10) Uani d . 1 . .
H H1A 0.4934 0.3843 0.9247 0.063 Uiso calc R 1 . .
O O1 0.1252(4) 0.2999(3) 0.9312(4) 0.0754(11) Uani d . 1 . .
C C1 -0.0855(9) 0.3620(8) 0.8045(8) 0.112 Uani d D 1 . .
H H1B -0.1550 0.2881 0.7427 0.168 Uiso calc R 1 . .
H H1C -0.1008 0.4286 0.7694 0.168 Uiso calc R 1 . .
H H1D -0.1069 0.3689 0.8777 0.168 Uiso calc R 1 . .
N N2 0.2791(5) 0.1297(3) 0.7581(3) 0.0541(10) Uani d . 1 . .
O O2 0.2564(4) 0.2931(3) 1.1510(3) 0.0698(10) Uani d . 1 . .
C C2 0.0749(9) 0.3624(9) 0.8405(8) 0.123(3) Uani d D 1 . .
H H2A 0.0851 0.3269 0.7658 0.148 Uiso calc R 1 . .
H H2B 0.1427 0.4451 0.8733 0.148 Uiso calc R 1 . .
O O3 0.3460(4) 0.4837(3) 1.0857(3) 0.0621(9) Uani d . 1 . .
N N3 0.2468(4) 0.0703(3) 0.6370(3) 0.0541(10) Uani d . 1 . .
C C3 0.2866(11) 0.4070(7) 1.3512(7) 0.127(3) Uani d D 1 . .
H H3A 0.3578 0.3667 1.3943 0.191 Uiso calc R 1 . .
H H3B 0.2285 0.4241 1.3981 0.191 Uiso calc R 1 . .
H H3C 0.3443 0.4808 1.3440 0.191 Uiso calc R 1 . .
O O4 0.9613(4) 0.3317(3) 1.4496(4) 0.0826(12) Uani d . 1 . .
C C4 0.1777(9) 0.3289(7) 1.2240(7) 0.100(2) Uani d D 1 . .
H H4A 0.1134 0.2577 1.2320 0.120 Uiso calc R 1 . .
H H4B 0.1091 0.3715 1.1796 0.120 Uiso calc R 1 . .
C C5 0.4108(5) 0.2749(4) 1.0145(4) 0.0461(10) Uani d . 1 . .
H H5A 0.3525 0.1888 0.9834 0.055 Uiso calc R 1 . .
C C6 0.5616(5) 0.2897(4) 1.1290(4) 0.0454(10) Uani d . 1 . .
C C7 0.6196(5) 0.1950(4) 1.1435(5) 0.0572(12) Uani d . 1 . .
H H7A 0.5671 0.1221 1.0821 0.069 Uiso calc R 1 . .
C C8 0.7548(5) 0.2052(4) 1.2475(5) 0.0583(12) Uani d . 1 . .
H H8A 0.7942 0.1406 1.2546 0.070 Uiso calc R 1 . .
C C9 0.8308(5) 0.3130(4) 1.3412(5) 0.0569(12) Uani d . 1 . .
C C10 0.7780(6) 0.4085(4) 1.3276(5) 0.0735(16) Uani d . 1 . .
H H10A 0.8300 0.4811 1.3896 0.088 Uiso calc R 1 . .
C C11 0.6447(6) 0.3977(4) 1.2197(5) 0.0670(15) Uani d . 1 . .
H H11A 0.6114 0.4647 1.2088 0.080 Uiso calc R 1 . .
C C13 0.3876(5) 0.2336(4) 0.7974(4) 0.0441(10) Uani d . 1 . .
C C14 0.3304(5) 0.1296(4) 0.5888(4) 0.0418(9) Uani d . 1 . .
C C15 0.3017(5) 0.0854(4) 0.4561(4) 0.0468(10) Uani d . 1 . .
C C16 0.1499(5) 0.0152(4) 0.3671(4) 0.0515(11) Uani d . 1 . .
H H16A 0.0708 -0.0020 0.3939 0.062 Uiso calc R 1 . .
C C17 0.1154(7) -0.0281(5) 0.2443(5) 0.0700(15) Uani d . 1 . .
H H17A 0.0133 -0.0731 0.1882 0.084 Uiso calc R 1 . .
C C18 0.2304(8) -0.0064(5) 0.2005(5) 0.0770(17) Uani d . 1 . .
C C19 0.3822(8) 0.0635(6) 0.2868(6) 0.0856(19) Uani d . 1 . .
H H19A 0.4608 0.0802 0.2595 0.103 Uiso calc R 1 . .
C C20 0.4161(6) 0.1077(4) 0.4115(5) 0.0553(12) Uani d . 1 . .
C C12 1.0077(7) 0.2351(6) 1.4818(7) 0.089(2) Uani d . 1 . .
H H12A 0.9175 0.1691 1.4638 0.133 Uiso calc R 1 . .
H H12B 1.0760 0.2571 1.5703 0.133 Uiso calc R 1 . .
H H12C 1.0619 0.2116 1.4339 0.133 Uiso calc R 1 . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 S C14 . . 87.0(2) ?
O3 P O2 . . 116.2(2) ?
O3 P O1 . . 113.2(2) ?
O2 P O1 . . 104.1(2) ?
O3 P C5 . . 115.3(2) ?
O2 P C5 . . 101.5(2) ?
O1 P C5 . . 105.2(2) ?
C13 N1 C5 . . 122.3(3) ?
C13 N1 H1A . . 118.8 ?
C5 N1 H1A . . 118.8 ?
C2 O1 P . . 122.8(4) ?
C2 C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C13 N2 N3 . . 111.7(4) ?
C4 O2 P . . 126.3(4) ?
O1 C2 C1 . . 113.6(7) ?
O1 C2 H2A . . 108.8 ?
C1 C2 H2A . . 108.8 ?
O1 C2 H2B . . 108.8 ?
C1 C2 H2B . . 108.8 ?
H2A C2 H2B . . 107.7 ?
C14 N3 N2 . . 113.4(3) ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C9 O4 C12 . . 119.5(4) ?
O2 C4 C3 . . 112.8(6) ?
O2 C4 H4A . . 109.0 ?
C3 C4 H4A . . 109.0 ?
O2 C4 H4B . . 109.0 ?
C3 C4 H4B . . 109.0 ?
H4A C4 H4B . . 107.8 ?
N1 C5 C6 . . 112.2(3) ?
N1 C5 P . . 109.5(3) ?
C6 C5 P . . 113.9(3) ?
N1 C5 H5A . . 106.9 ?
C6 C5 H5A . . 106.9 ?
P C5 H5A . . 106.9 ?
C7 C6 C11 . . 117.8(4) ?
C7 C6 C5 . . 120.3(4) ?
C11 C6 C5 . . 121.9(4) ?
C6 C7 C8 . . 121.6(5) ?
C6 C7 H7A . . 119.2 ?
C8 C7 H7A . . 119.2 ?
C7 C8 C9 . . 119.3(5) ?
C7 C8 H8A . . 120.4 ?
C9 C8 H8A . . 120.4 ?
C10 C9 O4 . . 115.6(4) ?
C10 C9 C8 . . 120.2(5) ?
O4 C9 C8 . . 124.2(4) ?
C9 C10 C11 . . 119.6(5) ?
C9 C10 H10A . . 120.2 ?
C11 C10 H10A . . 120.2 ?
C6 C11 C10 . . 121.4(5) ?
C6 C11 H11A . . 119.3 ?
C10 C11 H11A . . 119.3 ?
N2 C13 N1 . . 124.0(4) ?
N2 C13 S . . 114.6(3) ?
N1 C13 S . . 121.4(3) ?
N3 C14 C15 . . 121.0(4) ?
N3 C14 S . . 113.4(3) ?
C15 C14 S . . 125.3(3) ?
C20 C15 C16 . . 116.7(4) ?
C20 C15 C14 . . 124.2(4) ?
C16 C15 C14 . . 119.1(4) ?
C17 C16 C15 . . 122.2(5) ?
C17 C16 H16A . . 118.9 ?
C15 C16 H16A . . 118.9 ?
C16 C17 C18 . . 120.8(5) ?
C16 C17 H17A . . 119.6 ?
C18 C17 H17A . . 119.6 ?
C17 C18 C19 . . 118.2(5) ?
C17 C18 Cl1 . . 122.4(5) ?
C19 C18 Cl1 . . 119.5(4) ?
C20 C19 C18 . . 120.6(5) ?
C20 C19 H19A . . 119.7 ?
C18 C19 H19A . . 119.7 ?
C19 C20 C15 . . 121.5(5) ?
C19 C20 Cl2 . . 116.8(4) ?
C15 C20 Cl2 . . 121.7(4) ?
O4 C12 H12A . . 109.5 ?
O4 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O4 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C18 . 1.709(6) ?
Cl2 C20 . 1.736(5) ?
S C13 . 1.723(4) ?
S C14 . 1.733(4) ?
P O3 . 1.469(3) ?
P O2 . 1.553(4) ?
P O1 . 1.559(4) ?
P C5 . 1.803(5) ?
N1 C13 . 1.354(5) ?
N1 C5 . 1.449(5) ?
N1 H1A . 0.8600 ?
O1 C2 . 1.395(9) ?
C1 C2 . 1.450(8) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
N2 C13 . 1.306(5) ?
N2 N3 . 1.380(5) ?
O2 C4 . 1.430(7) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
N3 C14 . 1.301(5) ?
C3 C4 . 1.475(7) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
O4 C9 . 1.365(6) ?
O4 C12 . 1.374(7) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.526(6) ?
C5 H5A . 0.9800 ?
C6 C7 . 1.368(6) ?
C6 C11 . 1.378(6) ?
C7 C8 . 1.385(7) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.388(7) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.348(7) ?
C10 C11 . 1.398(7) ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9300 ?
C14 C15 . 1.475(6) ?
C15 C20 . 1.391(6) ?
C15 C16 . 1.408(6) ?
C16 C17 . 1.349(7) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.388(8) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.399(8) ?
C19 C20 . 1.373(7) ?
C19 H19A . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O3 2_667 0.8600 2.0000 2.805(5) 156.00 yes
C10 H10A O4 2_768 0.9300 2.5300 3.431(7) 163.00 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 P O1 C2 . . . . 24.0(6) ?
O2 P O1 C2 . . . . 151.1(6) ?
C5 P O1 C2 . . . . -102.7(6) ?
O3 P O2 C4 . . . . 46.8(6) ?
O1 P O2 C4 . . . . -78.3(5) ?
C5 P O2 C4 . . . . 172.6(5) ?
P O1 C2 C1 . . . . -133.6(6) ?
C13 N2 N3 C14 . . . . 0.1(6) ?
P O2 C4 C3 . . . . -98.2(7) ?
C13 N1 C5 C6 . . . . 118.7(4) ?
C13 N1 C5 P . . . . -113.8(4) ?
O3 P C5 N1 . . . . -58.4(3) ?
O2 P C5 N1 . . . . 175.2(3) ?
O1 P C5 N1 . . . . 67.0(3) ?
O3 P C5 C6 . . . . 68.1(3) ?
O2 P C5 C6 . . . . -58.3(3) ?
O1 P C5 C6 . . . . -166.5(3) ?
N1 C5 C6 C7 . . . . -93.9(5) ?
P C5 C6 C7 . . . . 141.0(4) ?
N1 C5 C6 C11 . . . . 85.2(6) ?
P C5 C6 C11 . . . . -39.9(6) ?
C11 C6 C7 C8 . . . . 1.9(7) ?
C5 C6 C7 C8 . . . . -178.9(4) ?
C6 C7 C8 C9 . . . . 1.9(8) ?
C12 O4 C9 C10 . . . . 168.9(6) ?
C12 O4 C9 C8 . . . . -12.1(9) ?
C7 C8 C9 C10 . . . . -3.5(8) ?
C7 C8 C9 O4 . . . . 177.5(5) ?
O4 C9 C10 C11 . . . . -179.8(5) ?
C8 C9 C10 C11 . . . . 1.1(9) ?
C7 C6 C11 C10 . . . . -4.4(8) ?
C5 C6 C11 C10 . . . . 176.5(5) ?
C9 C10 C11 C6 . . . . 2.9(10) ?
N3 N2 C13 N1 . . . . 179.2(4) ?
N3 N2 C13 S . . . . 0.2(5) ?
C5 N1 C13 N2 . . . . 15.7(7) ?
C5 N1 C13 S . . . . -165.4(3) ?
C14 S C13 N2 . . . . -0.3(4) ?
C14 S C13 N1 . . . . -179.3(4) ?
N2 N3 C14 C15 . . . . -174.2(4) ?
N2 N3 C14 S . . . . -0.4(5) ?
C13 S C14 N3 . . . . 0.4(4) ?
C13 S C14 C15 . . . . 173.9(4) ?
N3 C14 C15 C20 . . . . -150.9(5) ?
S C14 C15 C20 . . . . 36.0(7) ?
N3 C14 C15 C16 . . . . 28.6(7) ?
S C14 C15 C16 . . . . -144.4(4) ?
C20 C15 C16 C17 . . . . -0.5(7) ?
C14 C15 C16 C17 . . . . 180.0(5) ?
C15 C16 C17 C18 . . . . 1.0(9) ?
C16 C17 C18 C19 . . . . -1.2(9) ?
C16 C17 C18 Cl1 . . . . -179.6(5) ?
C17 C18 C19 C20 . . . . 0.9(10) ?
Cl1 C18 C19 C20 . . . . 179.3(5) ?
C18 C19 C20 C15 . . . . -0.4(10) ?
C18 C19 C20 Cl2 . . . . -179.9(5) ?
C16 C15 C20 C19 . . . . 0.2(8) ?
C14 C15 C20 C19 . . . . 179.7(5) ?
C16 C15 C20 Cl2 . . . . 179.6(4) ?
C14 C15 C20 Cl2 . . . . -0.8(7) ?
