#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/42/2224273.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_2224273
loop_
_publ_author_name
'Chen, Hua'
'Yang, Huibin'
'Yu, Haibo'
'Li, Bin'
_publ_section_title
;
 Ethyl
 3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylate
;
_journal_coeditor_code           HB5251
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3267
_journal_paper_doi               10.1107/S1600536809050673
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H11 Br Cl N3 O2'
_chemical_formula_moiety         'C11 H11 Br Cl N3 O2'
_chemical_formula_sum            'C11 H11 Br Cl N3 O2'
_chemical_formula_weight         332.59
_chemical_name_systematic
;
Ethyl
3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.388(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.9977(18)
_cell_length_b                   10.8520(17)
_cell_length_c                   20.762(3)
_cell_measurement_reflns_used    2849
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.43
_cell_measurement_theta_min      2.53
_cell_volume                     2698.5(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13418
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    3.242
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.488
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0421
_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)+(0.0609P)²+0.7833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                2823
_reflns_number_total             4760
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5251.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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        2698.4(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224273
_cod_database_fobs_code          2224273
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Br Br1 0.61938(4) 0.12589(5) 0.11537(3) 0.0919(2) Uani d . 1 . .
Br Br2 0.12166(4) 1.34462(4) 0.11712(3) 0.0871(2) Uani d . 1 . .
Cl Cl1 0.84050(8) 0.53502(11) 0.12056(6) 0.0843(4) Uani d . 1 . .
Cl Cl2 0.33983(8) 0.94532(12) 0.10673(7) 0.0940(4) Uani d . 1 . .
O O1 0.4918(3) 0.6080(3) 0.20858(15) 0.0867(10) Uani d . 1 . .
O O2 0.3214(2) 0.5466(3) 0.17635(13) 0.0802(9) Uani d . 1 . .
O O3 0.0011(3) 0.8736(3) 0.20050(14) 0.0864(10) Uani d . 1 . .
O O4 -0.1747(2) 0.9229(3) 0.17066(12) 0.0680(8) Uani d . 1 . .
N N1 0.5454(2) 0.6660(3) 0.05716(14) 0.0553(8) Uani d . 1 . .
N N2 0.5862(2) 0.4848(3) 0.11040(15) 0.0610(9) Uani d . 1 . .
N N3 0.6393(3) 0.3738(3) 0.10056(16) 0.0601(9) Uani d . 1 . .
N N4 0.0445(2) 0.8001(3) 0.05316(15) 0.0577(8) Uani d . 1 . .
N N5 0.0807(2) 0.9898(3) 0.09552(19) 0.0750(10) Uani d . 1 . .
N N6 0.1371(2) 1.0989(3) 0.09295(15) 0.0579(8) Uani d . 1 . .
C C1 0.5772(3) 0.7712(4) 0.03040(18) 0.0640(11) Uani d . 1 . .
H H1 0.5218 0.8257 0.0153 0.077 Uiso calc R 1 . .
C C2 0.6850(3) 0.8036(4) 0.02391(19) 0.0700(12) Uani d . 1 . .
H H2 0.7031 0.8752 0.0023 0.084 Uiso calc R 1 . .
C C3 0.7664(3) 0.7272(4) 0.05023(19) 0.0619(11) Uani d . 1 . .
H H3 0.8413 0.7475 0.0475 0.074 Uiso calc R 1 . .
C C4 0.7373(3) 0.6211(4) 0.08063(18) 0.0548(10) Uani d . 1 . .
C C5 0.6239(3) 0.5907(3) 0.08114(16) 0.0477(9) Uani d . 1 . .
C C6 0.5731(3) 0.2893(4) 0.11589(18) 0.0595(10) Uani d . 1 . .
C C7 0.4634(3) 0.3298(4) 0.13789(19) 0.0610(10) Uani d . 1 . .
H H7A 0.4583 0.3175 0.1839 0.073 Uiso calc R 1 . .
H H7B 0.4019 0.2878 0.1147 0.073 Uiso calc R 1 . .
C C8 0.4669(3) 0.4674(3) 0.12040(17) 0.0528(9) Uani d . 1 . .
H H8 0.4219 0.4833 0.0803 0.063 Uiso calc R 1 . .
C C9 0.4312(3) 0.5498(4) 0.17334(18) 0.0592(10) Uani d . 1 . .
C C10 0.2759(5) 0.6186(6) 0.2280(3) 0.119(2) Uani d . 1 . .
H H10A 0.3045 0.5872 0.2695 0.143 Uiso calc R 1 . .
H H10B 0.2990 0.7039 0.2246 0.143 Uiso calc R 1 . .
C C11 0.1599(6) 0.6115(7) 0.2238(3) 0.159(3) Uani d . 1 . .
H H11A 0.1319 0.6407 0.1823 0.238 Uiso calc R 1 . .
H H11B 0.1303 0.6614 0.2569 0.238 Uiso calc R 1 . .
H H11C 0.1373 0.5274 0.2292 0.238 Uiso calc R 1 . .
C C12 0.0767(3) 0.6904(4) 0.03225(19) 0.0664(11) Uani d . 1 . .
H H12 0.0218 0.6335 0.0197 0.080 Uiso calc R 1 . .
C C13 0.1851(3) 0.6570(4) 0.0282(2) 0.0708(12) Uani d . 1 . .
H H13 0.2042 0.5807 0.0117 0.085 Uiso calc R 1 . .
C C14 0.2656(3) 0.7401(4) 0.0494(2) 0.0658(11) Uani d . 1 . .
H H14 0.3407 0.7203 0.0474 0.079 Uiso calc R 1 . .
C C15 0.2355(3) 0.8510(4) 0.07329(19) 0.0556(10) Uani d . 1 . .
C C16 0.1219(3) 0.8812(3) 0.07301(17) 0.0490(9) Uani d . 1 . .
C C17 0.0712(3) 1.1825(4) 0.10999(18) 0.0561(10) Uani d . 1 . .
C C18 -0.0415(3) 1.1433(4) 0.1270(2) 0.0679(12) Uani d . 1 . .
H H18A -0.0997 1.1861 0.1013 0.081 Uiso calc R 1 . .
H H18B -0.0524 1.1557 0.1724 0.081 Uiso calc R 1 . .
C C19 -0.0372(3) 1.0054(3) 0.10966(17) 0.0534(9) Uani d . 1 . .
H H19 -0.0863 0.9873 0.0715 0.064 Uiso calc R 1 . .
C C20 -0.0653(3) 0.9256(4) 0.16513(18) 0.0551(10) Uani d . 1 . .
C C21 -0.2137(5) 0.8554(5) 0.2256(2) 0.0970(17) Uani d . 1 . .
H H21A -0.1850 0.7719 0.2256 0.116 Uiso calc R 1 . .
H H21B -0.1870 0.8950 0.2654 0.116 Uiso calc R 1 . .
C C22 -0.3344(5) 0.8532(6) 0.2213(3) 0.133(3) Uani d . 1 . .
H H22A -0.3623 0.9361 0.2203 0.199 Uiso calc R 1 . .
H H22B -0.3606 0.8109 0.2581 0.199 Uiso calc R 1 . .
H H22C -0.3603 0.8111 0.1826 0.199 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C9 O2 C10 . . 115.9(3) ?
C20 O4 C21 . . 116.4(3) ?
C5 N1 C1 . . 118.1(3) ?
N3 N2 C5 . . 119.5(3) ?
N3 N2 C8 . . 111.7(3) ?
C5 N2 C8 . . 120.8(3) ?
C6 N3 N2 . . 107.0(3) ?
C16 N4 C12 . . 118.8(3) ?
N6 N5 C16 . . 122.8(3) ?
N6 N5 C19 . . 113.2(3) ?
C16 N5 C19 . . 122.5(3) ?
C17 N6 N5 . . 106.9(3) ?
N1 C1 C2 . . 124.1(4) ?
N1 C1 H1 . . 118.0 ?
C2 C1 H1 . . 118.0 ?
C1 C2 C3 . . 117.8(4) ?
C1 C2 H2 . . 121.1 ?
C3 C2 H2 . . 121.1 ?
C4 C3 C2 . . 119.8(4) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 118.5(3) ?
C3 C4 Cl1 . . 118.8(3) ?
C5 C4 Cl1 . . 122.6(3) ?
N1 C5 N2 . . 115.7(3) ?
N1 C5 C4 . . 121.4(3) ?
N2 C5 C4 . . 122.7(3) ?
N3 C6 C7 . . 116.3(4) ?
N3 C6 Br1 . . 119.9(3) ?
C7 C6 Br1 . . 123.7(3) ?
C6 C7 C8 . . 100.2(3) ?
C6 C7 H7A . . 111.7 ?
C8 C7 H7A . . 111.7 ?
C6 C7 H7B . . 111.7 ?
C8 C7 H7B . . 111.7 ?
H7A C7 H7B . . 109.5 ?
N2 C8 C9 . . 110.5(3) ?
N2 C8 C7 . . 101.4(3) ?
C9 C8 C7 . . 113.2(3) ?
N2 C8 H8 . . 110.5 ?
C9 C8 H8 . . 110.5 ?
C7 C8 H8 . . 110.5 ?
O1 C9 O2 . . 124.2(4) ?
O1 C9 C8 . . 125.4(4) ?
O2 C9 C8 . . 110.3(3) ?
C11 C10 O2 . . 109.9(5) ?
C11 C10 H10A . . 109.7 ?
O2 C10 H10A . . 109.7 ?
C11 C10 H10B . . 109.7 ?
O2 C10 H10B . . 109.7 ?
H10A C10 H10B . . 108.2 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N4 C12 C13 . . 123.8(4) ?
N4 C12 H12 . . 118.1 ?
C13 C12 H12 . . 118.1 ?
C12 C13 C14 . . 117.5(4) ?
C12 C13 H13 . . 121.2 ?
C14 C13 H13 . . 121.2 ?
C15 C14 C13 . . 120.1(4) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 119.0(4) ?
C14 C15 Cl2 . . 118.0(3) ?
C16 C15 Cl2 . . 122.9(3) ?
N4 C16 N5 . . 114.6(3) ?
N4 C16 C15 . . 120.6(3) ?
N5 C16 C15 . . 124.8(3) ?
N6 C17 C18 . . 117.0(4) ?
N6 C17 Br2 . . 119.6(3) ?
C18 C17 Br2 . . 123.3(3) ?
C17 C18 C19 . . 100.3(3) ?
C17 C18 H18A . . 111.7 ?
C19 C18 H18A . . 111.7 ?
C17 C18 H18B . . 111.7 ?
C19 C18 H18B . . 111.7 ?
H18A C18 H18B . . 109.5 ?
N5 C19 C20 . . 110.5(3) ?
N5 C19 C18 . . 101.8(3) ?
C20 C19 C18 . . 111.7(3) ?
N5 C19 H19 . . 110.8 ?
C20 C19 H19 . . 110.8 ?
C18 C19 H19 . . 110.8 ?
O3 C20 O4 . . 124.4(4) ?
O3 C20 C19 . . 125.2(4) ?
O4 C20 C19 . . 110.4(3) ?
C22 C21 O4 . . 109.1(4) ?
C22 C21 H21A . . 109.9 ?
O4 C21 H21A . . 109.9 ?
C22 C21 H21B . . 109.9 ?
O4 C21 H21B . . 109.9 ?
H21A C21 H21B . . 108.3 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 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
Br1 C6 . 1.858(4) ?
Br2 C17 . 1.863(4) ?
Cl1 C4 . 1.724(4) ?
Cl2 C15 . 1.731(4) ?
O1 C9 . 1.184(4) ?
O2 C9 . 1.323(4) ?
O2 C10 . 1.459(5) ?
O3 C20 . 1.192(4) ?
O4 C20 . 1.325(4) ?
O4 C21 . 1.455(5) ?
N1 C5 . 1.321(4) ?
N1 C1 . 1.335(5) ?
N2 N3 . 1.383(4) ?
N2 C5 . 1.388(5) ?
N2 C8 . 1.471(4) ?
N3 C6 . 1.266(5) ?
N4 C16 . 1.327(5) ?
N4 C12 . 1.332(5) ?
N5 N6 . 1.366(4) ?
N5 C16 . 1.371(5) ?
N5 C19 . 1.470(4) ?
N6 C17 . 1.267(5) ?
C1 C2 . 1.355(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.370(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.368(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.401(5) ?
C6 C7 . 1.486(5) ?
C7 C8 . 1.538(5) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.499(5) ?
C8 H8 . 0.9800 ?
C10 C11 . 1.392(9) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.357(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.374(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.358(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.401(5) ?
C17 C18 . 1.480(5) ?
C18 C19 . 1.541(5) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C20 . 1.495(5) ?
C19 H19 . 0.9800 ?
C21 C22 . 1.445(8) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
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
C5 N2 N3 C6 . . . . -161.8(3) ?
C8 N2 N3 C6 . . . . -12.7(4) ?
C16 N5 N6 C17 . . . . 172.2(4) ?
C19 N5 N6 C17 . . . . 6.1(4) ?
C5 N1 C1 C2 . . . . 2.8(6) ?
N1 C1 C2 C3 . . . . -4.5(6) ?
C1 C2 C3 C4 . . . . 1.3(6) ?
C2 C3 C4 C5 . . . . 3.0(6) ?
C2 C3 C4 Cl1 . . . . -173.3(3) ?
C1 N1 C5 N2 . . . . 177.8(3) ?
C1 N1 C5 C4 . . . . 2.0(5) ?
N3 N2 C5 N1 . . . . 139.1(3) ?
C8 N2 C5 N1 . . . . -7.1(5) ?
N3 N2 C5 C4 . . . . -45.1(5) ?
C8 N2 C5 C4 . . . . 168.6(3) ?
C3 C4 C5 N1 . . . . -4.9(5) ?
Cl1 C4 C5 N1 . . . . 171.4(3) ?
C3 C4 C5 N2 . . . . 179.7(3) ?
Cl1 C4 C5 N2 . . . . -4.1(5) ?
N2 N3 C6 C7 . . . . 0.8(5) ?
N2 N3 C6 Br1 . . . . -175.1(2) ?
N3 C6 C7 C8 . . . . 10.3(4) ?
Br1 C6 C7 C8 . . . . -173.9(3) ?
N3 N2 C8 C9 . . . . 138.6(3) ?
C5 N2 C8 C9 . . . . -72.8(4) ?
N3 N2 C8 C7 . . . . 18.3(4) ?
C5 N2 C8 C7 . . . . 166.9(3) ?
C6 C7 C8 N2 . . . . -15.7(3) ?
C6 C7 C8 C9 . . . . -134.1(3) ?
C10 O2 C9 O1 . . . . -1.4(7) ?
C10 O2 C9 C8 . . . . 177.2(4) ?
N2 C8 C9 O1 . . . . -9.9(6) ?
C7 C8 C9 O1 . . . . 103.0(5) ?
N2 C8 C9 O2 . . . . 171.5(3) ?
C7 C8 C9 O2 . . . . -75.6(4) ?
C9 O2 C10 C11 . . . . 177.3(5) ?
C16 N4 C12 C13 . . . . -1.9(6) ?
N4 C12 C13 C14 . . . . 2.6(7) ?
C12 C13 C14 C15 . . . . 0.0(6) ?
C13 C14 C15 C16 . . . . -3.0(6) ?
C13 C14 C15 Cl2 . . . . 173.6(3) ?
C12 N4 C16 N5 . . . . -178.0(4) ?
C12 N4 C16 C15 . . . . -1.4(5) ?
N6 N5 C16 N4 . . . . -152.2(4) ?
C19 N5 C16 N4 . . . . 12.6(5) ?
N6 N5 C16 C15 . . . . 31.3(6) ?
C19 N5 C16 C15 . . . . -163.9(3) ?
C14 C15 C16 N4 . . . . 3.8(6) ?
Cl2 C15 C16 N4 . . . . -172.6(3) ?
C14 C15 C16 N5 . . . . -179.9(4) ?
Cl2 C15 C16 N5 . . . . 3.7(6) ?
N5 N6 C17 C18 . . . . 0.0(5) ?
N5 N6 C17 Br2 . . . . 176.5(3) ?
N6 C17 C18 C19 . . . . -5.4(5) ?
Br2 C17 C18 C19 . . . . 178.2(3) ?
N6 N5 C19 C20 . . . . -127.9(4) ?
C16 N5 C19 C20 . . . . 66.0(5) ?
N6 N5 C19 C18 . . . . -9.0(4) ?
C16 N5 C19 C18 . . . . -175.2(4) ?
C17 C18 C19 N5 . . . . 7.8(4) ?
C17 C18 C19 C20 . . . . 125.8(3) ?
C21 O4 C20 O3 . . . . 2.7(6) ?
C21 O4 C20 C19 . . . . -175.9(4) ?
N5 C19 C20 O3 . . . . 12.4(5) ?
C18 C19 C20 O3 . . . . -100.1(5) ?
N5 C19 C20 O4 . . . . -169.0(3) ?
C18 C19 C20 O4 . . . . 78.4(4) ?
C20 O4 C21 C22 . . . . -175.3(4) ?
