#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227405.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_2227405
loop_
_publ_author_name
'Wang, Hai-Quan'
'Chen, Wang-Zhong'
'Chen, Wen-Hua'
'Xi, Bao-Min'
_publ_section_title
;
 2-(5-Bromopentyl)-4-chloro-5-[2-(4-methoxyphenyl)ethylamino]pyridazin-3(2H)-one
;
_journal_coeditor_code           EZ2210
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2215
_journal_paper_doi               10.1107/S1600536810030102
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H23 Br Cl N3 O2'
_chemical_formula_moiety         'C18 H23 Br Cl N3 O2'
_chemical_formula_sum            'C18 H23 Br Cl N3 O2'
_chemical_formula_weight         428.75
_chemical_name_systematic
;
2-(5-Bromopentyl)-4-chloro-5-[2-(4-methoxyphenyl)ethylamino]pyridazin-
3(2H)-one
;
_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
_cell_angle_alpha                94.803(2)
_cell_angle_beta                 96.380(2)
_cell_angle_gamma                91.035(2)
_cell_formula_units_Z            4
_cell_length_a                   9.7728(14)
_cell_length_b                   12.6178(19)
_cell_length_c                   15.500(2)
_cell_measurement_reflns_used    16062
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      3.0
_cell_volume                     1892.1(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Rigaku Mercury'
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15893
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.330
_exptl_absorpt_correction_T_max  0.9751
_exptl_absorpt_correction_T_min  0.9325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Flake
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.386
_refine_diff_density_min         -0.880
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         8131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0444
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                6225
_reflns_number_total             8131
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ez2210.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-p 1'
_cod_database_code               2227405
_cod_database_fobs_code          2227405
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
Br Br1 0.30298(4) 0.50393(3) 0.45799(2) 0.02925(12) Uani d . 1 . .
Cl Cl1 0.17837(8) 0.99896(6) -0.02591(5) 0.02143(18) Uani d . 1 . .
O O1 0.2247(2) 0.80242(16) 0.06417(15) 0.0224(5) Uani d . 1 . .
O O2 0.9083(2) 1.48186(17) 0.40044(15) 0.0226(5) Uani d . 1 . .
C C8 0.4160(3) 1.0519(2) 0.0756(2) 0.0163(6) Uani d . 1 . .
C C12 0.5870(3) 1.3402(2) 0.2271(2) 0.0177(6) Uani d . 1 . .
N N3 0.4189(3) 1.14797(19) 0.04352(18) 0.0184(5) Uani d . 1 . .
H H3 0.3616 1.1592 -0.0026 0.022 Uiso calc R 1 . .
N N2 0.5283(3) 0.9306(2) 0.17251(18) 0.0200(6) Uani d . 1 . .
N N1 0.4273(3) 0.85810(19) 0.14458(17) 0.0185(6) Uani d . 1 . .
C C6 0.3153(3) 0.8731(2) 0.0839(2) 0.0179(6) Uani d . 1 . .
C C1 0.3895(4) 0.4850(2) 0.3507(2) 0.0221(7) Uani d . 1 . .
H H1A 0.4903 0.4804 0.3651 0.027 Uiso calc R 1 . .
H H1B 0.3552 0.4173 0.3177 0.027 Uiso calc R 1 . .
C C15 0.8034(3) 1.4410(2) 0.3407(2) 0.0183(6) Uani d . 1 . .
C C9 0.5230(3) 1.0221(2) 0.1399(2) 0.0183(6) Uani d . 1 . .
H H9 0.5947 1.0730 0.1599 0.022 Uiso calc R 1 . .
C C17 0.6400(3) 1.4397(2) 0.2130(2) 0.0182(6) Uani d . 1 . .
H H17 0.6026 1.4736 0.1636 0.022 Uiso calc R 1 . .
C C10 0.5136(3) 1.2340(2) 0.0825(2) 0.0195(6) Uani d . 1 . .
H H10A 0.5181 1.2886 0.0406 0.023 Uiso calc R 1 . .
H H10B 0.6069 1.2055 0.0941 0.023 Uiso calc R 1 . .
C C16 0.7462(3) 1.4910(2) 0.2694(2) 0.0181(6) Uani d . 1 . .
H H16 0.7791 1.5596 0.2591 0.022 Uiso calc R 1 . .
C C7 0.3153(3) 0.9743(2) 0.0495(2) 0.0167(6) Uani d . 1 . .
C C14 0.7528(3) 1.3408(2) 0.3553(2) 0.0214(7) Uani d . 1 . .
H H14 0.7913 1.3063 0.4042 0.026 Uiso calc R 1 . .
C C4 0.3957(4) 0.7748(3) 0.2796(2) 0.0288(8) Uani d . 1 . .
H H4A 0.2954 0.7865 0.2757 0.035 Uiso calc R 1 . .
H H4B 0.4434 0.8396 0.3102 0.035 Uiso calc R 1 . .
C C13 0.6468(3) 1.2917(2) 0.2989(2) 0.0210(7) Uani d . 1 . .
H H13 0.6140 1.2231 0.3093 0.025 Uiso calc R 1 . .
C C2 0.3588(3) 0.5764(2) 0.2945(2) 0.0219(7) Uani d . 1 . .
H H2A 0.3890 0.5579 0.2363 0.026 Uiso calc R 1 . .
H H2B 0.2581 0.5862 0.2864 0.026 Uiso calc R 1 . .
C C3 0.4294(4) 0.6802(3) 0.3332(2) 0.0296(8) Uani d . 1 . .
H H3A 0.5303 0.6708 0.3391 0.035 Uiso calc R 1 . .
H H3B 0.4023 0.6967 0.3924 0.035 Uiso calc R 1 . .
C C11 0.4702(3) 1.2862(2) 0.1676(2) 0.0208(7) Uani d . 1 . .
H H11A 0.3995 1.3392 0.1536 0.025 Uiso calc R 1 . .
H H11B 0.4274 1.2311 0.1987 0.025 Uiso calc R 1 . .
C C18 0.9452(4) 1.5921(2) 0.4003(2) 0.0251(7) Uani d . 1 . .
H H18A 0.9844 1.6039 0.3463 0.038 Uiso calc R 1 . .
H H18B 1.0135 1.6131 0.4503 0.038 Uiso calc R 1 . .
H H18C 0.8630 1.6348 0.4043 0.038 Uiso calc R 1 . .
C C5 0.4380(4) 0.7591(2) 0.1882(2) 0.0225(7) Uani d . 1 . .
H H5A 0.5341 0.7350 0.1912 0.027 Uiso calc R 1 . .
H H5B 0.3781 0.7031 0.1538 0.027 Uiso calc R 1 . .
Br Br2 1.17053(4) -0.11846(3) 0.48534(2) 0.03305(12) Uani d . 1 . .
Cl Cl2 1.32193(8) 0.51689(6) 1.02756(5) 0.02196(18) Uani d . 1 . .
O O3 1.2740(2) 0.29549(18) 0.94660(16) 0.0257(5) Uani d . 1 . .
N N6 1.0840(3) 0.64087(19) 0.95016(17) 0.0178(5) Uani d . 1 . .
H H6 1.1411 0.6650 0.9957 0.021 Uiso calc R 1 . .
N N4 1.0735(3) 0.32485(19) 0.86383(18) 0.0185(6) Uani d . 1 . .
N N5 0.9745(3) 0.3881(2) 0.83069(18) 0.0197(6) Uani d . 1 . .
O O4 0.6028(2) 0.9151(2) 0.60480(17) 0.0309(6) Uani d . 1 . .
C C35 0.8609(3) 0.8865(2) 0.7875(2) 0.0195(6) Uani d . 1 . .
H H35 0.8914 0.9247 0.8419 0.023 Uiso calc R 1 . .
C C26 1.1866(3) 0.4692(2) 0.9527(2) 0.0162(6) Uani d . 1 . .
C C25 1.0874(3) 0.5372(2) 0.9223(2) 0.0161(6) Uani d . 1 . .
C C27 1.1857(3) 0.3584(2) 0.9229(2) 0.0193(6) Uani d . 1 . .
C C20 1.1627(4) 0.0353(3) 0.6350(2) 0.0250(7) Uani d . 1 . .
H H20A 1.1397 0.0879 0.5920 0.030 Uiso calc R 1 . .
H H20B 1.2642 0.0338 0.6471 0.030 Uiso calc R 1 . .
C C24 0.9815(3) 0.4878(2) 0.8582(2) 0.0173(6) Uani d . 1 . .
H H24 0.9117 0.5320 0.8346 0.021 Uiso calc R 1 . .
C C34 0.7561(3) 0.9263(3) 0.7332(2) 0.0228(7) Uani d . 1 . .
H H34 0.7160 0.9917 0.7502 0.027 Uiso calc R 1 . .
C C28 0.9910(3) 0.7150(2) 0.9092(2) 0.0184(6) Uani d . 1 . .
H H28A 0.9869 0.7797 0.9495 0.022 Uiso calc R 1 . .
H H28B 0.8973 0.6821 0.8980 0.022 Uiso calc R 1 . .
C C32 0.7701(4) 0.7760(3) 0.6286(2) 0.0252(7) Uani d . 1 . .
H H32 0.7400 0.7382 0.5740 0.030 Uiso calc R 1 . .
C C31 0.8749(4) 0.7375(2) 0.6842(2) 0.0230(7) Uani d . 1 . .
H H31 0.9154 0.6723 0.6672 0.028 Uiso calc R 1 . .
C C29 1.0361(3) 0.7468(2) 0.8230(2) 0.0206(7) Uani d . 1 . .
H H29A 1.1123 0.8005 0.8360 0.025 Uiso calc R 1 . .
H H29B 1.0721 0.6835 0.7917 0.025 Uiso calc R 1 . .
C C30 0.9227(3) 0.7915(2) 0.7640(2) 0.0188(6) Uani d . 1 . .
C C33 0.7092(3) 0.8711(3) 0.6540(2) 0.0221(7) Uani d . 1 . .
C C23 1.0566(3) 0.2119(2) 0.8319(2) 0.0213(7) Uani d . 1 . .
H H23A 0.9571 0.1942 0.8172 0.026 Uiso calc R 1 . .
H H23B 1.0922 0.1681 0.8791 0.026 Uiso calc R 1 . .
C C22 1.1304(3) 0.1835(2) 0.7524(2) 0.0230(7) Uani d . 1 . .
H H22A 1.2309 0.1954 0.7679 0.028 Uiso calc R 1 . .
H H22B 1.0997 0.2302 0.7062 0.028 Uiso calc R 1 . .
C C21 1.1006(4) 0.0676(2) 0.7185(2) 0.0239(7) Uani d . 1 . .
H H21A 1.1370 0.0215 0.7639 0.029 Uiso calc R 1 . .
H H21B 0.9996 0.0551 0.7081 0.029 Uiso calc R 1 . .
C C36 0.5565(4) 0.8604(4) 0.5224(3) 0.0427(10) Uani d . 1 . .
H H36A 0.6336 0.8535 0.4871 0.064 Uiso calc R 1 . .
H H36B 0.4835 0.9006 0.4924 0.064 Uiso calc R 1 . .
H H36C 0.5205 0.7895 0.5309 0.064 Uiso calc R 1 . .
C C19 1.1062(4) -0.0739(3) 0.5981(2) 0.0277(8) Uani d . 1 . .
H H19A 1.0043 -0.0731 0.5909 0.033 Uiso calc R 1 . .
H H19B 1.1346 -0.1266 0.6400 0.033 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
C15 O2 C18 . . 117.8(2) ?
N3 C8 C7 . . 124.2(3) ?
N3 C8 C9 . . 121.2(3) ?
C7 C8 C9 . . 114.6(3) ?
C13 C12 C17 . . 117.5(3) ?
C13 C12 C11 . . 120.6(3) ?
C17 C12 C11 . . 121.9(3) ?
C8 N3 C10 . . 122.4(3) ?
C8 N3 H3 . . 118.8 ?
C10 N3 H3 . . 118.8 ?
C9 N2 N1 . . 118.1(3) ?
N2 N1 C6 . . 125.4(2) ?
N2 N1 C5 . . 114.3(3) ?
C6 N1 C5 . . 120.3(2) ?
O1 C6 N1 . . 120.7(3) ?
O1 C6 C7 . . 125.1(3) ?
N1 C6 C7 . . 114.3(3) ?
C2 C1 Br1 . . 111.3(2) ?
C2 C1 H1A . . 109.4 ?
Br1 C1 H1A . . 109.4 ?
C2 C1 H1B . . 109.4 ?
Br1 C1 H1B . . 109.4 ?
H1A C1 H1B . . 108.0 ?
O2 C15 C16 . . 125.3(3) ?
O2 C15 C14 . . 115.1(3) ?
C16 C15 C14 . . 119.5(3) ?
N2 C9 C8 . . 124.6(3) ?
N2 C9 H9 . . 117.7 ?
C8 C9 H9 . . 117.7 ?
C16 C17 C12 . . 121.9(3) ?
C16 C17 H17 . . 119.0 ?
C12 C17 H17 . . 119.0 ?
N3 C10 C11 . . 112.6(3) ?
N3 C10 H10A . . 109.1 ?
C11 C10 H10A . . 109.1 ?
N3 C10 H10B . . 109.1 ?
C11 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.8 ?
C15 C16 C17 . . 119.3(3) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C8 C7 C6 . . 123.1(3) ?
C8 C7 Cl1 . . 120.1(2) ?
C6 C7 Cl1 . . 116.8(2) ?
C13 C14 C15 . . 120.1(3) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C5 C4 C3 . . 113.0(3) ?
C5 C4 H4A . . 109.0 ?
C3 C4 H4A . . 109.0 ?
C5 C4 H4B . . 109.0 ?
C3 C4 H4B . . 109.0 ?
H4A C4 H4B . . 107.8 ?
C14 C13 C12 . . 121.6(3) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C3 C2 C1 . . 113.0(3) ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2B . . 109.0 ?
C1 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
C2 C3 C4 . . 114.1(3) ?
C2 C3 H3A . . 108.7 ?
C4 C3 H3A . . 108.7 ?
C2 C3 H3B . . 108.7 ?
C4 C3 H3B . . 108.7 ?
H3A C3 H3B . . 107.6 ?
C12 C11 C10 . . 113.7(3) ?
C12 C11 H11A . . 108.8 ?
C10 C11 H11A . . 108.8 ?
C12 C11 H11B . . 108.8 ?
C10 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
O2 C18 H18A . . 109.5 ?
O2 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O2 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N1 C5 C4 . . 111.2(3) ?
N1 C5 H5A . . 109.4 ?
C4 C5 H5A . . 109.4 ?
N1 C5 H5B . . 109.4 ?
C4 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C25 N6 C28 . . 123.6(3) ?
C25 N6 H6 . . 118.2 ?
C28 N6 H6 . . 118.2 ?
N5 N4 C27 . . 125.5(3) ?
N5 N4 C23 . . 114.9(3) ?
C27 N4 C23 . . 119.6(3) ?
C24 N5 N4 . . 117.8(3) ?
C33 O4 C36 . . 116.8(3) ?
C34 C35 C30 . . 121.2(3) ?
C34 C35 H35 . . 119.4 ?
C30 C35 H35 . . 119.4 ?
C25 C26 C27 . . 122.8(3) ?
C25 C26 Cl2 . . 120.1(2) ?
C27 C26 Cl2 . . 117.1(2) ?
N6 C25 C26 . . 124.2(3) ?
N6 C25 C24 . . 121.2(3) ?
C26 C25 C24 . . 114.6(3) ?
O3 C27 N4 . . 120.8(3) ?
O3 C27 C26 . . 124.9(3) ?
N4 C27 C26 . . 114.3(3) ?
C19 C20 C21 . . 109.5(3) ?
C19 C20 H20A . . 109.8 ?
C21 C20 H20A . . 109.8 ?
C19 C20 H20B . . 109.8 ?
C21 C20 H20B . . 109.8 ?
H20A C20 H20B . . 108.2 ?
N5 C24 C25 . . 125.0(3) ?
N5 C24 H24 . . 117.5 ?
C25 C24 H24 . . 117.5 ?
C35 C34 C33 . . 120.3(3) ?
C35 C34 H34 . . 119.9 ?
C33 C34 H34 . . 119.9 ?
N6 C28 C29 . . 112.3(3) ?
N6 C28 H28A . . 109.1 ?
C29 C28 H28A . . 109.1 ?
N6 C28 H28B . . 109.1 ?
C29 C28 H28B . . 109.1 ?
H28A C28 H28B . . 107.9 ?
C31 C32 C33 . . 119.1(3) ?
C31 C32 H32 . . 120.5 ?
C33 C32 H32 . . 120.5 ?
C32 C31 C30 . . 122.0(3) ?
C32 C31 H31 . . 119.0 ?
C30 C31 H31 . . 119.0 ?
C30 C29 C28 . . 113.9(3) ?
C30 C29 H29A . . 108.8 ?
C28 C29 H29A . . 108.8 ?
C30 C29 H29B . . 108.8 ?
C28 C29 H29B . . 108.8 ?
H29A C29 H29B . . 107.7 ?
C31 C30 C35 . . 117.8(3) ?
C31 C30 C29 . . 120.5(3) ?
C35 C30 C29 . . 121.7(3) ?
O4 C33 C34 . . 116.5(3) ?
O4 C33 C32 . . 123.8(3) ?
C34 C33 C32 . . 119.7(3) ?
N4 C23 C22 . . 113.1(2) ?
N4 C23 H23A . . 109.0 ?
C22 C23 H23A . . 109.0 ?
N4 C23 H23B . . 109.0 ?
C22 C23 H23B . . 109.0 ?
H23A C23 H23B . . 107.8 ?
C23 C22 C21 . . 110.6(3) ?
C23 C22 H22A . . 109.5 ?
C21 C22 H22A . . 109.5 ?
C23 C22 H22B . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 108.1 ?
C20 C21 C22 . . 113.7(3) ?
C20 C21 H21A . . 108.8 ?
C22 C21 H21A . . 108.8 ?
C20 C21 H21B . . 108.8 ?
C22 C21 H21B . . 108.8 ?
H21A C21 H21B . . 107.7 ?
O4 C36 H36A . . 109.5 ?
O4 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
O4 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C20 C19 Br2 . . 112.5(2) ?
C20 C19 H19A . . 109.1 ?
Br2 C19 H19A . . 109.1 ?
C20 C19 H19B . . 109.1 ?
Br2 C19 H19B . . 109.1 ?
H19A C19 H19B . . 107.8 ?
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 C1 . 1.947(3) ?
Cl1 C7 . 1.728(3) ?
O1 C6 . 1.240(4) ?
O2 C15 . 1.365(4) ?
O2 C18 . 1.431(4) ?
C8 N3 . 1.350(4) ?
C8 C7 . 1.378(4) ?
C8 C9 . 1.440(4) ?
C12 C13 . 1.392(5) ?
C12 C17 . 1.393(4) ?
C12 C11 . 1.501(4) ?
N3 C10 . 1.459(4) ?
N3 H3 . 0.8800 ?
N2 C9 . 1.297(4) ?
N2 N1 . 1.344(3) ?
N1 C6 . 1.388(4) ?
N1 C5 . 1.470(4) ?
C6 C7 . 1.425(4) ?
C1 C2 . 1.517(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C15 C16 . 1.388(4) ?
C15 C14 . 1.394(4) ?
C9 H9 . 0.9500 ?
C17 C16 . 1.392(4) ?
C17 H17 . 0.9500 ?
C10 C11 . 1.530(4) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C16 H16 . 0.9500 ?
C14 C13 . 1.381(5) ?
C14 H14 . 0.9500 ?
C4 C5 . 1.518(5) ?
C4 C3 . 1.532(5) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C13 H13 . 0.9500 ?
C2 C3 . 1.515(4) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
Br2 C19 . 1.964(3) ?
Cl2 C26 . 1.723(3) ?
O3 C27 . 1.230(4) ?
N6 C25 . 1.345(4) ?
N6 C28 . 1.451(4) ?
N6 H6 . 0.8800 ?
N4 N5 . 1.351(4) ?
N4 C27 . 1.383(4) ?
N4 C23 . 1.470(4) ?
N5 C24 . 1.293(4) ?
O4 C33 . 1.373(4) ?
O4 C36 . 1.423(5) ?
C35 C34 . 1.381(5) ?
C35 C30 . 1.391(4) ?
C35 H35 . 0.9500 ?
C26 C25 . 1.376(4) ?
C26 C27 . 1.436(4) ?
C25 C24 . 1.446(4) ?
C20 C19 . 1.518(4) ?
C20 C21 . 1.518(5) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C24 H24 . 0.9500 ?
C34 C33 . 1.387(5) ?
C34 H34 . 0.9500 ?
C28 C29 . 1.535(4) ?
C28 H28A . 0.9900 ?
C28 H28B . 0.9900 ?
C32 C31 . 1.386(5) ?
C32 C33 . 1.396(5) ?
C32 H32 . 0.9500 ?
C31 C30 . 1.390(5) ?
C31 H31 . 0.9500 ?
C29 C30 . 1.505(4) ?
C29 H29A . 0.9900 ?
C29 H29B . 0.9900 ?
C23 C22 . 1.517(5) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C22 C21 . 1.523(4) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C36 H36A . 0.9800 ?
C36 H36B . 0.9800 ?
C36 H36C . 0.9800 ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
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
N3 H3 O3 1_464 0.88 2.11 2.796(3) 134.5
N6 H6 O1 1_656 0.88 2.06 2.815(3) 143.3
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
C7 C8 N3 C10 . . . . 169.7(3) ?
C9 C8 N3 C10 . . . . -11.8(4) ?
C9 N2 N1 C6 . . . . -0.8(4) ?
C9 N2 N1 C5 . . . . -177.0(3) ?
N2 N1 C6 O1 . . . . -177.7(3) ?
C5 N1 C6 O1 . . . . -1.7(4) ?
N2 N1 C6 C7 . . . . 1.5(4) ?
C5 N1 C6 C7 . . . . 177.5(3) ?
C18 O2 C15 C16 . . . . 12.9(4) ?
C18 O2 C15 C14 . . . . -167.0(3) ?
N1 N2 C9 C8 . . . . 0.0(5) ?
N3 C8 C9 N2 . . . . -178.7(3) ?
C7 C8 C9 N2 . . . . 0.0(5) ?
C13 C12 C17 C16 . . . . -1.7(4) ?
C11 C12 C17 C16 . . . . 178.4(3) ?
C8 N3 C10 C11 . . . . -74.9(4) ?
O2 C15 C16 C17 . . . . 179.4(3) ?
C14 C15 C16 C17 . . . . -0.7(4) ?
C12 C17 C16 C15 . . . . 1.4(5) ?
N3 C8 C7 C6 . . . . 179.4(3) ?
C9 C8 C7 C6 . . . . 0.8(4) ?
N3 C8 C7 Cl1 . . . . -2.5(4) ?
C9 C8 C7 Cl1 . . . . 178.9(2) ?
O1 C6 C7 C8 . . . . 177.7(3) ?
N1 C6 C7 C8 . . . . -1.5(4) ?
O1 C6 C7 Cl1 . . . . -0.4(4) ?
N1 C6 C7 Cl1 . . . . -179.6(2) ?
O2 C15 C14 C13 . . . . -179.8(3) ?
C16 C15 C14 C13 . . . . 0.3(5) ?
C15 C14 C13 C12 . . . . -0.6(5) ?
C17 C12 C13 C14 . . . . 1.3(5) ?
C11 C12 C13 C14 . . . . -178.8(3) ?
Br1 C1 C2 C3 . . . . 69.2(3) ?
C1 C2 C3 C4 . . . . -177.7(3) ?
C5 C4 C3 C2 . . . . -60.4(4) ?
C13 C12 C11 C10 . . . . -101.8(3) ?
C17 C12 C11 C10 . . . . 78.1(4) ?
N3 C10 C11 C12 . . . . 156.1(3) ?
N2 N1 C5 C4 . . . . 75.2(3) ?
C6 N1 C5 C4 . . . . -101.2(3) ?
C3 C4 C5 N1 . . . . -169.8(3) ?
C27 N4 N5 C24 . . . . -2.6(4) ?
C23 N4 N5 C24 . . . . 178.0(3) ?
C28 N6 C25 C26 . . . . 170.9(3) ?
C28 N6 C25 C24 . . . . -11.1(4) ?
C27 C26 C25 N6 . . . . 178.7(3) ?
Cl2 C26 C25 N6 . . . . -3.2(4) ?
C27 C26 C25 C24 . . . . 0.5(4) ?
Cl2 C26 C25 C24 . . . . 178.6(2) ?
N5 N4 C27 O3 . . . . -176.9(3) ?
C23 N4 C27 O3 . . . . 2.6(4) ?
N5 N4 C27 C26 . . . . 3.9(4) ?
C23 N4 C27 C26 . . . . -176.7(3) ?
C25 C26 C27 O3 . . . . 178.1(3) ?
Cl2 C26 C27 O3 . . . . -0.1(4) ?
C25 C26 C27 N4 . . . . -2.7(4) ?
Cl2 C26 C27 N4 . . . . 179.2(2) ?
N4 N5 C24 C25 . . . . -0.2(5) ?
N6 C25 C24 N5 . . . . -177.2(3) ?
C26 C25 C24 N5 . . . . 1.1(5) ?
C30 C35 C34 C33 . . . . 0.7(5) ?
C25 N6 C28 C29 . . . . -75.2(4) ?
C33 C32 C31 C30 . . . . -0.9(5) ?
N6 C28 C29 C30 . . . . 160.2(3) ?
C32 C31 C30 C35 . . . . 0.4(5) ?
C32 C31 C30 C29 . . . . 179.6(3) ?
C34 C35 C30 C31 . . . . -0.3(5) ?
C34 C35 C30 C29 . . . . -179.5(3) ?
C28 C29 C30 C31 . . . . -114.7(3) ?
C28 C29 C30 C35 . . . . 64.4(4) ?
C36 O4 C33 C34 . . . . 178.4(3) ?
C36 O4 C33 C32 . . . . -1.8(5) ?
C35 C34 C33 O4 . . . . 178.7(3) ?
C35 C34 C33 C32 . . . . -1.1(5) ?
C31 C32 C33 O4 . . . . -178.6(3) ?
C31 C32 C33 C34 . . . . 1.2(5) ?
N5 N4 C23 C22 . . . . 91.8(3) ?
C27 N4 C23 C22 . . . . -87.7(4) ?
N4 C23 C22 C21 . . . . -175.9(3) ?
C19 C20 C21 C22 . . . . -169.8(3) ?
C23 C22 C21 C20 . . . . 175.8(3) ?
C21 C20 C19 Br2 . . . . 175.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079611
