#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/25/2202565.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_2202565
loop_
_publ_author_name
'Thamotharan, S'
'Parthasarathi, V'
'Sunagar, Vinay'
'Badami, Bharati'
'Schenk, Kurt J.'
_publ_section_title
;Ethyl
 4-[1-(4-bromophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yliminomethyl]phenoxyacetate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1272
_journal_page_last               o1274
_journal_paper_doi               10.1107/S1600536803016969
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C20 H19 Br N4 O4'
_chemical_formula_moiety         'C20 H19 Br N4 O4'
_chemical_formula_sum            'C20 H19 Br N4 O4'
_chemical_formula_weight         459.30
_chemical_melting_point          428
_chemical_name_systematic
;
Ethyl 4-[1-(4-bromophenyl)-3-methyl-5-oxo-4,5-dihydro-
1H-1,2,4-triazol-4-yliminomethyl]phenoxyacetate
;
_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   constr
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.407(6)
_cell_angle_beta                 94.601(7)
_cell_angle_gamma                103.763(6)
_cell_formula_units_Z            4
_cell_length_a                   8.5176(7)
_cell_length_b                   15.5566(12)
_cell_length_c                   17.2643(15)
_cell_measurement_reflns_used    15908
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.48
_cell_measurement_theta_min      2.37
_cell_volume                     1999.5(3)
_computing_cell_refinement       IPDS
_computing_data_collection       'IPDS (Stoe & Cie, 1997)'
_computing_data_reduction        IPDS
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF99 (Beurskens et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'Plane graphite'
_diffrn_radiation_source         'sealed LFF X-ray tube, 12 x 0.4 mm'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19783
_diffrn_reflns_theta_full        29.48
_diffrn_reflns_theta_max         29.48
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.091
_exptl_absorpt_correction_T_max  0.8606
_exptl_absorpt_correction_T_min  0.5370
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED in IPDS; Stoe & Cie, 1997)'
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       obelisk
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.419
_refine_ls_extinction_coef       0.0045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         10124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0552P)²+0.6771P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                6462
_reflns_number_total             10124
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6214.cif
_cod_data_source_block           I
_cod_database_code               2202565
_cod_database_fobs_code          2202565
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Br1A -0.07665(5) 1.04785(3) 0.66958(2) 0.07535(13) Uani d . 1 . . Br
O3A 0.1951(3) 0.63426(14) 0.60607(11) 0.0592(5) Uani d . 1 . . O
O20A 0.5662(3) 0.15699(16) 0.50014(13) 0.0664(6) Uani d . 1 . . O
O22A 0.3592(3) 0.0727(2) 0.58373(18) 0.0847(7) Uani d . 1 . . O
O23A 0.5634(3) 0.13732(18) 0.69870(15) 0.0736(6) Uani d . 1 . . O
N1A 0.0682(3) 0.62379(16) 0.40479(13) 0.0525(5) Uani d . 1 . . N
N2A 0.0964(3) 0.66883(15) 0.49445(12) 0.0462(5) Uani d . 1 . . N
N4A 0.1736(3) 0.53837(15) 0.45866(13) 0.0472(5) Uani d . 1 . . N
N12A 0.2362(3) 0.46170(16) 0.45262(14) 0.0509(5) Uani d . 1 . . N
C3A 0.1599(3) 0.61725(18) 0.53058(16) 0.0456(6) Uani d . 1 . . C
C5A 0.1154(4) 0.54634(19) 0.38626(16) 0.0504(6) Uani d . 1 . . C
C6A 0.0568(3) 0.75770(18) 0.53669(15) 0.0430(5) Uani d . 1 . . C
C7A -0.0169(3) 0.7947(2) 0.48736(16) 0.0489(6) Uani d . 1 . . C
H7A -0.0396 0.7612 0.4276 0.059 Uiso calc R 1 . . H
C8A -0.0566(3) 0.8808(2) 0.52657(17) 0.0508(6) Uani d . 1 . . C
H8A -0.1067 0.9056 0.4938 0.061 Uiso calc R 1 . . H
C9A -0.0210(3) 0.92937(19) 0.61458(16) 0.0484(6) Uani d . 1 . . C
C10A 0.0525(4) 0.8946(2) 0.66494(16) 0.0538(7) Uani d . 1 . . C
H10A 0.0759 0.9288 0.7246 0.065 Uiso calc R 1 . . H
C11A 0.0913(4) 0.8075(2) 0.62533(16) 0.0536(7) Uani d . 1 . . C
H11A 0.1406 0.7828 0.6585 0.064 Uiso calc R 1 . . H
C13A 0.2956(3) 0.45912(19) 0.52105(17) 0.0491(6) Uani d . 1 . . C
H13A 0.2945 0.5071 0.5745 0.059 Uiso calc R 1 . . H
C14A 0.3658(3) 0.38040(18) 0.51554(16) 0.0466(6) Uani d . 1 . . C
C15A 0.4250(4) 0.37611(19) 0.59072(17) 0.0517(6) Uani d . 1 . . C
H15A 0.4192 0.4235 0.6434 0.062 Uiso calc R 1 . . H
C16A 0.4928(3) 0.3026(2) 0.58910(17) 0.0508(6) Uani d . 1 . . C
H16A 0.5312 0.3003 0.6400 0.061 Uiso calc R 1 . . H
C17A 0.5022(3) 0.2331(2) 0.51089(17) 0.0511(6) Uani d . 1 . . C
C18A 0.4442(4) 0.2369(2) 0.43505(18) 0.0591(7) Uani d . 1 . . C
H18A 0.4509 0.1898 0.3824 0.071 Uiso calc R 1 . . H
C19A 0.3772(4) 0.3098(2) 0.43750(17) 0.0546(7) Uani d . 1 . . C
H19A 0.3391 0.3119 0.3864 0.066 Uiso calc R 1 . . H
C21A 0.6315(4) 0.1504(2) 0.5746(2) 0.0618(8) Uani d . 1 . . C
H21A 0.7022 0.2145 0.6154 0.074 Uiso calc R 1 . . H
H21B 0.6987 0.1061 0.5592 0.074 Uiso calc R 1 . . H
C22A 0.4991(4) 0.1144(2) 0.6174(2) 0.0594(7) Uani d . 1 . . C
C24A 0.4581(5) 0.0983(3) 0.7490(3) 0.0803(10) Uani d . 1 . . C
H24A 0.4828 0.1462 0.8086 0.096 Uiso calc R 1 . . H
H24B 0.3427 0.0849 0.7260 0.096 Uiso calc R 1 . . H
C25A 0.4900(5) 0.0087(3) 0.7436(3) 0.0835(10) Uani d . 1 . . C
H25A 0.4652 -0.0384 0.6845 0.125 Uiso calc R 1 . . H
H25B 0.4220 -0.0173 0.7756 0.125 Uiso calc R 1 . . H
H25C 0.6040 0.0226 0.7672 0.125 Uiso calc R 1 . . H
C51A 0.1082(5) 0.4729(2) 0.29759(18) 0.0723(9) Uani d . 1 . . C
H51A 0.0675 0.4937 0.2566 0.108 Uiso calc R 1 . . H
H51B 0.0359 0.4105 0.2880 0.108 Uiso calc R 1 . . H
H51C 0.2167 0.4673 0.2910 0.108 Uiso calc R 1 . . H
Br1B -0.47366(6) 1.39562(3) 0.18860(3) 0.09018(16) Uani d . 1 . . Br
O3B -0.1704(3) 0.99101(15) 0.11899(11) 0.0613(5) Uani d . 1 . . O
O20B 0.2541(3) 0.53525(15) 0.00873(13) 0.0716(6) Uani d . 1 . . O
O22B 0.5755(3) 0.6577(2) 0.07419(18) 0.0863(7) Uani d . 1 . . O
O23B 0.5702(3) 0.63849(18) 0.19614(15) 0.0763(6) Uani d . 1 . . O
N1B -0.2845(3) 0.99034(17) -0.07971(13) 0.0538(5) Uani d . 1 . . N
N2B -0.2655(3) 1.03058(15) 0.00983(12) 0.0470(5) Uani d . 1 . . N
N4B -0.1759(3) 0.90365(16) -0.02855(13) 0.0484(5) Uani d . 1 . . N
N12B -0.1129(3) 0.82677(16) -0.03591(14) 0.0523(5) Uani d . 1 . . N
C3B -0.1996(3) 0.97747(19) 0.04392(16) 0.0475(6) Uani d . 1 . . C
C5B -0.2303(4) 0.9149(2) -0.09999(16) 0.0513(6) Uani d . 1 . . C
C6B -0.3145(3) 1.11490(18) 0.05337(15) 0.0448(5) Uani d . 1 . . C
C7B -0.4037(3) 1.1475(2) 0.00535(16) 0.0506(6) Uani d . 1 . . C
H7B -0.4314 1.1129 -0.0542 0.061 Uiso calc R 1 . . H
C8B -0.4512(4) 1.2304(2) 0.04512(18) 0.0560(7) Uani d . 1 . . C
H8B -0.5101 1.2525 0.0130 0.067 Uiso calc R 1 . . H
C9B -0.4100(4) 1.2801(2) 0.13318(19) 0.0560(7) Uani d . 1 . . C
C10B -0.3234(4) 1.2490(2) 0.18235(18) 0.0587(7) Uani d . 1 . . C
H10B -0.2984 1.2832 0.2420 0.070 Uiso calc R 1 . . H
C11B -0.2743(4) 1.1661(2) 0.14178(17) 0.0556(7) Uani d . 1 . . C
H11B -0.2141 1.1449 0.1742 0.067 Uiso calc R 1 . . H
C13B -0.0544(4) 0.8231(2) 0.03228(17) 0.0531(6) Uani d . 1 . . C
H13B -0.0584 0.8697 0.0858 0.064 Uiso calc R 1 . . H
C14B 0.0191(3) 0.74554(19) 0.02632(17) 0.0498(6) Uani d . 1 . . C
C15B 0.1070(4) 0.7516(2) 0.10018(17) 0.0561(7) Uani d . 1 . . C
H15B 0.1121 0.8029 0.1528 0.067 Uiso calc R 1 . . H
C16B 0.1876(4) 0.6831(2) 0.09766(18) 0.0574(7) Uani d . 1 . . C
H16B 0.2465 0.6887 0.1480 0.069 Uiso calc R 1 . . H
C17B 0.1796(4) 0.6072(2) 0.02035(18) 0.0546(7) Uani d . 1 . . C
C18B 0.0914(4) 0.5994(2) -0.05518(18) 0.0624(8) Uani d . 1 . . C
H18B 0.0865 0.5480 -0.1077 0.075 Uiso calc R 1 . . H
C19B 0.0118(4) 0.6677(2) -0.05183(18) 0.0576(7) Uani d . 1 . . C
H19B -0.0475 0.6619 -0.1022 0.069 Uiso calc R 1 . . H
C21B 0.3468(4) 0.5392(2) 0.0827(2) 0.0665(8) Uani d . 1 . . C
H21C 0.3664 0.4763 0.0689 0.080 Uiso calc R 1 . . H
H21D 0.2832 0.5510 0.1280 0.080 Uiso calc R 1 . . H
C22B 0.5098(4) 0.6183(2) 0.1148(2) 0.0627(8) Uani d . 1 . . C
C24B 0.7354(5) 0.7077(3) 0.2362(3) 0.0825(10) Uani d . 1 . . C
H24C 0.7390 0.7470 0.2966 0.099 Uiso calc R 1 . . H
H24D 0.7603 0.7514 0.2086 0.099 Uiso calc R 1 . . H
C25B 0.8588(5) 0.6544(3) 0.2281(3) 0.0825(10) Uani d . 1 . . C
H25D 0.8305 0.6085 0.2526 0.124 Uiso calc R 1 . . H
H25E 0.9654 0.7001 0.2579 0.124 Uiso calc R 1 . . H
H25F 0.8611 0.6197 0.1683 0.124 Uiso calc R 1 . . H
C51B -0.2261(4) 0.8484(2) -0.18875(17) 0.0671(8) Uani d . 1 . . C
H51D -0.2939 0.7834 -0.2026 0.101 Uiso calc R 1 . . H
H51E -0.1148 0.8476 -0.1931 0.101 Uiso calc R 1 . . H
H51F -0.2669 0.8711 -0.2283 0.101 Uiso calc R 1 . . H
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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C17A O20A C21A 117.9(2) ?
C22A O23A C24A 118.4(3) ?
C5A N1A N2A 104.67(19) yes
C3A N2A N1A 112.46(19) yes
C3A N2A C6A 128.2(2) ?
N1A N2A C6A 119.30(18) ?
C5A N4A N12A 120.9(2) ?
C5A N4A C3A 108.56(19) yes
N12A N4A C3A 130.6(2) ?
C13A N12A N4A 119.1(2) ?
O3A C3A N2A 129.6(2) ?
O3A C3A N4A 128.0(2) ?
N2A C3A N4A 102.40(19) yes
N1A C5A N4A 111.9(2) yes
N1A C5A C51A 125.1(2) ?
N4A C5A C51A 123.0(2) ?
C11A C6A C7A 120.0(2) ?
C11A C6A N2A 121.1(2) ?
C7A C6A N2A 118.9(2) ?
C8A C7A C6A 120.2(2) ?
C8A C7A H7A 119.9 ?
C6A C7A H7A 119.9 ?
C9A C8A C7A 119.0(2) ?
C9A C8A H8A 120.5 ?
C7A C8A H8A 120.5 ?
C8A C9A C10A 122.0(2) ?
C8A C9A Br1A 119.44(19) ?
C10A C9A Br1A 118.60(19) ?
C9A C10A C11A 118.9(2) ?
C9A C10A H10A 120.5 ?
C11A C10A H10A 120.5 ?
C6A C11A C10A 120.0(2) ?
C6A C11A H11A 120.0 ?
C10A C11A H11A 120.0 ?
N12A C13A C14A 119.6(2) ?
N12A C13A H13A 120.2 ?
C14A C13A H13A 120.2 ?
C15A C14A C19A 118.5(2) ?
C15A C14A C13A 119.2(2) ?
C19A C14A C13A 122.3(2) ?
C14A C15A C16A 121.5(2) ?
C14A C15A H15A 119.3 ?
C16A C15A H15A 119.3 ?
C17A C16A C15A 119.0(2) ?
C17A C16A H16A 120.5 ?
C15A C16A H16A 120.5 ?
O20A C17A C16A 124.9(2) ?
O20A C17A C18A 114.9(2) ?
C16A C17A C18A 120.1(2) ?
C19A C18A C17A 120.4(2) ?
C19A C18A H18A 119.8 ?
C17A C18A H18A 119.8 ?
C18A C19A C14A 120.5(2) ?
C18A C19A H19A 119.7 ?
C14A C19A H19A 119.7 ?
O20A C21A C22A 112.8(2) ?
O20A C21A H21A 109.0 ?
C22A C21A H21A 109.0 ?
O20A C21A H21B 109.0 ?
C22A C21A H21B 109.0 ?
H21A C21A H21B 107.8 ?
O22A C22A O23A 125.2(3) ?
O22A C22A C21A 124.9(3) ?
O23A C22A C21A 109.9(3) ?
C25A C24A O23A 108.8(3) ?
C25A C24A H24A 109.9 ?
O23A C24A H24A 109.9 ?
C25A C24A H24B 109.9 ?
O23A C24A H24B 109.9 ?
H24A C24A H24B 108.3 ?
C24A C25A H25A 109.5 ?
C24A C25A H25B 109.5 ?
H25A C25A H25B 109.5 ?
C24A C25A H25C 109.5 ?
H25A C25A H25C 109.5 ?
H25B C25A H25C 109.5 ?
C5A C51A H51A 109.5 ?
C5A C51A H51B 109.5 ?
H51A C51A H51B 109.5 ?
C5A C51A H51C 109.5 ?
H51A C51A H51C 109.5 ?
H51B C51A H51C 109.5 ?
C17B O20B C21B 117.5(2) ?
C22B O23B C24B 118.1(3) ?
C5B N1B N2B 105.1(2) yes
C3B N2B N1B 111.83(19) yes
C3B N2B C6B 128.4(2) ?
N1B N2B C6B 119.7(2) ?
C5B N4B N12B 121.1(2) ?
C5B N4B C3B 108.7(2) yes
N12B N4B C3B 130.3(2) ?
C13B N12B N4B 118.7(2) ?
O3B C3B N2B 128.8(2) ?
O3B C3B N4B 128.4(2) ?
N2B C3B N4B 102.8(2) yes
N1B C5B N4B 111.6(2) yes
N1B C5B C51B 124.8(2) ?
N4B C5B C51B 123.6(2) ?
C11B C6B C7B 119.6(2) ?
C11B C6B N2B 121.6(2) ?
C7B C6B N2B 118.8(2) ?
C8B C7B C6B 120.7(2) ?
C8B C7B H7B 119.7 ?
C6B C7B H7B 119.7 ?
C9B C8B C7B 118.7(2) ?
C9B C8B H8B 120.7 ?
C7B C8B H8B 120.7 ?
C8B C9B C10B 121.9(2) ?
C8B C9B Br1B 118.9(2) ?
C10B C9B Br1B 119.2(2) ?
C9B C10B C11B 119.1(2) ?
C9B C10B H10B 120.5 ?
C11B C10B H10B 120.5 ?
C6B C11B C10B 120.0(2) ?
C6B C11B H11B 120.0 ?
C10B C11B H11B 120.0 ?
N12B C13B C14B 119.7(2) ?
N12B C13B H13B 120.1 ?
C14B C13B H13B 120.1 ?
C15B C14B C19B 118.3(2) ?
C15B C14B C13B 119.1(2) ?
C19B C14B C13B 122.5(2) ?
C14B C15B C16B 121.6(2) ?
C14B C15B H15B 119.2 ?
C16B C15B H15B 119.2 ?
C17B C16B C15B 119.4(3) ?
C17B C16B H16B 120.3 ?
C15B C16B H16B 120.3 ?
C16B C17B O20B 125.4(3) ?
C16B C17B C18B 120.1(2) ?
O20B C17B C18B 114.6(2) ?
C19B C18B C17B 120.0(2) ?
C19B C18B H18B 120.0 ?
C17B C18B H18B 120.0 ?
C18B C19B C14B 120.6(3) ?
C18B C19B H19B 119.7 ?
C14B C19B H19B 119.7 ?
O20B C21B C22B 112.4(3) ?
O20B C21B H21C 109.1 ?
C22B C21B H21C 109.1 ?
O20B C21B H21D 109.1 ?
C22B C21B H21D 109.1 ?
H21C C21B H21D 107.9 ?
O22B C22B O23B 124.7(3) ?
O22B C22B C21B 125.3(3) ?
O23B C22B C21B 110.0(3) ?
O23B C24B C25B 110.2(3) ?
O23B C24B H24C 109.6 ?
C25B C24B H24C 109.6 ?
O23B C24B H24D 109.6 ?
C25B C24B H24D 109.6 ?
H24C C24B H24D 108.1 ?
C24B C25B H25D 109.5 ?
C24B C25B H25E 109.5 ?
H25D C25B H25E 109.5 ?
C24B C25B H25F 109.5 ?
H25D C25B H25F 109.5 ?
H25E C25B H25F 109.5 ?
C5B C51B H51D 109.5 ?
C5B C51B H51E 109.5 ?
H51D C51B H51E 109.5 ?
C5B C51B H51F 109.5 ?
H51D C51B H51F 109.5 ?
H51E C51B H51F 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
Br1A C9A . 1.903(2) ?
O3A C3A . 1.218(3) ?
O20A C17A . 1.372(3) ?
O20A C21A . 1.411(3) ?
O22A C22A . 1.183(4) ?
O23A C22A . 1.336(4) ?
O23A C24A . 1.488(4) ?
N1A C5A . 1.289(3) yes
N1A N2A . 1.394(3) yes
N2A C3A . 1.370(3) yes
N2A C6A . 1.420(3) ?
N4A C5A . 1.370(3) yes
N4A N12A . 1.389(3) ?
N4A C3A . 1.394(3) yes
N12A C13A . 1.267(3) ?
C5A C51A . 1.488(4) ?
C6A C11A . 1.381(3) ?
C6A C7A . 1.388(3) ?
C7A C8A . 1.378(3) ?
C7A H7A . 0.9300 ?
C8A C9A . 1.370(4) ?
C8A H8A . 0.9300 ?
C9A C10A . 1.374(4) ?
C10A C11A . 1.387(3) ?
C10A H10A . 0.9300 ?
C11A H11A . 0.9300 ?
C13A C14A . 1.460(3) ?
C13A H13A . 0.9300 ?
C14A C15A . 1.387(4) ?
C14A C19A . 1.388(4) ?
C15A C16A . 1.391(3) ?
C15A H15A . 0.9300 ?
C16A C17A . 1.377(4) ?
C16A H16A . 0.9300 ?
C17A C18A . 1.390(4) ?
C18A C19A . 1.374(4) ?
C18A H18A . 0.9300 ?
C19A H19A . 0.9300 ?
C21A C22A . 1.514(4) ?
C21A H21A . 0.9700 ?
C21A H21B . 0.9700 ?
C24A C25A . 1.451(5) ?
C24A H24A . 0.9700 ?
C24A H24B . 0.9700 ?
C25A H25A . 0.9600 ?
C25A H25B . 0.9600 ?
C25A H25C . 0.9600 ?
C51A H51A . 0.9600 ?
C51A H51B . 0.9600 ?
C51A H51C . 0.9600 ?
Br1B C9B . 1.903(3) ?
O3B C3B . 1.222(3) ?
O20B C17B . 1.370(3) ?
O20B C21B . 1.418(4) ?
O22B C22B . 1.193(4) ?
O23B C22B . 1.339(4) ?
O23B C24B . 1.466(4) ?
N1B C5B . 1.293(3) yes
N1B N2B . 1.397(3) yes
N2B C3B . 1.378(3) yes
N2B C6B . 1.410(3) ?
N4B C5B . 1.373(3) yes
N4B N12B . 1.389(3) ?
N4B C3B . 1.391(3) yes
N12B C13B . 1.269(3) ?
C5B C51B . 1.479(4) ?
C6B C11B . 1.379(4) ?
C6B C7B . 1.392(3) ?
C7B C8B . 1.374(4) ?
C7B H7B . 0.9300 ?
C8B C9B . 1.372(4) ?
C8B H8B . 0.9300 ?
C9B C10B . 1.376(4) ?
C10B C11B . 1.384(4) ?
C10B H10B . 0.9300 ?
C11B H11B . 0.9300 ?
C13B C14B . 1.460(4) ?
C13B H13B . 0.9300 ?
C14B C15B . 1.383(4) ?
C14B C19B . 1.394(4) ?
C15B C16B . 1.388(4) ?
C15B H15B . 0.9300 ?
C16B C17B . 1.369(4) ?
C16B H16B . 0.9300 ?
C17B C18B . 1.398(4) ?
C18B C19B . 1.376(4) ?
C18B H18B . 0.9300 ?
C19B H19B . 0.9300 ?
C21B C22B . 1.507(5) ?
C21B H21C . 0.9700 ?
C21B H21D . 0.9700 ?
C24B C25B . 1.469(5) ?
C24B H24C . 0.9700 ?
C24B H24D . 0.9700 ?
C25B H25D . 0.9600 ?
C25B H25E . 0.9600 ?
C25B H25F . 0.9600 ?
C51B H51D . 0.9600 ?
C51B H51E . 0.9600 ?
C51B H51F . 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
C8B H8B O22B 2_575 0.93 2.54 3.430(4) 161 yes
C10A H10A O3B 2_576 0.93 2.45 3.371(3) 172 yes
C10B H10B O3A 2_576 0.93 2.39 3.314(3) 171 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
C5A N1A N2A C3A -0.6(3)
C5A N1A N2A C6A -179.9(2)
C5A N4A N12A C13A 176.9(3)
C3A N4A N12A C13A -1.6(4)
N1A N2A C3A O3A -178.2(3)
C6A N2A C3A O3A 1.0(5)
N1A N2A C3A N4A 1.3(3)
C6A N2A C3A N4A -179.5(2)
C5A N4A C3A O3A 178.0(3)
N12A N4A C3A O3A -3.3(5)
C5A N4A C3A N2A -1.4(3)
N12A N4A C3A N2A 177.2(3)
N2A N1A C5A N4A -0.3(3)
N2A N1A C5A C51A 179.4(3)
N12A N4A C5A N1A -177.6(2)
C3A N4A C5A N1A 1.2(3)
N12A N4A C5A C51A 2.6(4)
C3A N4A C5A C51A -178.6(3)
C3A N2A C6A C11A 4.5(4)
N1A N2A C6A C11A -176.3(3)
C3A N2A C6A C7A -175.8(3)
N1A N2A C6A C7A 3.3(4)
C11A C6A C7A C8A -0.3(4)
N2A C6A C7A C8A -179.9(3)
C6A C7A C8A C9A 0.5(4)
C7A C8A C9A C10A -0.2(4)
C7A C8A C9A Br1A -179.5(2)
C8A C9A C10A C11A -0.2(4)
Br1A C9A C10A C11A 179.1(2)
C7A C6A C11A C10A -0.1(4)
N2A C6A C11A C10A 179.5(3)
C9A C10A C11A C6A 0.3(5)
N4A N12A C13A C14A -178.3(2)
N12A C13A C14A C15A -177.6(3)
N12A C13A C14A C19A 3.0(4)
C19A C14A C15A C16A -0.7(4)
C13A C14A C15A C16A 179.9(3)
C14A C15A C16A C17A 0.5(4)
C21A O20A C17A C16A -1.7(4)
C21A O20A C17A C18A 178.3(3)
C15A C16A C17A O20A 179.9(3)
C15A C16A C17A C18A -0.1(4)
O20A C17A C18A C19A 180.0(3)
C16A C17A C18A C19A 0.0(5)
C17A C18A C19A C14A -0.2(5)
C15A C14A C19A C18A 0.6(4)
C13A C14A C19A C18A 180.0(3)
C17A O20A C21A C22A 74.5(3)
C24A O23A C22A O22A 7.5(4)
C24A O23A C22A C21A -173.0(2)
O20A C21A C22A O22A 18.3(4)
O20A C21A C22A O23A -161.3(2)
C22A O23A C24A C25A 95.2(4)
C5B N1B N2B C3B -0.5(3)
C5B N1B N2B C6B -179.6(2)
C5B N4B N12B C13B 175.5(3)
C3B N4B N12B C13B -6.0(4)
N1B N2B C3B O3B -178.4(3)
C6B N2B C3B O3B 0.7(5)
N1B N2B C3B N4B 1.1(3)
C6B N2B C3B N4B -179.9(2)
C5B N4B C3B O3B 178.2(3)
N12B N4B C3B O3B -0.4(5)
C5B N4B C3B N2B -1.2(3)
N12B N4B C3B N2B -179.9(2)
N2B N1B C5B N4B -0.3(3)
N2B N1B C5B C51B 179.9(3)
N12B N4B C5B N1B 179.8(2)
C3B N4B C5B N1B 1.0(3)
N12B N4B C5B C51B -0.4(4)
C3B N4B C5B C51B -179.2(3)
C3B N2B C6B C11B 11.6(4)
N1B N2B C6B C11B -169.4(3)
C3B N2B C6B C7B -169.3(3)
N1B N2B C6B C7B 9.7(4)
C11B C6B C7B C8B 0.4(4)
N2B C6B C7B C8B -178.8(3)
C6B C7B C8B C9B -0.5(4)
C7B C8B C9B C10B -0.2(5)
C7B C8B C9B Br1B 179.5(2)
C8B C9B C10B C11B 1.0(5)
Br1B C9B C10B C11B -178.7(2)
C7B C6B C11B C10B 0.4(4)
N2B C6B C11B C10B 179.5(3)
C9B C10B C11B C6B -1.1(5)
N4B N12B C13B C14B -177.3(2)
N12B C13B C14B C15B 169.1(3)
N12B C13B C14B C19B -7.5(4)
C19B C14B C15B C16B 0.5(5)
C13B C14B C15B C16B -176.2(3)
C14B C15B C16B C17B -0.3(5)
C15B C16B C17B O20B 179.6(3)
C15B C16B C17B C18B 0.2(5)
C21B O20B C17B C16B 0.2(5)
C21B O20B C17B C18B 179.5(3)
C16B C17B C18B C19B -0.3(5)
O20B C17B C18B C19B -179.7(3)
C17B C18B C19B C14B 0.5(5)
C15B C14B C19B C18B -0.6(5)
C13B C14B C19B C18B 176.0(3)
C17B O20B C21B C22B -74.6(3)
C24B O23B C22B O22B -5.6(4)
C24B O23B C22B C21B 174.7(3)
O20B C21B C22B O22B -17.6(4)
O20B C21B C22B O23B 162.1(2)
C22B O23B C24B C25B -95.4(4)
N4A N12A C13A H13A 1.7
N4B N12B C13B H13B 2.7
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24732295
