#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:46:13 +0300 (Mon, 04 May 2020) $
#$Revision: 251478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038245.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_4038245
loop_
_publ_author_name
'Matsubara, Ryosuke'
'Ando, Akihiro'
'Hasebe, Hayu'
'Kim, Hojin'
'Tsuneda, Takao'
'Hayashi, Masahiko'
_publ_section_title
;
 Synthesis and Synthetic Application of Chloro- and Bromofuroxans.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5959
_journal_page_last               5972
_journal_paper_doi               10.1021/acs.joc.0c00326
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C12 H15 Br N2 O2'
_chemical_formula_sum            'C12 H15 Br N2 O2'
_chemical_formula_weight         299.17
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.2121
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.2209
_cell_length_b                   6.6668
_cell_length_c                   9.3831
_cell_measurement_reflns_used    2653
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.7025
_cell_measurement_theta_min      2.8775
_cell_volume                     569.376
_computing_cell_refinement       Unknown
_computing_data_collection       Unknown
_computing_data_reduction        Unknown
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2833
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.611
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            NONE
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NONE
_exptl_crystal_F_000             304.00
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.260
_refine_ls_extinction_coef       0.0020(17)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1137
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0178
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0218P)²+0.3543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0465
_reflns_number_gt                1104
_reflns_number_total             1137
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo0c00326_si_010.cif
_cod_data_source_block           AA1046_PTLCa_0am
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038245--4038253.cif.
;
_cod_original_cell_volume        569.3762
_cod_database_code               4038245
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
3 -X,-Y,-Z
4 +X,1/2-Y,+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
Br1 Br 0.66940(2) 0.2500 0.61975(2) 0.01357(11) Uani 1.0 2 d . . .
O2 O 0.33419(18) 0.2500 0.30708(18) 0.0154(4) Uani 1.0 2 d . . .
O3 O 0.11560(19) 0.2500 0.38937(19) 0.0183(4) Uani 1.0 2 d . . .
N4 N 0.2494(2) 0.2500 0.4246(2) 0.0128(4) Uani 1.0 2 d . . .
N5 N 0.4804(2) 0.2500 0.3671(2) 0.0147(5) Uani 1.0 2 d . . .
C6 C 0.2834(2) 0.2500 0.6909(2) 0.0105(5) Uani 1.0 2 d . . .
C7 C 0.4834(3) 0.2500 0.5063(3) 0.0117(5) Uani 1.0 2 d . . .
C8 C 0.3422(3) 0.2500 0.5495(2) 0.0113(5) Uani 1.0 2 d . . .
C9 C 0.3429(3) 0.2500 0.9627(3) 0.0134(5) Uani 1.0 2 d . . .
C10 C 0.12428(18) 0.0621(3) 0.83982(18) 0.0153(4) Uani 1.0 4 d . . .
C11 C 0.4079(3) 0.2500 0.8216(3) 0.0128(5) Uani 1.0 2 d . . .
C12 C 0.0299(3) 0.2500 0.8442(3) 0.0180(6) Uani 1.0 2 d . . .
C13 C 0.24842(19) 0.0626(3) 0.96909(18) 0.0149(4) Uani 1.0 4 d . . .
C14 C 0.18899(18) 0.0601(3) 0.69881(17) 0.0135(4) Uani 1.0 4 d . . .
H15 H -0.047(4) 0.2500 0.763(4) 0.023(8) Uiso 1.0 2 d . . .
H16 H -0.010(4) 0.2500 0.931(4) 0.022(8) Uiso 1.0 2 d . . .
H17 H 0.109(3) 0.055(3) 0.615(2) 0.017(5) Uiso 1.0 4 d . . .
H18 H 0.250(2) -0.055(3) 0.697(2) 0.010(5) Uiso 1.0 4 d . . .
H19 H 0.465(2) 0.136(3) 0.818(2) 0.015(5) Uiso 1.0 4 d . . .
H20 H 0.424(3) 0.2500 1.039(3) 0.011(7) Uiso 1.0 2 d . . .
H21 H 0.306(3) -0.056(3) 0.966(2) 0.014(5) Uiso 1.0 4 d . . .
H22 H 0.208(3) 0.062(3) 1.059(3) 0.017(5) Uiso 1.0 4 d . . .
H23 H 0.069(3) -0.051(3) 0.843(2) 0.015(5) Uiso 1.0 4 d . . .
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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N4 O2 N5 107.52(15) yes . . .
O2 N4 O3 115.92(17) yes . . .
O2 N4 C8 108.63(18) yes . . .
O3 N4 C8 135.5(3) yes . . .
O2 N5 C7 105.8(2) yes . . .
C8 C6 C11 111.88(19) yes . . .
C8 C6 C14 109.04(11) yes . . .
C8 C6 C14 109.04(11) yes . . 4_555
C11 C6 C14 108.41(12) yes . . .
C11 C6 C14 108.41(12) yes . . 4_555
C14 C6 C14 110.06(15) yes . . 4_555
Br1 C7 N5 116.2(2) yes . . .
Br1 C7 C8 129.5(2) yes . . .
N5 C7 C8 114.3(3) yes . . .
N4 C8 C6 120.0(3) yes . . .
N4 C8 C7 103.7(2) yes . . .
C6 C8 C7 136.3(2) yes . . .
C11 C9 C13 109.66(15) yes . . .
C11 C9 C13 109.66(15) yes . . 4_555
C13 C9 C13 109.5(2) yes . . 4_555
C12 C10 C13 109.51(16) yes . . .
C12 C10 C14 109.35(16) yes . . .
C13 C10 C14 109.80(14) yes . . .
C6 C11 C9 110.0(3) yes . . .
C10 C12 C10 110.0(2) yes . . 4_555
C9 C13 C10 109.23(16) yes . . .
C6 C14 C10 109.51(14) yes . . .
C11 C9 H20 106.2(19) no . . .
C13 C9 H20 110.9(9) no . . .
C13 C9 H20 110.9(9) no 4_555 . .
C12 C10 H23 110.6(13) no . . .
C13 C10 H23 109.0(12) no . . .
C14 C10 H23 108.6(13) no . . .
C6 C11 H19 109.0(12) no . . .
C6 C11 H19 109.0(12) no . . 4_555
C9 C11 H19 109.5(13) no . . .
C9 C11 H19 109.5(13) no . . 4_555
H19 C11 H19 109.8(17) no . . 4_555
C10 C12 H15 109.4(11) no . . .
C10 C12 H16 108.9(9) no . . .
C10 C12 H15 109.4(11) no 4_555 . .
C10 C12 H16 108.9(9) no 4_555 . .
H15 C12 H16 110(3) no . . .
C9 C13 H21 110.5(13) no . . .
C9 C13 H22 109.8(12) no . . .
C10 C13 H21 108.7(11) no . . .
C10 C13 H22 110.0(11) no . . .
H21 C13 H22 108.5(17) no . . .
C6 C14 H17 110.3(12) no . . .
C6 C14 H18 109.0(12) no . . .
C10 C14 H17 110.1(13) no . . .
C10 C14 H18 109.2(12) no . . .
H17 C14 H18 108.8(16) no . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C7 1.868(3) yes . .
O2 N4 1.450(3) yes . .
O2 N5 1.375(3) yes . .
O3 N4 1.225(3) yes . .
N4 C8 1.336(3) yes . .
N5 C7 1.302(4) yes . .
C6 C8 1.511(3) yes . .
C6 C11 1.540(3) yes . .
C6 C14 1.545(2) yes . .
C6 C14 1.545(2) yes . 4_555
C7 C8 1.424(4) yes . .
C9 C11 1.538(5) yes . .
C9 C13 1.530(3) yes . .
C9 C13 1.530(3) yes . 4_555
C10 C12 1.530(3) yes . .
C10 C13 1.529(3) yes . .
C10 C14 1.536(3) yes . .
C9 H20 0.95(3) no . .
C10 H23 0.91(2) no . .
C11 H19 0.93(2) no . .
C11 H19 0.93(2) no . 4_555
C12 H15 0.96(3) no . .
C12 H16 0.95(4) no . .
C13 H21 0.96(2) no . .
C13 H22 0.98(3) no . .
C14 H17 0.990(19) no . .
C14 H18 0.95(2) no . .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Br1 C11 3.296(3) no . .
O3 N5 3.403(3) no . .
O3 C6 3.000(3) no . .
O3 C7 3.393(4) no . .
O3 C14 3.140(3) no . .
O3 C14 3.140(3) no . 4_555
N4 C14 2.999(3) no . .
N4 C14 2.999(3) no . 4_555
C6 C10 2.516(3) no . 4_555
C6 C12 2.934(4) no . .
C6 C13 2.958(3) no . .
C6 C13 2.958(3) no . 4_555
C7 C11 3.146(5) no . .
C9 C10 2.494(3) no . 4_555
C9 C12 2.922(4) no . .
C9 C14 2.936(3) no . .
C9 C14 2.936(3) no . 4_555
C10 C11 2.929(3) no . .
C10 C13 2.932(3) no . 4_555
C10 C14 2.950(3) no . 4_555
C11 C12 3.526(4) no . .
C12 C13 2.498(3) no . 4_555
C12 C14 2.501(4) no . 4_555
C13 C14 3.552(3) no . 4_555
Br1 O2 3.4046(4) no . 2_646
Br1 O2 3.4046(4) no . 2_656
Br1 N4 3.4562(6) no . 2_646
Br1 N4 3.4562(6) no . 2_656
O2 Br1 3.4046(4) no . 2_646
O2 Br1 3.4046(4) no . 2_656
O2 C9 3.245(4) no . 1_554
O2 C13 3.383(3) no . 1_554
O2 C13 3.383(3) no . 4_554
O3 C10 3.510(2) no . 2_556
O3 C10 3.510(2) no . 3_556
O3 C14 3.479(3) no . 2_556
O3 C14 3.479(3) no . 3_556
N4 Br1 3.4562(6) no . 2_646
N4 Br1 3.4562(6) no . 2_656
N5 C7 3.5365(11) no . 2_646
N5 C7 3.5365(11) no . 2_656
C7 N5 3.5365(11) no . 2_646
C7 N5 3.5365(11) no . 2_656
C7 C7 3.3512(5) no . 2_646
C7 C7 3.3512(5) no . 2_656
C9 O2 3.245(4) no . 1_556
C10 O3 3.510(2) no . 2_546
C13 O2 3.383(3) no . 1_556
C14 O3 3.479(3) no . 2_546
Br1 H19 2.95(2) no . .
Br1 H19 2.95(2) no . 4_555
O3 H17 2.49(2) no . .
O3 H17 2.49(2) no . 4_555
O3 H18 3.589(18) no . .
O3 H18 3.589(18) no . 4_555
N4 H17 2.70(3) no . .
N4 H17 2.70(3) no . 4_555
N4 H18 3.271(19) no . .
N4 H18 3.271(19) no . 4_555
C6 H15 3.23(4) no . .
C6 H17 2.10(2) no . 4_555
C6 H18 2.06(2) no . 4_555
C6 H20 3.32(3) no . .
C6 H21 3.27(2) no . .
C6 H21 3.27(2) no . 4_555
C6 H23 3.30(2) no . .
C6 H23 3.30(2) no . 4_555
C7 H19 3.05(2) no . .
C7 H19 3.05(2) no . 4_555
C8 H17 2.67(3) no . .
C8 H17 2.67(3) no . 4_555
C8 H18 2.68(2) no . .
C8 H18 2.68(2) no . 4_555
C8 H19 2.701(19) no . .
C8 H19 2.701(19) no . 4_555
C9 H16 3.22(3) no . .
C9 H18 3.225(19) no . .
C9 H18 3.225(19) no . 4_555
C9 H21 2.07(2) no . 4_555
C9 H22 2.08(3) no . 4_555
C9 H23 3.28(2) no . .
C9 H23 3.28(2) no . 4_555
C10 H17 3.30(2) no . 4_555
C10 H19 3.22(2) no . .
C10 H20 3.33(3) no . .
C10 H22 3.26(2) no . 4_555
C10 H23 3.30(2) no . 4_555
C11 H17 3.368(19) no . .
C11 H17 3.368(19) no . 4_555
C11 H18 2.663(19) no . .
C11 H18 2.663(19) no . 4_555
C11 H21 2.70(2) no . .
C11 H21 2.70(2) no . 4_555
C11 H22 3.36(3) no . .
C11 H22 3.36(3) no . 4_555
C12 H17 2.71(2) no . .
C12 H17 2.71(2) no . 4_555
C12 H18 3.32(2) no . .
C12 H18 3.32(2) no . 4_555
C12 H21 3.32(2) no . .
C12 H21 3.32(2) no . 4_555
C12 H22 2.70(2) no . .
C12 H22 2.70(2) no . 4_555
C12 H23 2.04(2) no . 4_555
C13 H15 3.33(3) no . .
C13 H16 2.66(3) no . .
C13 H17 3.367(19) no . .
C13 H18 2.670(19) no . .
C13 H19 2.68(2) no . .
C13 H19 3.31(2) no . 4_555
C13 H21 3.34(2) no . 4_555
C13 H22 2.69(2) no . 4_555
C14 H15 2.67(3) no . .
C14 H16 3.32(4) no . .
C14 H17 2.75(2) no . 4_555
C14 H18 3.35(2) no . 4_555
C14 H19 2.661(18) no . .
C14 H19 3.308(19) no . 4_555
C14 H21 2.678(19) no . .
C14 H22 3.36(3) no . .
H15 H17 2.52(4) no . .
H15 H17 2.52(4) no . 4_555
H15 H18 3.54(4) no . .
H15 H18 3.54(4) no . 4_555
H15 H22 3.57(4) no . .
H15 H22 3.57(4) no . 4_555
H15 H23 2.34(3) no . .
H15 H23 2.34(3) no . 4_555
H16 H17 3.57(4) no . .
H16 H17 3.57(4) no . 4_555
H16 H21 3.53(4) no . .
H16 H21 3.53(4) no . 4_555
H16 H22 2.50(3) no . .
H16 H22 2.50(3) no . 4_555
H16 H23 2.33(3) no . .
H16 H23 2.33(3) no . 4_555
H17 H17 2.61(3) no . 4_555
H17 H19 3.57(3) no . .
H17 H21 3.57(3) no . .
H17 H23 2.34(3) no . .
H18 H19 2.48(3) no . .
H18 H19 3.51(3) no . 4_555
H18 H21 2.49(3) no . .
H18 H22 3.56(3) no . .
H18 H23 2.32(3) no . .
H19 H20 2.30(4) no . .
H19 H21 2.52(3) no . .
H19 H21 3.55(3) no . 4_555
H19 H22 3.57(3) no . .
H20 H21 2.36(3) no . .
H20 H21 2.36(3) no . 4_555
H20 H22 2.39(4) no . .
H20 H22 2.39(4) no . 4_555
H21 H22 3.57(3) no . 4_555
H21 H23 2.30(3) no . .
H22 H22 2.51(3) no . 4_555
H22 H23 2.34(3) no . .
Br1 H15 2.74(3) no . 1_655
Br1 H18 3.44(2) no . 2_656
Br1 H18 3.44(2) no . 3_656
O2 H19 3.48(2) no . 2_656
O2 H19 3.48(2) no . 3_656
O2 H20 2.77(3) no . 1_554
O2 H22 2.74(2) no . 1_554
O2 H22 2.74(2) no . 4_554
O3 H17 2.90(2) no . 2_556
O3 H17 2.90(2) no . 3_556
O3 H18 3.578(19) no . 2_556
O3 H18 3.578(19) no . 3_556
O3 H22 3.57(3) no . 1_554
O3 H22 3.57(3) no . 4_554
O3 H23 2.868(19) no . 2_556
O3 H23 2.868(19) no . 3_556
N5 H18 2.95(2) no . 2_656
N5 H18 2.95(2) no . 3_656
N5 H19 3.19(2) no . 2_656
N5 H19 3.19(2) no . 3_656
N5 H20 3.04(3) no . 1_554
C7 H18 3.59(2) no . 2_656
C7 H18 3.59(2) no . 3_656
C9 H19 3.579(19) no . 2_657
C9 H19 3.579(19) no . 3_657
C9 H21 3.45(2) no . 2_657
C9 H21 3.45(2) no . 3_657
C10 H16 3.28(3) no . 2_547
C10 H22 3.45(2) no . 3_557
C10 H23 3.45(2) no . 4_545
C11 H21 3.303(19) no . 2_657
C11 H21 3.303(19) no . 3_657
C12 H22 3.25(2) no . 2_557
C12 H22 3.25(2) no . 3_557
C12 H23 3.47(2) no . 2_557
C12 H23 3.47(2) no . 3_557
C13 H16 3.27(3) no . 2_547
C13 H19 3.320(18) no . 3_657
C13 H21 3.42(2) no . 4_545
C14 H18 3.41(2) no . 4_545
H15 Br1 2.74(3) no . 1_455
H15 H22 3.18(4) no . 2_557
H15 H22 3.18(4) no . 3_557
H16 C10 3.28(3) no . 2_557
H16 C10 3.28(3) no . 3_557
H16 C13 3.27(3) no . 2_557
H16 C13 3.27(3) no . 3_557
H16 H16 3.570(17) no . 2_547
H16 H16 3.570(17) no . 2_557
H16 H21 3.30(4) no . 2_557
H16 H21 3.30(4) no . 3_557
H16 H22 2.78(3) no . 2_557
H16 H22 2.78(3) no . 3_557
H16 H23 2.63(4) no . 2_557
H16 H23 2.63(4) no . 3_557
H17 O3 2.90(2) no . 2_546
H17 H17 2.80(3) no . 3_556
H18 Br1 3.44(2) no . 2_646
H18 O3 3.578(19) no . 2_546
H18 N5 2.95(2) no . 2_646
H18 C7 3.59(2) no . 2_646
H18 C14 3.41(2) no . 4_545
H18 H18 2.59(3) no . 4_545
H18 H21 3.59(3) no . 4_545
H18 H23 3.50(3) no . 4_545
H19 O2 3.48(2) no . 2_646
H19 N5 3.19(2) no . 2_646
H19 C9 3.579(19) no . 2_647
H19 C13 3.320(18) no . 3_657
H19 H20 3.00(3) no . 2_647
H19 H21 3.38(3) no . 2_657
H19 H21 2.73(3) no . 3_657
H19 H22 3.32(3) no . 3_657
H20 O2 2.77(3) no . 1_556
H20 N5 3.04(3) no . 1_556
H20 H19 3.00(3) no . 2_657
H20 H19 3.00(3) no . 3_657
H20 H21 2.81(4) no . 2_657
H20 H21 2.81(4) no . 3_657
H21 C9 3.45(2) no . 2_647
H21 C11 3.303(19) no . 2_647
H21 C13 3.42(2) no . 4_545
H21 H16 3.30(4) no . 2_547
H21 H18 3.59(3) no . 4_545
H21 H19 3.38(3) no . 2_647
H21 H19 2.73(3) no . 3_657
H21 H20 2.81(4) no . 2_647
H21 H21 2.58(3) no . 4_545
H21 H23 3.49(3) no . 4_545
H22 O2 2.74(2) no . 1_556
H22 O3 3.57(3) no . 1_556
H22 C10 3.45(2) no . 3_557
H22 C12 3.25(2) no . 2_547
H22 H15 3.18(4) no . 2_547
H22 H16 2.78(3) no . 2_547
H22 H19 3.32(3) no . 3_657
H22 H23 2.85(3) no . 3_557
H23 O3 2.868(19) no . 2_546
H23 C10 3.45(2) no . 4_545
H23 C12 3.47(2) no . 2_547
H23 H16 2.63(4) no . 2_547
H23 H18 3.50(3) no . 4_545
H23 H21 3.49(3) no . 4_545
H23 H22 2.85(3) no . 3_557
H23 H23 3.46(3) no . 3_557
H23 H23 2.65(3) no . 4_545
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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N4 O2 N5 C7 0.0 no . . . .
N5 O2 N4 O3 180.0 no . . . .
N5 O2 N4 C8 0.0 no . . . .
O2 N4 C8 C6 180.0 no . . . .
O2 N4 C8 C7 0.0 no . . . .
O3 N4 C8 C6 0.0 no . . . .
O3 N4 C8 C7 180.0 no . . . .
O2 N5 C7 Br1 180.0 no . . . .
O2 N5 C7 C8 0.0 no . . . .
C8 C6 C11 C9 180.0 no . . . .
C11 C6 C8 N4 180.0 no . . . .
C11 C6 C8 C7 0.0 no . . . .
C8 C6 C14 C10 -178.08(13) no . . . .
C14 C6 C8 N4 60.10(11) no . . . .
C14 C6 C8 C7 -119.90(11) no . . . .
C8 C6 C14 C10 178.08(13) no . . 4_555 4_555
C14 C6 C8 N4 -60.10(11) no 4_555 . . .
C14 C6 C8 C7 119.90(11) no 4_555 . . .
C11 C6 C14 C10 59.90(17) no . . . .
C14 C6 C11 C9 -59.72(12) no . . . .
C11 C6 C14 C10 -59.90(17) no . . 4_555 4_555
C14 C6 C11 C9 59.72(12) no 4_555 . . .
C14 C6 C14 C10 58.51(16) no . . 4_555 4_555
C14 C6 C14 C10 -58.51(16) no 4_555 . . .
Br1 C7 C8 N4 180.0 no . . . .
Br1 C7 C8 C6 0.0 no . . . .
N5 C7 C8 N4 0.0 no . . . .
N5 C7 C8 C6 180.0 no . . . .
C11 C9 C13 C10 -59.7(2) no . . . .
C13 C9 C11 C6 60.15(14) no . . . .
C11 C9 C13 C10 59.7(2) no . . 4_555 4_555
C13 C9 C11 C6 -60.15(14) no 4_555 . . .
C13 C9 C13 C10 -60.7(3) no . . 4_555 4_555
C13 C9 C13 C10 60.7(3) no 4_555 . . .
C12 C10 C13 C9 -59.79(19) no . . . .
C13 C10 C12 C10 59.4(3) no . . . 4_555
C12 C10 C14 C6 59.38(16) no . . . .
C14 C10 C12 C10 -61.0(2) no . . . 4_555
C13 C10 C14 C6 -60.79(16) no . . . .
C14 C10 C13 C9 60.28(17) no . . . .
