#------------------------------------------------------------------------------
#$Date: 2022-01-06 22:58:03 +0100 (Thu 06 de Jan de 2022) $
#$Revision: 271874 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/84/7158431.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_7158431
loop_
_publ_author_name
'Li, Yi-Na'
'Li, Xue-Lin'
'Wu, Jin-Bo'
'Jiang, Hong'
'Liu, Yunmei'
'Guo, Yu'
'Zeng, Yao-Fu'
'Wang, Zhen'
_publ_section_title
;
 Metal-free regioselective nitration of quinoxalin-2(1H)-ones with
 tert-butyl nitrite.
;
_journal_issue                   48
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              10554
_journal_page_last               10559
_journal_paper_doi               10.1039/d1ob02015c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C17 H14 Br N3 O3'
_chemical_formula_sum            'C17 H14 Br N3 O3'
_chemical_formula_weight         388.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.210(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.4559(18)
_cell_length_b                   8.8913(8)
_cell_length_c                   17.8312(16)
_cell_measurement_reflns_used    3092
_cell_measurement_temperature    292.99(10)
_cell_measurement_theta_max      22.9070
_cell_measurement_theta_min      2.3160
_cell_volume                     3324.7(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  44.00   1.00    7.00    --   11.90 -77.00 -30.00  108
  2  ω    -15.00  12.00   1.00    7.00    --  -11.35 -99.00-120.00   27
  3  ω     36.00  84.00   1.00    7.00    --   11.90-178.00 -30.00   48
  4  ω    -74.00 -18.00   1.00    7.00    --  -11.35 -77.00 150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0042596000
_diffrn_orient_matrix_UB_12      0.0469510000
_diffrn_orient_matrix_UB_13      0.0328529000
_diffrn_orient_matrix_UB_21      0.0328315000
_diffrn_orient_matrix_UB_22      0.0072865000
_diffrn_orient_matrix_UB_23      -0.0004281000
_diffrn_orient_matrix_UB_31      -0.0068496000
_diffrn_orient_matrix_UB_32      0.0640880000
_diffrn_orient_matrix_UB_33      -0.0240306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17453
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.493
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00144(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         5861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0335P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3141
_reflns_number_total             5861
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02015c2.cif
_cod_data_source_block           lyn-g
_cod_depositor_comments          'Adding full bibliography for 7158431.cif.'
_cod_database_code               7158431
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C14(H14), C19(H19), C20(H20),
 C22(H22), C23(H23), C26(H26), C29(H29)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.940
_oxdiff_exptl_absorpt_empirical_full_min 0.542
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.30574(3) 0.94255(7) 0.38214(4) 0.0782(2) Uani 1 1 d . . . . .
O1 O 0.01403(18) 0.4039(4) 0.26900(17) 0.0719(11) Uani 1 1 d . . . . .
O2 O 0.0611(2) 0.0533(4) 0.5998(2) 0.0842(12) Uani 1 1 d . . . . .
O3 O 0.1597(2) 0.0616(4) 0.5942(3) 0.1062(16) Uani 1 1 d . . . . .
N1 N 0.04894(15) 0.4925(4) 0.39114(17) 0.0348(8) Uani 1 1 d . . . . .
N2 N 0.06164(17) 0.1921(4) 0.4400(2) 0.0458(10) Uani 1 1 d . . . . .
N3 N 0.1079(2) 0.1184(5) 0.5892(2) 0.0586(12) Uani 1 1 d . . . . .
C1 C 0.1072(2) 0.7218(5) 0.3667(2) 0.0337(10) Uani 1 1 d . . . . .
C2 C 0.1538(2) 0.6492(5) 0.3368(2) 0.0465(12) Uani 1 1 d . . . . .
H2 H 0.145239 0.555241 0.314001 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2127(2) 0.7149(5) 0.3405(2) 0.0493(12) Uani 1 1 d . . . . .
H3 H 0.244032 0.666143 0.320734 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2238(2) 0.8534(5) 0.3740(2) 0.0462(12) Uani 1 1 d . . . . .
C5 C 0.1779(2) 0.9296(5) 0.4026(2) 0.0497(12) Uani 1 1 d . . . . .
H5 H 0.186170 1.024719 0.424110 0.060 Uiso 1 1 calc R U . . .
C6 C 0.1195(2) 0.8615(5) 0.3985(2) 0.0456(12) Uani 1 1 d . . . . .
H6 H 0.088055 0.911251 0.417602 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0436(2) 0.6494(5) 0.3641(2) 0.0415(11) Uani 1 1 d . . . . .
H7A H 0.020652 0.707211 0.395628 0.050 Uiso 1 1 calc R U . . .
H7B H 0.019078 0.651974 0.311774 0.050 Uiso 1 1 calc R U . . .
C8 C 0.0331(2) 0.3785(5) 0.3380(3) 0.0458(12) Uani 1 1 d . . . . .
C9 C 0.0403(2) 0.2271(5) 0.3696(3) 0.0510(13) Uani 1 1 d . . . . .
H9 H 0.028257 0.148171 0.335340 0.061 Uiso 1 1 calc R U . . .
C10 C 0.07825(19) 0.3101(5) 0.4909(2) 0.0333(10) Uani 1 1 d . . . . .
C11 C 0.10192(19) 0.2798(5) 0.5683(2) 0.0362(11) Uani 1 1 d . . . . .
C12 C 0.11923(19) 0.3874(5) 0.6245(2) 0.0407(11) Uani 1 1 d . . . . .
C13 C 0.1121(2) 0.5385(5) 0.6003(2) 0.0402(11) Uani 1 1 d . . . . .
C14 C 0.08910(19) 0.5723(5) 0.5239(2) 0.0371(11) Uani 1 1 d . . . . .
H14 H 0.084487 0.672589 0.508912 0.045 Uiso 1 1 calc R U . . .
C15 C 0.07259(18) 0.4602(4) 0.4688(2) 0.0301(10) Uani 1 1 d . . . . .
C16 C 0.1312(2) 0.6638(5) 0.6575(2) 0.0616(15) Uani 1 1 d . . . . .
H16A H 0.176450 0.660868 0.676939 0.092 Uiso 1 1 calc R U . . .
H16B H 0.109657 0.651466 0.699145 0.092 Uiso 1 1 calc R U . . .
H16C H 0.119583 0.758729 0.632878 0.092 Uiso 1 1 calc R U . . .
C17 C 0.1438(3) 0.3471(6) 0.7078(2) 0.0725(17) Uani 1 1 d . . . . .
H17A H 0.140543 0.240443 0.714252 0.109 Uiso 1 1 calc R U . . .
H17B H 0.118940 0.398106 0.738811 0.109 Uiso 1 1 calc R U . . .
H17C H 0.187637 0.377240 0.723220 0.109 Uiso 1 1 calc R U . . .
Br2 Br 0.33770(4) 0.92115(8) 0.70241(4) 0.1004(3) Uani 1 1 d . . . . .
O4 O 0.19741(17) 0.3236(4) 0.4024(2) 0.0684(10) Uani 1 1 d . . . . .
O5 O 0.4569(2) 0.1796(6) 0.2875(2) 0.1164(18) Uani 1 1 d . . . . .
O6 O 0.4850(2) 0.4100(7) 0.3086(3) 0.1201(19) Uani 1 1 d . . . . .
N4 N 0.29933(19) 0.3035(4) 0.4725(2) 0.0501(10) Uani 1 1 d . . . . .
N5 N 0.3409(2) 0.3261(4) 0.3335(2) 0.0536(11) Uani 1 1 d . . . . .
N6 N 0.4655(2) 0.2916(8) 0.3265(3) 0.0774(15) Uani 1 1 d . . . . .
C18 C 0.2899(2) 0.4545(6) 0.5854(3) 0.0527(13) Uani 1 1 d . . . . .
C19 C 0.3297(3) 0.4676(7) 0.6575(3) 0.0707(16) Uani 1 1 d . . . . .
H19 H 0.347555 0.381095 0.682492 0.085 Uiso 1 1 calc R U . . .
C20 C 0.3432(3) 0.6025(8) 0.6926(3) 0.0719(17) Uani 1 1 d . . . . .
H20 H 0.369510 0.608164 0.741197 0.086 Uiso 1 1 calc R U . . .
C21 C 0.3174(3) 0.7323(7) 0.6550(3) 0.0655(16) Uani 1 1 d . . . . .
C22 C 0.2771(2) 0.7240(6) 0.5840(3) 0.0641(15) Uani 1 1 d . . . . .
H22 H 0.258532 0.810354 0.559479 0.077 Uiso 1 1 calc R U . . .
C23 C 0.2647(2) 0.5855(6) 0.5501(3) 0.0544(13) Uani 1 1 d . . . . .
H23 H 0.238433 0.579767 0.501538 0.065 Uiso 1 1 calc R U . . .
C24 C 0.2771(2) 0.3053(6) 0.5452(3) 0.0601(14) Uani 1 1 d . . . . .
H24A H 0.298633 0.226467 0.578537 0.072 Uiso 1 1 calc R U . . .
H24B H 0.231711 0.284704 0.534939 0.072 Uiso 1 1 calc R U . . .
C25 C 0.2547(3) 0.3197(5) 0.4048(3) 0.0539(13) Uani 1 1 d . . . . .
C26 C 0.2818(3) 0.3356(5) 0.3370(3) 0.0583(14) Uani 1 1 d . . . . .
H26 H 0.253121 0.354792 0.291061 0.070 Uiso 1 1 calc R U . . .
C27 C 0.3832(2) 0.2996(5) 0.4029(2) 0.0463(12) Uani 1 1 d . . . . .
C28 C 0.3646(2) 0.2901(5) 0.4732(2) 0.0476(12) Uani 1 1 d . . . . .
C29 C 0.4110(2) 0.2649(6) 0.5393(2) 0.0582(14) Uani 1 1 d . . . . .
H29 H 0.398883 0.258790 0.586282 0.070 Uiso 1 1 calc R U . . .
C30 C 0.4742(3) 0.2488(7) 0.5370(3) 0.0686(16) Uani 1 1 d . . . . .
C31 C 0.4941(2) 0.2602(6) 0.4664(3) 0.0680(16) Uani 1 1 d . . . . .
C32 C 0.4476(2) 0.2838(6) 0.4024(2) 0.0542(13) Uani 1 1 d . . . . .
C33 C 0.5631(3) 0.2448(9) 0.4629(3) 0.113(3) Uani 1 1 d . . . . .
H33A H 0.567645 0.257074 0.410846 0.170 Uiso 1 1 calc R U . . .
H33B H 0.578178 0.147039 0.481096 0.170 Uiso 1 1 calc R U . . .
H33C H 0.587562 0.320554 0.494521 0.170 Uiso 1 1 calc R U . . .
C34 C 0.5220(3) 0.2202(8) 0.6106(3) 0.108(3) Uani 1 1 d . . . . .
H34A H 0.500943 0.223480 0.652963 0.162 Uiso 1 1 calc R U . . .
H34B H 0.554616 0.295868 0.617204 0.162 Uiso 1 1 calc R U . . .
H34C H 0.540945 0.122858 0.608382 0.162 Uiso 1 1 calc R U . . .
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_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1OB02015C 2021
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C7 118.7(3) . . ?
C8 N1 C15 120.9(4) . . ?
C15 N1 C7 120.3(3) . . ?
C9 N2 C10 116.7(4) . . ?
O2 N3 C11 118.2(4) . . ?
O3 N3 O2 124.8(5) . . ?
O3 N3 C11 117.0(4) . . ?
C2 C1 C7 120.8(4) . . ?
C6 C1 C2 119.4(4) . . ?
C6 C1 C7 119.8(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.4(4) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 Br1 118.8(4) . . ?
C3 C4 C5 122.1(4) . . ?
C5 C4 Br1 119.1(4) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.4(4) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 120.9(4) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N1 C7 C1 112.9(3) . . ?
N1 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C1 C7 H7A 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 N1 122.2(4) . . ?
O1 C8 C9 122.8(4) . . ?
N1 C8 C9 115.0(4) . . ?
N2 C9 C8 126.2(4) . . ?
N2 C9 H9 116.9 . . ?
C8 C9 H9 116.9 . . ?
N2 C10 C11 119.6(4) . . ?
N2 C10 C15 123.1(4) . . ?
C11 C10 C15 117.3(4) . . ?
C10 C11 N3 115.5(4) . . ?
C12 C11 N3 119.5(4) . . ?
C12 C11 C10 124.9(4) . . ?
C11 C12 C13 116.3(4) . . ?
C11 C12 C17 122.4(4) . . ?
C13 C12 C17 121.3(4) . . ?
C12 C13 C16 120.0(4) . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 C16 119.8(4) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.7(4) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 N1 118.0(3) . . ?
C10 C15 C14 119.5(3) . . ?
C14 C15 N1 122.5(4) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C25 N4 C24 118.4(4) . . ?
C25 N4 C28 121.5(4) . . ?
C28 N4 C24 120.1(4) . . ?
C26 N5 C27 115.7(4) . . ?
O5 N6 C32 116.7(6) . . ?
O6 N6 O5 126.2(5) . . ?
O6 N6 C32 117.1(6) . . ?
C19 C18 C24 121.9(5) . . ?
C23 C18 C19 117.1(5) . . ?
C23 C18 C24 120.9(4) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 C18 122.1(5) . . ?
C20 C19 H19 119.0 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.2(5) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 Br2 119.4(4) . . ?
C22 C21 Br2 120.0(5) . . ?
C22 C21 C20 120.6(5) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 C21 118.5(5) . . ?
C23 C22 H22 120.7 . . ?
C18 C23 H23 118.7 . . ?
C22 C23 C18 122.5(5) . . ?
C22 C23 H23 118.7 . . ?
N4 C24 C18 111.6(4) . . ?
N4 C24 H24A 109.3 . . ?
N4 C24 H24B 109.3 . . ?
C18 C24 H24A 109.3 . . ?
C18 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
O4 C25 N4 122.7(5) . . ?
O4 C25 C26 123.0(5) . . ?
N4 C25 C26 114.3(5) . . ?
N5 C26 C25 127.2(5) . . ?
N5 C26 H26 116.4 . . ?
C25 C26 H26 116.4 . . ?
N5 C27 C28 123.5(4) . . ?
C32 C27 N5 118.3(4) . . ?
C32 C27 C28 118.2(4) . . ?
C27 C28 N4 117.5(4) . . ?
C29 C28 N4 123.7(4) . . ?
C29 C28 C27 118.8(4) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 C28 121.7(4) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 C31 120.4(4) . . ?
C29 C30 C34 119.1(5) . . ?
C31 C30 C34 120.5(5) . . ?
C30 C31 C33 121.1(5) . . ?
C32 C31 C30 116.7(5) . . ?
C32 C31 C33 122.2(5) . . ?
C27 C32 N6 116.8(4) . . ?
C31 C32 N6 119.0(5) . . ?
C31 C32 C27 124.2(4) . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C34 H34A 109.5 . . ?
C30 C34 H34B 109.5 . . ?
C30 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.905(5) . ?
O1 C8 1.232(5) . ?
O2 N3 1.209(5) . ?
O3 N3 1.207(5) . ?
N1 C7 1.473(5) . ?
N1 C8 1.380(5) . ?
N1 C15 1.400(5) . ?
N2 C9 1.280(5) . ?
N2 C10 1.384(5) . ?
N3 C11 1.482(6) . ?
C1 C2 1.387(6) . ?
C1 C6 1.368(6) . ?
C1 C7 1.500(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(6) . ?
C4 C5 1.378(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(6) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.455(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(5) . ?
C10 C15 1.390(5) . ?
C11 C12 1.379(6) . ?
C12 C13 1.410(6) . ?
C12 C17 1.509(5) . ?
C13 C14 1.380(5) . ?
C13 C16 1.507(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
Br2 C21 1.889(5) . ?
O4 C25 1.221(5) . ?
O5 N6 1.206(6) . ?
O6 N6 1.201(6) . ?
N4 C24 1.472(5) . ?
N4 C25 1.381(6) . ?
N4 C28 1.404(6) . ?
N5 C26 1.286(6) . ?
N5 C27 1.391(5) . ?
N6 C32 1.485(6) . ?
C18 C19 1.390(6) . ?
C18 C23 1.378(6) . ?
C18 C24 1.505(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.356(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.390(7) . ?
C21 C22 1.376(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.373(6) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.455(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.396(6) . ?
C27 C32 1.389(6) . ?
C28 C29 1.390(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.372(7) . ?
C30 C31 1.415(7) . ?
C30 C34 1.507(6) . ?
C31 C32 1.365(6) . ?
C31 C33 1.501(7) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C4 C5 C6 -177.9(3) . . . . ?
O1 C8 C9 N2 177.7(5) . . . . ?
O2 N3 C11 C10 -83.0(5) . . . . ?
O2 N3 C11 C12 96.7(5) . . . . ?
O3 N3 C11 C10 96.9(5) . . . . ?
O3 N3 C11 C12 -83.4(6) . . . . ?
N1 C8 C9 N2 -2.7(7) . . . . ?
N2 C10 C11 N3 0.7(6) . . . . ?
N2 C10 C11 C12 -179.1(4) . . . . ?
N2 C10 C15 N1 0.0(6) . . . . ?
N2 C10 C15 C14 178.7(4) . . . . ?
N3 C11 C12 C13 -180.0(4) . . . . ?
N3 C11 C12 C17 -0.6(6) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C1 C6 C5 -1.4(6) . . . . ?
C2 C1 C7 N1 48.3(5) . . . . ?
C2 C3 C4 Br1 178.2(3) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C4 C5 C6 C1 -0.1(7) . . . . ?
C6 C1 C2 C3 1.6(6) . . . . ?
C6 C1 C7 N1 -132.2(4) . . . . ?
C7 N1 C8 O1 -0.9(6) . . . . ?
C7 N1 C8 C9 179.5(4) . . . . ?
C7 N1 C15 C10 -178.3(3) . . . . ?
C7 N1 C15 C14 3.1(6) . . . . ?
C7 C1 C2 C3 -178.8(4) . . . . ?
C7 C1 C6 C5 179.1(4) . . . . ?
C8 N1 C7 C1 -107.2(4) . . . . ?
C8 N1 C15 C10 -1.5(6) . . . . ?
C8 N1 C15 C14 179.9(4) . . . . ?
C9 N2 C10 C11 -179.8(4) . . . . ?
C9 N2 C10 C15 0.1(6) . . . . ?
C10 N2 C9 C8 1.3(7) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
C10 C11 C12 C17 179.2(4) . . . . ?
C11 C10 C15 N1 179.9(4) . . . . ?
C11 C10 C15 C14 -1.4(6) . . . . ?
C11 C12 C13 C14 -0.1(6) . . . . ?
C11 C12 C13 C16 -178.7(4) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C13 C14 C15 N1 179.8(4) . . . . ?
C13 C14 C15 C10 1.2(6) . . . . ?
C15 N1 C7 C1 69.7(5) . . . . ?
C15 N1 C8 O1 -177.8(4) . . . . ?
C15 N1 C8 C9 2.6(6) . . . . ?
C15 C10 C11 N3 -179.2(4) . . . . ?
C15 C10 C11 C12 1.0(6) . . . . ?
C16 C13 C14 C15 178.2(4) . . . . ?
C17 C12 C13 C14 -179.5(4) . . . . ?
C17 C12 C13 C16 1.9(6) . . . . ?
Br2 C21 C22 C23 178.1(4) . . . . ?
O4 C25 C26 N5 -176.6(5) . . . . ?
O5 N6 C32 C27 -79.3(7) . . . . ?
O5 N6 C32 C31 99.8(6) . . . . ?
O6 N6 C32 C27 97.9(6) . . . . ?
O6 N6 C32 C31 -82.9(7) . . . . ?
N4 C25 C26 N5 5.0(7) . . . . ?
N4 C28 C29 C30 178.4(5) . . . . ?
N5 C27 C28 N4 2.0(7) . . . . ?
N5 C27 C28 C29 -179.3(4) . . . . ?
N5 C27 C32 N6 -2.0(7) . . . . ?
N5 C27 C32 C31 178.8(5) . . . . ?
C18 C19 C20 C21 -0.9(8) . . . . ?
C19 C18 C23 C22 -0.8(7) . . . . ?
C19 C18 C24 N4 -118.1(5) . . . . ?
C19 C20 C21 Br2 -178.5(4) . . . . ?
C19 C20 C21 C22 1.9(8) . . . . ?
C20 C21 C22 C23 -2.2(8) . . . . ?
C21 C22 C23 C18 1.7(8) . . . . ?
C23 C18 C19 C20 0.4(8) . . . . ?
C23 C18 C24 N4 58.8(6) . . . . ?
C24 N4 C25 O4 -5.8(7) . . . . ?
C24 N4 C25 C26 172.6(4) . . . . ?
C24 N4 C28 C27 -175.6(4) . . . . ?
C24 N4 C28 C29 5.8(7) . . . . ?
C24 C18 C19 C20 177.4(5) . . . . ?
C24 C18 C23 C22 -177.8(4) . . . . ?
C25 N4 C24 C18 -102.1(5) . . . . ?
C25 N4 C28 C27 2.5(6) . . . . ?
C25 N4 C28 C29 -176.1(4) . . . . ?
C26 N5 C27 C28 -2.7(7) . . . . ?
C26 N5 C27 C32 178.1(4) . . . . ?
C27 N5 C26 C25 -1.0(7) . . . . ?
C27 C28 C29 C30 -0.2(8) . . . . ?
C28 N4 C24 C18 76.0(5) . . . . ?
C28 N4 C25 O4 176.0(4) . . . . ?
C28 N4 C25 C26 -5.5(6) . . . . ?
C28 C27 C32 N6 178.8(5) . . . . ?
C28 C27 C32 C31 -0.3(8) . . . . ?
C28 C29 C30 C31 1.1(9) . . . . ?
C28 C29 C30 C34 -179.4(5) . . . . ?
C29 C30 C31 C32 -1.5(9) . . . . ?
C29 C30 C31 C33 179.2(6) . . . . ?
C30 C31 C32 N6 -178.0(5) . . . . ?
C30 C31 C32 C27 1.2(8) . . . . ?
C32 C27 C28 N4 -178.8(4) . . . . ?
C32 C27 C28 C29 -0.2(7) . . . . ?
C33 C31 C32 N6 1.3(9) . . . . ?
C33 C31 C32 C27 -179.6(5) . . . . ?
C34 C30 C31 C32 179.0(5) . . . . ?
C34 C30 C31 C33 -0.3(9) . . . . ?
