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#$Date: 2024-08-05 22:57:12 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293926 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160005.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_7160005
loop_
_publ_author_name
'Lalji, Ram Sunil Kumar'
'Monika, ?'
'Gupta, Mohit'
'Kumar, Sandeep'
'Butcher, Ray J.'
'Singh, Brajendra Kumar'
_publ_section_title
;
 Expedient, regioselective C-H chalcogenation of
 3,4-dihydro-1,4-benzoxazines using a palladium-copper catalyst.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5809
_journal_page_last               5815
_journal_paper_doi               10.1039/d4ob00524d
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H13 Br N4 O3 Se'
_chemical_formula_sum            'C18 H13 Br N4 O3 Se'
_chemical_formula_weight         492.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-10-08 deposited with the CCDC.	2024-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0959(3)
_cell_length_b                   14.8987(6)
_cell_length_c                   19.7130(7)
_cell_measurement_reflns_used    5579
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      29.7640
_cell_measurement_theta_min      3.4270
_cell_volume                     1790.35(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.820
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyP'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.820
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11746
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.832
_diffrn_reflns_theta_min         3.389
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.357
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.044
_refine_diff_density_max         1.651
_refine_diff_density_min         -1.585
_refine_diff_density_rms         0.189
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.52(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     956
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0710
_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)+(0.0925P)²+14.7041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.1869
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.705
_reflns_number_gt                3813
_reflns_number_total             4337
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00524d2.cif
_cod_data_source_block           5h
_cod_depositor_comments          'Adding full bibliography for 7160005.cif.'
_cod_database_code               7160005
_shelx_shelxl_version_number     2019/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_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
Se1 Se 0.6355(2) 0.42147(8) 0.45017(7) 0.0125(3) Uani 0.719(3) 1 d D U P A 1
Br1 Br 1.2855(4) 0.26011(17) 0.68745(12) 0.0184(5) Uani 0.719(3) 1 d D U P A 1
O2 O 0.731(2) 0.7823(9) 0.6248(9) 0.013(3) Uani 0.719(3) 1 d D U P A 1
O3 O 0.717(2) 0.6449(11) 0.6615(6) 0.016(2) Uani 0.719(3) 1 d D U P A 1
N4 N 0.723(2) 0.7000(9) 0.6152(5) 0.0126(19) Uani 0.719(3) 1 d D U P A 1
C1 C 0.8344(12) 0.3768(5) 0.5184(3) 0.0135(13) Uani 0.719(3) 1 d DG U P A 1
C2 C 0.7620(11) 0.3079(5) 0.5604(4) 0.0132(15) Uani 0.719(3) 1 d DG U P A 1
H2A H 0.618489 0.284095 0.554861 0.016 Uiso 0.719(3) 1 calc R U P A 1
C3 C 0.8995(14) 0.2738(5) 0.6104(4) 0.0184(16) Uani 0.719(3) 1 d DG U P A 1
H3A H 0.849936 0.226695 0.639039 0.022 Uiso 0.719(3) 1 calc R U P A 1
C4 C 1.1094(13) 0.3086(5) 0.6184(4) 0.0152(15) Uani 0.719(3) 1 d DG U P A 1
C5 C 1.1819(10) 0.3775(5) 0.5765(4) 0.0140(17) Uani 0.719(3) 1 d DG U P A 1
H5A H 1.325374 0.401261 0.582032 0.017 Uiso 0.719(3) 1 calc R U P A 1
C6 C 1.0444(13) 0.4116(5) 0.5265(4) 0.0131(15) Uani 0.719(3) 1 d DG U P A 1
H6A H 1.093930 0.458662 0.497853 0.016 Uiso 0.719(3) 1 calc R U P A 1
C7 C 0.6677(14) 0.5478(4) 0.4673(3) 0.0115(14) Uani 0.719(3) 1 d DG U P A 1
C8 C 0.6834(14) 0.5782(5) 0.5338(3) 0.0118(15) Uani 0.719(3) 1 d DG U P A 1
H8A H 0.673273 0.536913 0.570334 0.014 Uiso 0.719(3) 1 calc R U P A 1
C9 C 0.7137(15) 0.6691(5) 0.5467(3) 0.0122(15) Uani 0.719(3) 1 d DG U P A 1
C10 C 0.7285(14) 0.7295(4) 0.4932(4) 0.0114(15) Uani 0.719(3) 1 d DG U P A 1
H10A H 0.749222 0.791622 0.502057 0.014 Uiso 0.719(3) 1 calc R U P A 1
C11 C 0.7128(15) 0.6991(4) 0.4267(3) 0.0109(14) Uani 0.719(3) 1 d DG U P A 1
C14 C 0.6825(15) 0.6082(5) 0.4138(3) 0.0119(13) Uani 0.719(3) 1 d DG U P A 1
O1 O 0.7300(18) 0.7636(7) 0.3784(5) 0.0116(16) Uani 0.719(3) 1 d D U P A 1
C12 C 0.745(2) 0.7357(8) 0.3069(6) 0.0137(17) Uani 0.719(3) 1 d D U P A 1
H12A H 0.859028 0.771973 0.283912 0.016 Uiso 0.719(3) 1 calc R U P A 1
H12B H 0.603298 0.747610 0.284187 0.016 Uiso 0.719(3) 1 calc R U P A 1
C13 C 0.800(2) 0.6399(8) 0.2999(6) 0.0130(15) Uani 0.719(3) 1 d D U P A 1
H13A H 0.957139 0.631241 0.310216 0.016 Uiso 0.719(3) 1 calc R U P A 1
H13B H 0.774875 0.621309 0.252320 0.016 Uiso 0.719(3) 1 calc R U P A 1
N1 N 0.6685(16) 0.5818(7) 0.3451(5) 0.0126(13) Uani 0.719(3) 1 d D U P A 1
C15 C 0.5018(11) 0.5375(5) 0.3199(4) 0.0134(15) Uani 0.719(3) 1 d DG U P A 1
N2 N 0.3319(12) 0.5096(5) 0.3620(3) 0.0130(17) Uani 0.719(3) 1 d DG U P A 1
C16 C 0.1500(11) 0.4666(6) 0.3345(4) 0.0166(19) Uani 0.719(3) 1 d DG U P A 1
H16A H 0.033881 0.447555 0.363255 0.020 Uiso 0.719(3) 1 calc R U P A 1
C17 C 0.1380(12) 0.4516(6) 0.2650(4) 0.0186(19) Uani 0.719(3) 1 d DG U P A 1
H17A H 0.013659 0.422221 0.246274 0.022 Uiso 0.719(3) 1 calc R U P A 1
C18 C 0.3079(14) 0.4795(6) 0.2230(3) 0.020(2) Uani 0.719(3) 1 d DG U P A 1
H18A H 0.299665 0.469201 0.175509 0.024 Uiso 0.719(3) 1 calc R U P A 1
N3 N 0.4898(12) 0.5224(6) 0.2505(3) 0.0168(17) Uani 0.719(3) 1 d DG U P A 1
Se1A Se 0.8593(6) 0.4202(2) 0.44860(18) 0.0192(9) Uani 0.281(3) 1 d D U P A 2
Br1A Br 1.2009(11) 0.2624(5) 0.6879(4) 0.0294(16) Uani 0.281(3) 1 d D U P A 2
O2A O 0.779(8) 0.779(2) 0.625(3) 0.015(4) Uani 0.281(3) 1 d D U P A 2
O3A O 0.782(6) 0.640(3) 0.6592(16) 0.014(4) Uani 0.281(3) 1 d D U P A 2
N4A N 0.770(7) 0.697(2) 0.6149(12) 0.013(2) Uani 0.281(3) 1 d D U P A 2
C1A C 0.716(3) 0.3890(12) 0.5370(7) 0.0186(17) Uani 0.281(3) 1 d DG U P A 2
C2A C 0.739(4) 0.2968(11) 0.5452(9) 0.0176(18) Uani 0.281(3) 1 d DG U P A 2
H2AA H 0.669746 0.256939 0.514155 0.021 Uiso 0.281(3) 1 calc R U P A 2
C3A C 0.862(4) 0.2629(10) 0.5987(11) 0.0194(19) Uani 0.281(3) 1 d DG U P A 2
H3AA H 0.877122 0.199922 0.604272 0.023 Uiso 0.281(3) 1 calc R U P A 2
C4A C 0.962(4) 0.3213(14) 0.6441(10) 0.022(2) Uani 0.281(3) 1 d DG U P A 2
C5A C 0.940(4) 0.4135(13) 0.6359(10) 0.022(2) Uani 0.281(3) 1 d DG U P A 2
H5AA H 1.008732 0.453370 0.666908 0.026 Uiso 0.281(3) 1 calc R U P A 2
C6A C 0.817(4) 0.4474(10) 0.5824(10) 0.020(2) Uani 0.281(3) 1 d DG U P A 2
H6AA H 0.801356 0.510388 0.576791 0.025 Uiso 0.281(3) 1 calc R U P A 2
C7A C 0.833(4) 0.5472(8) 0.4661(8) 0.0137(16) Uani 0.281(3) 1 d DG U P A 2
C8A C 0.808(4) 0.5766(11) 0.5326(7) 0.0126(18) Uani 0.281(3) 1 d DG U P A 2
H8AA H 0.813755 0.534788 0.568899 0.015 Uiso 0.281(3) 1 calc R U P A 2
C9A C 0.773(4) 0.6671(13) 0.5458(7) 0.0123(17) Uani 0.281(3) 1 d DG U P A 2
C10A C 0.764(4) 0.7283(9) 0.4927(10) 0.0116(18) Uani 0.281(3) 1 d DG U P A 2
H10B H 0.739993 0.790133 0.501760 0.014 Uiso 0.281(3) 1 calc R U P A 2
C11A C 0.789(4) 0.6989(10) 0.4262(9) 0.0115(16) Uani 0.281(3) 1 d DG U P A 2
C14A C 0.824(4) 0.6084(10) 0.4129(7) 0.0122(15) Uani 0.281(3) 1 d DG U P A 2
O1A O 0.776(5) 0.7623(16) 0.3768(12) 0.0117(19) Uani 0.281(3) 1 d D U P A 2
C12A C 0.691(6) 0.7346(18) 0.3097(14) 0.0128(19) Uani 0.281(3) 1 d D U P A 2
H12C H 0.537901 0.755832 0.305057 0.015 Uiso 0.281(3) 1 calc R U P A 2
H12D H 0.779324 0.764153 0.273975 0.015 Uiso 0.281(3) 1 calc R U P A 2
C13A C 0.696(5) 0.6376(17) 0.2989(14) 0.0134(17) Uani 0.281(3) 1 d D U P A 2
H13C H 0.749345 0.627218 0.252091 0.016 Uiso 0.281(3) 1 calc R U P A 2
H13D H 0.543184 0.615790 0.300793 0.016 Uiso 0.281(3) 1 calc R U P A 2
N1A N 0.827(4) 0.5802(16) 0.3440(9) 0.0140(16) Uani 0.281(3) 1 d D U P A 2
C15A C 0.998(3) 0.5366(15) 0.3189(9) 0.017(2) Uani 0.281(3) 1 d DG U P A 2
N2A N 1.008(3) 0.5237(16) 0.2491(9) 0.020(3) Uani 0.281(3) 1 d DG U P A 2
C16A C 1.188(4) 0.4811(18) 0.2204(8) 0.022(3) Uani 0.281(3) 1 d DG U P A 2
H16B H 1.194685 0.472233 0.172689 0.026 Uiso 0.281(3) 1 calc R U P A 2
C17A C 1.359(3) 0.4514(17) 0.2614(11) 0.023(4) Uani 0.281(3) 1 d DG U P A 2
H17B H 1.481940 0.422249 0.241774 0.028 Uiso 0.281(3) 1 calc R U P A 2
C18A C 1.349(3) 0.4643(17) 0.3312(10) 0.022(3) Uani 0.281(3) 1 d DG U P A 2
H18B H 1.465614 0.443980 0.359226 0.026 Uiso 0.281(3) 1 calc R U P A 2
N3A N 1.169(3) 0.5069(16) 0.3599(7) 0.019(3) Uani 0.281(3) 1 d DG U P A 2
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'
Se Se -0.0929 2.2259 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 Se1 C1 98.7(3) . . ?
O3 N4 O2 123.1(12) . . ?
O3 N4 C9 119.1(11) . . ?
O2 N4 C9 117.8(11) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 Se1 118.0(4) . . ?
C6 C1 Se1 122.0(4) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 Br1 122.2(4) . . ?
C3 C4 Br1 117.8(4) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
C8 C7 C14 120.0 . . ?
C8 C7 Se1 119.4(4) . . ?
C14 C7 Se1 120.5(4) . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 N4 120.4(7) . . ?
C8 C9 N4 119.6(7) . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
O1 C11 C14 124.8(6) . . ?
O1 C11 C10 115.2(6) . . ?
C14 C11 C10 120.0 . . ?
C11 C14 C7 120.0 . . ?
C11 C14 N1 117.1(6) . . ?
C7 C14 N1 122.9(6) . . ?
C11 O1 C12 118.5(9) . . ?
O1 C12 C13 112.2(10) . . ?
O1 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 N1 112.9(10) . . ?
C12 C13 H13A 109.0 . . ?
N1 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
N1 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 N1 C14 123.3(8) . . ?
C15 N1 C13 119.2(9) . . ?
C14 N1 C13 112.5(9) . . ?
N1 C15 N2 120.2(7) . . ?
N1 C15 N3 119.7(7) . . ?
N2 C15 N3 120.0 . . ?
C16 N2 C15 120.0 . . ?
N2 C16 C17 120.0 . . ?
N2 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C17 C18 N3 120.0 . . ?
C17 C18 H18A 120.0 . . ?
N3 C18 H18A 120.0 . . ?
C18 N3 C15 120.0 . . ?
C7A Se1A C1A 92.1(7) . . ?
O3A N4A O2A 125(3) . . ?
O3A N4A C9A 117(2) . . ?
O2A N4A C9A 118(3) . . ?
C2A C1A C6A 120.0 . . ?
C2A C1A Se1A 106.7(11) . . ?
C6A C1A Se1A 102.8(10) . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2AA 120.0 . . ?
C1A C2A H2AA 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3AA 120.0 . . ?
C4A C3A H3AA 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A Br1A 125.7(12) . . ?
C3A C4A Br1A 109.9(12) . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5AA 120.0 . . ?
C6A C5A H5AA 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6AA 120.0 . . ?
C1A C6A H6AA 120.0 . . ?
C8A C7A C14A 120.0 . . ?
C8A C7A Se1A 119.1(9) . . ?
C14A C7A Se1A 120.7(9) . . ?
C7A C8A C9A 120.0 . . ?
C7A C8A H8AA 120.0 . . ?
C9A C8A H8AA 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C10A C9A N4A 120.6(15) . . ?
C8A C9A N4A 119.1(15) . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10B 120.0 . . ?
C11A C10A H10B 120.0 . . ?
O1A C11A C14A 123.2(15) . . ?
O1A C11A C10A 116.7(15) . . ?
C14A C11A C10A 120.0 . . ?
C11A C14A C7A 120.0 . . ?
C11A C14A N1A 117.9(13) . . ?
C7A C14A N1A 121.8(13) . . ?
C11A O1A C12A 118(2) . . ?
C13A C12A O1A 113(2) . . ?
C13A C12A H12C 108.9 . . ?
O1A C12A H12C 108.9 . . ?
C13A C12A H12D 108.9 . . ?
O1A C12A H12D 108.9 . . ?
H12C C12A H12D 107.7 . . ?
C12A C13A N1A 120(2) . . ?
C12A C13A H13C 107.3 . . ?
N1A C13A H13C 107.3 . . ?
C12A C13A H13D 107.3 . . ?
N1A C13A H13D 107.3 . . ?
H13C C13A H13D 106.9 . . ?
C15A N1A C14A 120.8(18) . . ?
C15A N1A C13A 119(2) . . ?
C14A N1A C13A 113.6(17) . . ?
N1A C15A N2A 118.1(15) . . ?
N1A C15A N3A 121.9(15) . . ?
N2A C15A N3A 120.0 . . ?
C16A N2A C15A 120.0 . . ?
N2A C16A C17A 120.0 . . ?
N2A C16A H16B 120.0 . . ?
C17A C16A H16B 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C16A C17A H17B 120.0 . . ?
C18A C17A H17B 120.0 . . ?
N3A C18A C17A 120.0 . . ?
N3A C18A H18B 120.0 . . ?
C17A C18A H18B 120.0 . . ?
C18A N3A C15A 120.0 . . ?
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
Se1 C7 1.922(5) . ?
Se1 C1 1.930(5) . ?
Br1 C4 1.877(5) . ?
O2 N4 1.242(12) . ?
O3 N4 1.229(12) . ?
N4 C9 1.427(10) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2A 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3A 0.9500 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.3900 . ?
C7 C14 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8A 0.9500 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C10 H10A 0.9500 . ?
C11 O1 1.357(9) . ?
C11 C14 1.3900 . ?
C14 N1 1.413(10) . ?
O1 C12 1.472(12) . ?
C12 C13 1.472(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N1 1.476(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N1 C15 1.310(10) . ?
C15 N2 1.3900 . ?
C15 N3 1.3900 . ?
N2 C16 1.3900 . ?
C16 C17 1.3900 . ?
C16 H16A 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17A 0.9500 . ?
C18 N3 1.3900 . ?
C18 H18A 0.9500 . ?
Se1A C7A 1.930(12) . ?
Se1A C1A 2.004(17) . ?
Br1A C4A 1.905(15) . ?
O2A N4A 1.24(2) . ?
O3A N4A 1.23(2) . ?
N4A C9A 1.434(18) . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A C3A 1.3900 . ?
C2A H2AA 0.9500 . ?
C3A C4A 1.3900 . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.3900 . ?
C5A C6A 1.3900 . ?
C5A H5AA 0.9500 . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.3900 . ?
C7A C14A 1.3900 . ?
C8A C9A 1.3900 . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.3900 . ?
C10A C11A 1.3900 . ?
C10A H10B 0.9500 . ?
C11A O1A 1.359(18) . ?
C11A C14A 1.3900 . ?
C14A N1A 1.422(18) . ?
O1A C12A 1.48(2) . ?
C12A C13A 1.46(2) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A N1A 1.47(2) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
N1A C15A 1.326(18) . ?
C15A N2A 1.3900 . ?
C15A N3A 1.3900 . ?
N2A C16A 1.3900 . ?
C16A C17A 1.3900 . ?
C16A H16B 0.9500 . ?
C17A C18A 1.3900 . ?
C17A H17B 0.9500 . ?
C18A N3A 1.3900 . ?
C18A H18B 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13^a H13A^a Br1^a 0.99 3.31 3.679(12) 104.3 2_764 yes
C16^a H16A^a Se1^a 0.95 3.00 3.935(6) 169.5 1_455 yes
C17^a H17A^a O3^a 0.95 2.40 3.303(13) 158.3 2_564 yes
C6A^b H6AA^b O3A^b 0.95 2.52 3.25(5) 133.2 . yes
C12A^b H12C^b Br1A^b 0.99 2.74 3.39(3) 123.2 2_664 yes
C17A^b H17B^b O3A^b 0.95 2.36 3.27(4) 160.3 2_764 yes
C18A^b H18B^b Se1A^b 0.95 3.00 3.933(16) 168.1 1_655 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0 . . . . ?
Se1 C1 C2 C3 -179.8(6) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 Br1 179.5(6) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
Br1 C4 C5 C6 -179.5(6) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
Se1 C1 C6 C5 179.8(6) . . . . ?
C14 C7 C8 C9 0.0 . . . . ?
Se1 C7 C8 C9 177.9(6) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C7 C8 C9 N4 178.1(9) . . . . ?
O3 N4 C9 C10 -177.6(10) . . . . ?
O2 N4 C9 C10 4.1(16) . . . . ?
O3 N4 C9 C8 4.4(15) . . . . ?
O2 N4 C9 C8 -174.0(10) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
N4 C9 C10 C11 -178.0(9) . . . . ?
C9 C10 C11 O1 -179.8(9) . . . . ?
C9 C10 C11 C14 0.0 . . . . ?
O1 C11 C14 C7 179.8(10) . . . . ?
C10 C11 C14 C7 0.0 . . . . ?
O1 C11 C14 N1 -0.1(10) . . . . ?
C10 C11 C14 N1 -179.8(9) . . . . ?
C8 C7 C14 C11 0.0 . . . . ?
Se1 C7 C14 C11 -177.9(6) . . . . ?
C8 C7 C14 N1 179.8(9) . . . . ?
Se1 C7 C14 N1 1.9(8) . . . . ?
C14 C11 O1 C12 -7.9(14) . . . . ?
C10 C11 O1 C12 171.9(9) . . . . ?
C11 O1 C12 C13 -15.7(16) . . . . ?
O1 C12 C13 N1 46.0(15) . . . . ?
C11 C14 N1 C15 -123.8(10) . . . . ?
C7 C14 N1 C15 56.4(13) . . . . ?
C11 C14 N1 C13 30.9(12) . . . . ?
C7 C14 N1 C13 -149.0(9) . . . . ?
C12 C13 N1 C15 101.4(13) . . . . ?
C12 C13 N1 C14 -54.4(14) . . . . ?
C14 N1 C15 N2 -3.6(14) . . . . ?
C13 N1 C15 N2 -156.6(9) . . . . ?
C14 N1 C15 N3 173.1(8) . . . . ?
C13 N1 C15 N3 20.0(13) . . . . ?
N1 C15 N2 C16 176.7(9) . . . . ?
N3 C15 N2 C16 0.0 . . . . ?
C15 N2 C16 C17 0.0 . . . . ?
N2 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 N3 0.0 . . . . ?
C17 C18 N3 C15 0.0 . . . . ?
N1 C15 N3 C18 -176.7(9) . . . . ?
N2 C15 N3 C18 0.0 . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
Se1A C1A C2A C3A 116.1(12) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C2A C3A C4A Br1A -157.7(16) . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
Br1A C4A C5A C6A 154.0(18) . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
Se1A C1A C6A C5A -118.1(12) . . . . ?
C14A C7A C8A C9A 0.0 . . . . ?
Se1A C7A C8A C9A -175.5(17) . . . . ?
C7A C8A C9A C10A 0.0 . . . . ?
C7A C8A C9A N4A -174(3) . . . . ?
O3A N4A C9A C10A -179(3) . . . . ?
O2A N4A C9A C10A -6(5) . . . . ?
O3A N4A C9A C8A -5(4) . . . . ?
O2A N4A C9A C8A 167(3) . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
N4A C9A C10A C11A 173(3) . . . . ?
C9A C10A C11A O1A 179(2) . . . . ?
C9A C10A C11A C14A 0.0 . . . . ?
O1A C11A C14A C7A -179(3) . . . . ?
C10A C11A C14A C7A 0.0 . . . . ?
O1A C11A C14A N1A -5(3) . . . . ?
C10A C11A C14A N1A 174(2) . . . . ?
C8A C7A C14A C11A 0.0 . . . . ?
Se1A C7A C14A C11A 175.4(17) . . . . ?
C8A C7A C14A N1A -173(2) . . . . ?
Se1A C7A C14A N1A 2(2) . . . . ?
C14A C11A O1A C12A 29(4) . . . . ?
C10A C11A O1A C12A -150(3) . . . . ?
C11A O1A C12A C13A -18(5) . . . . ?
O1A C12A C13A N1A -15(5) . . . . ?
C11A C14A N1A C15A 124(2) . . . . ?
C7A C14A N1A C15A -62(3) . . . . ?
C11A C14A N1A C13A -27(3) . . . . ?
C7A C14A N1A C13A 147(2) . . . . ?
C12A C13A N1A C15A -115(3) . . . . ?
C12A C13A N1A C14A 37(4) . . . . ?
C14A N1A C15A N2A -169.7(18) . . . . ?
C13A N1A C15A N2A -20(3) . . . . ?
C14A N1A C15A N3A 8(3) . . . . ?
C13A N1A C15A N3A 158(2) . . . . ?
N1A C15A N2A C16A 178(3) . . . . ?
N3A C15A N2A C16A 0.0 . . . . ?
C15A N2A C16A C17A 0.0 . . . . ?
N2A C16A C17A C18A 0.0 . . . . ?
C16A C17A C18A N3A 0.0 . . . . ?
C17A C18A N3A C15A 0.0 . . . . ?
N1A C15A N3A C18A -178(3) . . . . ?
N2A C15A N3A C18A 0.0 . . . . ?
