#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/15/1551599.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_1551599
loop_
_publ_author_name
'HWANG, Long-Chih'
'CHUANG, Chung-Lin'
'SU, Chun-Wei'
'LEE, Gene-Hsiang'
_publ_section_title
;
 Packing of Two Independent Molecules:
 3-Amino-2-benzyl-6-bromo-1,2,4-triazin-5(2H)-one
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              33
_journal_paper_doi               10.2116/xraystruct.32.33
_journal_volume                  32
_journal_year                    2016
_chemical_formula_sum            'C10 H9 Br N4 O'
_chemical_formula_weight         281.12
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   23.6829(13)
_cell_length_b                   7.5558(4)
_cell_length_c                   24.1777(13)
_cell_measurement_reflns_used    2177
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      19.98
_cell_measurement_theta_min      2.41
_cell_volume                     4326.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER SMART SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.0982
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23631
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    3.784
_exptl_absorpt_correction_T_max  0.9282
_exptl_absorpt_correction_T_min  0.4172
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1348
_reflns_number_gt                3144
_reflns_number_total             4959
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            32_33_1.txt
_cod_data_source_block           ic11962
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/andrius/struct/COD-crude-data/automatic-downloads/current/J-STAGE/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6524 2018-11-02 12:15:13Z antanas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1551599
loop_
_symmetry_equiv_pos_as_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'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 1.07126(2) 0.42441(7) 0.09454(2) 0.04362(17) Uani 1 1 d .
O1 O 0.98945(14) 0.1109(4) 0.07389(16) 0.0502(10) Uani 1 1 d .
N1 N 0.97175(16) 0.5753(5) 0.06810(16) 0.0346(9) Uani 1 1 d .
N2 N 0.91716(15) 0.5775(5) 0.05029(16) 0.0345(9) Uani 1 1 d .
N3 N 0.91289(15) 0.2655(5) 0.04505(15) 0.0331(9) Uani 1 1 d .
N4 N 0.83797(15) 0.4320(5) 0.01726(17) 0.0407(10) Uani 1 1 d .
H4A H 0.8203 0.3363 0.0088 0.049 Uiso 1 1 calc R
H4B H 0.8220 0.5330 0.0123 0.049 Uiso 1 1 calc R
C1 C 0.96651(19) 0.2527(6) 0.06511(18) 0.0336(11) Uani 1 1 d .
C2 C 0.99454(18) 0.4233(6) 0.07406(19) 0.0316(11) Uani 1 1 d .
C3 C 0.88963(18) 0.4239(6) 0.03791(19) 0.0312(10) Uani 1 1 d .
C4 C 0.8923(2) 0.7544(6) 0.0447(2) 0.0390(12) Uani 1 1 d .
H4C H 0.8727 0.7617 0.0096 0.047 Uiso 1 1 calc R
H4D H 0.9225 0.8414 0.0443 0.047 Uiso 1 1 calc R
C5 C 0.85154(19) 0.7998(6) 0.0907(2) 0.0344(11) Uani 1 1 d .
C6 C 0.8053(2) 0.9040(7) 0.0791(2) 0.0525(14) Uani 1 1 d .
H6A H 0.7985 0.9401 0.0429 0.063 Uiso 1 1 calc R
C7 C 0.7692(3) 0.9550(8) 0.1202(3) 0.0659(18) Uani 1 1 d .
H7A H 0.7381 1.0254 0.1118 0.079 Uiso 1 1 calc R
C8 C 0.7782(3) 0.9038(8) 0.1734(3) 0.0613(17) Uani 1 1 d .
H8C H 0.7536 0.9395 0.2013 0.074 Uiso 1 1 calc R
C9 C 0.8238(2) 0.7992(8) 0.1856(2) 0.0562(15) Uani 1 1 d .
H9A H 0.8300 0.7621 0.2218 0.067 Uiso 1 1 calc R
C10 C 0.8604(2) 0.7491(7) 0.1443(2) 0.0468(13) Uani 1 1 d .
H10A H 0.8916 0.6798 0.1529 0.056 Uiso 1 1 calc R
Br2 Br 0.68860(2) 0.52361(8) 0.32548(2) 0.04776(18) Uani 1 1 d .
O2 O 0.71421(14) 0.3368(5) 0.43712(14) 0.0459(9) Uani 1 1 d .
N5 N 0.80180(16) 0.5285(5) 0.33507(15) 0.0332(9) Uani 1 1 d .
N6 N 0.85215(15) 0.5052(5) 0.36131(15) 0.0322(9) Uani 1 1 d .
N7 N 0.80910(16) 0.3811(5) 0.44030(16) 0.0340(9) Uani 1 1 d .
N8 N 0.90389(17) 0.4297(5) 0.43906(17) 0.0412(10) Uani 1 1 d .
H8A H 0.9057 0.3871 0.4720 0.049 Uiso 1 1 calc R
H8B H 0.9341 0.4661 0.4229 0.049 Uiso 1 1 calc R
C11 C 0.7577(2) 0.3933(6) 0.41587(19) 0.0324(11) Uani 1 1 d .
C12 C 0.75776(19) 0.4788(6) 0.3609(2) 0.0322(10) Uani 1 1 d .
C13 C 0.8544(2) 0.4395(5) 0.4132(2) 0.0324(11) Uani 1 1 d .
C14 C 0.90099(19) 0.5406(6) 0.32477(19) 0.0354(11) Uani 1 1 d .
H14A H 0.9337 0.5680 0.3473 0.042 Uiso 1 1 calc R
H14B H 0.8929 0.6434 0.3021 0.042 Uiso 1 1 calc R
C15 C 0.91475(19) 0.3868(6) 0.2878(2) 0.0351(11) Uani 1 1 d .
C16 C 0.9547(2) 0.2649(7) 0.3019(2) 0.0503(14) Uani 1 1 d .
H16A H 0.9738 0.2765 0.3353 0.060 Uiso 1 1 calc R
C17 C 0.9671(3) 0.1252(9) 0.2676(3) 0.0720(19) Uani 1 1 d .
H17A H 0.9944 0.0430 0.2779 0.086 Uiso 1 1 calc R
C18 C 0.9397(3) 0.1070(9) 0.2187(3) 0.074(2) Uani 1 1 d .
H18A H 0.9487 0.0138 0.1952 0.089 Uiso 1 1 calc R
C19 C 0.8987(3) 0.2265(9) 0.2040(3) 0.0677(18) Uani 1 1 d .
H19A H 0.8794 0.2135 0.1707 0.081 Uiso 1 1 calc R
C20 C 0.8859(2) 0.3662(7) 0.2388(2) 0.0483(14) Uani 1 1 d .
H20A H 0.8578 0.4464 0.2291 0.058 Uiso 1 1 calc R
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'
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
C2 N1 N2 116.6(4)
N1 N2 C3 120.8(4)
N1 N2 C4 114.8(4)
C3 N2 C4 124.3(4)
C3 N3 C1 119.8(4)
O1 C1 N3 122.6(4)
O1 C1 C2 123.0(4)
N3 C1 C2 114.3(4)
N1 C2 C1 125.7(4)
N1 C2 Br1 115.7(3)
C1 C2 Br1 118.6(3)
N4 C3 N3 118.3(4)
N4 C3 N2 119.0(4)
N3 C3 N2 122.7(4)
N2 C4 C5 113.3(4)
C10 C5 C6 118.3(5)
C10 C5 C4 122.3(4)
C6 C5 C4 119.3(5)
C7 C6 C5 120.7(5)
C6 C7 C8 120.6(6)
C7 C8 C9 119.4(6)
C8 C9 C10 119.9(5)
C5 C10 C9 121.0(5)
C12 N5 N6 116.8(4)
C13 N6 N5 121.0(4)
C13 N6 C14 126.1(4)
N5 N6 C14 112.5(4)
C13 N7 C11 119.1(4)
O2 C11 N7 123.2(4)
O2 C11 C12 121.9(4)
N7 C11 C12 114.9(4)
N5 C12 C11 124.8(4)
N5 C12 Br2 115.9(4)
C11 C12 Br2 119.2(3)
N8 C13 N7 117.4(4)
N8 C13 N6 119.5(4)
N7 C13 N6 123.1(4)
N6 C14 C15 112.6(4)
C16 C15 C20 118.9(5)
C16 C15 C14 121.7(5)
C20 C15 C14 119.5(5)
C15 C16 C17 121.1(6)
C18 C17 C16 120.1(6)
C17 C18 C19 119.8(6)
C18 C19 C20 120.0(6)
C15 C20 C19 120.1(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.883(4)
O1 C1 1.220(5)
N1 C2 1.277(5)
N1 N2 1.363(5)
N2 C3 1.364(6)
N2 C4 1.467(6)
N3 C3 1.329(5)
N3 C1 1.363(6)
N4 C3 1.323(5)
C1 C2 1.466(6)
C4 C5 1.512(6)
C5 C10 1.368(6)
C5 C6 1.378(7)
C6 C7 1.367(8)
C7 C8 1.360(8)
C8 C9 1.371(8)
C9 C10 1.376(7)
Br2 C12 1.879(5)
O2 C11 1.228(5)
N5 C12 1.273(6)
N5 N6 1.362(5)
N6 C13 1.350(6)
N6 C14 1.480(5)
N7 C13 1.333(6)
N7 C11 1.356(6)
N8 C13 1.330(6)
C11 C12 1.477(7)
C14 C15 1.502(6)
C15 C16 1.363(7)
C15 C20 1.377(7)
C16 C17 1.375(8)
C17 C18 1.354(9)
C18 C19 1.374(9)
C19 C20 1.383(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168302968
