#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/26/2222693.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_2222693
loop_
_publ_author_name
'Zhu, Xiaohui'
_publ_section_title
;
 5-Bromo-N³-phenylpyrazine-2,3-diamine
;
_journal_coeditor_code           GK2218
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1968
_journal_paper_doi               10.1107/S1600536809028554
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H9 Br N4'
_chemical_formula_moiety         'C10 H9 Br N4'
_chemical_formula_sum            'C10 H9 Br N4'
_chemical_formula_weight         265.12
_chemical_name_systematic
;
5-Bromo-N³-phenylpyrazine-2,3-diamine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 91.307(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4834(8)
_cell_length_b                   15.4038(17)
_cell_length_c                   9.2079(10)
_cell_measurement_reflns_used    2474
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.58
_cell_volume                     1061.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω'
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5494
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.845
_exptl_absorpt_correction_T_max  0.6998
_exptl_absorpt_correction_T_min  0.5963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.326
_refine_ls_extinction_coef       0.0241(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0247
_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)+(0.025P)²+0.6504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0589
_reflns_number_gt                1555
_reflns_number_total             1871
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2218.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222693
_cod_database_fobs_code          2222693
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
Br Br1 -0.05901(4) 0.351301(18) 1.09071(3) 0.05020(14) Uani d . 1 . .
N N1 0.1466(3) 0.39455(14) 0.4791(2) 0.0455(5) Uani d . 1 . .
H H1A 0.1000 0.4388 0.4334 0.046(8) Uiso d R 1 . .
H H1B 0.2400 0.3676 0.4472 0.075(11) Uiso d R 1 . .
N N2 -0.0254(3) 0.43567(13) 0.6710(2) 0.0404(5) Uani d . 1 . .
N N3 0.1484(2) 0.31467(12) 0.84959(19) 0.0319(4) Uani d . 1 . .
N N4 0.3193(3) 0.27272(13) 0.6497(2) 0.0420(5) Uani d . 1 . .
H H4 0.2980 0.2595 0.5591 0.063(9) Uiso d R 1 . .
C C1 0.1017(3) 0.38587(14) 0.6195(2) 0.0317(5) Uani d . 1 . .
C C2 0.1899(3) 0.32331(14) 0.7117(2) 0.0302(5) Uani d . 1 . .
C C3 0.0152(3) 0.36556(15) 0.8955(2) 0.0343(5) Uani d . 1 . .
C C4 -0.0699(3) 0.42447(16) 0.8104(3) 0.0423(6) Uani d . 1 . .
H H4A -0.1608 0.4579 0.8488 0.051 Uiso calc R 1 . .
C C5 0.4259(3) 0.21097(15) 0.7267(2) 0.0365(6) Uani d . 1 . .
C C6 0.4269(4) 0.12553(16) 0.6809(3) 0.0446(6) Uani d . 1 . .
H H6 0.3565 0.1084 0.6014 0.054 Uiso calc R 1 . .
C C7 0.5329(4) 0.06590(19) 0.7538(3) 0.0564(8) Uani d . 1 . .
H H7 0.5338 0.0084 0.7229 0.068 Uiso calc R 1 . .
C C8 0.6367(4) 0.0902(2) 0.8710(3) 0.0613(8) Uani d . 1 . .
H H8 0.7056 0.0491 0.9209 0.074 Uiso calc R 1 . .
C C9 0.6390(4) 0.1748(2) 0.9145(3) 0.0589(8) Uani d . 1 . .
H H9 0.7108 0.1916 0.9934 0.071 Uiso calc R 1 . .
C C10 0.5348(3) 0.23602(18) 0.8419(3) 0.0468(6) Uani d . 1 . .
H H10 0.5383 0.2938 0.8709 0.056 Uiso calc R 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 H1A . . 115.8 ?
C1 N1 H1B . . 119.8 ?
H1A N1 H1B . . 121.8 ?
C1 N2 C4 . . 117.7(2) ?
C2 N3 C3 . . 115.85(19) ?
C2 N4 C5 . . 124.36(19) ?
C2 N4 H4 . . 114.5 ?
C5 N4 H4 . . 114.3 ?
N2 C1 N1 . . 119.0(2) ?
N2 C1 C2 . . 120.2(2) ?
N1 C1 C2 . . 120.8(2) ?
N3 C2 N4 . . 121.6(2) ?
N3 C2 C1 . . 121.5(2) ?
N4 C2 C1 . . 116.92(19) ?
N3 C3 C4 . . 123.6(2) ?
N3 C3 Br1 . . 117.62(16) ?
C4 C3 Br1 . . 118.81(18) ?
N2 C4 C3 . . 121.2(2) ?
N2 C4 H4A . . 119.4 ?
C3 C4 H4A . . 119.4 ?
C10 C5 C6 . . 119.6(2) ?
C10 C5 N4 . . 120.8(2) ?
C6 C5 N4 . . 119.5(2) ?
C7 C6 C5 . . 119.5(3) ?
C7 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
C8 C7 C6 . . 120.8(3) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C9 C8 C7 . . 119.7(3) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C8 C9 C10 . . 120.4(3) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C5 C10 C9 . . 119.8(3) ?
C5 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
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
Br1 C3 . 1.906(2) ?
N1 C1 . 1.349(3) ?
N1 H1A . 0.8699 ?
N1 H1B . 0.8700 ?
N2 C1 . 1.319(3) ?
N2 C4 . 1.344(3) ?
N3 C2 . 1.320(3) ?
N3 C3 . 1.344(3) ?
N4 C2 . 1.377(3) ?
N4 C5 . 1.420(3) ?
N4 H4 . 0.8700 ?
C1 C2 . 1.436(3) ?
C3 C4 . 1.349(3) ?
C4 H4A . 0.9300 ?
C5 C10 . 1.378(4) ?
C5 C6 . 1.382(3) ?
C6 C7 . 1.378(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.368(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.364(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.385(4) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
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
N1 H1B Cg1 4_565 0.86 2.63 3.436(3) 157
N1 H1A N2 3_566 0.86 2.22 3.084(3) 169
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N2 C1 N1 . . . . 178.7(2) ?
C4 N2 C1 C2 . . . . -1.1(3) ?
C3 N3 C2 N4 . . . . -177.5(2) ?
C3 N3 C2 C1 . . . . 2.3(3) ?
C5 N4 C2 N3 . . . . -3.5(4) ?
C5 N4 C2 C1 . . . . 176.6(2) ?
N2 C1 C2 N3 . . . . -0.9(3) ?
N1 C1 C2 N3 . . . . 179.4(2) ?
N2 C1 C2 N4 . . . . 179.0(2) ?
N1 C1 C2 N4 . . . . -0.8(3) ?
C2 N3 C3 C4 . . . . -2.1(3) ?
C2 N3 C3 Br1 . . . . 176.66(16) ?
C1 N2 C4 C3 . . . . 1.3(4) ?
N3 C3 C4 N2 . . . . 0.3(4) ?
Br1 C3 C4 N2 . . . . -178.49(19) ?
C2 N4 C5 C10 . . . . -59.7(3) ?
C2 N4 C5 C6 . . . . 123.5(3) ?
C10 C5 C6 C7 . . . . 1.9(4) ?
N4 C5 C6 C7 . . . . 178.8(2) ?
C5 C6 C7 C8 . . . . 0.1(4) ?
C6 C7 C8 C9 . . . . -1.6(5) ?
C7 C8 C9 C10 . . . . 0.9(5) ?
C6 C5 C10 C9 . . . . -2.6(4) ?
N4 C5 C10 C9 . . . . -179.4(2) ?
C8 C9 C10 C5 . . . . 1.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742921
