#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/62/7206220.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_7206220
loop_
_publ_author_name
'Pilati, Tullio'
'Cozzi, Franco'
_publ_section_title
;
 Structures of hydro-, chloro-, and bromo-substituted maleimides and
 2,6-diaminopyridines, and of some of their 1 : 1
 heterodimers
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              4549
_journal_paper_doi               10.1039/c1ce05166k
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C5 H8 N3 1+, C4 Br2 N O2 1-'
_chemical_formula_sum            'C9 H8 Br2 N4 O2'
_chemical_formula_weight         364.01
_chemical_name_systematic
;
?
;
_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                 97.809(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8217(6)
_cell_length_b                   22.432(3)
_cell_length_c                   13.711(2)
_cell_measurement_reflns_used    3693
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.62
_cell_measurement_theta_min      2.35
_cell_volume                     1164.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E.,
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006).
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXTL
_computing_structure_refinement
'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_solution
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L.,
Giacovazzo, C., Polidori, G. & Spagna, R. (2003).
J. Appl. Cryst. 36, 1103.)
;
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12949
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    6.956
_exptl_absorpt_correction_T_max  0.2661
_exptl_absorpt_correction_T_min  0.1935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.076
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       neeedle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.188
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                2306
_reflns_number_total             3047
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1ce05166k.txt
_cod_data_source_block           cz24
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7206220
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_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 0.81342(10) 0.292408(17) 0.67155(3) 0.02179(12) Uani 1 1 d . . .
Br2 Br 0.70588(10) 0.304444(17) 0.93691(3) 0.02207(12) Uani 1 1 d . . .
O1 O 0.5077(7) 0.42437(12) 0.60500(17) 0.0220(6) Uani 1 1 d . . .
O2 O 0.3146(7) 0.43421(12) 0.92359(17) 0.0214(6) Uani 1 1 d . . .
N4 N 0.3689(8) 0.44659(14) 0.7595(2) 0.0187(7) Uani 1 1 d . . .
C6 C 0.4997(10) 0.41175(17) 0.6919(3) 0.0178(8) Uani 1 1 d . . .
C7 C 0.6372(9) 0.35395(16) 0.7400(2) 0.0157(7) Uani 1 1 d . . .
C8 C 0.5910(9) 0.35798(16) 0.8346(2) 0.0157(7) Uani 1 1 d . . .
C9 C 0.4139(9) 0.41694(16) 0.8464(2) 0.0159(7) Uani 1 1 d . . .
N1 N 0.0444(8) 0.55691(14) 0.7296(2) 0.0140(6) Uani 1 1 d U . .
H1 H 0.129(10) 0.5239(19) 0.737(3) 0.015(3) Uiso 1 1 d U . .
N2 N 0.1854(9) 0.54986(15) 0.5729(2) 0.0195(7) Uani 1 1 d U . .
H2A H 0.289(11) 0.514(2) 0.584(3) 0.025(4) Uiso 1 1 d U . .
H2B H 0.234(11) 0.5618(19) 0.520(3) 0.027(4) Uiso 1 1 d U . .
N3 N -0.0634(9) 0.55361(15) 0.8912(2) 0.0222(7) Uani 1 1 d U . .
H3A H 0.035(11) 0.519(2) 0.892(3) 0.025(4) Uiso 1 1 d U . .
H3B H -0.156(11) 0.5683(19) 0.943(3) 0.026(4) Uiso 1 1 d U . .
C1 C 0.0443(10) 0.58209(16) 0.6400(2) 0.0156(7) Uani 1 1 d . . .
C2 C -0.0980(10) 0.63881(17) 0.6241(3) 0.0189(8) Uani 1 1 d . . .
H2 H -0.120(11) 0.654(2) 0.569(3) 0.025(12) Uiso 1 1 d . . .
C3 C -0.2327(10) 0.66672(18) 0.7004(3) 0.0193(8) Uani 1 1 d . . .
H3 H -0.325(11) 0.7019(17) 0.691(3) 0.019(11) Uiso 1 1 d . . .
C4 C -0.2277(10) 0.64102(18) 0.7914(3) 0.0185(8) Uani 1 1 d . . .
H4 H -0.314(10) 0.6583(19) 0.840(3) 0.022(11) Uiso 1 1 d . . .
C5 C -0.0828(10) 0.58451(16) 0.8066(2) 0.0164(7) Uani 1 1 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 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N4 C6 107.6(3) . . ?
O1 C6 N4 126.1(4) . . ?
O1 C6 C7 124.5(3) . . ?
N4 C6 C7 109.5(3) . . ?
C8 C7 C6 106.3(3) . . ?
C8 C7 Br1 130.5(3) . . ?
C6 C7 Br1 123.1(2) . . ?
C7 C8 C9 106.5(3) . . ?
C7 C8 Br2 129.9(3) . . ?
C9 C8 Br2 123.5(2) . . ?
O2 C9 N4 125.6(3) . . ?
O2 C9 C8 124.3(3) . . ?
N4 C9 C8 110.0(3) . . ?
C1 N1 C5 123.7(3) . . ?
C1 N1 H1 117(3) . . ?
C5 N1 H1 120(3) . . ?
C1 N2 H2A 125(3) . . ?
C1 N2 H2B 126(3) . . ?
H2A N2 H2B 107(4) . . ?
C5 N3 H3A 117(3) . . ?
C5 N3 H3B 121(3) . . ?
H3A N3 H3B 122(4) . . ?
N2 C1 N1 116.6(3) . . ?
N2 C1 C2 124.9(3) . . ?
N1 C1 C2 118.5(3) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120(3) . . ?
C1 C2 H2 121(3) . . ?
C4 C3 C2 122.6(4) . . ?
C4 C3 H3 118(3) . . ?
C2 C3 H3 119(3) . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 123(3) . . ?
C5 C4 H4 118(3) . . ?
N3 C5 N1 116.6(3) . . ?
N3 C5 C4 125.1(3) . . ?
N1 C5 C4 118.3(3) . . ?
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 C7 1.847(4) . ?
Br2 C8 1.853(3) . ?
O1 C6 1.229(4) . ?
O2 C9 1.234(4) . ?
N4 C9 1.355(4) . ?
N4 C6 1.359(4) . ?
C6 C7 1.516(5) . ?
C7 C8 1.336(5) . ?
C8 C9 1.504(5) . ?
N1 C1 1.352(4) . ?
N1 C5 1.369(4) . ?
N1 H1 0.81(4) . ?
N2 C1 1.340(5) . ?
N2 H2A 0.89(4) . ?
N2 H2B 0.82(4) . ?
N3 C5 1.345(5) . ?
N3 H3A 0.86(5) . ?
N3 H3B 0.90(4) . ?
C1 C2 1.389(5) . ?
C2 C3 1.378(5) . ?
C2 H2 0.83(4) . ?
C3 C4 1.372(5) . ?
C3 H3 0.87(4) . ?
C4 C5 1.388(5) . ?
C4 H4 0.88(4) . ?
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
C9 N4 C6 O1 -179.2(4) . . . . ?
C9 N4 C6 C7 0.8(4) . . . . ?
O1 C6 C7 C8 178.2(4) . . . . ?
N4 C6 C7 C8 -1.8(4) . . . . ?
O1 C6 C7 Br1 -3.7(5) . . . . ?
N4 C6 C7 Br1 176.3(2) . . . . ?
C6 C7 C8 C9 1.9(4) . . . . ?
Br1 C7 C8 C9 -176.0(3) . . . . ?
C6 C7 C8 Br2 -178.8(3) . . . . ?
Br1 C7 C8 Br2 3.3(6) . . . . ?
C6 N4 C9 O2 -177.2(4) . . . . ?
C6 N4 C9 C8 0.4(4) . . . . ?
C7 C8 C9 O2 176.1(4) . . . . ?
Br2 C8 C9 O2 -3.3(5) . . . . ?
C7 C8 C9 N4 -1.5(4) . . . . ?
Br2 C8 C9 N4 179.1(3) . . . . ?
C5 N1 C1 N2 178.6(3) . . . . ?
C5 N1 C1 C2 -1.1(5) . . . . ?
N2 C1 C2 C3 -179.7(4) . . . . ?
N1 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C1 N1 C5 N3 -179.8(3) . . . . ?
C1 N1 C5 C4 1.5(5) . . . . ?
C3 C4 C5 N3 -179.2(4) . . . . ?
C3 C4 C5 N1 -0.7(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653786
