#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/62/7206219.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_7206219
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 H5 Cl2 N3, C4 H1 Br2 N O2'
_chemical_formula_sum            'C9 H6 Br2 Cl2 N4 O2'
_chemical_formula_weight         432.90
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.225(12)
_cell_angle_beta                 98.246(11)
_cell_angle_gamma                95.329(11)
_cell_formula_units_Z            2
_cell_length_a                   6.9498(8)
_cell_length_b                   8.5107(11)
_cell_length_c                   11.2025(12)
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      32.23
_cell_measurement_theta_min      2.98
_cell_volume                     640.56(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement
'SHELXL-97 (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 0.992
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12200
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.81
_diffrn_reflns_theta_min         2.45
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    6.746
_exptl_absorpt_correction_T_max  0.3836
_exptl_absorpt_correction_T_min  0.2712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    2.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       table
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4151
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0233
_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)+(0.0260P)²+0.1672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_refine_ls_wR_factor_ref         0.0546
_reflns_number_gt                3477
_reflns_number_total             4151
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1ce05166k.txt
_cod_data_source_block           cz17
_cod_original_cell_volume        640.56(13)
_cod_database_code               7206219
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.84598(6) 0.03186(5) 0.10171(4) 0.01568(9) Uani 1 1 d . . .
Cl2 Cl 0.14952(6) -0.27199(5) 0.14641(4) 0.01511(9) Uani 1 1 d . . .
N1 N 0.5103(2) 0.08865(18) 0.36195(13) 0.0132(3) Uani 1 1 d . . .
N2 N 0.8157(2) 0.2163(2) 0.35238(17) 0.0178(3) Uani 1 1 d D . .
H2A H 0.811(3) 0.279(2) 0.4178(18) 0.016(6) Uiso 1 1 d D . .
H2B H 0.904(4) 0.225(3) 0.309(2) 0.042(8) Uiso 1 1 d D . .
N3 N 0.2074(2) -0.0321(2) 0.38187(17) 0.0173(3) Uani 1 1 d D . .
H3A H 0.214(3) 0.036(2) 0.4465(18) 0.014(6) Uiso 1 1 d D . .
H3B H 0.108(3) -0.097(3) 0.349(2) 0.030(7) Uiso 1 1 d D . .
C1 C 0.6609(2) 0.1044(2) 0.29946(17) 0.0131(3) Uani 1 1 d . . .
C2 C 0.6553(2) 0.0071(2) 0.18331(16) 0.0127(3) Uani 1 1 d . . .
C3 C 0.4985(2) -0.1087(2) 0.13462(17) 0.0129(3) Uani 1 1 d . . .
H3 H 0.492(3) -0.176(3) 0.056(2) 0.016(5) Uiso 1 1 d . . .
C4 C 0.3483(2) -0.1252(2) 0.20120(17) 0.0125(3) Uani 1 1 d . . .
C5 C 0.3544(2) -0.0226(2) 0.31491(16) 0.0125(3) Uani 1 1 d . . .
Br1 Br 0.74777(2) 0.70166(2) 0.839229(18) 0.01704(5) Uani 1 1 d . . .
Br2 Br 0.27004(3) 0.51793(2) 0.869352(18) 0.01820(5) Uani 1 1 d . . .
O1 O 0.80079(19) 0.47170(17) 0.58145(13) 0.0187(3) Uani 1 1 d . . .
O2 O 0.20426(18) 0.22939(16) 0.61834(13) 0.0169(3) Uani 1 1 d . . .
N4 N 0.4994(2) 0.32332(19) 0.56916(15) 0.0143(3) Uani 1 1 d . . .
H4 H 0.503(3) 0.247(3) 0.503(2) 0.027(6) Uiso 1 1 d . . .
C6 C 0.6508(3) 0.4437(2) 0.62134(17) 0.0140(3) Uani 1 1 d . . .
C7 C 0.5898(2) 0.5319(2) 0.73533(17) 0.0133(3) Uani 1 1 d . . .
C8 C 0.4146(2) 0.4626(2) 0.74581(17) 0.0137(3) Uani 1 1 d . . .
C9 C 0.3512(2) 0.3238(2) 0.63943(17) 0.0137(3) 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'
Cl Cl 0.1484 0.1585 '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
C5 N1 C1 120.43(16) . . ?
C1 N2 H2A 120.2(16) . . ?
C1 N2 H2B 115(2) . . ?
H2A N2 H2B 124(2) . . ?
C5 N3 H3A 118.2(15) . . ?
C5 N3 H3B 116.2(18) . . ?
H3A N3 H3B 125(2) . . ?
N1 C1 N2 117.85(17) . . ?
N1 C1 C2 120.38(16) . . ?
N2 C1 C2 121.76(16) . . ?
C3 C2 C1 119.97(16) . . ?
C3 C2 Cl1 119.90(14) . . ?
C1 C2 Cl1 120.13(13) . . ?
C2 C3 C4 118.67(17) . . ?
C2 C3 H3 121.2(13) . . ?
C4 C3 H3 120.2(13) . . ?
C3 C4 C5 120.13(16) . . ?
C3 C4 Cl2 120.86(15) . . ?
C5 C4 Cl2 119.02(13) . . ?
N1 C5 N3 117.66(17) . . ?
N1 C5 C4 120.35(15) . . ?
N3 C5 C4 121.98(16) . . ?
C6 N4 C9 111.42(16) . . ?
C6 N4 H4 124.3(16) . . ?
C9 N4 H4 123.9(16) . . ?
O1 C6 N4 126.43(18) . . ?
O1 C6 C7 127.64(17) . . ?
N4 C6 C7 105.92(15) . . ?
C8 C7 C6 108.49(16) . . ?
C8 C7 Br1 129.23(15) . . ?
C6 C7 Br1 122.25(12) . . ?
C7 C8 C9 108.47(15) . . ?
C7 C8 Br2 127.61(15) . . ?
C9 C8 Br2 123.90(12) . . ?
O2 C9 N4 125.90(18) . . ?
O2 C9 C8 128.41(16) . . ?
N4 C9 C8 105.68(14) . . ?
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
Cl1 C2 1.7323(17) . ?
Cl2 C4 1.7350(18) . ?
N1 C5 1.348(2) . ?
N1 C1 1.349(2) . ?
N2 C1 1.357(2) . ?
N2 H2A 0.832(19) . ?
N2 H2B 0.84(2) . ?
N3 C5 1.356(2) . ?
N3 H3A 0.836(19) . ?
N3 H3B 0.84(2) . ?
C1 C2 1.406(3) . ?
C2 C3 1.377(2) . ?
C3 C4 1.378(2) . ?
C3 H3 0.95(2) . ?
C4 C5 1.403(3) . ?
Br1 C7 1.8410(18) . ?
Br2 C8 1.8446(18) . ?
O1 C6 1.212(2) . ?
O2 C9 1.206(2) . ?
N4 C6 1.382(2) . ?
N4 C9 1.383(2) . ?
N4 H4 0.90(3) . ?
C6 C7 1.499(3) . ?
C7 C8 1.333(2) . ?
C8 C9 1.504(3) . ?
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
C5 N1 C1 N2 -178.75(16) . . . . ?
C5 N1 C1 C2 1.3(2) . . . . ?
N1 C1 C2 C3 -2.2(2) . . . . ?
N2 C1 C2 C3 177.79(16) . . . . ?
N1 C1 C2 Cl1 178.19(13) . . . . ?
N2 C1 C2 Cl1 -1.8(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
Cl1 C2 C3 C4 -179.62(13) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C2 C3 C4 Cl2 -178.51(13) . . . . ?
C1 N1 C5 N3 -179.74(16) . . . . ?
C1 N1 C5 C4 1.1(2) . . . . ?
C3 C4 C5 N1 -2.5(2) . . . . ?
Cl2 C4 C5 N1 177.52(12) . . . . ?
C3 C4 C5 N3 178.35(17) . . . . ?
Cl2 C4 C5 N3 -1.6(2) . . . . ?
C9 N4 C6 O1 179.26(18) . . . . ?
C9 N4 C6 C7 -1.33(19) . . . . ?
O1 C6 C7 C8 179.91(18) . . . . ?
N4 C6 C7 C8 0.52(19) . . . . ?
O1 C6 C7 Br1 -2.0(3) . . . . ?
N4 C6 C7 Br1 178.60(12) . . . . ?
C6 C7 C8 C9 0.41(19) . . . . ?
Br1 C7 C8 C9 -177.49(12) . . . . ?
C6 C7 C8 Br2 178.85(12) . . . . ?
Br1 C7 C8 Br2 1.0(3) . . . . ?
C6 N4 C9 O2 -177.48(17) . . . . ?
C6 N4 C9 C8 1.56(18) . . . . ?
C7 C8 C9 O2 177.81(18) . . . . ?
Br2 C8 C9 O2 -0.7(3) . . . . ?
C7 C8 C9 N4 -1.20(19) . . . . ?
Br2 C8 C9 N4 -179.71(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653785
