#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/62/7206223.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_7206223
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 H Cl2 N O2'
_chemical_formula_sum            'C9 H6 Cl4 N4 O2'
_chemical_formula_weight         343.98
_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                101.979(11)
_cell_angle_beta                 101.519(11)
_cell_angle_gamma                97.213(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1818(6)
_cell_length_b                   7.8344(7)
_cell_length_c                   11.6453(15)
_cell_measurement_reflns_used    4665
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      34.10
_cell_measurement_theta_min      2.70
_cell_volume                     618.44(12)
_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, G. M. (2008). Acta Cryst. A64, 112-122)'
_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      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker, APEX 2000, CCD area detector'
_diffrn_measurement_method       'ω and φ 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  0.0887
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10015
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         34.36
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.958
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       table
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0342
_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)+(0.0307P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                3871
_reflns_number_total             4801
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1ce05166k.txt
_cod_data_source_block           cz14lt
_cod_original_cell_volume        618.44(11)
_cod_database_code               7206223
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 0.14126(5) -0.27696(4) 0.12998(3) 0.01915(8) Uani 1 1 d . . .
Cl2 Cl 0.84661(5) 0.07390(4) 0.14271(3) 0.02078(8) Uani 1 1 d . . .
N1 N 0.50352(15) 0.12000(13) 0.37200(9) 0.0166(2) Uani 1 1 d . . .
N2 N 0.20640(18) -0.03131(17) 0.37419(11) 0.0212(2) Uani 1 1 d . . .
H2A H 0.212(3) 0.041(2) 0.4372(16) 0.032(5) Uiso 1 1 d . . .
H2B H 0.096(3) -0.094(3) 0.3405(18) 0.058(7) Uiso 1 1 d . . .
N3 N 0.80392(18) 0.27631(16) 0.38142(11) 0.0211(2) Uani 1 1 d . . .
H3A H 0.810(3) 0.323(2) 0.4471(17) 0.041(6) Uiso 1 1 d . . .
H3B H 0.915(3) 0.295(3) 0.3522(17) 0.047(6) Uiso 1 1 d . . .
C1 C 0.34867(18) -0.00836(16) 0.31600(11) 0.0153(2) Uani 1 1 d . . .
C2 C 0.34163(18) -0.11457(15) 0.20128(11) 0.0154(2) Uani 1 1 d . . .
C3 C 0.49288(19) -0.08973(16) 0.14666(11) 0.0156(2) Uani 1 1 d . . .
H3 H 0.489(3) -0.159(2) 0.0720(15) 0.031(5) Uiso 1 1 d . . .
C4 C 0.65135(18) 0.04023(16) 0.20619(11) 0.0156(2) Uani 1 1 d . . .
C5 C 0.65385(18) 0.14419(16) 0.32070(11) 0.0156(2) Uani 1 1 d . . .
Cl3 Cl 0.73834(5) 0.72247(4) 0.88489(3) 0.01855(8) Uani 1 1 d . . .
Cl4 Cl 0.28804(5) 0.50117(4) 0.87129(3) 0.02285(8) Uani 1 1 d . . .
O1 O 0.20696(15) 0.22914(13) 0.61509(9) 0.0211(2) Uani 1 1 d . . .
O2 O 0.80264(15) 0.52764(13) 0.62912(9) 0.0210(2) Uani 1 1 d . . .
N4 N 0.50177(16) 0.35318(14) 0.59035(10) 0.0169(2) Uani 1 1 d . . .
H4 H 0.503(3) 0.286(2) 0.5263(15) 0.031(5) Uiso 1 1 d . . .
C6 C 0.35584(19) 0.33525(16) 0.65022(11) 0.0164(2) Uani 1 1 d . . .
C7 C 0.42173(18) 0.47234(15) 0.76771(11) 0.0152(2) Uani 1 1 d . . .
C8 C 0.59661(18) 0.55841(15) 0.77228(11) 0.0150(2) Uani 1 1 d . . .
C9 C 0.65395(19) 0.48383(16) 0.65765(11) 0.0158(2) 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'
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 120.71(11) . . ?
C1 N2 H2A 117.9(13) . . ?
C1 N2 H2B 123.6(15) . . ?
H2A N2 H2B 116(2) . . ?
C5 N3 H3A 120.0(16) . . ?
C5 N3 H3B 121.3(12) . . ?
H3A N3 H3B 117.2(19) . . ?
N2 C1 N1 117.98(11) . . ?
N2 C1 C2 122.19(11) . . ?
N1 C1 C2 119.82(12) . . ?
C3 C2 C1 120.20(11) . . ?
C3 C2 Cl1 120.49(9) . . ?
C1 C2 Cl1 119.31(10) . . ?
C2 C3 C4 119.13(11) . . ?
C2 C3 H3 120.3(12) . . ?
C4 C3 H3 120.6(12) . . ?
C3 C4 C5 119.26(12) . . ?
C3 C4 Cl2 120.90(10) . . ?
C5 C4 Cl2 119.83(9) . . ?
N1 C5 N3 117.63(11) . . ?
N1 C5 C4 120.85(11) . . ?
N3 C5 C4 121.48(12) . . ?
C6 N4 C9 111.69(11) . . ?
C6 N4 H4 123.7(13) . . ?
C9 N4 H4 124.2(13) . . ?
O1 C6 N4 126.67(12) . . ?
O1 C6 C7 127.57(13) . . ?
N4 C6 C7 105.75(10) . . ?
C8 C7 C6 108.34(11) . . ?
C8 C7 Cl4 128.81(10) . . ?
C6 C7 Cl4 122.84(9) . . ?
C7 C8 C9 108.44(11) . . ?
C7 C8 Cl3 128.08(11) . . ?
C9 C8 Cl3 123.47(9) . . ?
O2 C9 N4 126.55(12) . . ?
O2 C9 C8 127.70(11) . . ?
N4 C9 C8 105.76(11) . . ?
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 1.7330(12) . ?
Cl2 C4 1.7276(13) . ?
N1 C5 1.3460(16) . ?
N1 C1 1.3530(15) . ?
N2 C1 1.3478(17) . ?
N2 H2A 0.818(18) . ?
N2 H2B 0.85(2) . ?
N3 C5 1.3582(16) . ?
N3 H3A 0.766(19) . ?
N3 H3B 0.94(2) . ?
C1 C2 1.4073(17) . ?
C2 C3 1.3772(18) . ?
C3 C4 1.3833(17) . ?
C3 H3 0.916(17) . ?
C4 C5 1.4063(17) . ?
Cl3 C8 1.6871(12) . ?
Cl4 C7 1.6827(13) . ?
O1 C6 1.2093(16) . ?
O2 C9 1.2106(16) . ?
N4 C6 1.3783(17) . ?
N4 C9 1.3786(16) . ?
N4 H4 0.820(17) . ?
C6 C7 1.5011(17) . ?
C7 C8 1.3345(17) . ?
C8 C9 1.4997(18) . ?
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 177.13(12) . . . . ?
C5 N1 C1 C2 -1.89(18) . . . . ?
N2 C1 C2 C3 -178.13(12) . . . . ?
N1 C1 C2 C3 0.84(19) . . . . ?
N2 C1 C2 Cl1 1.68(18) . . . . ?
N1 C1 C2 Cl1 -179.34(9) . . . . ?
C1 C2 C3 C4 0.21(19) . . . . ?
Cl1 C2 C3 C4 -179.60(9) . . . . ?
C2 C3 C4 C5 -0.25(18) . . . . ?
C2 C3 C4 Cl2 178.82(10) . . . . ?
C1 N1 C5 N3 179.51(12) . . . . ?
C1 N1 C5 C4 1.87(19) . . . . ?
C3 C4 C5 N1 -0.78(19) . . . . ?
Cl2 C4 C5 N1 -179.86(10) . . . . ?
C3 C4 C5 N3 -178.33(12) . . . . ?
Cl2 C4 C5 N3 2.59(18) . . . . ?
C9 N4 C6 O1 -178.11(14) . . . . ?
C9 N4 C6 C7 1.13(14) . . . . ?
O1 C6 C7 C8 178.19(14) . . . . ?
N4 C6 C7 C8 -1.04(14) . . . . ?
O1 C6 C7 Cl4 -1.2(2) . . . . ?
N4 C6 C7 Cl4 179.53(9) . . . . ?
C6 C7 C8 C9 0.57(14) . . . . ?
Cl4 C7 C8 C9 179.95(10) . . . . ?
C6 C7 C8 Cl3 -178.82(9) . . . . ?
Cl4 C7 C8 Cl3 0.6(2) . . . . ?
C6 N4 C9 O2 179.04(14) . . . . ?
C6 N4 C9 C8 -0.79(14) . . . . ?
C7 C8 C9 O2 -179.74(14) . . . . ?
Cl3 C8 C9 O2 -0.3(2) . . . . ?
C7 C8 C9 N4 0.09(14) . . . . ?
Cl3 C8 C9 N4 179.52(9) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653787
