#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/62/7206218.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_7206218
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         'C4 H Br2 N O2'
_chemical_formula_sum            'C4 H Br2 N O2'
_chemical_formula_weight         254.88
_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                 100.031(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2396(10)
_cell_length_b                   8.1042(8)
_cell_length_c                   7.8045(8)
_cell_measurement_reflns_used    4025
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      3.040
_cell_volume                     637.75(11)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.908
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7770
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    12.626
_exptl_absorpt_correction_T_max  0.2656
_exptl_absorpt_correction_T_min  0.1519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    2.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       table
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0243
_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)+(0.0223P)²+0.2314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0577
_reflns_number_gt                1397
_reflns_number_total             1775
_cod_data_source_file            c1ce05166k.txt
_cod_data_source_block           cz21
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7206218
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 0.45321(3) 0.43872(3) 0.22688(4) 0.05137(10) Uani 1 1 d . . .
Br2 Br 0.23262(3) 0.74996(3) -0.01357(4) 0.04719(10) Uani 1 1 d . . .
O2 O 0.01404(19) 0.4978(2) -0.2251(2) 0.0528(5) Uani 1 1 d . . .
O1 O 0.2797(2) 0.1113(2) 0.0813(3) 0.0514(5) Uani 1 1 d . . .
N1 N 0.1261(2) 0.2715(2) -0.0960(3) 0.0419(5) Uani 1 1 d . . .
H1 H 0.0746 0.1949 -0.1450 0.050 Uiso 1 1 calc R . .
C1 C 0.2387(3) 0.2437(3) 0.0249(3) 0.0371(5) Uani 1 1 d . . .
C2 C 0.2984(2) 0.4107(3) 0.0706(3) 0.0346(5) Uani 1 1 d . . .
C3 C 0.2199(2) 0.5234(3) -0.0175(3) 0.0341(5) Uani 1 1 d . . .
C4 C 0.1060(3) 0.4376(3) -0.1289(3) 0.0379(5) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.03884(17) 0.05716(17) 0.05157(18) -0.00087(12) -0.01031(13) -0.00047(13)
Br2 0.0558(2) 0.02833(12) 0.05375(18) 0.00141(10) -0.00071(14) -0.00207(10)
O2 0.0405(11) 0.0452(10) 0.0640(13) 0.0047(9) -0.0152(10) 0.0032(9)
O1 0.0519(12) 0.0318(8) 0.0675(13) 0.0044(8) 0.0018(10) 0.0054(8)
N1 0.0374(13) 0.0300(9) 0.0530(13) -0.0007(8) -0.0065(10) -0.0048(8)
C1 0.0353(14) 0.0321(11) 0.0427(14) 0.0007(9) 0.0036(11) 0.0030(9)
C2 0.0307(12) 0.0331(10) 0.0374(13) -0.0013(9) -0.0015(10) -0.0010(9)
C3 0.0324(14) 0.0277(10) 0.0408(13) -0.0004(8) 0.0022(11) -0.0001(9)
C4 0.0334(14) 0.0346(10) 0.0434(14) 0.0005(10) -0.0001(11) 0.0009(10)
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
C1 N1 C4 111.6(2) . . ?
O1 C1 N1 126.4(2) . . ?
O1 C1 C2 127.8(2) . . ?
N1 C1 C2 105.83(18) . . ?
C3 C2 C1 108.2(2) . . ?
C3 C2 Br1 129.29(18) . . ?
C1 C2 Br1 122.48(17) . . ?
C2 C3 C4 108.70(19) . . ?
C2 C3 Br2 130.1(2) . . ?
C4 C3 Br2 121.22(17) . . ?
O2 C4 N1 126.0(2) . . ?
O2 C4 C3 128.3(2) . . ?
N1 C4 C3 105.6(2) . . ?
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 C2 1.838(2) . ?
Br2 C3 1.840(2) . ?
O2 C4 1.201(3) . ?
O1 C1 1.207(3) . ?
N1 C1 1.376(3) . ?
N1 C4 1.378(3) . ?
C1 C2 1.503(3) . ?
C2 C3 1.327(3) . ?
C3 C4 1.499(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13641
