#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/83/2228357.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_2228357
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Yeap, Chin Sing'
'Shetty, Shobhitha'
'Kalluraya, Balakrishna'
_publ_section_title
;
 2,3-Dibromo-1-(4-chlorophenyl)-3-(5-nitro-2-furyl)propan-1-one
;
_journal_coeditor_code           HB5734
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3220
_journal_paper_doi               10.1107/S1600536810046829
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H8 Br2 Cl N O4'
_chemical_formula_moiety         'C13 H8 Br2 Cl N O4'
_chemical_formula_sum            'C13 H8 Br2 Cl N O4'
_chemical_formula_weight         437.47
_chemical_name_systematic
;
2,3-Dibromo-1-(4-chlorophenyl)-3-(5-nitro-2-furyl)propan-1-one
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.731(2)
_cell_angle_beta                 107.000(2)
_cell_angle_gamma                114.299(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4932(11)
_cell_length_b                   9.4501(12)
_cell_length_c                   10.5665(14)
_cell_measurement_reflns_used    6344
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.76
_cell_volume                     725.32(16)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII DUO 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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0306
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13696
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.786
_exptl_absorpt_correction_T_max  0.5872
_exptl_absorpt_correction_T_min  0.2971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.003
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.411
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.7632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0642
_reflns_number_gt                3398
_reflns_number_total             3856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb5734.cif
_cod_data_source_block           I
_cod_database_code               2228357
_cod_database_fobs_code          2228357
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 Br1A 0.6289(7) 0.5168(5) 0.7250(5) 0.0356(5) Uani d P 0.512(11) A 1
Br Br2A 0.3194(8) 0.1148(6) 0.9250(8) 0.0268(7) Uani d P 0.512(11) A 1
Br Br1B 0.3164(8) 0.1124(6) 0.9164(8) 0.0282(9) Uani d P 0.488(11) A 2
Br Br2B 0.5885(6) 0.5025(6) 0.7004(5) 0.0321(5) Uani d P 0.488(11) A 2
Cl Cl1 -0.35654(9) 0.23719(8) 0.24802(6) 0.02977(14) Uani d . 1 . .
O O1 0.2656(3) 0.4225(2) 0.86289(18) 0.0295(4) Uani d . 1 A .
O O2 0.6347(3) 0.1530(2) 0.76863(18) 0.0345(5) Uani d . 1 A .
O O3 0.8567(3) -0.0787(3) 0.7618(2) 0.0470(6) Uani d . 1 . .
O O4 0.6542(3) -0.0476(3) 0.5983(2) 0.0393(5) Uani d . 1 . .
N N1 0.7574(3) -0.0148(3) 0.7148(2) 0.0300(5) Uani d . 1 . .
C C1 -0.0395(3) 0.3544(3) 0.6339(2) 0.0249(5) Uani d . 1 . .
H H1A -0.0353 0.4008 0.7151 0.030 Uiso calc R 1 . .
C C2 -0.1827(3) 0.3272(3) 0.5175(2) 0.0245(5) Uani d . 1 . .
H H2A -0.2771 0.3520 0.5201 0.029 Uiso calc R 1 . .
C C3 -0.1840(3) 0.2625(3) 0.3966(2) 0.0239(5) Uani d . 1 . .
C C4 -0.0475(4) 0.2207(3) 0.3908(3) 0.0331(6) Uani d . 1 . .
H H4A -0.0507 0.1768 0.3089 0.040 Uiso calc R 1 . .
C C5 0.0930(4) 0.2451(4) 0.5083(3) 0.0370(7) Uani d . 1 . .
H H5A 0.1844 0.2161 0.5056 0.044 Uiso calc R 1 . .
C C6 0.0998(3) 0.3129(3) 0.6312(3) 0.0282(5) Uani d . 1 A .
C C7 0.2512(4) 0.3473(3) 0.7606(3) 0.0350(6) Uani d . 1 . .
C C8A 0.4124(8) 0.3173(8) 0.7467(6) 0.0243(15) Uani d P 0.512(11) A 1
H H8AA 0.3686 0.2261 0.6753 0.029 Uiso calc PR 0.512(11) A 1
C C8B 0.3687(8) 0.2509(8) 0.7864(6) 0.0206(14) Uani d P 0.488(11) A 2
H H8BA 0.3450 0.1875 0.7008 0.025 Uiso calc PR 0.488(11) A 2
C C9A 0.5118(8) 0.2949(8) 0.8801(5) 0.0231(16) Uani d P 0.512(11) A 1
H H9AA 0.5574 0.3905 0.9473 0.028 Uiso calc PR 0.512(11) A 1
C C9B 0.5707(8) 0.3651(8) 0.8459(6) 0.0217(15) Uani d P 0.488(11) A 2
H H9BA 0.5934 0.4294 0.9306 0.026 Uiso calc PR 0.488(11) A 2
C C10 0.6760(4) 0.2677(4) 0.8747(3) 0.0405(7) Uani d . 1 . .
C C11 0.8308(4) 0.2911(3) 0.9747(3) 0.0291(5) Uani d . 1 A .
H H11A 0.8863 0.3628 1.0561 0.035 Uiso calc R 1 . .
C C12 0.8923(3) 0.1848(3) 0.9317(3) 0.0276(5) Uani d . 1 . .
H H12A 0.9958 0.1724 0.9780 0.033 Uiso calc R 1 A .
C C13 0.7676(3) 0.1059(3) 0.8086(3) 0.0255(5) Uani d . 1 A .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 O2 C10 . . 104.5(2) ?
O4 N1 O3 . . 125.4(2) ?
O4 N1 C13 . . 119.5(2) ?
O3 N1 C13 . . 115.2(2) ?
C2 C1 C6 . . 120.7(2) ?
C2 C1 H1A . . 119.6 ?
C6 C1 H1A . . 119.6 ?
C1 C2 C3 . . 119.0(2) ?
C1 C2 H2A . . 120.5 ?
C3 C2 H2A . . 120.5 ?
C2 C3 C4 . . 121.5(2) ?
C2 C3 Cl1 . . 119.61(18) ?
C4 C3 Cl1 . . 118.85(19) ?
C5 C4 C3 . . 119.0(2) ?
C5 C4 H4A . . 120.5 ?
C3 C4 H4A . . 120.5 ?
C4 C5 C6 . . 120.7(2) ?
C4 C5 H5A . . 119.7 ?
C6 C5 H5A . . 119.7 ?
C5 C6 C1 . . 119.0(2) ?
C5 C6 C7 . . 123.3(2) ?
C1 C6 C7 . . 117.7(2) ?
O1 C7 C6 . . 122.1(2) ?
O1 C7 C8A . . 121.7(3) ?
C6 C7 C8A . . 114.6(3) ?
O1 C7 C8B . . 113.5(3) ?
C6 C7 C8B . . 122.3(3) ?
C8A C7 C8B . . 29.3(2) ?
C9A C8A C7 . . 108.0(5) ?
C9A C8A Br1A . . 99.1(4) ?
C7 C8A Br1A . . 114.4(4) ?
C9A C8A H8AA . . 111.6 ?
C7 C8A H8AA . . 111.6 ?
Br1A C8A H8AA . . 111.6 ?
C9B C8B C7 . . 109.4(5) ?
C9B C8B Br1B . . 106.2(5) ?
C7 C8B Br1B . . 112.8(4) ?
C9B C8B H8BA . . 109.5 ?
C7 C8B H8BA . . 109.5 ?
Br1B C8B H8BA . . 109.5 ?
C8A C9A C10 . . 110.9(5) ?
C8A C9A Br2A . . 105.0(5) ?
C10 C9A Br2A . . 114.6(4) ?
C8A C9A H9AA . . 108.7 ?
C10 C9A H9AA . . 108.7 ?
Br2A C9A H9AA . . 108.7 ?
C10 C9B C8B . . 107.3(5) ?
C10 C9B Br2B . . 122.0(4) ?
C8B C9B Br2B . . 99.1(4) ?
C10 C9B H9BA . . 109.2 ?
C8B C9B H9BA . . 109.2 ?
Br2B C9B H9BA . . 109.2 ?
C11 C10 O2 . . 110.9(2) ?
C11 C10 C9B . . 131.8(3) ?
O2 C10 C9B . . 115.6(3) ?
C11 C10 C9A . . 130.1(3) ?
O2 C10 C9A . . 114.4(3) ?
C9B C10 C9A . . 31.3(2) ?
C10 C11 C12 . . 106.6(2) ?
C10 C11 H11A . . 126.7 ?
C12 C11 H11A . . 126.7 ?
C13 C12 C11 . . 104.8(2) ?
C13 C12 H12A . . 127.6 ?
C11 C12 H12A . . 127.6 ?
O2 C13 C12 . . 113.2(2) ?
O2 C13 N1 . . 116.0(2) ?
C12 C13 N1 . . 130.8(2) ?
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
Br1A C8A . 2.102(8) ?
Br2A C9A . 2.008(9) ?
Br1B C8B . 1.962(11) ?
Br2B C9B . 2.059(8) ?
Cl1 C3 . 1.732(3) ?
O1 C7 . 1.211(3) ?
O2 C13 . 1.343(3) ?
O2 C10 . 1.377(3) ?
O3 N1 . 1.235(3) ?
O4 N1 . 1.220(3) ?
N1 C13 . 1.433(3) ?
C1 C2 . 1.377(3) ?
C1 C6 . 1.398(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.385(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.385(3) ?
C4 C5 . 1.378(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.395(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.488(4) ?
C7 C8A . 1.553(5) ?
C7 C8B . 1.586(6) ?
C8A C9A . 1.492(9) ?
C8A H8AA . 0.9800 ?
C8B C9B . 1.511(9) ?
C8B H8BA . 0.9800 ?
C9A C10 . 1.534(5) ?
C9A H9AA . 0.9800 ?
C9B C10 . 1.511(6) ?
C9B H9BA . 0.9800 ?
C10 C11 . 1.349(4) ?
C11 C12 . 1.420(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.349(4) ?
C12 H12A . 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
_geom_hbond_publ_flag
C9A H9AA O1 2_667 0.98 2.26 3.199(6) 160 yes
C4 H4A O3 2_656 0.93 2.46 3.184(4) 135 yes
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
C6 C1 C2 C3 . . . . -2.0(4) ?
C1 C2 C3 C4 . . . . 1.8(4) ?
C1 C2 C3 Cl1 . . . . -176.6(2) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
Cl1 C3 C4 C5 . . . . 178.1(2) ?
C3 C4 C5 C6 . . . . -0.9(5) ?
C4 C5 C6 C1 . . . . 0.7(5) ?
C4 C5 C6 C7 . . . . -177.8(3) ?
C2 C1 C6 C5 . . . . 0.8(4) ?
C2 C1 C6 C7 . . . . 179.4(3) ?
C5 C6 C7 O1 . . . . 171.3(3) ?
C1 C6 C7 O1 . . . . -7.3(5) ?
C5 C6 C7 C8A . . . . 5.8(5) ?
C1 C6 C7 C8A . . . . -172.8(4) ?
C5 C6 C7 C8B . . . . -26.5(6) ?
C1 C6 C7 C8B . . . . 154.9(4) ?
O1 C7 C8A C9A . . . . 36.2(7) ?
C6 C7 C8A C9A . . . . -158.2(4) ?
C8B C7 C8A C9A . . . . -45.6(6) ?
O1 C7 C8A Br1A . . . . -73.0(6) ?
C6 C7 C8A Br1A . . . . 92.5(4) ?
C8B C7 C8A Br1A . . . . -154.8(7) ?
O1 C7 C8B C9B . . . . -63.8(6) ?
C6 C7 C8B C9B . . . . 132.7(4) ?
C8A C7 C8B C9B . . . . 49.6(6) ?
O1 C7 C8B Br1B . . . . 54.2(5) ?
C6 C7 C8B Br1B . . . . -109.4(4) ?
C8A C7 C8B Br1B . . . . 167.5(7) ?
C7 C8A C9A C10 . . . . -178.9(4) ?
Br1A C8A C9A C10 . . . . -59.4(5) ?
C7 C8A C9A Br2A . . . . 56.7(5) ?
Br1A C8A C9A Br2A . . . . 176.2(3) ?
C7 C8B C9B C10 . . . . 177.3(3) ?
Br1B C8B C9B C10 . . . . 55.3(5) ?
C7 C8B C9B Br2B . . . . -54.9(5) ?
Br1B C8B C9B Br2B . . . . -176.9(3) ?
C13 O2 C10 C11 . . . . 1.0(4) ?
C13 O2 C10 C9B . . . . 168.0(4) ?
C13 O2 C10 C9A . . . . -157.4(4) ?
C8B C9B C10 C11 . . . . -144.5(5) ?
Br2B C9B C10 C11 . . . . 102.5(5) ?
C8B C9B C10 O2 . . . . 51.9(6) ?
Br2B C9B C10 O2 . . . . -61.1(6) ?
C8B C9B C10 C9A . . . . -43.5(6) ?
Br2B C9B C10 C9A . . . . -156.5(8) ?
C8A C9A C10 C11 . . . . 156.7(5) ?
Br2A C9A C10 C11 . . . . -84.6(5) ?
C8A C9A C10 O2 . . . . -50.1(7) ?
Br2A C9A C10 O2 . . . . 68.6(5) ?
C8A C9A C10 C9B . . . . 49.6(6) ?
Br2A C9A C10 C9B . . . . 168.2(7) ?
O2 C10 C11 C12 . . . . -0.5(4) ?
C9B C10 C11 C12 . . . . -164.7(5) ?
C9A C10 C11 C12 . . . . 153.5(5) ?
C10 C11 C12 C13 . . . . -0.2(3) ?
C10 O2 C13 C12 . . . . -1.1(3) ?
C10 O2 C13 N1 . . . . -179.8(3) ?
C11 C12 C13 O2 . . . . 0.9(3) ?
C11 C12 C13 N1 . . . . 179.3(3) ?
O4 N1 C13 O2 . . . . 13.2(4) ?
O3 N1 C13 O2 . . . . -166.3(2) ?
O4 N1 C13 C12 . . . . -165.2(3) ?
O3 N1 C13 C12 . . . . 15.3(4) ?
