#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/03/2210389.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210389
loop_
_publ_author_name
'Fischer, Andreas'
_publ_section_title
;
 2-Bromofumaric acid
;
_journal_coeditor_code           SJ2110
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4190
_journal_page_last               o4191
_journal_paper_doi               10.1107/S160053680603368X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C4 H3 Br O4'
_chemical_formula_moiety         'C4 H3 Br O4'
_chemical_formula_sum            'C4 H3 Br O4'
_chemical_formula_weight         194.973
_chemical_name_systematic
;
2-Bromofumaric acid
;
_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_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                69.572(4)
_cell_angle_beta                 70.383(3)
_cell_angle_gamma                79.963(4)
_cell_formula_units_Z            4
_cell_length_a                   7.8290(4)
_cell_length_b                   8.3791(4)
_cell_length_c                   10.2443(3)
_cell_measurement_reflns_used    60
_cell_measurement_temperature    299
_cell_measurement_theta_max      22.0
_cell_measurement_theta_min      4.3
_cell_volume                     591.97(5)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg, 1992)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'MAXUS (Mackay et al.,  1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_sigmaI/netI    0.044
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11936
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         4.5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.877
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(Herrendorf & Bärnighausen, 1997)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    2.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0231P)²+0.495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0722
_reflns_number_gt                1821
_reflns_number_total             2701
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2110.cif
_cod_data_source_block           I
_cod_database_code               2210389
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
Br Br2 0.65543(6) 0.05029(6) 0.59519(4) 0.06076(16) Uani d . 1
Br Br1 0.56894(5) 0.50250(5) 0.68940(4) 0.05132(14) Uani d . 1
O O8 0.7533(4) 0.1438(3) 0.2636(3) 0.0534(7) Uani d . 1
C C2 0.4980(4) 0.3307(4) 0.8676(3) 0.0342(8) Uani d . 1
C C4 0.2319(5) 0.2437(5) 0.8299(4) 0.0372(8) Uani d . 1
O O7 0.9082(4) 0.3746(4) 0.1279(3) 0.0559(7) Uani d . 1
C C8 0.8514(5) 0.2514(5) 0.2480(4) 0.0402(8) Uani d . 1
C C3 0.3572(4) 0.2377(4) 0.9116(4) 0.0358(8) Uani d . 1
O O6 0.8979(3) 0.1258(3) 0.7387(2) 0.0482(7) Uani d . 1
O O4 0.1034(4) 0.1408(4) 0.9054(3) 0.0553(7) Uani d . 1
O O1 0.7273(4) 0.4053(3) 0.9363(3) 0.0523(7) Uani d . 1
C C5 0.9442(5) 0.2002(5) 0.6086(4) 0.0369(8) Uani d . 1
C C6 0.8569(5) 0.1816(4) 0.5055(4) 0.0369(8) Uani d . 1
O O2 0.5820(4) 0.1726(4) 1.0752(3) 0.0620(8) Uani d . 1
C C7 0.9219(5) 0.2552(5) 0.3632(4) 0.0393(8) Uani d . 1
O O5 1.0728(4) 0.3031(4) 0.5434(3) 0.0639(8) Uani d . 1
C C1 0.6154(5) 0.3058(5) 0.9637(4) 0.0376(8) Uani d . 1
O O3 0.2492(4) 0.3336(4) 0.7044(3) 0.0615(8) Uani d . 1
H H7O 0.8624 0.3720 0.0675 0.084 Uiso calc R 1
H H3 0.3296 0.1537 1.0068 0.043 Uiso d R 1
H H4 0.0409 0.1432 0.8545 0.083 Uiso calc R 1
H H2 0.6474 0.1655 1.1253 0.093 Uiso calc R 1
H H7 1.0273 0.3166 0.3377 0.047 Uiso d R 1
H H5 1.1256 0.3006 0.6011 0.096 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br2 0.0524(3) 0.0857(4) 0.0506(2) -0.0289(2) -0.01035(19) -0.0224(2)
Br1 0.0495(2) 0.0573(3) 0.0433(2) -0.01669(19) -0.01746(18) -0.00144(18)
O8 0.0680(18) 0.0545(17) 0.0518(15) -0.0154(15) -0.0354(14) -0.0115(13)
C2 0.0372(19) 0.040(2) 0.0298(16) -0.0034(16) -0.0118(15) -0.0135(15)
C4 0.0379(19) 0.043(2) 0.0383(19) -0.0073(17) -0.0154(16) -0.0160(17)
O7 0.0632(18) 0.076(2) 0.0339(13) -0.0234(15) -0.0233(13) -0.0058(14)
C8 0.038(2) 0.050(2) 0.039(2) -0.0019(18) -0.0176(16) -0.0172(18)
C3 0.0385(19) 0.039(2) 0.0351(17) -0.0064(16) -0.0147(15) -0.0124(15)
O6 0.0477(15) 0.0671(18) 0.0335(13) -0.0155(13) -0.0165(11) -0.0104(12)
O4 0.0502(16) 0.0739(19) 0.0502(15) -0.0276(15) -0.0230(13) -0.0106(14)
O1 0.0561(16) 0.0621(18) 0.0481(14) -0.0235(14) -0.0271(13) -0.0080(13)
C5 0.0360(19) 0.044(2) 0.0365(18) -0.0016(17) -0.0176(16) -0.0139(16)
C6 0.0355(19) 0.040(2) 0.0421(19) -0.0028(16) -0.0172(16) -0.0158(16)
O2 0.084(2) 0.0598(19) 0.0561(17) -0.0280(16) -0.0477(16) 0.0023(14)
C7 0.040(2) 0.049(2) 0.0375(19) -0.0053(17) -0.0203(16) -0.0136(17)
O5 0.074(2) 0.087(2) 0.0383(14) -0.0440(18) -0.0270(14) -0.0014(14)
C1 0.040(2) 0.043(2) 0.0349(18) -0.0065(17) -0.0130(15) -0.0149(16)
O3 0.0688(19) 0.077(2) 0.0478(16) -0.0343(16) -0.0315(14) -0.0025(15)
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'
Br Br -0.2901 2.4595 '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'
loop_
_diffrn_radiation_wavelength
0.71073
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C2 C1 120.9(3)
C3 C2 Br1 125.3(2)
C1 C2 Br1 113.8(2)
O3 C4 O4 123.7(3)
O3 C4 C3 123.8(3)
O4 C4 C3 112.5(3)
O8 C8 O7 124.3(3)
O8 C8 C7 123.9(3)
O7 C8 C7 111.9(3)
C2 C3 C4 127.5(3)
O6 C5 O5 124.3(3)
O6 C5 C6 123.3(3)
O5 C5 C6 112.4(3)
C7 C6 C5 120.8(3)
C7 C6 Br2 124.7(3)
C5 C6 Br2 114.5(2)
C6 C7 C8 127.6(3)
O1 C1 O2 124.9(3)
O1 C1 C2 122.1(3)
O2 C1 C2 112.9(3)
C8 O7 H7O 109.5
C2 C3 H3 119.2
C4 C3 H3 113.2
C4 O4 H4 109.5
C1 O2 H2 109.5
C6 C7 H7 112.5
C8 C7 H7 119.9
C5 O5 H5 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br2 C6 1.860(3)
Br1 C2 1.861(3)
O8 C8 1.217(4)
C2 C3 1.320(4)
C2 C1 1.500(4)
C4 O3 1.216(4)
C4 O4 1.290(4)
C4 C3 1.472(4)
O7 C8 1.295(4)
C8 C7 1.472(4)
O6 C5 1.212(4)
O1 C1 1.210(4)
C5 O5 1.284(4)
C5 C6 1.497(4)
C6 C7 1.321(5)
O2 C1 1.274(4)
O7 H7O 0.8200
C3 H3 0.9600
O4 H4 0.8200
O2 H2 0.8200
C7 H7 0.9601
O5 H5 0.8200
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
O7 H7O O1 1_554 0.82 1.89 2.702(3) 168.3
O4 H4 O6 1_455 0.82 1.93 2.752(3) 174.6
O2 H2 O8 1_556 0.82 1.81 2.621(3) 169.4
O5 H5 O3 1_655 0.82 1.76 2.574(3) 169.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 556534
