#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/49/7114918.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_7114918
loop_
_publ_author_name
'Robinson, James J.'
'Buchanan, J. Grant'
'Kinsman, Richard G.'
'Mahon, Mary F.'
'Williams, Ian H.'
'Charlton, Michael H.'
_publ_section_title
;
 Evidence for α-lactone intermediates in addition of aqueous bromine to
 disodium dimethyl-maleate and -fumarate
;
_journal_issue                   5
_journal_name_full               'Chemical Communications'
_journal_page_first              485
_journal_paper_doi               10.1039/b100335f
_journal_year                    2001
_chemical_formula_sum            'C6 H7 Br O4'
_chemical_formula_weight         223.03
_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                 92.812(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4057(9)
_cell_length_b                   6.4044(4)
_cell_length_c                   12.0468(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     801.86(11)
_computing_data_reduction        'Denzo and Scalepack (otwinowski & Minor, 1997'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  '4-circle diffractometer'
_diffrn_measurement_method       'scintillation counter'
_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  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8001
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    5.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.0055(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.895
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0837P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                1328
_reflns_number_total             1842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b100335f.txt
_cod_data_source_block           (Compound_4)k00gb1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7114918
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
Br1 Br 0.89130(3) 0.00171(4) 0.88052(3) 0.0473(2) Uani 1 1 d .
O1 O 0.78026(18) -0.3379(3) 0.67348(16) 0.0375(5) Uani 1 1 d .
O2 O 0.7371(3) -0.4790(3) 0.8425(2) 0.0518(7) Uani 1 1 d .
O3 O 0.6333(2) 0.1399(3) 0.57498(19) 0.0379(5) Uani 1 1 d .
H3 H 0.569(3) 0.159(4) 0.534(2) 0.029(8) Uiso 1 1 d .
O4 O 0.57535(18) -0.1966(3) 0.55755(16) 0.0334(5) Uani 1 1 d .
C1 C 0.7519(3) -0.3343(4) 0.7824(2) 0.0356(7) Uani 1 1 d .
C2 C 0.7442(2) -0.0971(4) 0.7895(2) 0.0293(6) Uani 1 1 d .
C3 C 0.7692(3) -0.1085(4) 0.6624(2) 0.0303(6) Uani 1 1 d .
C4 C 0.6219(3) 0.0016(3) 0.8285(3) 0.0353(7) Uani 1 1 d .
H4A H 0.5477 -0.0534 0.7845 0.053 Uiso 1 1 calc R
H4B H 0.6262 0.1533 0.8191 0.053 Uiso 1 1 calc R
H4C H 0.6127 -0.0315 0.9072 0.053 Uiso 1 1 calc R
C5 C 0.8873(3) -0.0100(4) 0.6168(3) 0.0449(9) Uani 1 1 d .
H5A H 0.9643 -0.0635 0.6574 0.067 Uiso 1 1 calc R
H5B H 0.8830 0.1419 0.6257 0.067 Uiso 1 1 calc R
H5C H 0.8912 -0.0445 0.5378 0.067 Uiso 1 1 calc R
C6 C 0.6487(3) -0.0601(5) 0.5920(2) 0.0300(6) 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 0.0532(3) 0.0410(3) 0.0451(3) -0.00293(11) -0.02377(19) -0.00210(12)
O1 0.0442(12) 0.0316(10) 0.0362(11) -0.0043(8) -0.0033(9) 0.0086(8)
O2 0.077(2) 0.0270(12) 0.0509(16) 0.0086(9) 0.0000(14) 0.0019(9)
O3 0.0433(13) 0.0303(11) 0.0387(12) 0.0027(9) -0.0125(10) -0.0012(9)
O4 0.0354(11) 0.0320(10) 0.0320(10) 0.0033(8) -0.0059(9) -0.0058(8)
C1 0.0398(17) 0.0292(15) 0.0369(16) -0.0015(12) -0.0065(12) 0.0028(11)
C2 0.0350(16) 0.0265(14) 0.0260(14) 0.0003(11) -0.0038(11) 0.0000(11)
C3 0.0339(16) 0.0258(14) 0.0310(15) 0.0005(10) -0.0003(12) 0.0004(11)
C4 0.0438(19) 0.0319(16) 0.0304(15) 0.0018(10) 0.0040(15) 0.0030(11)
C5 0.0320(18) 0.062(2) 0.041(2) 0.0065(13) 0.0050(15) -0.0038(12)
C6 0.0311(15) 0.0345(14) 0.0248(14) 0.0014(12) 0.0057(12) 0.0011(13)
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'
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
C1 O1 C3 92.89(18)
O2 C1 O1 127.9(3)
O2 C1 C2 137.2(3)
O1 C1 C2 94.9(2)
C4 C2 C1 118.7(2)
C4 C2 C3 120.3(2)
C1 C2 C3 83.52(19)
C4 C2 Br1 109.83(19)
C1 C2 Br1 108.30(17)
C3 C2 Br1 113.73(17)
O1 C3 C5 112.8(2)
O1 C3 C6 108.2(2)
C5 C3 C6 112.2(2)
O1 C3 C2 88.53(18)
C5 C3 C2 120.9(2)
C6 C3 C2 111.5(2)
O4 C6 O3 125.4(3)
O4 C6 C3 122.2(3)
O3 C6 C3 112.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.944(3)
O1 C1 1.359(3)
O1 C3 1.479(3)
O2 C1 1.191(3)
O3 C6 1.306(4)
O4 C6 1.219(4)
C1 C2 1.524(4)
C2 C4 1.516(4)
C2 C3 1.567(3)
C3 C5 1.508(4)
C3 C6 1.512(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101102042
